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Sample records for carvacrol thymol eugenol

Bactericidal action of binary and ternary mixtures of carvacrol, thymol, and eugenol against Listeria innocua.

PubMed

García-García, Rebeca; López-Malo, Aurelio; Palou, Enrique

2011-03-01

The bactericidal effect of 3 natural agents (carvacrol, thymol, and eugenol) was evaluated as well as their binary and ternary mixtures on Listeria innocua inactivation in liquid model systems. Minimal bactericidal concentrations (MBC) of these agents were determined, and then binary and ternary mixtures were evaluated. Culture media were inoculated with L. innocua and incubated for 72 h at 35 °C. Turbidity of studied systems were determined every 24 h. The most effective individual antimicrobial agent was carvacrol, followed by thymol and then eugenol with MBCs of 150, 250, and 450 mg kg(-1), respectively. It was observed that the most effective binary mixture was 75 mg kg(-1) carvacrol and 62.5 mg kg(-1) thymol. Furthermore, the ternary mixture carvacrol-thymol-eugenol in concentrations of 75, 31.25, and 56.25 mg kg(-1), correspondingly, was the most effective for L. innocua inactivation. Several binary and ternary mixtures of these 3 natural antimicrobial agents worked adequately to inactivate L. innocua.
Antifungal efficacy of thymol, carvacrol, eugenol and menthol as alternative agents to control the growth of food-relevant fungi.

PubMed

Abbaszadeh, S; Sharifzadeh, A; Shokri, H; Khosravi, A R; Abbaszadeh, A

2014-06-01

This work is an attempt to examine the antifungal activity of thymol, carvacrol, eugenol and menthol against 11 food-decaying fungi. The susceptibility test for the compounds was carried out in terms of minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) using microdilution method in 96 multi-well microtiter plates. Results indicated that all compounds were effective to varying extents against various fungal isolates, with the highest efficacy displayed by carvacrol (mean MIC value: 154.5 μg/mL) (P<0.05). The incorporation of increased concentrations of all compounds to the media led to progressive and significant reduction in growth for all fungi. The most potent inhibitory activity of thymol, carvacrol, eugenol and menthol was found for Cladosporium spp. (MIC: 100 μg/mL), Aspergillus spp. (MIC: 100 μg/mL), Cladosporium spp. (MIC: 350 μg/mL), and Aspergillus spp. and Cladosporium spp. (MIC: 125 μg/mL), respectively. Thus, the application of these herbal components could be considered as a good alternatives to inhibit fungal growth and to reduce the use of synthetic fungicides. Copyright © 2014 Elsevier Masson SAS. All rights reserved.
Assessment of antioxidative, chelating, and DNA-protective effects of selected essential oil components (eugenol, carvacrol, thymol, borneol, eucalyptol) of plants and intact Rosmarinus officinalis oil.

PubMed

Horvathova, Eva; Navarova, Jana; Galova, Eliska; Sevcovicova, Andrea; Chodakova, Lenka; Snahnicanova, Zuzana; Melusova, Martina; Kozics, Katarina; Slamenova, Darina

2014-07-16

Selected components of plant essential oils and intact Rosmarinus officinalis oil (RO) were investigated for their antioxidant, iron-chelating, and DNA-protective effects. Antioxidant activities were assessed using four different techniques. DNA-protective effects on human hepatoma HepG2 cells and plasmid DNA were evaluated with the help of the comet assay and the DNA topology test, respectively. It was observed that whereas eugenol, carvacrol, and thymol showed high antioxidative effectiveness in all assays used, RO manifested only antiradical effect and borneol and eucalyptol did not express antioxidant activity at all. DNA-protective ability against hydrogen peroxide (H2O2)-induced DNA lesions was manifested by two antioxidants (carvacrol and thymol) and two compounds that do not show antioxidant effects (RO and borneol). Borneol was able to preserve not only DNA of HepG2 cells but also plasmid DNA against Fe(2+)-induced damage. This paper evaluates the results in the light of experiences of other scientists.
Bactericidal activities of plant essential oils and some of their isolated constituents against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica.

PubMed

Friedman, Mendel; Henika, Philip R; Mandrell, Robert E

2002-10-01

An improved method of sample preparation was used in a microplate assay to evaluate the bactericidal activity levels of 96 essential oils and 23 oil compounds against Campylobacter jejuni, Escherichia coli O157:H7, Listeria monocytogenes, and Salmonella enterica obtained from food and clinical sources. Bactericidal activity (BA50) was defined as the percentage of the sample in the assay mixture that resulted in a 50% decrease in CFU relative to a buffer control. Twenty-seven oils and 12 compounds were active against all four species of bacteria. The oils that were most active against C. jejuni (with BA50 values ranging from 0.003 to 0.009) were marigold, ginger root, jasmine, patchouli, gardenia, cedarwood, carrot seed, celery seed, mugwort, spikenard, and orange bitter oils; those that were most active against E. coli (with BA50 values ranging from 0.046 to 0.14) were oregano, thyme, cinnamon, palmarosa, bay leaf, clove bud, lemon grass, and allspice oils; those that were most active against L monocytogenes (with BA50 values ranging from 0.057 to 0.092) were gardenia, cedarwood, bay leaf, clove bud, oregano, cinnamon, allspice, thyme, and patchouli oils; and those that were most active against S. enterica (with BA50 values ranging from 0.045 to 0.14) were thyme, oregano, cinnamon, clove bud, allspice, bay leaf, palmarosa, and marjoram oils. The oil compounds that were most active against C. jejuni (with BA50 values ranging from 0.003 to 0.034) were cinnamaldehyde, estragole, carvacrol, benzaldehyde, citral, thymol, eugenol, perillaldehyde, carvone R, and geranyl acetate; those that were most active against E. coli (with BA50 values ranging from 0.057 to 0.28) were carvacrol, cinnamaldehyde, thymol, eugenol, salicylaldehyde, geraniol, isoeugenol, citral, perillaldehyde, and estragole; those that were most active against L monocytogenes (with BA50 values ranging from 0.019 to 0.43) were cinnamaldehyde, eugenol, thymol, carvacrol, citral, geraniol, perillaldehyde, carvone S, estragole, and salicylaldehyde; and those that were most active against S. enterica (with BA50 values ranging from 0.034 to 0.21) were thymol, cinnamaldehyde, carvacrol, eugenol, salicylaldehyde, geraniol, isoeugenol, terpineol, perillaldehyde, and estragole. The possible significance of these results with regard to food microbiology is discussed.
Behavioral and toxicological responses of Rhodnius prolixus and Triatoma infestans (Hemiptera: Reduviidae) to 10 monoterpene alcohols.

PubMed

Moretti, A N; Zerba, E N; Alzogaray, Raúl A

2013-09-01

The effect on locomotor activity, the repellency, and the knock-down produced by 10 monoterpene alcohols were evaluated on first-instar nymphs of Rhodnius prolixus and Triatoma infestans, vectors of Chagas disease. A video tracking technique was used to evaluate locomotor activity and repellency by exposure to papers impregnated with monoterpenes. Eugenol on R. prolixus and (S)-cis-verbenol on T. infestans did not modify the locomotor activity. The remaining monoterpenes produced hyperactivity on both species, although the concentration required was at least a 1,000 times higher than that of deltamethrin (positive control). Carvacrol, eugenol, and geraniol resulted as repellent as N,N-diethyl-m-toluamide (positive control) for both species. A similar result was observed for almost every monoterpene on T. infestans. Knock-down effect was evaluated by exposing the nymphs in closed recipients. The order of increasing toxicity on R. prolixus was (KT50 values in min): geraniol (213.7) < alpha-terpineol (164.5) < linalool (124.2) < carvacrol (111.6) < eugenol (89.8) < thymol (78.9), and on T. infestans: alpha-terpineol (289.8) < eugenol (221.3) < carvacrol (164.2) < linalool (154.9) < thymol (96.7). All monoterpenes were less toxic than the positive control, dichlorvos (3.6 min for R. prolixus and 3.9 min for T. infestans). After 7 h of exposure, (-)-carveol, citronellol, and menthol (on both species) and geraniol (on T. infestans) produced < 50% of knock-down. After these results, it is worthwhile to explore more deeply the potential of these compounds as tools for controlling Chagas disease vectors.
Synergism between carvacrol or thymol increases the antimicrobial efficacy of soy sauce with no sensory impact.

PubMed

Moon, Hyeree; Rhee, Min Suk

2016-01-18

Here, we examined the antimicrobial effects of soy sauce containing essential oils (EOs) against Escherichia coli O157:H7, Salmonella Typhimurium, and Listeria monocytogenes at 22°C and 4°C. To screen a variety of combined effects, soy sauce was mixed with six different EOs (carvacrol, thymol, eugenol, trans-cinnamaldehyde, β-resorcylic acid, and vanillin), each at a concentration of 1mM for 10 min. None of the oils showed bactericidal activity when used alone. Soy sauce combined with carvacrol and thymol induced the greatest antibacterial activity against all tested bacteria; therefore, these oils were further tested at 0.25, 0.5, and 1mM (0.0039%, 0.0078%, and 0.0157%) for 1, 5, and 10 min at 4°C and 22°C. In addition, sensory evaluation of soy sauce containing each EO at 0.25, 0.5, 1, and 2mM was performed using the nine point hedonic test. Carvacrol or thymol (1mM) eliminated all the test bacteria (initial population, 7.0-7.5logCFU/ml) in 1-5 min at 22°C and within 10 min at 4°C. L. monocytogenes was slightly more tolerant at 4°C, which may be attributable to the ability of the cell membrane to adapt to low temperatures. The sensory scores for soy sauce containing EOs were not significantly different from that of soy sauce without EOs (P>0.05). The stability of EO efficacy in soy sauce was also verified. These results suggest that carvacrol and thymol act synergistically with other factors present in soy sauce to increase antimicrobial activity against major foodborne pathogens at both 4°C and 22°C. The synergism may be attributable to the combination of factors (mainly high salt concentration and low pH imparted by organic acids) present in soy sauce and the membrane attacking properties of carvacrol and thymol. This method will facilitate the production of microbiologically safe soy sauce, soy sauce-based marinades, and various marinated foods. Copyright © 2015 Elsevier B.V. All rights reserved.
Antibacterial potential of phytochemicals alone or in combination with antimicrobials against fish pathogenic bacteria.

PubMed

Bandeira Junior, G; Sutili, F J; Gressler, L T; Ely, V L; Silveira, B P; Tasca, C; Reghelin, M; Matter, L B; Vargas, A P C; Baldisserotto, B

2018-05-09

This study investigated the antibacterial activity of five phytochemicals (carvacrol, citral, eugenol, linalool, and thymol) alone or in combination with florfenicol or oxytetracycline against bacteria isolated from silver catfish (Rhamdia quelen). We also analyzed the potential of these compounds to inhibit biofilm formation and hemolysis caused by the bacteria. Bacteria were tested with antimicrobials to calculate the multiple antibiotic resistance (MAR). The checkerboard assay was used to evaluate a putative synergy between five phytochemicals and antimicrobials against the strains isolated. The biofilm formation inhibition assay was performed with phytochemicals and antimicrobials, and the hemolysis inhibition assay was performed with the phytochemicals. Carvacrol, eugenol and thymol were the most effective phytochemicals. Three combinations (linalool with florfenicol or oxytetracycline against Aeromonas hydrophila and citral with oxytetracycline against Citrobacter freundii) demonstrated synergy in the checkerboard assay. All phytochemicals inhibited biofilm formation and hemolysis activity. The tested phytochemicals showed satisfactory activity against fish pathogenic bacteria. The phytochemicals did not present antagonistic interactions with the antimicrobials, allowing their combined use, which may contribute to a decrease in the use of conventional drugs and their residues in aquatic environment. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.
Synergistic interaction of ten essential oils against Haemonchus contortus in vitro.

PubMed

Katiki, L M; Barbieri, A M E; Araujo, R C; Veríssimo, C J; Louvandini, H; Ferreira, J F S

2017-08-30

Anthelmintic resistance in sheep gastrointestinal nematodes is a worldwide problem. Multi-drug resistant haemonchosis is the most serious impediment for small ruminant systems, and there are no new drug candidates currently under development. Molecules from natural sources have demonstrated anthelmintic activity against parasites. In this work, the monoterpenoids carvacrol, carvone, cineole, linalool, limonene, and thymol and the phenylpropanoids cinnamaldehyde, anethole, vanillin, and eugenol were assessed individually or in mixtures of ten binary, three ternary, and three quaternary combinations using the in vitro egg hatch assay with eggs of a multi-drug resistant strain of Haemonchus contortus. The main objective of this study was to identify the most effective interaction among essential oils with the greatest individual anthelmintic efficacy and to determine the most powerful combinations. The essential oils were ranked by their 50% lethal concentration (LC 50 ) as follows (mg/mL): cinamaldehyde (0.018), anethole (0.070), carvone (0.085), carvacrol (0.11), thymol (0.13), linalool (0.29), vanillin (0.57), eugenol (0.57), cineole (4.74), and limonene (207.5). Quantification of synergism, additive effect, and antagonism were calculated for binary, ternary, and quaternary combinations. The best anthelmintic effect resulting from synergistic activity among 16 different combinations was for cinnamaldehyde:carvacrol (CL 50 0.012mg/mL) and anethole:carvone (CL 50 0.013mg/mL). These results indicate that these binary combinations would be promising to be tested in sheep infected with H. contortus. Copyright © 2017 Elsevier B.V. All rights reserved.
Combination of carvacrol and thymol against the poultry red mite (Dermanyssus gallinae).

PubMed

Masoumi, Farzam; Youssefi, Mohammad Reza; Tabari, Mohaddeseh Abouhosseini

2016-11-01

Pest management by conventional pesticides has become progressively hindered by developing pest resistance and increase in consumers demand for safe and residue-free foodstuffs. This will create a considerable market opportunity for alternative products, including botanical pesticides. The present study was conducted to assess the combination of carvacrol and thymol, their repellent activity, and residual toxicity against Dermanyssus gallinae with the aim of designing a new strategy relying on natural compounds for the control of D. gallinae. Different ratios of carvacrol-thymol, 5:0, 4:1, 3:2, 2:3, 1:4, and 0:5 based on LD50 values, were tested for their toxicity on D. gallinae. For residual toxicity assay, mortality rate of mites recorded after being exposed to the surfaces 1, 3, 7, 14, 21, and 28 days post spraying by carvacrol-thymol preparation. In combination toxicity, carvacrol-thymol in 4:1 ratio showed the highest efficacy against D. gallinae. The highest repellent activity was observed in carvacrol-thymol 5:0 combination. Addition of thymol to carvacrol resulted in a decrease in repellent activity of carvacrol as was seen in carvacrol-thymol 3:2, 2:3, and 1:4 ratios (p < 0.05). Carvacrol-thymol in 4:1 ratio at 2 % concentration displayed good residual toxicity and was effective against D. gallinae till 14 days post spraying (p < 0.05). The present study showed that the combination of carvacrol-thymol particularly with a 4:1 ratio displayed improved acaricidal activity and good residual toxicity. However, combining the application of carvacrol and thymol did not show any synergistic effect on repellent activity. Overall, carvacrol-thymol can be suggested as an alternative strategy for the control of D. gallinae.
Antifungal activity of synthetic antiseptics and natural compounds against Candida dubliniensis before and after in vitro fluconazole exposure.

PubMed

Reginato, Cássia Franco; Bandeira, Laíssa Arévalo; Zanette, Régis Adriel; Santurio, Janio Morais; Alves, Sydney Hartz; Danesi, Cristiane Cademartori

2017-01-01

This study evaluated the susceptibilities of oral candidiasis-derived Candida albicans, fluconazole-resistant (FR) Candida dubliniensis, and fluconazole-susceptible (FS) C. dubliniensis to synthetic antiseptics [chlorhexidine gluconate (CHX), cetylpyridinium chloride (CPC), and triclosan (TRC)] and natural compounds (carvacrol, eugenol and thymol). Susceptibility tests were performed based on the M27-A3 reference method. The fluconazole-resistant C. dubliniensis strains were obtained after prolonged in vitro exposure to increasing fluconazole concentrations. The geometric mean values for minimum inhibitory concentrations and minimum fungicidal concentrations were compared among the groups. Fluconazole-susceptible C. dubliniensis was more sensitive to CPC and TRC than FR C. dubliniensis and C. albicans were. However, eugenol and thymol were more active against FR C. dubliniensis. The fungicidal activities of CHX and TRC were similar for the three groups, and FR C. dubliniensis and C. albicans had similar sensitivities to CPC. The resistance of C. dubliniensis to fluconazole affects its sensitivity the synthetic antiseptics and natural compounds that were tested.
Eugenol and carvacrol excite first- and second-order trigeminal neurons and enhance their heat-evoked responses

PubMed Central

Klein, Amanda H.; Joe, Christopher L.; Davoodi, Auva; Takechi, Kenichi; Carstens, Mirela Iodi; Carstens, E

2014-01-01

Eugenol and carvacrol from clove and oregano, respectively, are agonists of the warmth-sensitive transient receptor potential channel TRPV3 and the irritant-sensitive TRPA1. Eugenol and carvacrol induce oral irritation that rapidly desensitizes, accompanied by brief enhancement of innocuous warmth and heat pain in humans. We presently investigated if eugenol and carvacrol activate nociceptive primary afferent and higher-order trigeminal neurons and enhance their heat-evoked responses, using calcium imaging of cultured trigeminal ganglion (TG) and dorsal root ganglion (DRG) neurons, and in vivo single-unit recordings in trigeminal subnucleus caudalis (Vc) of rats. Eugenol and carvacrol activated 20-30% of TG and 7-20% of DRG cells, the majority of which additionally responded to menthol, mustard oil and/or capsaicin. TG cell responses to innocuous (39°) and noxious (42°C) heating were enhanced by eugenol and carvacrol. We identified dorsomedial Vc neurons responsive to noxious heating of the tongue in pentobarbital-anesthetized rats. Eugenol and carvacrol dose-dependently elicited desensitizing responses in 55% and 73% of heat-sensitive units, respectively. Responses to noxious heat were briefly enhanced by eugenol and carvacrol. Many eugenol- and carvacrol-responsive units also responded to menthol, cinnamaldehyde and capsaicin. These data support a peripheral site for eugenol and carvacrol to enhance warmth- and noxious heat-evoked responses of trigeminal neurons, and are consistent with the observation that these agonists briefly enhance warmth and heat pain on the human tongue. PMID:24759772
Bioassay-guided investigation of two Monarda essential oils as repellents of yellow fever mosquito Aedes aegypti.

PubMed

Tabanca, Nurhayat; Bernier, Ulrich R; Ali, Abbas; Wang, Mei; Demirci, Betul; Blythe, Eugene K; Khan, Shabana I; Baser, K Husnu Can; Khan, Ikhlas A

2013-09-11

As part of an ongoing research program to identify active mosquito repellents, Monarda bradburiana Beck and Monarda fistulosa L. essential oils showed good repellent activity with minimum effective dosages (MED) of 0.055 ± 0.036 and 0.078 ± 0.027 mg/cm(2), respectively, compared to reference standard N,N-diethyl-3-methylbenzamide (DEET) (0.039 ± 0.014 mg/cm(2)). Systematic bioassay-guided fractionation of essential oils of both Monarda species was performed to identify the active repellent compounds, and isolated pure compounds were individually tested for repellency. Of the isolated compounds, carvacrol, thymol, eugenol, and carvacrol methyl ether were found to be the repellent compounds with MEDs in the range of 0.013-0.063 mg/cm(2). Active repellent compounds were also tested for larvicidal activity against 1-day-old Aedes aegypti larvae. Thymol was the best larvicide among the tested individual compounds (LD50 of 13.9 ppm). None of the individual compounds showed cytotoxicity against mammalian cells; however, the essential oils were toxic to all cell lines.
The Usefulness of Non-Toxic Plant Metabolites in the Control of Bacterial Proliferation.

PubMed

Gutiérrez, Sergio; Morán, Alfredo; Martínez-Blanco, Honorina; Ferrero, Miguel A; Rodríguez-Aparicio, Leandro B

2017-09-01

The effect of generally recognised as safe (GRAS) plant metabolites in regulating the growth of human pathogenic and probiotic bacteria and in the formation of biofilm was investigated. Thymol, carvacrol and eugenol showed the strongest antibacterial action against both pathogenic and probiotic microorganisms, at a subinhibitory concentration (SIC) of ≤50 μg ml -1 . Genistein, hydroquinone, p-hydroxybenzoic acid and resveratrol also showed antibacterial effects but at a wide concentration range (SIC = 50-1000 μg ml -1 ). Catechin, gallic acid, protocatechuic acid and cranberry extracts were the most biologically compatible molecules (SIC ≥ 1000 μg ml -1 ). Regarding the effect on biofilm, it was observed that thymol, carvacrol and eugenol showed antibiofilm activity against all potential pathogenic bacteria tested whilst specifically enhancing probiotic aggregation. Catechin, genistein and cranberry extracts did not inhibit the pathogenic aggregation but they stimulated probiotic biofilm formation, whilst gallic acid, protocateuchic acid, hydroquinone, p-hydroxybenzoic acid and resveratrol did not show opposite effect on biofilm formation between pathogenic and probiotic microorganisms. These results indicate that an appropriate combination of GRAS plant metabolites, which have traditionally been used as dietary constituents due to their health-promoting characteristics, can also be extremely useful in the regulation of bacterial proliferation in the intestinal microbiota. Hence, it is suggested to apply these natural GRAS molecules as dietary supplements in the food industry in order to promote probiotic viability and to prevent or reduce colonisation or proliferation of intestinal pathogens.
Monoterpenoids (thymol, carvacrol and S-(+)-linalool) with anesthetic activity in silver catfish (Rhamdia quelen): evaluation of acetylcholinesterase and GABAergic activity

PubMed Central

Bianchini, A.E.; Garlet, Q.I.; da Cunha, J.A.; Bandeira, G.; Brusque, I.C.M.; Salbego, J.; Heinzmann, B.M.; Baldisserotto, B.

2017-01-01

This study evaluated the anesthetic potential of thymol and carvacrol, and their influence on acetylcholinesterase (AChE) activity in the muscle and brain of silver catfish (Rhamdia quelen). The AChE activity of S-(+)-linalool was also evaluated. We subsequently assessed the effects of thymol and S-(+)-linalool on the GABAergic system. Fish were exposed to thymol and carvacrol (25, 50, 75, and 100 mg/L) to evaluate time for anesthesia and recovery. Both compounds induced sedation at 25 mg/L and anesthesia with 50–100 mg/L. However, fish exposed to carvacrol presented strong muscle contractions and mortality. AChE activity was increased in the brain of fish at 50 mg/L carvacrol and 100 mg/L thymol, and decreased in the muscle at 100 mg/L carvacrol. S-(+)-linalool did not alter AChE activity. Anesthesia with thymol was reversed by exposure to picrotoxin (GABAA antagonist), similar to the positive control propofol, but was not reversed by flumazenil (antagonist of benzodiazepine binding site), as observed for the positive control diazepam. Picrotoxin did not reverse the effect of S-(+)-linalool. Thymol exposure at 50 mg/L is more suitable than carvacrol for anesthesia in silver catfish, because this concentration did not cause any mortality or interference with AChE activity. Thymol interacted with GABAA receptors, but not with the GABAA/benzodiazepine site. In contrast, S-(+)-linalool did not act in GABAA receptors in silver catfish. PMID:29069225
Monoterpenoids (thymol, carvacrol and S-(+)-linalool) with anesthetic activity in silver catfish (Rhamdia quelen): evaluation of acetylcholinesterase and GABAergic activity.

PubMed

Bianchini, A E; Garlet, Q I; da Cunha, J A; Bandeira, G; Brusque, I C M; Salbego, J; Heinzmann, B M; Baldisserotto, B

2017-10-19

This study evaluated the anesthetic potential of thymol and carvacrol, and their influence on acetylcholinesterase (AChE) activity in the muscle and brain of silver catfish (Rhamdia quelen). The AChE activity of S-(+)-linalool was also evaluated. We subsequently assessed the effects of thymol and S-(+)-linalool on the GABAergic system. Fish were exposed to thymol and carvacrol (25, 50, 75, and 100 mg/L) to evaluate time for anesthesia and recovery. Both compounds induced sedation at 25 mg/L and anesthesia with 50-100 mg/L. However, fish exposed to carvacrol presented strong muscle contractions and mortality. AChE activity was increased in the brain of fish at 50 mg/L carvacrol and 100 mg/L thymol, and decreased in the muscle at 100 mg/L carvacrol. S-(+)-linalool did not alter AChE activity. Anesthesia with thymol was reversed by exposure to picrotoxin (GABAA antagonist), similar to the positive control propofol, but was not reversed by flumazenil (antagonist of benzodiazepine binding site), as observed for the positive control diazepam. Picrotoxin did not reverse the effect of S-(+)-linalool. Thymol exposure at 50 mg/L is more suitable than carvacrol for anesthesia in silver catfish, because this concentration did not cause any mortality or interference with AChE activity. Thymol interacted with GABAA receptors, but not with the GABAA/benzodiazepine site. In contrast, S-(+)-linalool did not act in GABAA receptors in silver catfish.
Use of natural antimicrobials to increase antibiotic susceptibility of drug resistant bacteria.

PubMed

Palaniappan, Kavitha; Holley, Richard A

2010-06-15

Plant-derived antibacterial compounds may be of value as a novel means for controlling antibiotic resistant zoonotic pathogens which contaminate food animals and their products. Individual activity of natural antimicrobials (eugenol, thymol, carvacrol, cinnamaldehyde, allyl isothiocyanate (AIT)) and activity when paired with an antibiotic was studied using broth microdilution and checkerboard methods. In the latter assays, fractional inhibitory concentration (FIC) values were calculated to characterize interactions between the inhibitors. Bacteria tested were chosen because of their resistance to at least one antibiotic which had a known genetic basis. Substantial susceptibility of these bacteria toward the natural antimicrobials and a considerable reduction in the minimum inhibitory concentrations (MIC's) of the antibiotics were noted when paired combinations of antimicrobial and antibiotic were used. In the interaction study, thymol and carvacrol were found to be highly effective in reducing the resistance of Salmonella Typhimurium SGI 1 (tet A) to ampicillin, tetracycline, penicillin, bacitracin, erythromycin and novobiocin (FIC<0.4) and resistance of Streptococcus pyogenes ermB to erythromycin (FIC<0.5). With Escherichia coli N00 666, thymol and cinnamaldehyde were found to have a similar effect (FIC<0.4) in reducing the MIC's of ampicillin, tetracycline, penicillin, erythromycin and novobiocin. Carvacrol, thymol (FIC<0.3) and cinnamaldehyde (FIC<0.4) were effective against Staphylococcus aureus blaZ and in reducing the MIC's of ampicillin, penicillin and bacitracin. Allyl isothiocyanate (AIT) was effective in reducing the MIC of erythromycin (FIC<0.3) when tested against S. pyogenes. Fewer combinations were found to be synergistic when the decrease in viable population (log DP) was calculated. Together, fractional inhibitory concentrations < or = 0.5 and log DP<-1 indicated synergistic action between four natural antimicrobials and as many as three antibiotics to which these bacteria were normally resistant. Copyright 2010 Elsevier B.V. All rights reserved.
Carvacrol as a potent natural acaricide against Dermanyssus gallinae.

PubMed

Tabari, Mohaddeseh Abouhosseini; Youssefi, Mohammad Reza; Barimani, Alireza; Araghi, Atefeh

2015-10-01

Resistance to conventional synthetic pesticides has been widely reported in Dermanyssus gallinae in poultry production systems. Introducing novel acaricides to poultry industry today is more urgent than ever. Research in this field recently focused on plants and plant-derived compounds as acaricides. In the present study, acaricidal activity of three plant bioactive components, carvacrol, thymol, and farnesol, was assessed against D. gallinae and compared with synthetic pesticide permethrin. Mode of acaricidal action was determined by contact toxicity and fumigant toxicity bioassays. Except farnesol which did not cause any mortality, carvacrol and thymol were found to be toxic to D. gallinae with LD50 values of 1 and 3.15 μg/cm(3), respectively. Permethrin gave the LD50 value of 31.95 μg/cm(3) which was less efficient than carvacrol and thymol. In fumigant toxicity bioassay, mortality rate in carvacrol- and thymol-treated groups in closed method was significantly higher than the open one. On the other hand, permethrin exhibited poor fumigant toxicity as there was no statistically significant difference between mortality rate in open and closed methods. These findings revealed that mechanism of acaricidal activity of carvacrol and thymol but not permethrin was mainly due to fumigant action. Results of the present study suggested that carvacrol and thymol, especially carvacrol, can be developed as a novel potent bioacaricide against D. gallinae.
Carvacrol and eugenol effectively inhibit Rhizopus stolonifer and control postharvest soft rot decay in peaches.

PubMed

Zhou, D; Wang, Z; Li, M; Xing, M; Xian, T; Tu, K

2018-01-01

This study aimed to investigate the antifungal mechanism of carvacrol and eugenol to inhibit Rhizopus stolonifer and the control of postharvest soft rot decay in peaches. To investigate the antifungal mechanism, the effects of carvacrol and eugenol on the mycelium growth, leakages of cytoplasmic contents, mycelium morphology, cell membrane and membrane composition of R. stolonifer were studied. Carvacrol and eugenol both exhibited dose-dependent antifungal activity against R. stolonifer, carvacrol at a concentration of 2 μl per plant and eugenol at a concentration of 4 μl per plant inhibited fungal growth completely. The two essential oils (EOs) increased cell membrane penetrability and caused the leakage of cytoplasm, nucleic acid and protein content. The observation using scanning electron microscopy and fluorescent microscopy showed modification of the hyphal morphology and breakage of the cell plasma membrane. Decreased ergosterol contents confirmed that the two EOs could destroy the membrane of R. stolonifer. For the in vivo test, the inhibition of soft rot disease and the induction of defence-related enzymes were investigated. Carvacrol and eugenol significantly reduced the incidence and severity of soft rot decay in inoculated peaches. The best treatments for controlling soft rot decay were obtained at 0·5 μl l -1 for carvacrol and 1 μl l -1 for eugenol. The activities of defence-related enzymes in peaches were also enhanced by fumigation with two EOs. This study showed that carvacrol and eugenol could effectively inhibit the growth of R. stolonifer in vitro and successfully control the incidence of soft rot decay in honey peaches. The above findings may be the main antifungal mechanism of carvacrol and eugenol on R. stolonifer. Furthermore, carvacrol and eugenol are helpful for their commercial application on the preservation of fresh fruit. © 2017 The Society for Applied Microbiology.
Characterization of volatile constituents from Origanum onites and their antifungal and antibacterial activity.

PubMed

Altintas, Ayhan; Tabanca, Nurhayat; Tyihák, Erno; Ott, Peter G; Móricz, Agnes M; Mincsovics, Emil; Wedge, David E

2013-01-01

Essential oils obtained by hydrodistillation (HD) and microwave-assisted HD (MWHD) of Origanum onites aerial parts were analyzed by GC and GCIMS. Thirty-one constituents representing 98.6% of the water-distilled oil and 52 constituents representing 99.6% of the microwave-distilled oil were identified. Carvacrol (76.8% HD and 79.2% MWHD) and thymol (4.7% HD and 4.4% MWHD) were characterized as major constituents in both essential oils. Separation of carvacrol and thymol was achieved by overpressured layer chromatography. HPTLC and TLC separations were also compared. Essential oils were evaluated for antifungal activity against the strawberry anthracnose-causing fungal plant pathogens Colletotrichum acutatum, C. fragariae, and C. gloeosporioides using a direct overlay bioautography assay. Furthermore, main oil components carvacrol and thymol were then evaluated for antifungal activity; only carvacrol demonstrated nonselective antifungal activity against the three Colletotrichum species. Thymol and carvacrol were subsequently evaluated in a 96-well microdilution broth assay against Phomopsis obscurans, Fusarium oxysporum, three Colletotrichum species, and Botrytis cinerea. No activity was observed against any of the three Colletotrichum species at or below 30 pM. However, thymol demonstrated antifungal activity and produced 31.7% growth inhibition of P. obscurans at 120 h and 0.3 pM, whereas carvacrol appeared inactive. Thymol and carvacrol at 30 pM showed 51.5 and 36.9% growth inhibition of B. cinerea at 72 h. The mechanism of antibacterial activity was studied in a bioautography-based BioArena system. Thymol and carvacrol showed similar inhibition/killing effect against Bacillus subtilis soil bacteria; the action could be enhanced by the formaldehyde generator and transporter copper (II) ions and could be decreased in the presence of L-arginine, a formaldehyde capturer. Results indicated that Origanum essential oils and its major components thymol and carvacrol appear to generate antimicrobial activity through a mechanism of action where formaldehyde and its reaction products are produced.
Development of a HS-SPME-GC-MS/MS Method for the Quantitation of Thymol and Carvacrol in Bovine Matrices and To Determine Residue Depletion in Milk and Tissues.

PubMed

Armorini, Sara; Yeatts, James E; Mullen, Keena A E; Mason, Sharon E; Mehmeti, Elmira; Anderson, Kevin L; Washburn, Steve P; Baynes, Ronald E

2016-10-11

Thymol and carvacrol may be present in several phytoceutical products but there are no well-defined methods to measure these compounds in meat and milk from treated animals. U.S. regulatory authorities deem their presence as an adulteration of food. A rapid and sensitive HS-SPME-GC-MS/MS method was developed for the detection of thymol and carvacrol in bovine milk, plasma, liver, kidney, and fat. Inter- and intraday precision values were all less than 15.7 and 20.2% for thymol and carvacrol, respectively. The accuracy was in ranges of 69.9-111.8% for thymol and 74.0-119.2% for carvacrol. With the exception of fat tissue, stability studies showed that both compounds are stable over a 2 month period. A pilot pharmacokinetic study was conducted to evaluate the developed analytical method and to provide initial estimates of thymol and carvacrol depletion in plasma, milk, and several tissues. Treatment of lactating dairy cattle with phytoceutical products containing these substances resulted in low but measurable residue levels at 96 h for liver and 36 h for milk with very short apparent plasma and milk half-lives (<3.0 h).

Assessment of carvacrol for control of avian aspergillosis in intratracheally challenged chickens in comparison to voriconazole with a reference on economic impact.

PubMed

Tartor, Y H; Hassan, F A M

2017-11-01

This study was designed to investigate the efficacy of essential oils as an alternative prophylaxis and treatment for avian aspergillosis. The in vitro susceptibility of Aspergillus fumigatus strains to antifungal drugs and carvacrol, thymol, eugenol, thymoquinone and cinnamon was determined using the macrodiffusion and microdilution methods. Carvacrol has antifungal activity in comparison to voriconazole (VCZ) (MIC 0·5, 0·25 μg ml -1 respectively). While cinnamon, euganol, thymol and thymoquinone displayed moderate to weak inhibitory activity. For the efficacy study, five groups of 10-day-old chicks (n = 48) were infected intratracheally either with A. fumigatus conidia or saline (negative control). Chicks in carvacrol prophylactic and treatment (CRPT) group were fed for 10 days beginning from hatch with carvacrol (200 mg kg -1 per diet) supplemented diets. VCZ (VCZT:20 mg kg -1 body weight (BW)), carvacrol treatment (CRT, CRPT) was started upon appearance of the first clinical signs and continued for 10 days. Birds were monitored for an additional 15 days following treatment. Fungal burden and therapeutic efficacy were assessed by survival, BW, quantitative (q) culture (CFU), quantitative real-time PCR (qPCR) and histopathological changes at several time points. Serum biochemical changes were also assessed. VCZT, CRPT, CRT in comparison to the sham-treated (SHAM) group have prolonged survival (87·5, 83·4, 79·2, 41·7% respectively). In VCZT and CRPT, a significant reduction in clinical signs, lesions, CFU and qPCR counts to the limit of detection were observed. CRPT has the lowest BW reduction, economic losses and significant low total cholesterol levels. Carvacrol has a promising potential to be used as a prophylactic and treatment against A. fumigatus. Prognosis of avian aspergillosis is often poor due to delayed diagnosis and treatment failure. However, the widespread uses of azole prophylaxis in birds are thought to be the major driver of azole resistance. These findings create a possibility to develop an effective drug-free alternative strategy for control of avian aspergillosis. © 2017 The Society for Applied Microbiology.
The impact of cooking and delivery modes of thymol and carvacrol on retention and bioaccessibility in starchy foods.

PubMed

Aravena, Gabriela; García, Olga; Muñoz, Ociel; Pérez-Correa, José R; Parada, Javier

2016-04-01

Oregano and thyme possess beneficial properties for human health, mainly attributable to monoterpenes such as thymol and carvacrol. The main objective of this research was to assess, on starchy food, the impact of cooking (boiling and baking) and delivery (ground leaves and essential oil) modes on retention and bioaccessibility of thymol and carvacrol. Retention was assessed after cooking, while bioaccessibility was estimated in cooked samples using an in vitro digestion model. Our results indicate that bioaccessibility was weakly dependent on cooking and delivery modes (27-33%). Boil cooking presented 20% more retention than baking for both compounds. When essential oil was added to the food matrix, thymol was retained almost 25% more when compared with ground leaves' addition. Conversely, carvacrol was retained 39% more when ground leaves were added. Copyright © 2015 Elsevier Ltd. All rights reserved.
2,3-Dideoxyglucosides of selected terpene phenols and alcohols as potent antifungal compounds.

PubMed

James Bound, D; Murthy, Pushpa S; Srinivas, P

2016-11-01

The antifungal activities of novel 2,3-unsaturated and 2,3-dideoxy 1-O-glucosides of carvacrol, thymol, and perillyl alcohol were tested against Aspergillus flavus, Aspergillus ochraceus, Fusarium oxysporum, Saccharomyces cerevisiae and Candida albicans. In the agar well diffusion tests, zones of inhibition for the derivatives of carvacrol, thymol and perillyl alcohol were higher (15-30mm) in the case of filamentous fungi than those for the parent compounds. Their MIC and MFC values indicated that the 2,3-unsaturated and 2,3-dideoxy 1-O-glucosides of carvacrol and thymol exhibited more fungicidal activity than the other compounds. Further, the 2,3-dideoxyglucosides of carvacrol and thymol, exhibited antitoxigenic effects against A. ochraceus and A. flavus and inhibited the production of ochratoxin and aflatoxin-B2. Propidium iodide influx assay demonstrated the lysis of C. albicans cells by carvacrol and its 2,3-unsaturated 1-O-glucoside and the loss of the membrane integrity. These new 2,3-dideoxyglucosides can be useful as antifungal agents and condiments in foods. Copyright © 2016 Elsevier Ltd. All rights reserved.
Antioxidant, Antibacterial, and Cytotoxic Activities of the Ethanolic Origanum vulgare Extract and Its Major Constituents

PubMed Central

Coccimiglio, John; Alipour, Misagh; Jiang, Zi-Hua; Gottardo, Christine

2016-01-01

Oregano is a perennial shrub that grows in the mountains of the Mediterranean and Euro/Irano-Siberian regions. This study was conducted to identify the major constituents of the ethanolic Origanum vulgare extract and examine the cytotoxic, antioxidant, and antibacterial properties of the extract but more importantly the contribution of its specific major constituent(s) or their combination to the overall extract biological activity. Gas chromatography/mass spectroscopy analysis showed that the extract contained monoterpene hydrocarbons and phenolic compounds, the major ones being carvacrol and thymol and to a lesser extent p-cymene, 1-octacosanol, creosol, and phytol. A549 epithelial cells challenged with the extract showed a concentration-dependent increase in cytotoxicity. A combination of thymol and carvacrol at equimolar concentrations to those present in the extract was less cytotoxic. The A549 cells pretreated with nonlethal extract concentrations protected against hydrogen-peroxide-induced cytotoxicity, an antioxidant effect more effective than the combination of equimolar concentrations of thymol/carvacrol. Inclusion of p-cymene and/or 1-octacosanol did not alter the synergistic antioxidant effects of the carvacrol/thymol mixture. The extract also exhibited antimicrobial properties against Gram-positive and Gram-negative bacterial strains including clinical isolates. In conclusion, the oregano extract has cytotoxic, antioxidant, and antibacterial activities mostly attributed to carvacrol and thymol. PMID:27051475
Antifungal Activity of Some Constituents of Origanum vulgare L. Essential Oil Against Postharvest Disease of Peach Fruit.

PubMed

Elshafie, Hazem S; Mancini, Emilia; Sakr, Shimaa; De Martino, Laura; Mattia, Carlo Andrea; De Feo, Vincenzo; Camele, Ippolito

2015-08-01

Plant essential oils (EOs) can potentially replace synthetic fungicides in the management of postharvest fruit and vegetable diseases. The aim of this study was to evaluate in vitro and in vivo effectiveness of thymol, carvacrol, linalool, and trans-caryophyllene, single constituents of the EO of Origanum vulgare L. ssp. hirtum against Monilinia laxa, M. fructigena, and M. fructicola, which are important phytopathogens and causal agents of brown rot of pome and stone fruits in pre- and postharvest. Moreover, the possible phytotoxic activity of these constituents was assessed and their minimum inhibitory concentration (MIC) was determined. In vitro experiment indicated that thymol and carvacrol possess the highest antifungal activity. Results of in vivo trials confirmed the strong efficacy of thymol and carvacrol against brown rot of peach fruits. The thymol MIC resulted to be 0.16 μg/μL against M. laxa and M. fructigena and 0.12 μg/μL against M. fructicola, whereas for carvacrol they were 0.02 μg/μL against the first two Monilinia species and 0.03 μg/μL against the third. Results of this study indicated that thymol and carvacrol could be used after suitable formulation for controlling postharvest fruit diseases caused by the three studied Monilinia species.
Structurally Related Monoterpenes p-Cymene, Carvacrol and Thymol Isolated from Essential Oil from Leaves of Lippia sidoides Cham. (Verbenaceae) Protect Mice against Elastase-Induced Emphysema.

PubMed

Games, Ellen; Guerreiro, Marina; Santana, Fernanda R; Pinheiro, Nathalia M; de Oliveira, Emerson A; Lopes, Fernanda D T Q S; Olivo, Clarice R; Tibério, Iolanda F L C; Martins, Mílton A; Lago, João Henrique G; Prado, Carla M

2016-10-20

Chronic obstructive pulmonary disease (COPD) is characterized by irreversible airflow obstruction and inflammation. Natural products, such as monoterpenes, displayed anti-inflammatory and anti-oxidant activities and can be used as a source of new compounds to COPD treatment. Our aim was to evaluate, in an elastase-induced pulmonary emphysema in mice, the effects of and underlying mechanisms of three related natural monoterpenes ( p -cymene, carvacrol and thymol) isolated from essential oil from leaves Lippia sidoides Cham. (Verbenaceae). Mices received porcine pancreatic elastase (PPE) and were treated with p -cymene, carvacrol, thymol or vehicle 30 min later and again on 7th, 14th and 28th days. Lung inflammatory profile and histological sections were evaluated. In the elastase-instilled animals, the tested monoterpenes reduced alveolar enlargement, macrophages and the levels of IL-1β, IL-6, IL-8 and IL-17 in bronchoalveolar lavage fluid (BALF), and collagen fibers, MMP-9 and p-65-NF-κB-positive cells in lung parenchyma ( p < 0.05). All treatments attenuated levels of 8-iso-PGF2α but only thymol was able to reduced exhaled nitric oxide ( p < 0.05). Monoterpenes p -cymene, carvacrol and thymol reduced lung emphysema and inflammation in mice. No significant differences among the three monoterpenes treatments were found, suggesting that the presence of hydroxyl group in the molecular structure of thymol and carvacrol do not play a central role in the anti-inflammatory effects.
Antifungal, phytotoxic and insecticidal properties of essential oil isolated from Turkish Origanum acutidens and its three components, carvacrol, thymol and p-cymene.

PubMed

Kordali, Saban; Cakir, Ahmet; Ozer, Hakan; Cakmakci, Ramazan; Kesdek, Memis; Mete, Ebru

2008-12-01

The chemical composition of essential oil isolated by hydrodistillation from the aerial parts of Origanum acutidens was analyzed by GC-MS. Carvacrol (87.0%), p-cymene (2.0%), linalool acetate (1.7%), borneol (1.6%) and beta-caryophyllene (1.3%) were found to be as main constituents. Antifungal, phytotoxic and insecticidal activities of the oil and its aromatic monoterpene constituents, carvacrol, p-cymene and thymol were also determined. The antifungal assays showed that O. acutidens oil, carvacrol and thymol completely inhibited mycelial growth of 17 phytopathogenic fungi and their antifungal effects were higher than commercial fungicide, benomyl. However, p-cymene possessed lower antifungal activity. The oil, carvacrol and thymol completely inhibited the seed germination and seedling growth of Amaranthus retroflexus, Chenopodium album and Rumex crispus and also showed a potent phytotoxic effect against these plants. However, p-cymene did not show any phytotoxic effect. Furthermore, O. acutidens oil showed 68.3% and 36.7% mortality against Sitophilus granarius and Tribolium confusum adults, respectively. The findings of the present study suggest that antifungal and herbicidal properties of the oil can be attributed to its major component, carvacrol, and these agents have a potential to be used as fungicide, herbicide as well as insecticide.
Antibacterial activities of plant-derived compounds and essential oils toward Cronobacter sakazakii and Cronobacter malonaticus.

PubMed

Fraňková, Adéla; Marounek, Milan; Mozrová, Věra; Weber, Jaroslav; Klouček, Pavel; Lukešová, Daniela

2014-10-01

Cronobacter sakazakii and C. malonaticus are opportunistic pathogens that cause infections in children and immunocompromised adults. In the present study, the antibacterial activity of 19 plant-derived compounds, 5 essential oils, and an extract of propolis were assessed against C. sakazakii and C. malonaticus. The effects of most of these antimicrobials have not been reported previously. Both strains were susceptible to thymol, carvacrol, thymoquinone, p-cymene, linalool, camphor, citral, eugenol, and trans-cinnamaldehyde as well as cinnamon, lemongrass, oregano, clove, and laurel essential oils; their minimum inhibitory concentrations varied between 0.1 and 2.0 mg/mL. As an alternative treatment method, vapors of the volatiles were tested as an indirect treatment. Vapors of trans-cinnamaldehyde, eugenol, oregano, and cinnamon essential oils inhibited both tested strains, while vapors of linalool were only active against C. sakazakii. To our knowledge, this study is the first time that the inhibitory activity of the vapors of these compounds and essential oils has been reported against Cronobacter spp.
In vitro antimicrobial activities of cinnamon bark oil, anethole, carvacrol, eugenol and guaiazulene against Mycoplasma hominis clinical isolates.

PubMed

Sleha, Radek; Mosio, Petra; Vydrzalova, Marketa; Jantovska, Alexandra; Bostikova, Vanda; Mazurova, Jaroslava

2014-06-01

The aim of this study was to evaluate the antimicrobial effects of five natural substances against 50 clinical isolates of Mycoplasma hominis. The in vitro activity of selected natural compounds, cinnamon bark oil, anethole, carvacrol, eugenol and guaiazulene, was investigated against 50 M. hominis isolates cultivated from cervical swabs by the broth dilution method. All showed valuable antimicrobial activity against the tested isolates. Oil from the bark of Cinnamomum zeylanicum (MBC90 = 500 µg/mL) however was found to be the most effective. Carvacrol (MBC90 = 600 µg/mL) and eugenol (MBC90 = 1000 µg/mL) also possessed strong antimycoplasmal activity. The results indicate that cinnamon bark oil, carvacrol and eugenol have strong antimycoplasmal activity and the potential for use as antimicrobial agents in the treatment of mycoplasmal infections.
Lethal and sublethal effects of essential oil of Lippia sidoides (Verbenaceae) and monoterpenes on Chagas’ disease vector Rhodnius prolixus

PubMed Central

Figueiredo, Marcela B; Gomes, Geovany A; Santangelo, Jayme M; Pontes, Emerson G; Azambuja, Patricia; Garcia, Elói S; de Carvalho, Mário G

2016-01-01

The aim of this study was to identify the composition of the essential oil from leaves of Lippia sidoides (EOLS), a typical shrub commonly found in the dry northeast of Brazil, popularly known as “alecrim-pimenta”. Additionally, we investigated the nymphicidal, ovicidal, phagoinhibitory and excretion effects of EOLS, its major constituent thymol and its isomer carvacrol, on fourth instar nymphs and eggs of Rhodnius prolixus, the Chagas’ disease vector. The nymphicidal and ovicidal activity of thymol, carvacrol, and EOLS was assessed by tests using impregnated Petri dishes. The lethal concentration values (LC50) for EOLS, carvacrol, and thymol were 54.48, 32.98, and 9.38 mg/cm2, respectively. The ovicidal test showed that both carvacrol and thymol (50 mg/cm2) inhibited hatching (50% and 23.3%, respectively), while treatments with 10 mg/cm2 or 50 mg/cm2 EOLS did not affect the hatching rate at all (80% and 90%, respectively). We observed an anti-feeding effect in insects fed with blood containing natural products at the higher concentrations (100 µg/mL). Finally, excretion rate was affected by EOLS and carvacrol, but not by thymol. These findings offer novel insights into basic physiological processes that make the tested natural compounds interesting candidates for new types of insecticides. PMID:27878214
In Vitro Control of Post-Harvest Fruit Rot Fungi by Some Plant Essential Oil Components

PubMed Central

Camele, Ippolito; Altieri, Luciana; De Martino, Laura; De Feo, Vincenzo; Mancini, Emilia; Rana, Gian Luigi

2012-01-01

Eight substances that are main components of the essential oils from three Mediterranean aromatic plants (Verbena officinalis, Thymus vulgaris and Origanum vulgare), previously found active against some phytopathogenic Fungi and Stramenopila, have been tested in vitro against five etiological agents of post-harvest fruit decay, Botrytis cinerea, Penicillium italicum, P. expansum, Phytophthora citrophthora and Rhizopus stolonifer. The tested compounds were β-fellandrene, β-pinene, camphene, carvacrol, citral, o-cymene, γ-terpinene and thymol. Citral exhibited a fungicidal action against P. citrophthora; carvacrol and thymol showed a fungistatic activity against P. citrophthora and R. stolonifer. Citral and carvacrol at 250 ppm, and thymol at 150 and 250 ppm stopped the growth of B. cinerea. Moreover, thymol showed fungistatic and fungicidal action against P. italicum. Finally, the mycelium growth of P. expansum was inhibited in the presence of 250 ppm of thymol and carvacrol. These results represent an important step toward the goal to use some essential oils or their components as natural preservatives for fruits and foodstuffs, due to their safety for consumer healthy and positive effect on shelf life extension of agricultural fresh products. PMID:22408454
Insecticidal toxicities of carvacrol and thymol derived from Thymus vulgaris Lin. against Pochazia shantungensis Chou & Lu., newly recorded pest

NASA Astrophysics Data System (ADS)

Park, Jun-Hwan; Jeon, Ye-Jin; Lee, Chi-Hoon; Chung, Namhyun; Lee, Hoi-Seon

2017-01-01

The insecticidal toxicities of five essential oils against Pochazia shantungensis adults and nymphs, newly recorded pests, were evaluated. The LC50 values of Thymus vulgaris, Ruta graveolens, Citrus aurantium, Leptospermum petersonii and Achillea millefolium oils were recorded as 57.48, 84.44, 92.58, 113.26 and 125.78 mg/L, respectively, against P. shantungensis nymphs using the leaf dipping bioassay, and 75.80, 109.86, 113.26, 145.06 and 153.74 mg/L, respectively, against P. shantungensis adults using the spray bioassay method. Regarding volatile components identified in T. vulgaris oil, the LC50 values of carvacrol and thymol using the leaf dipping bioassay against P. shantungensis nymphs were 56.74 and 28.52 mg/L, respectively. The insecticidal action of T. vulgaris oil against P. shantungensis could be attributed to carvacrol and thymol. Based on the structure-toxicity relationship between thymol analogs and insecticidal toxicities against P. shantungensis nymphs similar to the LC50 values against P. shantungensis adults, the LC50 values of thymol, carvacrol, citral, 2-isopropylphenol, 3-isopropylphenol, and 4-isopropylphenol were 28.52, 56.74 and 89.12, 71.41, 82.49, and 111.28 mg/L, respectively. These results indicate that the insecticidal mode of action of thymol analogs may be largely attributed to the methyl functional group. Thymol analogues have promising potential as first-choice insecticides against P. shantungensis adults and nymphs.
[Determination of carvacrol and thymol in Mosla chinensis by HPLC].

PubMed

Ji, Li; Wang, Fang; Liu, Yuan-yan; Tong, Yan; Li, Xian-duan; Feng, Xue-feng; Huang, Lu-qi; Zhou, Guo-ping

2004-11-01

To establish a quantitative method of determination of carvacrol and thymol in Mosla chinensis. The sample was extracted with 95% ethanol, ODS column was used with methanol-water-acetic acid (60:40:2) as mobile phase. The detection wavelength was set at 274 nm. The linearities of carvacrol and thymol were respectively in the range of 0.23-2.15 microg (r = 0.9999) and 0.39-2.36 microg (r = 0.9999); the average recoveries were 99.9% (RSD 1.4%) and 98.6% (RSD 1.3%); the RSD of repeatability were 1.1% and 1.6%. The method is reliable, and can be used for quality control of M. chinensis.
Phytotoxicity and Cytotoxicity of Essential Oil from Leaves of Plectranthus amboinicus, Carvacrol, and Thymol in Plant Bioassays.

PubMed

Pinheiro, Patrícia Fontes; Costa, Adilson Vidal; Alves, Thammyres de Assis; Galter, Iasmini Nicoli; Pinheiro, Carlos Alexandre; Pereira, Alexandre Fontes; Oliveira, Carlos Magno Ramos; Fontes, Milene Miranda Praça

2015-10-21

The essential oil of Plectranthus amboinicus and its chemotypes, carvacrol and thymol, were evaluated on the germination and root and aerial growth of Lactuca sativa and Sorghum bicolor and in acting on the cell cycle of meristematic root cells of L. sativa. The main component found in the oil by analysis in gas chromatography-mass spectrometry and gas chromatography flame ionization detection was carvacrol (88.61% in area). At a concentration of 0.120% (w v(-1)), the oil and its chemotypes retarded or inhibited the germination and decreased root and aerial growth in monocot and dicot species used in the bioassays. In addition, all substances caused changes in the cell cycle of the meristematic cells of L. sativa, with chromosomal alterations occurring from the 0.015% (w v(-1)) concentration. The essential oil of P. amboinicus, carvacrol, and thymol have potential for use as bioherbicides.
Toxic and repellent activity of selected monoterpenoids (thymol, carvacrol and linalool) against the castor bean tick, Ixodes ricinus (Acari: Ixodidae).

PubMed

Tabari, Mohaddeseh Abouhosseini; Youssefi, Mohammad Reza; Maggi, Filippo; Benelli, Giovanni

2017-10-15

The castor bean tick, Ixodes ricinus, is a species of medical and veterinary importance. The use of synthetic acaricides for tick control has led to development of resistance, residues in the environment and animal products, and public health concerns. In this regard, plant essential oils and their main constituents represent an appealing alternative strategy to combat ticks. The phenols thymol and carvacrol and the alcohol linalool are monoterpenoids occurring in essential oils of several aromatic and medicinal plants, such as thyme, oregano, savory, lavender and coriander. Recent studies have shown toxicity of these monoterpenoids against selected mosquito vectors and other arthropod pests. However, information on their bioactivity on I. ricinus is not available. On this basis, here we evaluated the ovicidal, larvicidal and repellency effects of these compounds against I. ricinus. Concentrations of 0.25, 0.5, 1, 2 and 5% were sprayed on the egg masses, then hatching rates were noted. Larvicidal assays were conducted on unengorged larvae, following the larval packet technique. The repellency was determined by measuring the vertical migration behavior of ticks in laboratory conditions. Carvacrol and thymol at all concentrations tested led to a significant hatching decrease, showing an efficacy higher than permethrin, whereas linalool did not cause any significant effect. In the larvae treated with carvacrol and thymol (1, 2 and 5%), mortality rates reached 100% after 24h, showing a larvicidal efficacy higher than permethrin, whereas no effect was seen in the larval groups treated with linalool. Carvacrol and thymol at all concentrations tested showed >90% repellency on I. ricinus. Linalool was scarcely effective (50.24% repellency) only at the concentration of 5%. Overall, based on these results, the phenols carvacrol and thymol can be considered as candidate ingredients for the development of novel acaricidal formulations to control the populations of I. ricinus and the spread of related tick-borne diseases. Copyright © 2017 Elsevier B.V. All rights reserved.
Short communication: Interaction of the isomers carvacrol and thymol with the antibiotics doxycycline and tilmicosin: In vitro effects against pathogenic bacteria commonly found in the respiratory tract of calves.

PubMed

Kissels, W; Wu, X; Santos, R R

2017-02-01

Bovine respiratory disease is the major problem faced by cattle, specially calves, leading to reduced animal performance and increased mortality, consequently causing important economic losses. Hence, calves must be submitted to antibiotic therapy to counteract this infection usually initiated by the combination of environmental stress factors and viral infection, altering the animal's defense mechanism, and thus allowing lung colonization by the opportunistic bacteria Mannheimia haemolytica and Pasteurella multocida. Essential oils appear to be candidates to replace antibiotics or to act as antibiotic adjuvants due to their antimicrobial properties. In the present study, we aimed to evaluate the 4 essential oil components carvacrol, thymol, trans-anethole, and 1,8 cineole as antibacterial agents or as adjuvants for the antibiotics doxycycline and tilmicosin against M. haemolytica and P. multocida. Bacteria were cultured according to standard protocols, followed by the determination of minimum inhibitory concentration (MIC) and minimum bactericidal concentration. A checkerboard assay was applied to detect possible interactions between components, between antibiotics, and between components and antibiotics. Doxycycline at 0.25 and 0.125 μg/mL inhibited the growth of P. multocida and M. haemolytica, respectively, whereas tilmicosin MIC values were 1.0 and 4.0 μg/mL for P. multocida and M. haemolytica, respectively. Carvacrol MIC values were 2.5 and 1.25 mM for P. multocida and M. haemolytica, respectively, whereas thymol MIC values were 1.25 and 0.625 mM for P. multocida and M. haemolytica, respectively. Trans-anethole and 1,8 cineole did not present any antibacterial effect even at 40 mM against the investigated pathogens. All minimum bactericidal concentration values were the same as MIC, except when thymol was tested against M. haemolytica, being twice the MIC data (i.e., 1.25 mM thymol). Based on fractional inhibitory concentration checkerboard assay, no interaction was observed between doxycycline and tilmicosin. Carvacrol and thymol presented an additive effect when one of them was combined with tilmicosin. Additive effect was also observed when doxycycline was combined with thymol. Synergism was observed when carvacrol was combined with doxycycline or with thymol. Although the antibacterial effects of the tested essential oil components were observed at high concentrations for in vitro conditions, the additive and synergic effects of carvacrol and thymol with antibiotics suggest the option to apply them as antibiotic adjuvants. Copyright © 2017 American Dairy Science Association. Published by Elsevier Inc. All rights reserved.
Composition and antimicrobial activities of Lippia multiflora Moldenke, Mentha x piperita L. and Ocimum basilicum L. essential oils and their major monoterpene alcohols alone and in combination.

PubMed

Bassolé, Imaël Henri Nestor; Lamien-Meda, Aline; Bayala, Balé; Tirogo, Souleymane; Franz, Chlodwig; Novak, Johannes; Nebié, Roger Charles; Dicko, Mamoudou Hama

2010-11-03

Essential oils from leaves of Lippia multiflora, Mentha x piperita and Ocimum basilicum from Burkina Faso were analysed by GC-FID and GC-MS. Major components were p-cymene, thymol, b-caryophyllene, carvacrol and carvone for L. multiflora, menthol and iso-menthone for M. x piperita and, linalool and eugenol for O. basilicum. The essential oils and their major monoterpene alcohols were tested against nine bacterial strains using the disc diffusion and broth microdilution methods. The essential oils with high phenolic contents were the most effective antimicrobials. The checkerboard method was used to quantify the efficacy of paired combinations of essential oils and their major components. The best synergetic effects among essential oils and major components were obtained with combinations involving O. basilicum essential oil and eugenol, respectively. As phenolic components are characterized by a strong spicy aroma, this study suggests that the selection of certain combinations of EOs could help to reduce the amount of essential oils and consequently reduce any adverse sensory impact in food.
Commercial Origanum compactum Benth. and Cinnamomum zeylanicum Blume essential oils against natural mycoflora in Valencia rice.

PubMed

Santamarina, M Pilar; Roselló, Josefa; Sempere, Francisca; Giménez, Silvia; Blázquez, M Amparo

2015-01-01

Chemical composition of commercial Origanum compactum and Cinnamomum zeylanicum essential oils and the antifungal activity against pathogenic fungi isolated from Mediterranean rice grains have been investigated. Sixty-one compounds accounting for more than 99.5% of the total essential oil were identified by using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Carvacrol (43.26%), thymol (21.64%) and their biogenetic precursors p-cymene (13.95%) and γ-terpinene (11.28%) were the main compounds in oregano essential oil, while the phenylpropanoids, eugenol (62.75%), eugenol acetate (16.36%) and (E)-cinnamyl acetate (6.65%) were found in cinnamon essential oil. Both essential oils at 300 μg/mL showed antifungal activity against all tested strains. O. compactum essential oil showed the best antifungal activity towards Fusarium species and Bipolaris oryzae with a total inhibition of the mycelial growth. In inoculated rice grains at lower doses (100 and 200 μg/mL) significantly reduced the fungal infection, so O. compactum essential oil could be used as ecofriendly preservative for field and stored Valencia rice.
Effect of thymol and carvacrol on nutrient digestibility in rams fed high or low concentrate diets.

PubMed

Zamiri, M J; Azizabadi, E; Momeni, Z; Rezvani, M R; Atashi, H; Akhlaghi, A

2015-01-01

Published data on the effects of essential oils (EO) on in vivo nutrient digestibility in sheep are contradictory. In 2 experiments, the effect of thymol and carvacrol on nutrient digestibility was studied in sheep fed with high (70%) or low (52%) concentrate diets, using incomplete Latin Square designs. The essential oils were mixed with the concentrate portion of the diet at the rate of 0.0, 0.3, or 0.6 g per kg dry matter (DM) diet. Supplementation of thymol had no significant effect on digestibility of dry matter (DM), organic matter (OM), crude protein (CP) and acid detergent fiber (ADF). The main effect of thymol on neutral detergent fiber (NDF) and ether extract (EE) digestibility and on nitrogen balance (NB) was significant (P<0.05), but within each level of dietary concentrate no significant differences were observed for these measurements. Overall, ruminal ammonia concentration was higher (P<0.05) in both HCD and LCD lambs receiving 0.3 mg thymol per kg diet. Supplementation of carvacrol had no significant effect on nutrient digestibility. The main effect of carvacrol on ruminal ammonia levels and NB was significant, but within each level of dietary concentrate no significant differences were observed in ammonia levels and NB. Inclusion of 0.3 g/kg diet DM of carvacrol or thyme was more effective than 0.6 g/kg diet DM in terms of NB but neither dose affected nutrient digestibility. Future research should determine the long-term effects of essential oils on digestibility and performance in sheep, before recommendation can be made for their use under practical husbandry conditions.
Antibacterial activities of essential oils and extracts of Turkish Achillea, Satureja and Thymus species against plant pathogenic bacteria.

PubMed

Kotan, Recep; Cakir, Ahmet; Dadasoglu, Fatih; Aydin, Tuba; Cakmakci, Ramazan; Ozer, Hakan; Kordali, Saban; Mete, Ebru; Dikbas, Neslihan

2010-01-15

The aims of this study were to examine the chemical composition of the essential oils and hexane extracts of the aerial parts of Satureja spicigera (C. Koch) Boiss., Thymus fallax Fisch. & CA Mey, Achillea biebersteinii Afan, and Achillea millefolium L. by GC and GC-MS, and to test antibacterial efficacy of essential oils and n-hexane, chloroform, acetone and methanol extracts as an antibacterial and seed disinfectant against 25 agricultural plant pathogens. Thymol, carvacrol, p-cymene, thymol methyl ether and gamma-terpinene were the main constituents of S. spicigera and T. fallax oils and hexane extracts. The main components of the oil of Achillea millefolium were 1,8-cineole, delta-cadinol and caryophyllene oxide, whereas the hexane extract of this species contained mainly n-hexacosane, n-tricosane and n-heneicosane. The oils and hexane extracts of S. spicigera and T. fallax exhibited potent antibacterial activity over a broad spectrum against 25 phytopathogenic bacterial strains. Carvacrol and thymol, the major constituents of S. spicigera and T. fallax oils, also showed potent antibacterial effect against the bacteria tested. The oils of Achillea species showed weak antibacterial activity. Our results also revealed that the essential oil of S. spicigera, thymol and carvacrol could be used as potential disinfection agents against seed-borne bacteria. Our results demonstrate that S. spicigera, T. fallax oils, carvacrol and thymol could become potentials for controlling certain important agricultural plant pathogenic bacteria and seed disinfectant. Copyright (c) 2009 Society of Chemical Industry.

Evaluation of low copper content antifouling paints containing natural phenolic compounds as bioactive additives.

PubMed

Pérez, Miriam; García, Mónica; Blustein, Guillermo

2015-08-01

Cuprous oxide is the most commonly used biocide in antifouling paints. However, copper has harmful effects not only on the fouling community but also on non-target species. In the current study, we investigated the use of thymol, eugenol and guaiacol in this role combined with small quantities of copper. Phenolic compounds were tested for anti-settlement activity against cyprid larvae of the barnacle Balanus amphitrite and for their toxicity to nauplius larvae. Thymol, eugenol and guaiacol were active for anti-settlement but guaiacol had the disadvantage of being toxic to nauplius larvae. However, all of them showed therapeutic ratio>1. Antifouling paints with thymol (low copper content/thymol, LCP/T), eugenol (low copper content/eugenol, LCP/E) and guaiacol (low copper content/guaiacol, LCP/G) combined with small copper content were formulated for field trials. After 12 months exposure in the sea, statistical analysis revealed that LCP/T and LCP/E paints were the most effective combinations and had similar performances to control paints with high copper content (traditional cuprous oxide based paints). In contrast, LCP/G paint was only partially effective in preventing and inhibiting biofouling and was colonized by some hard and soft foulers. However, this antifouling paint was effective against calcareous tubeworm Hydroides elegans. In the light of various potential applications, thymol, eugenol and guaiacol have thus to be considered in future antifouling formulations. Copyright © 2015 Elsevier Ltd. All rights reserved.
Chemical composition of the Lippia origanoides essential oils and their antigenotoxicity against bleomycin-induced DNA damage.

PubMed

Vicuña, Gloria Carolina; Stashenko, Elena E; Fuentes, Jorge Luis

2010-07-01

The present work evaluated the chemical composition of the essential oils (EO) obtained from Lippia origanoides and their DNA protective effect against bleomycin-induced genotoxicity. L. origanoides EO chemical composition was determined by gas chromatography-mass spectrometry (GC-MS). The major compounds of the L. origanoides EOs were thymol (34-58%) and carvacrol (26%). The antigenotoxic effects of the EOs, major compounds and standard compound (epigallocatechin gallate) were assayed in co-incubation procedures using the SOS chromotest in Escherichia coli. Both EOs and their major compounds protected bacterial cells against bleomycin-induced genotoxicity indicating that these two compounds were principally responsible for the antigenotoxicity detected in the oils. Thymol and carvacrol antigenotoxicity was lower than those observed with epigallocatechin gallate. The results were discussed in relation to the chemopreventive potential of L. origanoides EOs and their major components, carvacrol and thymol. Copyright 2009 Elsevier B.V. All rights reserved.
Acaricidal efficacies of Lippia gracilis essential oil and its phytochemicals against organophosphate-resistant and susceptible strains of Rhipicephalus (Boophilus) microplus.

PubMed

Costa-Júnior, Livio M; Miller, Robert J; Alves, Péricles B; Blank, Arie F; Li, Andrew Y; Pérez de León, Adalberto A

2016-09-15

Plant-derived natural products can serve as an alternative to synthetic compounds for control of ticks of veterinary and medical importance. Lippia gracilis is an aromatic plant that produces essential oil with high content of carvacrol and thymol monoterpenes. These monoterpenes have high acaricidal activity against Rhipicephalus (Boophilus) microplus. However, there are no studies that show efficacy differences of essential oils between susceptible and organophosphate resistant strains of R. (B.) microplus. The aim of the present study was to compare acaricidal effects of essential oils extracted from two different genotypes of L. gracilis and the main monoterpenes on larvae of both susceptible and organophosphate resistant R. (B.) microplus larvae. The efficacy of the essential oil of two genotypes of L. gracilis (106 and 201) and their monoterpenes carvacrol and thymol was measured using the larval immersion test on coumaphos-resistant and susceptible strains of R. (B.) microplus. Lethal concentrations were calculated using GraphPad Prism 6.0. Chemical analysis was performed by GC-MS and FID. Thymol and carvacrol were observed to be major constituents in 106 and 201L. gracilis genotype essential oils, respectively. Essential oils of both genotypes were more effective against organophosphate-resistant tick strain than susceptible tick strain. Carvacrol was 3.2 times more toxic to organophosphate resistant strain than to susceptible strain. Thymol was equally toxic to resistant and susceptible tick strains. The significantly higher efficacy monoterpene carvacrol against resistant ticks may lead to development of new natural product acaricide formulations for use to control organophosphate resistant R. (B.) microplus populations. Copyright © 2016 Elsevier B.V. All rights reserved.
Semisynthetic Phenol Derivatives Obtained from Natural Phenols: Antimicrobial Activity and Molecular Properties.

PubMed

Pinheiro, Patrícia Fontes; Menini, Luciana Alves Parreira; Bernardes, Patrícia Campos; Saraiva, Sérgio Henriques; Carneiro, José Walkimar Mesquita; Costa, Adilson Vidal; Arruda, Társila Rodrigues; Lage, Mateus Ribeiro; Gonçalves, Patrícia Martins; Bernardes, Carolina de Oliveira; Alvarenga, Elson Santiago; Menini, Luciano

2018-01-10

Semisynthetic phenol derivatives were obtained from the natural phenols: thymol, carvacrol, eugenol, and guaiacol through catalytic oxychlorination, Williamson synthesis, and aromatic Claisen rearrangement. The compounds characterization was carried out by 1 H NMR, 13 C NMR, and mass spectrometry. The natural phenols and their semisynthetic derivatives were tested for their antimicrobial activity against the bacteria: Staphylococcus aureus, Escherichia coli, Listeria innocua, Pseudomonas aeruginosa, Salmonella enterica Typhimurium, Salmonella enterica ssp. enterica, and Bacillus cereus. Minimum inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) values were determined using concentrations from 220 to 3.44 μg mL -1 . Most of the tested compounds presented MIC values ≤220 μg mL -1 for all the bacteria used in the assays. The molecular properties of the compounds were computed with the PM6 method. Through principle components analysis, the natural phenols and their semisynthetic derivatives with higher antimicrobial potential were grouped.
Alkylphenol Activity against Candida spp. and Microsporum canis: A Focus on the Antifungal Activity of Thymol, Eugenol and O-Methyl Derivatives.

PubMed

Fontenelle, Raquel O S; Morais, Selene M; Brito, Erika H S; Brilhante, Raimunda S N; Cordeiro, Rossana A; Lima, Ynayara C; Brasil, Nilce V G P S; Monteiro, André J; Sidrim, José J C; Rocha, Marcos F G

2011-07-29

In recent years there has been an increasing search for new antifungal compounds due to the side effects of conventional antifungal drugs and fungal resistance. The aims of this study were to test in vitro the activity of thymol, eugenol, estragole and anethole and some O-methyl-derivatives (methylthymol and methyleugenol) against Candida spp. and Microsporum canis. The broth microdilution method was used to determine the minimum inhibitory concentration (MIC). The minimum fungicidal concentrations (MFC) for both Candida spp. and M. canis were found by subculturing each fungal suspension on potato dextrose agar. Thymol, methylthymol, eugenol, methyl-eugenol, anethole, estragole and griseofulvin respectively, presented the following MIC values against M. canis: 4.8-9.7; 78-150; 39; 78-150; 78-150; 19-39 µg/mL and 0.006-2.5 mg/mL. The MFC values for all compounds ranged from 9.7 to 31 µg/mL. Concerning Candida spp, thymol, methylthymol, eugenol, methyleugenol, anethole, estragole and amphotericin, respectively, showed the following MIC values: 39; 620-1250; 150-620; 310-620; 620; 620-1250 and 0.25-2.0 mg/mL. The MFC values varied from 78 to 2500 µg/mL. All tested compounds thus showed in vitro antifungal activity against Candida spp. and M. canis. Therefore, further studies should be carried out to confirm the usefulness of these alkylphenols in vivo.
Application of Optimized Vortex-Assisted Surfactant-Enhanced DLLME for Preconcentration of Thymol and Carvacrol, and Their Determination by HPLC-UV: Response Surface Methodology.

PubMed

Ghaedi, Mehrorang; Roosta, Mostafa; Khodadoust, Saeid; Daneshfar, Ali

2015-08-01

A novel vortex-assisted surfactant-enhanced dispersive liquid-liquid microextraction combined with high-performance liquid chromatography (VASEDLLME-HPLC) was developed for the determination of thymol and carvacrol (phenolic compound). In this method, the extraction solvent (CHCl3) was dispersed into the aqueous samples via a vortex agitator and addition of the surfactant (Triton X-100). The preliminary experiments were undertaken to select the best extraction solvent and surfactant. The influences of effective variables were investigated using a Plackett-Burman 2(7-4) screening design and then, the significant variables were optimized by using a central composite design combined with desirability function. Working under optimum conditions specified as: 140 µL CHCl3, 0.08% (w/v, Triton X-100), 3 min extraction time, 6 min centrifugation at 4,500 rpm, pH 7, 0.0% (w/v) NaCl permit achievement of high and reasonable linear range over 0.005-4.0 mg L(-1) with R(2) = 0.9998 (n = 10). The separation of thymol and carvacrol was achieved in <14 min using a C18 column and an isocratic binary mobile phase acetonitrile-water (55:45, v/v) with a flow rate of 1.0 mL min(-1). The VASEDLLME is applied for successful determination of carvacrol and thymol in different thyme and pharmaceutical samples with relative standard deviation <4.7% (n = 5). © The Author 2015. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.
Chemical composition, larvicidal action, and adult repellency of Thymus magnus against Aedes albopictus.

PubMed

Park, Young-Uk; Koo, Hyun-Na; Kim, Gil-Hah

2012-09-01

Thymus magnus, an endemic species, is found in the Republic of Korea. The volatile compounds extracted by SPME from T. magnus were investigated for their chemical composition and electrophysiological response against the Asian tiger mosquito, Aedes albopictus. The volatile compounds of T. magnus as determined by gas chromatography mass spectrometry were gamma-terpinene (33.0%), thymol (29.9%), beta-bisabolene (8.9%), p-cymene (8.3%), alpha-terpinene (5.0%), myrcene (4.7%), beta-caryophyllene (4.0%), alpha-thujene (2.7%), camphene (1.3%), carvacrol (1.2%), and alpha-pinene (1.1%). Among these candidates, thymol exhibited complete (100%) repellent activity against female Ae. albopictus, an effect that was confirmed through evaluating the electrophysiological response on the antenna of Ae. albopictus. The effectiveness of a binary 1:2 mixture of thymol and vanillin (0.05:0.1 microl per cm2) was found to be significantly more effective than thymol alone for a period of 120 min. In addition, thymol, alpha-terpinene, and carvacrol showed high larvicidal activity against on the third-stage larvae with LC50 values of 0.9 microl per 100 ml.
Ultrasound assisted microextraction-nano material solid phase dispersion for extraction and determination of thymol and carvacrol in pharmaceutical samples: experimental design methodology.

PubMed

Roosta, Mostafa; Ghaedi, Mehrorang; Daneshfar, Ali; Sahraei, Reza

2015-01-15

In the present study, for the first time, a new extraction method based on "ultrasound assisted microextraction-nanomaterial solid phase dispersion (UAME-NMSPD)" was developed to preconcentrate the low quantity of thymol and carvacrol in pharmaceutical samples prior to their HPLC-UV separation/determination. The analytes were accumulated on nickel sulfide nanomaterial loaded on activated carbon (NiS-NP-AC) that with more detail identified by XRD, FESEM and UV-vis technique. Central composite design (CCD) combined with desirability function (DF) was used to search for optimum operational conditions. Working under optimum conditions specified as: 10 min ultrasonic time, pH 3, 0.011 g of adsorbent and 600 μL extraction solvent) permit achievement of high and reasonable linear range over 0.005-2.0 μg mL(-1) (r(2)>0.9993) with LOD of thymol and carvacrol as 0.23 and 0.21 μg L(-1), respectively. The relative standard deviations (RSDs) were less than 4.93% (n=3). Copyright © 2014 Elsevier B.V. All rights reserved.
Molecular interactions and redox effects of carvacrol and thymol on myofibrillar proteins using a non-destructive and solvent-free methodological approach.

PubMed

Lahmar, Aida; Akcan, Tolga; Chekir-Ghedira, Leila; Estévez, Mario

2018-04-01

The present study provides molecular insight into the effect of thymol and carvacrol on the oxidative damage caused to myofibrillar proteins by a hydroxyl-radical generating system (HRGS). An innovative model system was designed, in which gels, prepared with increasing levels of myofibrillar proteins, were oxidized by a HRGS (Fe 3+ /H 2 O 2 , 60 °C and 7 days) in the presence of lipids. The molecular affinity between myofibrillar proteins and both terpenes, as well as their effect on the oxidative stability of the gel systems, were studied using a non-destructive and solvent-free procedure based on fluorescence spectroscopy. Carvacrol displayed more affinity than thymol for establishing chemical interactions with protein residues. Both terpenes exhibited a significant antioxidant potential against the generation of lipid-derived volatile carbonyls and against the formation of protein crosslinking. This procedure may be applied to meat products to assess the effectiveness of a given antioxidant additive without size reduction or sample processing. Copyright © 2018 Elsevier Ltd. All rights reserved.
Evaluation of the Antibacterial Potential of Liquid and Vapor Phase Phenolic Essential Oil Compounds against Oral Microorganisms

PubMed Central

Wu, Chi-Hao; Ko, Shun-Yao; Chen, Michael Yuanchien; Shih, Yin-Hua; Shieh, Tzong-Ming; Chuang, Li-Chuan; Wu, Ching-Yi

2016-01-01

The aim of the present study was to determine the antibacterial activities of the phenolic essential oil (EO) compounds hinokitiol, carvacrol, thymol, and menthol against oral pathogens. Aggregatibacter actinomycetemcomitans, Streptococcus mutans, Methicillin-resistant Staphylococcus aureus (MRSA), and Escherichia. coli were used in this study. The minimum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs), bacterial growth curves, temperature and pH stabilities, and synergistic effects of the liquid and vapor EO compounds were tested. The MIC/MBC of the EO compounds, ranging from the strongest to weakest, were hinokitiol (40–60 μg/mL/40-100 μg/mL), thymol (100–200 μg/mL/200-400 μg/mL), carvacrol (200–400 μg/mL/200-600 μg/mL), and menthol (500-more than 2500 μg/mL/1000-more than 2500 μg/mL). The antibacterial activities of the four EO phenolic compound based on the agar diffusion test and bacterial growth curves showed that the four EO phenolic compounds were stable under different temperatures for 24 h, but the thymol activity decreased when the temperature was higher than 80°C. The combination of liquid carvacrol with thymol did not show any synergistic effects. The activities of the vaporous carvacrol and thymol were inhibited by the presence of water. Continual violent shaking during culture enhanced the activity of menthol. Both liquid and vaporous hinokitiol were stable at different temperatures and pH conditions. The combination of vaporous hinokitiol with zinc oxide did not show synergistic effects. These results showed that the liquid and vapor phases of hinokitiol have strong anti-oral bacteria abilities. Hinokitiol has the potential to be applied in oral health care products, dental materials, and infection controls to exert antimicrobial activity. PMID:27681039
Chemical composition and anti-biofilm activity of Thymus sipyleus BOISS. subsp. sipyleus BOISS. var. davisianus RONNIGER essential oil.

PubMed

Ceylan, Ozgur; Ugur, Aysel

2015-06-01

In this study, antimicrobial and antibiofilm activities and the chemical composition of Thymus sipyleus BOISS. subsp. sipyleus BOISS. var. davisianus RONNIGER essential oil was evaluated. The essential oil was obtained by hydro-distillation and analyzed by gas chromatography-mass spectrometry. Fourteen compounds were characterized, having as major components thymol (38.31%) and carvacrol (37.95%). Minimum inhibitory concentrations (MICs) of oil and the major components were calculated by serial dilution method, and anti-biofilm effects by microplate biofilm assay against five Gram positive (Staphylococcus aureus MU 38, MU 40, MU 46, MU 47, Stahylococcus epidermidis MU 30) and five Gram negative (Pseudomonas aeruginosa MU 187, MU 188, MU 189, Pseudomonas fluorescens MU 180, MU 181) bacteria. It was found that MICs for essential oil, thymol and carvacrol were between 5 and 50 µl/ml, 0.125-0.5 µg/ml and 0.125-05 µl/ml, respectively. The results showed that doses of MIC produced a greater anti-biofilm influence than 0.5, 0.25 and 0.125 MIC. In the presence of essential oil (MIC), the mean biofilm formation value was equal to 67 ± 5.5% for P. aeruginosa MU 188, and essential oil (MIC) inhibition exceeds 60% for P. aeruginosa biofilms. The results also showed that carvacrol (MIC) was able to induce an inhibition 72.9 ± 4.1% for S.aureus (MU 40) biofilm. In addition, thymol (MIC) showed 68.6 ± 5.3% reduction in biofilm formation of P. fluorescens MU 181. This study demonstrated the antimicrobial and antibiofilm activity of T. sipyleus BOISS. subsp. sipyleus BOISS. var. davisianus RONNIGER essential oil and points out the exceptional efficiency of thymol and carvacrol, which could represent candidates in the treatment of Pseudomonas and Staphylococcus biofilms.
An Olfactory Indicator for Acid-Base Titrations.

ERIC Educational Resources Information Center

Flair, Mark N.; Setzer, William N.

1990-01-01

The use of an olfactory acid-base indicator in titrations for visually impaired students is discussed. Potential olfactory indicators include eugenol, thymol, vanillin, and thiophenol. Titrations performed with each indicator with eugenol proved to be successful. (KR)
Destruction of Opportunistic Pathogens via Polymer Nanoparticle-Mediated Release of Plant-Based Antimicrobial Payloads

PubMed Central

Amato, Dahlia N.; Amato, Douglas V.; Mavrodi, Olga V.; Braasch, Dwaine A.; Walley, Susan E.; Douglas, Jessica R.

2017-01-01

The synthesis of antimicrobial thymol/carvacrol-loaded polythioether nanoparticles (NPs) via a one-pot, solvent-free miniemulsion thiol-ene photopolymerization process is reported. The active antimicrobial agents, thymol and carvacrol, are employed as “solvents” for the thiol-ene monomer phase in the miniemulsion to enable facile high capacity loading (≈50% w/w), excellent encapsulation efficiencies (>95%), and elimination of all postpolymerization purification processes. The NPs serve as high capacity reservoirs for slow-release and delivery of thymol/carvacrol-combination payloads that exhibit inhibitory and bactericidal activity (>99.9% kill efficiency at 24 h) against gram-positive and gram-negative bacteria, including both saprophytic (Bacillus subtilis ATCC 6633 and Escherichia coli ATCC 25922) and pathogenic species (E. coli ATCC 43895, Staphylococcus aureus RN6390, and Burkholderia cenocepacia K56-2). This report is among the first to demonstrate antimicrobial efficacy of essential oil-loaded nanoparticles against B. cenocepacia – an innately resistant opportunistic pathogen commonly associated with debilitating respiratory infections in cystic fibrosis. Although a model platform, these results point to promising pathways to particle-based delivery of plant-derived extracts for a range of antimicrobial applications, including active packaging materials, topical antiseptics, and innovative therapeutics. PMID:26946055
The effect of diets supplemented with thyme essential oils and rosemary extract on the deterioration of farmed gilthead seabream (Sparus aurata) during storage on ice.

PubMed

Álvarez, A; García García, B; Jordán, M J; Martínez-Conesa, C; Hernández, M D

2012-06-01

The effect on quality were assessed for gilthead seabream fed five different diets: control (basal diet); BHT (basal diet with 200mgkg -1 of butylated hydroxytoluene); rosemary (basal diet with 600mgkg -1 of rosemary extract -Rosmarinus officinalis); carvacrol (basal diet with 500mgkg -1 of essential oil of Thymbra capitata, carvacrol chemotype); and thymol (basal diet with 500mgg -1 of essential oil of Thymus zygis, subspecies gracilis, thymol chemotype). After 18weeks of experimentation, the animals were stored on ice at 4°C for 0, 7, 14, and 21days. Physical-chemical, microbiological and sensory analyses were carried out at each sampling point to determine the degree of deterioration in the gilthead seabream. Lower indices of oxidation were observed in animals who were administered feeds supplemented with BHT, carvacrol and (to a lesser degree) rosemary. Lower bacteria counts were observed for the BHT and thymol groups, in addition to a slower deterioration in terms of sensory perception. Accordingly, the addition of natural antioxidants to the diet may have an added effect on fish quality, delaying post mortem deterioration. Copyright © 2011 Elsevier Ltd. All rights reserved.
[Inhibition of oxidation of unsaturated fatty acid methyl esters by essential oils].

PubMed

Misharina, T A; Alinkina, E S; Vorobjeva, A K; Terenina, M B; Krikunova, N I

2016-01-01

The essential oils from 16 various spice plants were studied as natural antioxidants for the inhibition of autooxidation of polyunsaturated fatty acids methyl esters isolated from linseed oil. The content of methyl oleate, methyl linoleate, and methyl linolenoate after 1, 2, and 4 months of autooxidation were used as criteria to estimate the antioxidant efficiencies of essential oils. In 4 months, 92% of the methyl linolenoate and 79% of the methyl linoleate were oxidized in a control sample of a model system. It was found that the most effective antioxidants were essential oils from clove bud, cinnamon leaves, and oregano. They inhibited autooxidation of methyl linolenoate by 76–85%. The antioxidant properties of these essential oils were due to phenols— eugenol, carvacrol, and thymol. Essential oil from coriander did not contain phenols, but it inhibited methyl linolenoate oxidation by 38%. Essential oils from thyme, savory, mace, lemon, and tea tree inhibited methyl linolenoate oxidation by 17–24%. The other essential oils had no antioxidant properties.
Induction of Fatty Acid Composition Modifications and Tolerance to Biocides in Salmonella enterica Serovar Typhimurium by Plant-Derived Terpenes▿

PubMed Central

Dubois-Brissonnet, Florence; Naïtali, Murielle; Mafu, Akier Assanta; Briandet, Romain

2011-01-01

To enhance food safety and stability, the food industry tends to use natural antimicrobials such as plant-derived compounds as an attractive alternative to chemical preservatives. Nonetheless, caution must be exercised in light of the potential for bacterial adaptation to these molecules, a phenomenon previously observed with other antimicrobials. The aim of this study was to characterize the adaptation of Salmonella enterica serovar Typhimurium to sublethal concentrations of four terpenes extracted from aromatic plants: thymol, carvacrol, citral, and eugenol, or combinations thereof. Bacterial adaptation in these conditions was demonstrated by changes in membrane fatty acid composition showing (i) limitation of the cyclization of unsaturated fatty acids to cyclopropane fatty acids when cells entered the stationary phase and (ii) bacterial membrane saturation. Furthermore, we demonstrated an increased cell resistance to the bactericidal activity of two biocides (peracetic acid and didecyl dimethyl ammonium bromide). The implications of membrane modifications in terms of hindering the penetration of antimicrobials through the bacterial membrane are discussed. PMID:21131520
Does antioxidant properties of the main component of essential oil reflect its antioxidant properties? The comparison of antioxidant properties of essential oils and their main components.

PubMed

Dawidowicz, Andrzej L; Olszowy, Małgorzata

2014-01-01

This study discusses the similarities and differences between the antioxidant activities of some essential oils: thyme (Thymus vulgaris), basil (Ocimum basilicum), peppermint (Mentha piperita), clove (Caryophyllus aromaticus), summer savory (Satureja hortensis), sage (Salvia hispanica) and lemon (Citrus limon (L.) Burm.) and of their main components (thymol or estragole or menthol or eugenol or carvacrol or camphor or limonene) estimated by using 2,2'-Diphenyl-1-picrylhydrazyl, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt and β-carotene bleaching assays. The obtained data show that the antioxidant properties of essential oil do not always depend on the antioxidant activity of its main component, and that they can be modulated by their other components. The conclusions concerning the interaction of essential oil components depend on the type of method applied for assessing the antioxidant activity. When comparing the antioxidant properties of essential oils and their main components, the concepts of synergism, antagonism and additivity are very relevant.
Larvicidal activity of essential oils extracted from commonly used herbs in Lebanon against the seaside mosquito, Ochlerotatus caspius.

PubMed

Knio, K M; Usta, J; Dagher, S; Zournajian, H; Kreydiyyeh, S

2008-03-01

This study investigates the potential of essential oils from commonly used medical and culinary herbs in Lebanon as an environmentally safe measure to control the seaside mosquito, Ochlerotatus caspius. The composition of essential oils extracted from parsley seeds and leaves, alpine thyme inflorescences, anis seeds, and coriander fruits were analyzed by GC-MS, and the major components of these oils were found to be thymol, sabinene, carvacrol, anethole, and linalool, respectively. Mosquito larvicidal assays were conducted to evaluate the LC(50) and LC(90) after 24 and 48h of the essential oils and their major constituents. All of the tested oils proved to have strong larvicidal activity (LC(50): 15-156ppm) against Oc. caspius fourth instars, with the most potent oil being thyme inflorescence extract, followed by parsley seed oil, aniseed oil, and then coriander fruit oil. Toxicity of each oil major constituent was also estimated and compared to a reported larvicidal compound, eugenol.
Bactericidal activity of glutaraldehyde-like compounds from olive products.

PubMed

Medina, Eduardo; Brenes, Manuel; García, Aranzazu; Romero, Concepción; de Castro, Antonio

2009-12-01

The bactericidal effects of several olive compounds (nonenal, oleuropein, tyrosol, the dialdehydic form of decarboxymethyl elenolic acid either free [EDA] or linked to tyrosol [TyEDA] or to hydroxytyrosol [HyEDA]), other food phenolic compounds (catechin, epicatechin, eugenol, thymol, carvacrol, and carnosic acid), and commercial disinfectants (glutaraldehyde [GTA] and ortho-phthalaldehyde [OPA]), were tested against strains of Pseudomonas fluorescens, Staphylococcus aureus, Enterococcus faecalis, and Escherichia coli. It was found that the bactericidal activities of olive GTA-like compounds (EDA, HyEDA, and TyEDA) were greater than those exerted by several food phenolic substances. Surprisingly, these olive antimicrobials were as active as the synthetic biocides GTA and OPA against the four bacteria studied. Thus, it has been proposed that the bactericidal activity of the main olive antimicrobials is primarily due to their dialdehydic structure, which is similar to that of the commercial biocides GTA and OPA. Our results clearly reveal that olive GTA-like compounds possess a strong bactericidal activity even greater than that of other food phenolic compounds or synthetic biocides.
The additive properties of Oxygen Radical Absorbance Capacity (ORAC) assay: the case of essential oils.

PubMed

Bentayeb, Karim; Vera, Paula; Rubio, Carlos; Nerín, Cristina

2014-04-01

The ORAC assay is applied to measure the antioxidant capacity of foods or dietary supplements. Sometimes, the manufacturers claim antioxidant capacities that may not correspond to the constituents of the product. These statements are sheltered by the general understanding that antioxidants might exhibit synergistic properties, but this is not necessarily true when dealing with ORAC assay values. This contribution applies the ORAC assay to measure the antioxidant capacity of ten essential oils typically added to foodstuffs: citronella, dill, basil, red thyme, thyme, rosemary, oregano, clove and cinnamon. The major components of these essential oils were twenty-one chemicals in total. After a preliminary discrimination, the antioxidant capacity of eugenol, carvacrol, thymol, α-pinene, limonene and linalool was determined. The results showed that 72-115% of the antioxidant capacity of the essential oils corresponded to the addition of the antioxidant capacity of their constituents. Thus, the ORAC assay showed additive properties. Copyright © 2013 Elsevier Ltd. All rights reserved.

Destruction of Opportunistic Pathogens via Polymer Nanoparticle-Mediated Release of Plant-Based Antimicrobial Payloads.

PubMed

Amato, Dahlia N; Amato, Douglas V; Mavrodi, Olga V; Braasch, Dwaine A; Walley, Susan E; Douglas, Jessica R; Mavrodi, Dmitri V; Patton, Derek L

2016-05-01

The synthesis of antimicrobial thymol/carvacrol-loaded polythioether nanoparticles (NPs) via a one-pot, solvent-free miniemulsion thiol-ene photopolymerization process is reported. The active antimicrobial agents, thymol and carvacrol, are employed as "solvents" for the thiol-ene monomer phase in the miniemulsion to enable facile high capacity loading (≈50% w/w), excellent encapsulation efficiencies (>95%), and elimination of all postpolymerization purification processes. The NPs serve as high capacity reservoirs for slow-release and delivery of thymol/carvacrol-combination payloads that exhibit inhibitory and bactericidal activity (>99.9% kill efficiency at 24 h) against gram-positive and gram-negative bacteria, including both saprophytic (Bacillus subtilis ATCC 6633 and Escherichia coli ATCC 25922) and pathogenic species (E. coli ATCC 43895, Staphylococcus aureus RN6390, and Burkholderia cenocepacia K56-2). This report is among the first to demonstrate antimicrobial efficacy of essential oil-loaded nanoparticles against B. cenocepacia - an innately resistant opportunistic pathogen commonly associated with debilitating respiratory infections in cystic fibrosis. Although a model platform, these results point to promising pathways to particle-based delivery of plant-derived extracts for a range of antimicrobial applications, including active packaging materials, topical antiseptics, and innovative therapeutics. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
The influence of MAP condition and active compounds on the radiosensitization of Escherichia coli and Salmonella typhi present in chicken breast

NASA Astrophysics Data System (ADS)

Lacroix, M.; Chiasson, F.

2004-09-01

The efficiency of carvacrol, thymol, trans-cinnamaldehyde (Tc) and tetrasodium pyrophosphate (Tp) on the radiosensitization of Escherichia coli and Salmonella typhi in chicken breast was determined. Chicken breast were dipped in a bath of working cultures of E. coli or S. typhi (5×10 7 CFU/ml). Active compounds were added at the concentration corresponding to {1}/{30} of the minimal inhibitory concentration. Samples were packed under air and gamma irradiation was done at doses from 0.1 to 0.7 kGy. The efficiencies of the active compounds against E. coli were 32%, 10%, 3% and 0% for thymol, Tp and carvacrol, respectively. For S. typhi, the efficiencies in the chicken breast were 47%, 19%, 17% and 11% for Tc, Tp, carvacrol and thymol, respectively. Without active compounds, D10 values were 0.145 kGy for E. coli and 0.64 kGy for S. typhi as compared to 0.098 kGy for E. coli and 0.341 kGy for S. typhi in presence of Tc. Under modified atmospheric packaging condition and in presence of Tc, D10 values were reduced to 0.046 for E. coli and to 0.110 for S. typhi.
Role of direct bioautographic method for detection of antistaphylococcal activity of essential oils.

PubMed

Horváth, Györgyi; Jámbor, Noémi; Kocsis, Erika; Böszörményi, Andrea; Lemberkovics, Eva; Héthelyi, Eva; Kovács, Krisztina; Kocsis, Béla

2011-09-01

The aim of the present study was the chemical characterization of some traditionally used and therapeutically relevant essential oils (thyme, eucalyptus, cinnamon bark, clove, and tea tree) and the optimized microbiological investigation of the effect of these oils on clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-susceptible S. aureus (MSSA). The chemical composition of the oils was analyzed by TLC, and controlled by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The antibacterial effect was investigated using a TLC-bioautographic method. Antibacterial activity of thyme, clove and cinnamon oils, as well as their main components (thymol, carvacrol, eugenol, and cinnamic aldehyde) was observed against all the bacterial strains used in this study. The essential oils of eucalyptus and tea tree showed weak activity in the bioautographic system. On the whole, the antibacterial activity of the essential oils could be related to their most abundant components, but the effect of the minor components should also be taken into consideration. Direct bioautography is more cost-effective and better in comparison with traditional microbiological laboratory methods (e.g. disc-diffusion, agar-plate technique).
Toxicological properties of thio- and alkylphenols causing flavor tainting in fish from the upper Wisconsin River

DOE Office of Scientific and Technical Information (OSTI.GOV)

Heil, T.P.; Lindsay, R.C.

1989-08-01

EC50 Microtox (5 min, 25 degrees C) assay values for 2-isopropylphenol, 3-isopropylphenol, 4-isopropylphenol, 2,4-diisopropylphenol, 2,5-diisopropylphenol 2,6-diisopropylphenol, 3,5-diisopropylphenol, carvacrol, thymol, thiophenol, and thiocresol ranged from 2 x 10(-2) mM for thymol (least toxic) to 2 x 10(-4) mM for 2,4-diisopropylphenol and 4-isopropylphenol (most toxic).
Environmental and seasonal impacts on the chemical composition of Satureja horvatii Šilić (Lamiaceae) essential oils.

PubMed

Lakušić, Branislava; Ristić, Mihailo; Slavkovska, Violeta; Milenković, Marina; Lakušić, Dmitar

2011-03-01

The chemical composition of the essential oils of Satureja horvatii Šilić from two natural habitats (Mt. Orjen and Mt. Lovćen in Montenegro) and from cultivated plants (Belgrade, Serbia) were characterized. For the latter, plants from the locus classicus, i.e., Orjenske Lokve (Mt. Orjen), were transferred to Belgrade and, after three years of cultivation, the chemical composition of their essential oils at different phenological stages was analyzed. The essential oils were obtained from the aerial parts of the plants by hydrodistillation and analyzed by GC and GC/MS. The yields and chemical compositions of the S. horvatii oils showed significant differences between the plants collected in the natural habitats and those from cultivation, as well as between the plants at different phenological stages. In the populations from the natural habitats, growing in Mediterranean conditions, the most abundant oil constituents were the phenols thymol (63.7% in the samples from Mt. Orjen) or carvacrol (68.1% in the samples from Mt. Lovćen), while the oils from the cultivated plants (Belgrade), growing in continental conditions, were dominated by linalool (up to 65.8 and 55.9% in average). The basic characteristics of the essential oil from plants at the early phenological stage (before flowering) were high percentages of linalool (37.4%), thymol (27.3%), and carvacrol (12.2%). At the stage of flowering, the percentage of linalool (56.6-57.5%) increased, while those of thymol (15.5-15.8%) and carvacrol (1.4-1.5%) significantly decreased. The essential oil of plants in the full stage of fruiting was characterized by the domination of linalool (58.4 and 65.8%) and lower percentages of thymol (7.6 and 1.3%) and carvacrol (0.7 and 0.1%). In conclusion, the oil composition of S. horvatii was found to depend on the pedoclimatic conditions of the habitat and the phenological stage of the plants. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.
In vitro antifungal activity of terpinen-4-ol, eugenol, carvone, 1,8-cineole (eucalyptol) and thymol against mycotoxigenic plant pathogens.

PubMed

Morcia, C; Malnati, M; Terzi, V

2012-01-01

The aim of this study was to examine the effect of five naturally occurring compounds from essential oils on 10 different species of mycotoxigenic fungi involved in several plant diseases. The antifungal activities of terpinen-4-ol, eugenol, carvone, 1,8-cineole (eucalyptol) and thymol were observed in vitro on Fusarium subglutinans, Fusarium cerealis, Fusarium verticillioides, Fusarium proliferatum, Fusarium oxysporum, Fusarium sporotrichioides, Aspergillus tubingensis, Aspergillus carbonarius, Alternaria alternata and Penicillium sp. The naturally occurring compounds tested showed toxic effects on in vitro mycelium growth of all fungal species but with different level of potency. The results are encouraging for further investigations of in planta antifungal activities of these essential oils components.
Use of Pinus sylvestris L. (Pinaceae), Origanum vulgare L. (Lamiaceae), and Thymus vulgaris L. (Lamiaceae) essential oils and their main components to enhance itraconazole activity against azole susceptible/not-susceptible Cryptococcus neoformans strains.

PubMed

Scalas, Daniela; Mandras, Narcisa; Roana, Janira; Tardugno, Roberta; Cuffini, Anna Maria; Ghisetti, Valeria; Benvenuti, Stefania; Tullio, Vivian

2018-05-03

Cryptococcal infections, besides being a problem for immunocompromised patients, are occasionally being a problem for immunocompetent patients. In addition, the lower susceptibility of this yeast to azoles is a growing problem in health care. To date, there are very few molecules with any activity towards Cryptococcus neoformans, leading to heightened interest in finding new alternatives or adjuvants to conventional drugs for the treatment of mycosis caused by this yeast. Since the essential oils (EOs) are considered as a potential rich source of bioactive antimicrobial compounds, we evaluated the antifungal activity of Origanum vulgare (oregano), Pinus sylvestris (pine), and Thymus vulgaris (thyme red) EOs, and their components (α-pinene, carvacrol, thymol) compared with fluconazole, itraconazole, and voriconazole, against C.neoformans clinical strains. Then, we investigated the effect of EOs and components in combination with itraconazole. EO composition was analysed by Gas chromatography-mass spectrometry (GC-MS). A broth microdilution method was used to evaluate the susceptibility of C.neoformans to azoles, EOs and components. Checkerboard tests, isobolograms and time-kill assays were carried out for combination studies. Six C.neoformans isolates were susceptible to azoles, while one C.neoformans exhibited a reduced susceptibility to all tested azole drugs. All EOs exerted a good inhibitory activity against all C.neoformans strains. Pine EO was the most effective. Among components, thymol exerted the most remarkable activity. By checkerboard testing and isobolographic analysis, combinations of itraconazole with oregano, pine, or thyme EOs, and carvacrol were found to be synergistic (FICI≤0.5) against azole susceptible C.neoformans. Regarding the azole not susceptible C.neoformans strain, the synergistic effect with itraconazole was observed with thyme EO (chemotype: thymol 26.52%; carvacrol 7.85%), and carvacrol. Time-kill assays confirmed the synergistic effects of itraconazole and oregano or thyme EO against azole susceptible C.neoformans. Binary mixtures of itraconazole/thyme EO or carvacrol yielded additive effects on the azole not susceptible C.neoformans. Our findings highlight the potential effectiveness of thyme, oregano EOs, and carvacrol as natural and cost-effective adjuvants when used in combination with itraconazole. Identification of EOs exerting these effects could be one of the feasible ways to overcome drug resistance, reducing drug concentration and side effects.
Antigenotoxic Effect Against Ultraviolet Radiation-induced DNA Damage of the Essential Oils from Lippia Species.

PubMed

Quintero Ruiz, Nathalia; Córdoba Campo, Yuri; Stashenko, Elena E; Fuentes, Jorge Luis

2017-07-01

The antigenotoxicity against ultraviolet radiation (UV)-induced DNA damage of essential oils (EO) from Lippia species was studied using SOS Chromotest. Based on the minimum concentration that significantly inhibits genotoxicity, the genoprotective potential of EO from highest to lowest was Lippia graveolens, thymol-RC ≈ Lippia origanoides, carvacrol-RC ≈ L. origanoides, thymol-RC > Lippia alba, citral-RC ≈ Lippia citriodora, citral-RC ≈ Lippia micromera, thymol-RC > L. alba, myrcenone-RC. EO from L. alba, carvone/limonene-RC, L. origanoides, α-phellandrene-RC and L. dulcis, trans-β-caryophyllene-RC did not reduce the UV genotoxicity at any of the doses tested. A gas chromatography with flame ionization detection analysis (GC-FID) was conducted to evaluate the solubility of the major EO constituents under our experimental conditions. GC-FID analysis showed that, at least partially, major EO constituents were water-soluble and therefore, they were related with the antigenotoxicity detected for EO. Constituents such as p-cymene, geraniol, carvacrol, thymol, citral and 1,8-cineole showed antigenotoxicity. The antioxidant activity of EO constituents was also determined using the oxygen radical antioxidant capacity (ORAC) assay. The results showed that the antigenotoxicity of the EO constituents was unconnected with their antioxidant activity. The antigenotoxicity to different constituent binary mixtures suggests that synergistic effects can occur in some of the studied EO. © 2017 The American Society of Photobiology.
Essential oil composition of aerial parts of Micromeria persica Boiss. from Western of Shiraz, Iran.

PubMed

Jafari, Efat; Ghanbarian, Gholamabbas; Bahmanzadegan, Atefeh

2018-04-01

Micromeria persica Boiss. is medicinal and aromatic plant, belonging to the Lamiaceae family. The chemical composition of the essential oils (EOs) from aerial parts of M. persica were extracted using hydro-distillation method and analysed using GC and GC-MS. Fifty-two compounds were identified in the EOs of aerial parts of M. persica. The main chemical compositions were n-hexadecanoic acid (14.9%), thymol (9.5%), linoleic acid (8.0%), carvacrol (5.6%), (E)-nerolidol (5.5%), linolenic acid (5.5%), α-cadinol (2.7%), linalool (2.7%), borneol (2.6%), caryophyllene oxide (2.3%) and pulegone (2.0%). Presence of borneol, thymol, carvacrol and pulegone suggests the potential of this plant as a flavouring source in the food industry, being used in perfumery and cosmetics industry, vitamin E synthesis and exhibit strong fungicidal, antibacterial and antimicrobial activities.
Inhibitory effects of selected Turkish spices and oregano components on some foodborne fungi.

PubMed

Akgül, A; Kivanç, M

1988-05-01

The inhibitory effects of 10 selected Turkish spices, oregano essential oil, thymol and carvacrol towards growth of 9 foodborne fungi were investigated in culture media with pH 3.5 and 5.5. The antifungal effects of sodium chloride, sorbic acid and sodium benzoate and the combined use of oregano with sodium chloride were also tested under the same conditions for comparison. Of the spices tested, only sodium chloride were also tested under the same conditions for comparison. Of the spices tested, only oregano at 1.0, 1.5, 2.0% (w/v) levels showed effect on all fungi. 8% (w/v) sodium chloride was less effective than oregano. Oregano essential oil, thymol or carvacrol at concentrations of 0.025% and 0.05% completely inhibited the growth of all fungi, showing greater inhibition than sorbic acid at the same concentrations. The combined use of oregano and sodium chloride exhibited a synergistic antifungal effect.
Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae).

PubMed

Traboulsi, Abdallah F; Taoubi, K; el-Haj, Samih; Bessiere, J M; Rammal, Salma

2002-05-01

The insecticidal activities of essential oil extracts from leaves and flowers of aromatic plants against fourth-instar larvae of the mosquito Culex pipiens molestus Forskal were determined. Extracts of Myrtus communis L were found to be the most toxic, followed by those of Origanum syriacum L, Mentha microcorphylla Koch, Pistacia lentiscus L and Lavandula stoechas L with LC50 values of 16, 36, 39, 70 and 89 mg litre-1, respectively. Over 20 major components were identified in extracts from each plant species. Eight pure components (1,8-cineole, menthone, linalool, terpineol, carvacrol, thymol, (1S)-(-)-alpha-pinene and (1R)-(+)-alpha-pinene) were tested against the larvae. Thymol, carvacrol, (1R)-(+)-alpha-pinene and (1S)-(-)-alpha-pinene were the most toxic (LC50 = 36-49 mg litre-1), while menthone, 1,8-cineole, linalool and terpineol (LC50 = 156-194 mg litre-1) were less toxic.
Antimicrobial activity of the essential oil from Lippia sidoides, carvacrol and thymol against oral pathogens.

PubMed

Botelho, M A; Nogueira, N A P; Bastos, G M; Fonseca, S G C; Lemos, T L G; Matos, F J A; Montenegro, D; Heukelbach, J; Rao, V S; Brito, G A C

2007-03-01

Dental caries and periodontal disease are associated with oral pathogens. Several plant derivatives have been evaluated with respect to their antimicrobial effects against such pathogenic microorganisms. Lippia sidoides Cham (Verbenaceae), popularly known as "Alecrim-pimenta" is a typical shrub commonly found in the Northeast of Brazil. Many plant species belonging to the genus Lippia yield very fragrant essential oils of potential economic value which are used by the industry for the commercial production of perfumes, creams, lotions, and deodorants. Since the leaves of L. sidoides are also extensively used in popular medicine for the treatment of skin wounds and cuts, the objective of the present study was to evaluate the composition and antimicrobial activity of L. sidoides essential oil. The essential oil was obtained by hydro-distillation and analyzed by GC-MS. Twelve compounds were characterized, having as major constituents thymol (56.7%) and carvacrol (16.7%). The antimicrobial activity of the oil and the major components was tested against cariogenic bacterial species of the genus Streptococcus as well as Candida albicans using the broth dilution and disk diffusion assays. The essential oil and its major components thymol and carvacrol exhibited potent antimicrobial activity against the organisms tested with minimum inhibitory concentrations ranging from 0.625 to 10.0 mg/mL. The most sensitive microorganisms were C. albicans and Streptococcus mutans. The essential oil of L. sidoides and its major components exert promising antimicrobial effects against oral pathogens and suggest its likely usefulness to combat oral microbial growth.
Improvement of the overall quality of table grapes stored under modified atmosphere packaging in combination with natural antimicrobial compounds.

PubMed

Guillén, F; Zapata, P J; Martínez-Romero, D; Castillo, S; Serrano, M; Valero, D

2007-04-01

Consumers demand new means of preservation with absence of chemicals. In this work a package was developed (thermosealed baskets) with grapes wrapped with 2 distinct films (M and P) with different permeability (medium and high, respectively) without or with the addition of a mixture of eugenol, thymol, and carvacrol. Table grapes stored on air (control) lost their quality attributes very rapidly, manifested by accelerated weight loss, color changes, softening, and increase in soluble solids concentration and titratable acidity ratio (SSC/TA). The use of modified atmosphere packaging (MAP) alone retarded these changes, the effects being significantly greater when essential oils were added (especially for M film), although atmospheric composition was not affected by incorporating essential oils. In addition, microbial counts (molds and yeasts and mesophilic aerobics) were drastically decreased and accompanied by lower occurrence of berry decay. Although slight odor was detected after opening the packages, absence of the typical flavor of these compounds was found by trained panelists after tasting the berries. Thus, with this safe, simple, and innovative technology, the overall quality (sensory and safety) could be improved and considered as a toll alternative to the use of synthetic fungicides.
Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.

PubMed

Ntalli, Nikoletta G; Ferrari, Federico; Giannakou, Ioannis; Menkissoglu-Spiroudi, Urania

2010-07-14

Eight essential oils (EOs) as well as 13 single terpenes were studied for their nematicidal activity against Meloidogyne incognita , for three immersion periods (24, 48, and 96 h). The EOs were isolated from eight Greek Lamiaceae species: Melissa officinalis , Sideritis clandestina , Origanum dictamnus , Ocimum basilicum , Mentha pulegium , Origanum vulgare , Vitex agnus castus , and Salvia officinalis . The EOs nematicidal activity was correlated to their chemical composition as well as to the pure terpenes' activity tested individually. Clear dose and time response relationships were established. The EOs of O. vulgare, O. dictamnus, M. pulegium, and M. officinalis exhibited high nematicidal activity against M. incognita, and the EC(50) values (96 h) were calculated at 1.55, 1.72, 3.15, and 6.15 muL/mL, respectively. The activity of the nematicidal terpenes was found to decrease in the order l-carvone, pulegone, trans-anethole, geraniol, eugenol, carvacrol, thymol, terpinen-4-ol, and the respective EC(50) values (24 h) were calculated in the range of 115-392 mug/mL. Terpenes tested individually were more active than as components in EO, implementing antagonistic action.
Evaluation of three headspace sorptive extraction coatings for the determination of volatile terpenes in honey using gas chromatography-mass spectrometry.

PubMed

Cacho, J I; Campillo, N; Viñas, P; Hernández-Córdoba, M

2015-06-19

Headspace sorptive extraction (HSSE) was used to preconcentrate seven monoterpenes (eucalyptol, linalool, menthol, geraniol, carvacrol, thymol and eugenol) for separation by gas chromatography and mass spectrometry (GC-MS). Three commercially available coatings for the stir bars, namely Polydimethylsiloxane (PDMS), polyacrilate (PA) and Ethylene glycol-silicone (EG-Silicone), were tested, and the influential parameters both in the adsorption and the thermal desorption steps were optimized. PDMS provided the best sensitivity for linalool, geraniol, menthol and eucalyptol, whereas EG-Silicone was best for extracting the phenolic monoterpenes studied. Considering the average obtained slopes from all compounds, PDMS pointed as the best option, and the analytical characteristics for the HSSE-TD-GC-MS method using this coating were obtained. Quantification of the samples was carried out by matrix-matched calibration using a synthetic honey. Detection limits ranged between 0.007 and 0.032 ng g(-1), depending on the compound. Twelve honey samples of different floral origins were analyzed using the HSSE-GC-MS method, the analytes being detected at concentrations up to 64 ng g(-1). Copyright © 2015 Elsevier B.V. All rights reserved.
[Studies on antimicrobial activity of extracts from thyme].

PubMed

Fan, M; Chen, J

2001-08-01

The extracts from thyme by water and ethanol, thyme essential oil, thymol and carvacrol were used as antimicrobial agents in this paper. The results show that all antimicrobial agents used have strong inhibition activity against Staphalococcus aureus, Bacillus subtilis, Escherichia coli.
Use of enhanced nisin derivatives in combination with food-grade oils or citric acid to control Cronobacter sakazakii and Escherichia coli O157:H7.

PubMed

Campion, Alicia; Morrissey, Ruth; Field, Des; Cotter, Paul D; Hill, Colin; Ross, R Paul

2017-08-01

Cronobacter sakazakii and Escherichia coli O157:H7 are well known food-borne pathogens that can cause severe disease. The identification of new alternatives to heating to control these pathogens in foods, while reducing the impact on organoleptic properties and nutritional value, is highly desirable. In this study, nisin and its bioengineered variants, nisin V and nisin S29A, are used alone, or in combination with plant essential oils (thymol, carvacrol and trans-cinnamaldehyde) or citric acid, with a view to controlling C. sakazakii and E. coli O157:H7 in laboratory-based assays and model food systems. The use of nisin variants (30 μM) with low concentrations of thymol (0.015%), carvacrol (0.03%) and trans-cinnamaldehyde (0.035%) resulted in extended lag phases of growth compared to those for corresponding nisin A-essential oil combinations. Furthermore, nisin variants (60 μM) used in combination with carvacrol (0.03%) significantly reduced viable counts of E. coli O157:H7 (3-log) and C. sakazakii (4-log) compared to nisin A-carvacrol treatment. Importantly, this increased effectiveness translated into food. More specifically, sub-inhibitory concentrations of nisin variants and carvacrol caused complete inactivation of E. coli O157:H7 in apple juice within 3 h at room temperature compared to that of the equivalent nisin A combination. Furthermore, combinations of commercial Nisaplin and the food additive citric acid reduced C. sakazakii numbers markedly in infant formula within the same 3 h period. These results highlight the potential benefits of combining nisin and variants thereof with carvacrol and/or citric acid for the inhibition of Gram negative food-borne pathogens. Copyright © 2017 Elsevier Ltd. All rights reserved.
Antimicrobial and antioxidant activity of the essential oil and methanol extracts of Thymus pectinatus Fisch. et Mey. Var. pectinatus (Lamiaceae).

PubMed

Vardar-Unlü, Gülhan; Candan, Ferda; Sökmen, Atalay; Daferera, Dimitra; Polissiou, Moschos; Sökmen, Münevver; Dönmez, Erol; Tepe, Bektaş

2003-01-01

The essential oil, obtained by using a Clevenger distillation apparatus, and water-soluble (polar) and water-insoluble (nonpolar) subfractions of the methanol extract of Thymus pectinatus Fisch. et Mey. var. pectinatus were assayed for their antimicrobial and antioxidant properties. No (or slight) antimicrobial activity was observed when the subfractions were tested, whereas the essential oil showed strong antimicrobial activity against all microorganisms tested. Antioxidant activities of the polar subfraction and the essential oil were evaluated using 2,2-diphenyl-1-picrylhydrazyl, hydroxyl radical, superoxide radical scavenging, and lipid peroxidation assays. The essential oil, in particular, and the polar subfraction of the methanol extract showed antioxidant activity. The essential oil was analyzed by GC/MS, and 24 compounds, representing 99.6% of the essential oil, were identified: thymol, gamma-terpinene, p-cymene, carvacrol, and borneol were the main components. An antimicrobial activity test carried out with fractions of the essential oil showed that the activity was mainly observed in those fractions containing thymol, in particular, and carvacrol. The activity was, therefore, attributed to the presence of these compounds. Other constituents of the essential oil, such as borneol, gamma-terpinene, and p-cymene, could be also taken into account for their possible synergistic or antagonistic effects. On the other hand, thymol and carvacrol were individually found to possess weaker antioxidant activity than the crude oil itself, indicating that other constituents of the essential oil may contribute to the antioxidant activity observed. In conclusion, the results presented here show that T. pectinatus essential oil could be considered as a natural antimicrobial and antioxidant source.
Green drugs in the fight against Anisakis simplex-larvicidal activity and acetylcholinesterase inhibition of Origanum compactum essential oil.

PubMed

López, Víctor; Cascella, María; Benelli, Giovanni; Maggi, Filippo; Gómez-Rincón, Carlota

2018-03-01

Anisakiasis is a fish-borne parasitic disease caused by the consumption of raw or undercooked fish, as well as cephalopods, contaminated by third instar larvae (L3) of species belonging to the genus Anisakis (Anisakidae). Origanum compactum is a small herbaceous aromatic plant endemic to Spain and Morocco. In Morocco, the plant is used under infusion to treat heart diseases and intestinal pains or as preservative for foodstuffs. This is the first time that the O. compactum essential oil is tested against the parasitic nematode Anisakis simplex. The phytochemical analysis by GC-MS revealed carvacrol (50.3%) and thymol (14.8%) as the major oil constituents. The essential oil and its major constituents carvacrol and thymol were tested against A. simplex L3 larvae isolated from blue whiting fish (Micromesistius poutassou). A. simplex mortality (%) after 24 and 48 h of treatment at 1 μl/ml was 100%, with a low LD 50 compared with other essential oils and extracts, and the penetration in the agar assay was also reduced, if compared with control wells. The oil, as well as its major constituents, demonstrated a dose-dependent larvicidal activity. Inhibition of the enzyme acetylcholinesterase through a colorimetric assay in 96-well plates was used to elucidate the pharmacological mechanism as this enzyme plays a key role in nematodes neuromuscular function. Interestingly, O. compactum essential oil, carvacrol and thymol inhibited the enzyme, confirming that this could be one of the mechanisms involved in the anthelmintic activity. To the best of our knowledge, this is the first time that O. compactum essential oil is reported as a larvicidal agent against A. simplex L3 larvae.
The Essential Oil from Origanum vulgare L. and Its Individual Constituents Carvacrol and Thymol Enhance the Effect of Tetracycline against Staphylococcus aureus.

PubMed

Cirino, Isis Caroline S; Menezes-Silva, Suellen Maria P; Silva, Helena Tainá D; de Souza, Evandro Leite; Siqueira-Júnior, José P

2014-01-01

In an ongoing project to evaluate essential oils as modulators of antibiotic resistance, the essential oil from Origanum vulgare L. (OVEO), as well as its individual constituents carvacrol (CAR) and thymol (THY), were investigated using Staphylococcus aureus strains possessing efflux mechanisms of resistance to norfloxacin, erythromycin and tetracycline. The minimum inhibitory concentration (MIC) values of the antibiotics were determined by agar dilution method, in the absence and in the presence of subinhibitory concentrations of OVEO, CAR or THY. Along with relevant antistaphylococcal activity, OVEO, CAR and THY modulated the activity of tetracycline, i.e. in combination with antibiotics a reduction in the MIC was observed (up to fourfold). The results presented here represent, as far as we know, the first report of OVEO, CAR and THY as putative efflux pump inhibitors. Broadly, these findings indicate that essential oils could serve as potential sources of compounds capable of modulating drug resistance. © 2015 S. Karger AG, Basel.

Thymol, thyme, and other plant sources: Health and potential uses.

PubMed

Salehi, Bahare; Mishra, Abhay Prakash; Shukla, Ila; Sharifi-Rad, Mehdi; Contreras, María Del Mar; Segura-Carretero, Antonio; Fathi, Hannane; Nasrabadi, Nafiseh Nasri; Kobarfard, Farzad; Sharifi-Rad, Javad

2018-05-22

Thymol is a naturally occurring phenol monoterpene derivative of cymene and isomer of carvacrol. Thymol (10-64%) is one of the major constituent of essential oils of thyme (Thymus vulgaris L., Lamiaceae), a medicinal plant with several therapeutic properties. This plant, native to Mediterranean regions, is commonly used as a culinary herb and also with a long history of use for different medicinal purposes. Nowadays, thymol and thyme present a wide range of functional possibilities in pharmacy, food, and cosmetic industry. The interest in the formulation of pharmaceuticals, nutraceuticals, and cosmeceuticals based on thymol is due to several studies that have evaluated the potential therapeutic uses of this compound for the treatment of disorders affecting the respiratory, nervous, and cardiovascular systems. Moreover, this compound also exhibits antimicrobial, antioxidant, anticarcinogenesis, anti-inflammatory, and antispasmodic activities, as well as a potential as a growth enhancer and immunomodulator. In the present review, these bioactivities have been covered because some of them can contribute to explain the ethnopharmacology of thymol and its main source, T. vulgaris. Other important aspects about thymol are discussed: its toxicity and bioavailability, metabolism, and distribution in animals and humans. Copyright © 2018 John Wiley & Sons, Ltd.
Efficacies of Nisin A and Nisin V Semipurified Preparations Alone and in Combination with Plant Essential Oils for Controlling Listeria monocytogenes

PubMed Central

Daly, Karen; O'Connor, Paula M.; Cotter, Paul D.; Ross, R. Paul

2015-01-01

The food-borne pathogenic bacterium Listeria is known for relatively low morbidity and high mortality rates, reaching up to 25 to 30%. Listeria is a hardy organism, and its control in foods represents a significant challenge. Many naturally occurring compounds, including the bacteriocin nisin and a number of plant essential oils, have been widely studied and are reported to be effective as antimicrobial agents against spoilage and pathogenic microorganisms. The aim of this study was to investigate the ability of semipurified preparations (SPP) containing either nisin A or an enhanced bioengineered derivative, nisin V, alone and in combination with low concentrations of the essential oils thymol, carvacrol, and trans-cinnamaldehyde, to control Listeria monocytogenes in both laboratory media and model food systems. Combinations of nisin V-containing SPP (25 μg/ml) with thymol (0.02%), carvacrol (0.02%), or cinnamaldehyde (0.02%) produced a significantly longer lag phase than any of the essential oil-nisin A combinations. In addition, the log reduction in cell counts achieved by the nisin V-carvacrol or nisin V-cinnamaldehyde combinations was twice that of the equivalent nisin A-essential oil treatment. Significantly, this enhanced activity was validated in model food systems against L. monocytogenes strains of food origin. We conclude that the fermentate form of nisin V in combination with carvacrol and cinnamaldehyde offers significant advantages as a novel, natural, and effective means to enhance food safety by inhibiting food-borne pathogens such as L. monocytogenes. PMID:25662980
Chemical composition and antimicrobial activity of Satureja hortensis and Trachyspermum copticum essential oil

PubMed Central

Mahboubi, M; Kazempour, N

2011-01-01

Background and Objectives The aim of this study was to evaluate the chemical composition and antimicrobial activity of Satureja hortensis and Trachyspermum copticum essential oils against different kinds of microorganisms in vitro. Material and Methods The antimicrobial activity was evaluated by micro broth dilution assay and the chemical composition of essential oils was analyzed by GC and GC/MS. Results Thymol, p-cymene, γ-terpinene and carvacrol were the main components of S. hortensis oil while thymol, γ-terpinene, and o-cymene were the major components of T. copticum oil. Two essential oils exhibited strong antimicrobial activity but the antimicrobial activity of T. copticum oil was higher than that of S. hortensis oil. Conclusion Thymol as a main component of oils plays an important role in antimicrobial activity. PMID:22530088
Essential oils have different effects on human pathogenic and commensal bacteria in mixed faecal fermentations compared with pure cultures.

PubMed

Thapa, Dinesh; Louis, Petra; Losa, Riccardo; Zweifel, Béatrice; Wallace, R John

2015-02-01

A static batch culture system inoculated with human faeces was used to determine the influence of essential oil compounds (EOCs) on mixed faecal microbiota. Bacteria were quantified using quantitative PCR of 16S rRNA genes. Incubation for 24 h of diluted faeces from six individuals caused enrichment of Bifidobacterium spp., but proportions of other major groups were unaffected. Thymol and geraniol at 500 p.p.m. suppressed total bacteria, resulting in minimal fermentation. Thymol at 100 p.p.m. had no effect, nor did eugenol or nerolidol at 100 or 500 p.p.m. except for a slight suppression of Eubacterium hallii. Methyl isoeugenol at 100 or 500 p.p.m. suppressed the growth of total bacteria, accompanied by a large fall in the molar proportion of propionate formed. The relative abundance of Faecalibacterium prausnitzii was unaffected except with thymol at 500 p.p.m. The ability of EOCs to control numbers of the pathogen Clostridium difficile was investigated in a separate experiment, in which the faecal suspensions were amended by the addition of pure culture of C. difficile. Numbers of C. difficile were suppressed by thymol and methyl isoeugenol at 500 p.p.m. and to a lesser extent at 100 p.p.m. Eugenol and geraniol gave rather similar suppression of C. difficile numbers at both 100 and 500 p.p.m. Nerolidol had no significant effect. It was concluded from these and previous pure-culture experiments that thymol and geraniol at around 100 p.p.m. could be effective in suppressing pathogens in the small intestine, with no concern for beneficial commensal colonic bacteria in the distal gut. © 2015 The Authors.
Antimicrobial activities of commercial essential oils and their components against food-borne pathogens and food spoilage bacteria

PubMed Central

Mith, Hasika; Duré, Rémi; Delcenserie, Véronique; Zhiri, Abdesselam; Daube, Georges; Clinquart, Antoine

2014-01-01

This study was undertaken to determine the in vitro antimicrobial activities of 15 commercial essential oils and their main components in order to pre-select candidates for potential application in highly perishable food preservation. The antibacterial effects against food-borne pathogenic bacteria (Listeria monocytogenes, Salmonella Typhimurium, and enterohemorrhagic Escherichia coli O157:H7) and food spoilage bacteria (Brochothrix thermosphacta and Pseudomonas fluorescens) were tested using paper disk diffusion method, followed by determination of minimum inhibitory (MIC) and bactericidal (MBC) concentrations. Most of the tested essential oils exhibited antimicrobial activity against all tested bacteria, except galangal oil. The essential oils of cinnamon, oregano, and thyme showed strong antimicrobial activities with MIC ≥ 0.125 μL/mL and MBC ≥ 0.25 μL/mL. Among tested bacteria, P. fluorescens was the most resistant to selected essential oils with MICs and MBCs of 1 μL/mL. The results suggest that the activity of the essential oils of cinnamon, oregano, thyme, and clove can be attributed to the existence mostly of cinnamaldehyde, carvacrol, thymol, and eugenol, which appear to possess similar activities against all the tested bacteria. These materials could be served as an important natural alternative to prevent bacterial growth in food products. PMID:25473498
Combined Toxicity of Three Essential Oils Against Aedes aegypti (Diptera: Culicidae) Larvae.

PubMed

Muturi, Ephantus J; Ramirez, Jose L; Doll, Kenneth M; Bowman, Michael J

2017-11-07

Essential oils are potential alternatives to synthetic insecticides because they have low mammalian toxicity, degrade rapidly in the environment, and possess complex mixtures of bioactive constituents with multi-modal activity against the target insect populations. Twenty-one essential oils were initially screened for their toxicity against Aedes aegypti (L.) larvae and three out of the seven most toxic essential oils (Manuka, oregano, and clove bud essential oils) were examined for their chemical composition and combined toxicity against Ae. aegypti larvae. Manuka essential oil interacted synergistically with oregano essential oil and antagonistically with clove bud essential oil. GC-MS analysis revealed the presence of 21 components in Manuka essential oil and three components each in oregano and clove bud essential oils. Eugenol (84.9%) and eugenol acetate (9.6%) were the principal constituents in clove bud essential oil while carvacrol (75.8%) and m-isopropyltoluene (15.5%) were the major constituents in oregano essential oil. The major constituents in Manuka essential oil were calamenene (20%) and 3-dodecyl-furandione (11.4%). Manuka essential oil interacted synergistically with eugenol acetate and antagonistically with eugenol, suggesting that eugenol was a major contributor to the antagonistic interaction between Manuka and clove bud essential oils. In addition, Manuka interacted synergistically with carvacrol suggesting its contribution to the synergistic interaction between Manuka and oregano essential oils. These findings provide novel insights that can be used to develop new and safer alternatives to synthetic insecticides. Published by Oxford University Press on behalf of Entomological Society of America 2017. This work is written by (a) US Government employee(s) and is in the public domain in the US.
Augmenting the activity of monoterpenoid phenols against fungal pathogens using 2-hydroxy-4-methoxybenzaldehyde that target cell wall integrity

USDA-ARS?s Scientific Manuscript database

The aim of this study was to identify benzaldehydes to which the fungal cell wall integrity signaling mutants showed increased sensitivity. These compounds could then function as chemosensitizing agents in combination with monoterpenoid phenols, such as carvacrol or thymol, to enhance antifungal act...
Nanoemulsions of thymol and eugenol co-emulsified by lauric arginate and lecithin.

PubMed

Ma, Qiumin; Davidson, P Michael; Zhong, Qixin

2016-09-01

Lauric arginate (LAE) is a cationic surfactant with excellent antimicrobial activities. To incorporate essential oil components (EOCs) in aqueous systems, properties of EOC nanoemulsions prepared with a LAE and lecithin mixture were studied. The LAE-lecithin mixture resulted in stable translucent nanoemulsions of thymol and eugenol with spherical droplets smaller than 100nm, contrasting with the turbid emulsions prepared with individual emulsifiers. Zeta-potential data suggested the formation of LAE-lecithin complexes probably through hydrophobic interaction. Negligible difference was observed for antimicrobial activities of nanoemulsions and LAE in tryptic soy broth. In 2% reduced fat milk, nanoemulsions showed similar antilisterial activities compared to free LAE in inhibiting Listeria monocytogenes, but was less effective against Escherichia coli O157:H7 than free LAE, which was correlated with the availability of LAE as observed in release kinetics. Therefore, mixing LAE with lecithin improved the physical properties of EOC nanoemulsions but did not improve antimicrobial activities, especially against Gram-negative bacteria. Copyright © 2016 Elsevier Ltd. All rights reserved.
Calcium dependence of eugenol tolerance and toxicity in Saccharomyces cerevisiae.

PubMed

Roberts, Stephen K; McAinsh, Martin; Cantopher, Hanna; Sandison, Sean

2014-01-01

Eugenol is a plant-derived phenolic compound which has recognised therapeutical potential as an antifungal agent. However little is known of either its fungicidal activity or the mechanisms employed by fungi to tolerate eugenol toxicity. A better exploitation of eugenol as a therapeutic agent will therefore depend on addressing this knowledge gap. Eugenol initiates increases in cytosolic Ca2+ in Saccharomyces cerevisiae which is partly dependent on the plasma membrane calcium channel, Cch1p. However, it is unclear whether a toxic cytosolic Ca2+elevation mediates the fungicidal activity of eugenol. In the present study, no significant difference in yeast survival was observed following transient eugenol treatment in the presence or absence of extracellular Ca2+. Furthermore, using yeast expressing apoaequorin to report cytosolic Ca2+ and a range of eugenol derivatives, antifungal activity did not appear to be coupled to Ca2+ influx or cytosolic Ca2+ elevation. Taken together, these results suggest that eugenol toxicity is not dependent on a toxic influx of Ca2+. In contrast, careful control of extracellular Ca2+ (using EGTA or BAPTA) revealed that tolerance of yeast to eugenol depended on Ca2+ influx via Cch1p. These findings expose significant differences between the antifungal activity of eugenol and that of azoles, amiodarone and carvacrol. This study highlights the potential to use eugenol in combination with other antifungal agents that exhibit differing modes of action as antifungal agents to combat drug resistant infections.
Trans-cinnamaldehyde, carvacrol, and eugenol reduce Campylobacter jejuni colonization factors and expression of virulence genes in vitro

USDA-ARS?s Scientific Manuscript database

Campylobacter jejuni is a major foodborne pathogen that causes severe gastroenteritis in humans characterized by fever, diarrhea and abdominal cramps. In the human gut, Campylobacter adheres and invades the intestinal epithelium followed by cytolethal distending toxin mediated cell death, and enteri...
Acaricidal efficacies of Lippia gracilis essential oil and its phytochemicals against organophosphate-resistant and susceptible strains of Rhipicephalus (Boophilus) microplus

USDA-ARS?s Scientific Manuscript database

Plant-derived natural products can serve as an alternative to synthetic compounds for control of ticks of veterinary and medical importance. Lippia gracilis is an aromatic plant that produces essential oil with high content of carvacrol and thymol monoterpenes. These monoterpenes have high acaricida...
The inhibitory effects of essential oil constituents against germination, outgrowth and vegetative growth of spores of Clostridium perfringens type A in laboratory medium and chicken meat.

PubMed

Alanazi, Saud; Alnoman, Maryam; Banawas, Saeed; Saito, Ryoichi; Sarker, Mahfuzur R

2018-08-01

C. perfringens type A is the causative agent of C. perfringens type A food poisoning (FP) and non-food-borne (NFB) human gastrointestinal diseases. Due to its ability to form highly heat-resistant spores, it is of great interest to develop strategies alternative to thermal processing to inactivate C. perfrinegens. Thus, in this study we evaluated the inhibitory effects of essential oil constituents (EOCs) (cinnamaldehyde, eugenol, allyl isothiocyanate (AITC), and carvacrol) against germination, outgrowth and vegetative growth of spores of C. perfringens FP and NFB disease isolates in laboratory medium and chicken meat. The cinnamaldehyde, eugenol and carvacrol, but not AITC, all at 0.05-0.1%, inhibited the germination of spores of all tested C. perfringens isolates in Tripticase-glucose-yeast extract (TGY) medium. Furthermore, all tested EOCs at 0.05-0.1% arrested the outgrowth and vegetative growth of C. perfringens spores in TGY, with AITC and carvacrol being the most effective. However, among four tested EOCs, only AITC (at 0.5%-2.0%) was able to inhibit the growth of C. perfringens spores in chicken meat and no such inhibitory effect was observed even with a 10-fold higher concentration (5%) of carvacrol. In conclusion, our current work identified AITC as an effective EOC to control spores and vegetative cells of C. perfringens isolates in laboratory medium and chicken meat. Further studies on evaluating the effectiveness of different combination of EOCs against C. perfringens spore growth in different meat products should establish an effective use of EOCs to control the risk of C. perfringens-mediated illnesses. Copyright © 2018 Elsevier Ltd. All rights reserved.
Bio-based phenolic-branched-chain fatty acid isomers synthesized from vegetable oils and natural monophenols using modified h+-ferrierite zeolite

USDA-ARS?s Scientific Manuscript database

A new group of phenolic branched-chain fatty acids (n-PBC-FA), hybrid molecules of natural monophenols (i.e., thymol, carvacrol and creosote) and mixed fatty acid (i.e., derived from soybean and safflower oils), were efficiently produced through a process known as arylation. The reaction involves a...
Chemical composition and assessment of larvicidal and repellent capacity of 14 Lamiaceae essential oils against Aedes albopictus.

PubMed

Giatropoulos, Athanassios; Kimbaris, Athanasios; Michaelakis, Αntonios; Papachristos, Dimitrios P; Polissiou, Moschos G; Emmanouel, Nickolaos

2018-06-01

In the current laboratory study, 14 essential oils (EOs) derived from 12 Lamiaceae plant species and their major components were screened for their larvicidal and repellent properties against Aedes albopictus, an invasive mosquito species of great medical importance. The results of toxicity bioassays revealed that the EOs from Thymus vulgaris, Ocimum basilicum, Origanum dictamnus, Origanum majorana, and Origanum vulgare, as well as their major components (terpenes), namely thymol, carvacrol, p-cymene, and γ-terpinene exerted the highest larvicidal effect. Essential oils from Mellisa officinalis, Origanum dictamus, Mentha spicata (chem. piperitenone epoxide), Origanum majorana, and Satureja thymbra were the most potent repellents, with the last two assigned as the best ones. Among the terpenes tested, piperitenone epoxide, carvacrol, thymol, and piperitenone provided the highest level of protection against Ae. albopictus adults. Chemical analysis revealed the presence of a high number of terpenes in the EOs, while in most cases, the biological action of the tested EOs and their major components was in consistency. The most effective EOs and terpenes that were identified through the current laboratory bioassays could be used as alternative agents to control larvae and repel adults of Ae. albopictus.
Teriyaki sauce with carvacrol or thymol effectively controls Escherichia coli O157:H7, Listeria monocytogenes, Salmonella Typhimurium, and indigenous flora in marinated beef and marinade.

PubMed

Moon, Hyeree; Kim, Nam Hee; Kim, Soon Han; Kim, Younghoon; Ryu, Jee Hoon; Rhee, Min Suk

2017-07-01

An effective bactericidal cold-marinating method for beef products is described, exploiting the synergism between soy sauce and natural compounds (carvacrol, CV or thymol, TM) to reduce microbiological risks. Beef slices inoculated with Escherichia coli O157:H7, Listeria monocytogenes, and Salmonella Typhimurium (3.1-3.5logCFU/g) were marinated in a teriyaki sauce with or without CV and TM (0.3 and 0.5%). After 1, 3, and 7days at 4°C, indigenous microflora population, color, lipid oxidation, marinade uptake, and pH of marinated beef and leftover marinade samples were examined. Teriyaki sauce alone did not reduce or inhibit any of the target pathogens or indigenous bacteria, while 0.5% CV- or TM-containing teriyaki sauce inactivated all inocula without recovery within 7days (p<0.05). The pathogens relocated from the beef into the leftover marinade (3.0-3.4logCFU/mL) were also completely inactivated. The treatment inhibited growth of indigenous aerobic bacteria (p<0.05) and inactivated coliform bacteria. Physicochemical parameters were not significantly affected (p>0.05). Copyright © 2017 Elsevier Ltd. All rights reserved.
Insecticidal Properties of Essential Oils and Some of Their Constituents on the Turkestan Cockroach (Blattodea: Blattidae).

PubMed

Gaire, Sudip; O'Connell, Mary; Holguin, Francisco O; Amatya, Anup; Bundy, Scott; Romero, Alvaro

2017-04-01

The Turkestan cockroach, Blatta lateralis (Walker), has become the most important peridomestic species in urban areas of the Southwestern United States. The aim of this study was to evaluate the use of botanical compounds to control this urban pest. We tested the acute toxicity and repellency of six botanical constituents and three essential oils on Turkestan cockroach nymphs. Chemical composition of the essential oils was also determined. Topical and fumigant assays with nymphs showed that thymol was the most toxic essential oil constituent, with a LD50 of 0.34 mg/nymph and a LC50 of 27.6 mg/liter air, respectively. Contact toxicity was also observed in assays with trans-Cinnamaldehyde, eugenol, geraniol, methyl eugenol, and p-Cymene. Methyl eugenol and geraniol had limited fumigant toxicity. The essential oils from red thyme, clove bud, and Java citronella exhibited toxicity against nymphs. Cockroaches avoided fresh dry residues of thymol and essential oils. Chemical analysis of the essential oils confirmed high contents of effective essential oil constituents. Our results demonstrated that essential oils and some of their constituents have potential as eco-friendly insecticides for the management of Turkestan cockroaches. © The Authors 2017. Published by Oxford University Press on behalf of Entomological Society of America. All rights reserved. For Permissions, please email: journals.permissions@oup.com.
Essential oils of culinary herbs and spices display agonist and antagonist activities at human aryl hydrocarbon receptor AhR.

PubMed

Bartoňková, Iveta; Dvořák, Zdeněk

2018-01-01

Essential oils (EOs) of culinary herbs and spices are used to flavor, color and preserve foods and drinks. Dietary intake of EOs is significant, deserving an attention of toxicologists. We examined the effects of 31 EOs of culinary herbs and spices on the transcriptional activity of human aryl hydrocarbon receptor (AhR), which is a pivotal xenobiotic sensor, having also multiple roles in human physiology. Tested EOs were sorted out into AhR-inactive ones (14 EOs) and AhR-active ones, including full agonists (cumin, jasmine, vanilla, bay leaf), partial agonists (cloves, dill, thyme, nutmeg, oregano) and antagonists (tarragon, caraway, turmeric, lovage, fennel, spearmint, star anise, anise). Major constituents (>10%) of AhR-active EOs were studied in more detail. We identified AhR partial agonists (carvacrol, ligustilide, eugenol, eugenyl acetate, thymol, ar-turmerone) and antagonists (trans-anethole, butylidine phtalide, R/S-carvones, p-cymene), which account for AhR-mediated activities of EOs of fennel, anise, star anise, caraway, spearmint, tarragon, cloves, dill, turmeric, lovage, thyme and oregano. We also show that AhR-mediated effects of some individual constituents of EOs differ from those manifested in mixtures. In conclusion, EOs of culinary herbs and spices are agonists and antagonists of human AhR, implying a potential for food-drug interactions and interference with endocrine pathways. Copyright © 2017 Elsevier Ltd. All rights reserved.
Herbs and spices: characterization and quantitation of biologically-active markers for routine quality control by multiple headspace solid-phase microextraction combined with separative or non-separative analysis.

PubMed

Sgorbini, Barbara; Bicchi, Carlo; Cagliero, Cecilia; Cordero, Chiara; Liberto, Erica; Rubiolo, Patrizia

2015-01-09

Herbs and spices are used worldwide as food flavoring, thus determination of their identity, origin, and quality is mandatory for safe human consumption. An analysis strategy based on separative (HS-SPME-GC-MS) and non-separative (HS-SPME-MS) approaches is proposed for the volatile fraction of herbs and spices, for quality control and to quantify the aromatic markers with a single analysis directly on the plant material as such. Eight-to-ten lots of each of the following herbs/spices were considered: cloves (Syzygium aromaticum (L.) Merr. & Perry), American peppertree (Schinus molle L.), black pepper and white pepper (Piper nigrum L.), rosemary (Rosmarinus officinalis L.), sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.). Homogeneity, origin, and chemotypes of the investigated lots of each herb/spice were defined by fingerprinting, through statistical elaboration with principal component analysis (PCA). Characterizing aromatic markers were directly quantified on the solid matrix through multiple headspace extraction-HS-SPME (MHS-SPME). Reliable results were obtained with both separative and non-separative methods (where the latter were applicable); the two were in full agreement, RSD% ranging from 1.8 to 7.7% for eugenol in cloves, 2.2-18.4% for carvacrol+thymol in thyme, and 3.1-16.8% for thujones in sage. Copyright © 2014 Elsevier B.V. All rights reserved.
Plant essential oils and allied volatile fractions as multifunctional additives in meat and fish-based food products: a review.

PubMed

Patel, Seema

2015-01-01

Essential oils are concentrated aromatic volatile compounds derived from botanicals by distillation or mechanical pressing. They play multiple, crucial roles as antioxidants, food pathogen inhibitors, shelf-life enhancers, texture promoters, organoleptic agents and toxicity-reducing agents. For their versatility, they appear promising as food preservatives. Several research findings in recent times have validated their potential as functional ingredients in meat and fish processing. Among the assortment of bioactive compounds in the essential oils, p-cymene, thymol, eugenol, carvacrol, isothiocyanate, cinnamaldehyde, cuminaldehyde, linalool, 1,8-cineol, α-pinene, α-terpineol, γ-terpinene, citral and methyl chavicol are most familiar. These terpenes (monoterpenes and sesquiterpenes) and phenolics (alcohols, esters, aldehydes and ketones) have been extracted from culinary herbs such as oregano, rosemary, basil, coriander, cumin, cinnamon, mint, sage and lavender as well as from trees such as myrtle, fir and eucalyptus. This review presents essential oils as alternatives to conventional chemical additives. Their synergistic actions with modified air packaging, irradiation, edible films, bacteriocins and plant byproducts are discussed. The decisive roles of metabolic engineering, microwave technology and metabolomics in quality and quantity augmentation of essential oil are briefly mooted. The limitations encountered and strategies to overcome them have been illuminated to pave way for their enhanced popularisation. The literature has been mined from scientific databases such as Pubmed, Pubchem, Scopus and SciFinder.
Clove and rosemary essential oils and encapsuled active principles (eugenol, thymol and vanillin blend) on meat quality of feedlot-finished heifers.

PubMed

de Oliveira Monteschio, Jéssica; de Souza, Kennyson Alves; Vital, Ana Carolina Pelaes; Guerrero, Ana; Valero, Maribel Velandia; Kempinski, Emília Maria Barbosa Carvalho; Barcelos, Vinícius Cunha; Nascimento, Karina Favoreto; do Prado, Ivanor Nunes

2017-08-01

Forty Nellore heifers were fed (73days) with different diets: with or without essential oils (clove and/or rosemary essential oil) and/or active principle blend (eugenol, thymol and vanillin). The pH, fat thickness, marbling, muscle area and water losses (thawing and drip) were evaluated 24h post mortem on the Longissimus thoracis, and the effects of aging (14days) was evaluated on the meat cooking losses, color, texture and lipid oxidation. Antioxidant activity was also evaluated. Treatments had no effect (P>0.05) on pH, fat thickness, marbling, muscle area, thawing and drip losses. However, treatments affected (P<0.05) cooking losses, color, texture and lipid oxidation. The diets with essential oil and the active principle blend reduced the lipid oxidation and reduced the color losses in relation to control diet. Aging affected (P<0.05) texture and lipid oxidation. The essential oil and active principles or its blend have potential use in animal feed aiming to maintain/improve meat quality during shelf-life. Copyright © 2017. Published by Elsevier Ltd.

Anti-oxidant activity and major chemical component analyses of twenty-six commercially available essential oils.

PubMed

Wang, Hsiao-Fen; Yih, Kuang-Hway; Yang, Chao-Hsun; Huang, Keh-Feng

2017-10-01

This study analyzed 26 commercially available essential oils and their major chemical components to determine their antioxidant activity levels by measuring their total phenolic content (TPC), reducing power (RP), β-carotene bleaching (BCB) activity, trolox equivalent antioxidant capacity (TEAC), and 1,1-diphenyl-2-picrylhydrazyl free radical scavenging (DFRS) ability. The clove bud and thyme borneol essential oils had the highest RP, BCB activity levels, and TPC values among the 26 commercial essential oils. Furthermore, of the 26 essential oils, the clove bud and ylang ylang complete essential oils had the highest TEAC values, and the clove bud and jasmine absolute essential oils had the highest DFRS ability. At a concentration of 2.5 mg/mL, the clove bud and thyme borneol essential oils had RP and BCB activity levels of 94.56% ± 0.06% and 24.64% ± 0.03% and 94.58% ± 0.01% and 89.33% ± 0.09%, respectively. At a concentration of 1 mg/mL, the clove bud and thyme borneol essential oils showed TPC values of 220.00 ± 0.01 and 69.05 ± 0.01 mg/g relative to gallic acid equivalents, respectively, and the clove bud and ylang ylang complete essential oils had TEAC values of 809.00 ± 0.01 and 432.33 ± 0.01 μM, respectively. The clove bud and jasmine absolute essential oils showed DFRS abilities of 94.13% ± 0.01% and 78.62% ± 0.01%, respectively. Phenolic compounds of the clove bud, thyme borneol and jasmine absolute essential oils were eugenol (76.08%), thymol (14.36%) and carvacrol (12.33%), and eugenol (0.87%), respectively. The phenolic compounds in essential oils were positively correlated with the RP, BCB activity, TPC, TEAC, and DFRS ability. Copyright © 2017. Published by Elsevier B.V.
Microencapsulated sorbic acid and pure botanicals affect Salmonella Typhimurium shedding in pigs: a close-up look from weaning to slaughter in controlled and field conditions

USDA-ARS?s Scientific Manuscript database

The aim of this study was to assess the efficacy of a combination of sorbic acid, thymol, and carvacrol in reducing the prevalence and shedding of Salmonella Typhimurium in pigs either in a controlled challenge environment or in a production setting. In the first study, 24 weaned piglets were dist...
Antibacterial effects of the essential oils of commonly consumed medicinal herbs using an in vitro model.

PubMed

Soković, Marina; Glamočlija, Jasmina; Marin, Petar D; Brkić, Dejan; van Griensven, Leo J L D

2010-10-27

The chemical composition and antibacterial activity of essential oils from 10 commonly consumed herbs: Citrus aurantium, C. limon, Lavandula angustifolia, Matricaria chamomilla, Mentha piperita, M. spicata, Ocimum basilicum, Origanum vulgare, Thymus vulgaris and Salvia officinalis have been determined. The antibacterial activity of these oils and their main components; i.e. camphor, carvacrol, 1,8-cineole, linalool, linalyl acetate, limonene, menthol, a-pinene, b-pinene, and thymol were assayed against the human pathogenic bacteria Bacillus subtilis, Enterobacter cloacae, Escherichia coli O157:H7, Micrococcus flavus, Proteus mirabilis, Pseudomonas aeruginosa, Salmonella enteritidis, S. epidermidis, S. typhimurium, and Staphylococcus aureus. The highest and broadest activity was shown by O. vulgare oil. Carvacrol had the highest antibacterial activity among the tested components.
Impact of Moderate Heat, Carvacrol, and Thymol Treatments on the Viability, Injury, and Stress Response of Listeria monocytogenes

PubMed Central

Guevara, L.; Antolinos, V.; Palop, A.; Periago, P. M.

2015-01-01

The microbial safety and stability of minimally processed foods are based on the application of combined preservative factors. Since microorganisms are able to develop adaptive networks to survive under conditions of stress, food safety may be affected, and therefore understanding of stress adaptive mechanisms plays a key role in designing safe food processing conditions. In the present study, the viability and the sublethal injury of Listeria monocytogenes exposed to moderate heat (55°C) and/or essential oil compounds (carvacrol and thymol, 0.3 mM) treatments were studied. Synergistic effects were obtained when combining mild heat (55°C) with one or both essential oil compounds, leading to inactivation kinetics values three to four times lower than when using heat alone. All the treatments applied caused some injury in the population. The injury levels ranged from around 20% of the surviving population under the mildest conditions to more than 99.99% under the most stringent conditions. Protein extracts of cells exposed to these treatments were analysed by two-dimensional gel electrophoresis. The results obtained revealed that stressed cells exhibited differential protein expression to control cells. The proteins upregulated under these stressing conditions were implicated, among other functions, in stress response, metabolism, and protein refolding. PMID:26539510
Antimicrobial, antioxidant and sensory features of eugenol, carvacrol and trans-anethole in active packaging for organic ready-to-eat iceberg lettuce.

PubMed

Wieczyńska, Justyna; Cavoski, Ivana

2018-09-01

In this study, bio-based emitting sachets containing eugenol (EUG), carvacrol (CAR) and trans-anethole (ANT) were inserted into cellulose (CE) and polypropylene (PP) pillow packages of organic ready-to-eat (RTE) iceberg lettuce to investigate their functional features. EUG, CAR and ANT sachets in CE; and CAR in PP packages showed antimicrobial activities against coliforms (Δlog CFU g -1 of -1.38, -0.91, -0.93 and -0.93, respectively). EUG and ANT sachets in both packages reduced discoloration (ΔE of 9.5, 1.8, 9.4 and 5.6, respectively). ANT in both, and EUG only in PP packages induced biosynthesis of caffeoyl derivatives (C a T A , D i C a T A , D i C a Q A ), total phenolics and antioxidant activity (FRAP). Also, ANT and EUG in both packages improved overall freshness and odor. Principal component analysis separated ANT and EUG from CAR in both packages. The Pearson correlation confirmed that overall quality improvements were more pronounced by ANT inside the packages in comparison to EUG and CAR. Copyright © 2018 Elsevier Ltd. All rights reserved.
Bacterial susceptibility to and chemical composition of essential oils from Thymus kotschyanus and Thymus persicus.

PubMed

Rasooli, Iraj; Mirmostafa, Seyed Akbar

2003-04-09

Susceptibility of Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumonia, and Pseudomonas aeroginosa to the essential oils extracted from two varieties of Thyme, i.e., Thymus kotschyanus Boiss. and Hohen. and Thymus persicus L. at preflowering and flowering stages were studied. The disk diffusion method was used to evaluate the zone of microbial growth inhibition at various concentrations of the oils. Minimal inhibitory concentration and minimal bactericidal concentration of the oils were determined and compared with each other. The oils from the above plants were found to be strongly bactericidal with that of T. kotschyanus being more effective. T. kotschyanusand T. persicus oils analyzed by gas chromatography (GC) and GC/mass spectrometry (MS) lead to identification of 33 and 26 components, respectively. The profile of the oil components from T. persicuswas similar to that of T. kotschyanus in almost all of the compounds but at different concentrations. The major components of T. kotschyanus oil before and at the flowering stages were carvacrol (35.06, 22.75%), thymol (26.60, 16.52%), gamma-terpinene (7.81, 0.34%), gamma-terpinene (4.34, 0%), borneol (2.29, 4.52%), myrcene (0.26, 12.65%), thymolquinone (0, 11.39%), nerol (0, 6.10%), and beta-caryophyllene (0, 5.54%), respectively, and those of T. persicus at the same stages were carvacrol (38.96, 27.07%), thymol (6.48, 11.86%), P-cymene (7.51, 10.16%), gamma-terpineol (0, 9.51%), nerol (15.66, 9.41%), gamma-terpinene (6.11, 6.51%), and thymol acetate (5.29, 5.30%), respectively. The contribution of oil components to its antibacterial property is discussed. High aromatic compound content of the phenol-rich oils seems to account for strong antibacterial activity.
Composition of the essential oils of three Uzbek Scutellaria species (Lamiaceae) and their antioxidant activities.

PubMed

Mamadalieva, Nilufar Zokirjonovna; Sharopov, Farukh; Satyal, Prabodh; Azimova, Shahnoz Sadykovna; Wink, Michael

2017-05-01

The chemical composition of the essential oils obtained from aerial parts of Scutellaria immaculata Nevski ex Juz., Scutellaria ramosissima M. Pop. and Scutellaria schachristanica Juz. (Lamiaceae) growing wild in Uzbekistan was analysed by GC and GC-MS. The main constituents of the essential oils from S. immaculata were acetophenone (30.39%), eugenol (20.61%), thymol (10.04%) and linalool (6.92%), whereas constituents of the essential oils fromS. schachristanica were acetophenone (34.74%), linalool (26.98%) and eugenol (20.67%). The S. ramosissima oil is dominated by germacrene D (23.96%), β-caryophyllene (11.09%), linalool (9.63%) and hexadecanoic acid (8.34%). The essential oils of Scutellaria species exhibited weaker antioxidant effects in DPPH, ABTS and FRAP assays. In FRAP assay, only eugenol exhibited a substantial reducing power IC 50 = 2476.92 ± 15.8 (mM Fe(II)/g).
The synergistic effects of insecticidal essential oils and piperonyl butoxide on biotransformational enzyme activities in Aedes aegypti (Diptera: Culicidae).

PubMed

Waliwitiya, Ranil; Nicholson, Russell A; Kennedy, Christopher J; Lowenberger, Carl A

2012-05-01

The biochemical mechanisms underlying the increased toxicity of several plant essential oils (thymol, eugenol, pulegone, terpineol, and citronellal) against fourth instar of Aedes aegypti L. when exposed simultaneously with piperonyl butoxide (PBO) were examined. Whole body biotransformational enzyme activities including cytochrome P450-mediated oxidation (ethoxyresorufin O-dethylase [EROD]), glutathione S-transferase (GST), and beta-esterase activity were measured in control, essential oil-exposed only (single chemical), and essential oil + PBO (10 mg/liter) exposed larvae. At high concentrations, thymol, eugenol, pulegone, and citronellal alone reduced EROD activity by 5-25% 16 h postexposure. Terpineol at 10 mg/liter increased EROD activity by 5 +/- 1.8% over controls. The essential oils alone reduced GST activity by 3-20% but PBO exposure alone did not significantly affect the activity of any of the measured enzymes. All essential oils in combination with PBO reduced EROD activity by 58-76% and reduced GST activity by 3-85% at 16 h postexposure. This study indicates a synergistic interaction between essential oils and PBO in inhibiting the cytochrome P450 and GST detoxification enzymes in Ae. aegypti.
Gontscharovia popovii, a new source of carvacrol, its polyphenolic constituents, essential oil analysis, total phenolic content and antioxidant activity.

PubMed

Zareiyan, Faraneh; Rowshan, Vahid; Bahmanzadegan, Atefeh; Hatami, Ahmad

2017-09-28

The experiment was carried out using the shadow-dried aerial parts including leaves and shoots of Gontscharovia popovii collected in Fars province in order to investigate the polyphenolic compositions, antioxidant activity, total phenolic content and essential oil constituents. The result showed IC 50 of 395.77 μg mL -1 and total phenolic content of about 20.01 mg g -1 gallic acid equivalent dry weight. It also showed a wild range of polyphenols such as; Gallic acid, catechin, chloregenic acid, rutin, vanillin, trans-Ferulic acid, sinapic acid, coumarin, hesperedin, quercetin, hesperetin, eugenol and carvacrol as the main detected polyphenols. Some major compounds were also detected through essential oil analysis, such as; 76.7% carvacrol, 4.25% γ-Terpinene, 3.8% p-Cymene and 2.4% (E)-Caryophyllene. Qualitative and quantitative analyses of chemical compounds of G. popovii was performed using HPLC, GC, GC/MS and microplate reader.
Microencapsulation, Chemical Characterization, and Antimicrobial Activity of Mexican (Lippia graveolens H.B.K.) and European (Origanum vulgare L.) Oregano Essential Oils

PubMed Central

Regalado-González, Carlos; Vázquez-Landaverde, Pedro; Guerrero-Legarreta, Isabel; García-Almendárez, Blanca E.

2014-01-01

The effect of solvent polarity (methanol and pentane) on the chemical composition of hydrodistilled essential oils (EO's) of Lippia graveolens H.B.K. (MXO) and Origanum vulgare L. (EUO) was studied by GC-MS. Composition of modified starch microencapsulated EO's was conducted by headspace-solid-phase microextraction (HS-SPME). The antimicrobial activity of free and microencapsulated EO's was evaluated. They were tested against Salmonella sp., Brochothrix thermosphacta, Pseudomonas fragi, Lactobacillus plantarum, and Micrococcus luteus. Thymol and carvacrol were among the main components of EO's and their free and microencapsulated inhibitory activity was tested against M. luteus, showing an additive combined effect. Chemical composition of EO's varied according to the solvent used for GC analysis and to volatile fraction as evaluated by HS-SPME. Thymol (both solvents) was the main component in essential oil of MXO, while carvacrol was the main component of the volatile fraction. EUO showed α-pinene (methanol) and γ-terpinene (pentane) as major constituents, the latter being the main component of the volatile fraction. EO's showed good stability after 3 months storage at 4°C, where antimicrobial activity of microencapsulated EO's remained the same, while free EO's decreased 41% (MXO) and 67% (EUO) from initial activity. Microencapsulation retains most antimicrobial activity and improves stability of EO's from oregano. PMID:25177730
Influence of carvacrol and thymol on the physiological attributes, enterotoxin production and surface characteristics of Staphylococcus aureus strains isolated from foods

PubMed Central

Souza, E.L.; Oliveira, C.E.V.; Stamford, T.L.M.; Conceição, M.L.; Neto, N.J. Gomes

2013-01-01

This study evaluated the influence of the phenolic compounds carvacrol (CAR) and thymol (THY) on some physiological characteristics and on the modulation of the secretion of some staphylococcal virulence factors, that is, coagulase and enterotoxin. This study also investigated possible mechanisms for the establishment of the anti-staphylococcal activity of these compounds. Sublethal concentrations (0.3 and 0.15 μL/mL) of CAR and THY inhibited the activity of the enzymes coagulase and lipase and led to a decrease in salt tolerance. At the tested sublethal concentrations, both CAR and THY led to a total suppression of enterotoxin production. The loss of a 260-nm-absorbing material and an efflux of potassium ions occurred immediately after the addition of CAR and THY at 0.6 and 1.2 μL/mL and increased up to 120 min of exposure. Electron microscopy of cells exposed to CAR and THY (0.6 μL/mL) revealed that individual cells appeared to be deformed, with projections of cellular material. The observations of leakage of cellular material and an altered cell surface suggest that gross damage to a cell’s cytoplasmic membrane, which results in a disruption in protein secretion, could be responsible for the anti-staphylococcal properties of CAR and THY. PMID:24159280
Microencapsulation, chemical characterization, and antimicrobial activity of Mexican (Lippia graveolens H.B.K.) and European (Origanum vulgare L.) oregano essential oils.

PubMed

Hernández-Hernández, Elvia; Regalado-González, Carlos; Vázquez-Landaverde, Pedro; Guerrero-Legarreta, Isabel; García-Almendárez, Blanca E

2014-01-01

The effect of solvent polarity (methanol and pentane) on the chemical composition of hydrodistilled essential oils (EO's) of Lippia graveolens H.B.K. (MXO) and Origanum vulgare L. (EUO) was studied by GC-MS. Composition of modified starch microencapsulated EO's was conducted by headspace-solid-phase microextraction (HS-SPME). The antimicrobial activity of free and microencapsulated EO's was evaluated. They were tested against Salmonella sp., Brochothrix thermosphacta, Pseudomonas fragi, Lactobacillus plantarum, and Micrococcus luteus. Thymol and carvacrol were among the main components of EO's and their free and microencapsulated inhibitory activity was tested against M. luteus, showing an additive combined effect. Chemical composition of EO's varied according to the solvent used for GC analysis and to volatile fraction as evaluated by HS-SPME. Thymol (both solvents) was the main component in essential oil of MXO, while carvacrol was the main component of the volatile fraction. EUO showed α-pinene (methanol) and γ-terpinene (pentane) as major constituents, the latter being the main component of the volatile fraction. EO's showed good stability after 3 months storage at 4°C, where antimicrobial activity of microencapsulated EO's remained the same, while free EO's decreased 41% (MXO) and 67% (EUO) from initial activity. Microencapsulation retains most antimicrobial activity and improves stability of EO's from oregano.
Plant extracts affect in vitro rumen microbial fermentation.

PubMed

Busquet, M; Calsamiglia, S; Ferret, A; Kamel, C

2006-02-01

Different doses of 12 plant extracts and 6 secondary plant metabolites were incubated for 24 h in diluted ruminal fluid with a 50:50 forage:concentrate diet. Treatments were: control (no additive), plant extracts (anise oil, cade oil, capsicum oil, cinnamon oil, clove bud oil, dill oil, fenugreek, garlic oil, ginger oil, oregano oil, tea tree oil, and yucca), and secondary plant metabolites (anethol, benzyl salicylate, carvacrol, carvone, cinnamaldehyde, and eugenol). Each treatment was supplied at 3, 30, 300, and 3,000 mg/L of culture fluid. At 3,000 mg/L, most treatments decreased total volatile fatty acid concentration, but cade oil, capsicum oil, dill oil, fenugreek, ginger oil, and yucca had no effect. Different doses of anethol, anise oil, carvone, and tea tree oil decreased the proportion of acetate and propionate, which suggests that these compounds may not be nutritionally beneficial to dairy cattle. Garlic oil (300 and 3,000 mg/L) and benzyl salicylate (300 and 3,000 mg/L) reduced acetate and increased propionate and butyrate proportions, suggesting that methane production was inhibited. At 3,000 mg/L, capsicum oil, carvacrol, carvone, cinnamaldehyde, cinnamon oil, clove bud oil, eugenol, fenugreek, and oregano oil resulted in a 30 to 50% reduction in ammonia N concentration. Careful selection and combination of these extracts may allow the manipulation of rumen microbial fermentation.
Plant phenolic volatiles inhibit quorum sensing in pectobacteria and reduce their virulence by potential binding to ExpI and ExpR proteins

NASA Astrophysics Data System (ADS)

Joshi, Janak Raj; Khazanov, Netaly; Senderowitz, Hanoch; Burdman, Saul; Lipsky, Alexander; Yedidia, Iris

2016-12-01

Quorum sensing (QS) is a population density-dependent regulatory system in bacteria that couples gene expression to cell density through accumulation of diffusible signaling molecules. Pectobacteria are causal agents of soft rot disease in a range of economically important crops. They rely on QS to coordinate their main virulence factor, production of plant cell wall degrading enzymes (PCWDEs). Plants have evolved an array of antimicrobial compounds to anticipate and cope with pathogens, of which essential oils (EOs) are widely recognized. Here, volatile EOs, carvacrol and eugenol, were shown to specifically interfere with QS, the master regulator of virulence in pectobacteria, resulting in strong inhibition of QS genes, biofilm formation and PCWDEs, thereby leading to impaired infection. Accumulation of the signal molecule N-acylhomoserine lactone declined upon treatment with EOs, suggesting direct interaction of EOs with either homoserine lactone synthase (ExpI) or with the regulatory protein (ExpR). Homology models of both proteins were constructed and docking simulations were performed to test the above hypotheses. The resulting binding modes and docking scores of carvacrol and eugenol support potential binding to ExpI/ExpR, with stronger interactions than previously known inhibitors of both proteins. The results demonstrate the potential involvement of phytochemicals in the control of Pectobacterium.
Activity of essential oils and individual components against acetyl- and butyrylcholinesterase.

PubMed

Orhan, Ilkay; Kartal, Murat; Kan, Yüksel; Sener, Bilge

2008-01-01

We have tested acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of nineteen essential oils obtained from cultivated plants, namely one from Anethum graveolens L. (organic fertilizer), two from Foeniculum vulgare Mill. collected at fully-mature and flowering stages (organic fertilizer), two from Melissa officinalis L. (cultivated using organic and chemical fertilizers), two from Mentha piperita L. and M. spicata L. (organic fertilizer), two from Lavandula officinalis Chaix ex Villars (cultivated using organic and chemical fertilizers), two from Ocimum basilicum L. (green and purple-leaf varieties cultivated using only organic fertilizer), four from Origanum onites L., O. vulgare L., O. munitiflorum Hausskn., and O. majorana L. (cultivated using organic fertilizer), two from Salvia sclarea L. (organic and chemical fertilizers), one from S. officinalis L. (organic fertilizer), and one from Satureja cuneifolia Ten. (organic fertilizer) by a spectrophotometric method of Ellman using ELISA microplate-reader at 1 mg/ml concentration. In addition, a number of single components widely encountered in most of the essential oils [gamma-terpinene, 4-allyl anisole, (-)-carvone, dihydrocarvone, (-)-phencone, cuminyl alcohol, cumol, 4-isopropyl benzaldehyde, trans-anethole, camphene, iso-borneol, (-)-borneol, L-bornyl acetate, 2-decanol, 2-heptanol, methyl-heptanol, farnesol, nerol, iso-pulegol, 1,8-cineole, citral, citronellal, citronellol, geraniol, linalool, alpha-pinene, beta-pinene, piperitone, iso-menthone, menthofurane, linalyl oxide, linalyl ester, geranyl ester, carvacrol, thymol, menthol, vanilline, and eugenol] was also screened for the same activity in the same manner. Almost all of the essential oils showed a very high inhibitory activity (over 80%) against both enzymes, whereas the single components were not as active as the essential oils.
Development of LLDPE based active nanocomposite films with nanoclays impregnated with volatile compounds.

PubMed

Tornuk, Fatih; Sagdic, Osman; Hancer, Mehmet; Yetim, Hasan

2018-05-01

In this study, a novel procedure was performed for grafting of nanoclays (montmorillonite (MMT) and halloysite (HNT)) with essential oil constituents (thymol (THY), eugenol (EUG) and carvacrol (CRV)) using Tween 80 as surfactant and then the nanoclay particles were incorporated into LLDPE pellets (5 wt%) to produce active nanocomposite films using a twin screw extruder. The resulting nanocomposite films were analyzed for antimicrobial and antioxidant capacity as well as thickness, mechanical, color, barrier, thermal properties and surface morphology and molecular composition. Release of the active compounds from the films at the refrigerated and room temperature conditions were also tested. The results showed that the films had strong in vitro antibacterial activity against pathogenic bacteria (Salmonella Typhimurium, Escherichia coli O157:H7, Listeria monocytogenes, Staphylococcus aureus and Bacillus cereus) while their effect against lactic acid bacteria (Lactobacillus rhamnosus and Lb. casei) was limited. The lowest and highest DPPH scavenging ability levels were 65.59% and % 87.92, belonged to THY-MMT and EUG-MMT, respectively. Release of active compounds at 24 °C was much more rapid than at 4 °C. CRV-HNT and THY-HNT provided slower release than the other films. SEM results showed that nanoclays were uniformly dispersed in the polymer matrix with exceptional agglomerates. Incorporation of the active nanoclays significantly (P > 0.05) improved tensile strength and elongation of the films. The results confirmed that LLDPE based active nanocomposite films could be successfully produced due to its good interaction with MMT and HNT, activated with THY, EUG and CRV. Copyright © 2018 Elsevier Ltd. All rights reserved.
Extraction of the essential oil from endemic Origanum bilgeri P.H.Davis with two different methods: comparison of the oil composition and antibacterial activity.

PubMed

Sözmen, Fazli; Uysal, Burcu; Köse, Elif Odabaş; Aktaş, Ozgür; Cinbilgel, Ilker; Oksal, Birsen S

2012-07-01

The antibacterial activity and chemical composition of the essential oils (EOs) isolated from Origanum bilgeri P.H.Davis by two different extraction methods, i.e., hydrodistillation (HD) and solvent-free microwave extraction (SFME), were examined. This endemic Origanum species had shown very good antibacterial activity. The composition of the O. bilgeri EOs obtained by SFME and HD was investigated by GC/MS analysis. The main components of the oils obtained by both methods were carvacrol (90.20-84.30%), p-cymene (3.40-5.85%), γ-terpinene (0.47-1.20%), and thymol (0.69-1.08%). The EO isolation by SFME offered many important advantages, including a higher extraction yield, a shorter extraction time, and a higher content of the active component carvacrol. The carvacrol-rich oils obtained by both HD and SFME showed a good antibacterial activity. The largest inhibition zones were observed for the O. bilgeri EO obtained by SFME. Our study suggests that O. bilgeri EO has the potential to be used as preventative against bacterial contamination in many foods, instead of the common synthetic antimicrobial products. Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich.
Does the essential oil of Lippia sidoides Cham. (pepper-rosmarin) affect its endophytic microbial community?

PubMed

da Silva, Thais Freitas; Vollú, Renata Estebanez; Jurelevicius, Diogo; Alviano, Daniela Sales; Alviano, Celuta Sales; Blank, Arie Fitzgerald; Seldin, Lucy

2013-02-07

Lippia sidoides Cham., also known as pepper-rosmarin, produces an essential oil in its leaves that is currently used by the pharmaceutical, perfumery and cosmetic industries for its antimicrobial and aromatic properties. Because of the antimicrobial compounds (mainly thymol and carvacrol) found in the essential oil, we believe that the endophytic microorganisms found in L. sidoides are selected to live in different parts of the plant. In this study, the endophytic microbial communities from the stems and leaves of four L. sidoides genotypes were determined using cultivation-dependent and cultivation-independent approaches. In total, 145 endophytic bacterial strains were isolated and further grouped using either ERIC-PCR or BOX-PCR, resulting in 76 groups composed of different genera predominantly belonging to the Gammaproteobacteria. The endophytic microbial diversity was also analyzed by PCR-DGGE using 16S rRNA-based universal and group-specific primers for total bacteria, Alphaproteobacteria, Betaproteobacteria and Actinobacteria and 18S rRNA-based primers for fungi. PCR-DGGE profile analysis and principal component analysis showed that the total bacteria, Alphaproteobacteria, Betaproteobacteria and fungi were influenced not only by the location within the plant (leaf vs. stem) but also by the presence of the main components of the L. sidoides essential oil (thymol and/or carvacrol) in the leaves. However, the same could not be observed within the Actinobacteria. The data presented here are the first step to begin shedding light on the impact of the essential oil in the endophytic microorganisms in pepper-rosmarin.
Antibacterial and efflux pump inhibitors of thymol and carvacrol against food-borne pathogens.

PubMed

Miladi, Hanene; Zmantar, Tarek; Chaabouni, Yassine; Fedhila, Kais; Bakhrouf, Amina; Mahdouani, Kacem; Chaieb, Kamel

2016-10-01

In this study thymol (THY) and carvacrol (CAR), two monoterpenic phenol produced by various aromatic plants, was tested for their antibacterial and efflux pump inhibitors potencies against a panel of clinical and foodborne pathogenes. Our results demonstrated a substantial susceptibility of the tested bacteria toward THY and CAR. Especially, THY displayed a strong inhibitory activity (MIC's values ranged from 32 to 64 μg/mL) against the majority of the tested strains compared to CAR. Moreover, a significant reduction in MIC's of TET and benzalkonium chloride (QAC) were noticed when tested in combinations with THY and CAR. Their synergic effect was more significant in the case of THY which resulted a reduction of MIC's values of TET (2-8 fold) and QAC (2-8 fold). We noted also that THY and CAR inhibited the ethidium bromide (EtBr) cell efflux in a concentration-dependent manner. The rate of EtBr accumulation in food-borne pathogen was enhanced with THY and CAR (0, 250 and 500 μg/mL). The lowest concentration causing 50% of EtBr efflux inhibition (IC 50) was noticed in Salmonella enteritidis (1129) at 150 μg/mL of THY and 190 μg/mL of CAR respectively. These findings indicate that THY and CAR may serve as potential sources of efflux pump inhibitor in food-borne pathogens. Copyright © 2016 Elsevier Ltd. All rights reserved.
Synergistic and antagonistic interactions of terpenes against Meloidogyne incognita and the nematicidal activity of essential oils from seven plants indigenous to Greece.

PubMed

Ntalli, Nikoletta G; Ferrari, Federico; Giannakou, Ioannis; Menkissoglu-Spiroudi, Urania

2011-03-01

Biorational means for phytonematode control were studied within the context of an increasingly ecofriendly pest management global approach. The nematicidal activity and the chemical composition of essential oils (EOs) isolated from seven plants grown in Greece and ten selected compounds extracted from them against second-stage juveniles (J2) of Meloidogyne incognita (Kof. & White) Chitwood were evaluated using juvenile paralysis experiments. Additionally, synergistic and antagonistic interactions between nematicidal terpenes were studied using an effect addition model, with the comparison made at one concentration level. The 96 h EC(50) values of Foeniculum vulgare Mill., Pimpinella anisum L., Eucalyptus meliodora A Cunn ex Schauer and Pistacia terebinthus L. were 231, 269, 807 and 1116 µg mL(-1) , respectively, in an immersion bioassay. Benzaldehyde (9 µg mL(-1) ) was the most toxic compound, followed by γ-eudesmol (50 µg mL(-1) ) and estragole (180 µg mL(-1) ), based on 96 h EC(50) values. The most potent terpene pairs between which synergistic actions were found, in decreasing order, were: trans-anethole/geraniol, trans-anethole/eugenol, carvacrol/eugenol and geraniol/carvacrol. This is the first report on the activity of F. vulgare, P. anisum, E. meliodora and P. terebinthus, and additionally on synergistic/antagonistic nematicidal terpene interactions, against M. incognita, providing alternative methods for nematode control. Copyright © 2010 Society of Chemical Industry.

Determination of some volatile compounds in alcoholic beverage by headspace solid-phase microextraction gas chromatography - mass spectrometry

NASA Astrophysics Data System (ADS)

Schmutzer, G.; Avram, V.; Feher, I.; David, L.; Moldovan, Z.

2012-02-01

The volatile composition of alcoholic beverage was studied by headspace solid-phase microextraction (HSSPME) method and gas chromatography - mass spectrometry (GC-MS). Some volatile compounds, such as alcohols, esters, terpenes and other are mainly responsible for the flavor of fortified wines and their amounts specify the quality of the alcoholic beverages. From this perspective it is interesting to develop a rapid, selective and sensitive analytical method suitable for simultaneous quantification of the main molecules being responsible for the organoleptic characteristic of alcoholic beverages. Vermouth fortified drink was analyzed in order to characterize the volatile profile. Using the HS-SPME/GC-MS a number of twenty-six volatile compounds from a commercial market alcoholic beverage were identified. The most abundant compounds were m-thymol, o-thymol and eugenol, alongside of the ethyl ester compounds.
Anti-Legionella activity of essential oil of Satureja cuneifolia.

PubMed

Dunkić, Valerija; Mikrut, Antonija; Bezić, Nada

2014-05-01

The essential oil of Satureja cuneifolia Ten. was characterized by a high concentration of the phenolic compounds carvacrol (21.3%) and thymol (9.2%). The in vitro activity of the essential oil against Legionela pneumophila serogroups (SG) I and 2-15 and Legionella spp. from different sources, using microdilution, showed that L. pneumofila is sensitive to the oil, with MICs ranging from 0.12 to 0.5%, v/v, and a MBC at 0.5 to 1%, v/v. The essential oil of S. cuneifolia was effective in the reduction of Legionellosis infections.
Determination of cinnamaldehyde, carvacrol and thymol in feedstuff additives by pressurized liquid extraction followed by gas chromatography-mass spectrometry.

PubMed

Jiménez-Salcedo, Marta; Tena, María Teresa

2017-03-03

Specific blends of essential oils (BEOs) are promising substitutes for antibiotics to promote livestock performance and to reduce the incidence of intestinal disorders. Microencapsulation of BEOs has shown to improve their stability, bioavailability and to control their release rate once they are added to the feedstuff. The development and validation of a method for determining essential oil components such as carvacrol, thymol and cinnamaldehyde in a microencapsulated material used as feed additive is presented. Analytes were extracted from feed additives and feedstuff by pressurized liquid extraction (PLE) with methanol at 50°C for 5min. Methanol provided good recovery values and cleaner extracts than other polar organic solvents tested. However, for certain kind of composite additives ethyl acetate showed to be a better option because trans-cinnamaldehyde undergoes chemical reaction in methanol. Then PLE extracts were analysed by gas chromatography coupled to ion trap mass spectrometry in selected ion storage (SIS) mode. The analyte stability and the absence of analyte losses during the PLE process was checked by a recovery study. Also, the matrix effect was studied to assess accuracy. Recovery values were between 85 and 115% in most cases. Intra- and inter-day relative standard deviation values were less than 4 and 14%, respectively. Finally, the developed method was applied to the analysis of a microencapsulated feed additive, several composite feed additive samples containing microencapsulated BEOs and a spiked feedstuff, for quality control and in stability studies. Copyright © 2017 Elsevier B.V. All rights reserved.
Essential oils--their antimicrobial activity against Escherichia coli and effect on intestinal cell viability.

PubMed

Fabian, Dusan; Dusan, Fabian; Sabol, Marián; Marián, Sabol; Domaracká, Katarína; Katarína, Domaracká; Bujnáková, Dobroslava; Dobroslava, Bujnáková

2006-12-01

Essential oils are known to possess antimicrobial activity against a wide spectrum of bacteria. The main objective of this study was to evaluate possible harmful effects of four commonly used essential oils and their major components on intestinal cells. Antimicrobial activity of selected plant extracts against enteroinvasive Escherichia coli was dose dependent. However, doses of essential oils with the ability to completely inhibit bacterial growth (0.05%) showed also relatively high cytotoxicity to intestinal-like cells cultured in vitro. Lower doses of essential oils (0.01%) had only partial antimicrobial activity and their damaging effect on Caco-2 cells was only modest. Cell death assessment based on morphological and viability staining followed by fluorescence microscopy showed that essential oils of cinnamon and clove and their major component eugenol had almost no cytotoxic effect at lower doses. Although essential oil of oregano and its component carvacrol slightly increased the incidence of apoptotic cell death, they showed extensive antimicrobial activity even at lower concentrations. Relatively high cytotoxicity was demonstrated by thyme oil, which increased both apoptotic and necrotic cell death incidence. In contrast, its component thymol showed no cytotoxic effect as well as greatly-reduced ability to inhibit visible growth of the chosen pathogen in the doses used. On the other hand, the addition of all essential oils and their components at lower doses, with the exception of thyme oil, to bacterial suspension significantly reduced the cytotoxic effect of E. coli on Caco-2 cells after 1h culture. In conclusion, it is possible to find appropriate doses of essential oils showing both antimicrobial activity and very low detrimental effect on intestinal cells.
Development of antioxidant packaging material by applying corn-zein to LLDPE film in combination with phenolic compounds.

PubMed

Park, Hye-Yeon; Kim, Sung-Jin; Kim, Ki Myong; You, Young-Sun; Kim, So Yeon; Han, Jaejoon

2012-10-01

Functional active packaging materials were successfully developed by incorporating antioxidant agents into corn-zein-laminated linear low-density polyethylene (LLDPE) film. The minimum effective concentrations of the active compounds (for example, thymol, carvacrol, eugenol) were determined and these compounds were then laminated into LLDPE films to develop corn-zein-laminated films with antioxidant agents. The release rate of antioxidant agents in gas and liquid media were determined along with the mechanical and water barrier properties of the films containing these compounds. Tensile strength and percentage elongation at break were reduced in the corn-zein-laminated LLDPE films when compared to typical LLDPE film. Furthermore, the ability of the corn-zein-laminated films to repel moisture decreased by approximately 12.2%, but was improved by incorporating hydrophobic antioxidant compounds in the corn-zein layer. Examination of release kinetics in the gas and liquid phases verified that antioxidants were effectively released from the films and inhibited oxidation during testing. Finally, the films were used for fresh ground beef packaging, and effectively inhibited lipid oxidation and had a positive effect on the color stability of beef patties during storage. These results indicate that the developed antioxidant films are a novel active packaging material that can be effectively implemented by the food industry to improve the quality and safety of foods. Zein protein, a by-product of corn processing industry, was laminated into plastic films in combination with natural phenolic compounds to develop antioxidant packaging films. The films demonstrated their efficient release patterns of antioxidant compounds, which are suitable for packaging applications and food protection. © 2012 Institute of Food Technologists®
Antibacterial and antioxidant activities of essential oils isolated from Thymbra capitata L. (Cav.) andOriganum vulgare L.

PubMed

Faleiro, Leonor; Miguel, Graça; Gomes, Sónia; Costa, Ludmila; Venâncio, Florencia; Teixeira, Adriano; Figueiredo, A Cristina; Barroso, José G; Pedro, Luis G

2005-10-19

Antilisterial activities of Thymbra capitata and Origanum vulgare essential oils were tested against 41 strains of Listeria monocytogenes. The oil of T. capitata was mainly constituted by one component, carvacrol (79%), whereas for O. vulgare three components constituted 70% of the oil, namely, thymol (33%), gamma-terpinene (26%), and p-cymene (11%). T. capitata essential oil had a significantly higher antilisterial activity in comparison to O. vulgare oil and chloramphenicol. No significant differences in L. monocytogenes susceptibilities to the essential oils tested were registered. The minimum inhibitory concentration values of T. capitata essential oil and of carvacrol were quite similar, ranging between 0.05 and 0.2 microL/mL. Antioxidant activity was also tested, the essential oil of T. capitata showing significantly higher antioxidant activity than that of O. vulgare. Use of T. capitata and O. vulgare essential oils can constitute a powerful tool in the control of L. monocytogenes in food and other industries.
In-vitro effects of Thymus munbyanus essential oil and thymol on human sperm motility and function.

PubMed

Chikhoune, Amirouche; Stouvenel, Laurence; Iguer-Ouada, Mokrane; Hazzit, Mohamed; Schmitt, Alain; Lorès, Patrick; Wolf, Jean Philippe; Aissat, Kamel; Auger, Jacques; Vaiman, Daniel; Touré, Aminata

2015-09-01

Traditional medicine has been used worldwide for centuries to cure or prevent disease and for male or female contraception. Only a few studies have directly investigated the effects of herbal compounds on spermatozoa. In this study, essential oil from Thymus munbyanus was extracted and its effect on human spermatozoa in vitro was analysed. Gas chromatography and Gas chromatography-mass spectrometry analyses identified 64 components, accounting for 98.9% of the composition of the oil. The principal components were thymol (52.0%), γ-terpinene (11.0%), ρ-cymene (8.5%) and carvacrol (5.2%). Freshly ejaculated spermatozoa was exposed from control individuals to various doses of the essential oil for different time periods, and recorded the vitality, the mean motility, the movement characteristics (computer-aided sperm analysis), the morphology and the ability to undergo protein hyperphosphorylation and acrosomal reaction, which constitute two markers of sperm capacitation and fertilizing ability. In vitro, both the essential oil extracted from T. munbyanus and thymol, the principal compound present in this oil, impaired human sperm motility and its capacity to undergo hyperphosphorylation and acrosome reaction. These compounds may, therefore, be of interest in the field of reproductive biology, as potential anti-spermatic agents. Copyright © 2015 Reproductive Healthcare Ltd. Published by Elsevier Ltd. All rights reserved.
Effect of mixed antimicrobial agents and flavors in active packaging films.

PubMed

Gutiérrez, Laura; Escudero, Ana; Batlle, Ramón; Nerín, Cristina

2009-09-23

Active packaging is an emerging food technology to improve the quality and safety of food products. Many works have been developed to study the antimicrobial activity of essential oils. Essential oils have been traditionally used as flavorings in food, so they have an important odor impact but they have as well antimicrobial properties that could be used to protect the food. Recent developments in antimicrobial active packaging showed the efficiency of essential oils versus bread and bakery products among other applications. However, one of the main problems to face is the odor and taste they could provide to the packaged food. Using some aromas to mask the odor could be a good approach. That is why the main objective of this paper is to develop an antimicrobial packaging material based on the combination of the most active compounds of essential oils (hydrocinnamaldehyde, oregano essential oil, cinnamaldehyde, thymol, and carvacrol) together with some aromas commonly used in the food industry. A study of the concentration required to get the antimicrobial properties, the organoleptic compatibility with typical aroma present in many food systems (vanilla, banana, and strawberry), and the right combination of both systems has been carried out. Antimicrobial tests of both the mentioned aromas, the main components of some essential oils, and the combination of both groups were carried out against bacteria (Enterococcus faecalis, Listeria monocytogenes, Bacillus cereus, Staphylococcus aureus, Salmonella choleraesuis, Yersinia enterocolitica, Escherichia coli), yeasts (Candida albicans, Debaryomyces hansenii, Zygosaccharomyces rouxii), and molds (Botrytis cinerae, Aspergillus flavus, Penicillium roqueforti, Eurotium repens, Penicillium islandicum, Penicillium commune, Penicillium nalgiovensis). The sensory properties of the combinations were evaluated with a triangular test and classification was by an order test; the odor threshold of the aroma compounds was also studied. The results reveal that none of the aromas had antimicrobial properties. The most antimicrobial compounds are thymol, carvacrol, and cinnamaldehyde, but none of them could be combined with banana aroma, whereas only thymol with strawberry aroma gave the right combined organoleptic profile. All of the antimicrobials under study could be combined with vanilla aroma, providing both antimicrobial property and the odor expected.
Volatile constituents of Dianthus rupicola Biv. from Sicily: activity against microorganisms affecting cellulosic objects.

PubMed

Casiglia, Simona; Bruno, Maurizio; Senatore, Felice

2014-01-01

Dianthus rupicola Biv. (cliffs carnation) is a camephytic, suffruticous, perennial plant growing up to 40 cm high. The plant is widespread in Sicily and neighbouring islands (Egadi, Lampedusa, Lipari) and in some areas of southern Italy. GC and GC-MS analyses of the essential oil distilled from the flowers showed the presence of 66 components. Its composition is characterised by the high content of thymol and carvacrol derivatives. A good antibacterial activity against Bacillus cereus and Bacillussubtilis, both infesting cellulosic historical material, was shown, whereas the antioxidant capacity was determined to be quite poor.
Bumble bee parasite strains vary in resistance to phytochemicals

PubMed Central

Palmer-Young, Evan C.; Sadd, Ben M.; Stevenson, Philip C.; Irwin, Rebecca E.; Adler, Lynn S.

2016-01-01

Nectar and pollen contain diverse phytochemicals that can reduce disease in pollinators. However, prior studies showed variable effects of nectar chemicals on infection, which could reflect variable phytochemical resistance among parasite strains. Inter-strain variation in resistance could influence evolutionary interactions between plants, pollinators, and pollinator disease, but testing direct effects of phytochemicals on parasites requires elimination of variation between bees. Using cell cultures of the bumble bee parasite Crithidia bombi, we determined (1) growth-inhibiting effects of nine floral phytochemicals and (2) variation in phytochemical resistance among four parasite strains. C. bombi growth was unaffected by naturally occurring concentrations of the known antitrypanosomal phenolics gallic acid, caffeic acid, and chlorogenic acid. However, C. bombi growth was inhibited by anabasine, eugenol, and thymol. Strains varied >3-fold in phytochemical resistance, suggesting that selection for phytochemical resistance could drive parasite evolution. Inhibitory concentrations of thymol (4.53–22.2 ppm) were similar to concentrations in Thymus vulgaris nectar (mean 5.2 ppm). Exposure of C. bombi to naturally occurring levels of phytochemicals—either within bees or during parasite transmission via flowers—could influence infection in nature. Flowers that produce antiparasitic phytochemicals, including thymol, could potentially reduce infection in Bombus populations, thereby counteracting a possible contributor to pollinator decline. PMID:27883009
Bumble bee parasite strains vary in resistance to phytochemicals.

PubMed

Palmer-Young, Evan C; Sadd, Ben M; Stevenson, Philip C; Irwin, Rebecca E; Adler, Lynn S

2016-11-24

Nectar and pollen contain diverse phytochemicals that can reduce disease in pollinators. However, prior studies showed variable effects of nectar chemicals on infection, which could reflect variable phytochemical resistance among parasite strains. Inter-strain variation in resistance could influence evolutionary interactions between plants, pollinators, and pollinator disease, but testing direct effects of phytochemicals on parasites requires elimination of variation between bees. Using cell cultures of the bumble bee parasite Crithidia bombi, we determined (1) growth-inhibiting effects of nine floral phytochemicals and (2) variation in phytochemical resistance among four parasite strains. C. bombi growth was unaffected by naturally occurring concentrations of the known antitrypanosomal phenolics gallic acid, caffeic acid, and chlorogenic acid. However, C. bombi growth was inhibited by anabasine, eugenol, and thymol. Strains varied >3-fold in phytochemical resistance, suggesting that selection for phytochemical resistance could drive parasite evolution. Inhibitory concentrations of thymol (4.53-22.2 ppm) were similar to concentrations in Thymus vulgaris nectar (mean 5.2 ppm). Exposure of C. bombi to naturally occurring levels of phytochemicals-either within bees or during parasite transmission via flowers-could influence infection in nature. Flowers that produce antiparasitic phytochemicals, including thymol, could potentially reduce infection in Bombus populations, thereby counteracting a possible contributor to pollinator decline.
Essential Oil Characterization of Thymus vulgaris from Various Geographical Locations

PubMed Central

Satyal, Prabodh; Murray, Brittney L.; McFeeters, Robert L.; Setzer, William N.

2016-01-01

Thyme (Thymus vulgaris L.) is a commonly used flavoring agent and medicinal herb. Several chemotypes of thyme, based on essential oil compositions, have been established, including (1) linalool; (2) borneol; (3) geraniol; (4) sabinene hydrate; (5) thymol; (6) carvacrol, as well as a number of multiple-component chemotypes. In this work, two different T. vulgaris essential oils were obtained from France and two were obtained from Serbia. The chemical compositions were determined using gas chromatography–mass spectrometry. In addition, chiral gas chromatography was used to determine the enantiomeric compositions of several monoterpenoid components. The T. vulgaris oil from Nyons, France was of the linalool chemotype (linalool, 76.2%; linalyl acetate, 14.3%); the oil sample from Jablanicki, Serbia was of the geraniol chemotype (geraniol, 59.8%; geranyl acetate, 16.7%); the sample from Pomoravje District, Serbia was of the sabinene hydrate chemotype (cis-sabinene hydrate, 30.8%; trans-sabinene hydrate, 5.0%); and the essential oil from Richerenches, France was of the thymol chemotype (thymol, 47.1%; p-cymene, 20.1%). A cluster analysis based on the compositions of these essential oils as well as 81 additional T. vulgaris essential oils reported in the literature revealed 20 different chemotypes. This work represents the first chiral analysis of T. vulgaris monoterpenoids and a comprehensive description of the different chemotypes of T. vulgaris. PMID:28231164
Are all phytochemicals useful in the preventing of DNA damage?

PubMed

Bacanlı, Merve; Aydın, Sevtap; Başaran, A Ahmet; Başaran, Nurşen

2017-11-01

Phytochemicals derived from natural plants have been used commonly for the prevention and/or treatment of different diseases due to the belief of their safety. Many plant species synthesize toxic chemicals. New natural chemicals are being discovered but their toxic effects are unknown. Phytochemicals have been regarded as possible antioxidants. But on the other hand it is suggested that various phenolic antioxidants can display pro-oxidant properties at high doses. In this review, the role of some phytochemicals (epigallocathecin gallate, carvacrol, galangin, limonene, lycopene, naringin, puerarin, terpinene, thymol and ursolic acid) on the prevention of DNA damage will be discussed. Copyright © 2017 Elsevier Ltd. All rights reserved.
Trans-Cinnamaldehyde, Carvacrol, and Eugenol Reduce Campylobacter jejuni Colonization Factors and Expression of Virulence Genes in Vitro

PubMed Central

Upadhyay, Abhinav; Arsi, Komala; Wagle, Basanta R.; Upadhyaya, Indu; Shrestha, Sandip; Donoghue, Ann M.; Donoghue, Dan J.

2017-01-01

Campylobacter jejuni is a major foodborne pathogen that causes severe gastroenteritis in humans characterized by fever, diarrhea, and abdominal cramps. In the human gut, Campylobacter adheres and invades the intestinal epithelium followed by cytolethal distending toxin mediated cell death, and enteritis. Reducing the attachment and invasion of Campylobacter to intestinal epithelium and expression of its virulence factors such as motility and cytolethal distending toxin (CDT) production could potentially reduce infection in humans. This study investigated the efficacy of sub-inhibitory concentrations (SICs, concentration not inhibiting bacterial growth) of three GRAS (generally recognized as safe) status phytochemicals namely trans-cinnamaldehyde (TC; 0.005, 0.01%), carvacrol (CR; 0.001, 0.002%), and eugenol (EG; 0.005, 0.01%) in reducing the attachment, invasion, and translocation of C. jejuni on human intestinal epithelial cells (Caco-2). Additionally, the effect of these phytochemicals on Campylobacter motility and CDT production was studied using standard bioassays and gene expression analysis. All experiments had duplicate samples and were replicated three times on three strains (wild type S-8, NCTC 11168, 81–176) of C. jejuni. Data were analyzed using ANOVA with GraphPad ver. 6. Differences between the means were considered significantly different at P < 0.05. The majority of phytochemical treatments reduced C. jejuni adhesion, invasion, and translocation of Caco-2 cells (P < 0.05). In addition, the phytochemicals reduced pathogen motility and production of CDT in S-8 and NCTC 11168 (P < 0.05). Real-time quantitative PCR revealed that phytochemicals reduced the transcription of select C. jejuni genes critical for infection in humans (P < 0.05). Results suggest that TC, CR, and EG could potentially be used to control C. jejuni infection in humans. PMID:28487683
Application of Volatile Antifungal Plant Essential Oils for Controlling Pepper Fruit Anthracnose by Colletotrichum gloeosporioides.

PubMed

Hong, Jeum Kyu; Yang, Hye Ji; Jung, Heesoo; Yoon, Dong June; Sang, Mee Kyung; Jeun, Yong-Chull

2015-09-01

Anthracnose caused by Colletotrichum gloeosporioides has been destructive during pepper fruit production in outdoor fields in Korea. In vitro antifungal activities of 15 different plant essential oils or its components were evaluated during conidial germination and mycelial growth of C. gloeosporioides. In vitro conidial germination was most drastically inhibited by vapour treatments with carvacrol, cinnamon oil, trans-cinnamaldehyde, citral, p-cymene and linalool. Inhibition of the mycelial growth by indirect vapour treatment with essential oils was also demonstrated compared with untreated control. Carvacrol, cinnamon oil, trans-cinnamaldehyde, citral and eugenol were among the most inhibitory plant essential oils by the indirect antifungal efficacies. Plant protection efficacies of the plant essential oils were demonstrated by reduced lesion diameter on the C. gloeosporioides-inoculated immature green pepper fruits compared to the inoculated control fruits without any plant essential oil treatment. In planta test showed that all plant essential oils tested in this study demonstrated plant protection efficacies against pepper fruit anthracnose with similar levels. Thus, application of different plant essential oils can be used for eco-friendly disease management of anthracnose during pepper fruit production.
The anti-dermatophyte activity of Zataria multiflora essential oils.

PubMed

Mahboubi, M; HeidaryTabar, R; Mahdizadeh, E

2017-06-01

Dermtophytes are a group of pathogenic fungi and the major cause of dermatophytosis in humans and animals. Fighting dermatophytes by natural essential oils is one important issue in new researches. In this investigation, we evaluated the anti-dermatophyte activities of three samples of Z. multiflora essential oils against dermatophytes along with analysis of chemical compositions of the essential oils and their anti-elastase activities on elastase production in dermatophytes. Carvacrol (1.5-34.4%), thymol (25.8-41.2%), carvacrol methyl ether (1.9-28.3%) and p-cymene (2.3-8.3%) were the main components of Z. multiflora essential oils. Z. multiflora essential oils (100ppm) inhibited the mycelium growth of dermatophytes (6±1.7-47.0±1.4%) and had the minimal inhibitory concentration (MIC) and minimal fungicidal concentration (MFC) values of 0.03-0.25μl/ml against dermatophytes. Essential oils inhibited elastase produced in dermatophytes and pure porcine elastase. Z. multiflora essential oils can be used as natural anti-dermatophyte agent for fighting dermatophytes in further preclinical and clinical studies. Copyright © 2017 Elsevier Masson SAS. All rights reserved.
Essential oil diversity of European Origanum vulgare L. (Lamiaceae).

PubMed

Lukas, Brigitte; Schmiderer, Corinna; Novak, Johannes

2015-11-01

This investigation focused on the qualitative and quantitative composition of essential oil compounds of European Origanum vulgare. Extracts of 502 individual O. vulgare plants from 17 countries and 51 populations were analyzed via GC. Extracts of 49 plants of 5 populations of Israeli Origanum syriacum and 30 plants from 3 populations of Turkish Origanum onites were included to exemplify essential oil characteristics of 'high-quality' oregano. The content of essential oil compounds of European O. vulgare ranged between 0.03% and 4.6%. The monoterpenes were primarily made up of sabinene, myrcene, p-cymene, 1,8-cineole, β-ocimene, γ-terpinene, sabinene hydrate, linalool, α-terpineol, carvacrol methyl ether, linalyl acetate, thymol and carvacrol. Among the sesquiterpenes β-caryophyllene, germacrene D, germacrene D-4-ol, spathulenol, caryophyllene oxide and oplopanone were often present in higher amounts. According to the proportions of cymyl-compounds, sabinyl-compounds and the acyclic linalool/linalyl acetate three different main monoterpene chemotypes were defined. The cymyl- and the acyclic pathway were usually active in plants from the Mediterranean climate whereas an active sabinyl-pathway was a characteristic of plants from the Continental climate. Copyright © 2015 Elsevier Ltd. All rights reserved.
Antimicrobial and antioxidant activities and chemical characterization of essential oils of Thymusvulgaris, Rosmarinus officinalis, and Origanum majorana from northeastern México.

PubMed

Guerra-Boone, Laura; Alvarez-Román, Rocío; Alvarez-Román, Rocío; Salazar-Aranda, Ricardo; Torres-Cirio, Anabel; Rivas-Galindo, Verónica Mayela; de-Torres, Noemí Waksman; González, Gloria; Pérez-López, Luis Alejandro

2015-01-01

There have been no reports of antifungal activity and composition of extracts from Thymus vulgaris, Rosmarinus officinalis or Origanum majorana from northeastern México. Antifungal activity of these oils against Trichophyton rubrum, Trichophyton tonsurans, Trichophyton mentagrophytes, Microsporum gypseum, Microsporum canis and Epidermophyton floccosum was measured by diffusion assay. Additionally, antibacterial and antioxidant activities were evaluated. Antibacterial activity against Staphylococcus aureus and Streptococcus pyogenes was examined by microdilution. Antioxidant activity was assessed by 2,2-difenil-1-picrilhidracil reduction test. The plant oils were characterized by both GC/MS and GC/FID. Oils of T. vulgaris and O. majorana showed growth inhibition activity against dermatophytes, especially T. vulgaris oil, which completely inhibited growth of all tested dermatophytes. The oils also showed bioactivity against bacteria, with minimum inhibitory concentration (MIC) values between 62.5 and 500 μg/mL. The antioxidant activity of the oils was low, with effective concentration (EC50) values <250μg/mL. The major components in the oils were as follows: T. vulgaris, o-cymene, μ-terpinene, thymol and carvacrol; R. officinalis, terpinen-4-ol and 1,8-cineole; O. majorana, terpinen-4-ol and thymol.
Microencapsulated sorbic acid and pure botanicals affect Salmonella Typhimurium shedding in pigs: a close-up look from weaning to slaughter in controlled and field conditions.

PubMed

Grilli, Ester; Foresti, Fabio; Tugnoli, Benedetta; Fustini, Mattia; Zanoni, Maria G; Pasquali, Paolo; Callaway, Todd R; Piva, Andrea; Alborali, Giovanni L

2015-10-01

The aim of this study was to assess the efficacy of a combination of sorbic acid, thymol, and carvacrol in reducing the prevalence and shedding level of Salmonella Typhimurium in pigs either in a controlled challenge environment or in a production setting. In the first study, 24 weaned piglets were separated in 4 isolation units (6 piglets/isolation unit). Each unit received either a basal diet (no treatment) or a microencapsulated mixture of sorbic acid, thymol, and carvacrol at 1, 2, or 5 g/kg of feed. After 21 d, pigs were orally challenged with 6 log10 colony-forming units of Salmonella Typhimurium. Blood samples and feces from rectal ampullae were collected every week. On d56 of the study, pigs were euthanized and necropsied to collect intestinal contents (jejunum through colon) and ileocecal lymph nodes. Samples were analyzed for Salmonella Typhimurium and serological analysis was also conducted. In the second study, an all-in-all-out multisite pig farm that was positive for monophasic Salmonella Typhimurium was followed throughout a production cycle from weaning to slaughter. Pigs received either a basal diet or the basal diet including 5 g/kg of the microencapsulated additive. Environmental, fecal, and blood samples were collected monthly, and cecal contents and ileocecal lymph nodes were collected at slaughter to isolate and enumerate Salmonella. The results indicate that the additive at 5 g/kg tended to reduce Salmonella fecal prevalence in both a controlled challenge (p=0.07) and in production conditions (p=0.03). Nevertheless, the additive did not reduce the number of pigs seropositive for Salmonella, nor it reduced the Salmonella prevalence at slaughter. The data indicate that these additives are not effective alone but must be used in conjunction with appropriate containment measures at lairage in order to prevent reinfection in pigs and to reduce the number of pigs carrying Salmonella entering the food chain.
Citrus fruit extracts with carvacrol and thymol eliminated 7-log acid-adapted Escherichia coli O157:H7, Salmonella typhimurium, and Listeria monocytogenes: A potential of effective natural antibacterial agents.

PubMed

Chung, Doohyun; Cho, Tae Jin; Rhee, Min Suk

2018-05-01

Despite the widespread belief that citrus fruit extracts (CFEs) are microbiologically safe due to their acidity, limited bactericidal effect results in low applicability as antibacterial agent and outbreaks occurred by acid-adapted pathogens. Here, we examined the antibacterial effects of CFEs [lime (Citrus medica), lemon (Citrus limon), calamansi (Citrus microcarpa)] combined with essential oil components (EOCs; carvacrol and thymol) against non-acid-adapted/acid-adapted Escherichia coli O157:H7, Salmonella Typhimurium, and Listeria monocytogenes under 22 °C for 5 min. CFEs (<20%) alone or small amounts of EOCs (2.0 mM; 0.032%) alone could not inactivate the target bacteria effectively. However, combined treatments exhibited marked synergy: CFE + EOCs eliminated all the bacteria (>6.9 log CFU/ml). Among the CFEs tested, the highest synergism was shown by calamansi, an exotic citrus fruit previously unrecognized as an antibacterial agent. Although acid-adaptation improved bacterial survival, calamansi (<20%) + EOCs (<0.032%) completely inactivated even the most resistant pathogen (E. coli O157:H7). Validation test also showed that all tested commercial juice products also eliminated acid-adapted pathogens when used with EOCs. Physicochemical analysis of tested CFEs (pH measurement and HPLC analysis of components) revealed that low pH and flavanone (hesperidin) did not contribute to the synergistic bactericidal effects. Rather, the high citric acid content is likely to contribute to the strong synergistic effect with EOCs by damaging susceptible bacterial membranes. Sensory scores for CFEs were not altered by addition of EOCs at concentrations up to 1.5 mM. This study provides new insight into the utility of CFEs with EOCs to improve not only the microbiological safety of food products containing CFEs but also their applicability as natural antibacterial complex. Copyright © 2018 Elsevier Ltd. All rights reserved.

The constituents of essential oil in leaves of Karaj accession of Trigonella foenum graecum.

PubMed

Riasat, Mehrnaz; Jafari, Ali Ashraf; Bahmanzadegan, Atefeh; Hatami, Ahmad; Zareiyan, Faraneh

2017-07-01

The chemical composition of the essential oils of Karaj accession of Trigonella foenum graecum leaves was detected by hydro-distillation and analysed by gas chromatography (GC-FID) and gas chromatography-mass spectroscopy (GC-MS) apparatuses for first time. Thirty-six compounds representing 95.3% of the total components were identified. The patterns of the main compounds were (2E)-Hexenal (26.61%), n-Hexadecanoic acid (10.14%) and (E)-b-Ionone (7.99%). Other notable constituents were Thymol (4.79%), 6,10,14-trimethyl-2-Pentadecanone (4.59%), Carvacrol (3.40%), (E)-Nerolidol (3.32%) and (2E,6Z)-Nonadienal (3.30%). (2E)-Hexenal was found as the most dominant component in this study.
Application of Volatile Antifungal Plant Essential Oils for Controlling Pepper Fruit Anthracnose by Colletotrichum gloeosporioides

PubMed Central

Hong, Jeum Kyu; Yang, Hye Ji; Jung, Heesoo; Yoon, Dong June; Sang, Mee Kyung; Jeun, Yong-Chull

2015-01-01

Anthracnose caused by Colletotrichum gloeosporioides has been destructive during pepper fruit production in outdoor fields in Korea. In vitro antifungal activities of 15 different plant essential oils or its components were evaluated during conidial germination and mycelial growth of C. gloeosporioides. In vitro conidial germination was most drastically inhibited by vapour treatments with carvacrol, cinnamon oil, trans-cinnamaldehyde, citral, p-cymene and linalool. Inhibition of the mycelial growth by indirect vapour treatment with essential oils was also demonstrated compared with untreated control. Carvacrol, cinnamon oil, trans-cinnamaldehyde, citral and eugenol were among the most inhibitory plant essential oils by the indirect antifungal efficacies. Plant protection efficacies of the plant essential oils were demonstrated by reduced lesion diameter on the C. gloeosporioides-inoculated immature green pepper fruits compared to the inoculated control fruits without any plant essential oil treatment. In planta test showed that all plant essential oils tested in this study demonstrated plant protection efficacies against pepper fruit anthracnose with similar levels. Thus, application of different plant essential oils can be used for eco-friendly disease management of anthracnose during pepper fruit production. PMID:26361475
Inhibitory effects of spices on growth and toxin production of toxigenic fungi.

PubMed Central

Hitokoto, H; Morozumi, S; Wauke, T; Sakai, S; Kurata, H

1980-01-01

The inhibitory effects of 29 commercial powdered spices on the growth and toxin production of three species of toxigenic Aspergillus were observed by introducing these materials into culture media for mycotoxin production. Of the 29 samples tested, cloves, star anise seeds, and allspice completely inhibited the fungal growth, whereas most of the others inhibited only the toxin production. Eugenol extracted from cloves and thymol from thyme caused complete inhibition of the growth of both Aspergillus flavus and Aspergillus versicolor at 0.4 mg/ml or less. At a concentration of 2 mg/ml, anethol extracted from star anise seeds inhibited the growth of all the strains. PMID:6769391
Chemical Polymorphism of Origanum compactum Grown in All Natural Habitats in Morocco.

PubMed

Aboukhalid, Kaoutar; Lamiri, Abdeslam; Agacka-Mołdoch, Monika; Doroszewska, Teresa; Douaik, Ahmed; Bakha, Mohamed; Casanova, Joseph; Tomi, Félix; Machon, Nathalie; Faiz, Chaouki Al

2016-09-01

Origanum compactum L. (Lamiaceae) is one of the most important medicinal species in term of ethnobotany in Morocco. It is considered as a very threatened species as it is heavily exploited. Its domestication remains the most efficient way to safeguard it for future generations. For this purpose, wide evaluation of the existing variability in all over the Moroccan territory is required. The essential oils of 527 individual plants belonging to 88 populations collected from the whole distribution area of the species in Morocco were analyzed by GC/MS. The dominant constituents were carvacrol (0 - 96.3%), thymol (0 - 80.7%), p-cymene (0.2 - 58.6%), γ-terpinene (0 - 35.2%), carvacryl methyl ether (0 - 36.2%), and α-terpineol (0 - 25.8%). While in the Middle Atlas region and the Central Morocco mainly carvacrol type samples were found, much higher chemotypic diversity was encountered within samples from the north part of Morocco (occidental and central Rif regions). The high chemical polymorphism of plants offers a wide range for selection of valuable chemotypes, as a part of breeding and domestication programs of this threatened species. © 2016 Wiley-VHCA AG, Zürich.
Insecticidal and acetylcholine esterase inhibition activity of Apiaceae plant essential oils and their constituents against adults of German cockroach (Blattella germanica).

PubMed

Yeom, Hwa-Jeong; Kang, Jae Soon; Kim, Gil-Hah; Park, Il-Kwon

2012-07-25

We evaluated the insecticidal and acetylcholine esterase (AChE) inhibition activity of 11 Apiaceae plant essential oils and their constituents in adult male and female Blattella germanica. Of the 11 Apiaceae plant essential oils tested, dill (Anethum graveolens), carvi (Carum carvi), and cumin (Cuminum cyminum) demonstrated >90% fumigant toxicity against adult male German cockroaches at a concentration of 5 mg/filter paper. In a contact toxicity test, dill (Anethum graveolens), carvi (Carum carvi), cumin (Cuminum cyminum), and ajowan (Trachyspermum ammi) produced strong insecticidal activity against adult male and female German cockroaches. Among the test compounds, (S)-(+)-carvone, 1,8-cineole, trans-dihydrocarvone, cuminaldehyde, trans-anethole, p-cymene, and γ-terpinene demonstrated strong fumigant toxicity against adult male and female B. germanica. In a contact toxicity test, carveol, cuminaldehyde, (S)-(+)-carvone, trans-anethole, thymol, and p-cymene showed strong contact toxicity against adult male and female B. germanica. IC(50) values of α-pinene, carvacrol, and dihydrocarvone against female AChE were 0.28, 0.17, and 0.78 mg/mL, respectively. The toxicity of the blends of constituents identified in 4 active oils indicated that carvone, cuminaldehyde, and thymol were major contributors to the fumigant activity or contact toxicity of the artificial blend.
Carum copticum L.: A Herbal Medicine with Various Pharmacological Effects

PubMed Central

Boskabady, Mohammad Hossein; Alitaneh, Saeed; Alavinezhad, Azam

2014-01-01

Carum copticum L. commonly known as “Ajwain” is cultivated in many regions of the world including Iran and India, states of Gujarat and Rajasthan. Traditionally, C. copticum has been used in the past for various therapeutic effects including bloating, fatigue, diarrhea, abdominal tumors, abdominal pain, respiratory distress, and loss of appetite. It has other health benefits such as antifungal, antioxidant, antibacterial, antiparasitic, and hypolipidemic effects. This plant contains different important components such as carbohydrates, glucosides, saponins and phenolic compounds (carvacrol), volatile oils (thymol), terpiene, paracymene and beta-pinene, protein, fat, fiber, and minerals including calcium, phosphorus, iron, and nicotinic acid (niacin). In the previous studies, several pharmacological effects were shown for C. copticum. Therefore, in this paper, the pharmacological effects of the plant were reviewed. PMID:25089273
[Extraction and analysis of chemical components of essential oil in Thymus vulgaris of tissue culture].

PubMed

Li, Xiao-Dong; Yang, Li; Xu, Shi-Qian; Li, Jian-Guo; Cheng, Zhi-Hui; Dang, Jian-Zhang

2011-10-01

To extract the essential oils from the Seedlings, the Aseptic Seedlings and the Tissue Culture Seedlings of Thymus vulgaris and analyze their chemical components and the relative contents. The essential oils were extracted by steam distillation, the chemical components and the relative contents were identified and analyzed by gas chromatography-mass spectrometry (GC/MS) and peak area normalization method. The main chemical components of essential oil in these three samples had no significant difference, they all contained the main components of essential oil in Thymus vulgaris: Thymol, Carvacrol, o-Cymene, gamma-Terpinene, Caryophyllene et al. and only had a slight difference in the relative content. This study provides important theoretical foundation and data reference for further study on production of essential oil in thyme by tissue culture technology.
Isolation and identification of antibacterial compounds from Thymus kotschyanus aerial parts and Dianthus caryophyllus flower buds.

PubMed

Mohammed, Muthanna J; Al-Bayati, Firas A

2009-06-01

The aerial parts of Thymus kotschyanus Boiss. and Hohen. (Lamiaceae) and flower buds of Dianthus caryophyllus L. (Caryophyllaceae) have been traditionally implemented in the treatment of wounds, throat and gum infections and gastro-intestinal disorder by the indigenous people of northern Iraq, although the compounds responsible for the medicinal properties have not been identified. In this study, antibacterial compounds from both plants were isolated and characterized, and the biological activity of each compound was assessed individually and combined. Compounds were isolated and characterized from the extracted essential oils of both plants using different spectral techniques: TLC, FTIR spectra and HPLC. The minimum inhibitory concentrations MIC values for the compounds were assessed individually and combined based on a microdilution and the checkerboard method in 96 multi-well microtiter plates. Two known compounds were isolated from the essential oils of both plants and were identified as thymol and eugenol. The isolated compounds were investigated for their single and combined antibacterial activities against seven selected pathogenic bacteria; Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes, Proteus mirabilis, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa. Thymol MIC values ranged from 15.6 to 250.0 microg/ml and B. cereus was found to be the most sensitive pathogen with a MIC value of 15.6 microg/ml. Eugenol achieved stronger MIC values against most tested pathogens and the best MIC value (15.6 microg/ml) was observed against B. cereus, L. monocytogenes and K. pneumoniae whereas, S. aureus, P. mirabilis and E. coli were inhibited with a MIC value of 31.2 microg/ml. Combination results had antibacterial enhancement against most pathogens and the best synergistic result was seen against P. mirabilis and E. coli. The isolation of two antibacterial compounds from Thymus kotschyanus aerial parts and Dianthus caryophyllus flower buds validates the use of these species in the treatment of throat and gum infections, wound-healing and gastro-intestinal disorder.
Antibacterial activity and mechanism of action of Monarda punctata essential oil and its main components against common bacterial pathogens in respiratory tract.

PubMed

Li, Hong; Yang, Tian; Li, Fei-Yan; Yao, Yan; Sun, Zhong-Min

2014-01-01

The aim of the current research work was to study the chemical composition of the essential oil of Monarda punctata along with evaluating the essential oil and its major components for their antibacterial effects against some frequently encountered respiratory infection causing pathogens. Gas chromatographic mass spectrometric analysis revealed the presence of 13 chemical constituents with thymol (75.2%), p-cymene (6.7%), limonene (5.4), and carvacrol (3.5%) as the major constituents. The oil composition was dominated by the oxygenated monoterpenes. Antibacterial activity of the essential oil and its major constituents (thymol, p-cymene, limonene) was evaluated against Streptococcus pyogenes, methicillin-resistant Staphylococcus aureus (MRSA), Streptococcus pneumoniae, Haemophilus influenzae and Escherichia coli. The study revealed that the essential oil and its constituents exhibited a broad spectrum and variable degree of antibacterial activity against different strains. Among the tested strains, Streptococcus pyogenes, Escherichia coli and Streptococcus pneumoniae were the most susceptible bacterial strain showing lowest MIC and MBC values. Methicillin-resistant Staphylococcus aureus was the most resistant bacterial strain to the essential oil treatment showing relatively higher MIC and MBC values. Scanning electron microscopy revealed that the essential oil induced potent and dose-dependent membrane damage in S. pyogenes and MRSA bacterial strains. The reactive oxygen species generated by the Monarda punctata essential oil were identified using 2', 7'-dichlorofluorescein diacetate (DCFDA).This study indicated that the Monarda punctata essential oil to a great extent and thymol to a lower extent triggered a substantial increase in the ROS levels in S. pyogenes bacterial cultures which ultimately cause membrane damage as revealed by SEM results.
Antibacterial activity and mechanism of action of Monarda punctata essential oil and its main components against common bacterial pathogens in respiratory tract

PubMed Central

Li, Hong; Yang, Tian; Li, Fei-Yan; Yao, Yan; Sun, Zhong-Min

2014-01-01

The aim of the current research work was to study the chemical composition of the essential oil of Monarda punctata along with evaluating the essential oil and its major components for their antibacterial effects against some frequently encountered respiratory infection causing pathogens. Gas chromatographic mass spectrometric analysis revealed the presence of 13 chemical constituents with thymol (75.2%), p-cymene (6.7%), limonene (5.4), and carvacrol (3.5%) as the major constituents. The oil composition was dominated by the oxygenated monoterpenes. Antibacterial activity of the essential oil and its major constituents (thymol, p-cymene, limonene) was evaluated against Streptococcus pyogenes, methicillin-resistant Staphylococcus aureus (MRSA), Streptococcus pneumoniae, Haemophilus influenzae and Escherichia coli. The study revealed that the essential oil and its constituents exhibited a broad spectrum and variable degree of antibacterial activity against different strains. Among the tested strains, Streptococcus pyogenes, Escherichia coli and Streptococcus pneumoniae were the most susceptible bacterial strain showing lowest MIC and MBC values. Methicillin-resistant Staphylococcus aureus was the most resistant bacterial strain to the essential oil treatment showing relatively higher MIC and MBC values. Scanning electron microscopy revealed that the essential oil induced potent and dose-dependent membrane damage in S. pyogenes and MRSA bacterial strains. The reactive oxygen species generated by the Monarda punctata essential oil were identified using 2’, 7’-dichlorofluorescein diacetate (DCFDA).This study indicated that the Monarda punctata essential oil to a great extent and thymol to a lower extent triggered a substantial increase in the ROS levels in S. pyogenes bacterial cultures which ultimately cause membrane damage as revealed by SEM results. PMID:25550774
Chitin-Induced Airway Epithelial Cell Innate Immune Responses Are Inhibited by Carvacrol/Thymol

PubMed Central

Erle, David J.

2016-01-01

Chitin is produced in large amounts by fungi, insects, and other organisms and has been implicated in the pathogenesis of asthma. Airway epithelial cells are in direct contact with environmental particles and serve as the first line of defense against inhaled allergens and pathogens. The potential contributions of airway epithelial cells to chitin-induced asthma remain poorly understood. We hypothesized that chitin directly stimulates airway epithelial cells to release cytokines that promote type 2 immune responses and to induce expression of molecules which are important in innate immune responses. We found that chitin exposure rapidly induced the expression of three key type 2-promoting cytokines, IL-25, IL-33 and TSLP, in BEAS-2B transformed human bronchial epithelial cells and in A549 and H292 lung carcinoma cells. Chitin also induced the expression of the key pattern recognition receptors TLR2 and TLR4. Chitin induced the expression of miR-155, miR-146a and miR-21, each of which is known to up-regulate the expression of pro-inflammatory cytokines. Also the expression of SOCS1 and SHIP1 which are known targets of miR-155 was repressed by chitin treatment. The monoterpene phenol carvacrol (Car) and its isomer thymol (Thy) are found in herbal essential oils and have been shown to inhibit allergic inflammation in asthma models. We found that Car/Thy inhibited the effects of chitin on type 2-promoting cytokine release and on the expression of TLRs, SOCS1, SHIP1, and miRNAs. Car/Thy could also efficiently reduce the protein levels of TLR4, inhibit the increase in TLR2 protein levels in chitin plus Car/Thy-treated cells and increase the protein levels of SHIP1 and SOCS1, which are negative regulators of TLR-mediated inflammatory responses. We conclude that direct effects of chitin on airway epithelial cells are likely to contribute to allergic airway diseases like asthma, and that Car/Thy directly inhibits epithelial cell pro-inflammatory responses to chitin. PMID:27463381
Antibacterial activities of plant essential oils and their components against Escherichia coli O157:H7 and Salmonella enterica in apple juice.

PubMed

Friedman, Mendel; Henika, Philip R; Levin, Carol E; Mandrell, Robert E

2004-09-22

We evaluated 17 plant essential oils and nine oil compounds for antibacterial activity against the foodborne pathogens Escherichia coli O157:H7 and Salmonella enterica in apple juices in a bactericidal assay in terms of % of the sample that resulted in a 50% decrease in the number of bacteria (BA(50)). The 10 compounds most active against E. coli (60 min BA(50) range in clear juice, 0.018-0.093%) were carvacrol, oregano oil, geraniol, eugenol, cinnamon leaf oil, citral, clove bud oil, lemongrass oil, cinnamon bark oil, and lemon oil. The corresponding compounds against S. enterica (BA(50) range, 0.0044-0.011%) were Melissa oil, carvacrol, oregano oil, terpeineol, geraniol, lemon oil, citral, lemongrass oil, cinnamon leaf oil, and linalool. The activity (i) was greater for S. enterica than for E. coli, (ii) increased with incubation temperature and storage time, and (iii) was not affected by the acidity of the juices. The antibacterial agents could be divided into two classes: fast-acting and slow-acting. High-performance liquid chromatography analysis showed that the bactericidal results are related to the composition of the oils. These studies provide information about new ways to protect apple juice and other foods against human pathogens.
The role of flavor and fragrance chemicals in TRPA1 (transient receptor potential cation channel, member A1) activity associated with allergies.

PubMed

Mihara, Satoru; Shibamoto, Takayuki

2015-01-01

TRPA1 has been proposed to be associated with diverse sensory allergic reactions, including thermal (cold) nociception, hearing and allergic inflammatory conditions. Some naturally occurring compounds are known to activate TRPA1 by forming a Michael addition product with a cysteine residue of TRPA1 through covalent protein modification and, in consequence, to cause allergic reactions. The anti-allergic property of TRPA1 agonists may be due to the activation and subsequent desensitization of TRPA1 expressed in sensory neurons. In this review, naturally occurring TRPA1 antagonists, such as camphor, 1,8-cineole, menthol, borneol, fenchyl alcohol and 2-methylisoborneol, and TRPA1 agonists, including thymol, carvacrol, 1'S-1'- acetoxychavicol acetate, cinnamaldehyde, α-n-hexyl cinnamic aldehyde and thymoquinone as well as isothiocyanates and sulfides are discussed.
Immunomodulatory effects of phytogenics in chickens and pigs — A review

PubMed Central

2018-01-01

Environmental stressors like pathogens and toxins may depress the animal immune system through invasion of the gastrointestinal tract (GIT) tract, where they may impair performance and production, as well as lead to increased mortality rates. Therefore, protection of the GIT tract and improving animal health are top priorities in animal production. Being natural-sourced materials, phytochemicals are potential feed additives possessing multiple functions, including: anti-inflammatory, anti-fungal, anti-viral and antioxidative properties. This paper focuses on immunity-related physiological parameters regulated by phytochemicals, such as carvacrol, cinnamaldehyde, curcumin, and thymol; many studies have proven that these phytochemicals can improve animal performance and production. On the molecular level, the impact of inflammatory gene expression on underlying mechanisms was also examined, as were the effects of environmental stimuli and phytochemicals in initiating nuclear factor kappa B and mitogen-activated protein kinases signaling pathways and improving health conditions. PMID:29268586
Chemical Constituents of Essential Oil from Lippia sidoides Cham. (Verbenaceae) Leaves Cultivated in Hidrolândia, Goiás, Brazil

PubMed Central

de Morais, Sandra Ribeiro; Oliveira, Thiago Levi Silva; Bara, Maria Teresa Freitas; da Conceição, Edemilson Cardoso; Rezende, Maria Helena; Ferri, Pedro Henrique; de Paula, José Realino

2012-01-01

Several studies involving the family Verbenaceae, occurring in the Brazilian Cerrado, have emphasized the popular use of many aromatic species. We highlight the use of Lippia sidoides Cham., known as “alecrim pimenta,” native to northeastern Brazil and northern Minas Gerais. Leaves of this species were collected in antropized Brazilian Cerrado area, in Hidrolândia, Goiás, and their essential oils were extracted by hydrodistillation in a Clevenger-type apparatus and thereafter analyzed GC/MS. Among the compounds identified in this study were the most abundant oxygenated monoterpenes, followed by sesquiterpenes hydrocarbons. The oxygenated monoterpene 1,8-cineole was the major constituent followed by isoborneol and bornyl acetate. The chemical composition of essential oil described in this paper differs from that described in the literature for L. sidoides found in its native environment, where the major constituents are thymol and carvacrol. PMID:22505916
Chemical composition and antibacterial activity of Origanum saccatum P.H. Davis essential oil obtained by solvent-free microwave extraction: comparison with hydrodistillation.

PubMed

Sozmen, Fazli; Uysal, Burcu; Oksal, Birsen S; Kose, Elif Odabas; Deniz, I Gokhan

2011-01-01

The components of the essential oils (EOs) obtained by solvent-free microwave extraction (SFME) and hydrodistillation (HD) from endemic Origanum saccatum P.H. Davis were identified by using GC/MS. The main constituents of both EOs obtained by SFME and HD, respectively, from O. saccatum were p-cymene (72.5 and 70.6%), thymol (9.32 and 8.11%), and carvacrol (7.18 and 6.36%). The EO obtained by SFME contained substantially higher amounts of oxygenated compounds and lower amounts of monoterpenes than did the EO obtained by HD. The antibacterial activities of the EOs obtained by SFME and HD were evaluated with the disc diffusion method by comparison with 10 different bacterial strains. The antibacterial activity of the EO extracted by SFME was found to be more effective than that of the EO extracted by HD against seven of the tested bacteria.
Rapid evaluation and quantitative analysis of thyme, origano and chamomile essential oils by ATR-IR and NIR spectroscopy

NASA Astrophysics Data System (ADS)

Schulz, Hartwig; Quilitzsch, Rolf; Krüger, Hans

2003-12-01

The essential oils obtained from various chemotypes of thyme, origano and chamomile species were studied by ATR/FT-IR as well as NIR spectroscopy. Application of multivariate statistics (PCA, PLS) in conjunction with analytical reference data leads to very good IR and NIR calibration results. For the main essential oil components (e.g. carvacrol, thymol, γ-terpinene, α-bisabolol and β-farnesene) standard errors are in the range of the applied GC reference method. In most cases the multiple coefficients of determination ( R2) are >0.97. Using the IR fingerprint region (900-1400 cm -1) a qualitative discrimination of the individual chemotypes is possible already by visual judgement without to apply any chemometric algorithms.The described rapid and non-destructive methods can be applied in industry to control very easily purifying, blending and redistillation processes of the mentioned essential oils.
Phytochemical composition and in vitro screening of the antimicrobial activity of essential oils on oral pathogenic bacteria.

PubMed

Tardugno, Roberta; Pellati, Federica; Iseppi, Ramona; Bondi, Moreno; Bruzzesi, Giacomo; Benvenuti, Stefania

2018-03-01

In this study, the activity of essential oils (EOs) against microorganisms involved in oral diseases was evaluated. Fourteen EOs were selected and subjected to gas chromatographic analysis, including Illicium verum, Eucaliptus globulus, Eugenia caryophyllata, Leptospermum scoparium, Mentha arvensis, Mentha piperita, Myrtus communis, Salvia officinalis, Melaleuca alternifolia, Rosmarinus officinalis, Lavandula x intermedia, Thymus capitatus and Thymus vulgaris. These EOs were tested for their antimicrobial activity on Streptococcus mutans and Lactobacillus species clinically isolated from dental surgery patients. The antibacterial activity was evaluated by means of the disc diffusion and the minimum inhibitory concentration (MIC). Five EOs, having shown an interesting antimicrobial activity, were selected for a second screening in combination between them and with chlorhexidine. From the second assays, two EO-EO and three EO-chlorhexidine associations gave interesting results as potential constituents of mouthwashes, especially for the contribution of oxygenated monoterpenes, including menthol, thymol and carvacrol.
Lippia origanoides chemotype differentiation based on essential oil GC-MS and principal component analysis.

PubMed

Stashenko, Elena E; Martínez, Jairo R; Ruíz, Carlos A; Arias, Ginna; Durán, Camilo; Salgar, William; Cala, Mónica

2010-01-01

Chromatographic (GC/flame ionization detection, GC/MS) and statistical analyses were applied to the study of essential oils and extracts obtained from flowers, leaves, and stems of Lippia origanoides plants, growing wild in different Colombian regions. Retention indices, mass spectra, and standard substances were used in the identification of 139 substances detected in these essential oils and extracts. Principal component analysis allowed L. origanoides classification into three chemotypes, characterized according to their essential oil major components. Alpha- and beta-phellandrenes, p-cymene, and limonene distinguished chemotype A; carvacrol and thymol were the distinctive major components of chemotypes B and C, respectively. Pinocembrin (5,7-dihydroxyflavanone) was found in L. origanoides chemotype A supercritical fluid (CO(2)) extract at a concentration of 0.83+/-0.03 mg/g of dry plant material, which makes this plant an interesting source of an important bioactive flavanone with diverse potential applications in cosmetic, food, and pharmaceutical products.
Oviposition Deterrent and Larvicidal and Pupaecidal Activity of Seven Essential Oils and their Major Components against Culex quinquefasciatus Say (Diptera: Culicidae): Synergism–antagonism Effects

PubMed Central

Andrade-Ochoa, Sergio; Sánchez-Aldana, Daniela; Chacón-Vargas, Karla Fabiola; Rivera-Chavira, Blanca E.; Camacho, Alejandro D.; Nogueda-Torres, Benjamín

2018-01-01

The larvicidal activity of essential oils cinnamon (Cinnamomum verum J. Presl), Mexican lime (Citrus aurantifolia Swingle) cumin (Cuminum cyminum Linnaeus), clove (Syzygium aromaticum (L.) Merr. & L.M.Perry), laurel (Laurus nobilis Linnaeus), Mexican oregano (Lippia berlandieri Schauer) and anise (Pimpinella anisum Linnaeus)) and their major components are tested against larvae and pupae of Culex quinquefasciatus Say. Third instar larvae and pupae are used for determination of lethality and mortality. Essential oils with more than 90% mortality after a 30-min treatment are evaluated at different time intervals. Of the essential oils tested, anise and Mexican oregano are effective against larvae, with a median lethal concentration (LC50) of 4.7 and 6.5 µg/mL, respectively. Anise essential oil and t-anethole are effective against pupae, with LC50 values of 102 and 48.7 µg/mL, respectively. Oregano essential oil and carvacrol also have relevant activities. A kinetic analysis of the larvicidal activity, the oviposition deterrent effect and assays of the effects of the binary mixtures of chemical components are undertaken. Results show that anethole has synergistic effects with other constituents. This same effect is observed for carvacrol and thymol. Limonene shows antagonistic effect with β-pinene. The high larvicidal and pupaecidal activities of essential oils and its components demonstrate that they can be potential substitutes for chemical compounds used in mosquitoes control programs. PMID:29443951

Larvicidal and acetylcholinesterase inhibitory activities of apiaceae plant essential oils and their constituents against aedes albopictus and formulation development.

PubMed

Seo, Seon-Mi; Jung, Chan-Sik; Kang, Jaesoon; Lee, Hyo-Rim; Kim, Sung-Woong; Hyun, Jinho; Park, Il-Kwon

2015-11-18

This study evaluated the larvicidal activity of 12 Apiaceae plant essential oils and their components against the Asian tiger mosquito, Aedes albopictus, and the inhibition of acetylcholine esterase with their components. Of the 12 plant essential oils tested, ajowan (Trachyspermum ammi), caraway seed (Carum carvi), carrot seed (Daucus carota), celery (Apium graveolens), cumin (Cuminum cyminum), dill (Anethum graveolens), and parsley (Petroselinum sativum) resulted in >90% larval mortality when used at 0.1 mg/mL. Of the compounds identified, α-phellandrene, α-terpinene, p-cymene, (-)-limonene, (+)-limonene, γ-terpinene, cuminaldehyde, neral, (S)-+-carvone, trans-anethole, thymol, carvacrol, myristicin, apiol, and carotol resulted in >80% larval mortality when used at 0.1 mg/mL. Two days after treatment, 24.69, 3.64, and 12.43% of the original amounts of the celery, cumin, and parsley oils, respectively, remained in the water. Less than 50% of the original amounts of α-phellandrene, 1,8-cineole, terpinen-4-ol, cuminaldehyde, and trans-antheole were detected in the water at 2 days after treatment. Carvacrol, α-pinene, and β-pinene inhibited the activity of Ae. albopictus acetylcholinesterase with IC50 values of 0.057, 0.062, and 0.190 mg/mL, respectively. A spherical microemulsion of parsley essential oil-loaded poly(vinyl alcohol) (PVA) was prepared, and the larvicidal activity of this formulation was shown to be similar to that of parsley oil.
Liquid and vapour-phase antifungal activities of essential oils against Candida albicans and non-albicans Candida.

PubMed

Mandras, Narcisa; Nostro, Antonia; Roana, Janira; Scalas, Daniela; Banche, Giuliana; Ghisetti, Valeria; Del Re, Simonetta; Fucale, Giacomo; Cuffini, Anna Maria; Tullio, Vivian

2016-08-30

The management of Candida infections faces many problems, such as a limited number of antifungal drugs, toxicity, resistance of Candida to commonly antifungal drugs, relapse of Candida infections, and the high cost of antifungal drugs. Though azole antifungal agents and derivatives continue to dominate as drugs of choice against Candida infections, there are many available data referring to the anticandidal activity of essential oils. Since we have previous observed a good antimicrobial activity of some essential oils against filamentous fungi, the aim of this study was to extend the research to evaluate the activity of the same oils on Candida albicans, C.glabrata and C.tropicalis clinical strains, as well as the effects of related components. Essential oils selection was based both on ethnomedicinal use and on proved antibacterial and/or antifungal activity of some of these oils. Fluconazole and voriconazole were used as reference drugs. The minimum inhibitory concentration (MIC) and the minimal fungicidal concentration (MFC) of essential oils (thyme red, fennel, clove, pine, sage, lemon balm, and lavender) and their major components were investigated by the broth microdilution method (BM) and the vapour contact assay (VC). Using BM, pine oil showed the best activity against all strains tested, though C.albicans was more susceptible than C.glabrata and C.tropicalis (MIC50-MIC90 = 0.06 %, v/v). On the contrary, sage oil displayed a weak activity (MIC50-MIC90 = 1 %, v/v). Thyme red oil (MIC50-MIC90 ≤ 0.0038 %, v/v for C.albicans and C.tropicalis, and 0.0078- < 0.015 %, v/v for C.glabrata), followed by lemon balm, lavender and sage were the most effective by VC. Carvacrol and thymol showed the highest activity, whereas linalyl acetate showed the lowest activity both by two methods. α-pinene displayed a better activity by BM than VC. Results show a good activity of essential oils, mainly thymus red and pine oils, and their components carvacrol, thymol and α-pinene against Candida spp., including fluconazole/voriconazole resistant strains. These data encourage adequately controlled and randomized clinical investigations. The use in vapour phase could have additional advantages without requiring direct contact, resulting in easy of environmental application such as in hospital, and/or in school.
The chemical composition and trypanocidal activity of volatile oils from Brazilian Caatinga plants.

PubMed

Oliveira de Souza, Larissa Isabela; Bezzera-Silva, Patrícia Cristina; do Amaral Ferraz Navarro, Daniela Maria; da Silva, Alexandre Gomes; Dos Santos Correia, Maria Tereza; da Silva, Márcia Vanusa; de Figueiredo, Regina Celia Bressan Queiroz

2017-12-01

Essential/volatile oils (EOs) from plants used in the traditional medicine are known as a rich source of chemically diverse compounds with relevant biological activities. In this work we analysed the chemical composition and the in vitro effects of EOs from leaves of Eugenia brejoensis (EBEO), Hyptis pectinata (HPEO), Hypenia salzmannii (HSEO), Lippia macrophylla (LMEO) and seeds of Syagrus coronata (SCEO) on Trypanosoma cruzi, the etiological agent of Chagas disease. The EOs were extracted through hydrodistillation and its chemical composition analysed by GC/MS. The trypanocidal activity against epi- and trypomastigotes was evaluated by optical microscopy and the cytotoxicity to mammalian cells by MTT. The effects of EOs on parasite infection in macrophages were estimated by determining the survival index and the percentage of infection inhibition. The cytotoxicity against mammalian cells was compared to those of parasite by determining the Selectivity Index (SI). Overall, 114 compounds were identified: The main constituents of EOS were: δ-cadinene (15.88%), trans-caryophyllene (9.77%) e α-Muurolol (9.42%) for EBEO; trans-caryophyllene (15.24%), bicyclogermacrene (7.33%) e cis-calamenene (7.15%) for HFEO; trans-caryophyllene (30.91%), caryophyllene oxide (13.19%) and spathulenol (5.68%) for HPEO; Xanthoxylin (17.20%) trans-caryophyllene (14.34%) and methyl-eugenol (5.60%) for HSEO; Thymol (49.81%), carvacrol (31.6%) and σ-cimene (10.27%) for LMEO and octanoic acid (38.83%) dodecanoic acid (38.45%) and decanoic acid (20.51%) for SCEO. All the tested oils showed an inhibitory effect on the growth and survival of all forms of T. cruzi and moderate cytotoxicity towards the mammalian cells (100 < CC 50 < 500 μg/mL). The EO of E. brejoensis was the most effective against the parasite presenting higher Selectivity Index for trypo- (SI = 14.45) and amastigote forms (SI = 20.11). Except for SCEO, which was the most cytotoxic for both parasite and mammalian cells, all the oils demonstrated to be more selective for the parasite than the reference drug benznidazole. Taken together our results point the essential oils from Caatinga plants, especially Eugenia brejoensis, as promissory agents for the development of new drugs against Chagas disease. Copyright © 2017 Elsevier Masson SAS. All rights reserved.
Antimicrobial and seasonal evaluation of the carvacrol-chemotype oil from Lippia origanoides kunth.

PubMed

Sarrazin, Sandra Layse F; da Silva, Leomara Andrade; de Assunção, Ana Paula F; Oliveira, Ricardo B; Calao, Victor Y P; da Silva, Rodrigo; Stashenko, Elena E; Maia, José Guilherme S; Mourão, Rosa Helena V

2015-01-23

This study evaluated the influence of seasonal variation on the yield and composition of essential oil of Lippia origanoides occurring in the Middle Rio Amazonas, Brazil, and the impact on its antimicrobial potential. The average oil yield was 1.7% ± 0.2% in the rainy season and 1.6% ± 0.3% in the dry season. Some correlations with climatic parameters were observed. The major components were carvacrol (rainy, 43.5% ± 1.9%; dry, 41.4% ± 2.04%), thymol (rainy, 10.7% ± 1.1%; dry, 10.6% ± 0.9%), p-cymene (rainy, 9.8% ± 0.7%; dry, 10.0% ± 1.4%) and p-methoxythymol (rainy, 9.6% ± 0.8%; dry, 10.4% ± 1.4%). It was found that the antibacterial activity of L. origanoides against Staphylococcus aureus and Escherichia coli was little influenced by the changes in oil composition due to seasonal variation. Against S. aureus, the oil Minimum Inhibitory Concentration (MIC) value was 1.25 μL/mL over ten months. Against E. coli, the oil MIC values ranged from 0.15 μL/mL to 0.31 μL/mL in different months of the year. The Minimum Bactericidal Concentration (MBC) value was 2.5 μL/mL against S. aureus and 1.25 μL/mL against E. coli. The results suggest that the antimicrobial activity identified in the oil remain unchanged for the full year, allowing its medicinal use without any risk of loss or absence of the active principles of the plant.
A Novel in vitro Bioassay to Explore the Repellent Effects of Compounds Against Mosquito Aedes aegypti (Diptera: Culicidae).

PubMed

Rehman, Junaid U; Tabanca, Nurhayat; Khan, Ikhlas A

2016-01-01

Mosquitoes are vectors for many pathogens resulting in many deaths of humans. Repellents play an important role in reducing mosquito bites and the spread of mosquito-borne diseases. Currently, Klun & Debboun (K & D) and human-arm-based bioassay systems are used to identify repellent properties of compounds, extracts, and essential oils. Risks involved with human-arm-based systems are allergic reactions and limited replicates. We are reporting an in vitro bioassay method “NCNPR repellent bioassay (NCNPR-RB)” that can closely simulate the results of the cloth patch bioassay system used to determine repellency against mosquitoes. The NCNPRRB method uses heat to attract mosquito and edible collagen sheets as an alternate to human skin. Multiple plant compounds with documented repellency were tested. DEET (N,N-diethyl-3-methylbenzamide) was used as a positive control. Treatments were prepared in EtOH and applied in dosages ranging from 0.011–1.5mg/cm2 to a 20-cm2 collagen sheet. The number of mosquitoes commencing to bite per probe was recorded visually for 1 min. The minimum effective dosage (mg/cm2) of compounds: DEET (0.021), carvacrol (0.011), thymol (0.013), undecanoic acid (0.023), thymol methyl ether (0.269), and 2-nonanone (>0.375 mg/cm2) determined in NCNPRRB were similar to those reported in literature using a cloth patch bioassay system. The NCNPR-RB can be used to screen compounds with reasonable reproducibility of the data at a faster rate than the cloth patch bioassay, which involves the use of human subjects.
Investigating Chemical Composition and Indications of Hydrosol Soft Drinks (Aromatic Waters) Used in Persian Folk Medicine for Women’s Hormonal and Reproductive Health Conditions

PubMed Central

Hamedi, Azadeh; Afifi, Mehdi; Etemadfard, Hamed

2017-01-01

Hydrosol soft drinks in Persian nutrition culture are produced as side products of the essential oil industry to be used as safe remedies for treatment of some ailments. This study investigated hydrosols for women’s hormonal health conditions. Detailed information was gathered by questionnaires. Chemical constituents of these mono- or poly-herbal hydrosols were identified after liquid/liquid extraction and gas chromatography–mass spectrometry. Hierarchical cluster and K-means analysis (SPSS software) were used to find their relevance. A literature survey was also performed. In most cases, thymol, carvacrol, and carvone were the major constituents except for dill, white horehound, willow, Moderr, and yarrow hydrosols, whose their major components were dill ether, menthol, phenethyl alcohol, linalool, or camphor. Based on clustering methods, some similarities could be found in their constituents with some exceptions. None of them have been studied scientifically before. These investigations may lead to the development of some functional drinks or even new lead components. PMID:28701045
Water Deficit and Seasonality Study on Essential Oil Constituents of Lippia gracilis Schauer Germplasm

PubMed Central

Cruz, Elizangela Mércia de Oliveira; Pinto, Jéssika Andreza Oliveira; Fontes, Saymo Santos; Arrigoni-Blank, Maria de Fátima; Bacci, Leandro; de Jesus, Hugo César Ramos; Santos, Darlisson de Alexandria; Alves, Péricles Barreto; Blank, Arie Fitzgerald

2014-01-01

The aim of this study was to analyze the chemical composition of the essential oil from leaves of Lippia gracilis genotypes, in the dry and rainy seasons, and with and without irrigation. The extraction of essential oil was realized by hydrodistillation in a Clevenger apparatus. The chemical composition analysis was performed using a GC-MS/FID. The leaves of the L. gracilis genotypes provide essential oil with content between 1.25% and 1.92% in the rainy season and 1.42% and 2.70% in the dry season; when irrigation was used the content was between 1.42% and 2.87%, without irrigation contents were between 1.60% and 3.00%. The chemical composition of L. gracilis showed high levels of terpenes. The major constituent of genotypes LGRA-106 was thymol and carvacrol was the major constituent for the other genotypes. Concentrations showed little variation between seasons, demonstrating the stability of the chemical composition of L. gracilis even with different climatic conditions. PMID:25302321
Investigating Chemical Composition and Indications of Hydrosol Soft Drinks (Aromatic Waters) Used in Persian Folk Medicine for Women's Hormonal and Reproductive Health Conditions.

PubMed

Hamedi, Azadeh; Afifi, Mehdi; Etemadfard, Hamed

2017-10-01

Hydrosol soft drinks in Persian nutrition culture are produced as side products of the essential oil industry to be used as safe remedies for treatment of some ailments. This study investigated hydrosols for women's hormonal health conditions. Detailed information was gathered by questionnaires. Chemical constituents of these mono- or poly-herbal hydrosols were identified after liquid/liquid extraction and gas chromatography-mass spectrometry. Hierarchical cluster and K-means analysis (SPSS software) were used to find their relevance. A literature survey was also performed. In most cases, thymol, carvacrol, and carvone were the major constituents except for dill, white horehound, willow, Moderr, and yarrow hydrosols, whose their major components were dill ether, menthol, phenethyl alcohol, linalool, or camphor. Based on clustering methods, some similarities could be found in their constituents with some exceptions. None of them have been studied scientifically before. These investigations may lead to the development of some functional drinks or even new lead components.
Thymol and Carvacrol Affect Hybrid Tilapia through the Combination of Direct Stimulation and an Intestinal Microbiota-Mediated Effect: Insights from a Germ-Free Zebrafish Model.

PubMed

Ran, Chao; Hu, Jun; Liu, Wenshu; Liu, Zhi; He, Suxu; Dan, Bui Chau Truc; Diem, Nguyen Ngoc; Ooi, Ei Lin; Zhou, Zhigang

2016-05-01

Essential oils (EOs) are commonly used as animal feed additives. Information is lacking on the mechanisms driving the beneficial effects of EOs in animals, especially the role played by the intestinal microbiota of the host. The purpose of this study was to clarify the relative contribution of direct effects of EOs on the physiology and immune system of tilapia and indirect effects mediated by the intestinal microbiota by using a germ-free zebrafish model. Juvenile hybrid tilapia were fed a control diet or 1 of 4 treatment diets containing 60-800 mg Next Enhance 150 (NE) (an EO product containing equal levels of thymol and carvacrol)/kg for 6 wk. The key humoral and cellular innate immune parameters were evaluated after the feeding period. In another experiment, the gut microbiota of tilapia fed a control or an NE diet (200 mg/kg) for 2 wk were transferred to 3-d postfertilization (dpf) germ-free (GF) zebrafish, and the expression of genes involved in innate immunity and tight junctions was evaluated in zebrafish at 6 dpf. Lastly, NE was directly applied to 3-dpf GF zebrafish at 3 doses ranging from 0.2 to 20 mg/L, and the direct effect of NE on zebrafish was evaluated after 1 and 3 d. NE supplementation at 200 mg/kg enhanced phagocytosis activity of head kidney macrophages (×1.36) (P < 0.05) and plasma lysozyme activity (×1.69) of tilapia compared with the control (P < 0.001), indicating an immunostimulatory effect. Compared with those colonized with control microbiota, GF zebrafish colonized with NE microbiota showed attenuated induction of immune response marker genes serum amyloid a (Saa; ×0.62), interleukin 1β (Il1β; ×0.29), and interleukin 8 (Il8; ×0.62) (P < 0.05). NE treatment of GF zebrafish at 2 and 20 mg/L for 1 d upregulated the expression of Il1β (×2.44) and Claudin1 (×1.38), respectively (P < 0.05), whereas at day 3 the expression of Occludin2 was higher (×3.30) in the 0.2-mg NE/L group compared with the GF control (P < 0.05). NE may affect the immunity of tilapia through a combination of factors, i.e., primarily through a direct effect on host tissue (immune-stimulating) but also an indirect effect mediated by microbial changes (immune-relieving). © 2016 American Society for Nutrition.
Repellent Activity of Apiaceae Plant Essential Oils and their Constituents Against Adult German Cockroaches.

PubMed

Lee, Hyo-Rim; Kim, Gil-Hah; Choi, Won-Sil; Park, Il-Kwon

2017-04-01

We evaluated the repellent activity of 12 Apiaceae plant essential oils and their components against male and female adult German cockroaches, Blattella germanica L., to find new natural repellents. Of all the plant essential oils tested, ajowan (Trachyspermum ammi Sprague) and dill (Anethum graveolens L.) essential oils showed the most potent repellent activity against male and female adult German cockroaches. Repellent activities of chemicals already identified in active oils were also investigated. Of the compounds identified, carvacrol, thymol, and R-(-)-carvone showed >80% repellent activity against male and female adult German cockroaches at 2.5 µg/cm2. S-(+)-Carvone, (+)-dihydrocarvone, and terpinen-4-ol showed >70% repellent activity against male and female adult German cockroaches at 10 µg/cm2. Our results indicated that Apiaceae plant essential oils and their constituents have good potential as natural repellents against adult German cockroaches. © The Authors 2016. Published by Oxford University Press on behalf of Entomological Society of America. All rights reserved. For Permissions, please email: journals.permissions@oup.com.
Chemical composition and biological activity of the essential oil of Origanum vulgare ssp. hirtum from different areas in the Southern Apennines (Italy).

PubMed

Mancini, Emilia; Camele, Ippolito; Elshafie, Hazem S; De Martino, Laura; Pellegrino, Carlo; Grulova, Daniela; De Feo, Vincenzo

2014-04-01

The chemical composition of the essential oils of Origanum vulgare ssp. hirtum, growing wild in three different localities in the Southern Apennines, was studied by GC-FID and GC/MS analyses. In total, 103 compounds were identified. The oils were mainly composed of phenolic compounds and all oils belonged to the chemotype carvacrol/thymol. The three essential oils were evaluated for their in vitro phytotoxic activity by determining their influence on the germination and initial radicle elongation of Sinapis arvensis L., Phalaris canariensis L., Lepidium sativum L., and Raphanus sativus L. The seed germination and radicle growth were affected in various degrees. Moreover, the antifungal activity of the three essential oils was assayed against three species causing pre- and postharvest fruit decay (Monilinia laxa, M. fructigena, and M. fructicola). At 1000 ppm, the three oils completely inhibited fungal growth. The hemolytic activity of the oils was assayed and showed no effect on the cell membranes of bovine erythrocytes. Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.
Composition, Cytotoxic and Antimicrobial Activities of Satureja intermedia C.A.Mey Essential Oil.

PubMed

Sharifi-Rad, Javad; Sharifi-Rad, Mehdi; Hoseini-Alfatemi, Seyedeh Mahsan; Iriti, Marcello; Sharifi-Rad, Majid; Sharifi-Rad, Marzieh

2015-08-03

In this study, the essential oil (EO) constituents from the aerial parts of Satureja intermedia C.A.Mey were detected by GC and GC/MS. The antimicrobial activity of EO on oral pathogens and its cytotoxicity to human cancer cells were determined by the microbroth dilution method and the crystal violet staining method, respectively. Thirty-nine compounds were identified and the main EO constituents were γ-terpinene (37.1%), thymol (30.2%), p-cymene (16.2%), limonene (3.9%), α-terpinene (3.3%), myrcene (2.5%), germacrene B (1.4%), elemicine (1.1%) and carvacrol (0.5%). The S. intermedia EO showed a concentration-dependent decrease in viability of Hep-G2 (hepatocellular carcinoma) and MCF-7 (breast adenocarcinoma) human cancer cell lines (p < 0.05). Antimicrobial screening of S. intermedia EO demonstrated slight antibacterial and antifungal activities against Streptococcus mutants, S. salivarius, Enterococcus faecalis, Staphylococcus aureus, Candida albicans and C. glabrata. Further preclinical studies are needed to assess the efficacy and safety of S. intermedia EO as a new promising anticancer agent.
Composition, Cytotoxic and Antimicrobial Activities of Satureja intermedia C.A.Mey Essential Oil

PubMed Central

Sharifi-Rad, Javad; Sharifi-Rad, Mehdi; Hoseini-Alfatemi, Seyedeh Mahsan; Iriti, Marcello; Sharifi-Rad, Majid; Sharifi-Rad, Marzieh

2015-01-01

In this study, the essential oil (EO) constituents from the aerial parts of Satureja intermedia C.A.Mey were detected by GC and GC/MS. The antimicrobial activity of EO on oral pathogens and its cytotoxicity to human cancer cells were determined by the microbroth dilution method and the crystal violet staining method, respectively. Thirty-nine compounds were identified and the main EO constituents were γ-terpinene (37.1%), thymol (30.2%), p-cymene (16.2%), limonene (3.9%), α-terpinene (3.3%), myrcene (2.5%), germacrene B (1.4%), elemicine (1.1%) and carvacrol (0.5%). The S. intermedia EO showed a concentration-dependent decrease in viability of Hep-G2 (hepatocellular carcinoma) and MCF-7 (breast adenocarcinoma) human cancer cell lines (p < 0.05). Antimicrobial screening of S. intermedia EO demonstrated slight antibacterial and antifungal activities against Streptococcus mutants, S. salivarius, Enterococcus faecalis, Staphylococcus aureus, Candida albicans and C. glabrata. Further preclinical studies are needed to assess the efficacy and safety of S. intermedia EO as a new promising anticancer agent. PMID:26247936
The properties of chitosan and gelatin films incorporated with ethanolic red grape seed extract and Ziziphora clinopodioides essential oil as biodegradable materials for active food packaging.

PubMed

Shahbazi, Yasser

2017-06-01

The aim of this study was to improve different characteristics including antibacterial, antioxidant, physical and mechanical properties of chitosan (Ch) and gelatin (Ge) films by incorporating Ziziphora clinopodioides essential oil (ZEO; 0 and 1% v/w) and ethanolic grape seed extract (GSE; 0 and 1% v/w). The main compounds of the ZEO were carvacrol (65.22%) and thymol (19.51%). According to our findings, addition of aforementioned materials could improve total phenolic content, antibacterial and antioxidant activities, thickness and also water vapor barrier property. ZEO and GSE reduces swelling index, tensile strength, puncture force and puncture deformation of Ch and Ge films. Pure Ch and Ge films had slightly yellow and white appearances, respectively, while films incorporated with GSE in combination with ZEO had grey appearances. This study indicated the some benefits of addition of ZEO and GSE into Ch and Ge films and their potentials for application as biodegradable active packaging. Copyright © 2017 Elsevier B.V. All rights reserved.
Chemical composition and bioactivity of different oregano (Origanum vulgare) extracts and essential oil.

PubMed

Teixeira, Bárbara; Marques, António; Ramos, Cristina; Serrano, Carmo; Matos, Olívia; Neng, Nuno R; Nogueira, José M F; Saraiva, Jorge Alexandre; Nunes, Maria Leonor

2013-08-30

There is a growing interest in industry to replace synthetic chemicals by natural products with bioactive properties. Aromatic plants are excellent sources of bioactive compounds that can be extracted using several processes. As far as oregano is concerned, studies are lacking addressing the effect of extraction processes in bioactivity of extracts. This study aimed to characterise the in vitro antioxidant and antibacterial properties of oregano (Origanum vulgare) essential oil and extracts (in hot and cold water, and ethanol), and the chemical composition of its essential oil. The major components of oregano essential oil were carvacrol, β-fenchyl alcohol, thymol, and γ-terpinene. Hot water extract had the strongest antioxidant properties and the highest phenolic content. All extracts were ineffective in inhibiting the growth of the seven tested bacteria. In contrast, the essential oil inhibited the growth of all bacteria, causing greater reductions on both Listeria strains (L. monocytogenes and L. innocua). O. vulgare extracts and essential oil from Portuguese origin are strong candidates to replace synthetic chemicals used by the industry. © 2013 Society of Chemical Industry.
Low temperature and binding to food components inhibit the antibacterial activity of carvacrol against Listeria monocytogenes in steak tartare.

PubMed

Veldhuizen, Edwin J A; Creutzberg, T Olaf; Burt, Sara A; Haagsman, Henk P

2007-09-01

Carvacrol is a major component of thyme and oregano essential oils and has potential uses as a food preservative. The effect of carvacrol on the growth of Listeria monocytogenes was investigated in vitro and in steak tartare. Carvacrol had strong antilisterial activity in growth medium (MIC = 1.6 mM), but no effect was observed when carvacrol was tested in steak tartare. There were two reasons for this reduced activity: the antilisterial activity of carvacrol was strongly reduced at lower temperatures (10 versus 30 degrees C), and the presence of food components interfered with the activity of carvacrol. Both bovine serum albumin and egg yolk inhibited carvacrol activity at > 0.2% (wt/vol) in growth medium. For the first time, carvacrol was found to bind to albumin, suggesting that the reduced antilisterial activity of carvacrol in foods such as dairy products and uncooked meats is the result of fewer free unbound carvacrol molecules available to interact with bacteria.
Antimicrobial Activity and Chemical Composition of Three Essential Oils Extracted from Mediterranean Aromatic Plants.

PubMed

Elshafie, Hazem S; Sakr, Shimaa; Mang, Stefania M; Belviso, Sandra; De Feo, Vincenzo; Camele, Ippolito

2016-11-01

There is a growing interest in essential oils (EOs) as possible alternatives for traditional chemical pesticides. This study was carried out to characterize the chemical composition of the three EOs extracted from Verbena officinalis, Majorana hortensis, and Salvia officinalis using gas chromatography (GC) and GC-mass spectrometry (GC-MS) and to evaluate in vitro their efficacy against some phyto or human pathogens. The antifungal activity was investigated against Colletotrichum acutatum and Botrytis cinerea in comparison with Azoxystrobin as a large spectrum fungicide. Antibacterial activity was evaluated against Bacillus megaterium, Bacillus mojavensis, and Clavibacter michiganensis (G+ve) and Escherichia coli, Xanthomonas campestris, Pseudomonas savastanoi, and P. syringae pv. phaseolicola (G-ve) compared to a synthetic antibiotic tetracycline. Minimum inhibitory concentration was evaluated against the above tested fungi using 96-well microplate method. Results showed that the chemical structure of the three studied EOs was mainly composed of monoterpene compounds and all oils belong to the chemotype carvacrol/thymol. Results of GC analysis identified 64 compounds, which were identified based on their mass to charge ratio. Furthermore, the different concentrations of studied EOs inhibited the growth of tested microorganism in a dose-dependent manner.
Evaluation of the Cytotoxicity of Satureja spicigera and Its Main Compounds

PubMed Central

Gohari, Ahmad Reza; Ostad, Seyed Nasser; Moradi-Afrapoli, Fahimeh; Malmir, Maryam; Tavajohi, Shohreh; Akbari, Hassan; Saeidnia, Soodabeh

2012-01-01

Satureja spicigera (Lamiaceae) grows wildly in Northwest of Iran. In this study, bioassay-guided isolation and identification of the main compounds has been reported using various chromatographic methods and comparison of their spectral data with those reported in the literature. Brine shrimp lethality and four cancerous cell lines HT29/219, Caco2, NIH-3T3, and T47D were used for cytotoxicity evaluations. From the aerial parts of S. spicigera, nine known compounds including two flavanones, 5,7,3′,5′-tetrahydroxy flavanone (8) and 5,4′-dihydroxy-3′-methoxyflavanone-7-(6′′-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (9), one dihydrochalcone, nubigenol (7), together with thymoquinone (1), thymol (2), carvacrol (3), β-sitosterol (4), ursolic acid (5) and oleanolic acid (6) were identified. Among the isolated chalcone and flavanones, compound 8 was effective against Artemia salina larva (LC50= 2 μg/mL) and only the compound 9 demonstrated IC50 value of 98.7 μg/mL on the T47D (human, breast, ductal carcinoma). Other compounds did not show significant inhibition of the cell growth. PMID:22623883
Radiosensitization: enhancing the radiation inactivation of foodborne bacteria

NASA Astrophysics Data System (ADS)

Borsa, J.; Lacroix, M.; Ouattara, B.; Chiasson, F.

2004-09-01

Irradiation of meat products to kill pathogens can be limited by radiation-induced detriment of sensory quality. Since such detriment is directly related to dose, one approach to reduce it is by devising means to lower the dose of radiation required for processing. Increasing the radiation sensitivity of the target microorganisms would lower the dose required for a given level of microbial kill. In this work, the radiation sensitivities of inoculated Escherichia coli and Salmonella typhi in ground beef were examined under a variety of conditions. Results showed that specific manipulations of treatment conditions significantly increased the radiation sensitivity of the test organisms, ranging from a few percent to several-fold reduction in D10. In particular, radiation sensitization could be effected by certain additives, including carvacrol, thymol and trans-cinnamaldehyde, and also by certain compositions of modified atmosphere in the package headspace. A combination of additives and modified atmosphere effected a greater radiosensitization effect than could be achieved by either factor applied alone. Radiosensitization could be demonstrated with irradiation of either fresh or frozen ground meat. The radiosensitization phenomenon may be of practical utility in enhancing the technical effectiveness and feasibility of irradiation of a variety of meat and other food products.
Phytochemical Prospection and Modulation of Antibiotic Activity In Vitro by Lippia origanoides H.B.K. in Methicillin Resistant Staphylococcus aureus

PubMed Central

Medeiros Barreto, Humberto; Cerqueira Fontinele, Filipe; Pereira de Oliveira, Aldeídia; Arcanjo, Daniel Dias Rufino; Cavalcanti dos Santos, Bernadete Helena; de Abreu, Aislan Pereira Lira; Douglas Melo Coutinho, Henrique; Alves Carvalho da Silva, Romezio; Oliveira de Sousa, Taciana; Freire de Medeiros, Maria das Graças; Lopes Citó, Antonia Maria das Graças; Dantas Lopes, José Arimateia

2014-01-01

The Lippia origanoides H.B.K. ethanol extract (LOEE) and hexane (LOHEX), dichloromethane (LODCM), and ethyl acetate (LOEA) fractions were tested for their antimicrobial activity alone or in combination with antibiotics against a methicillin resistant Staphylococcus aureus (MRSA) strain. The natural products did not show antimicrobial activity against multidrug resistant strain at the clinically significant concentrations tested. However, a modulatory effect in the antibacterial activity of the neomycin and amikacin was verified when LOEE, LOHEX and LODCM were added to the growth medium at subinhibitory concentrations. A similar modulation was found when the natural products were changed for chlorpromazine, an inhibitor of bacterial efflux pumps, suggesting the involvement of resistance mediated by efflux system in the MRSA tested. The fractions LOHEX and LODCM showed a modulatory activity bigger than their majority compounds (carvacrol, thymol, and naringenin), indicating that this activity is not due to their majority compounds only, but it is probably due to a synergism between their chemical components. These results indicate that L. origanoides H.B.K. can be a source of phytochemicals able to modify the phenotype of resistance to aminoglycosides in MRSA. PMID:24683545

Biopreservation of hamburgers by essential oil of Zataria multiflora.

PubMed

Samadi, N; Sharifan, A; Emam-Djomeh, Z; Sormaghi, M H Salehi

2012-01-01

Hamburgers with high nutrient supply and a loosely-packed structure present favourable conditions for microbial growth. In this study, the chemical composition and antimicrobial activity of the essential oil of Zataria multiflora and its potential application as a natural preservative in reducing the indigenous microbial population of hamburgers were investigated. Carvacrol, thymol and linalool were found to be the most abundant constituents of the essential oil using GC-MS analysis. The essential oil exhibited strong antibacterial activity against Gram-positive and Gram-negative bacteria. Addition of Z. multiflora essential oil in concentrations higher than MIC values influenced the microbial population of hamburgers stored at 25°C, 4°C and -12°C. The significant results of this study are our observations that the use of Z. multiflora essential oil at 0.05% v/w increases the time needed for the natural microflora of hamburgers to reach concentrations able to produce a perceivable spoilage at refrigerator and room temperatures without any inverse effect on their sensory attributes. Freezing of essential oil-treated hamburgers may also reduce the risk of diseases associated with consumption of under-cooked hamburgers through significant microbial reduction by more than 3 log.
Therapeutic Potential of Zataria multiflora Boiss in Treatment of Irritable Bowel Syndrome (IBS).

PubMed

Mahboubi, Mohaddese

2018-01-15

Irritable Bowel syndrome (IBS), the most common chronic functional gastrointestinal disorder, is categorized as IBS-C and IBS-D, which are equivalent to Ghoolenj Rihi and Maghs Rihi in Iranian traditional medicine. One of the main applications of Zataria multiflora Boiss in traditional medicine is its efficacy in the gastrointestinal tract with symptoms such as IBS. The aim of this study was to evaluate the efficacy of Zataria multiflora essential oil in management of IBS. We used all the accessible references (electronic and published books, theses, and reports) to write this article. The results of our investigation show that the majority of gas chromatography-mass spectrometry (GC-MS) analyses exhibited carvacrol and thymol as the main components of Zataria multiflora essential oil, and 60 drops oral daily dose of Z. multiflora essential oil (2%) can relieve the symptoms of IBS without any adverse effects. The pharmacological studies confirmed the analgesic, anti-inflammatory, antispasm and antiulcer effects of Z. multiflora essential oils and main components. According to the results of studies, oral Z. multiflora essential oil (2%) is a good candidate for management of IBS, but more studies are required to better understand its efficacies.
Dittany of Crete: a botanical and ethnopharmacological review.

PubMed

Liolios, Christos C; Graikou, Konstantia; Skaltsa, Eleni; Chinou, Ioanna

2010-09-15

Origanum dictamnus (Lamiaceae family), an endemic plant of the Greek island of Crete, is widely used as a traditional medicine since antiquity, all over Europe. The aim of the present review is to present comprehensive information of the plant's botanical taxonomy and morphology, as well as of the chemical constituents, biological and pharmacological research on O. dictamnus, which will be presented and critically evaluated. The paper also highlights particularly interesting aspects and common medicinal uses not previously described in the specific ethnobotanical literature. An increasing number of chemical and pharmacological studies have been reported recently, some of which strongly support its traditional medicinal uses against various illnesses such as sore throat, cough and gastric ulcer. A variety of compounds, including flavonoids, lipids and terpenoids (mainly carvacrol and thymol) have been identified from the plant. Current studies have showed that the extracts, the essential oil, as well as their active principles possess several pharmacological properties, like antimicrobial, antioxidant and anti-ulcer ones. The recent scientific data and the rich historical evidence of its medicinal uses could support further research as well as its use as a safe herbal medicinal product. Copyright 2010 Elsevier Ireland Ltd. All rights reserved.
Carvacrol modulates voltage-gated sodium channels kinetics in dorsal root ganglia.

PubMed

Joca, Humberto Cavalcante; Vieira, Daiana Cardoso Oliveira; Vasconcelos, Aliny Perreira; Araújo, Demetrius Antônio Machado; Cruz, Jader Santos

2015-06-05

Recent studies have shown that many of plant-derived compounds interact with specific ion channels and thereby modulate many sensing mechanisms, such as nociception. The monoterpenoid carvacrol (5-isopropyl-2-methylphenol) has an anti-nociceptive effect related to a reduction in neuronal excitability and voltage-gated Na(+) channels (NaV) inhibition in peripheral neurons. However, the detailed mechanisms of carvacrol-induced inhibition of neuronal NaV remain elusive. This study explores the interaction between carvacrol and NaV in isolated dorsal root ganglia neurons. Carvacrol reduced the total voltage-gated Na(+) current and tetrodotoxin-resistant (TTX-R) Na(+) current component in a concentration-dependent manner. Carvacrol accelerates current inactivation and induced a negative-shift in voltage-dependence of steady-state fast inactivation in total and TTX-R Na(+) current. Furthermore, carvacrol slowed the recovery from inactivation. Carvacrol provoked a leftward shift in both the voltage-dependence of steady-state inactivation and activation of the TTX-R Na(+) current component. In addition, carvacrol-induced inhibition of TTX-R Na(+) current was enhanced by an increase in stimulation frequency and when neurons were pre-conditioned with long depolarization pulse (5s at -50 mV). Taken all results together, we herein demonstrated that carvacrol affects NaV gating properties. The present findings would help to explain the mechanisms underlying the analgesic activity of carvacrol. Copyright © 2015 Elsevier B.V. All rights reserved.
Effect of soil application of humic acid on nutrients uptake, essential oil and chemical compositions of garden thyme (Thymus vulgaris L.) under greenhouse conditions.

PubMed

Noroozisharaf, Alireza; Kaviani, Maryam

2018-05-01

Humic acid is natural biological organic, which has a high effect on plant growth and quality. However, the mechanisms of the promoting effect of humic acid on the volatile composition were rarely reported. In this study, the effects of soil application of humic acid on the chemical composition and nutrients uptake of Thymus vulgaris were investigated. Treatments comprised 0, 50, 75 and 100 g m -2 . Essential oil was extracted by hydrodistillation and analyzed using GC-MS and GC-FID. Essential oil content was enhanced by increase of the humic acid level and its content ranged from 0.8% (control) to 2.0% (75 g m -2 ). Thirty-two volatile compounds were identified and these compounds were considerably affected by humic acid. The highest percentage of thymol (74.15%), carvacrol (6.20%), p -cymene (4.24%), borneol (3.42%), trans -caryophyllene (1.70%) and cis -sabinene hydrate (1.35%) as major compounds were observed in T. vulgaris under 100 g m -2 humic acid. There was a linear relationship ( R 2 = 97%) between humic acid levels and thymol as a major compound. The oils were dominated by oxygenated monoterpenes followed by monoterpene hydrocarbons and sesquiterpene hydrocarbons. Based on the path coefficient analysis, the highest direct effects on essential oil content were observed in monoterpene esters (3.465) and oxygenated sesquiterpenes (3.146). The humic acid application also enhanced the uptake of N, P, K, Mg and Fe in garden thyme. The highest N (2.42%), P (0.75%), K (2.63%), Mg (0.23%) and Fe (1436.58 ppm) were observed in medium supplemented with 100 g m -2 humic acid. In all, the utilization of humic acid could positively change nutrients uptake, essential oil content and its major constituents in T. vulgaris .
Antimicrobial Carvacrol in Solution Blow-Spun Fish-Skin Gelatin Nanofibers.

PubMed

Liu, Fei; Saricaoglu, Furkan Türker; Avena-Bustillos, Roberto J; Bridges, David F; Takeoka, Gary R; Wu, Vivian C H; Chiou, Bor-Sen; Wood, Delilah F; McHugh, Tara H; Zhong, Fang

2018-04-01

Carvacrol is a volatile monoterpenic phenol and main component of oregano essential oil that shows nonspecific antimicrobial activity against foodborne pathogenic bacteria. Fish-skin gelatin (FSG) nanofibers encapsulating carvacrol (15%, 20%, 25%, and 30%, w/w FSG) were successfully prepared via solution blow-spinning (SBS) technique using lecithin (2.475% wb) as the surfactant. FSG emulsions with lower carvacrol ratios (5% and 10%) showed higher values in particle size and surface tension as well as lower values in viscosity and modulus, which led to failure of maintaining nanofibers shape. The formed carvacrol-FSG nanofibers showed round and smooth morphologies with average fiber diameters ranging from 103.2 to 138.1 nm as the carvacrol ratio increased from 15% to 30%. Carvacrol was evenly dispersed within the interior of nanofiber matrix. All carvacrol-FSG nanofibers showed inhibitive effects against the growth of Escherichia coli, Salmonella enterica, and Listeria monocytogenes. Moreover, nanofibers with lower carvacrol ratios showed bigger inhibition zones for E. coli and L. monocytogenes (20 mm compared with 12.5 mm for lowest to highest carvacrol ratios, respectively). Nanofibers stored at 20 °C (51% RH) showed better retention (40% to 60%) for carvacrol during the first 4 weeks of storage, while nanofibers stored at 2 °C (70% RH) showed better retention (10% to 30%) at the end of storage. Results obtained in the study may help with antimicrobial carvacrol addition levels for gelatin fiber preparation using solution blow spinning (SBS) method. SBS gelatin fibers with added antimicrobials have potential applications for food packaging and medical wound dressing. © 2018 Institute of Food Technologists®.
Preparation and characterization of potato starch-thymol dispersion and film as potential antioxidant and antibacterial materials.

PubMed

Davoodi, Mina; Kavoosi, Gholamreza; Shakeri, Raheleh

2017-11-01

The antioxidant/antimicrobial capacity and physical properties of potato starch dispersions enriched with polysorbate-thymol micelle were investigated. Results showed that potato starch have radical scavenging and antibacterial activities only in the presence of polysorbate-thymol but with lower level than polysorbate-thymol alone. The decrease in the antioxidant and antibacterial activities may be attributed to the encapsulation of thymol in the starch chain. Polysorbate-thymol caused a decrease in the particle size and viscosity and an increase in the zeta potential of the starch dispersions. Futhermore, polysorbate-thymol leads to a decrease in the tensile strength, rigidity and swelling, and an increase in the flexibility, solubility and water vapour permeability of the starch films. Atomic force microscopy revealed polysorbate-thymol micelles in the film matrix enclosed by polysaccharide crystal. Scanning electron microscope analysis indicated that polysorbate-thymol caused a coarse film microstructure with the distributed crack in the film matrix. Based on the results, the antioxidant and antibacterial activities of the starch-polysorbate-thymol make starch film suitable for food packaging and preservation. Copyright © 2017 Elsevier B.V. All rights reserved.
Physical characterization and antioxidant activity of thymol solubilized Tween 80 micelles

PubMed Central

Deng, Ling-Li; Taxipalati, Maierhaba; Que, Fei; Zhang, Hui

2016-01-01

Attempts were made to solubilize thymol in Tween 80 micelle to study the solubilization mechanism of thymol and the effect of solubilization on its antioxidant activity. The maximum solubilized concentration of thymol in a 2.0% (w/v) Tween 80 micelle solution is 0.2 wt%. There was no significant difference in Z-average diameter between the empty micelles and thymol solubilized micelles. 1H NMR spectra indicated that 3-H and 4-H on the benzene ring of thymol interacted with the ester group between the hydrophilic head group and the hydrophobic tail group of Tween 80 by Van der Waals’ force. Ferric reducing antioxidant potential (FRAP) and cupric ion reducing antioxidant capacity (CUPRAC) assays showed that the reducing antioxidant activity of free thymol did not change after solubilized in Tween 80 micelles. Compared to free thymol, the solubilized thymol showed higher activities to scavenge DPPH (2,2-diphenyl-1-picrylhydrazyl) and hydroxyl radicals. The present study suggested a possible preparation of thymol-carrying micelles with enhanced antioxidant activities that could be applied in food beverages. PMID:27905567
Physical characterization and antioxidant activity of thymol solubilized Tween 80 micelles.

PubMed

Deng, Ling-Li; Taxipalati, Maierhaba; Que, Fei; Zhang, Hui

2016-12-01

Attempts were made to solubilize thymol in Tween 80 micelle to study the solubilization mechanism of thymol and the effect of solubilization on its antioxidant activity. The maximum solubilized concentration of thymol in a 2.0% (w/v) Tween 80 micelle solution is 0.2 wt%. There was no significant difference in Z-average diameter between the empty micelles and thymol solubilized micelles. 1 H NMR spectra indicated that 3-H and 4-H on the benzene ring of thymol interacted with the ester group between the hydrophilic head group and the hydrophobic tail group of Tween 80 by Van der Waals' force. Ferric reducing antioxidant potential (FRAP) and cupric ion reducing antioxidant capacity (CUPRAC) assays showed that the reducing antioxidant activity of free thymol did not change after solubilized in Tween 80 micelles. Compared to free thymol, the solubilized thymol showed higher activities to scavenge DPPH (2,2-diphenyl-1-picrylhydrazyl) and hydroxyl radicals. The present study suggested a possible preparation of thymol-carrying micelles with enhanced antioxidant activities that could be applied in food beverages.
Physical characterization and antioxidant activity of thymol solubilized Tween 80 micelles

NASA Astrophysics Data System (ADS)

Deng, Ling-Li; Taxipalati, Maierhaba; Que, Fei; Zhang, Hui

2016-12-01

Attempts were made to solubilize thymol in Tween 80 micelle to study the solubilization mechanism of thymol and the effect of solubilization on its antioxidant activity. The maximum solubilized concentration of thymol in a 2.0% (w/v) Tween 80 micelle solution is 0.2 wt%. There was no significant difference in Z-average diameter between the empty micelles and thymol solubilized micelles. 1H NMR spectra indicated that 3-H and 4-H on the benzene ring of thymol interacted with the ester group between the hydrophilic head group and the hydrophobic tail group of Tween 80 by Van der Waals’ force. Ferric reducing antioxidant potential (FRAP) and cupric ion reducing antioxidant capacity (CUPRAC) assays showed that the reducing antioxidant activity of free thymol did not change after solubilized in Tween 80 micelles. Compared to free thymol, the solubilized thymol showed higher activities to scavenge DPPH (2,2-diphenyl-1-picrylhydrazyl) and hydroxyl radicals. The present study suggested a possible preparation of thymol-carrying micelles with enhanced antioxidant activities that could be applied in food beverages.
Carvacrol Codrugs: A New Approach in the Antimicrobial Plan

PubMed Central

Fornasari, Erika; Di Stefano, Antonio; Cerasa, Laura Serafina; Marinelli, Lisa; Turkez, Hasan; Di Campli, Emanuela; Di Bartolomeo, Soraya; Robuffo, Iole; Cellini, Luigina

2015-01-01

Objective The increasing prevalence of antibiotic-resistant bacterial infections led to identify alternative strategies for a novel therapeutic approach. In this study, we synthesized ten carvacrol codrugs – obtained linking the carvacrol hydroxyl group to the carboxyl moiety of sulphur-containing amino acids via an ester bond – to develop novel compounds with improved antimicrobial and antibiofilm activities and reduced toxicity respect to carvacrol alone. Method All carvacrol codrugs were screened against a representative panel of Gram positive (S. aureus and S. epidermidis), Gram negative (E. coli and P. aeruginosa) bacterial strains and C. albicans, using broth microdilution assays. Findings Results showed that carvacrol codrug 4 possesses the most notable enhancement in the anti-bacterial activity displaying MIC and MBC values equal to 2.5 mg/mL for all bacterial strains, except for P. aeruginosa ATCC 9027 (MIC and MBC values equal to 5 mg/mL and 10 mg/mL, respectively). All carvacrol codrugs 1-10 revealed good antifungal activity against C. albicans ATCC 10231. The cytotoxicity assay showed that the novel carvacrol codrugs did not produce human blood hemolysis at their MIC values except for codrugs 8 and 9. In particular, deepened experiments performed on carvacrol codrug 4 showed an interesting antimicrobial effect on the mature biofilm produced by E. coli ATCC 8739, respect to the carvacrol alone. The antimicrobial effects of carvacrol codrug 4 were also analyzed by TEM evidencing morphological modifications in S. aureus, E. coli, and C. albicans. Conclusion The current study presents an insight into the use of codrug strategy for developing carvacrol derivatives with antibacterial and antibiofilm potentials, and reduced cytotoxicity. PMID:25859852
The Natural Antimicrobial Carvacrol Inhibits Quorum Sensing in Chromobacterium violaceum and Reduces Bacterial Biofilm Formation at Sub-Lethal Concentrations

PubMed Central

Burt, Sara A.; Ojo-Fakunle, Victoria T. A.; Woertman, Jenifer; Veldhuizen, Edwin J. A.

2014-01-01

The formation of biofilm by bacteria confers resistance to biocides and presents problems in medical and veterinary clinical settings. Here we report the effect of carvacrol, one of the major antimicrobial components of oregano oil, on the formation of biofilms and its activity on existing biofilms. Assays were carried out in polystyrene microplates to observe (a) the effect of 0–0.8 mM carvacrol on the formation of biofilms by selected bacterial pathogens over 24 h and (b) the effect of 0–8 mM carvacrol on the stability of pre-formed biofilms. Carvacrol was able to inhibit the formation of biofilms of Chromobacterium violaceum ATCC 12472, Salmonella enterica subsp. Typhimurium DT104, and Staphylococcus aureus 0074, while it showed no effect on formation of Pseudomonas aeruginosa (field isolate) biofilms. This inhibitory effect of carvacrol was observed at sub-lethal concentrations (<0.5 mM) where no effect was seen on total bacterial numbers, indicating that carvacrol's bactericidal effect was not causing the observed inhibition of biofilm formation. In contrast, carvacrol had (up to 8 mM) very little or no activity against existing biofilms of the bacteria described, showing that formation of the biofilm also confers protection against this compound. Since quorum sensing is an essential part of biofilm formation, the effect of carvacrol on quorum sensing of C. violaceum was also studied. Sub-MIC concentrations of carvacrol reduced expression of cviI (a gene coding for the N-acyl-L-homoserine lactone synthase), production of violacein (pigmentation) and chitinase activity (both regulated by quorum sensing) at concentrations coinciding with carvacrol's inhibiting effect on biofilm formation. These results indicate that carvacrol's activity in inhibition of biofilm formation may be related to the disruption of quorum sensing. PMID:24691035
Estrous cycle affects the neurochemical and neurobehavioral profile of carvacrol-treated female rats

DOE Office of Scientific and Technical Information (OSTI.GOV)

Trabace, L., E-mail: trabace@unifg.it; Zotti, M.; Morgese, M.G.

2011-09-01

Carvacrol is the major constituent of essential oils from aromatic plants. It showed antimicrobial, anticancer and antioxidant properties. Although it was approved for food use and included in the chemical flavorings list, no indication on its safety has been estimated. Since the use of plant extracts is relatively high among women, aim of this study was to evaluate carvacrol effects on female physiology and endocrine profiles by using female rats in proestrus and diestrus phases. Serotonin and metabolite tissue content in prefrontal cortex and nucleus accumbens, after carvacrol administration (0.15 and 0.45 g/kg p.o.), was measured. Drug effects in behavioralmore » tests for alterations in motor activity, depression, anxiety-related behaviors and endocrine alterations were also investigated. While in proestrus carvacrol reduced serotonin and metabolite levels in both brain areas, no effects were observed in diestrus phase. Only in proestrus phase, carvacrol induced a depressive-like behavior in forced swimming test, without accompanying changes in ambulation. The improvement of performance in FST after subchronic treatment with fluoxetine (20 mg/kg) suggested a specific involvement of serotonergic system. No differences were found across the groups with regard to self-grooming behavior. Moreover, in proestrus phase, carvacrol reduced only estradiol levels without binding hypothalamic estradiol receptors. Our study showed an estrous-stage specific effect of carvacrol on depressive behaviors and endocrine parameters, involving serotonergic system. Given the wide carvacrol use not only as feed additive, but also as cosmetic essence and herbal remedy, our results suggest that an accurate investigation on the effects of its chronic exposure is warranted. - Highlights: > Carvacrol induced a depressive-like phenotype in rats, depending on ovarian cyclicity. > Carvacrol selectively reduced serotonin content in female rats in proestrus phase. > Carvacrol reduced serotonin levels in areas belonging to the emotional circuit. > Carvacrol reduced plasma estradiol levels only during the proestrus phase.« less
Iron-Induced Virulence of Salmonella enterica Serovar Typhimurium at the Intestinal Epithelial Interface Can Be Suppressed by Carvacrol

PubMed Central

Kortman, Guus A. M.; Roelofs, Rian W. H. M.; Swinkels, Dorine W.; de Jonge, Marien I.; Burt, Sara A.

2014-01-01

Oral iron therapy can increase the abundance of bacterial pathogens, e.g., Salmonella spp., in the large intestine of African children. Carvacrol is a natural compound with antimicrobial activity against various intestinal bacterial pathogens, among which is the highly prevalent Salmonella enterica serovar Typhimurium. This study aimed to explore a presumed interaction between carvacrol and bacterial iron handling and to assess the potential of carvacrol in preventing the increase of bacterial pathogenicity during high iron availability. S. Typhimurium was cultured with increasing concentrations of iron and carvacrol to study the effects of these combined interventions on growth, adhesion to intestinal epithelial cells, and iron uptake/influx in both bacterial and epithelial cells. In addition, the ability of carvacrol to remove iron from the high-affinity ligand transferrin and an Fe-dye complex was examined. Carvacrol retarded growth of S. Typhimurium at all iron conditions. Furthermore, iron-induced epithelial adhesion was effectively reduced by carvacrol at high iron concentrations. The reduction of growth and virulence by carvacrol was not paralleled by a change in iron uptake or influx into S. Typhimurium. In contrast, bioavailability of iron for epithelial cells was moderately decreased under these conditions. Further, carvacrol was shown to lack the properties of an iron binding molecule; however, it was able to weaken iron-ligand interactions by which it may possibly interfere with bacterial virulence. In conclusion, our in vitro data suggest that carvacrol has the potential to serve as a novel dietary supplement to prevent pathogenic overgrowth and colonization in the large intestine during oral iron therapy. PMID:24379194
Comparative effect of thymol or its glucose conjugate, thymol-β-D-glucopyranoside, on Campylobacter in avian gut contents.

PubMed

Epps, Sharon V R; Harvey, Roger B; Byrd, J Allen; Petrujkić, Branko T; Sedej, Ivana; Beier, Ross C; Phillips, Timothy D; Hume, Michael E; Anderson, Robin C; Nisbet, David J

2015-01-01

Campylobacter jejuni is an important human food-borne pathogen that can contaminate meat and poultry during processing. Consequently, strategies are sought to reduce the carriage of C. jejuni in food animals before they arrive at the abattoir. Thymol is a natural product that reduces survivability of Campylobacter in vitro, but its rapid absorption from the proximal alimentary tract limits its bactericidal efficacy in vivo. Thymol-β-D-glucopyranoside is more resistant to absorption than free thymol, but its administration to chickens has not been reported. In the present studies, 1 mM thymol-β-D-glucopyranoside was shown to exhibit near equal anti-Campylobacter activity as 1 mM thymol when incubated anaerobically in avian crop or cecal contents in vitro, resulting in reductions of 1.10-2.32 log10 colony forming units mL(-1) in C. jejuni concentrations after 24 h incubation. In a follow-up live animal study, oral administration of thymol-β-D-glucopyranoside, but not free thymol, significantly lowered (>10-fold) recovery of Campylobacter from the crop of market-aged broilers when compared to placebo-treated controls (n = 6 broilers/treatment). Neither thymol-β-D-glucopyranoside nor thymol affected recovery of Campylobacter from cecal contents of the treated broilers. These results indicate that rapid absorption or passage of free thymol from the crop precluded its anti-Campylobacter activity at this site and throughout the entire gastrointestinal tract. Conversely, lower recovery of Campylobacter from the crop of birds treated with thymol-β-D-glucopyranoside indicates this conjugate was retained and able to be hydrolyzed to biologically active free thymol at this site as intended, yet was not sufficiently protected to allow passage of efficacious amounts of the intact glycoside to the lower gut. Nevertheless, these results warrant further research to see if higher doses or encapsulation of thymol-β-D-glucopyranoside or similar glycosides may yield an efficacious additive to reduce carriage of Campylobacter as well as other pathogens throughout the avian gut.
Thymol nanoemulsified by whey protein-maltodextrin conjugates: the enhanced emulsifying capacity and antilisterial properties in milk by propylene glycol.

PubMed

Xue, Jia; Davidson, P Michael; Zhong, Qixin

2013-12-26

The objective of this research was to enhance the capability of whey protein isolate-maltodextrin conjugates in nanoemulsifying thymol using propylene glycol to improve antilisterial properties in milk. Thymol was predissolved in PG and emulsified in 7% conjugate solution. Transparent dispersions with mean diameters of <30 nm were observed up to 1.5%w/v thymol. In skim and 2% reduced fat milk, Listeria monocytogenes Scott A was reduced from ∼5 log CFU/mL to below the detection limit in 6 h by 0.1% w/v and 0.45% w/v nanoemulsified thymol, respectively, contrasting with gradual reductions to 1.15 and 2.26 log CFU/mL after 48 h by same levels of free thymol. In full fat milk, L. monocytogenes was gradually reduced to be undetectable after 48 h by 0.6% w/v nanoemulsified thymol, contrasting with the insignificant reduction by free thymol. The improved antilisterial activities of nanoemulsified thymol resulted from the increased solubility in milk and synergistic activity with propylene glycol.
Spectroscopic investigation on sonodynamic and sonocatalytic damage of BSA molecules by Thymol Blue (TB) derivants under ultrasonic irradiation

NASA Astrophysics Data System (ADS)

Wang, Qi; Wu, Qiong; Wang, Jun; Chen, Dandan; Li, Ying; Gao, Jingqun; Wang, Baoxin

2014-07-01

In this paper, the Thymol Blue derivants including Thymol Blue (thymolsulfonphthalein), Thymol Blue-DA (3,3‧-Bis [N,N-bis (carboxymethyl) aminomethyl] thymolsulfonphthalein) and Thymol Blue-DA-Fe(III) (3,3‧-Bis [N,N-bis (carboxymethyl) aminomethyl] thymolsulfonphthalein-Ferrous(III)) were adopted as sonosensitizers to study the sonodynamic and sonocatalytic activities under ultrasonic irradiation. At first, the interaction of Thymol Blue derivants with bovine serum albumin (BSA) was studied by fluorescence spectroscopy. On that basis, the sonodynamic and sonocatalytic damages of Thymol Blue derivants to BSA under ultrasonic irradiation were investigated by the combination of UV-vis, circular dichroism (CD) and fluorescence spectroscopy. Meanwhile, some influenced factors (ultrasonic irradiation time, Thymol Blue derivants concentration and ionic strength) on the damaging degree of BSA molecules were also reviewed. In addition, synchronous fluorescence spectra were used to estimate the binding and damage sites of Thymol Blue derivants to BSA. Finally, the generation of ROS during sonodynamic and sonocatalytic processes was confirmed by the method of Oxidation-Extraction Spectrometry (OEP). Perhaps, this paper may offer some important subjects for the study of Thymol Blue derivants in sonodynamic therapy (SDT) and sonocatalytic therapy (SCT) technologies for tumor treatment and the effect of the amino acid and central metal.
The therapeutic effect of nano-encapsulated and nano-emulsion forms of carvacrol on experimental liver fibrosis.

PubMed

Hussein, Jihan; El-Banna, Mona; Mahmoud, Khaled F; Morsy, Safaa; Abdel Latif, Yasmin; Medhat, Dalia; Refaat, Eman; Farrag, Abdel Razik; El-Daly, Sherien M

2017-06-01

The present study aimed to compare the therapeutic efficiency of nano-encapsulated and nano-emulsion carvacrol administration on liver injury in thioacetamide (TAA) treated rats. To fulfill our target, we used sixty male albino rats classified into six groups as follow: control, nano-encapsulated carvacrol, nano-emulsion carvacrol, thioacetamide, treated nano-encapsulated carvacrol and treated nano-emulsion carvacrol groups. Blood samples were collected from all groups and the separated serum was used for analysis of the following biochemical parameters; aspartate aminotransferase (AST), alanine aminotransferase (ALT), S100 B protein, alpha fetoprotein (AFP) and caspase-3. The levels of malondialdehyde (MDA), reduced glutathione (GSH), nitric oxide (NO), monocyte chemoattractant protein-1(MCP-1) and hydroxyproline content were all evaluated in liver tissue homogenate. Histopathological examinations for liver tissues were also performed. Thioacetamide induced hepatic damage in rats as revealed by the significant increase in the levels of serum ALT, AST and produced oxidative stress as displayed by the significant elevation in the levels of hepatic MDA and NO concomitant with a significant decrease in GSH. In addition, thioacetamide significantly increased serum S100B protein, alpha fetoprotein and caspase-3 along with hepatic MCP-1 and hydroxyproline; these results were confirmed by the histopathological investigation. In contrast, nano-encapsulated and nano-emulsion carvacrol were able to ameliorate these negative changes in the thioacetamide injected rats. However, the effect of the nano-encapsulated form of carvacrol was more prominent than the nano-emulsion form. Nano-encapsulated and nano-emulsion carvacrol can ameliorate thioacetamide induced liver injury. These results could be attributed to the potential anti-inflammatory, antioxidant, and anti-apoptotic activities of carvacrol in addition to the effectiveness of the encapsulation technique that can protect carvacrol structure and increase its efficiency and stability. Moreover, nano-encapsulation of carvacrol is more efficient than nano-emulsion. Copyright © 2017 Elsevier Masson SAS. All rights reserved.
Carvacrol: from ancient flavoring to neuromodulatory agent.

PubMed

Zotti, Margherita; Colaianna, Marilena; Morgese, Maria Grazia; Tucci, Paolo; Schiavone, Stefania; Avato, Pinarosa; Trabace, Luigia

2013-05-24

Oregano and thyme essential oils are used for therapeutic, aromatic and gastronomic purposes due to their richness in active substances, like carvacrol; however, the effects of the latter on the central nervous system have been poorly investigated. The aim of our study was to define the effects of carvacrol on brain neurochemistry and behavioural outcome in rats. Biogenic amine content in the prefrontal cortex and hippocampus after chronic or acute oral carvacrol administration was measured. Animals were assessed by a forced swimming test. Carvacrol, administered for seven consecutive days (12.5 mg/kg p.o.), was able to increase dopamine and serotonin levels in the prefrontal cortex and hippocampus. When single doses were used (150 and 450 mg/kg p.o.), dopamine content was increased in the prefrontal cortex at both dose levels. On the contrary, a significant dopamine reduction in hippocampus of animals treated with 450 mg/kg of carvacrol was found. Acute carvacrol administration only significantly reduced serotonin content in either the prefrontal cortex or in the hippocampus at the highest dose. Moreover, acute carvacrol was ineffective in producing changes in the forced swimming test. Our data suggest that carvacrol is a brain-active molecule that clearly influences neuronal activity through modulation of neurotransmitters. If regularly ingested in low concentrations, it might determine feelings of well-being and could possibly have positive reinforcer effects.
Evaluation of the Impact of Varied Carvacrol Concentrations on Salmonella Recovery in Oregano and How Corn Oil Can Minimize the Effect of Carvacrol during Preenrichment.

PubMed

Beaubrun, Junia Jean-Gilles; Addy, Nicole; Keltner, Zachary; Farris, Samantha; Ewing, Laura; Gopinath, Gopal; Hanes, Darcy E

2018-06-01

Phenolic compounds, like carvacrol, in oregano interfere with the detection of foodborne pathogens such as Salmonella enterica. Carvacrol concentration varies based on plant cultivars and growth region. Six oregano cultivars were used to compare the impact of carvacrol concentration on Salmonella and to evaluate the effectiveness of corn oil to help increase Salmonella survival for detection. The results of Agilent 1200 series high-performance liquid chromatography analysis showed that carvacrol concentration in the six oregano cultivars ranged from 64 to 11,200 ppm. Oregano samples were artificially contaminated with S. enterica and were preenriched in Trypticase soy broth with or without 2% (v/v) corn oil. After 18 to 24 h at 37°C, aliquots were transferred to selective enrichment broths. Salmonella was recovered onto xylose lysine Tergitol 4 agar. Six Salmonella serovars were compared, and recovery varied based on carvacrol concentration and serovar. Samples with higher concentrations of carvacrol showed Salmonella recovery only when they were preenriched with corn oil. Based on metagenomic analysis, the microflora associated with the oregano also varied per cultivar. The results show that, as carvacrol levels increased, Salmonella survival decreased. However, the addition of corn oil to the preenrichment broth can minimize the antimicrobial effects of the phenolic compounds, thus allowing for increased detection of Salmonella from oregano cultivars.

Carvacrol Exerts Neuroprotective Effects Via Suppression of the Inflammatory Response in Middle Cerebral Artery Occlusion Rats.

PubMed

Li, Zhenlan; Hua, Cong; Pan, Xiaoqiang; Fu, Xijia; Wu, Wei

2016-08-01

Increasing evidence demonstrates that inflammation plays an important role in cerebral ischemia. Carvacrol, a monoterpenic phenol, is naturally occurring in various plants belonging to the family Lamiaceae and exerts protective effects in a mice model of focal cerebral ischemia/reperfusion injury by reducing infarct volume and decreasing the expression of cleaved caspase-3. However, the anti-inflammatory mechanisms by which carvacrol protect the brain have yet to be fully elucidated. We investigated the effects of carvacrol on inflammatory reaction and inflammatory mediators in middle cerebral artery occlusion rats. The results of the present study showed that carvacrol inhibited the levels of inflammatory cytokines and myeloperoxidase (MPO) activity, as well as the expression of iNOS and COX-2. It also increased SOD activity and decreased MDA level in ischemic cortical tissues. In addition, carvacrol treatment suppressed the ischemia/reperfusion-induced increase in the protein expression of nuclear NF-kB p65. In conclusion, we have shown that carvacrol inhibits the inflammatory response via inhibition of the NF-kB signaling pathway in a rat model of focal cerebral ischemia. Therefore, carvacrol may be a potential therapeutic agent for the treatment of cerebral ischemia injury.
Effect of a thymol application on olfactory memory and gene expression levels in the brain of the honeybee Apis mellifera.

PubMed

Bonnafé, Elsa; Drouard, Florian; Hotier, Lucie; Carayon, Jean-Luc; Marty, Pierre; Treilhou, Michel; Armengaud, Catherine

2015-06-01

Essential oils are used by beekeepers to control the Varroa mites that infest honeybee colonies. So, bees can be exposed to thymol formulations in the hive. The effects of the monoterpenoid thymol were explored on olfactory memory and gene expression in the brain of the honeybee. In bees previously exposed to thymol (10 or 100 ng/bee), the specificity of the response to the conditioned stimulus (CS) was lost 24 h after learning. Besides, the octopamine receptor OA1 gene Amoa1 showed a significant decrease of expression 3 h after exposure with 10 or 100 ng/bee of thymol. With the same doses, expression of Rdl gene, coding for a GABA receptor subunit, was not significantly modified but the trpl gene was upregulated 1 and 24 h after exposure to thymol. These data indicated that the genes coding for the cellular targets of thymol could be rapidly regulated after exposure to this molecule. Memory and sensory processes should be investigated in bees after chronic exposure in the hive to thymol-based preparations.
Anesthetic Agents of Plant Origin: A Review of Phytochemicals with Anesthetic Activity.

PubMed

Tsuchiya, Hironori

2017-08-18

The majority of currently used anesthetic agents are derived from or associated with natural products, especially plants, as evidenced by cocaine that was isolated from coca ( Erythroxylum coca , Erythroxylaceae) and became a prototype of modern local anesthetics and by thymol and eugenol contained in thyme ( Thymus vulgaris , Lamiaceae) and clove ( Syzygium aromaticum , Myrtaceae), respectively, both of which are structurally and mechanistically similar to intravenous phenolic anesthetics. This paper reviews different classes of phytochemicals with the anesthetic activity and their characteristic molecular structures that could be lead compounds for anesthetics and anesthesia-related drugs. Phytochemicals in research papers published between 1996 and 2016 were retrieved from the point of view of well-known modes of anesthetic action, that is, the mechanistic interactions with Na⁺ channels, γ-aminobutyric acid type A receptors, N -methyl-d-aspartate receptors and lipid membranes. The searched phytochemicals include terpenoids, alkaloids and flavonoids because they have been frequently reported to possess local anesthetic, general anesthetic, antinociceptive, analgesic or sedative property. Clinical applicability of phytochemicals to local and general anesthesia is discussed by referring to animal in vivo experiments and human pre-clinical trials. This review will give structural suggestions for novel anesthetic agents of plant origin.
Traps containing carvacrol, a biological approach for the control of Dermanyssus gallinae.

PubMed

Barimani, Alireza; Youssefi, Mohammad Reza; Tabari, Mohaddeseh Abouhosseini

2016-09-01

Resistance to conventional synthetic pesticides has been widely reported in Dermanyssus gallinae in different aviary systems. Cardboard traps containing acaricides had been introduced as a successive device for collection and control of the poultry red mite. The present study assessed field efficacy of traps containing carvacrol in the control and reduction of D. gallinae in laying poultry farm. Two different carvacrol-based formulations were tested for their toxicity and possible repellent activity on D. gallinae to determine the most appropriate formulation and concentration to be used in the field study. In vitro tests confirmed that 1 % carvacrol formulation with ethoxylated castor oil as emulsifier was significantly toxic to D. gallinae without any dissuading effect in comparison to ethanol and higher concentrations of carvacrol (p < 0.05). A subsequent in vivo experiment in a cage system laying farm demonstrated significant acaricidal activity for traps containing 1 % carvacrol. Throughout the study, untreated cardboard traps were used for monitoring mite populations. Carvacrol-impregnated traps were efficacious in the control of D. gallinae and led to over 92 % reduction in mite's population after 2 week of application. Toxic effects of carvacrol maintained through 2 weeks after the last application of traps. Results of the present study suggested that effective control of the poultry red mite can be achieved by traps containing carvacrol. These traps can be used safely in poultry facilities without any concern about residues in eggs, meat, and environment.
Bioactivity of essential oils in phytopathogenic and post-harvest fungi control.

PubMed

Santamarina, M P; Ibáñez, M D; Marqués, M; Roselló, J; Giménez, S; Blázquez, M A

2017-11-01

Commercial thyme and lavender essential oils were analysed by GC/MS. Sixty-six compounds accounting for 98.6-99.6% of total essential oil were identified. Thymol (52.14 ± 0.21%), followed by p-cymene (32.24 ± 0.16%), carvacrol (3.71 ± 0.01%) and γ-terpinene (3.34 ± 0.02%), were the main compounds in thyme essential oil, while large amounts of oxygenated monoterpenes linalool acetate (37.07 ± 0.24%) and linalool (30.16 ± 0.06%) were found in lavender one. In vitro antifungal activity of the essential oils was evaluated at 200 and 300 μg/mL against 10 phytopathogenic and post-harvest fungi, which significantly affect agriculture. Micelial growth inhibition was calculated for each tested fungus and dose. Thyme essential oil showed satisfactory results with 90-100% growth inhibition in almost all the assayed fungi at 300 μg/mL, while lavender essential oil showed no noteworthy inhibition data at either dose, and its growth was even enhanced. Thyme essential oil represents a natural alternative to control harvest and post-harvest fungi, and to extend the shelf-life of agriculture products.
Oregano Essential Oil as an Antimicrobial and Antioxidant Additive in Food Products.

PubMed

Rodriguez-Garcia, I; Silva-Espinoza, B A; Ortega-Ramirez, L A; Leyva, J M; Siddiqui, M W; Cruz-Valenzuela, M R; Gonzalez-Aguilar, G A; Ayala-Zavala, J F

2016-07-26

Food consumers and industries urged the need of natural alternatives to assure food safety and quality. As a response, the use of natural compounds from herbs and spices is an alternative to synthetic additives associated with toxic problems. This review discusses the antimicrobial and antioxidant activity of oregano essential oil (OEO) and its potential as a food additive. Oregano is a plant that has been used as a food seasoning since ancient times. The common name of oregano is given to several species: Origanum (family: Lamiaceae) and Lippia (family: Verbenaceae), amongst others. The main compounds identified in the different OEOs are carvacrol and thymol, which are responsible for the characteristic odor, antimicrobial, and antioxidant activity; however, their content may vary according to the species, harvesting season, and geographical sources. These substances as antibacterial agents make the cell membrane permeable due to its impregnation in the hydrophobic domains, this effect is higher against gram positive bacteria. In addition, the OEO has antioxidant properties effective in retarding the process of lipid peroxidation in fatty foods, and scavenging free radicals. In this perspective, the present review analyzes and discusses the state of the art about the actual and potential uses of OEO as an antimicrobial and antioxidant food additives.
Antimicrobial, Optical and Mechanical Properties of Chitosan-Starch Films with Natural Extracts.

PubMed

Lozano-Navarro, Jessica I; Díaz-Zavala, Nancy P; Velasco-Santos, Carlos; Martínez-Hernández, Ana L; Tijerina-Ramos, Beatriz I; García-Hernández, Margarita; Rivera-Armenta, José L; Páramo-García, Ulises; Reyes-de la Torre, Adriana I

2017-05-05

Natural extracts possess several kinds of antioxidants (anthocyanins, betalains, thymol, carvacrol, and resveratrol) that have also demonstrated antimicrobial properties. In order to study these properties, extracts from cranberry, blueberry, beetroot, pomegranate, oregano, pitaya, and resveratrol (from grapes) were obtained. Growth inhibition tests of mesophilic aerobes, coliforms, and fungi were conducted in films prepared from the extracts in accordance with Mexican Official Norms (NOM). Optical properties such as transparency and opacity, mechanical properties, and pH were also analyzed in these materials. The films with beetroot, cranberry, and blueberry extracts demonstrated the best antimicrobial activity against various bacteria and fungi in comparison with unmodified chitosan-starch film. This study shows that the addition of antioxidants improved the antimicrobial performance of these films. It was also found that antimicrobial properties are inherent to the films. These polymers combined with the extracts effectively inhibit or reduce microorganism growth from human and environmental contact; therefore, previous sterilization could be unnecessary in comparison with traditional plastics. The presence of extracts decreased transmittance percentages at 280 and 400 nm, as well as the transparency values, while increasing their opacity values, providing better UV-VIS light barrier properties. Despite diminished glass transition temperatures ( T g), the values obtained are still adequate for food packaging applications.
Antimicrobial, Optical and Mechanical Properties of Chitosan–Starch Films with Natural Extracts

PubMed Central

Lozano-Navarro, Jessica I.; Díaz-Zavala, Nancy P.; Velasco-Santos, Carlos; Martínez-Hernández, Ana L.; Tijerina-Ramos, Beatriz I.; García-Hernández, Margarita; Rivera-Armenta, José L.; Páramo-García, Ulises; Reyes-de la Torre, Adriana I.

2017-01-01

Natural extracts possess several kinds of antioxidants (anthocyanins, betalains, thymol, carvacrol, and resveratrol) that have also demonstrated antimicrobial properties. In order to study these properties, extracts from cranberry, blueberry, beetroot, pomegranate, oregano, pitaya, and resveratrol (from grapes) were obtained. Growth inhibition tests of mesophilic aerobes, coliforms, and fungi were conducted in films prepared from the extracts in accordance with Mexican Official Norms (NOM). Optical properties such as transparency and opacity, mechanical properties, and pH were also analyzed in these materials. The films with beetroot, cranberry, and blueberry extracts demonstrated the best antimicrobial activity against various bacteria and fungi in comparison with unmodified chitosan–starch film. This study shows that the addition of antioxidants improved the antimicrobial performance of these films. It was also found that antimicrobial properties are inherent to the films. These polymers combined with the extracts effectively inhibit or reduce microorganism growth from human and environmental contact; therefore, previous sterilization could be unnecessary in comparison with traditional plastics. The presence of extracts decreased transmittance percentages at 280 and 400 nm, as well as the transparency values, while increasing their opacity values, providing better UV–VIS light barrier properties. Despite diminished glass transition temperatures (Tg), the values obtained are still adequate for food packaging applications. PMID:28475151
Antimicrobial activity of five essential oils against origin strains of the Enterobacteriaceae family.

PubMed

Peñalver, Pedro; Huerta, Belén; Borge, Carmen; Astorga, Rafael; Romero, Rafael; Perea, Anselmo

2005-01-01

An in vitro assay measuring the antimicrobial activity of essential oils of Coridothymus capitatus (Spanish origanum), Satureja montana, Thymus mastichina (Spanish Origanum majorana), Thymus zygis (Spanish variety of Thymus vulgaris) and Origanum vulgare has been carried out against poultry origin strains of Escherichia coli, Salmonella enteritidis and Salmonella essen, and pig origin strains of enterotoxigenic E. coli (ETEC), Salmonella choleraesuis and Salmonella typhimurium. Using the broth microdilution method, all the essential oils showed an MIC > or = 2% (v/v) for the two strains of E. coli. The essential oil that showed the highest antimicrobial activity against the four strains of Salmonella was Origanum vulgare (MIC < or = 1% v/v), followed by Thymus zygis (MIC < or =2% v/v). Thymus mastichina inhibited all the microorganisms at the highest concentration, 4% (v/v), while the rest of the essential oils showed highly variable results. By chemotyping, higher inhibitory capacity was observed in the oils with a higher percentage of phenolic components (carvacrol and thymol) in comparison with oils containing the monoterpenic alcohol linalool. The results of this work confirm the antimicrobial activity of some essential oils, as well as their potential application in the treatment and prevention of poultry and pig diseases caused by salmonella.
Report on the Medicinal Use of Eleven Lamiaceae Species in Lebanon and Rationalization of Their Antimicrobial Potential by Examination of the Chemical Composition and Antimicrobial Activity of Their Essential Oils

PubMed Central

Khoury, Madona; Eparvier, Véronique; Ouaini, Naïm

2016-01-01

Many Lamiaceae species are consumed in the Lebanese cuisine as food or condiment and are largely used in the traditional medicine of Lebanon to treat various diseases, including microbial infections. In this article we report the traditional medicinal uses of eleven Lamiaceae species: Coridothymus capitatus L., Lavandula stoechas L., Lavandula angustifolia Mill., Mentha spicata L. subsp. condensata, Origanum syriacum L., Rosmarinus officinalis, Salvia fruticosa Miller., Satureja cuneifolia Ten., Satureja thymbra L., Thymbra spicata L., and Vitex agnus-castus L. and study the chemical composition and antimicrobial activity of their essential oils (EOs). Our survey showed that Lamiaceae species are mainly used against gastrointestinal disorders and microbial infections. Chemical analysis of the EOs obtained from these plants allowed us to identify seventy-five compounds describing more than 90% of the relative composition of each EO. Essential oils with high amounts of thymol and carvacrol possessed the strongest antimicrobial activity. As expected, these two compounds demonstrated an interesting antifungal efficacy against the filamentous fungus T. rubrum. Our results confirmed that some of the Lamiaceae species used in Lebanon ethnopharmacological practices as antimicrobial agents do possess antibacterial and antifungal potential consistent with their use in alternative or complementary medicine. PMID:28053641
Antimicrobial properties of nisin after glycation with lactose, maltodextrin and dextran and the thyme oil emulsions prepared thereof.

PubMed

Chen, Huaiqiong; Davidson, P Michael; Zhong, Qixin

2014-11-17

To clarify the reported conflicting antimicrobial activities of nisin after glycation, nisin was glycated with lactose, maltodextrin, and dextran at 70 °C and 50% relative humidity for 1-24 h. Nisin before and after glycation was studied for the first time to prepare thyme oil emulsions. The activity of glycated nisin and the thyme oil emulsions was tested in both tryptic soy broth (TSB) and 2% reduced fat milk. Results showed that nisin glycated with a smaller saccharide for a longer duration had a higher degree of glycation and the reduced number of positive charges lowered its antibacterial activity. The emulsified thyme oil had an additive effect with either glycated or native nisin against Listeria monocytogenes Scott A and Bacillus subtilis in TSB and 2% reduced fat milk. However, emulsions were less effective against L. monocytogenes Scott A in milk than same units of native nisin and same concentration of free thyme oil, likely due to the reduced availability of thymol and carvacrol, the main components of thyme oil. These results showed that glycation of nisin cannot broaden its antimicrobial activity and nisin is not a good compound to prepare emulsions of essential oils. Copyright © 2014 Elsevier B.V. All rights reserved.
Application of Gelidium corneum edible films containing carvacrol for ham packages.

PubMed

Lim, G O; Hong, Y H; Song, K B

2010-01-01

We prepared an edible film of Gelidium corneum (GC) containing carvacrol as an antimicrobial and antioxidative agent. The GC film containing carvacrol significantly decreased the WVP, while TS and %E values were increased, compared to the film without carvacrol. Increasing amounts of an antimicrobial agent increased antimicrobial activity against Escherichia coli O157:H7 and Listeria monocytogenes. Application of the film to ham packaging successfully inhibited the microbial growth and lipid oxidation of ham during storage. Our results indicate that GC film can be a useful edible packaging material for food products, and the incorporation of carvacrol in the GC film may extend the shelf life.
Effect of chitosan-carvacrol coating on the quality of Pacific white shrimp during iced storage as affected by caprylic acid.

PubMed

Wang, Qianyun; Lei, Jun; Ma, Junjie; Yuan, Gaofeng; Sun, Haiyan

2018-01-01

This study aimed to investigate the effect of chitosan-carvacrol coating with or without caprylic acid (CAP) on the quality of Pacific white shrimp (Litopenaeus vannamei) during 10days of iced storage. The result showed that chitosan-carvacrol coating significantly inhibited the increase in total aerobic plate count (TPC), pH and total volatile basic nitrogen content (TVB-N) of shrimp in comparison with the control. Chitosan-carvacrol coating also delayed the melanosis formation and changes of ΔE values, and improved the texture and sensory properties of shrimp. Moreover, incorporation of CAP potentiated the efficacy of chitosan-carvacrol coating in retarding the increase of TPC and TVB-N. Incorporation of CAP into chitosan-carvacrol coating also enabled the texture characteristics of shrimp to be retained greater degrees. These results suggested that chitosan-carvacrol coating may be promising to be used as active packaging for extending the shelf life, and incorporation of CAP may enhance the efficacy of the coating. Copyright © 2017 Elsevier B.V. All rights reserved.
Thymol derivatives from hairy roots of Arnica montana.

PubMed

Weremczuk-Jezyna, I; Kisiel, W; Wysokińska, H

2006-09-01

Five known thymol derivatives were isolated from roots of Arnica montana transformed with Agrobacterium rhizogenes LBA 9402. The compounds were characterized by spectral methods. The pattern of thymol derivatives in light-grown hairy roots was slightly different from that in dark-grown ones. This is the first report on the presence of thymol derivatives in hairy roots of the plant.
Thymol nanoencapsulated by sodium caseinate: physical and antilisterial properties.

PubMed

Pan, Kang; Chen, Huaiqiong; Davidson, P Michael; Zhong, Qixin

2014-02-19

In this work, thymol was encapsulated in sodium caseinate using high shear homogenization. The transparent dispersion at neutral pH was stable for 30 days at room temperature as determined by dynamic light scattering and atomic force microscopy, which agreed with high ζ potential of nanoparticles. The slightly decreased particle dimension during storage indicates the absence of Ostwald ripening. When molecular binding was studied by fluorescence spectroscopy, thymol was observed to bind with tyrosine and possibly other amino acid residues away from tryptophan of caseins. At pH 4.6 (isoelectric point of caseins), the stabilization of thymol nanoparticles against aggregation was enabled by soluble soybean polysaccharide, resulting from the combined electrostatic and steric repulsions. The encapsulated thymol showed the significantly improved antilisterial activity in milk with different fat levels when compared to thymol crystals, resulting from the quicker mixing and increased solubility in the milk serum. The transparent thymol nanodispersions have promising applications to improve microbiological safety and quality of foods.
Synthesis and Proapoptotic Activity on Cervical Cancer Cell of Ester Eugenol 1-(3-Methoxy-4-hydroxy)phenyl-2-propylmethanoate

NASA Astrophysics Data System (ADS)

Farid Rahman, Moh.; Nazhif Haykal, Muhammad; Andriani Siagian, Novi; Maiselina Sriepindonnta, Priscilla; Tampubolon, Norman Alexander

2018-01-01

Proapoptotic activity of ester eugenol,1-(3-methoxy-4-hydroxy)phenyl-2-propylmethanoat, which synthesized from eugenol is reported. Eugenol as starting material in the synthesis of ester eugenol was obtained from fractional distillation of clove oil with the yield of 70.66%. Synthesis of ester eugenol was camed out by addition-esterification reaction through reaction between eugenol and formic acid with mol ratio of 1:27 and reaction time for11 h. GC-MS analysis showed ester eugenol was afforded purity of 92.42% and the yield in of 93.34%. UV spectra of ester eugenol was observed the formation of carbonyl group at λmax 290 nm and supported by FT-IR analysis at 1714.60 cm-1 (carbonyl group), 1193.65 cm-1 (C-O-C ester group) and the absence of vynil group in eugenol structure at region 914.20 and 995.20 cm-1. Mass spectra showed ion molecule at m/z 210 was accordance with molecular weight of ester eugenol. Afterward, HeLa cell culture media was prepared for cervical cancer antiproliferative test. The result which showed in histogram indicated that LC50 of ester eugenol was reached at concentration below 0.01% while eugenol was up to 0.01% that observed cervical cancer cell apoptotic activity. LC50 value of ester eugenol was obtained at concentration 48.73 ppm. This research reported that natural product modified its structure has potency to cure cervical cancer.
The combined efficacy of carvacrol and modified atmosphere packaging on the survival of Salmonella, Campylobacter jejuni and lactic acid bacteria on turkey breast cutlets.

PubMed

Nair, Divek V T; Kiess, Aaron; Nannapaneni, Rama; Schilling, Wes; Sharma, Chander Shekhar

2015-08-01

The primary objective of this study was to determine the efficacy of carvacrol in combination with modified atmosphere packaging (MAP) in reducing Salmonella on turkey breast cutlets stored at 4 °C. In experiment I, carvacrol (0.5, 1, and 2% v/v) was applied as surface treatment and samples were stored under aerobic condition or as surface and dip treatments followed by storage in an environment of 100% carbon dioxide. The findings of the experiment I revealed the synergistic activity of carvacrol with carbon dioxide in reducing Salmonella when used as dip treatment compared to the surface treatment. In experiment II, turkey breast cutlets were dip treated with carvacrol (0.25, 0.5, and 1% v/v) for 30 s and stored under MAP (95% carbon dioxide and 5% oxygen) to evaluate the efficacy against Salmonella, Campylobacter jejuni and lactic acid bacteria on turkey breast cutlets. In experiment II, the combined application of carvacrol and MAP resulted in 1.0-2.0 log CFU/g reduction (P ≤ 0.05) of both Salmonella and Campylobacter on turkey breast cutlets for 7 d storage at 4 °C. MAP alone and in combination with carvacrol reduced lactic acid bacteria (P ≤ 0.05) on cutlets stored at 4 °C for 21 d period. There was no difference (P ≤ 0.05) in meat color among treatments and controls except for an increased paleness of meat (P ≤ 0.05) observed for the 1% carvacrol treated cutlets stored under MAP after 21 d of storage. The high concentration of carbon dioxide and carvacrol treatments did not cause any alteration in meat pH (P ≤ 0.05). In conclusion, carvacrol was effective at a low concentration of 0.25% (v/v) in reducing Salmonella and C. jejuni by ∼1.0 log CFU/g when stored under MAP. Copyright © 2015 Elsevier Ltd. All rights reserved.
Application of edible coating with starch and carvacrol in minimally processed pumpkin.

PubMed

Santos, Adriele R; da Silva, Alex F; Amaral, Viviane C S; Ribeiro, Alessandra B; de Abreu Filho, Benicio A; Mikcha, Jane M G

2016-04-01

The present study evaluated the effect of an edible coating of cassava starch and carvacrol in minimally processed pumpkin (MPP). The minimal inhibitory concentration (MIC) of carvacrol against Escherichia coli, Salmonella enterica serotype Typhimurium, Aeromonas hydrophila, and Staphylococcus aureus was determined. The edible coating that contained carvacrol at the MIC and 2 × MIC was applied to MPP, and effects were evaluated with regard to the survival of experimentally inoculated bacteria and autochthonous microflora in MPP. Total titratable acidity, pH, weight loss, and soluble solids over 7 days of storage under refrigeration was also analyzed. MIC of carvacrol was 312 μg/ml. Carvacrol at the MIC reduced the counts of E. coli and S. Typhimurium by approximately 5 log CFU/g. A. hydrophila was reduced by approximately 8 log CFU/g, and S. aureus was reduced by approximately 2 log CFU/g on the seventh day of storage. Carvacrol at the 2 × MIC completely inhibited all isolates on the first day of Storage. coliforms at 35 °C and 45 °C were not detected (< 3 MPN/g) with either treatment on all days of shelf life. The treatment groups exhibited a reduction of approximately 2 log CFU/g in psychrotrophic counts compared with controls on the last day of storage. Yeast and mold were not detected with either treatment over the same period. The addition of carvacrol did not affect total titratable acidity, pH, or soluble solids and improved weight loss. The edible coating of cassava starch with carvacrol may be an interesting approach to improve the safety and microbiological quality of MPP.
The effect of eugenol on the cariogenic properties of Streptococcus mutans and dental caries development in rats

PubMed Central

XU, JING-SHU; LI, YAO; CAO, XUE; CUI, YUN

2013-01-01

Eugenol has been widely used in medicine due to its antibacterial, anti-inflammatory, antioxidant, anticancer and analgesic properties. The present study was designed to investigate the effects of eugenol on the cariogenic properties of Streptococcus mutans and dental caries development in rats. Eugenol demonstrated significant inhibitory effects against acid production by S. mutans. The synthesis of water-insoluble glucans by glucosyltransferases was reduced by eugenol. Eugenol also markedly suppressed the adherence of S. mutans to saliva-coated hydroxyapatite beads. Furthermore, topical application of eugenol reduced the incidence and severity of carious lesions in rats. These results suggest that the natural compound eugenol may be a useful therapeutic agent for dental caries. PMID:23837051
Acid-Catalyzed Isomerization of Carvone to Carvacrol

ERIC Educational Resources Information Center

Kjonaas, Richard A.; Mattingly, Shawn P.

2005-01-01

The acid-catalyzed isomerization of carvone to carvacrol, first reported by Ritter and Ginsburg, is especially well suited with a permanent-magnet FT instrument. The acid-catalyzed isomerization of carvone to carvacrol produced a 61% yield after a three hour reflux with 30% aqueous sulfuric acid.

Characteristics of eugenol loaded chitosan-tripolyphosphate particles as affected by initial content of eugenol and their in-vitro release characteristic

NASA Astrophysics Data System (ADS)

Cahyono, B.; A’yun, Qurrotu; Suzery, M.; Hadiyanto

2018-04-01

The aim of this research was to determine encapsulation efficiency, loading capacity and controlled release of eugenol loaded chitosan-tpp products which prepared by coaservation method. The characteristic of eugenol-loaded chitosan showed that %EE and % LC increased by increasing the initial eugenol content. The optimum of %EE (72.63%) and %LC (43.96%) were obtained at the ratio of chitosan to eugenol of 1:1.5. The FTIR spectrum showed the characteristic peaks of eugenol appearing on spectrum of eugenol encapsulated and blue-shift in the hydroxyl band from 3425.58 cm-1 in chitosan-tpp to 3417.86 cm-1 and 3394.72 cm-1 in eugenol loaded chitosan-tpp indicating that eugenol was successfully encapsulated. The surface morphologies of freeze-dried particles with the optimum %EE showed that more surface roughness and porosity than plain particles. Furthermore, the in vitro release of particles with minimum and optimum %EE were also investigated in acid (Simulated Gastric Fluid) and base (Simulated Intestinal Fluid) medium at ambient temperature.
Eugenol prevents amyloid formation of proteins and inhibits amyloid-induced hemolysis

NASA Astrophysics Data System (ADS)

Dubey, Kriti; Anand, Bibin G.; Shekhawat, Dolat Singh; Kar, Karunakar

2017-02-01

Eugenol has attracted considerable attention because of its potential for many pharmaceutical applications including anti-inflammatory, anti-tumorigenic and anti-oxidant properties. Here, we have investigated the effect of eugenol on amyloid formation of selected globular proteins. We find that both spontaneous and seed-induced aggregation processes of insulin and serum albumin (BSA) are significantly suppressed in the presence of eugenol. Isothermal titration calorimetric data predict a single binding site for eugenol-insulin complex confirming the affinity of eugenol for native soluble insulin species. We also find that eugenol suppresses amyloid-induced hemolysis. Our findings reveal the inherent ability of eugenol to stabilize native proteins and to delay the conversion of protein species of native conformation into β-sheet assembled mature fibrils, which seems to be crucial for its inhibitory effect.
Enzymatic synthesis of eugenol benzoate by immobilized Staphylococcus aureus lipase: optimization using response surface methodology and determination of antioxidant activity.

PubMed

Horchani, Habib; Ben Salem, Nadia; Zarai, Zied; Sayari, Adel; Gargouri, Youssef; Chaâbouni, Moncef

2010-04-01

The ability of a non-commercial immobilized Staphylococcus aureus lipase to catalyze the esterification of eugenol with benzoic acid was checked and the antioxidant power of the ester formed was evaluated. Response surface methodology based on four variables (the reaction temperature, the amount of lipase, the benzoic acid/eugenol molar ratio and the volume of solvent) was used to optimize the experimental conditions of eugenol benzoate synthesis. The maximum conversion yield (75%) was obtained using 240 IU of immobilized lipase, a benzoic acid/eugenol molar ratio of 1.22 dissolved in 4.6 ml chloroform at 41 degrees Celsius. The antioxidant activities of eugenol and its ester were evaluated. Compared to BHT, used as a model synthetic antioxidant, the eugenol benzoate showed a higher antioxidative activity. The IC(50) value for 1,1-diphenyl-2-picrylhydrazyl was found to be 18.2 microg/ml versus 20.2 microg/ml for eugenol and eugenol benzoate. Copyright 2009 Elsevier Ltd. All rights reserved.
Interaction of carvacrol with the Ascaris suum nicotinic acetylcholine receptors and gamma-aminobutyric acid receptors, potential mechanism of antinematodal action

PubMed Central

Marjanović, Djordje S.; Trailović, Jelena Nedeljković; Robertson, Alan P.; Martin, Richard J.

2015-01-01

Essential plant oils (or their active principles) are safe to use and a potentially attractive alternative to current antiparasitic drugs. In the present study, we tested the effects of carvacrol on the isolated tissues of Ascaris suum and investigated potential interactions with other antiparasitic drugs. We used somatic muscle flaps for contraction assays, as well as for electrophysiological investigations. Carvacrol 300 μM highly significantly inhibited contractions caused by 1, 3, 10, 30, and 100 μM of ACh (p=0.0023, p=0.0002, p=0.0002, p<0.0001, and p<0.0001). The control EC50 for acetylcholine was 8.87 μM (log EC50=0.95±0.26), while Rmax was 2.53±0.24 g. The EC50 of acetylcholine in the presence of 300 μM of carvacrol was 27.71 μM (log EC50=1.44±0.28) and the Rmax decreased to 1.63±0.32 g. Furthermore, carvacrol highly significant potentiates inhibitory effect of GABA and piperazine on the contractions induced by ACh. However, carvacrol (100 and 300 μM), did not produce any changes in the membrane potential or conductance of the A. suum muscle cell. While, 300 μM of carvacrol showed a significant inhibitory effect on ACh-induced depolarization response. The mean control depolarization was 13.58±0.66 mV and decreased in presence of carvacrol to 4.50±1.02 mV (p<0.0001). Mean control Δg was 0.168±0.017 μS, while in the presence of 300 μM of carvacrol, Δg significantly decreased to 0.060±0.018 ΔS (p=0.0017). The inhibitory effect on contractions may be the explanation of the antinematodal potential of carvacrol. Moreover, inhibition of depolarizations caused by ACh and reduction of conductance changes directly points to an interaction with the nAChR in A. suum. PMID:25944741
Determination of the thermal and physical properties of black tattoo ink using compound analysis.

PubMed

Humphries, Alexander; Lister, Tom S; Wright, Philip A; Hughes, Michael P

2013-07-01

Despite the widespread use of laser therapy in the removal of tattoos, comparatively little is known about its mechanism of action. There is a need for an improved understanding of the composition and thermal properties of the tattoo ink in order that simulations of laser therapy may be better informed and treatment parameters optimised. Scanning electron microscopy and time-of-flight secondary ion mass spectrometry identified that the relative proportions of the constituent compounds of the ink likely to exist in vivo are the following: carbon black pigment (89 %), carvacrol (5 %), eugenol (2 %), hexenol (3 %) and propylene glycol (1 %). Chemical compound property tables identify that changes in phase of these compounds lead to a considerable reduction in the density and thermal conductivity of the ink and an increase in its specific heat as temperature increases. These temperature-dependent values of density, thermal conductivity and specific heat are substantially different to the constant values, derived from water or graphite at a fixed temperature, which have been applied in the simulations of laser therapy as previously described in the literature. Accordingly, the thermal properties of black tattoo ink described in this study provide valuable information that may be used to improve simulations of tattoo laser therapy.
Possible Synergistic Effects of Thymol and Nicotine Against Crithidia bombi Parasitism in Bumble Bees.

PubMed

Biller, Olivia Masi; Adler, Lynn S; Irwin, Rebecca E; McAllister, Caitlin; Palmer-Young, Evan C

2015-01-01

Floral nectar contains secondary compounds with antimicrobial properties that can affect not only plant-pollinator interactions, but also interactions between pollinators and their parasites. Although recent work has shown that consumption of plant secondary compounds can reduce pollinator parasite loads, little is known about the effects of dosage or compound combinations. We used the generalist pollinator Bombus impatiens and its obligate gut parasite Crithidia bombi to study the effects of nectar chemistry on host-parasite interactions. In two experiments we tested (1) whether the secondary compounds thymol and nicotine act synergistically to reduce parasitism, and (2) whether dietary thymol concentration affects parasite resistance. In both experiments, uninfected Bombus impatiens were inoculated with Crithidia and then fed particular diet treatments for 7 days, after which infection levels were assessed. In the synergism experiment, thymol and nicotine alone and in combination did not significantly affect parasite load or host mortality. However, the thymol-nicotine combination treatment reduced log-transformed parasite counts by 30% relative to the control group (P = 0.08). For the experiment in which we manipulated thymol concentration, we found no significant effect of any thymol concentration on Crithidia load, but moderate (2 ppm) thymol concentrations incurred a near-significant increase in mortality (P = 0.054). Our results tentatively suggest the value of a mixed diet for host immunity, yet contrast with research on the antimicrobial activity of dietary thymol and nicotine in vertebrate and other invertebrate systems. We suggest that future research evaluate genetic variation in Crithidia virulence, multi-strain competition, and Crithidia interactions with the gut microbe community that may mediate antimicrobial activities of secondary compounds.
Possible Synergistic Effects of Thymol and Nicotine against Crithidia bombi Parasitism in Bumble Bees

PubMed Central

Adler, Lynn S.; Irwin, Rebecca E.; McAllister, Caitlin

2015-01-01

Floral nectar contains secondary compounds with antimicrobial properties that can affect not only plant-pollinator interactions, but also interactions between pollinators and their parasites. Although recent work has shown that consumption of plant secondary compounds can reduce pollinator parasite loads, little is known about the effects of dosage or compound combinations. We used the generalist pollinator Bombus impatiens and its obligate gut parasite Crithidia bombi to study the effects of nectar chemistry on host-parasite interactions. In two experiments we tested (1) whether the secondary compounds thymol and nicotine act synergistically to reduce parasitism, and (2) whether dietary thymol concentration affects parasite resistance. In both experiments, uninfected Bombus impatiens were inoculated with Crithidia and then fed particular diet treatments for 7 days, after which infection levels were assessed. In the synergism experiment, thymol and nicotine alone and in combination did not significantly affect parasite load or host mortality. However, the thymol-nicotine combination treatment reduced log-transformed parasite counts by 30% relative to the control group (P = 0.08). For the experiment in which we manipulated thymol concentration, we found no significant effect of any thymol concentration on Crithidia load, but moderate (2 ppm) thymol concentrations incurred a near-significant increase in mortality (P = 0.054). Our results tentatively suggest the value of a mixed diet for host immunity, yet contrast with research on the antimicrobial activity of dietary thymol and nicotine in vertebrate and other invertebrate systems. We suggest that future research evaluate genetic variation in Crithidia virulence, multi-strain competition, and Crithidia interactions with the gut microbe community that may mediate antimicrobial activities of secondary compounds. PMID:26657643
Nanocapsular Dispersion of Thymol for Enhanced Dispersibility and Increased Antimicrobial Effectiveness against Escherichia coli O157:H7 and Listeria monocytogenes in Model Food Systems

PubMed Central

Shah, Bhavini; Davidson, P. Michael

2012-01-01

Essential oils are marginally soluble in water, making it challenging to evenly disperse them in foods and resulting in an increased tendency to bind with food lipids and proteins, resulting in lowered antimicrobial efficacy. In the current study, free and nano-dispersed (ND) thymol were compared in terms of their antimicrobial efficacies against Escherichia coli O157:H7 ATCC 43889 and 43894 and Listeria monocytogenes strains Scott A and 101 in apple cider and 2% reduced-fat milk. Apple cider was adjusted to pHs 5.5 and 3.5, and antimicrobial tests were performed at 0.3-, 0.5-, 0.75-, and 1.0-g/liter thymol concentrations at 35, 32, 25, and 4°C. Overall, 0.5 and 1.0 g/liter thymol in nano-dispersion and along with free thymol were inhibitory and bactericidal, respectively, against bacterial strains under all treatment conditions. At pH 5.5, 0.5 g/liter ND thymol was bacteriostatic against L. monocytogenes and E. coli for up to 48 h. At pH 3.5, L. monocytogenes controls did not survive beyond 12 h but E. coli survived and was inhibited by 0.5 g/liter ND thymol after 12 and 48 h in apple cider. E. coli strains were significantly sensitive to 4°C and pH 3.5 (P < 0.05). When bacteria were tested in 2% reduced-fat milk at 35 or 32°C, ND and free thymol demonstrated inhibition at 4.5 g/liter. Thus, the current technology seems to be promising and novel, enabling thymol-containing nano-dispersions that are not only transparent but also effective against pathogens in food applications, especially in clear beverages. PMID:23023745
Innovation of natural essential oil-loaded Orabase for local treatment of oral candidiasis

PubMed Central

Labib, Gihan S; Aldawsari, Hibah

2015-01-01

Purpose Oral candidiasis may be manifested in the oral cavity as either mild or severe oral fungal infection. This infection results from the overgrowth of Candida species normally existing in the oral cavity in minute amounts based on many predisposing factors. Several aspects have spurred the search for new strategies in the treatment of oral candidiasis, among which are the limited numbers of new antifungal drugs developed in recent years. Previous studies have shown that thyme and clove oils have antimycotic activities and have suggested their incorporation into pharmaceutical preparations. This study aimed to investigate the possibility of the incorporation and characterization of essential oils or their extracted active ingredients in Orabase formulations. Methods Orabase loaded with clove oil, thyme oil, eugenol, and thymol were prepared and evaluated for their antifungal activities, pH, viscosity, erosion and water uptake characteristics, mechanical properties, in vitro release behavior, and ex vivo mucoadhesion properties. Results All prepared bases showed considerable antifungal activity and acceptable physical characteristics. The release pattern from loaded bases was considerably slow for all oils and active ingredients. All bases showed appreciable adhesion in the in vitro and ex vivo studies. Conclusion The incorporation of essential oils in Orabase could help in future drug delivery design, with promising outcomes on patients’ well-being. PMID:26170621
Innovation of natural essential oil-loaded Orabase for local treatment of oral candidiasis.

PubMed

Labib, Gihan S; Aldawsari, Hibah

2015-01-01

Oral candidiasis may be manifested in the oral cavity as either mild or severe oral fungal infection. This infection results from the overgrowth of Candida species normally existing in the oral cavity in minute amounts based on many predisposing factors. Several aspects have spurred the search for new strategies in the treatment of oral candidiasis, among which are the limited numbers of new antifungal drugs developed in recent years. Previous studies have shown that thyme and clove oils have antimycotic activities and have suggested their incorporation into pharmaceutical preparations. This study aimed to investigate the possibility of the incorporation and characterization of essential oils or their extracted active ingredients in Orabase formulations. Orabase loaded with clove oil, thyme oil, eugenol, and thymol were prepared and evaluated for their antifungal activities, pH, viscosity, erosion and water uptake characteristics, mechanical properties, in vitro release behavior, and ex vivo mucoadhesion properties. All prepared bases showed considerable antifungal activity and acceptable physical characteristics. The release pattern from loaded bases was considerably slow for all oils and active ingredients. All bases showed appreciable adhesion in the in vitro and ex vivo studies. The incorporation of essential oils in Orabase could help in future drug delivery design, with promising outcomes on patients' well-being.
Metabolism of thymol and trans-anethole in larvae of Spodoptera litura and Trichoplusia ni (Lepidoptera: Noctuidae).

PubMed

Passreiter, Claus M; Wilson, Joanne; Andersen, Raymond; Isman, Murray B

2004-05-05

Metabolism of the monoterpenoid thymol and the phenylpropanoid trans-anethole, both constituents of essential oils, was investigated following topical and oral administration of the compounds to the tobacco cutworm (Spodoptera litura) and the cabbage looper (Trichoplusia ni). In both species and irrespective of route, administration of thymol resulted in the excretion of its 3-O-beta-glucoside, whereas trans-anethole was hydroxylated on the side chain methyl group. Both metabolites were isolated and their structures elucidated by interpretation of their mass and NMR spectra. Previous experiments indicated that trans-anethole synergized the toxicity of thymol in S. litura, but analyses of feces indicated that metabolism of thymol was not significantly suppressed when the two compounds were orally coadministered to T. ni larvae.
Lavender-thymol as a new topical aromatherapy preparation for episiotomy: A randomised clinical trial.

PubMed

Marzouk, T; Barakat, R; Ragab, A; Badria, F; Badawy, A

2015-01-01

The objective of this study was to evaluate the effectiveness of topical lavender-thymol in promoting episiotomy healing. This placebo-controlled, single-blinded, randomised clinical trial involved 60 primiparous women. REEDA score was used to evaluate the outcome of the trial. On the 7th post-partum day, women in Placebo-treated group had worse Redness, Edema, Ecchymosis, Discharge and Approximation (REEDA) score of 3.93 ± 3.65 compared with those in Lavender-thymol-treated group (2.03 ± 1.7) with significant difference (P = 0.013). Visual analogue Scale (VAS) score for pain at episiotomy in Lavender-thymol-treated group was 3.5 ± 1.9, whereas in Placebo-treated group it was 2.1 ± 2.2 (p = 0.011) for dyschezia, 3.8 ± 1.7 and 2.8 ± 1.6 in Placebo- and Lavender-thymol-treated women, respectively (p = 0.023). At 7th post-partum week, dyspareunia was more severe in Placebo-treated group compared with that in Lavender-thymol-treated group (5.3 ± 2.7 vs 2.7 ± 1.5 and p < 0.001). Topical aromatherapy using lavender-thymol was highly effective, suitable and safe for episiotomy wound care with little or no expected side effects compared with that using placebo.
Oregano (Lippia graveolens) essential oil added within pectin edible coatings prevents fungal decay and increases the antioxidant capacity of treated tomatoes.

PubMed

Rodriguez-Garcia, Isela; Cruz-Valenzuela, M Reynaldo; Silva-Espinoza, Brenda A; Gonzalez-Aguilar, Gustavo A; Moctezuma, Edgar; Gutierrez-Pacheco, M Melissa; Tapia-Rodriguez, Melvin R; Ortega-Ramirez, Luis A; Ayala-Zavala, J Fernando

2016-08-01

Tomato is a fruit widely consumed due to its flavor and nutritional value; however, it is susceptible to fungi contamination. Oregano essential oil (OEO) is a fungicide whose constituents are volatile; therefore, their incorporation within edible coatings can protect them and maintain their efficacy. In this context, this study evaluated the effect of OEO applied within pectin coatings on the inhibition of Alternaria alternata growth, antioxidant content and sensorial acceptability of tomatoes. The major volatile compounds of OEO were carvacrol (47.41%), p-cymene (26.44%) and thymol (3.02%). All the applied OEO concentrations (15.7, 25.9 and 36.1 g L(-1) ) inhibited the in vitro growth of A. alternata, whereas the in vivo effective concentrations were 25.9 and 36.1 g L(-1) . Additionally, there was an increment of total phenols and antioxidant activity in coated tomatoes compared to controls. Aroma acceptability of tomatoes was not affected by the pectin-OEO coating; additionally, the pectin, pectin-OEO 15.7 g L(-1) treatments and control tomatoes showed higher flavor acceptability than those coated with pectin-OEO 25.9 and 36.1 g L(-1) . Pectin-OEO coatings showed antifungal effect and increased the antioxidant activity without negative effects on the sensorial acceptability of tomatoes. © 2015 Society of Chemical Industry. © 2015 Society of Chemical Industry.
Chemical compositions, antioxidant and antimicrobial properties of Ziziphora clinopodioides Lam. essential oils collected from different parts of Iran.

PubMed

Shahbazi, Yasser

2017-10-01

The aims of the present study were to investigate chemical compositions, antioxidant and antimicrobial properties of Ziziphora clinopodioides essential oils (ZEOs) collected from four provinces in western Iran (Ilam, Lorestan, Kermanshah and Kurdestan). Carvacrol was the most abundant constituent in the flower, stem and leaf oil samples of Ilam, Lorestan and Kermanshah regions by 73.12-74.29%, 66.47-66.89% and 65.11-65.32%, respectively. The most abundant components in Kurdestan sample were thymol (55.32-55.60%), followed by γ -terpinene (24.45-24.56%), p -cymene (10.21-10.25%) and α -terpinene (2.75-2.77%). The ZEO inhibited the growth of Listeria monocytogenes , Salmonella typhimurium , Escherichia coli O157:H7, Bacillus subtilis , Bacillus cereus and Staphylococcus aureus at MIC values between 0.03 and 0.04%. Kermanshah oil sample had a higher 1,1-diphenyl-2-picrylhydrazyl radical scavenging (0.30-0.31 mg/ml), ability to prevent the bleaching of β-carotene (0.09-0.1 mg/ml), ferric reducing power (0.40-0.42 mg/ml) and thiobarbituric acid (0.004-0.006 Meq of malondialdehyde/g) values than that of ZEOs from Ilam, Kurdestan and Lorestan. The strong in vitro antimicrobial and antioxidant activities supports the traditional use of ZEO in the treatments of gastrointestinal diseases.
Antimicrobial activity of four essential oils against pigmenting Pseudomonas fluorescens and biofilmproducing Staphylococcus aureus of dairy origin

PubMed Central

Pedonese, Francesca; Fratini, Filippo; Pistelli, Luisa; Porta, Federica Maria; Ciccio, Pierluigi Di; Fischetti, Roberto; Turchi, Barbara; Nuvoloni, Roberta

2017-01-01

Essential oils (EOs) are mixtures of secondary metabolites of plant origin with many useful properties, among which the antimicrobial activity is also of interest for the food industry. EOs can exert their antimicrobial potential both directly, in food products and active packaging, and indirectly, as sanitizing and anti-biofilm agents of food facility surfaces. Aim of this research was to evaluate the antimicrobial activity of four EOs (bergamot, cinnamon, manuka and thyme) against Pseudomonas fluorescens and Staphylococcus aureus isolated from milk and dairy products. The chemical composition of EOs was evaluated by Gas Chromatography-Mass Spectrometry analysis. Minimum Inhibitory Concentration values were determined by a microplate method against 9 Ps. fluorescens from marketed mozzarella with blue discoloration defect, and 3 biofilm-producing S. aureus from milk. Reference ATCC strains were included. Pigment production activity by Ps. fluorescens was assessed both in culture and in cheese. EOs of manuka (leptospermone 23%) and thyme (carvacrol 30%, pcymene 20%, thymol 15%) showed the highest antimicrobial activity against S. aureus, MIC values were 0.012%-0.024% and 0.024% v/v, respectively; meanwhile EOs from thyme and cinnamon (cinnamaldehyde 55%) exhibited the best activity against Ps. fluorescens with MIC values of 0.098%-0.195% and 0.195%-0.391% v/v, respectively. The antimicrobial activity of these EOs is promising and they could be exploited in the dairy production chain. PMID:29564238
Chitosan-Starch Films with Natural Extracts: Physical, Chemical, Morphological and Thermal Properties

PubMed Central

Díaz-Zavala, Nancy P.; Melo-Banda, José A.; García-Alamilla, Ricardo; Martínez-Hernández, Ana L.; Zapién-Castillo, Samuel

2018-01-01

The aim of this study is to analyze the properties of a series of polysaccharide composite films, such as apparent density, color, the presence of functional groups, morphology, and thermal stability, as well as the correlation between them and their antimicrobial and optical properties. Natural antioxidants such as anthocyanins (from cranberry; blueberry and pomegranate); betalains (from beetroot and pitaya); resveratrol (from grape); and thymol and carvacrol (from oregano) were added to the films. Few changes in the position and intensity of the FTIR spectra bands were observed despite the low content of extract added to the films. Due to this fact, the antioxidants were extracted and identified by spectroscopic analysis; and they were also quantified using the Folin-Denis method and a gallic acid calibration curve, which confirmed the presence of natural antioxidants in the films. According to the SEM analysis, the presence of natural antioxidants has no influence on the film morphology because the stretch marks and white points that were observed were related to starch presence. On the other hand, the TGA analysis showed that the type of extract influences the total weight loss. The overall interpretation of the results suggests that the use of natural antioxidants as additives for chitosan-starch film preparation has a prominent impact on most of the critical properties that are decisive in making them suitable for food-packing applications. PMID:29329275
Characterization of Essential Oils Obtained from Abruzzo Autochthonous Plants: Antioxidant and Antimicrobial Activities Assessment for Food Application

PubMed Central

Pellegrini, Marika; Chaves-López, Clemencia; Mazzarrino, Giovanni; D’Amato, Serena; Lo Sterzo, Claudio

2018-01-01

In the present study, the essential oils (EOs) of some officinal plants from Abruzzo territory (Italy) were evaluated for their antimicrobial and antioxidant activities and their volatile fraction chemical characterization. The EOs were extracted from Rosmarinus officinalis, Origanum vulgare, Salvia officinalis, Mentha piperita, Allium sativum, Foeniculum vulgare, Satureja montana, Thymus vulgaris and Coriandrum sativum seeds. The antimicrobial activity was screened against thirteen Gram-positive and Gram-negative strains to determine the Minimal Inhibitory Concentration (MIC). The total phenolic content (TPC) and the antioxidant capacity (AOC) were assessed by means of Folin-Ciocâlteu method, and Trolox Equivalent Antioxidant Capacity with 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (TEAC/ABTS), Ferric Reducing Antioxidant Power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays respectively. Among the nine EOs tested, T. vulgaris, S. montana, O. vulgare and C. sativum EOs showed MIC values ranging from 0.625 to 5 μL/mL. The AOC and TPC results for these species were also interesting. The major components for these EOs were thymol for T. vulgaris (44%) and O. vulgare (40%), linalool (77%) for C. sativum, and carvacrol for S. montana (54%). The results allowed the study to establish that these EOs are good candidates for potential application as biopreservatives in foods and/or food manufacture environments. PMID:29393893
Chitosan-Starch Films with Natural Extracts: Physical, Chemical, Morphological and Thermal Properties.

PubMed

Lozano-Navarro, Jessica I; Díaz-Zavala, Nancy P; Velasco-Santos, Carlos; Melo-Banda, José A; Páramo-García, Ulises; Paraguay-Delgado, Francisco; García-Alamilla, Ricardo; Martínez-Hernández, Ana L; Zapién-Castillo, Samuel

2018-01-12

The aim of this study is to analyze the properties of a series of polysaccharide composite films, such as apparent density, color, the presence of functional groups, morphology, and thermal stability, as well as the correlation between them and their antimicrobial and optical properties. Natural antioxidants such as anthocyanins (from cranberry; blueberry and pomegranate); betalains (from beetroot and pitaya); resveratrol (from grape); and thymol and carvacrol (from oregano) were added to the films. Few changes in the position and intensity of the FTIR spectra bands were observed despite the low content of extract added to the films. Due to this fact, the antioxidants were extracted and identified by spectroscopic analysis; and they were also quantified using the Folin-Denis method and a gallic acid calibration curve, which confirmed the presence of natural antioxidants in the films. According to the SEM analysis, the presence of natural antioxidants has no influence on the film morphology because the stretch marks and white points that were observed were related to starch presence. On the other hand, the TGA analysis showed that the type of extract influences the total weight loss. The overall interpretation of the results suggests that the use of natural antioxidants as additives for chitosan-starch film preparation has a prominent impact on most of the critical properties that are decisive in making them suitable for food-packing applications.
Effect of cytokinins on in vitro multiplication, volatiles composition and rosmarinic acid content of Thymus leucotrichus Hal. shoots.

PubMed

Bekircan, Tuba; Yaşar, Ahmet; Yıldırım, Sercan; Sökmen, Münevver; Sökmen, Atalay

2018-03-01

An efficient in vitro multiplication protocol was designed to Thymus leucotrichus , a subshrub and perennial herb growing naturally in the Northwest of Turkey. Of all basal media studied, Murashige and Skoog medium was found to be superior to the others, providing higher shoot formation and the maximum shoot length. Varying concentrations of cytokinins, i.e., 6-benzyladenine, thidiazuron, 2-isopentenyladenine and kinetin were supplemented in the nutrient media to observe their effects on shoot development and biomass. Rosmarinic acid content and volatile compositions of both naturally growing plants and in vitro multiplied plantlets were also evaluated. 6-benzyladenine (1.0 mg/L) and kinetin (0.5 mg/L) were found to be optimum for shoot number and shoot elongation, respectively. Thidiazuron (1.0 mg/L) was superior for biomass production. Rosmarinic acid content of in vitro multiplied plants was found to be higher than that of wild plants, reaching a maximum with 0.5 mg/L 2-isopentenyladenine, which yielded 10.15 mg/g dry weight. The highest thymol content was obtained with 1.0 mg/L kinetin (55.82%), while thidiazuron (0.1 mg/L) increased carvacrol production (12.53%). Overall, Murashige and Skoog medium supplemented with 1.0 mg/L kinetin was determined to be the most favorable medium studied.
Supercritical fluid extraction of oregano (Origanum vulgare) essentials oils: anti-inflammatory properties based on cytokine response on THP-1 macrophages.

PubMed

Ocaña-Fuentes, A; Arranz-Gutiérrez, E; Señorans, F J; Reglero, G

2010-06-01

Two fractions (S1 and S2) of an oregano (Origanum vulgare) extract obtained by supercritical fluid extraction have been used to test anti-inflammatory effects on activated human THP-1 cells. The main compounds present in the supercritical extract fractions of oregano were trans-sabinene hydrate, thymol and carvacrol. Fractions toxicity was assessed using the mitochondrial-respiration-dependent 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) reduction method for several concentrations during 24 and 48 h of incubation. Concentrations higher than 30 microg/mL of both supercritical S1 and S2 oregano fractions caused a reduction in cell viability in a dose-dependent manner. Oxidized-LDLs (oxLDLs) activated THP-1 macrophages were used as cellular model of atherogenesis and the release/secretion of cytokines (TNT-alpha, IL-1beta, IL-6 and IL-10) and their respective mRNA expressions were quantified both in presence or absence of supercritical oregano extracts. The results showed a decrease in pro-inflammatory TNF-alpha, IL-1beta and IL-6 cytokines synthesis, as well as an increase in the production of anti-inflammatory cytokine IL-10. These results may suggest an anti-inflammatory effect of oregano extracts and their compounds in a cellular model of atherosclerosis. Copyright 2010 Elsevier Ltd. All rights reserved.

Molecular characterisation of a bio-based active packaging containing Origanum vulgare L. essential oil using pyrolysis gas chromatography-mass spectrometry.

PubMed

Llana-Ruíz-Cabello, María; Pichardo, Silvia; Jiménez-Morillo, Nicasio T; Bermúdez, José M; Aucejo, Susana; González-Vila, Francisco J; Cameán, Ana M; González-Pérez, José A

2016-07-01

Environmental, economic and safety challenges motivate shift towards safer materials for food packaging. New bioactive packaging techniques, i.e. addition of essential plant oils (EOs), are gaining attention by creating barriers to protect products from spoilage. Analytical pyrolysis gas chromatography-mass spectrometry (Py-GC-MS) was used to fingerprint a bioactive polylactic acid (PLA) with polybutylene succinate (PBS) (950 g kg(-1) :50 g kg(-1) ) film extruded with variable quantities (0, 20, 50 and 100 g kg(-1) ) of Origanum vulgare EO. Main PLA:PBS pyrolysis products were lactide enantiomers and monomer units from the major PLA fraction and succinic acid anhydride from the PBS fraction. Oregano EO pyrolysis released cymene, terpinene and thymol/carvacrol peaks as diagnostic peaks for EO. In fact, linear correlation coefficients better than 0.950R(2) value (P < 0.001) were found between the chromatographic area of the diagnostic peaks and the amount of oregano EO in the bioplastic. The pyrolytic behaviour of a bio-based active package polymer including EO is studied in detail. Identified diagnostic compounds provide a tool to monitor the quantity of EO incorporated into the PLA:PBS polymeric matrix. Analytical pyrolysis is proposed as a rapid technique for the identification and quantification of additives within bio-based plastic matrices. © 2015 Society of Chemical Industry. © 2015 Society of Chemical Industry.
Eugenol-loaded chitosan nanoparticles: II. Application in bio-based plastics for active packaging.

PubMed

Woranuch, Sarekha; Yoksan, Rangrong

2013-07-25

The aim of the present research was to study the possibility of using eugenol-loaded chitosan nanoparticles as antioxidants for active bio-based packaging material. Eugenol-loaded chitosan nanoparticles were incorporated into thermoplastic flour (TPF) - a model bio-based plastic - through an extrusion process at temperatures above 150°C. The influences of eugenol-loaded chitosan nanoparticles on crystallinity, morphology, thermal properties, radical scavenging activity, reducing power, tensile properties and barrier properties of TPF were investigated. Although the incorporation of 3% (w/w) of eugenol-loaded chitosan nanoparticles significantly reduced the extensibility and the oxygen barrier property of TPF, it provided antioxidant activity and improved the water vapor barrier property. In addition, TPF containing eugenol-loaded chitosan nanoparticles exhibited superior radical scavenging activity and stronger reducing power compared with TPF containing naked eugenol. The results suggest the applicability of TPF containing eugenol-loaded chitosan nanoparticles as an antioxidant active packaging material. Copyright © 2012 Elsevier Ltd. All rights reserved.
Thymol kills bacteria, reduces biofilm formation, and protects mice against a fatal infection of Actinobacillus pleuropneumoniae strain L20.

PubMed

Wang, Lei; Zhao, Xueqin; Zhu, Chunling; Xia, Xiaojing; Qin, Wanhai; Li, Mei; Wang, Tongzhao; Chen, Shijun; Xu, Yanzhao; Hang, Bolin; Sun, Yawei; Jiang, Jinqing; Richard, Langford Paul; Lei, Liancheng; Zhang, Gaiping; Hu, Jianhe

2017-05-01

Actinobacillus pleuropneumoniae is the causative agent of the highly contagious and deadly respiratory infection porcine pleuropneumonia, resulting in serious losses to the pig industry worldwide. Alternative to antibiotics are urgently needed due to the serious increase in antimicrobial resistance. Thymol is a monoterpene phenol and efficiently kills a variety of bacteria. This study found that thymol has strong bactericidal effects on the A. pleuropneumoniae 5b serotype strain, an epidemic strain in China. Sterilization occurred rapidly, and the minimum inhibitory concentration (MIC) is 31.25μg/mL; the A. pleuropneumoniae density was reduced 1000 times within 10min following treatment with 1 MIC. Transmission electron microscopy (TEM) analysis revealed that thymol could rapidly disrupt the cell walls and cell membranes of A. pleuropneumoniae, causing leakage of cell contents and cell death. In addition, treatment with thymol at 0.5 MIC significantly reduced the biofilm formation of A. pleuropneumoniae. Quantitative RT-PCR results indicated that thymol treatment significantly increased the expression of the virulence genes purC, tbpB1 and clpP and down-regulated ApxI, ApxII and Apa1 expression in A. pleuropneumoniae. Therapeutic analysis of a murine model showed that thymol (20mg/kg) protected mice from a lethal dose of A. pleuropneumoniae, attenuated lung pathological lesions. This study is the first to report the use of thymol to treat A. pleuropneumoniae infection, establishing a foundation for the development of new antimicrobials. Copyright © 2017 Elsevier B.V. All rights reserved.
Monoterpene phenolic compound thymol promotes browning of 3T3-L1 adipocytes.

PubMed

Choi, Jae Heon; Kim, Sang Woo; Yu, Rina; Yun, Jong Won

2017-10-01

Appearance of brown-like adipocytes within white adipose tissue depots (browning) is associated with improved metabolic phenotypes, and thus a wide variety of dietary agents that contribute to browning of white adipocytes are being studied. The aim of this study was to assess the browning effect of thymol, a dietary monoterpene phenolic compound, in 3T3-L1 white adipocytes. Thymol-induced fat browning was investigated by determining expression levels of brown fat-specific genes and proteins by real-time RT-PCR and immunoblot analysis, respectively. Moreover, the molecular mechanism underlying the fat-browning effect of thymol was investigated by determining expression levels of key players responsible for browning in the presence of kinase inhibitors. Thymol promoted mitochondrial biogenesis and enhanced expression of a core set of brown fat-specific markers as well as increased protein levels of PPARγ, PPARδ, pAMPK, pACC, HSL, PLIN, CPT1, ACO, PGC-1α, and UCP1, suggesting its possible role in browning of white adipocytes, augmentation of lipolysis, fat oxidation, and thermogenesis, and reduction of lipogenesis. Increased expression of UCP1 and other brown fat-specific markers by thymol was tightly coordinated with activation of β3-AR as well as AMPK, PKA, and p38 MAPK. Our findings suggest that 3T3-L1 is a potential cell model for screening browning agents. Thymol plays multiple modulatory roles in the form of inducing the brown-like phenotype as well as enhancing lipid metabolism. Thus, thymol may be explored as a potentially promising food additive for prevention of obesity.
Assessment of tolerance induction by Origanum vulgare L. essential oil or carvacrol in Pseudomonas aeruginosa cultivated in a meat-based broth and in a meat model.

PubMed

da Silva Luz, Isabelle; Gomes-Neto, Nelson Justino; Magnani, Marciane; de Souza, Evandro Leite

2015-12-01

This study assessed the efficacy of Origanum vulgare L. essential oil (OVEO) and carvacrol in inhibiting the growth of Pseudomonas aeruginosa ATCC 9027, as well as the development of direct tolerance and cross-tolerance when this bacterium was challenged with sublethal amounts of these substances in a meat-based broth and in a meat model. OVEO and carvacrol at their minimum inhibitory concentrations (MICs), 1/2 MIC and 1/4 MIC decreased the viable cell counts of P. aeruginosa in meat-based broth. Direct tolerance or cross-tolerance was not induced after exposure of the assayed bacterial strain to sublethal amounts of OVEO or carvacrol in meat-based broth and in an artificially contaminated ground beef. Bacterial cells progressively subcultured in meat-based broth with increasing amounts of the tested substances survived up to the MIC of OVEO and to 1/2 MIC of carvacrol. The results reveal a lack of induction of tolerance in P. aeruginosa by exposure to OVEO or carvacrol in meat-based broth and in a meat model. © The Author(s) 2014.
Antimicrobial paper based on a soy protein isolate or modified starch coating including carvacrol and cinnamaldehyde.

PubMed

Arfa, Afef Ben; Preziosi-Belloy, Laurence; Chalier, Pascale; Gontard, Nathalie

2007-03-21

Soy protein isolates (SPI) and octenyl-succinate (OSA) modified starch were used as paper coating and inclusion matrices of two antimicrobial compounds: cinnamaldehyde and carvacrol. Antimicrobial compound losses from the coated papers were evaluated after the coating and drying process, and the two matrices demonstrated retention ability that depended on the compound nature and concentration. Whereas carvacrol losses ranged between 12 and 45%, cinnamaldehyde losses varied from 43 to 76%. The losses were always higher from OSA-starch-coated papers than from SPI-coated papers. During storage in accelerated conditions, at 30 degrees C and 60% relative humidity, carvacrol retention from coated papers was found to be similar whatever the coating matrices and the carvacrol rate. In contrast, the retention from SPI-coated papers was particularly high for the cinnamaldehyde concentration of 30% (w/w) compared to the lowest (10% w/w) or highest concentration (60% w/w). Compared to carvacrol, faster release was observed, particurlarly when OSA-starch was used. The antimicrobial properties of the coated papers were shown against Escherichia coli and Botrytis cinerea and explained by favorable conditions of total release of the antimicrobial agents.
40 CFR 180.1240 - Thymol; exemption from the requirement of a tolerance.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 23 2010-07-01 2010-07-01 false Thymol; exemption from the requirement of a tolerance. 180.1240 Section 180.1240 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) PESTICIDE PROGRAMS TOLERANCES AND EXEMPTIONS FOR PESTICIDE CHEMICAL RESIDUES IN FOOD Exemptions From Tolerances § 180.1240 Thymol;...
Encapsulation of eugenol from clove oil using casein micelle for solid preparation

NASA Astrophysics Data System (ADS)

Wijayanto, Andri; Putri, Yeshinta Risky Priasmara; Hermansyah, Heri; Sahlan, Muhamad

2017-02-01

Liquid preparation of eugenol in clove oil form is one of eugenol preparation form that is easiest to get it nowadays in many level of purity. The problem is the liquid preparation of chemical is often not easy to handle than the solid one. In this study, we observe the effectivity of cow milk casein in case of encapsulating eugenol from clove oil for creating the solid preparation of eugenol in nanoscale size. The result is 63.86% eugenol from clove oil can be encapsulated by the casein. The average particle diameter is about 377.5 nm, with loading capacity until 67.2%.
No induction of antimicrobial resistance in Staphylococcus aureus and Listeria monocytogenes during continuous exposure to eugenol and citral.

PubMed

Apolónio, Joana; Faleiro, Maria L; Miguel, Maria G; Neto, Luís

2014-05-01

The aim of this study was to evaluate the adaptation response of Staphylococcus aureus, methicillin-resistant S. aureus (MRSA), and Listeria monocytogenes to the essential oil (EO), eugenol, and citral. The minimum inhibitory concentration of eugenol and citral was determined by agar dilution and microdilution. Adaptation to eugenol and citral was done by sequential exposure of the pathogens to increasing concentrations of the essential oils. The M2-A9 standard was used to determine the antibiotic susceptibility. The effect of eugenol and citral on the adherence ability was evaluated by the crystal violet assay. The impact of adaptation to eugenol on virulence was estimated using the Galleria mellonella model. No development of resistance to the components and antibiotics was observed in the adapted cells of S. aureus, MRSA, and L. monocytogenes. Eugenol and citral at subinhibitory concentration reduced the bacterial adherence. Adaptation to subinhibitory concentration of eugenol affected the virulence potential of S. aureus, MRSA, and L. monocytogenes. Eugenol and citral do not pose a risk of resistance development in a continuous mode of use. These EO components showed a high efficacy as antistaphylococcal and antilisterial biofilm agents. Adaptation at subinhibitory concentration of eugenol protected the larvae against listerial and staphylococcal infection. © 2014 Federation of European Microbiological Societies. Published by John Wiley & Sons Ltd. All rights reserved.
Global transcriptional response of Escherichia coli MG1655 cells exposed to the oxygenated monoterpenes citral and carvacrol.

PubMed

Chueca, Beatriz; Pérez-Sáez, Elisa; Pagán, Rafael; García-Gonzalo, Diego

2017-09-18

DNA microarrays were used to study the mechanism of bacterial inactivation by carvacrol and citral. After 10-min treatments of Escherichia coli MG1655 cells with 100 and 50ppm of carvacrol and citral, 76 and 156 genes demonstrated significant transcriptional differences (p≤0.05), respectively. Among the up-regulated genes after carvacrol treatment, we found gene coding for multidrug efflux pumps (acrA, mdtM), genes related to phage shock response (pspA, pspB, pspC, pspD, pspF and pspG), biosynthesis of arginine (argC, argG, artJ), and purine nucleotides (purC, purM). In citral-treated cells, transcription of purH and pyrB and pyrI was 2 times higher. Deletion of several differentially expressed genes confirmed the role of ygaV, yjbO, pspC, sdhA, yejG and ygaV in the mechanisms of E. coli inactivation by carvacrol and citral. These results would indicate that citral and carvacrol treatments cause membrane damage and activate metabolism through the production of nucleotides required for DNA and RNA synthesis and metabolic processes. Comparative transcriptomics of the response of E. coli to a heat treatment, which caused a significant change of the transcription of 1422 genes, revealed a much weaker response to both individual constituents of essential oils (ICs).·Thus, inactivation by citral or carvacrol was not multitarget in nature. Copyright © 2017 Elsevier B.V. All rights reserved.
Effectiveness of eugenol sedation to reduce the metabolic rates of cool and warm water fish at high loading densities

USGS Publications Warehouse

Cupp, Aaron R.; Hartleb, Christopher F.; Fredricks, Kim T.; Gaikowski, Mark P.

2016-01-01

Effects of eugenol (AQUI-S®20E, 10% active eugenol) sedation on cool water, yellow perch Perca flavescens (Mitchill), and warm water, Nile tilapia Oreochromis niloticus L. fish metabolic rates were assessed. Both species were exposed to 0, 10, 20 and 30 mg L−1 eugenol using static respirometry. In 17°C water and loading densities of 60, 120 and 240 g L−1, yellow perch controls (0 mg L−1 eugenol) had metabolic rates of 329.6–400.0 mg O2 kg−1 h−1, while yellow perch exposed to 20 and 30 mg L−1 eugenol had significantly reduced metabolic rates of 258.4–325.6 and 189.1–271.0 mg O2 kg−1 h−1 respectively. Nile tilapia exposed to 30 mg L−1 eugenol had a significantly reduced metabolic rate (424.5 ± 42.3 mg O2 kg−1 h−1) relative to the 0 mg L−1 eugenol control (546.6 ± 53.5 mg O2 kg−1 h−1) at a loading density of 120 g L−1 in 22°C water. No significant differences in metabolic rates for Nile tilapia were found at 240 or 360 g L−1 loading densities when exposed to eugenol. Results suggest that eugenol sedation may benefit yellow perch welfare at high densities (e.g. live transport) due to a reduction in metabolic rates, while further research is needed to assess the benefits of eugenol sedation on Nile tilapia at high loading densities.
Thymol inhibits Staphylococcus aureus internalization into bovine mammary epithelial cells by inhibiting NF-κB activation.

PubMed

Wei, Zhengkai; Zhou, Ershun; Guo, Changming; Fu, Yunhe; Yu, Yuqiang; Li, Yimeng; Yao, Minjun; Zhang, Naisheng; Yang, Zhengtao

2014-01-01

Bovine mastitis is one of the most costly and prevalent diseases in the dairy industry and is characterised by inflammatory and infectious processes. Staphylococcus aureus (S. aureus), a Gram-positive organism, is a frequent cause of subclinical, chronic mastitis. Thymol, a monocyclic monoterpene compound isolated from Thymus vulgaris, has been reported to have antibacterial properties. However, the effect of thymol on S. aureus internalization into bovine mammary epithelial cells (bMEC) has not been investigated. In this study, we evaluated the effect of thymol on S. aureus internalization into bMEC, the expression of tracheal antimicrobial peptide (TAP) and β-defensin (BNBD5), and the inhibition of NF-κB activation in bMEC infected with S. aureus. Our results showed that thymol (16-64 μg/ml) could reduce the internalization of S. aureus into bMEC and down-regulate the mRNA expression of TAP and BNBD5 in bMEC infected with S. aureus. In addition, thymol was found to inhibit S. aureus-induced nitric oxide (NO) production in bMEC and suppress S. aureus-induced NF-κB activation in a dose-dependent manner. In conclusion, these results indicated that thymol inhibits S. aureus internalization into bMEC by inhibiting NF-κB activation. Copyright © 2014 Elsevier Ltd. All rights reserved.
Oxygenated monoterpenes citral and carvacrol cause oxidative damage in Escherichia coli without the involvement of tricarboxylic acid cycle and Fenton reaction.

PubMed

Chueca, Beatriz; Pagán, Rafael; García-Gonzalo, Diego

2014-10-17

Oxygenated monoterpenes citral and carvacrol are common constituents of many essential oils (EOs) that have been extensively studied as antimicrobial agents but whose mechanisms of microbial inactivation have not been totally elucidated. A recent study described a mechanism of Escherichia coli death for (+)-limonene, a hydrocarbon monoterpene also frequently present in EOs, similar to the common mechanism proposed for bactericidal antibiotics. This mechanism involves the formation of Fenton-mediated hydroxyl radical, a reactive oxygen species (ROS), via tricarboxylic acid (TCA) cycle, which would ultimately inactivate cells. Our objective was to determine whether E. coli MG1655 inactivation by citral and carvacrol follows a similar mechanism of cell death. Challenging experiments with 300μL/L citral and 100μL/L carvacrol inactivated at least 2.5log10cycles of exponentially growing cells in 3h under aerobic conditions. The presence of thiourea (an ROS scavenger) reduced cell inactivation in 2log10cycles, demonstrating the role of ROS in cell death. Decreased resistance of a ΔrecA mutant (deficient in an enzyme involved in SOS response to DNA damage) indicated that citral and carvacrol caused oxidative damage to DNA. Although the mechanism of E. coli inactivation by carvacrol and citral was similarly mediated by ROS, their formation did not follow the same pathways described for (+)-limonene and bactericidal drugs because neither Fenton reaction nor NADH production via the TCA cycle was involved in cell death. Moreover, further experiments demonstrated antimicrobial activity of citral and carvacrol in anaerobic environments without the involvement of ROS. As a consequence, cell death by carvacrol and citral in anaerobiosis follows a different mechanism than that observed under aerobic conditions. These results demonstrated a different mechanism of inactivation by citral and carvacrol with regard to (+)-limonene and bactericidal antibiotics, indicating the complexity of the mechanisms of bacterial inactivation among EO constituents. Advancements in the description of these mechanisms will help in extending and improving the use of these compounds as natural antimicrobials. Copyright © 2014 Elsevier B.V. All rights reserved.
In vivo activity of albendazole in combination with thymol against Echinococcus multilocularis.

PubMed

Albani, Clara María; Pensel, Patricia Eugenia; Elissondo, Natalia; Gambino, Guillermo; Elissondo, María Celina

2015-09-15

Human alveolar echinococcosis (AE) is caused by the fox tapeworm Echinococcus multilocularis and is usually lethal if left untreated. The current strategy for treating human AE is surgical resection of the parasite mass complemented by chemotherapy with benzimidazole compounds. However, reliable chemotherapeutic alternatives have not yet been developed stimulating the research of new treatment strategies such as the use of medicinal plants. The aim of the current study was to investigate the efficacy of the combination albendazole (ABZ)+thymol on mice infected with E. multilocularis metacestodes. For this purpose, mice infected with parasite material were treated daily for 20 days with ABZ (5 mg/kg), thymol (40 mg/kg) or ABZ (5 mg/kg)+thymol (40 mg/kg) or left untreated as controls. After mice were euthanized, cysts were removed from the peritoneal cavity and the treatment efficacy was evaluated by the mean cysts weight, viability of protoscoleces and ultrastructural changes of cysts and protoscoleces. The application of thymol or the combination of ABZ+thymol resulted in a significant reduction of the cysts weight compared to untreated mice. We also found that although ABZ and thymol had a scolicidal effect, the combination of the two compounds had a considerably stronger effect showing a reduction in the protoscoleces viability of 62%. These results were also corroborated by optical microscopy, SEM and TEM. Protoscoleces recovered from ABZ or thymol treated mice showed alterations as contraction of the soma region, rostellar disorganization and presence of blebs in the tegument. However both drugs when combined lead to a total loss of the typical morphology of protoscoleces. All cysts removed from control mice appeared intact and no change in ultrastructure was detected. In contrast, cysts developed in mice treated with ABZ revealed changes in the germinal layer as reduction in cell number, while the treatment with thymol or the ABZ+thymol combination predominantly showed presence of cell debris. On the other hand, no differences were found in alkaline phosphatase (AP), glutamate oxaloacetate transaminase (GOT) and glutamate pyruvate transaminase (GPT) activities between control and treated mice, indicating the lack of toxicity of the different drug treatments during the experiment. Because combined ABZ+thymol treatment exhibited higher treatment efficiency compared with the drugs applied separately against murine experimental alveolar echinococcosis, we propose it would be a useful option for the treatment of human AE. Copyright © 2015 Elsevier B.V. All rights reserved.
Fabrication and characterization of novel antimicrobial films derived from thymol-loaded zein-sodium caseinate (SC) nanoparticles.

PubMed

Li, Kang-Kang; Yin, Shou-Wei; Yang, Xiao-Quan; Tang, Chuan-He; Wei, Zi-Hao

2012-11-21

The objective of this research was to fabricate novel antimicrobial films based on zein colloidal nanoparticles coated with sodium caseinate (SC), an emulsifier/stabilizer. Thymol-loaded zein-SC nanoparticles were prepared using an antisolvent technique, with the average particle size and zeta potential about 200 ± 20 nm and -40 mV, respectively. Zein-SC nanoparticle-based films exhibited higher mechanical resistance and water barrier capacity than the SC films and concomitant good extensibility as compared with zein films. Thymol loadings endowed zein-SC nanoparticle-based films with antimicrobial activity against Escherichia coli and Salmonella as well as DPPH radical scavenging activity. Water vapor permeability, microstructure, mechanical, and controlled release properties of the films were evaluated. The possible relationship between some selected physical properties and microstructure were also discussed. Atomic force microscopy (AFM) analysis indicated that thymol loadings resulted in the emergence phenomena of the nanoparticles to form large particles or packed structure, consisting of clusters of nanoparticles, within the film matrix, in a thymol loading dependent manner. The appearance of large particles or an agglomerate of particles may weaken the compactness of protein network of films and thus impair the water barrier capacity, mechanical resistance, and extensibility of the films. The release kinetics of thymol from nanoparticle-based films can be described as a two-step biphasic process, that is, an initial burst effect followed by subsequent slower release, and zein-SC nanoparticles within the films matrices gave them the ability to sustain the release of thymol. In addition, a schematic illustration of the formation pathway of zein-SC nanoparticle-based films with or without thymol was proposed to illuminate the possible relationship between some selected physical properties and the microstructure of the films.
Potential Dual Role of Eugenol in Inhibiting Advanced Glycation End Products in Diabetes: Proteomic and Mechanistic Insights

PubMed Central

Singh, Priyanka; Jayaramaiah, Ramesha H.; Agawane, Sachin B.; Vannuruswamy, Garikapati; Korwar, Arvind M.; Anand, Atul; Dhaygude, Vitthal S.; Shaikh, Mahemud L.; Joshi, Rakesh S.; Boppana, Ramanamurthy; Kulkarni, Mahesh J.; Thulasiram, Hirekodathakallu V.; Giri, Ashok P.

2016-01-01

Medicinally important genus Ocimum harbors a vast pool of chemically diverse metabolites. Current study aims at identifying anti-diabetic candidate compounds from Ocimum species. Major metabolites in O. kilimandscharicum, O. tenuiflorum, O. gratissimum were purified, characterized and evaluated for anti-glycation activity. In vitro inhibition of advanced glycation end products (AGEs) by eugenol was found to be highest. Preliminary biophysical analysis and blind docking studies to understand eugenol-albumin interaction indicated eugenol to possess strong binding affinity for surface exposed lysines. However, binding of eugenol to bovine serum albumin (BSA) did not result in significant change in secondary structure of protein. In vivo diabetic mice model studies with eugenol showed reduction in blood glucose levels by 38% likely due to inhibition of α-glucosidase while insulin and glycated hemoglobin levels remain unchanged. Western blotting using anti-AGE antibody and mass spectrometry detected notably fewer AGE modified peptides upon eugenol treatment both in vivo and in vitro. Histopathological examination revealed comparatively lesser lesions in eugenol-treated mice. Thus, we propose eugenol has dual mode of action in combating diabetes; it lowers blood glucose by inhibiting α-glucosidase and prevents AGE formation by binding to ε-amine group on lysine, protecting it from glycation, offering potential use in diabetic management. PMID:26739611
Potential Dual Role of Eugenol in Inhibiting Advanced Glycation End Products in Diabetes: Proteomic and Mechanistic Insights.

PubMed

Singh, Priyanka; Jayaramaiah, Ramesha H; Agawane, Sachin B; Vannuruswamy, Garikapati; Korwar, Arvind M; Anand, Atul; Dhaygude, Vitthal S; Shaikh, Mahemud L; Joshi, Rakesh S; Boppana, Ramanamurthy; Kulkarni, Mahesh J; Thulasiram, Hirekodathakallu V; Giri, Ashok P

2016-01-07

Medicinally important genus Ocimum harbors a vast pool of chemically diverse metabolites. Current study aims at identifying anti-diabetic candidate compounds from Ocimum species. Major metabolites in O. kilimandscharicum, O. tenuiflorum, O. gratissimum were purified, characterized and evaluated for anti-glycation activity. In vitro inhibition of advanced glycation end products (AGEs) by eugenol was found to be highest. Preliminary biophysical analysis and blind docking studies to understand eugenol-albumin interaction indicated eugenol to possess strong binding affinity for surface exposed lysines. However, binding of eugenol to bovine serum albumin (BSA) did not result in significant change in secondary structure of protein. In vivo diabetic mice model studies with eugenol showed reduction in blood glucose levels by 38% likely due to inhibition of α-glucosidase while insulin and glycated hemoglobin levels remain unchanged. Western blotting using anti-AGE antibody and mass spectrometry detected notably fewer AGE modified peptides upon eugenol treatment both in vivo and in vitro. Histopathological examination revealed comparatively lesser lesions in eugenol-treated mice. Thus, we propose eugenol has dual mode of action in combating diabetes; it lowers blood glucose by inhibiting α-glucosidase and prevents AGE formation by binding to ε-amine group on lysine, protecting it from glycation, offering potential use in diabetic management.
An R2R3-MYB Transcription Factor Regulates Eugenol Production in Ripe Strawberry Fruit Receptacles1

PubMed Central

Medina-Puche, Laura; Molina-Hidalgo, Francisco Javier; Boersma, Maaike; Schuurink, Robert C.; López-Vidriero, Irene; Solano, Roberto; Franco-Zorrilla, José-Manuel; Caballero, José Luis; Blanco-Portales, Rosario; Muñoz-Blanco, Juan

2015-01-01

Eugenol is a volatile phenylpropanoid that contributes to flower and ripe fruit scent. In ripe strawberry (Fragaria × ananassa) fruit receptacles, eugenol is biosynthesized by eugenol synthase (FaEGS2). However, the transcriptional regulation of this process is still unknown. We have identified and functionally characterized an R2R3 MYB transcription factor (EMISSION OF BENZENOID II [FaEOBII]) that seems to be the orthologous gene of PhEOBII from Petunia hybrida, which contributes to the regulation of eugenol biosynthesis in petals. The expression of FaEOBII was ripening related and fruit receptacle specific, although high expression values were also found in petals. This expression pattern of FaEOBII correlated with eugenol content in both fruit receptacle and petals. The expression of FaEOBII was repressed by auxins and activated by abscisic acid, in parallel to the ripening process. In ripe strawberry receptacles, where the expression of FaEOBII was silenced, the expression of CINNAMYL ALCOHOL DEHYDROGENASE1 and FaEGS2, two structural genes involved in eugenol production, was down-regulated. A subsequent decrease in eugenol content in ripe receptacles was also observed, confirming the involvement of FaEOBII in eugenol metabolism. Additionally, the expression of FaEOBII was under the control of FaMYB10, another R2R3 MYB transcription factor that regulates the early and late biosynthetic genes from the flavonoid/phenylpropanoid pathway. In parallel, the amount of eugenol in FaMYB10-silenced receptacles was also diminished. Taken together, these data indicate that FaEOBII plays a regulating role in the volatile phenylpropanoid pathway gene expression that gives rise to eugenol production in ripe strawberry receptacles. PMID:25931522
Preparation, characterization and in vitro release study of carvacrol-loaded chitosan nanoparticles.

PubMed

Keawchaoon, Lalita; Yoksan, Rangrong

2011-05-01

The fabrication of carvacrol-loaded chitosan nanoparticles was achieved by a two-step method, i.e., oil-in-water emulsion and ionic gelation of chitosan with pentasodium tripolyphosphate. The obtained particles possessed encapsulation efficiency (EE) and loading capacity (LC) in the ranges of 14-31% and 3-21%, respectively, when the initial carvacrol content was 0.25-1.25 g/g of chitosan. The individual particles exhibited a spherical shape with an average diameter of 40-80 nm, and a positively charged surface with a zeta potential value of 25-29 mV. The increment of initial carvacrol content caused a reduction of surface charge. Carvacrol-loaded chitosan nanoparticles showed antimicrobial activity against Staphylococcus aureus, Bacillus cereus and Escherichia coli with an MIC of 0.257 mg/mL. The release of carvacrol from chitosan nanoparticles reached plateau level on day 30, with release amounts of 53% in acetate buffer solution with pH of 3, and 23% and 33% in phosphate buffer solutions with pH of 7 and 11, respectively. The release mechanism followed a Fickian behavior. The release rate was superior in an acidic medium to either alkaline or neutral media, respectively. Copyright © 2011 Elsevier B.V. All rights reserved.
Effects of a herbal gel containing carvacrol and chalcones on alveolar bone resorption in rats on experimental periodontitis.

PubMed

Botelho, Marco Antonio; Rao, Vietla Satyanarayana; Montenegro, Danusa; Bandeira, Mary Anne Menezes; Fonseca, Said Gonçalves Cruz; Nogueira, Nadia Accioly Pinto; Ribeiro, Ronaldo Albuquerque; Brito, Gerly Anne Castro

2008-04-01

Carvacrol and dimeric chalcones are the respective bioactive components of Lippia sidoides and Myracrodruon urundeuva, popular medicinal plants of Northeastern Brazil with proven antimicrobial and antiinflammatory properties. Periodontal disease is associated with inflammation and microbiological proliferation, thus the study aimed to investigate the effect of a topical gel based on carvacrol and chalcones in the experimental periodontal disease (EPD) in rats. Animals were treated with carvacrol and/or chalcones gel, immediately after EPD induction, three times a day for 11 days. Appropriate controls were included in the study. Animals were weighed daily. They were killed on day 11, the mandibles dissected and alveolar bone loss was measured. The periodontium were examined at histopathology and the neutrophil influx into the gingiva was assayed using myeloperoxidase activity. The bacterial flora were assessed through culture of the gingival tissue. Alveolar bone loss was significantly (p < 0.05) inhibited by combined carvacrol and chalcones gel, compared with the vehicle and non-treated groups. The treatment with the combined gel reduced tissue lesion at histopathology, decreased myeloperoxidase activity in gingival tissue and inhibited the growth of oral microorganisms as well as the weight loss. Carvacrol and chalcones combination gel has a beneficial effect upon EPD in this model. (c) 2008 John Wiley & Sons, Ltd.

Apple, carrot, and hibiscus edible films containing the plant antimicrobials carvacrol and cinnamaldehyde inactivate Salmonella Newport on organic leafy greens in sealed plastic bags.

PubMed

Zhu, Libin; Olsen, Carl; McHugh, Tara; Friedman, Mendel; Jaroni, Divya; Ravishankar, Sadhana

2014-01-01

The objective of this study was to investigate the antimicrobial effects of carvacrol and cinnamaldehyde incorporated into apple, carrot, and hibiscus-based edible films against Salmonella Newport in bagged organic leafy greens. The leafy greens tested included organic Romaine and Iceberg lettuce, and mature and baby spinach. Each leafy green sample was washed, dip inoculated with S. Newport (10⁷ CFU/mL), and dried. Each sample was put into a Ziploc® bag. Edible films pieces were put into the Ziploc bag and mixed well. The bags were sealed and stored at 4 °C. Samples were taken at days 0, 3, and 7 for enumeration of survivors. On all leafy greens, 3% carvacrol films showed the best bactericidal effects against Salmonella. All 3 types of 3% carvacrol films reduced the Salmonella population by 5 log₁₀ CFU/g at day 0 and 1.5% carvacrol films reduced Salmonella by 1 to 4 log₁₀ CFU/g at day 7. The films with 3% cinnamaldehyde showed 0.5 to 3 log reductions on different leafy greens at day 7. The films with 0.5% and 1.5% cinnamaldehyde and 0.5% carvacrol also showed varied reductions on different types of leafy greens. Edible films were the most effective against Salmonella on Iceberg lettuce. This study demonstrates the potential of edible films incorporated with carvacrol and cinnamaldehyde to inactivate S. Newport on organic leafy greens. © 2013 Institute of Food Technologists®
Effects of the essential oil constituent thymol and other neuroactive chemicals on flight motor activity and wing beat frequency in the blowfly Phaenicia sericata.

PubMed

Waliwitiya, Ranil; Belton, Peter; Nicholson, Russell A; Lowenberger, Carl A

2010-03-01

The effects were evaluated of the plant terpenoid thymol and eight other neuroactive compounds on flight muscle impulses (FMIs) and wing beat frequency (WBF) of tethered blowflies (Phaenicia sericata Meig.). The electrical activity of the dorsolongitudinal flight muscles was closely linked to the WBF of control insects. Topically applied thymol inhibited WBF within 15-30 min and reduced FMI frequency. Octopamine and chlordimeform caused a similar, early-onset bursting pattern that decreased in amplitude with time. Desmethylchlordimeform blocked wing beating within 60 min and generated a profile of continuous but lower-frequency FMIs. Fipronil suppressed wing beating and induced a pattern of continuous, variable-frequency spiking that diminished gradually over 6 h. Cypermethrin- and rotenone-treated flies had initial strong FMIs that declined with time. In flies injected with GABA, the FMIs were generally unidirectional and frequency was reduced, as was seen with thymol. Thymol readily penetrates the cuticle and interferes with flight muscle and central nervous function in the blowfly. The similarity of the action of thymol and GABA suggests that this terpenoid acts centrally in blowflies by mimicking or facilitating GABA action.
Antifungal activity and mode of action of thymol and its synergism with nystatin against Candida species involved with infections in the oral cavity: an in vitro study.

PubMed

de Castro, Ricardo Dias; de Souza, Trícia Murielly Pereira Andrade; Bezerra, Louise Morais Dornelas; Ferreira, Gabriela Lacet Silva; Costa, Edja Maria Melo de Brito; Cavalcanti, Alessandro Leite

2015-11-24

Limitations of antifungal agents used in the treatment of oral candidiasis, as the development of resistant strains, are known by the scientific community. In this context, the aim of this study was to evaluate the antifungal activity of thymol against Candida albicans, Candida tropicalis and Candida krusei strains and to determine its mode of action and synergistic effect when combined with the synthetic antifungal nystatin. The minimum inhibitory concentration (MIC) was determined using a microdilution technique, and the minimum fungicidal concentration (MFC) was determined via subculture sowing. The mode of action of thymol was established by verifying fungal growth in the presence of sorbitol or ergosterol. The fractional inhibitory concentration index (FIC) was determined using the checkerboard method. Thymol presented an antifungal effect, with MICs of 39 μg/mL for C. albicans and C. krusei and 78 μg/mL for C. tropicalis. The results of the antifungal test remained unchanged in the presence of sorbitol; however, the MIC value of thymol against C. albicans increased eight times (from 39.0 to 312.5 μg/mL) in presence of exogenous ergosterol. The combination of thymol and nystatin reduced the MIC values of both products by 87.4%, generating an FIC index of 0.25. Thymol was found to have a fungicidal effect on Candida species and a synergistic effect when combined with nystatin.
Antimicrobial activity of eugenol and essential oils containing eugenol: A mechanistic viewpoint.

PubMed

Marchese, Anna; Barbieri, Ramona; Coppo, Erika; Orhan, Ilkay Erdogan; Daglia, Maria; Nabavi, Seyed Fazel; Izadi, Morteza; Abdollahi, Mohammad; Nabavi, Seyed Mohammad; Ajami, Marjan

2017-11-01

Eugenol is a hydroxyphenyl propene, naturally occurring in the essential oils of several plants belonging to the Lamiaceae, Lauraceae, Myrtaceae, and Myristicaceae families. It is one of the major constituents of clove (Syzygium aromaticum (L.) Merr. & L.M. Perry, Myrtaceae) oil and is largely used in both foods and cosmetics as a flavoring agent. A large body of recent scientific evidence supports claims from traditional medicine that eugenol exerts beneficial effects on human health. These effects are mainly associated with antioxidant and anti-inflammatory activities. Eugenol has also shown excellent antimicrobial activity in studies, being active against fungi and a wide range of gram-negative and gram-positive bacteria. The aim of this review is to analyze scientific data from the main published studies describing the antibacterial and antifungal activities of eugenol targeting different kind of microorganisms, such as those responsible for human infectious diseases, diseases of the oral cavity, and food-borne pathogens. This article also reports the effects of eugenol on multi-drug resistant microorganisms. On the basis of this collected data, eugenol represents a very interesting bioactive compound with broad spectrum antimicrobial activity against both planktonic and sessile cells belonging to food-decaying microorganisms and human pathogens.
Carvacrol promotes angiogenic paracrine potential and endothelial differentiation of human mesenchymal stem cells at low concentrations.

PubMed

Matluobi, Danial; Araghi, Atefeh; Maragheh, Behnaz Faramarzian Azimi; Rezabakhsh, Aysa; Soltani, Sina; Khaksar, Majid; Siavashi, Vahid; Feyzi, Adel; Bagheri, Hesam Saghaei; Rahbarghazi, Reza; Montazersaheb, Soheila

2018-01-01

Phenolic monoterpene compound, named Carvacrol, has been found to exert different biological outcomes. It has been accepted that the angiogenic activity of human mesenchymal stem cells was crucial in the pursuit of appropriate regeneration. In the current experiment, we investigated the contribution of Carvacrol on the angiogenic behavior of primary human mesenchymal stem cells. Mesenchymal stem cells were exposed to Carvacrol in a dose ranging from 25 to 200μM for 48h. We measured cell survival rate by MTT assay and migration rate by a scratch test. The oxidative status was monitored by measuring SOD, GPx activity. The endothelial differentiation was studied by evaluating the level of VE-cadherin and vWF by real-time PCR and ELISA analyses. The content of VEGF and tubulogenesis behavior was monitored in vitro. We also conducted Matrigel plug in vivo CAM assay to assess the angiogenic potential of conditioned media from human mesenchymal stem cells after exposure to Carvacrol. Carvacrol was able to increase mesenchymal stem cell survival and migration rate (p<0.05). An increased activity of SOD was obtained while GPx activity unchanged or reduced. We confirmed the endothelial differentiation of stem cells by detecting vWF and VE-cadherin expression (p<0.05). The VEGF expression was increased and mesenchymal stem cells conditioned media improved angiogenesis tube formation in vitro (p<0.05). Moreover, histological analysis revealed an enhanced microvascular density at the site of Matrigel plug in CAM assay. Our data shed lights on the possibility of a Carvacrol to induce angiogenesis in human mesenchymal stem cells by modulating cell differentiation and paracrine angiogenic response. Copyright © 2017 Elsevier Inc. All rights reserved.
Thymol nanoemulsions incorporated in quinoa protein/chitosan edible films; antifungal effect in cherry tomatoes.

PubMed

Robledo, Nancy; Vera, Paola; López, Luis; Yazdani-Pedram, Mehrdad; Tapia, Cristian; Abugoch, Lilian

2018-04-25

Thymol nanoemulsions were produced by spontaneous emulsification, ultrasound, and a combination of both methods. The best result in terms of size and polydispersion was spontaneous emulsification where thymol was efficiently encapsulated, the nanoemulsions inhibited Botrytis cinerea at 110 ppm of thymol. A 10% dilution of this nanoemulsion in water was used to prepare quinoa-chitosan films. The film microstructure was porous and heterogeneous. The tensile strength of the film was significantly lower but its mean elongation at break was similar to that of the control film. The water vapour permeability was similar to that of the control film. The effect of nanoemulsion-thymol-quinoa protein/chitosan coating on mould growth in inoculated cherry tomatoes was evaluated. Compared with control samples (tomatoes without coating and those coated with quinoa protein/chitosan), tomatoes with this coating and inoculated with B. cinerea showed a significant decrease in fungal growth after 7 days at 5 °C. Copyright © 2017 Elsevier Ltd. All rights reserved.
Fabrication, characterization and antimicrobial activities of thymol-loaded zein nanoparticles stabilized by sodium caseinate-chitosan hydrochloride double layers.

PubMed

Zhang, Yaqiong; Niu, Yuge; Luo, Yangchao; Ge, Mei; Yang, Tian; Yu, Liangli Lucy; Wang, Qin

2014-01-01

Thymol-loaded zein nanoparticles stabilized with sodium caseinate (SC) and chitosan hydrochloride (CHC) were prepared and characterized. The SC stabilized nanoparticles had well-defined size range and negatively charged surface. Due to the presence of SC, the stabilized zein nanoparticles showed a shift of isoelectric point from 6.18 to 5.05, and had a desirable redispersibility in water at neutral pH after lyophilization. Coating with CHC onto the SC stabilized zein nanoparticles resulted in increased particle size, reversal of zeta potential value from negative to positive, and improved encapsulation efficiency. Both thymol-loaded zein nanoparticles and SC stabilized zein nanoparticles had a spherical shape and smooth surface, while the surfaces of CHC-SC stabilized zein nanoparticles seemed rough and had some clumps. Encapsulated thymol was more effective in suppressing gram-positive bacterium than un-encapsulated thymol for a longer time period. Copyright © 2013 Elsevier Ltd. All rights reserved.
Genotoxicity evaluation of carvacrol in rats using a combined micronucleus and comet assay.

PubMed

Llana-Ruiz-Cabello, María; Maisanaba, Sara; Puerto, María; Prieto, Ana I; Pichardo, Silvia; Moyano, Rosario; González-Pérez, José A; Cameán, Ana M

2016-12-01

Genotoxic data of substances which could be incorporated into food packaging are required by the European Food Safety Authority. Due to its antioxidant and antibacterial properties carvacrol is one of these compounds. This work aims to study for the first time the in vivo genotoxic effects produced in rats orally exposed to 81, 256 or 810 mg cavacrol/kg body weight (bw) at 0, 24 and 45 h. A combination of the micronucleus assay (OECD 474) in bone marrow and the standard (OECD 489) and enzyme-modified comet assay was used to determine the genotoxicity on cells isolated from stomach and liver of exposed animals. In addition, a histopathological study was performed on the assayed tissues, and also in the lungs due to the volatility of carvacrol. Direct analytical pyrolysis was used to search for carvacrol in viscera and to ensure that the compound reaches stomach and liver cells. Results from MN-comet assay revealed that carvacrol (81-810 mg/kg bw) did not induce in vivo genotoxicity or oxidative DNA damage in any of the tissues investigated. Moreover, no histopathological changes were observed. Altogether, these results suggest lack of genotoxicity of carvacrol and therefore its good profile for its potential application as food preservative. Copyright Â© 2016 Elsevier Ltd. All rights reserved.
Biosynthesis of estragole and methyl-eugenol in sweet basil (Ocimum basilicum L). Developmental and chemotypic association of allylphenol O-methyltransferase activities.

PubMed

Lewinsohn, E; Ziv-Raz, I; Dudai, N; Tadmor, Y; Lastochkin, E; Larkov, O; Chaimovitsh, D; Ravid, U; Putievsky, E; Pichersky, E; Shoham, Y

2000-12-07

Sweet basil (Ocimum basilicum L., Lamiaceae) is a common herb, used for culinary and medicinal purposes. The essential oils of different sweet basil chemotypes contain various proportions of the allyl phenol derivatives estragole (methyl chavicol), eugenol, and methyl eugenol, as well as the monoterpene alcohol linalool. To monitor the developmental regulation of estragole biosynthesis in sweet basil, an enzymatic assay for S-adenosyl-L-methionine (SAM):chavicol O-methyltransferase activity was developed. Young leaves display high levels of chavicol O-methyltransferase activity, but the activity was negligible in older leaves, indicating that the O-methylation of chavicol primarily occurs early during leaf development. The O-methyltransferase activities detected in different sweet basil genotypes differed in their substrate specificities towards the methyl acceptor substrate. In the high-estragole-containing chemotype R3, the O-methyltransferase activity was highly specific for chavicol, while eugenol was virtually not O-methylated. In contrast, chemotype 147/97, that contains equal levels of estragole and methyl eugenol, displayed O-methyltransferase activities that accepted both chavicol and eugenol as substrates, generating estragole and methyl eugenol, respectively. Chemotype SW that contains high levels of eugenol, but lacks both estragole and methyl eugenol, had apparently no allylphenol dependent O-methyltransferase activities. These results indicate the presence of at least two types of allylphenol-specific O-methyltransferase activities in sweet basil chemotypes, one highly specific for chavicol; and a different one that can accept eugenol as a substrate. The relative availability and substrate specificities of these O-methyltransferase activities biochemically rationalizes the variation in the composition of the essential oils of these chemotypes.
Inhibitory effects of eugenol on putative nociceptive response in spinal cord preparation isolated from neonatal rats.

PubMed

Yagura, Saki; Onimaru, Hiroshi; Kanzaki, Koji; Izumizaki, Masahiko

2018-06-01

Eugenol is contained in several plants including clove and is thought to exert an analgesic effect. It has been suggested that the slow ventral root potential induced by ipsilateral dorsal root stimulation in the isolated (typically lumbar) spinal cord of newborn rats reflects the nociceptive response, and this in vitro experimental model is useful to assess the actions of analgesics. To further elucidate neuronal mechanisms of eugenol-induced analgesia, we examined the effects of extracellularly applied eugenol on the nociceptive spinal reflex response. To evaluate the effects of eugenol on putative nociceptive responses, the ipsilateral fifth lumbar (L5) dorsal root was stimulated using a glass suction electrode, and the induced reflex responses were recorded from the L5 and twelfth thoracic (Th12) ventral roots in spinal cord preparations (Th10-L5) from newborn rats (postnatal day 0-3). We found that eugenol (0.25-1.0 mM) caused dose-dependent attenuation of the reflex response and also depressed spontaneous ventral root activity. We also found that the slow ventral root potential was further divided into two components: initial and late components. A lower concentration of eugenol selectively depressed the late component. The inhibitory effects by 1.0 mM eugenol were not reversed by 10 µM capsazepine (TRPV1 antagonist) or 40 µM HC-030031 (TRPA1 antagonist). The depressive effect of eugenol on the reflex response was also confirmed by optical recordings using voltage-sensitive dye. Our report provides additional evidence on the basic neuronal mechanisms of eugenol to support its clinical use as a potential analgesic treatment.
The ameliorative effect of thymol against hydrocortisone-induced hepatic oxidative stress injury in adult male rats.

PubMed

Aboelwafa, Hanaa R; Yousef, Hany N

2015-08-01

The aim of the present study was to investigate whether hydrocortisone induces oxidative stress in hepatocytes and to evaluate the possible ameliorative effect of thymol against such hepatic injury. Twenty-four adult male rats were divided into control, thymol, hydrocortisone, and hydrocortisone+thymol groups. The 4 groups were treated daily for 15 days. Hydrocortisone significantly induced oxidative stress in the liver tissues, marked by increased serum levels of alanine transaminase (ALT), aspartate transaminase (AST), total oxidative capacity (TOC), and tumor necrosis factor-alpha (TNF-α) accompanied by marked decline of serum levels of total protein, albumin, and total antioxidant capacity (TAC). Also, marked elevation in the levels of the thiobarbituric acid reactive substances (TBARS) and TNF-α, beside significant decrease in the level of glutathione (GSH) in hepatic tissues were recorded. These biochemical alterations were accompanied by histopathological changes marked by destruction of the normal hepatic architecture, in addition to ultrastructural alterations represented by degenerative features covering almost all the cytoplasmic organelles of the hepatocytes. Supplementation of hydrocortisone-treated rats with thymol reversed most of the biochemical, histological, and ultrastructural alterations. The results of our study confirm that thymol has strong ameliorative effect against hydrocortisone-induced oxidative stress injury in hepatic tissues.
Sensitive voltammetric determination of thymol in essential oil of Carum copticum seeds using boron-doped diamond electrode.

PubMed

Stanković, Dalibor M

2015-10-01

Essential oil of Carum copticum seeds, obtained from a local shop, was extracted and content of thymol was analyzed using square-wave voltammetry at boron-doped diamond electrode. The effect of various parameters, such as pH of supporting electrolyte and square-wave voltammetric parameters (modulation amplitude and frequency), was examined. In Britton-Robinson buffer solution (pH 4), thymol provided a single and oval-shaped irreversible oxidation peak at +1.13 V versus silver/silver chloride potassium electrode (3M). Under optimal experimental conditions, a plot of peak height against concentration of thymol was found to be linear over the range of 4 to 100μM consisting of two linear ranges: from 4 to 20μM (R(2)=0.9964) and from 20 to 100μM (R(2)=0.9993). The effect of potential interferences such as p-cymene and γ-terpinene (major components in essential oil of C. copticum seeds) was evaluated. Thus, the proposed method displays a sufficient selectivity toward thymol with a detection limit of 3.9μM, and it was successfully applied for the determination of thymol in essential oil of C. copticum seeds. The Prussian blue method was used for validation of the proposed electroanalytical method. Copyright © 2015 Elsevier Inc. All rights reserved.
Potential preventive effect of carvacrol against diethylnitrosamine-induced hepatocellular carcinoma in rats.

PubMed

Jayakumar, Subramaniyan; Madankumar, Arumugam; Asokkumar, Selvamani; Raghunandhakumar, Subramanian; Gokula dhas, Krishnan; Kamaraj, Sattu; Divya, Michael Georget Josephine; Devaki, Thiruvengadam

2012-01-01

Antioxidants are one of the key players in tumorigenesis, several natural and synthetic antioxidants were shown to have anticancer effects. The aim of the present study is to divulge the chemopreventive nature of carvacrol during diethylnitrosamine (DEN)-induced liver cancer in male wistar albino rats. Administration of DEN to rats resulted in increased relative liver weight and serum marker enzymes aspartate transaminase (AST), alanine transaminase (ALT), alkaline phosphatase (ALP), lactate dehydrogenase (LDH), and gamma glutamyl transpeptidase (γGT). The levels of lipid peroxides elevated (in both serum and tissue) with subsequent decrease in the final body weight and tissue antioxidants like superoxide dismutase (SOD), catalase (CAT), reduced glutathione (GSH), glutathione peroxidase (GPx), and glutathione reductase (GR). Carvacrol supplementation (15 mg/kg body weight) significantly attenuated these alterations, thereby showing potent anticancer effect in liver cancer. Histological observations and transmission electron microscopy studies were also carried out, which added supports to the chemopreventive action of the carvacrol against DEN-induction during liver cancer progression. These findings suggest that carvacrol prevents lipid peroxidation, hepatic cell damage, and protects the antioxidant system in DEN-induced hepatocellular carcinogenesis.
Anti-genotoxicity of trans-anethole and eugenol in mice.

PubMed

Abraham, S K

2001-05-01

The naturally occurring flavouring agents trans-anethole and eugenol were evaluated for antigenotoxic effects in mice. The test doses of trans-anethole (40-400 mg/kg body weight) and eugenol (50-500 mg/kg weight) were administered by gavage 2 and 20 h before the genotoxins were injected intraperitoneally. Anti-genotoxic effects were assessed in the mouse bone marrow micronucleus test. Pretreatment with trans-anethole and eugenol led to significant antigenotoxic effects against cyclophosphamide (CPH), procarbazine (PCB), N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) and urethane (URE). In addition, trans-anethole inhibited the genotoxicity of ethyl methane sulfonate (EMS). Both trans-anethole and eugenol exerted dose-related antigenotoxic effects against PCB and URE. There was no significant increase in genotoxicity when trans-anethole (40-400 mg/kg body weight) and eugenol (50-500 mg/kg body weight) were administered alone.
Antioxidant and antimicrobial activities of clove bud essential oil and eugenol nanoparticles in alcohol-free microemulsion.

PubMed

Hamed, Said Fatouh; Sadek, Zainab; Edris, Amr

2012-01-01

Clove bud essential oil (CEO) and its major individual phenolic constituent eugenol were formulated as nanoparticles in water-based microemulsion systems. The oil titration method was used to incorporate different amounts of the oil and eugenol in the micellar solution of Tween-20. The Antioxidant and antimicrobial activities were evaluated using the DPPH* free radical scavenging assay and the agar disc dilution method, respectively. Results showed that microemulsion improved the evaluated activities of CEO and eugenol compared with the crude counterparts. Individual eugenol microemulsion was more effective than CEO microemulsion which contained only 61.7% eugenol among its constituents. The results of this study could have potential applications in water-based disinfectants, preservation and flavoring of food and in personal hygiene products. It may also have promising applications in the nutraceutical and functional beverage field.
Chemical characterization and antifungal activity of Origanum vulgare, Thymus vulgaris essential oils and carvacrol against Malassezia furfur.

PubMed

Vinciguerra, Vittorio; Rojas, Florencia; Tedesco, Viviana; Giusiano, Gustavo; Angiolella, Letizia

2018-05-04

The composition of the essential oils (EOs) of O. vulgare L. EO and T. vulgaris EO, were analyzed by GC and GC-MS. Antifungal activities of the EOs and its main component, carvacrol, were evaluated against 27 clinical isolates of Malassezia furfur. Minimum inhibitory concentrations (MICs) were measured according to the broth microdilution protocols by Clinical and Laboratory Standards Institute (CLSI) modified for Malassezia spp. EOs and carvacrol showed low MIC values ranged 450-900 μg/ml against M. furfur. No differences in EOs antifungal activity were observed in sensitive to resistant fluconazole isolates. The antifungal activity obtained showed O. vulgare EO, T. vulgaris EO and carvacrol, their compound, as potential antimicrobial agents against M. furfur, yeast associated with human mycoses.
Chemical composition and biological evaluation of the volatile constituents from the aerial parts of Nephrolepis exaltata (L.) and Nephrolepis cordifolia (L.) C. Presl grown in Egypt.

PubMed

El-Tantawy, Mona E; Shams, Manal M; Afifi, Manal S

2016-01-01

The essential oil from the aerial parts of Nephrolepis exaltata and Nephrolepis cordifolia obtained by hydro-distillation were analyzed by gas chromatography/ mass spectrometry. The essential oils exhibited potential antibacterial and antifungal activities against a majority of the selected microorganisms. NEA oil showed promising cytotoxicity in breast, colon and lung carcinoma cells. The results presented indicate that NEA oil could be useful alternative for the treatment of dermatophytosis. Comparative investigation of hydro-distilled volatile constituents from aerial parts (A) of Nephrolepis exaltata (NE) and Nephrolepis cordifolia (NC) (Family Nephrolepidaceae) was carried out. Gas chromatography/mass spectrometry revealed that oils differ in composition and percentages of components. Oxygenated compounds were dominant in NEA and NCA. 2,4-Hexadien-1-ol (16.1%), nonanal (14.4%), β-Ionone (6.7%) and thymol (2.7%) were predominant in NEA. β-Ionone (8.0%), eugenol (7.2%) and anethol (4.6%) were the main constituents in NCA. Volatile samples were screened for their antibacterial and antifungal activities using agar diffusion method and minimum inhibitory concentrations. The cytotoxic activity was evaluated using viability assay in breast (MCF-7), colon (HCT-116) and lung carcinoma (A-549) cells by the MTT assay. The results revealed that NEA oil exhibited potential antimicrobial activity against most of the tested organisms and showed promising cytotoxicity.
Influence of Environmental Factors on Essential Oil Variability in Origanum compactum Benth. Growing Wild in Morocco.

PubMed

Aboukhalid, Kaoutar; Al Faiz, Chaouki; Douaik, Ahmed; Bakha, Mohamed; Kursa, Karolina; Agacka-Mołdoch, Monika; Machon, Nathalie; Tomi, Félix; Lamiri, Abdeslam

2017-09-01

The present study aimed to evaluate the influence of environmental factors on essential oils (EOs) composition of Origanum compactum populations sampled all over the distribution area of the species in Morocco, and to determine the extent of the chemical profiles throughout the geographical distribution of the species. The chemical compositions were submitted to canonical correlation analysis and canonical discriminant analysis that indicated a significant relationship between oil components and some environmental factors. According to their chemical composition and edapho-climatic characteristics, two major groups of populations were differentiated. The first group was composed of samples growing in regions with humid climate, clayey, sandy, and alkaline soils. These samples showed high thymol, α-terpineol, linalool, and carvacryl methyl oxide content. The second group consisted of plants belonging to semi-arid climate, and growing at high altitudes and silty soils. These samples were characterized by high carvacrol, α-thujene, α-terpinene, and myrcene content. However, populations exposed to sub-humid climate, appeared less homogeneous and belong mainly either to the first or second group. A significant correlation between some edaphic factors (pH, K 2 O content, soil texture) and the EOs yield of O. compactum plants was evidenced. In spite of the correlation obtained for the oil composition with edapho-climatic factors and the variance explained by the environmental data set, the observed EO diversity might be also genetically determined. © 2017 Wiley-VHCA AG, Zurich, Switzerland.
Antimicrobial profile of essential oils extracted from wild versus cultivated Origanum ehrenberjii against enteric bacteria.

PubMed

Barbour, Elie K; Dankar, Samar K; Shaib, Houssam A; Kumosani, Taha; Azhar, Esam; Masaudi, Saad; Iyer, Archana; Harakeh, Steve

2014-10-15

The role of Origanum ehrenberjii against bacteria that cause enteric diseases is well known. Salmonella and Enterococcus cause high rates of enteric infections around the world. The aim of this study was to extract essential oils from cultivated and naturally growing O. ehrenberjii, compare the chemical profiles of the extracts and estimate their antimicrobial efficacy against enteric pathogens. Sixteen compounds were recovered consistently from essential oils extracted from O. ehrenberjii of wild and cultivated origin. The chemical profiles were determined using GC-MS. Safety of the essential oils was determined by observing mortality of chicks after intramuscular administration of the oils. The antimicrobial efficacy of the oils against the enteric pathogens was determined by the Kirby-Bauer Single Disk Diffusion assay. The levels of thymol, carvacrol, para cymene and γ-terpinene were significantly different in the two oils. A significant difference in in vitro antimicrobial activity of the two oils against Salmonella enterica serovar Typhimurium was observed. Intramuscular administration of the two oils in one day-old chicks resulted in significant differences in mortality of 60% vs. 5% (p < 0.05) for wild and cultivated herbs respectively, reflecting the higher safety of the cultivated herb due to the differences in the levels of certain active ingredients. The chemical profile of essential oil of wild vs. cultivated O. ehrenberjii differ significantly at compound level, suggesting the reason for their significant difference in efficacy against Salmonella enterica serovar Typhimurium, and also significant differences in the toxicity of the two oils.
The antimicrobial effect of oregano essential oil, nisin and their combination against Salmonella Enteritidis in minced sheep meat during refrigerated storage.

PubMed

Govaris, A; Solomakos, N; Pexara, A; Chatzopoulou, P S

2010-02-28

The antimicrobial effect of oregano essential oil (EO) at 0.6 or 0.9%, nisin at 500 or 1000 IU/g, and their combination against Salmonella Enteritidis was studied in minced sheep meat during storage at 4 degrees or 10 degrees C for 12 days. Sensory evaluation showed that the addition of oregano EO at 0.6 or 0.9% in minced sheep meat was organoleptically acceptable, and attribute scores were higher for the EO at 0.6 than 0.9%. According to compositional analysis of the oregano EO, the phenols carvacrol (80.15%) and thymol (4.82%) were the predominant components. Treatment of minced sheep meat with nisin at 500 or 1000 IU/g, proved insufficient to act against S. Enteritidis. The combination of the oregano EO at 0.6% with nisin at 500 IU/g showed stronger antimicrobial activity against S. Enteritidis than the oregano EO at 0.6% but lower than the combination with nisin at 1000 IU/g, which in turn was lower than that of the oregano EO at 0.9%. In its turn, oregano EO at 0.9% showed lower antimicrobial activity than its combinations with nisin at 500 or 1000 IU/g, which showed a bactericidal effect against the pathogen. The inhibition percentages of all treatments against S. Enteritidis at 10 degrees C were higher than those at 4 degrees C. (c) 2009 Elsevier B.V. All rights reserved.

Ziziphora clinopodioides Essential Oil and Nisin as Potential Antimicrobial Agents against Escherichia coli O157:H7 in Doogh (Iranian Yoghurt Drink)

PubMed Central

Shahbazi, Yasser

2015-01-01

The aim of the present study was to evaluate the effects of Ziziphora clinopodioides essential oil (0.1 and 0.2%) and nisin (250 and 500 IU/mL) separately and in combination on survival of Escherichia coli O157:H7 inoculated in Doogh (Iranian yoghurt drink) during storage under refrigerated temperature (4 ± 1°C) for 9 days. Viability of Lactobacillus casei at different concentrations of Z. clinopodioides essential oil (0.1 and 0.2%) in Doogh was also examined. The major components were carvacrol (64.22%), thymol (19.22%), γ-terpinene (4.63%), and p-cymene (4.86%). There was no significant difference (p > 0.05) between samples treated with nisin and those of untreated samples. Samples treated with both concentrations of the essential oil (0.1 and 0.2%) showed populations of E. coli O157:H7 significantly (p < 0.05) lower than those of untreated samples. The essential oil of Z. clinopodioides in combination with nisin had a potential synergistic effect against E. coli O157:H7 in Doogh samples after 5 days. The count of L. casei was not inhibited by different concentrations of the Z. clinopodioides essential oil. It is concluded that the leaf essential oil of Z. clinopodioides in combination with nisin can be applied as alternative antimicrobial agents in Doogh to inhibit the growth of E. coli O157:H7. PMID:26783466
Optimized ultrasonic assisted extraction-dispersive liquid-liquid microextraction coupled with gas chromatography for determination of essential oil of Oliveria decumbens Vent.

PubMed

Sereshti, Hassan; Izadmanesh, Yahya; Samadi, Soheila

2011-07-22

Ultrasonic assisted extraction-dispersive liquid-liquid microextraction (UAE-DLLME) coupled with gas chromatography (GC) was applied for extraction and determination of essential oil constituents of the plant Oliveria decumbens Vent. Scanning electron microscopy (SEM) was used to see the effect of ultrasonic radiation on the extraction efficiency. By comparison with hydrodistillation, UAE-DLLME is fast, low cost, simple, efficient and consuming small amount of plant materials (∼1.0 g). The effects of various parameters such as temperature, ultrasonication time, volume of disperser and extraction solvents were investigated by a full factorial design to identify significant variables and their interactions. The results demonstrated that temperature and ultrasonication time had no considerable effect on the results. In the next step, a central composite design (CCD) was performed to obtain the optimum levels of significant parameters. The obtained optimal conditions were: 0.45 mL for disperser solvent (acetonitrile) and 94.84 μL for extraction solvent (chlorobenzene). The limits of detection (LODs), linear dynamic range and determination coefficients (R(2)) were 0.2-29 ng mL(-1), 1-2100 ng mL(-1) and 0.995-0.998, respectively. The main components of the essential oil were: thymol (47.06%), carvacrol (23.31%), gamma-terpinene (18.94%), p-cymene (8.71%), limonene (0.76%) and myristicin (0.63%). Copyright © 2011 Elsevier B.V. All rights reserved.
Essential Oils and Eugenols Inhibit Biofilm Formation and the Virulence of Escherichia coli O157:H7

PubMed Central

Kim, Yong-Guy; Lee, Jin-Hyung; Gwon, Giyeon; Kim, Soon-Il; Park, Jae Gyu; Lee, Jintae

2016-01-01

Enterohemorrhagic Escherichia coli O157:H7 (EHEC) has caused foodborne outbreaks worldwide and the bacterium forms antimicrobial-tolerant biofilms. We investigated the abilities of various plant essential oils and their components to inhibit biofilm formation by EHEC. Bay, clove, pimento berry oils and their major common constituent eugenol at 0.005% (v/v) were found to markedly inhibit EHEC biofilm formation without affecting planktonic cell growth. In addition, three other eugenol derivatives isoeugenol, 2-methoxy-4-propylphenol, and 4-ethylguaiacol had antibiofilm activity, indicating that the C-1 hydroxyl unit, the C-2 methoxy unit, and C-4 alkyl or alkane chain on the benzene ring of eugenol play important roles in antibiofilm activity. Interestingly, these essential oils and eugenol did not inhibit biofilm formation by three laboratory E. coli K-12 strains that reduced curli fimbriae production. Transcriptional analysis showed that eugenol down-regulated 17 of 28 genes analysed, including curli genes (csgABDFG), type I fimbriae genes (fimCDH) and ler-controlled toxin genes (espD, escJ, escR, and tir), which are required for biofilm formation and the attachment and effacement phenotype. In addition, biocompatible poly(lactic-co-glycolic acid) coatings containing clove oil or eugenol exhibited efficient biofilm inhibition on solid surfaces. In a Caenorhabditis elegans nematode model, clove oil and eugenol attenuated the virulence of EHEC. PMID:27808174
Antibacterial and antifungal activities of thymol: A brief review of the literature.

PubMed

Marchese, Anna; Orhan, Ilkay Erdogan; Daglia, Maria; Barbieri, Ramona; Di Lorenzo, Arianna; Nabavi, Seyed Fazel; Gortzi, Olga; Izadi, Morteza; Nabavi, Seyed Mohammad

2016-11-01

Thymol (2-isopropyl-5-methylphenol) is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family (Thymus, Ocimum, Origanum, and Monarda genera), and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae, and Apiaceae families. These essential oils are used in the food industry for their flavouring and preservative properties, in commercial mosquito repellent formulations for their natural repellent effect, in aromatherapy, and in traditional medicine for the treatment of headaches, coughs, and diarrhea. Many different activities of thymol such as antioxidant, anti-inflammatory, local anaesthetic, antinociceptive, cicatrizing, antiseptic, and especially antibacterial and antifungal properties have been shown. This review aims to critically evaluate the available literature regarding the antibacterial and antifungal effects of thymol. Copyright © 2016 Elsevier Ltd. All rights reserved.
Comparative inhibitory effects of magnolol, honokiol, eugenol and bis-eugenol on cyclooxygenase-2 expression and nuclear factor-kappa B activation in RAW264.7 macrophage-like cells stimulated with fimbriae of Porphyromonas gingivalis.

PubMed

Murakami, Yukio; Kawata, Akifumi; Seki, Yuya; Koh, Teho; Yuhara, Kenji; Maruyama, Takehisa; Machino, Mamoru; Ito, Shigeru; Kadoma, Yoshinori; Fujisawa, Seiichiro

2012-01-01

The anti-inflammatory activity of magnolol and related compounds is currently a focus of interest. In the present study, the inhibitory effects of these compounds on cyclooxygenase (COX-2) expression and nuclear factor-kappa B (NF-κB) activation were investigated in RAW264.7 macrophage-like cells stimulated with the fimbriae of Porphyromonas gingivalis, an oral anaerobe. The cytotoxicity of magnolol, honokiol, eugenol and bis-eugenol against RAW264.7 cells was determined using a cell counting kit (CCK-8). The regulatory effect of these compounds on the expression of COX-2 mRNA, stimulated by exposure to the fimbriae was investigated by real-time polymerase chain reaction (PCR). NF-κB activation was evaluated by enzyme-linked immunosorbent assay (ELISA)-like microwell colorimetric transcription factor activity assay (Trans-AM) and western blot analysis. The radical-scavenging activity was determined using the induction period method in the methyl methacrylate-azobisisobutyronitrile (AIBN) polymerization system under nearly anaerobic conditions. The phenolic bond dissociation enthalpy (BDE) and orbital energy were calculated at the density functional theory (DFT) B3LYP/6-31G* level. The cytotoxicity against RAW264.7 cells declined in the order bis-eugenol>eugenol> honokiol>magnolol, whereas the radical-scavenging activity declined in the order honokiol, bis-eugenol>magnolol> eugenol. Magnolol and honokiol significantly inhibited the fimbria-induced expression of COX-2 at non-cytotoxic concentrations. Both the fimbria-stimulated binding of NF-κB to its consensus sequence and phosphorylation-dependent proteolysis of inhibitor κB-α were markedly inhibited by magnilol and honokiol, whereas eugenol and bis-eugenol did not inhibit COX-2 expression and NF-κB activation. Magnolol and honokiol possessed a high electronegativity (χ) value. Magnolol and honokiol exhibit antioxidative activity, low cytotoxicity, and anti-inflammatory activity. These compounds may be capable of preventing chronic inflammatory diseases induced by oral bacteria.
Influence of Temporary Cements on the Bond Strength of Self-Adhesive Cement to the Metal Coronal Substrate.

PubMed

Peixoto, Raniel Fernandes; De Aguiar, Caio Rocha; Jacob, Eduardo Santana; Macedo, Ana Paula; De Mattos, Maria da Gloria Chiarello; Antunes, Rossana Pereira de Almeida

2015-01-01

This research evaluated the influence of temporary cements (eugenol-containing [EC] or eugenol-free [EF]) on the tensile strength of Ni-Cr copings fixed with self-adhesive resin cement to the metal coronal substrate. Thirty-six temporary crowns were divided into 4 groups (n=9) according to the temporary cements: Provy, Dentsply (eugenol-containing), Temp Cem, Vigodent (eugenol-containing), RelyX Temp NE, 3M ESPE (eugenol-free) and Temp Bond NE, Kerr Corp (eugenol-free). After 24 h of temporary cementation, tensile strength tests were performed in a universal testing machine at a crosshead speed of 0.5 mm/min and 1 kN (100 kgf) load cell. Afterwards, the cast metal cores were cleaned by scraping with curettes and air jet. Thirty-six Ni-Cr copings were cemented to the cast metal cores with self-adhesive resin cement (RelyX U200, 3M ESPE). Tensile strength tests were performed again. In the temporary cementation, Temp Bond NE (12.91 ± 2.54) and Temp Cem (12.22 ± 2.96) presented the highest values of tensile strength and were statistically similar to each other (p>0.05). Statistically significant difference (p<0.05) was observed only between Provy (164.44 ± 31.23) and Temp Bond NE (88.48 ± 21.83) after cementation of Ni-Cr copings with self-adhesive resin cement. In addition, Temp Cem (120.68 ± 48.27) and RelyX Temp NE (103.04 ± 26.09) showed intermediate tensile strength values. In conclusion, the Provy eugenol-containing temporary cement was associated with the highest bond strength among the resin cements when Ni-Cr copings were cemented to cast metal cores. However, the eugenol cannot be considered a determining factor in increased bond strength, since the other tested cements (1 eugenol-containing and 2 eugenol-free) were similar.
Organic Heat Stabilizers for Polyvinyl Chloride (PVC): A Synergistic Behavior of Eugenol and Uracil Derivative

NASA Astrophysics Data System (ADS)

Asawakosinchai, Aran; Jubsilp, Chanchira; Mora, Phattarin; Rimdusit, Sarawut

2017-10-01

Recycling ability, mechanical, and thermal properties of PVC stabilized with organic heat stabilizers, i.e., uracil (DAU) and eugenol were investigated to substitute PVCs stabilized with commercial lead, Ca/Zn, and organic-based stabilizer for PVC pipe production. PVC stabilized with the DAU and the eugenol can be processable at 30 °C lower than that of the PVC stabilized with commercial heat stabilizers. The most remarkable short-term thermal stability belonged to the PVC stabilized with the DAU, and its original color can be maintained at least up to 3 processing cycles. Synergistic behavior in thermal stability of the PVC mixed with DAU and eugenol at mass ratios of 1.5:1.5 was observed. Mechanical properties of DAU- and eugenol-stabilized PVC were higher than the samples with other heat stabilizers. Glass transition temperature of the PVC stabilized with all heat stabilizers was determined to be 99 °C with the exception of the value of 89 °C for eugenol-stabilized PVC. Therefore, the DAU and the eugenol showed high potential to be used as an organic heat stabilizer for PVC because of their non-toxic and good heat resistance properties.
Eugenol and methyl eugenol chemotypes of essential oil of species Ocimum gratissimum L. and Ocimum campechianum Mill. from Colombia.

PubMed

Pino Benitez, Nayive; Meléndez León, Erika M; Stashenko, Elena E

2009-10-01

Essential oils chemical constituents of leaves of O. gratissimum and O. campechianum of the Lamiaceae family, collected in Chocó of northwest Colombian, were obtained by microwave-assisted hydrodistillation and analyzed by gas chromatography coupled with mass spectrometry. A total of 33 and 37 compounds were identified in the essential oil of O. gratissimum and O. campechianum, respectively. O. gratissimum's main essential oils were eugenol (43.2%), 1,8-cineole (12.8%) and beta-selinene (9.0%); in the O. campechianum essential oil, the main components were methyl eugenol (12.0%), germacrene D (10.1%), and eugenol (9.0%). Main distribution of compounds in these essential oils are 25.0% monoterpenes hydrocarbons, 15.0% monoterpenes oxygenated, 35.0% sesquiterpenes hydrocarbons, 7.5% other oxygenated components for O. gratissimum, 33.9% sesquiterpenes hydrocarbons, and 10.7% their respective oxygenated derivates; for O. campechianum, the distribution was 10.7% monoterpenes hydrocarbons and 7.1% their respective oxygenated derivates and 3.6% phenylpropanes. According to the essential oils chemical composition of Ocimum gratissimum and O. campechianum, they are classified as eugenol and methyl eugenol chemotype, respectively.
Effect of Eugenol against Streptococcus agalactiae and Synergistic Interaction with Biologically Produced Silver Nanoparticles

PubMed Central

Perugini Biasi-Garbin, Renata; Saori Otaguiri, Eliane; Fernandes da Silva, Mayara; Belotto Morguette, Ana Elisa; Armando Contreras Lancheros, César; Kian, Danielle; Perugini, Márcia Regina Eches; Durán, Nelson; Nakamura, Celso Vataru; Yamauchi, Lucy Megumi; Yamada-Ogatta, Sueli Fumie

2015-01-01

Streptococcus agalactiae (group B streptococci (GBS)) is an important infections agent in newborns associated with maternal vaginal colonization. Intrapartum antibiotic prophylaxis in GBS-colonized pregnant women has led to a significant reduction in the incidence of early neonatal infection in various geographic regions. However, this strategy may lead to resistance selecting among GBS, indicating the need for new alternatives to prevent bacterial transmission and even to treat GBS infections. This study reported for the first time the effect of eugenol on GBS isolated from colonized women, alone and in combination with silver nanoparticles produced by Fusarium oxysporum (AgNPbio). Eugenol showed a bactericidal effect against planktonic cells of all GBS strains, and this effect appeared to be time-dependent as judged by the time-kill curves and viability analysis. Combination of eugenol with AgNPbio resulted in a strong synergistic activity, significantly reducing the minimum inhibitory concentration values of both compounds. Scanning and transmission electron microscopy revealed fragmented cells and changes in bacterial morphology after incubation with eugenol. In addition, eugenol inhibited the viability of sessile cells during biofilm formation and in mature biofilms. These results indicate the potential of eugenol as an alternative for controlling GBS infections. PMID:25945115
Effects of the naturally occurring alkenylbenzenes eugenol and trans-anethole on drug-metabolizing enzymes in the rat liver.

PubMed

Rompelberg, C J; Verhagen, H; van Bladeren, P J

1993-09-01

In order to study the effects of trans-anethole and eugenol on drug-metabolizing enzyme activities in vivo, male Wistar rats were treated by gavage with trans-anethole (125 or 250 mg/kg body weight) or eugenol (250, 500 or 1000 mg/kg body weight) daily for 10 days. In liver microsomes and cytosol various phase-I and phase-II biotransformation enzyme activities were determined. No effect on total cytochrome P-450 content in liver microsomes from rats treated with eugenol or trans-anethole was observed. Administration of 1000 mg eugenol/kg body weight, but not the lower doses, significantly increased cytochrome P-450-dependent 7-ethoxy-resorufin O-deethylation (EROD) and 7-pentoxyresorufin O-depentylation (PROD); administration of trans-anethole (125 or 250 mg/kg body weight) did not alter EROD and PROD activities. In rat liver cytosol, UDP-glucuronyl transferase (GT) activity towards the substrate 4-chlorophenol was significantly increased in all treated rats, and activity towards 4-hydroxybiphenyl as substrate was significantly increased in rats treated with 250 mg trans-anethole/kg or with 500 or 1000 mg eugenol/kg. DT-diaphorase (DTD) activity was only significantly enhanced in the liver cytosol of rats treated with trans-anethole at 250 mg/kg body weight. Enhancement of cytosolic glutathione S-transferase (GST) activity towards 1-chloro-2,4-dinitrobenzene was found for all eugenol- and trans-anethole-treated rats. In addition, significantly increased levels of GST subunit 2 were measured by HPLC in the liver cytosol of rats treated with eugenol (500 or 1000 mg/kg body eight) or trans-anethole (250 mg/kg body weight). It is concluded that both eugenol and trans-anethole preferentially induced phase II biotransformation enzymes in rat liver in vivo.
Depletion of eugenol residues from the skin-on fillet tissue of rainbow trout exposed to 14C-labeled eugenol

USGS Publications Warehouse

Meinertz, Jeffery R.; Schreier, Theresa M.; Porcher, Scott T.; Smerud, Justin R.; Gaikowski, Mark P.

2014-01-01

The U.S. is lagging in access to an approved immediate-release sedative, i.e. a compound that can be safely and effectively used to sedate fish and has no withdrawal period. AQUI-S® 20E (10% active ingredient, eugenol) is under investigation as an immediate-release sedative for freshwater finfish. Because of its investigational status, data are needed to characterize the depletion, distribution, and identity of AQUI-S® 20E residues in fillet tissue. Rainbow trout (Oncorhynchus mykiss) were exposed to uniformly ring labeled 14C-eugenol at a nominal concentration of 10 mg/L for 60 min in 18 °C water. Fish (n = 6) were sampled immediately after the exposure (0 min) then at 30, 60, 120, and 240 min. Eugenol concentrations and characterization of 14C residues in the fillet tissue were determined by high pressure liquid chromatography and flow-through liquid scintillation counting techniques. Total 14C-residue burdens in fillet tissue were determined by tissue oxidation and static liquid scintillation counting techniques. Maximum eugenol and 14C-eugenol equivalent residue concentrations in the fillet tissue were measured immediately after the exposure (44.5 and 38.8 μg/g, respectively). Eugenol was the primary 14C-residue (> 90% of all 14C-residues) in extracts from fillet tissue taken from fish sampled immediately after the exposure (0 min) and from fish sampled at 30 and 60 min after the exposure. The depletion of 14C-eugenol residues from the fillet tissue was rapid (t1/2 = 26.25 min) after transferring the exposed fish to fresh flowing water.
Carvacrol Induces Heat Shock Protein 60 and Inhibits Synthesis of Flagellin in Escherichia coli O157:H7▿

PubMed Central

Burt, Sara A.; van der Zee, Ruurd; Koets, Ad P.; de Graaff, Anko M.; van Knapen, Frans; Gaastra, Wim; Haagsman, Henk P.; Veldhuizen, Edwin J. A.

2007-01-01

The essential oils of oregano and thyme are active against a number of food-borne pathogens, such as Escherichia coli O157:H7. Carvacrol is one of the major antibacterial components of these oils, and p-cymene is thought to be its precursor in the plant. The effects of carvacrol and p-cymene on protein synthesis in E. coli O157:H7 ATCC 43895 cells were investigated. Bacteria were grown overnight in Mueller-Hinton broth with a sublethal concentration of carvacrol or p-cymene, and their protein compositions were analyzed by sodium dodecyl sulfate-polyacrylamide gel electrophoresis and confirmed by Western blotting. The presence of 1 mM carvacrol during overnight incubation caused E. coli O157:H7 to produce significant amounts of heat shock protein 60 (HSP60) (GroEL) (P < 0.05) and inhibited the synthesis of flagellin highly significantly (P < 0.001), causing cells to be aflagellate and therefore nonmotile. The amounts of HSP70 (DnaK) were not significantly affected. p-Cymene at 1 mM or 10 mM did not induce HSP60 or HSP70 in significant amounts and did not have a significant effect on flagellar synthesis. Neither carvacrol (0.3, 0.5, 0.8, or 1 mM) nor p-cymene (0.3, 0.5, or 0.8 mM) treatment of cells in the mid-exponential growth phase induced significant amounts of HSP60 or HSP70 within 3 h, although numerical increases of HSP60 were observed. Motility decreased with increasing concentrations of both compounds, but existing flagella were not shed. This study is the first to demonstrate that essential oil components induce HSP60 in bacteria and that overnight incubation with carvacrol prevents the development of flagella in E. coli O157:H7. PMID:17526792
Milk and plasma disposition of thymol following intramammary administration of a phytoceutical mastitis treatment.

PubMed

McPhee, C S; Anderson, K L; Yeatts, J L; Mason, S E; Barlow, B M; Baynes, R E

2011-04-01

Despite the recent growth of the organic dairy industry, organic producers and veterinarians have limited information when choosing mastitis treatments for animals in organic dairy production. Organic producers commonly administer homeopathic or other plant-based products without having research evaluating the efficacy of these products and using estimated or no withholding times to treat mastitis and other health problems in their herds. In this pilot study, we attempted to identify several active ingredients of Phyto-Mast (Penn Dutch Cow Care, Narvon, PA), a plant-based mastitis treatment used on organic dairy farms, and to quantify the product residue in milk and plasma after intramammary administration. We developed an assay to quantify thymol (one of the active ingredients in Phyto-Mast) in milk and plasma using gas chromatography and mass spectrometry (GC-MS). Thymol is a volatile aromatic compound with antiinflammatory properties. As a model for dairy cows, 5 healthy, lactating alpine dairy goats were given 5 mL of Phyto-Mast per udder half. For 10 d following treatment, we analyzed blood and milk samples for thymol residues using GC-MS. The GC-MS assay was very sensitive for thymol detection, to a concentration of 0.01 μg/mL in plasma. Using thymol as a marker, Phyto-Mast was detectable and quantifiable in plasma beginning with the 15-min posttreatment sample, but was no longer detectable in the 4-h posttreatment sample. Thymol residues were only detected in the 12-h posttreatment milk sample. An inflammatory response was not evident in the udder following phytoceutical administration. Although this study provides information about the elimination of thymol, the product contains several other active chemicals, which may have different pharmacokinetic behaviors. Further analysis and additional study animals will help to determine a milk withholding time for Phyto-Mast. Given the recent growth of the organic dairy industry, understanding the pharmacokinetics of therapeutics used in organic production and developing accurate withholding recommendations will help to ensure milk safety. Copyright © 2011 American Dairy Science Association. Published by Elsevier Inc. All rights reserved.
Can Ocimum basilicum L. and Ocimum tenuiflorum L. in vitro culture be a potential source of secondary metabolites?

PubMed

Bhuvaneshwari, Karuppiah; Gokulanathan, Ananda; Jayanthi, Malayandi; Govindasamy, Vaithiyanathan; Milella, Luigi; Lee, Sungyoung; Yang, Deok Chun; Girija, Shanmugam

2016-03-01

In this study Ocimum basilicum L. (OB) and Ocimum tenuiflorum L. (OT) in vitro culture standardisation for increasing eugenol distribution, in comparison to their respective field grown parts was carried out. Eugenol was quantified using an optimised HPLC method and its relation with the total phenolic content (TPC) was measured. In vitro grown leaves and somatic embryos, of both OB and OT were found to contain similar quantities of eugenol (85μg/g approximately), higher than OB and OT field-grown leaves (30.2μg/g and 25.1μg/g respectively). It was also determined that in vitro grown leaves were richer in TPC than the field-grown intact organs. Results demonstrated the prominence of in vitro cultures for eugenol extraction. This study underlines that important food flavouring metabolites (e.g. vanillin, vanillic acids) might be produced, via the eugenol pathway, in Ocimum species that may be a good potential source of eugenol. Copyright © 2015. Published by Elsevier Ltd.
Effect of periodontal dressings on human gingiva fibroblasts in vitro

DOE Office of Scientific and Technical Information (OSTI.GOV)

Eber, R.M.; Shuler, C.F.; Buchanan, W.

1989-08-01

In vitro cytotoxicity studies of periodontal dressings have not generally produced a result consistent with in vivo observations. These prior in vitro studies have not used human intraoral cell lines. We tested the effects of two eugenol containing and two non-eugenol periodontal dressings on cultured human gingival fibroblasts (HGF) (ATCC No. 1292). Replicate HGF cultures grown in microtiter plates were exposed to stock, 1:4 and 1:16 dilutions of extracts made from each of the four periodontal dressings. The HGF cultures were pulse labelled with tritiated thymidine (3HTdR) after 24, 48, and 72 hours. Incorporations of the labelled thymidine were measuredmore » using liquid scintillation counting and expressed as counts per minute. The results showed that undiluted extracts from all four periodontal dressings totally inhibited 3HTdR uptake (P less than 0.05). The 1:4 dilution of eugenol dressings inhibited 3HTdR uptake significantly more than non-eugenol dressings (P less than 0.05). Interestingly, at 72 hours the 1:16 dilution of the non-eugenol dressings caused significantly increased 3HTdR uptake which was not observed with the eugenol dressings. The present results suggest that the use of a human fibroblastic cell line for testing the effects of periodontal dressings may provide information about the relative biological effects of these dressings. Using this cell line, we have found that eugenol dressings inhibit fibroblast proliferation to a greater extent than non-eugenol dressings.« less
Synergies of carvacrol and 1,8-cineole to inhibit bacteria associated with minimally processed vegetables.

PubMed

de Sousa, Jossana Pereira; de Azerêdo, Geíza Alves; de Araújo Torres, Rayanne; da Silva Vasconcelos, Margarida Angélica; da Conceição, Maria Lúcia; de Souza, Evandro Leite

2012-03-15

This study assessed the occurrence of an enhancing inhibitory effect of the combined application of carvacrol and 1,8-cineole against bacteria associated with minimally processed vegetables using the determination of Fractional Inhibitory Concentration (FIC) index, time-kill assay in vegetable broth and application in vegetable matrices. Their effects, individually and in combination, on the sensory characteristics of the vegetables were also determined. Carvacrol and 1,8-cineole displayed Minimum Inhibitory Concentration (MIC) in a range of 0.6-2.5 and 5-20 μL/mL, respectively, against the organisms studied. FIC indices of the combined application of the compounds were 0.25 against Listeria monocytogenes, Aeromonas hydrophila and Pseudomonas fluorescens, suggesting a synergic interaction. Application of carvacrol and 1,8-cineole alone (MIC) or in a mixture (1/8 MIC+1/8 MIC or 1/4 MIC+1/4 MIC) in vegetable broth caused a significant decrease (p<0.05) in bacterial count over 24h. Mixtures of carvacrol and 1,8-cineole reduced (p<0.05) the inocula of all bacteria in vegetable broth and in experimentally inoculated fresh-cut vegetables. A similar efficacy was observed in the reduction of naturally occurring microorganisms in vegetables. Sensory evaluation revealed that the scores of the most-evaluated attributes fell between "like slightly" and "neither like nor dislike." The combination of carvacrol and 1,8-cineole at sub-inhibitory concentrations could constitute an interesting approach to sanitizing minimally processed vegetables. Copyright © 2011 Elsevier B.V. All rights reserved.
Development of a polydimethylsiloxane-thymol/nitroprusside composite based sensor involving thymol derivatization for ammonium monitoring in water samples.

PubMed

Prieto-Blanco, M C; Jornet-Martínez, N; Moliner-Martínez, Y; Molins-Legua, C; Herráez-Hernández, R; Verdú Andrés, J; Campins-Falcó, P

2015-01-15

This report describes a polydimethylsiloxane (PDMS)-thymol/nitroprusside delivery composite sensor for direct monitoring of ammonium in environmental water samples. The sensor is based on a PDMS support that contains the Berthelot's reaction reagents. To prepare the PDMS-thymol/nitroprusside composite discs, thymol and nitroprusside have been encapsulated in the PDMS matrix, forming a reagent release support which significantly simplifies the analytical measurements, since it avoids the need to prepare derivatizing reagents and sample handling is reduced to the sampling step. When, the PDMS-thymol/nitroprusside composite was introduced in water samples spontaneous release of the chromophore and catalyst was produced, and the derivatization reaction took place to form the indothymol blue. Thus, qualitative analysis of NH4(+) could be carried out by visual inspection, but also, it can be quantified by measuring the absorbance at 690 nm. These portable devices provided good sensitivity (LOD<0.4 mg L(-1)) and reproducibility (RSD <10%) for the rapid detection of ammonium. The PDMS-NH4(+) sensor has been successfully applied to determine ammonium in water samples and in the aqueous extracts of particulate matter PM10 samples. Moreover, the reliability of the method for qualitative analysis has been demonstrated. Finally, the advantages of the PDMS-NH4(+) sensor have been examined by comparing some analytical and complementary characteristics with the properties of well-established ammonium determination methods. Copyright © 2014 Elsevier B.V. All rights reserved.
Inhibitory effects of anethole and eugenol on the growth and toxin production of Aspergillus parasiticus.

PubMed

Karapinar, M

1990-05-01

The antifungal and antiaflatoxigenic activity of anethole and eugenol which are active components of commonly used spices was studied against two strains of Aspergillus parasiticus. Anethole, up to concentration of 400 micrograms/ml where complete inhibition was observed, delayed growth and reduced mycelial weight but it showed a stimulative effect on the toxin production of both strains. At a concentration of 300 micrograms/ml, eugenol inhibited the growth of both strains; levels of eugenol below 200 micrograms/ml enhanced production of aflatoxin particularly by A. parasiticus NRRL 299.
Eugenol reduces the expression of virulence-related exoproteins in Staphylococcus aureus.

PubMed

Qiu, Jiazhang; Feng, Haihua; Lu, Jing; Xiang, Hua; Wang, Dacheng; Dong, Jing; Wang, Jianfeng; Wang, Xiaoliang; Liu, Juxiong; Deng, Xuming

2010-09-01

Eugenol, an essential oil component in plants, has been demonstrated to possess activity against both gram-positive and gram-negative bacteria. This study examined the influence that subinhibitory concentrations of eugenol may have on the expression of the major exotoxins produced by Staphylococcus aureus. The results from a tumor necrosis factor (TNF) release assay and a hemolysin assay indicated that S. aureus cultured with graded subinhibitory concentrations of eugenol (16 to 128 microg/ml) dose dependently decreased the TNF-inducing and hemolytic activities of culture supernatants. Western blot analysis showed that eugenol significantly reduced the production of staphylococcal enterotoxin A (SEA), SEB, and toxic shock syndrome toxin 1 (the key exotoxins to induce TNF release), as well as the expression of alpha-hemolysin (the major hemolysin to cause hemolysis). In addition, this suppression was also evaluated at the transcriptional level via real-time reverse transcription (RT)-PCR analysis. The transcriptional analysis indicated that 128 microg/ml of eugenol remarkably repressed the transcription of the S. aureus sea, seb, tst, and hla genes. According to these results, eugenol has the potential to be rationally applied on food products as a novel food antimicrobial agent both to inhibit the growth of bacteria and to suppress the production of exotoxins by S. aureus.
Thymol Elicits HCT-116 Colorectal Carcinoma Cell Death Through Induction of Oxidative Stress.

PubMed

Chauhan, Anil Kumar; Bahuguna, Ashutosh; Paul, Souren; Kang, Sun Chul

2018-02-07

Colon cancer is one of the most deadly and common carcinomas occurring worldwide and there have been many attempts to treat this cancer. The present work was designed in order to evaluate thymol as a potent drug against colon cancer. Cytotoxicity of thymol at different concentrations was evaluated against a human colon carcinoma cell line (HCT-116 cells). Fluorescent staining was carried out to evaluate the level of ROS as well as mitochondrial and DNA fragmentation and immunoblot analysis were performed to confirm apoptosis and mitoptosis. Results of the study demonstrated that thymol efficiently created an oxidative stress environment inside HCT-116 cells, a colorectal carcinoma cell line, through induction of ROS production along with intense damage to DNA and mitochondria, as observed through Hoechst and rhodamine 123 staining, respectively. Moreover, expression of PARP-1, p-JNK, cytochrome-C and caspase-3 proteins was up-regulated, suggesting HCT-116 cells underwent mitoptotic cell death. Therefore, thymol could be used as a potent drug against colon cancer due to its lower toxicity and prevalence in natural medicinal plants. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Phase behavior, microstructural transition, antimicrobial and antioxidant activities of a water-dilutable thymol microemulsion.

PubMed

Deng, Lingli; Taxipalati, Maierhaba; Sun, Ping; Que, Fei; Zhang, Hui

2015-12-01

Pseudo ternary phase diagrams were constructed to assess the dilutability of thymol microemulsions using non-ionic (Tween 80), cationic (CTAB), and anionic (SDS) surfactants. We successfully constructed a thymol U-type microemulsion system using Tween 80 as surfactant and studied the microstructural transition along the dilution line at a 90/10 surfactant/oil mass ratio, with thymol and ethanol (3:1, w/w) as the oil phase. Differential scanning calorimetry analysis suggested that the microemulsions gradually inverted from the water-in-oil (W/O) (0-20% water) to the bicontinuous (25-35% water), and finally to the oil-in-water (O/W) (40-90% water) microstructures upon dilution, in good agreement with the conductivity measurements, while the rheological results indicated the collapse of rod-like micelles followed by formation of spherical micelles in the O/W region. The activities of the U-type thymol microemulsions are structural dependent. The antimicrobial activity against Escherichia coli and Staphylococcus aureus decreased when the microemulsions transformed from W/O to bicontinuous and O/W structures, while the DPPH scavenging activity increased. Copyright © 2015 Elsevier B.V. All rights reserved.
TRPV3 expression and vasodilator function in isolated uterine radial arteries from non-pregnant and pregnant rats.

PubMed

Murphy, Timothy V; Kanagarajah, Arjna; Toemoe, Sianne; Bertrand, Paul P; Grayson, T Hilton; Britton, Fiona C; Leader, Leo; Senadheera, Sevvandi; Sandow, Shaun L

2016-08-01

This study investigated the expression and function of transient receptor potential vanilloid type-3 ion channels (TRPV3) in uterine radial arteries isolated from non-pregnant and twenty-day pregnant rats. Immunohistochemistry (IHC) suggested TRPV3 is primarily localized to the smooth muscle in arteries from both non-pregnant and pregnant rats. IHC using C' targeted antibody, and qPCR of TRPV3 mRNA, suggested pregnancy increased arterial TRPV3 expression. The TRPV3 activator carvacrol caused endothelium-independent dilation of phenylephrine-constricted radial arteries, with no difference between vessels from non-pregnant and pregnant animals. Carvacrol-induced dilation was reduced by the TRPV3-blockers isopentenyl pyrophosphate and ruthenium red, but not by the TRPA1 or TRPV4 inhibitors HC-030031 or HC-067047, respectively. In radial arteries from non-pregnant rats only, inhibition of NOS and sGC, or PKG, enhanced carvacrol-mediated vasodilation. Carvacrol-induced dilation of arteries from both non-pregnant and pregnant rats was prevented by the IKCa blocker TRAM-34. TRPV3 caused an endothelium-independent, IKCa-mediated dilation of the uterine radial artery. NO-PKG-mediated modulation of TRPV3 activity is lost in pregnancy, but this did not alter the response to carvacrol. Copyright © 2016 Elsevier Inc. All rights reserved.
Anti-cholinesterase activity of the standardized extract of Syzygium aromaticum L.

PubMed

Dalai, Manoj K; Bhadra, Santanu; Chaudhary, Sushil K; Bandyopadhyay, Arun; Mukherjee, Pulok K

2014-04-01

Clove (Syzygium aromaticum) is a well-known culinary spice with strong aroma; contains a high amount of oil known as clove oil. The major phyto-constituent of the clove oil is eugenol. Clove and its oil possess various medicinal uses in indigenous medicine as an antiseptic, anti-oxidant, analgesic and neuroprotective properties. Thus, it draws much attention among researchers from pharmaceutical, food and cosmetic industries. The aim of the present study was to determine the anti-cholinesterase activity of the methanol extract of clove, its oil and eugenol. In vitro anti-cholinesterase activity of S. aromaticum was performed by a thin layer chromatography bio autography, 96 well micro titer plate and kinetic methods. Reverse phase high performance liquid chromatography (RP-HPLC) analysis was carried out to identify the biomarker compound eugenol in clove oil. Acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition study revealed that eugenol possess better inhibition of the enzymes than extract and oil. Clove extract, its oil and eugenol showed better inhibition of AChE than BChE. Polyphenolic compound eugenol was detected through RP-HPLC analysis. The content of eugenol in essential oil was found to be 0.5 μg/ml. Kinetic analysis of the cholinesterase inhibition study of the extract; clove oil and eugenol have shown that they possess mixed type of inhibition for AChE and non-competitive type of inhibition for BChE. These results might be useful in explaining the effect of clove as anti-cholinesterase agent for the management of cognitive ailments like Alzheimer's disease.
Scavenger Activity Evaluation of the Clove Bud Essential Oil (Eugenia caryophyllus) and Eugenol Derivatives Employing ABTS+• Decolorization

PubMed Central

Merchán Arenas, Diego R.; Acevedo, Amner Muñoz; Vargas Méndez, Leonor Y.; Kouznetsov, Vladimir V.

2011-01-01

The essential oil (EO) of clove bud dried fruits from Eugenia caryophyllus was obtained by a conventional hydrodistillation process in an excellent yield (11.7 %). Its chemical composition was analyzed by GC-MS, identifying eugenol as a main constituent (60.5%). Four eugenol-like molecules, γ-diisoeugenol, hydroxymethyleugenol, dihydroeugenol and 1,3-dioxanylphenol, were synthesized using eugenol or isoeugenol as initial precursors under green chemistry protocols. To evaluate the possible antioxidant capacity of eugenol compounds including the clove bud EO, the Trolox® Equivalent Antioxidant Capacity value, obtained by the ABTS+• radical-cation discoloration method, was employed. The methodology was performed in a UV-Vis reader of 96-well microplates (dilution methodology), using well-known antioxidant agents (BHA, BHT and vitamin E) as reference compounds. It was found that the prepared eugenol derivatives had a more potent free radical scavenger activity than the reference compounds. In particular, the most active molecules, γ-diisoeugenol and 1,3-dioxanylphenol, were ca. 3-fold more potent than vitamin E. PMID:22145105
Scavenger Activity Evaluation of the Clove Bud Essential Oil (Eugenia caryophyllus) and Eugenol Derivatives Employing ABTS Decolorization.

PubMed

Merchán Arenas, Diego R; Acevedo, Amner Muñoz; Vargas Méndez, Leonor Y; Kouznetsov, Vladimir V

2011-01-01

The essential oil (EO) of clove bud dried fruits from Eugenia caryophyllus was obtained by a conventional hydrodistillation process in an excellent yield (11.7 %). Its chemical composition was analyzed by GC-MS, identifying eugenol as a main constituent (60.5%). Four eugenol-like molecules, γ-diisoeugenol, hydroxymethyleugenol, dihydroeugenol and 1,3-dioxanylphenol, were synthesized using eugenol or isoeugenol as initial precursors under green chemistry protocols. To evaluate the possible antioxidant capacity of eugenol compounds including the clove bud EO, the Trolox® Equivalent Antioxidant Capacity value, obtained by the ABTS(+•) radical-cation discoloration method, was employed. The methodology was performed in a UV-Vis reader of 96-well microplates (dilution methodology), using well-known antioxidant agents (BHA, BHT and vitamin E) as reference compounds. It was found that the prepared eugenol derivatives had a more potent free radical scavenger activity than the reference compounds. In particular, the most active molecules, γ-diisoeugenol and 1,3-dioxanylphenol, were ca. 3-fold more potent than vitamin E.
Thymol, a dietary monoterpene phenol abrogates mitochondrial dysfunction in β-adrenergic agonist induced myocardial infarcted rats by inhibiting oxidative stress.

PubMed

Nagoor Meeran, M F; Jagadeesh, G S; Selvaraj, P

2016-01-25

Mitochondrial dysfunction has been suggested to be one of the important pathological events in isoproterenol (ISO), a synthetic catecholamine and β-adrenergic agonist induced myocardial infarction (MI). In this context, we have evaluated the impact of thymol against ISO induced oxidative stress and calcium uniporter malfunction involved in the pathology of mitochondrial dysfunction in rats. Male albino Wistar rats were pre and co-treated with thymol (7.5 mg/kg body weight) daily for 7 days. Isoproterenol (100 mg/kg body weight) was subcutaneously injected into rats on 6th and 7th day to induce MI. To explore the extent of cardiac mitochondrial damage, the activities/levels of cardiac marker enzymes, mitochondrial lipid peroxidation products, antioxidants, lipids, calcium, adenosine triphosphate and multi marker enzymes were evaluated. Isoproterenol induced myocardial infarcted rats showed a significant increase in the activities of cardiac diagnostic markers, heart mitochondrial lipid peroxidation, lipids, calcium, and a significant decrease in the activities/levels of heart mitochondrial superoxide dismutase, catalase, glutathione peroxidase, reduced glutathione, isocitrate, malate, α-ketoglutarate and NADH-dehydrogenases, cytochrome-C-oxidase, and adenosine triphosphate. Thymol pre and co-treatment showed near normalized effects on all the biochemical parameters studied. Transmission electron microscopic findings and mitochondrial swelling studies confirmed our biochemical findings. The in vitro study also revealed the potent free-radical scavenging activity of thymol. Thus, thymol attenuates the involvement of ISO against oxidative stress and calcium uniporter malfunction associated with mitochondrial dysfunction in rats. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.
Preparation of mucoadhesive oral patches containing tetracycline hydrochloride and carvacrol for treatment of local mouth bacterial infections and candidiasis.

PubMed

Obaidat, Rana M; Bader, Ammar; Al-Rajab, Wafa; Abu Sheikha, Ghassan; Obaidat, Aiman A

2011-01-01

The specific aim of this work was to prepare mucoadhesive patches containing tetracycline hydrochloride and carvacrol in an attempt to develop a novel oral drug delivery system for the treatment of mouth infections. The bilayered patches were prepared using ethyl cellulose as a backing layer and carbopol 934 as a matrix mucoadhesive layer. Patches were prepared with different loading amounts of tetracycline hydrochloride and carvacrol. The antimicrobial activity was assessed for the prepared patches using the disc-diffusion method against the yeast Candida albicans and five bacterial strains, including Pseudomonas aeruginosa, Escherichia coli, Bacillus cereus, Staphylococcus aureus, and Bacillus bronchispti. In this work, we highlighted the possibility of occurrence of a synergistic action between carvacrol and tetracycline. The best formulation was selected based on microbiological tests, drug release, ex-vivo mucoadhesive performance, and swelling index. Physical characteristics of the selected formulations were determined. These included pH, patch thickness, weight uniformity, content uniformity, folding endurance, and patch stability.
Carvacrol exhibits anti-oxidant and anti-inflammatory effects against 1, 2-dimethyl hydrazine plus dextran sodium sulfate induced inflammation associated carcinogenicity in the colon of Fischer 344 rats.

PubMed

Arigesavan, Kaninathan; Sudhandiran, Ganapasam

2015-05-29

Chronic inflammation is one of the remarkable etiologic factors for various human ailments including cancer. The well known hypothesis is that persistent inflammation in colon can increase the risk of colorectal cancer (CRC). In this study, a pharmacological evaluation of carvacrol, a phenolic monoterpene constituent of essential oils produced from aromatic plant Oreganum vulgarea sp. on colitis associated colon cancer (CACC) induced by 1,2 Dimethylhydrazine (DMH) and dextran sodium sulfate (DSS) in male Fischer 344 rat model was studied. F344 rats were given three subcutaneous injections of DMH (40 mg/kg body wt) in the first week and were given free access to drinking water containing 1% DSS for the next one week followed by 7-14 days of water as three cycles. Carvacrol was administrated before and after tumor induction at a concentration of 50 mg/kg body weight (o.p). Carvacrol treated groups promotes the endogenous antioxidant system and suppress the inflammation in DMH/DSS induced animals. An increased antioxidant status and restoration of histological lesions in the inflamed colonic mucosa was observed in carvacrol treated rats. This effect was confirmed biochemically by reducing free-radical accumulation and suppressing expression of pro-inflammatory mediators. In this study, Carvacrol significantly increased the anti-oxidant enzymes such as superoxide dismutase (SOD), catalase (CAT) glutathione (GSH) levels and reduced lipid peroxides (LPO), myeloperoxidase (MPO) and nitric oxide (NO) as compared to DMH/DSS induced rats. These dramatic changes facilitate the suppression of pro-inflammatory mediators such as inducible nitric oxide synthase (iNOS), and interleukin-1 beta (IL-1β) in CACC induced rats. Taken together, these findings suggest that Carvacrol may play a beneficial role in DMH/DSS induced experimental rat model and serve as an excellent dietary antioxidant as well as anti-inflammatory agent. It may represent novel therapeutic interventions against colon cancer triggered by chronic inflammation. Copyright © 2015 Elsevier Inc. All rights reserved.
Heat stability of carvacrol and trans-cinnamaldehyde during commercial manufacturing temperatures in chicken feed

USDA-ARS?s Scientific Manuscript database

With increasing consumer demand for natural, antibiotic free poultry products, the use of plant-derived antimicrobials (PDAs) as effective antimicrobial feed additives has gained significant attention. Among the various PDAs, carvacrol (CR) from oregano and trans-cinnamaldehyde (TC) from cinnamon ba...
Time-dependent antibacterial effects of Aloe vera and Zataria multiflora plant essential oils compared to calcium hydroxide in teeth infected with Enterococcus faecalis.

PubMed

Abbaszadegan, Abbas; Sahebi, Safoora; Gholami, Ahmad; Delroba, Alireza; Kiani, Amin; Iraji, Aida; Abbott, Paul Vincent

2016-02-01

In the present in vitro study, we investigated the time-related antimicrobial efficacy of Aloe vera and Zataria multiflora (Z. multiflora) plant essential oils compared to calcium hydroxide ([Ca[OH]2 ) to eliminate Enterococcus faecalis (E. faecalis) from root canals. A new strain of E. faecalis (Enterococcus spp. AGH04) was isolated from a previously root-filled tooth with persistent apical periodontitis. The 16S rRNA sequence was analyzed and deposited in GeneBank under accession number KF465681. A total of 108 extracted human single-rooted teeth were contaminated with this bacterial strain and treated with Aloe vera essential oil, Z. multiflora essential oil, and Ca(OH)2 for 1, 7, and 14 days. Gas chromatography-mass spectrometry (GC-MS) was used to determine the chemical composition of the oils. The percentage reduction from initial c.f.u./mL counts were calculated and analyzed. Carvacrol, thymol, and linalool were the main constituents of both essential oils. The c.f.u./mL count reductions significantly increased for all three medicaments when the contact time was extended. A statistically-significant difference was observed between the medicaments after 1 and 7 days, but there was no significant difference after 14 days. Both medicinal herbs showed equal antimicrobial efficiency against E. faecalis, comparable to Ca(OH)2 for the prolonged contact time of 14 days. © 2014 Wiley Publishing Asia Pty Ltd.
Inhibitory effect of Zataria multiflora Boiss. essential oil, alone and in combination with monolaurin, on Listeria monocytogenes

PubMed Central

Raeisi, Mojtaba; Tajik, Hossein; Razavi Rohani, Seyed Mehdi; Tepe, Bektas; Kiani, Hossein; Khoshbakht, Rahem; Shirzad Aski, Hesamaddin; Tadrisi, Hamed

2016-01-01

Listeria monocytogenes is one of the major causes of infections in developing countries. In this study, chemical composition and anti-listerial effect of the essential oil of Zataria multiflora Boiss. alone and in combination with monolaurin were evaluated at different pH values (5, 6, and 7) and temperatures (5 ˚C and 30 ˚C). Chemical composition of Zataria multiflora Boiss. essential oil was evaluated by gas chromatography-mass spectrometry (GC-MS) analysis. Minimum inhibitory concentration (MIC) of the essential oil and monolaurin were determined using microbroth dilution method and the interactions of essential oil and monolaurin were determined by the evaluation of fractional inhibitory concentrations (FIC) index. Carvacrol (63.20%) and thymol (15.10%) were found as the main components of the essential oil. The MIC values of the oil and monolaurin at pH 7 and 30 ˚C were measured as 312.50 µg mL-1 and 125.00 µg mL-1, respectively. Combination of monolaurin and Z. multiflora essential oil were found to act synergistically (FIC index < 0.5) against L. monocytogenes under different pH and temperature conditions. Decrease in the pH and temperature values have increased the anti-listerial activity of monolaurin and the essential oil. The lowest MIC value of monolaurin and essential oil was observed at pH 5 and 5 ˚C. According to our results, the oil alone or in combination with monolaurin at low pH and temperature conditions showed a promising inhibitory effect on L. monocytogenes. PMID:27226881
Essential oils of medicinal plants from the central andes of Argentina: chemical composition, and antifungal, antibacterial, and insect-repellent activities.

PubMed

Lima, Beatriz; López, Sandra; Luna, Lorena; Agüero, María B; Aragón, Liliana; Tapia, Alejandro; Zacchino, Susana; López, María L; Zygadlo, Julio; Feresin, Gabriela E

2011-05-01

The antifungal, antibacterial, and insect-repellent activities of the essential oils (EOs) of Acantholippia seriphioides, Artemisia mendozana, Gymnophyton polycephalum, Satureja parvifolia, Tagetes mendocina, and Lippia integrifolia, collected in the Central Andes area, province of San Juan, Argentina, were investigated. The dermatophytes Microsporum gypseum, Trichophyton mentagrophytes, and T. rubrum were inhibited by the EOs of G. polycephalum, L. integrifolia, and S. parvifolia, with minimum inhibitory concentrations (MICs) between 31.2 and 1000 μg/ml. Moreover, all EOs presented moderate activity against the bacteria tested, and the L. integrifolia and G. polycephalum EOs showed excellent repellent properties against Triatoma infestans, the Chagas disease vector, with repellency values between 60 and 100%. The A. seriphioides, G. polycephalum, and L. integrifolia EOs, obtained by hydrodistillation, were characterized by GC-FID and GC/MS analyses. The highest number of components (40) was identified in L. integrifolia EO, which, along with that of A. seriphioides, contained important amounts of oxygenated monoterpenes (44.35 and 29.72%, resp.). Thymol (27.61%) and carvacrol (13.24%) were the main components of A. seriphioides EO, and borneol, lippifoli-1(6)-en-5-one, and terpinen-4-ol (>8.5%) were the principal compounds of L. integrifolia EO. These results support the idea that oxygenated monoterpenes are the bioactive fractions of the EOs. Finally, the study shows that these Andean species might be used to treat superficial fungal infections and to improve the local Chagas disease situation by vector-control. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.
Inhibitory effect of Zataria multiflora Boiss. essential oil, alone and in combination with monolaurin, on Listeria monocytogenes.

PubMed

Raeisi, Mojtaba; Tajik, Hossein; Razavi Rohani, Seyed Mehdi; Tepe, Bektas; Kiani, Hossein; Khoshbakht, Rahem; Shirzad Aski, Hesamaddin; Tadrisi, Hamed

2016-01-01

Listeria monocytogenes is one of the major causes of infections in developing countries. In this study, chemical composition and anti-listerial effect of the essential oil of Zataria multiflora Boiss. alone and in combination with monolaurin were evaluated at different pH values (5, 6, and 7) and temperatures (5 ˚C and 30 ˚C). Chemical composition of Zataria multiflora Boiss. essential oil was evaluated by gas chromatography-mass spectrometry (GC-MS) analysis. Minimum inhibitory concentration (MIC) of the essential oil and monolaurin were determined using microbroth dilution method and the interactions of essential oil and monolaurin were determined by the evaluation of fractional inhibitory concentrations (FIC) index. Carvacrol (63.20%) and thymol (15.10%) were found as the main components of the essential oil. The MIC values of the oil and monolaurin at pH 7 and 30 ˚C were measured as 312.50 µg mL(-1) and 125.00 µg mL(-1), respectively. Combination of monolaurin and Z. multiflora essential oil were found to act synergistically (FIC index < 0.5) against L. monocytogenes under different pH and temperature conditions. Decrease in the pH and temperature values have increased the anti-listerial activity of monolaurin and the essential oil. The lowest MIC value of monolaurin and essential oil was observed at pH 5 and 5 ˚C. According to our results, the oil alone or in combination with monolaurin at low pH and temperature conditions showed a promising inhibitory effect on L. monocytogenes.
The SOS Chromotest applied for screening plant antigenotoxic agents against ultraviolet radiation.

PubMed

Fuentes, J L; García Forero, A; Quintero Ruiz, N; Prada Medina, C A; Rey Castellanos, N; Franco Niño, D A; Contreras García, D A; Córdoba Campo, Y; Stashenko, E E

2017-09-13

In this work, we investigated the usefulness of the SOS Chromotest for screening plant antigenotoxic agents against ultraviolet radiation (UV). Fifty Colombian plant extracts obtained by supercritical fluid (CO 2 ) extraction, twelve plant extract constituents (apigenin, carvacrol, β-caryophyllene, 1,8-cineole, citral, p-cymene, geraniol, naringenin, pinocembrin, quercetin, squalene, and thymol) and five standard antioxidant and/or photoprotective agents (curcumin, epigallocatechin gallate, resveratrol, α-tocopherol, and Trolox®) were evaluated for their genotoxicity and antigenotoxicity against UV using the SOS Chromotest. None of the plant extracts, constituents or agents were genotoxic in the SOS Chromotest at tested concentrations. Based on the minimal extract concentration that significantly inhibited UV-genotoxicity (CIG), five plant extracts were antigenotoxic against UV as follows: Baccharis nítida (16 μg mL -1 ) = Solanum crotonifolium (16 μg mL -1 ) > Hyptis suaveolens (31 μg mL -1 ) = Persea caerulea (31 μg mL -1 ) > Lippia origanoides (62 μg mL -1 ). Based on CIG values, the flavonoid compounds showed the highest antigenotoxic potential as follows: apigenin (7 μM) > pinocembrin (15 μM) > quercetin (26 μM) > naringenin (38 μM) > epigallocatechin gallate (108 μM) > resveratrol (642 μM). UV-genotoxicity inhibition with epigallocatechin gallate, naringenin and resveratrol was related to its capability for inhibiting protein synthesis. A correlation analysis between compound antigenotoxicity estimates and antioxidant activity evaluated by the oxygen radical absorbance capacity (ORAC) assay showed that these activities were not related. The usefulness of the SOS Chromotest for bioprospecting of plant antigenotoxic agents against UV was discussed.
Antimicrobial Effect of Lippia sidoides and Thymol on Enterococcus faecalis Biofilm of the Bacterium Isolated from Root Canals

PubMed Central

Veras, H. N. H.; Rodrigues, F. F. G.; Botelho, M. A.; Menezes, I. R. A.; Coutinho, H. D. M.; da Costa, J. G. M.

2014-01-01

The species Lippia sidoides Cham. (Verbenaceae) is utilized in popular medicine as a local antiseptic on the skin and mucosal tissues. Enterococcus faecalis is the bacterium isolated from root canals of teeth with persistent periapical lesions and has the ability to form biofilm, where it is responsible for the failure of endodontic treatments. Essential oil of L. sidoides (EOLS) and its major component, thymol, were evaluated for reducing the CFU in biofilms of E. faecalis in vitro. The essential oil was obtained by hydrodistillation and examined with respect to the chemical composition, by gas chromatography-mass spectrometry (GC-MS). The GC-MS analysis has led to the identification of thymol (84.9%) and p-cymene (5.33%). EOLS and thymol reduced CFU in biofilms of E. faecalis in vitro (time of maturation, 72 h), with an exposure time of 30 and 60 min at concentrations of 2.5 and 10%. There was no statistical difference in effect between EOLS and thymol, demonstrating that this phenolic monoterpene was the possible compound responsible for the antimicrobial activity of EOLS. This study provides a basis for the possible utilization of EOLS as an adjuvant in the treatment of root canals that show colonization by E. faecalis. PMID:24683344
Citral and eugenol modulate DNA damage and pro-inflammatory mediator genes in murine peritoneal macrophages.

PubMed

Porto, Marilia de Paula; da Silva, Glenda Nicioli; Luperini, Bruno Cesar Ottoboni; Bachiega, Tatiana Fernanda; de Castro Marcondes, João Paulo; Sforcin, José Maurício; Salvadori, Daisy Maria Fávero

2014-11-01

Citral and eugenol have been broadly studied because of their anti-inflammatory, antioxidant and antiparasitic potentials. In this study, the effects of citral (25, 50 and 100 µg/mL) and eugenol (0.31, 0.62, 1.24 and 2.48 µg/mL) on the expression (RT-PCR) of the pro-inflammatory mediator genes NF-κB1, COX-2 and TNF-α were evaluated in mouse peritoneal macrophages with or without activation by a bacterial lipopolysaccharide (LPS). Additionally, the genotoxic potentials of two compounds and their capacities to modulate the DNA damage induced by doxorubicin (DXR) were investigated using the comet assay. The data revealed that neither citral nor eugenol changed COX-2, NF-κB1 or TNF-α expression in resting macrophages. However, in LPS-activated cells, citral induced the hypoexpression of COX-2 (100 µg/mL) and TNF-α (50 and 100 µg/mL). Hypoexpression of TNF-α was also detected after cellular exposure to eugenol at the highest concentration (2.48 µg/mL). Both compounds exhibited genotoxic potential (citral at 50 and 100 µg/mL and eugenol at all concentrations) but also showed chemopreventive effects, in various treatment protocols. Both citral and eugenol might modulate inflammatory processes and DXR-induced DNA damage, but the use of these compounds must be viewed with caution because they are also able to induce primary DNA lesions.
Clove and eugenol in noncytotoxic concentrations exert immunomodulatory/anti-inflammatory action on cytokine production by murine macrophages.

PubMed

Bachiega, Tatiana Fernanda; de Sousa, João Paulo Barreto; Bastos, Jairo Kenupp; Sforcin, José Maurício

2012-04-01

The extract and essential oil of clove (Syzygium aromaticum) are widely used because of their medicinal properties. Eugenol is the most important component of clove, showing several biological properties. Herein we have analysed the immunomodulatory/anti-inflammatory effect of clove and eugenol on cytokine production (interleukin (IL)-1β, IL-6 and IL-10) in vitro. Macrophages were incubated with clove or eugenol (5, 10, 25, 50 or 100µg/well) for 24h. Concentrations that inhibited the production of cytokines were used before or after incubation with lipopolysaccharide (LPS), to verify a preventive or therapeutic effect. Culture supernatants were harvested for measurement of cytokines by enzyme-linked immunosorbent assay. Clove (100µg/well) inhibited IL-1β, IL-6 and IL-10 production and exerted an efficient action either before or after LPS challenge for all cytokines. Eugenol did not affect IL-1β production but inhibited IL-6 and IL-10 production. The action of eugenol (50 or 100µg/well) on IL-6 production prevented efficiently effects of LPS either before or after its addition, whereas on IL-10 production it counteracted significantly LPS action when added after LPS incubation. Clove exerted immunomodulatory/anti-inflammatory effects by inhibiting LPS action. A possible mechanism of action probably involved the suppression of the nuclear factor-κB pathway by eugenol, since it was the major compound found in clove extract. © 2012 The Authors. JPP © 2012 Royal Pharmaceutical Society.
Blending lecithin and gelatin improves the formation of thymol nanodispersions.

PubMed

Xue, Jia; Zhong, Qixin

2014-04-02

Delivery systems of lipophilic antimicrobials such as thymol prepared with generally recognized-as-safe ingredients are needed to enhance the microbiological safety of low-acid (pH > 4.6) foods. Nanodispersions with particle diameters below 100 nm are particularly demanded because of the low turbidity and physical stability. In this study, thymol dispersions were prepared by gelatin and soy lecithin on an individual basis or in combination. Dispersions prepared with the lecithin-gelatin blend were translucent and stable at pH 5.0-8.0, contrasting with turbid and unstable dispersions when the emulsifiers were used individually. The synergistic surface activity of gelatin and lecithin was due to complex formation that effectively prevented particle size change due to coalescence and Ostwald ripening. Electrostatic interactions were observed to be the colloidal force responsible for preventing particle aggregation. The studied generally recognized-as-safe nanodispersions have great potential to deliver lipophilic antimicrobials such as thymol in low-acid foods to enhance food safety.
Effect of thymol in heating and recovery media on the isothermal and non-isothermal heat resistance of Bacillus spores.

PubMed

Esteban, Maria-Dolores; Conesa, Raquel; Huertas, Juan-Pablo; Palop, Alfredo

2015-06-01

Members of the genus Bacillus include important food-borne pathogen and spoilage microorganisms for food industry. Essential oils are natural products extracted from herbs and spices, which can be used as natural preservatives in many foods because of their antibacterial, antifungal, antioxidant and anti-carcinogenic properties. The aim of this research was to explore the effect of the addition of different concentrations of thymol to the heating and recovery media on the thermal resistance of spores of Bacillus cereus, Bacillus licheniformis and Bacillus subtilis at different temperatures. While the heat resistance was hardly reduced when thymol was present in the heating medium, the effect in the recovery medium was greater, reducing the D100 °C values down to one third for B. subtilis and B. cereus when 0.5 mM thymol was added. This effect was dose dependent and was also observed at other heating temperatures. Copyright © 2014 Elsevier Ltd. All rights reserved.
Pre-Release Consumption of Methyl Eugenol Increases the Mating Competitiveness of Sterile Males of the Oriental Fruit Fly, Bactrocera dorsalis, in Large Field Enclosures

PubMed Central

Shelly, Todd E.; Edu, James; McInnis, Donald

2010-01-01

The sterile insect technique may be implemented to control populations of the oriental fruit fly, Bactrocera dorsalis (Hendel) (Diptera: Tephritidae), when environmental concerns preclude widespread use of chemical attractants or toxicants. The goal of the present study was to evaluate whether the mating competitiveness of sterile B. dorsalis males could be increased via pre-release feeding on methyl eugenol. Males of the oriental fruit fly are strongly attracted to this plant-borne compound, which they ingest and use in the synthesis of the sex pheromone. Previous studies conducted in the laboratory and small field-cages have shown that males given methyl eugenol produce a more attractive pheromone for females and have a higher mating success rate than males denied methyl eugenol. Here, levels of egg sterility were compared following the release of wild-like flies and either methyl eugenol-fed (treated) or methyl eugenol-deprived (control) sterile males in large field enclosures at four over flooding ratios ranging from 5:1 to 60:1 (sterile: wild-like males). Treated sterile males were fed methyl eugenol for 1–4 h (depending on the over flooding ratio tested) 3 d prior to release. Eggs were dissected from introduced fruits (apples), incubated in the laboratory, and scored for hatch rate. The effect of methyl eugenol was most pronounced at lower over flooding ratios. At the 5:1 and 10:1 over flooding ratios, the level of egg sterility observed for treated, sterile males was significantly greater than that observed for control, sterile males. In addition, the incidence of egg sterility reported for treated sterile males at these lower over flooding ratios was similar to that noted for treated or control sterile males at the 30:1 or 60:1 over flooding ratios. This latter result, in particular, suggests that pre-release feeding on methyl eugenol allows for a reduction in the number of sterile flies that are produced and released, thus increasing the cost-effectiveness of the sterile insect technique. PMID:20569140

Shelf life of ready to use peeled shrimps as affected by thymol essential oil and modified atmosphere packaging.

PubMed

Mastromatteo, Marianna; Danza, Alessandra; Conte, Amalia; Muratore, Giuseppe; Del Nobile, Matteo Alessandro

2010-12-15

In this work the influence of different packaging strategies on the shelf life of ready to use peeled shrimps was investigated. First, the effectiveness of the coating (Coat) and the active coating loaded with different concentrations of thymol (Coat-500, Coat-1000, and Coat-1500) on the quality loss of the investigated food product packaged in air was addressed; afterwards, the thymol concentration that had shown the best performance was used in combination with MAP (5% O(2); 95% CO(2)). Microbial cell load of main spoilage microorganisms, pH and sensorial quality were monitored during the refrigerated storage. Results of the first step suggested that the sole coating did not affect the microbial growth. A slight antimicrobial effect was obtained when the coating was loaded with thymol and a concentration dependence was also observed. Moreover, the active coating was effective in minimizing the sensory quality loss of the investigated product, it was particularly true at the lowest thymol concentration. In the second step, the thymol concentration (1000 ppm) that showed the strike balance between microbial and sensorial quality was chosen in combination with MAP. As expected, MAP significantly affected the growth of the mesophilic bacteria. In particular, a cell load reduction of about 2 log cycle for the samples under MAP respect to that in air was obtained. Moreover, the MAP packaging inhibited the growth of the Pseudomonas spp. and hydrogen sulphide-producing bacteria. The MAP alone was not able to improve the shelf life of the uncoated samples. In fact, no significant difference between the control samples packaged in air and MAP was observed. Whilst, the use of coating under MAP condition prolonged the shelf life of about 6 days with respect to the same samples packaged in air. Moreover, when the MAP was used in combination with thymol, a further shelf life prolongation with respect to the samples packaged in air was observed. In particular, a shelf life of about 14 days for the active coating under MAP compared to the same samples in air (5 days) was obtained. Copyright © 2010 Elsevier B.V. All rights reserved.
Efficacy of albendazole in combination with thymol against Echinococcus multilocularis protoscoleces and metacestodes.

PubMed

María, Albani Clara; Celina, Elissondo María

2014-12-01

The larval (metacestode) stage of the tapeworm Echinococcus multilocularis causes alveolar echinococcosis (AE), a mainly hepatic disease characterized by continuous asexual proliferation of metacestodes by exogenous budding, resulting in the tumor-like, infiltrative growth of the parasite lesion. Current chemotherapeutical treatment of AE relies on the use of benzimidazoles, albendazole (ABZ) and mebendazole, but these drugs act parasitostatic rather than parasitocidal, and due to their low success rate they imply a lifelong application causing severe side effects. Thymol is one of the major components of the essential oils of Thymus and is a widely known anti-microbial agent. The aim of the present work was to compare the efficacy of albendazole (ABZ) and thymol separately or combined on E. multilocularis protoscoleces and metacestodes. For this purpose, microscopical examinations at different time points were carried out. Moreover the tegumentary enzyme gamma glutamyl transferase (GGT) was measured to quantify the damage in metacestodes. Even though treatments of in vitro cultured E. multilocularis protoscoleces or metacestodes with ABZ or/and thymol showed that the drugs have an adverse effect on parasite viability, the combination of the two compounds at the concentration of 10μg/ml showed the maximum anti-parasitic effect. Three days postincubation the first effects of the treatment were detected on protoscoleces and a marked reduction in viability (33%) was registered at day 18. Incubation of E. multilocularis metacestodes in the presence of ABZ 10μg/ml+thymol 10μg/ml during 10 days resulted in dramatic alterations such as strongly irregular and fissured surface and markedly disrupted vesicles. Scanning electron microscopy showed that protoscoleces as well as the germinal layer of E. multilocularis metacestodes were dramatically damaged following ABZ or/and thymol treatment. Also an important increase of tegumentary enzyme GGT was registered after 72h postincubation with both drugs. The data reported in this article demonstrate a clear in vitro effect of ABZ+thymol against E. multilocularis protoscoleces and metacestodes. Copyright © 2014 Elsevier B.V. All rights reserved.
Effect of initial temperature and concentration of catalyst in polyeugenol production

DOE Office of Scientific and Technical Information (OSTI.GOV)

Widayat, E-mail: yayat-99@yahoo.com; Center of Biomass and Renewable Energy Center of Research and Service Diponegoro University Jln Prof. Soedarto, SH. Semarang 50 239, Tel / Fax:; Fatuchrohman, Alviano

2015-12-29

Objective of this research to study influencing of sulfuric acid concentration and initials temperature on polymerization of eugenol. Eugenol is the largest compound in the clove oil that used as raw material. Eugenol was polymerized laboratory scale. Polymerization processing conducted in reactor at 30 minutes. Polyeugenol was obtained in polymerization was conducted at temperature 40°C and ratio eugenol to sulfuric acid 1:15 mole. This research was pbtained the highest yield 81.49%. However, the weight would be increase in according with increasing of initial temperature. The polymerization in temperature 50°C with 1:1.5 mole ratio has the heaviest molecule weight; 47,530.76 gr/mole.
Increasing strawberry shelf-life with carvacrol and methyl cinnamate antimicrobial vapors released from edible films

USDA-ARS?s Scientific Manuscript database

Shelf life of strawberries (Fragaria x ananassa) is limited by decay due to microbial growth that negatively impacts their color, texture, and weight. Plant natural volatile compounds, such as terpenoids and esters, have been reported to have antimicrobial properties. The effect of carvacrol (C) and...
Altered elementary calcium release events and enhanced calcium release by thymol in rat skeletal muscle.

PubMed

Szentesi, Péter; Szappanos, Henrietta; Szegedi, Csaba; Gönczi, Monika; Jona, István; Cseri, Julianna; Kovács, László; Csernoch, László

2004-03-01

The effects of thymol on steps of excitation-contraction coupling were studied on fast-twitch muscles of rodents. Thymol was found to increase the depolarization-induced release of calcium from the sarcoplasmic reticulum, which could not be attributed to a decreased calcium-dependent inactivation of calcium release channels/ryanodine receptors or altered intramembrane charge movement, but rather to a more efficient coupling of depolarization to channel opening. Thymol increased ryanodine binding to heavy sarcoplasmic reticulum vesicles, with a half-activating concentration of 144 micro M and a Hill coefficient of 1.89, and the open probability of the isolated and reconstituted ryanodine receptors, from 0.09 +/- 0.03 to 0.22 +/- 0.04 at 30 micro M. At higher concentrations the drug induced long-lasting open events on a full conducting state. Elementary calcium release events imaged using laser scanning confocal microscopy in the line-scan mode were reduced in size, 0.92 +/- 0.01 vs. 0.70 +/- 0.01, but increased in duration, 56 +/- 1 vs. 79 +/- 1 ms, by 30 micro M thymol, with an increase in the relative proportion of lone embers. Higher concentrations favored long events, resembling embers in control, with duration often exceeding 500 ms. These findings provide direct experimental evidence that the opening of a single release channel will generate an ember, rather than a spark, in mammalian skeletal muscle.
[Determination of capsaicinoids and eugenol in waste-edible-oil by liquid-liquid extraction and liquid chromatography-tandem mass spectrometry].

PubMed

Zhang, Zhong; Ren, Fei; Zhang, Pan

2012-11-01

A method was developed for the determination of capsaicinoids (capsaicin, dihydrocapsaicin and synthetic capsaicin) and eugenol in waste-edible-oil extracted by liquid-liquid extraction and liquid chromatography-tandem mass spectrometry (LC-MS/MS). The capsaicinoids and eugenol in waste-edible-oil were extracted by methanol, and then separated by a SUPEL COSIL ABZ + Plus dC18 column (150 mm x4.6 mm, 5 microm). The analysis was performed by MS/MS with electrospray ionization in positive and negative ion modes with multiple reaction monitoring (MRM). The limits of detection for capsaicin, dihydrocapsaicin, synthetic capsaicin and eugenol were 0.02, 0.03, 0.03 and 0.6 microg/L, respectively. The good linear relationships were obtained in certain concentration ranges of capsaicinoids and eugenol. The relative standard deviations (RSDs, n=5) of same-worker and different-worker were less than 5%. The method is exclusive, sensitive and accurate, and can be used in waste-edible-oil determination.
Piperine, a component of black pepper, decreases eugenol-induced cAMP and calcium levels in non-chemosensory 3T3-L1 cells.

PubMed

Yoon, Yeo Cho; Kim, Sung-Hee; Kim, Min Jung; Yang, Hye Jeong; Rhyu, Mee-Ra; Park, Jae-Ho

2015-01-01

This study investigated the effects of an ethanol extract of black pepper and its constituent, piperine, on odorant-induced signal transduction in non-chemosensory cells. An ethanol extract of black pepper decreased eugenol-induced cAMP and calcium levels in preadipocyte 3T3-L1 cells with no toxicity. Phosphorylation of CREB (cAMP response element-binding protein) was down-regulated by the black pepper extract. The concentration (133.8 mg/g) and retention time (5.5 min) of piperine in the ethanol extract were quantified using UPLC-MS/MS. Pretreatment with piperine decreased eugenol-induced cAMP and calcium levels in 3T3-L1 cells. Piperine also decreased the phosphorylation of CREB, which is up-regulated by eugenol. These results suggest that piperine inhibits the eugenol-induced signal transduction pathway through modulation of cAMP and calcium levels and phosphorylation of CREB in non-chemosensory cells.
Amidation reaction of eugenyl oxyacetate ethyl ester with 1,3 diaminopropane

NASA Astrophysics Data System (ADS)

Suryanti, V.; Wibowo, F. R.; Kusumaningsih, T.; Wibowo, A. H.; Khumaidah, S. A.; Wijayanti, L. A.

2016-04-01

Eugenol having various substituents on the aromatic ring (hydroxy, methoxy and allyl) are useful for starting material in synthesizing of its derivatives. Eugenol derivatives have shown wide future potential applications in many areas, especially as future drugs against many diseases. The aim of this work was to synthesize an amide of eugenol derivative. The starting material used was eugenol from clove oil and the reaction was conducted in 3 step reactions to give the final product. Firstly, eugenol was converted into eugenyl oxyacetate [2-(4-allyl-2-methoxyphenoxy) acetic acid] as a white crystal with 70.5% yield, which was then esterified with ethanol to have eugenyl oxyacetate ethyl ester [ethyl 2-(4-allyl-2-methoxyphenoxy) acetate] as brown liquid in 75.7%. The last step was the reaction between eugenyl oxyacetate ethyl ester and 1,3 diaminopropane to give 2-(4-allyl-2-methoxyphenoxy)-N-(3-aminopropyl) acetamide as a brown powder with 71.6% yield, where the amidation reaction was occurred.
Genes encoding chavicol/eugenol synthase from the creosote bush Larrea tridentata

DOEpatents

Lewis, Norman G.; Davin, Laurence B.; Kim, Sung -Jin; Vassao, Daniel Giddings; Patten, Ann M.; Eichinger, Dietmar

2015-09-15

Particular aspects provide novel methods for redirecting carbon allocation in plants or cell culture from lignification to inherently more useful and tractable materials, and to facilitate the generation of, e.g., biofuels from the remaining plant ro culture biomass. Particular aspects provided novel methods for converting monolignols into allyl/propenyl phenols, and for chavicol/eugenol formation or production. Additional aspects relate to the discovery of novel chavicol/eugenol synthases that convert p-coumaryl/coniferyl alcohol esters into chavicol/eugenol, and to novel compositions (e.g., novel proteins and nucleic acids encoding same), and novel methods using same for producing or forming chavicol/eugenol and other derivatives in cell culture and/or genetically modified plants, and for re-engineering the composition of plant biomass. Particular aspects provide novel methods for generation in culture or in planta of liquid/combustible allyl/propenyl phenols, and these phenolic products are utilized for (non-ethanol) biofuel/bioenergy purposes, while the remaining plant biomass facilitates the generation of other biofuels.
Influence of clove oil and eugenol on muscle contraction of silkworm (Bombyx mori).

PubMed

Kheawfu, Kantaporn; Pikulkaew, Surachai; Hamamoto, Hiroshi; Sekimizu, Kazuhisa; Okonogi, Siriporn

2017-05-30

Clove oil is used in fish anesthesia and expected to have a mechanism via glutamic receptor. The present study explores the activities of clove oil and its major compound, eugenol, in comparison with L-glutamic acid on glutamic receptor of silkworm muscle and fish anesthesia. It was found that clove oil and eugenol had similar effects to L-glutamic acid on inhibition of silkworm muscle contraction after treated with D-glutamic acid and kainic acid. Anesthetic activity of the test samples was investigated in goldfish. The results demonstrated that L-glutamic acid at 20 and 40 mM could induce the fish to stage 3 of anesthesia that the fish exhibited total loss of equilibrium and muscle tone, whereas clove oil and eugenol at 60 ppm could induce the fish to stage 4 of anesthesia that the reflex activity of the fish was lost. These results suggest that clove oil and eugenol have similar functional activities and mechanism to L-glutamic acid on muscle contraction and fish anesthesia.
Immediate contact reactions to chemicals in the fragrance mix and a study of the quenching action of eugenol.

PubMed

Safford, R J; Basketter, D A; Allenby, C F; Goodwin, B F

1990-11-01

In this study, the nature of non-immune immediate contact reactions (NIICR) produced by cinnamic aldehyde, benzoic acid and sorbic acid were investigated, with particular interest in the 'quenching' ability of eugenol. Three groups of human subjects were studied, and the guinea-pig ear was also used as a model of NIICR. Cinnamic aldehyde, benzoic acid and sorbic acid were all able to produce NIICR in the majority of subjects studied. There was a strong correlation between the susceptibility of each subject to each urticant, but no correlation between the susceptibility to NIICR and age, atopic status or tanning ability. Eugenol caused a reduction in NIICR induced by all three urticants. This 'quenching' effect was apparent even when the eugenol was applied up to 60 min prior to application of cinnamic aldehyde, and its effect was not eliminated by washing. In the guinea-pig-ear model, ear thickening was induced by all three urticants, and this response was inhibited by eugenol.
Stimulus Selection for Intranasal Sensory Isolation: Eugenol Is an Irritant

PubMed Central

Wise, Paul M.; Lundström, Johan N.

2012-01-01

Both the olfactory and the trigeminal systems are able to respond to intranasal presentations of chemical vapor. Accordingly, when the nose detects a volatile chemical, it is often unclear whether we smell it, feel it, or both. The distinction may often be unimportant in our everyday perception of fragrances or aromas, but it can matter in experiments that purport to isolate olfactory processes or study the interaction between olfaction and chemesthesis. Researchers turn to a small pool of compounds that are believed to be “pure olfactory” stimuli with little or no trigeminal impact. The current report reexamines one such commonly used compound, namely eugenol, a flavor and fragrance ingredient that has anesthetic properties under some conditions. Using a standard method involving many trials during an experimental session (Experiment 1), subjects were unable to reliably lateralize eugenol, consistent with claims that this compound is detected primarily through olfaction. However, with more limited exposure (Experiments 2 and 3), subjects were able to lateralize eugenol. We speculate that anesthetic properties of eugenol could blunt its trigeminal impact in some paradigms. Regardless, the current experiments suggest that eugenol can in fact stimulate the trigeminal nerve but in a complex concentration–dependent manner. Implications and strategies for selection of model odorants are discussed. PMID:22293937
Field Trapping Bactrocera latifrons (Diptera: Tephritidae) with Select Eugenol Analogs That Have Been Found to Attract Other 'Non-Responsive' Fruit Fly Species.

PubMed

McQuate, Grant T; Royer, Jane E; Sylva, Charmaine D

2018-05-01

Bactrocera latifrons (Hendel) (Diptera: Tephritidae) is a pest fruit fly species native to Oriental Asia which has invaded and established in Hawaii and Tanzania and has been recovered in detection trapping in California. It is largely non-responsive to the male lures cuelure and methyl eugenol. Alpha-ionol + cade oil is a moderately effective male B. latifrons attractant, but is not as attractive as cuelure or methyl eugenol are to other fruit fly species. An improved attractant is therefore desired. With the recent success in finding other non-responsive fruit fly species attracted to isoeugenol, methyl-isoeugenol, or dihydroeugenol in Australia and other countries, we wanted to assess whether B. latifrons might also respond to these “eugenol analogs.” Working with wild B. latifrons populations in Hawaii, we assessed the relative catch of B. latifrons in traps baited with the eugenol analogs with catch in traps baited with alpha-ionol, alpha-ionol + cade oil, or alpha-ionol + eugenol. Catch was significantly higher in traps baited with alpha-ionol + cade oil relative to traps with any of the other baits. There was, though, some male B. latifrons catch in traps baited with dihydroeugenol or isoeugenol but none in traps baited with methyl-isoeugenol.
Antimicrobial packaging of chicken fillets based on the release of carvacrol from chitosan/cyclodextrin films.

PubMed

Higueras, Laura; López-Carballo, Gracia; Hernández-Muñoz, Pilar; Catalá, Ramón; Gavara, Rafael

2014-10-01

Chitosan/cyclodextrin films (CS:CD) incorporating carvacrol were obtained by casting, and conditioned at 23°C and 75% relative humidity prior to being immersed in liquid carvacrol until they reached sorption equilibrium. In a previous work, the in vitro antimicrobial activity of these films was studied. In this work, active films were used to inhibit microbial growth in packaged chicken breast fillets. Samples of CS:CD films loaded with carvacrol, of different sizes and thus with different quantities of antimicrobial agent, were stuck to the aluminium lid used to seal PP/EVOH/PP cups containing 25g of chicken fillets. These samples were stored for 9days at 4°C. The packages were hermetically sealed and it was confirmed that they provided an infinite barrier to carvacrol. The partition of the antimicrobial agent within the food/packaging system was analysed. The antimicrobial devices rapidly released a large percentage of the agent load, amounts that were gained by the adhesive coating of the lid and especially by the chicken fillets. The latter were the main sorbent phase, with average concentrations ranging between 200 and 5000mg/Kg during the period of storage. The microbiota of the packaged fresh chicken fillets - mesophiles, psychrophiles, Pseudomonas spp., enterobacteria, lactic acid bacteria and yeasts and fungi - were analysed and monitored during storage. A general microbial inhibition was observed, increasing with the size of the active device. Inhibition with a 24cm(2) device ranged from 0.3 log reductions against lactic acid bacteria to 1.8logs against yeasts and fungi. However, the large amount of antimicrobial that was sorbed or that reacted with the fillet caused an unacceptable sensory deterioration. These high sorption values are probably due to a great chemical compatibility between chicken proteins and carvacrol. Copyright © 2014 Elsevier B.V. All rights reserved.
Eugenol in combination with lactic acid bacteria attenuates Listeria monocytogenes virulence in vitro and in invertebrate model Galleria mellonella.

PubMed

Upadhyay, Abhinav; Upadhyaya, Indu; Mooyottu, Shankumar; Venkitanarayanan, Kumar

2016-06-01

Listeria monocytogenes is a human enteric pathogen that causes severe foodborne illness in high-risk populations. Crossing the intestinal barrier is the first critical step for Listeria monocytogenes infection. Therefore, reducing L. monocytogenes colonization and invasion of intestinal epithelium and production of virulence factors could potentially control listeriosis in humans. This study investigated the efficacy of sub-inhibitory concentration (SIC) of the plant-derived antimicrobial eugenol, either alone, or in combination with five lactic acid bacteria (LAB), namely Bifidobacterium bifidum (NRRL-B41410), Lactobacillus reuteri (B-14172), Lactobacillus fermentum (B-1840), Lactobacillus plantarum (B-4496) and Lactococcus lactis subspecies lactis (B-633) in reducing Listeria monocytogenes adhesion to and invasion of human intestinal epithelial cells (Caco-2). Additionally, the effect of the aforementioned treatments on Listeria monocytogenes listeriolysin production, epithelial E-cadherin binding and expression of virulence genes was investigated. Moreover, the in vivo efficacy of eugenol-LAB treatments in reducing Listeria monocytogenes virulence in the invertebrate model Galleria mellonella was studied. Eugenol and LAB, either alone or in combination, significantly reduced Listeria monocytogenes adhesion to and invasion of intestinal cells (P < 0.05). Moreover, eugenol-LAB treatments decreased Listeria monocytogenes haemolysin production, E-cadherin binding and virulence gene expression (P < 0.05). In addition, the eugenol-LAB treatments significantly enhanced the survival rates of G. mellonella infected with lethal doses of Listeria monocytogenes (P < 0.05). The results highlight the antilisterial effect of eugenol either alone or in combination with LAB, and justify further investigations in a mammalian model.
Simultaneous determination of eugenol, isoeugenol and methyleugenol in fish fillet using gas chromatography coupled to tandem mass spectrometry.

PubMed

Ke, Changliang; Liu, Qi; Li, Liudong; Chen, Jiewen; Wang, Xunuo; Huang, Ke

2016-09-15

Gas chromatography (GC) coupled with triple quadrupole tandem mass spectrometry (MS/MS) operated in electron ionization mode (EI) has been shown to have advantages in the trace analysis of chemical compounds. Employing the instrument, a method has been built to simultaneously determine eugenol, isoeugenol' and methyleugenol, which have been widely used as fish anesthetic, in the fish fillet. Procedure for the sample preparation was achieved by using hexane extraction followed by phenyl solid phase extraction (SPE) cleanup, which was free of such steps as rotary evaporation and nitrogen blowing by taking the volatility of eugenol and its isomers into consideration. The method was validated by conducting recovery studies on fortified fish fillet samples at four concentrations. The linearity in the range of 5-500μg·L(-1) was forced through the origin giving a coefficient of determination (r(2)) greater than 0.9982. Limits of detection (LODs) for eugenol, isoeugenol' and methyleugenol were 0.4, 1.2' and 0.2μg·kg(-1), respectively. The limits of quantification (LOQs) were 1.2, 4' and 0.7μg·kg(-1) for eugenol, isoeugenol' and methyleugenol, respectively. The recoveries for eugenol and its isomers ranged from 76.4 to 99.9% with relative standard deviations (RSD) in a range from 2.18 to 15.5%. This method is quick, simple and suitable for determining the residues of eugenol, isoeugenol and methyleugenol simultaneously in batch samples of fish fillet. Copyright © 2016 Elsevier B.V. All rights reserved.
The multiple phenylpropene synthases in both Clarkia breweri and Petunia hybrida represent two distinct protein lineages

PubMed Central

Koeduka, Takao; Louie, Gordon V.; Orlova, Irina; Kish, Christine M.; Ibdah, Mwafaq; Wilkerson, Curtis G.; Bowman, Marianne E.; Baiga, Thomas J.; Noel, Joseph P.; Dudareva, Natalia; Pichersky, Eran

2009-01-01

Summary Many plants synthesize the volatile phenylpropene compounds eugenol and isoeugenol to serve in defense against herbivores and pathogens and to attract pollinators. Clarkia breweri flowers emit a mixture of eugenol and isoeugenol, while Petunia hybrida flowers emit mostly isoeugenol with small amounts of eugenol. We recently reported the identification of a petunia enzyme, PhIGS1, that catalyzes the formation of isoeugenol, and an Ocimum basilicum (basil) enzyme, ObEGS1, that produces eugenol. ObEGS1 and PhIGS1 both utilize coniferyl acetate, are 52% sequence identical, and belong to a family of NADPH-dependent reductases involved in secondary metabolism. Here we show that C. breweri flowers have two closely related proteins (96% identity), CbIGS1 and CbEGS1, that are similar to ObEGS1 (58% and 59%) and catalyze the formation of isoeugenol and eugenol, respectively. In vitro mutagenesis experiments demonstrate that substitution of only a single residue can substantially affect the product specificity of these enzymes. A third C. breweri enzyme identified, CbEGS2, also catalyzes the formation of eugenol from coniferyl acetate and is only 46% identical to CbIGS1 and CbEGS1 but more similar (>70%) to other types of reductases. We also found that petunia flowers contain an enzyme, PhEGS1, that is highly similar to CbEGS2 (82% identity) and that converts coniferyl acetate to eugenol. Our results indicate that plant enzymes with EGS and IGS activities have arisen multiple times and in different protein lineages. PMID:18208524
Phyto-fungicides: Structure activity relationships of the thymol derivatives against Rhizoctonia solani

USDA-ARS?s Scientific Manuscript database

Thymol, the key component of thyme oil and its derivatives were evaluated for their structure activity relationship as fungicide against Rhizoctonia solani. Since plant based chemicals are considered as “Generally Recognized as Safe” (GRAS) chemicals, there is a great potential to use phytochemicals...
Organic acids and thymol: unsuitable alternative control of Aethina tumida Murray (Coleoptera: Nitidulidae)

USDA-ARS?s Scientific Manuscript database

To explore alternative small hive beetle control strategies, established Varroa destructor and Galleria mellonella treatments with organic acids (formic, lactic, oxalic and acetic) and thymol were investigated in the laboratory against eggs, larvae and adult small hive beetle (SHB). As formic and ox...
Antagonistic effects of lipids against the bactericidal activity of thymol-beta-D-glucopyranoside

USDA-ARS?s Scientific Manuscript database

The gut of food-producing animals is a reservoir for zoonotic pathogens. Thymol is bactericidal against Salmonella, E. coli, and Campylobacter, but its rapid absorption from the proximal gut reveals a need for protective technologies to deliver effective concentrations to the lower gut where the pa...

The chemistry and beneficial bioactivities of carvacrol (4-isopropyl-2-methylphenol), a component of essential oils produced by aromatic plants and spices

USDA-ARS?s Scientific Manuscript database

Aromatic plants produce organic compounds that may be involved in the defense of plants against phytopathogenic insects, bacteria, fungi, and viruses. One of these compounds called carvacrol that is found in high concentrations in essential oils such as oregano has been reported to exhibit numerous...
Modeling the survival of Salmonella on slice cooked ham as a function of apple skin polyphenols, acetic acid, oregano essential oil and carvacrol

USDA-ARS?s Scientific Manuscript database

Response surface methodology was applied to investigate the combined effect of apple skin polyphenols (ASP), acetic acid (AA), oregano essential oil (O) and carvacrol (C) on the inactivation of Salmonella on sliced cooked ham. A full factorial experimental design was employed with control variables ...
Apple, carrot, and hibiscus edible films containing the plant antimicrobials carvacrol and cinnamaldehyde inactivate Salmonella Newport on organic leafy greens in sealed plastic bags

USDA-ARS?s Scientific Manuscript database

The objective of this study was to investigate the antimicrobial effects of carvacrol and cinnamaldehyde incorporated into apple, carrot and hibiscus based edible films against Salmonella Newport in contaminated organic leafy greens. The leafy greens tested included romaine and iceberg lettuce, and ...
Inhibitory Effects of Emodin, Thymol, and Astragalin on Leptospira interrogans-Induced Inflammatory Response in the Uterine and Endometrium Epithelial Cells of Mice.

PubMed

Zhang, Wenlong; Lu, Xiaojie; Wang, Wei; Ding, Zhuang; Fu, Yunhe; Zhou, Xiaofei; Zhang, Naisheng; Cao, Yongguo

2017-04-01

Leptospirosis is a systemic infection that causes, among others, acute kidney injury, acute liver disease, muscle pain, vasculitis, bleeding disorders, and reproductive loss. In an effort to reduce uterine inflammatory responses induced by Leptospira, we evaluated the anti-inflammation effects of emodin, thymol, and astragalin in a mouse model. Our results showed that treatment with emodin, thymol, and astragalin alleviated uterine inflammation induced by leptospira infection via suppression of pro-inflammatory cytokine expression and prevented tissue damage. Furthermore, we used primary endometrium epithelial cells to show that treatment with these chemicals inhibited the expression of pro-inflammatory cytokines TNF-α, IL-1β, and IL-6 using enzyme-linked immunosorbent assay and quantitative polymerase chain reaction. Western blot results showed that these chemicals suppressed the phosphorylation of p38, p65, extracellular signal-regulated kinase, and c-Jun N-terminal kinase. These results indicate that treatment with emodin, thymol, and astragalin suppressed inflammatory response by regulating NF-κB and mitogen-activated protein kinase signaling pathways in leptospira-infected uterine and endometrium epithelial cells of mice.
Evaluation of analytical techniques to determine AQUI-S(R) 20E (eugenol) concentrations in water

USGS Publications Warehouse

Meinertz, Jeffery R.; Hess, Karina R.

2013-01-01

There is a critical need in U.S. public aquaculture and fishery management programs for an immediate-release sedative, i.e. a compound that can be safely and effectively used to sedate fish and subsequently, allow for their immediate release. AQUI-S® 20E (10% active ingredient, eugenol; any use of trade, firm, or product names is for descriptive purposes only and does not imply endorsement by the U.S. Government) is being pursued for U.S. approval as an immediate-release sedative. As part of the approval process, data describing animal safety and efficacy are needed. Essential to conducting studies that generate those data, is a method to accurately and precisely determine AQUI-S® 20E concentrations in exposure baths. Spectrophotometric and solid phase extraction (SPE)–high pressure liquid chromatography (LC) methods were developed and evaluated as methods to determine AQUI-S® 20E (eugenol) concentrations in water, methods that could be applied to any situation where eugenol was being evaluated as a fish sedative. The spectrophotometric method was accurate and precise (accuracy, > 87%; precision, < 0.70 %CV) when determining eugenol concentrations in solutions of 50 to 1000 mg/L AQUI-S® 20E made with LC grade water and water with varying pH and hardness. The spectrophotometric method's accuracy was negatively affected when analyzing water containing fish feed. The SPE–LC method was also accurate and precise (accuracy > 86%; precision < 8.9 %CV) when determining eugenol concentrations in solutions of 50 to 1000 mg/L AQUI-S® 20E made with LC grade water and water with varying pH and hardness. The SPE–LC method was influenced to a lesser degree by the presence of fish feed indicating greater specificity for eugenol.
GC-MS method validation and levels of methyl eugenol in a diverse range of tea tree (Melaleuca alternifolia) oils.

PubMed

Raymond, Carolyn A; Davies, Noel W; Larkman, Tony

2017-03-01

Tea tree oil distilled from Melaleuca alternifolia has widespread use in the cosmetic industry as an antimicrobial as well as for other functions in topical products. Concerns were first raised by the European Commission's Scientific Committee on Consumer Products in 2004 about the level of the potentially carcinogenic phenylpropanoid compound methyl eugenol in tea tree oil. Limits on oil content in different types of cosmetic products were set based on a reported upper level of 0.9% methyl eugenol in the oil. A previous publication indicated that these levels were based on oil from a Melaleuca species not used in the commercial production of oil. Even the highest recorded levels in Melaleuca alternifolia, the overwhelmingly most common species used, were ∼15 times less than this, meaning that more oil could be safely used in the products. The current study, including details on methodology and reproducibility, extends that work across a suite of 57 plantation-sourced oils from a range of geographical locations and production years, as well as many Australian and international commercial oils. Lower levels of methyl eugenol in oils of known provenance were confirmed, with a recorded range of 160-552 ppm and a mean of 337 ppm. Analysis of variance showed methyl eugenol levels in Australian plantation oils to be correlated to the geographical region but not to the year of production. Average methyl eugenol levels in commercial oils were significantly lower, and these samples were divided into an authentic group and a group that were suspected of being adulterated based on an independent test. Authentic commercial oils had similar levels of methyl eugenol to Australian provenance material, whilst the oils classed as suspect had significantly lower levels.
Evaluation of a Method for Quantifying Eugenol Concentrations in the Fillet Tissue from Freshwater Fish Species.

PubMed

Meinertz, Jeffery R; Schreier, Theresa M; Porcher, Scott T; Smerud, Justin R

2016-01-01

AQUI-S 20E(®) (active ingredient, eugenol; AQUI-S New Zealand Ltd, Lower Hutt, New Zealand) is being pursued for approval as an immediate-release sedative in the United States. A validated method to quantify the primary residue (the marker residue) in fillet tissue from AQUI-S 20E-exposed fish was needed. A method was evaluated for determining concentrations of the AQUI-S 20E marker residue, eugenol, in freshwater fish fillet tissue. Method accuracies from fillet tissue fortified at nominal concentrations of 0.15, 1, and 60 μg/g from six fish species ranged from 88-102%. Within-day and between-day method precisions (% CV) from the fortified tissue were ≤8.4% CV. There were no coextracted compounds from the control fillet tissue of seven fish species that interfered with eugenol analyses. Six compounds used as aquaculture drugs did not interfere with eugenol analyses. The lower limit of quantitation (LLOQ) was 0.012 μg/g. The method was robust, i.e., in most cases, minor changes to the method did not impact method performance. Eugenol was stable in acetonitrile-water (3 + 7, v/v) for at least 14 days, in fillet tissue extracts for 4 days, and in fillet tissue stored at ~ -80°C for at least 84 days.
Evaluation of a method for quantifying eugenol concentrations in the fillet tissue from freshwater fish species

USGS Publications Warehouse

Meinertz, Jeffery R.; Schreier, Theresa M.; Porcher, Scott T.; Smerud, Justin R.

2016-01-01

AQUI-S 20E® (active ingredient, eugenol; AQUI-S New Zealand Ltd, Lower Hutt, New Zealand) is being pursued for approval as an immediate-release sedative in the United States. A validated method to quantify the primary residue (the marker residue) in fillet tissue from AQUI-S 20E–exposed fish was needed. A method was evaluated for determining concentrations of the AQUI-S 20E marker residue, eugenol, in freshwater fish fillet tissue. Method accuracies from fillet tissue fortified at nominal concentrations of 0.15, 1, and 60 μg/g from six fish species ranged from 88–102%. Within-day and between-day method precisions (% CV) from the fortified tissue were ≤8.4% CV. There were no coextracted compounds from the control fillet tissue of seven fish species that interfered with eugenol analyses. Six compounds used as aquaculture drugs did not interfere with eugenol analyses. The lower limit of quantitation (LLOQ) was 0.012 μg/g. The method was robust, i.e., in most cases, minor changes to the method did not impact method performance. Eugenol was stable in acetonitrile–water (3 + 7, v/v) for at least 14 days, in fillet tissue extracts for 4 days, and in fillet tissue stored at ~ −80°C for at least 84 days.
Antifungal activity of the clove essential oil from Syzygium aromaticum on Candida, Aspergillus and dermatophyte species.

PubMed

Pinto, Eugénia; Vale-Silva, Luís; Cavaleiro, Carlos; Salgueiro, Lígia

2009-11-01

The composition and antifungal activity of clove essential oil (EO), obtained from Syzygium aromaticum, were studied. Clove oil was obtained commercially and analysed by GC and GC-MS. The EO analysed showed a high content of eugenol (85.3 %). MICs, determined according to Clinical and Laboratory Standards Institute protocols, and minimum fungicidal concentration were used to evaluate the antifungal activity of the clove oil and its main component, eugenol, against Candida, Aspergillus and dermatophyte clinical and American Type Culture Collection strains. The EO and eugenol showed inhibitory activity against all the tested strains. To clarify its mechanism of action on yeasts and filamentous fungi, flow cytometric and inhibition of ergosterol synthesis studies were performed. Propidium iodide rapidly penetrated the majority of the yeast cells when the cells were treated with concentrations just over the MICs, meaning that the fungicidal effect resulted from an extensive lesion of the cell membrane. Clove oil and eugenol also caused a considerable reduction in the quantity of ergosterol, a specific fungal cell membrane component. Germ tube formation by Candida albicans was completely or almost completely inhibited by oil and eugenol concentrations below the MIC values. The present study indicates that clove oil and eugenol have considerable antifungal activity against clinically relevant fungi, including fluconazole-resistant strains, deserving further investigation for clinical application in the treatment of fungal infections.
Yield and oil composition of 38 basil (Ocimum basilicum L.) accessions grown in Mississippi.

PubMed

Zheljazkov, Valtcho D; Callahan, Amber; Cantrell, Charles L

2008-01-09

A field experiment was conducted to assess yield, oil content, and composition of 38 genotypes of sweet basil ( Ocimum basilicum L.). Overall, biomass yields were high and comparable to those reported in the literature. However, basil genotypes differed significantly with respect to oil content and composition. Oil content of the tested accessions varied from 0.07% to 1.92% in dry herbage. On the basis of the oil composition, basil accessions were divided into seven groups: (1) high-linalool chemotype [19-73% (-)-linalool], (2) linalool-eugenol chemotype [six chemotypes with 28-66% (-)-linalool and 5-29% eugenol], (3) methyl chavicol chemotype [six accessions with 20-72% methyl chavicol and no (-)-linalool], (4) methyl chavicol-linalool chemotype [six accessions with 8-29% methyl chavicol and 8-53% (-)-linalool], (5) methyl eugenol-linalool chemotype [two accessions with 37% and 91% methyl eugenol and 60% and 15% (-)-linalool], (6) methyl cinnamate-linalool chemotype [one accession with 9.7% methyl cinnamate and 31% (-)-linalool], and (7) bergamotene chemotype [one accession with bergamotene as major constituent, 5% eucalyptol, and <1% (-)-linalool]. Our results demonstrated that basil could be a viable essential oil crop in Mississippi. The availability of various chemotypes offers the opportunity for production of basil to meet the market requirements of specific basil oils or individual compounds such as (-)-linalool, eugenol, methyl chavicol, methyl cinnamate, or methyl eugenol.
Evaluation of analytical techniques to determine AQUI-S® 20E (eugenol) concentrations in water

USGS Publications Warehouse

Meinertz, Jeffery R.; Hess, Karina R.

2014-01-01

There is a critical need in U.S. public aquaculture and fishery management programs for an immediate-release sedative, i.e. a compound that can be safely and effectively used to sedate fish and subsequently, allow for their immediate release. AQUI-S® 20E (10% active ingredient, eugenol; any use of trade, firm, or product names is for descriptive purposes only and does not imply endorsement by the U.S. Government) is being pursued for U.S. approval as an immediate-release sedative. As part of the approval process, data describing animal safety and efficacy are needed. Essential to conducting studies that generate those data, is a method to accurately and precisely determine AQUI-S® 20E concentrations in exposure baths. Spectrophotometric and solid phase extraction (SPE)–high pressure liquid chromatography (LC) methods were developed and evaluated as methods to determine AQUI-S® 20E (eugenol) concentrations in water, methods that could be applied to any situation where eugenol was being evaluated as a fish sedative. The spectrophotometric method was accurate and precise (accuracy, > 87%; precision, 86%; precision < 8.9 %CV) when determining eugenol concentrations in solutions of 50 to 1000 mg/L AQUI-S® 20E made with LC grade water and water with varying pH and hardness. The SPE–LC method was influenced to a lesser degree by the presence of fish feed indicating greater specificity for eugenol.
Acaricidal activity of thymol against larvae of Rhipicephalus microplus (Acari: Ixodidae) under semi-natural conditions.

PubMed

Araújo, Laryssa Xavier; Novato, Tatiane Pinheiro Lopes; Zeringota, Viviane; Matos, Renata Silva; Senra, Tatiane Oliveira Souza; Maturano, Ralph; Prata, Márcia Cristina Azevedo; Daemon, Erik; Monteiro, Caio Márcio Oliveira

2015-09-01

This is the first study to investigate the activity of thymol on Rhipicephalus microplus larvae under semi-natural conditions. For this purpose, tests were conducted in pots with Brachiaria decumbens seedlings containing cattle tick larvae. Thymol, diluted in ethanol 50° GL, was tested at concentrations of 2.5, 5.0, 10.0, 15.0, and 20.0 mg/mL, along with the control group treated with the solvent alone. Each treatment was composed of five pots (1 pot = a repetition). The experiment was performed in three steps. On the first day, the larvae were applied at the base of the signalgrass. Twenty-four hours later, approximately 25 mL of the solution was applied with thymol on the top of the vegetation in each pot. The survival of the larvae was measured 24 h after application of the solutions. Each pot was analyzed individually, and the grass fillets contained larvae were cut with scissors, placed in Petri dishes, and taken to the laboratory to count the number of living larvae. At the highest concentrations (10, 15, and 20 mg /mL), the number of live larvae declined by more than 95 % in relation to the control group. The lethal concentration 50 % (LC50) and LC90 values were 3.45 and 9.25 mg/ml, respectively. The application of thymol in semi-natural conditions starting concentration of 10 mg/mL significantly reduced the number of living R. microplus larvae.
Supercritical CO2 impregnation of PLA/PCL films with natural substances for bacterial growth control in food packaging.

PubMed

Milovanovic, Stoja; Hollermann, Gesa; Errenst, Cornelia; Pajnik, Jelena; Frerich, Sulamith; Kroll, Stephen; Rezwan, Kurosch; Ivanovic, Jasna

2018-05-01

Biodegradable polymers with antibacterial properties are highly desirable materials for active food packaging applications. Thymol, a dietary monoterpene phenol with a strong antibacterial activity is abundant in plants belonging to the genus Thymus. This study presents two approaches for supercritical CO 2 impregnation of poly(lactic acid)(PLA)/poly(ε-caprolactone)(PCL) blended films to induce antibacterial properties of the material: (i) a batch impregnation process for loading pure thymol, and (ii) an integrated supercritical extraction-impregnation process for isolation of thyme extract and its incorporation into the films, operated in both batch or semi-continuous modes with supercritical solution circulation. The PCL content in films, impregnation time and CO 2 flow regime were varied to maximize loading of the films with thymol or thyme extract with preserving films' structure and thermal stability. Representative film samples impregnated with thymol and thyme extract were tested against Gram (-) (Escherichia coli) and Gram(+) (Bacillus subtilis) model strains, by measuring their metabolic activity and re-cultivation after exposure to the films. The film containing thymol (35.8 wt%) showed a strong antibacterial activity leading to a total reduction of bacterial cell viability. Proposed processes enable fast, controlled and organic solvent-free fabrication of the PLA/PCL films containing natural antibacterial substances at moderately low temperature, with a compact structure and a good thermal stability, for potential use as active food packaging materials. Copyright © 2018 Elsevier Ltd. All rights reserved.
Effect of citral and carvacrol on the susceptibility of Listeria monocytogenes and Listeria innocua to antibiotics.

PubMed

Zanini, S F; Silva-Angulo, A B; Rosenthal, A; Rodrigo, D; Martínez, A

2014-05-01

The aim of this study was to evaluate the antibiotic susceptibility of Listeria innocua (L. innocua) and Listeria monocytogenes (L. monocytogenes) cells in the presence of citral and carvacrol at sublethal concentrations in an agar medium. The presence of terpenes in the L. monocytogenes and L. innocua culture medium provided a reduction in the minimal inhibitory concentration (MIC) of all the antibiotics tested. These effects were dependent on the concentration of terpenes present in the culture medium. The combination of citral and carvacrol potentiated antibiotic activity by reducing the MIC values of bacitracin and colistin from 32.0 and 128.0 μg ml⁻¹ to 1.0 and 2.0 μg ml⁻¹, respectively. Thus, both Listeria species became more susceptible to these drugs. In this way, the colistin and bacitracin resistance of L. monocytogenes and L. innocua was reversed in the presence of terpenes. Results obtained in this study show that the phytochemicals citral and carvacrol potentiate antibiotic activity, reducing the MIC values of cultured L. monocytogenes and L. innocua. Phytochemicals citral and carvacrol potentiate antibiotic activity of erythromycin, bacitracin and colistin by reducing the MIC values of cultured Listeria monocytogenes and Listeria innocua. This effect in reducing the MIC values of the antibiotics tested in both micro-organisms was increased when natural antimicrobials were combined. This finding indicated that the combination among terpenes and antibiotic may contribute in reducing the required dosage of antibiotics due to the possible effect of terpenes on permeation barrier of the micro-organism cell membrane. © 2014 The Society for Applied Microbiology.
Anti-Giardia activity of Syzygium aromaticum essential oil and eugenol: effects on growth, viability, adherence and ultrastructure.

PubMed

Machado, M; Dinis, A M; Salgueiro, L; Custódio, José B A; Cavaleiro, C; Sousa, M C

2011-04-01

The present work evaluates the anti-Giardia activity of Syzygium aromaticum and its major compound eugenol. The effects were evaluated on parasite growth, adherence, viability and ultrastructure. S. aromaticum essential oil (IC(50)=134 μg/ml) and eugenol (IC(50)=101 μg/ml) inhibited the growth of G. lamblia. The essential oil inhibited trophozoites adherence since the first hour of incubation and was able to kill almost 50% of the parasites population in a time dependent manner. The eugenol inhibited G. lamblia trophozoites adherence since the third hour and not induce cell lyses. The main morphological alterations were modifications on the cell shape, presence of precipitates in the cytoplasm, autophagic vesicles, internalization of flagella and ventral disc, membrane blebs, and intracellular and nuclear clearing. Taken together, our findings lead us to propose that eugenol was responsible for the anti-giardial activity of the S. aromaticum essential oil and both have potential for use as therapeutic agents against giardiasis. Copyright © 2011 Elsevier Inc. All rights reserved.
Inhibitory components from the buds of clove (Syzygium aromaticum) on melanin formation in B16 melanoma cells.

PubMed

Arung, Enos Tangke; Matsubara, Eri; Kusuma, Irawan Wijaya; Sukaton, Edi; Shimizu, Kuniyoshi; Kondo, Ryuichiro

2011-03-01

In the course to find a new whitening agent, we evaluated the methanol extract from bud of clove (Syzygium aromaticum) on melanin formation in B16 melanoma cells. Eugenol and eugenol acetate were isolated as the active compounds and showed melanin inhibition of 60% and 40% in B16 melanoma cell with less cytotoxicity at the concentration of 100 and 200 μg/mL, respectively. Furthermore, an essential oil prepared from the bud of clove, which contain eugenol and eugenol acetate as dominant components, showed melanin inhibition of 50% and 80% in B16 melanoma cells at the concentration of 100 and 200 μg/mL, respectively. Copyright Â© 2010 Elsevier B.V. All rights reserved.
Thymbra capitata essential oil as potential therapeutic agent against Gardnerella vaginalis biofilm-related infections.

PubMed

Machado, Daniela; Gaspar, Carlos; Palmeira-de-Oliveira, Ana; Cavaleiro, Carlos; Salgueiro, Lígia; Martinez-de-Oliveira, José; Cerca, Nuno

2017-04-01

To evaluate the antibacterial activity of Thymbra capitata essential oil and its main compound, carvacrol, against Gardnerella vaginalis grown planktonically and as biofilms, and its effect of vaginal lactobacilli. Minimal inhibitory concentration, minimal lethal concentration determination and flow cytometry analysis were used to assess the antibacterial effect against planktonic cells. Antibiofilm activity was measured through quantification of biomass and visualization of biofilm structure by confocal laser scanning microscopy. T. capitata essential oil and carvacrol exhibited a potent antibacterial activity against G. vaginalis cells. Antibiofilm activity was more evident with the essential oil than carvacrol. Furthermore, vaginal lactobacilli were significantly more tolerant to the essential oil. T. capitata essential oil stands up as a promising therapeutic agent against G. vaginalis biofilm-related infections.
Reversal of efflux mediated antifungal resistance underlies synergistic activity of two monoterpenes with fluconazole.

PubMed

Ahmad, Aijaz; Khan, Amber; Manzoor, Nikhat

2013-01-23

Thymol (THY) and carvacrol (CARV), the principal chemical components of thyme oil have long been known for their wide use in medicine due to antimicrobial and disinfectant properties. This study, however, draws attention to a possible synergistic antifungal effect of these monoterpenes with azole antimycotic-fluconazole. Resistance to azoles in Candida albicans involves over-expression of efflux-pump genes MDR1, CDR1, CDR2 or mutations and over-expression of target gene ERG11. The inhibition of drug efflux pumps is considered a feasible strategy to overcome clinical antifungal resistance. To put forward this approach, we investigated the combination effects of these monoterpenes and FLC against 38 clinically obtained FLC-sensitive, and eleven FLC-resistant Candida isolates. Synergism was observed with combinations of THY-FLC and CARV-FLC evaluated by checkerboard microdilution method and nature of the interactions was calculated by FICI. In addition, antifungal activity was assessed using agar-diffusion and time-kill curves. The drug efflux activity was determined using two dyes, Rhodamine6G (R6G) and fluorescent Hoechst 33342. No significant differences were observed in dye uptakes between FLC-susceptible and resistant isolates, incubated in glucose free buffer. However, a significantly higher efflux was recorded in FLC-resistant isolates when glucose was added. Both monoterpenes inhibited efflux by 70-90%, showing their high potency to block drug transporter pumps. Significant differences, in the expression levels of CDR1 and MDR1, induced by monoterpenes revealed reversal of FLC-resistance. The selectively fungicidal characteristics and ability to restore FLC susceptibility in resistant isolates signify a promising candidature of THY and CARV as antifungal agents in combinational treatments for candidiasis. Copyright © 2012 Elsevier B.V. All rights reserved.
Antimicrobial activity of Satureja montana L. essential oil against Clostridium perfringens type A inoculated in mortadella-type sausages formulated with different levels of sodium nitrite.

PubMed

de Oliveira, Thales Leandro Coutinho; de Araújo Soares, Rodrigo; Ramos, Eduardo Mendes; das Graças Cardoso, Maria; Alves, Eduardo; Piccoli, Roberta Hilsdorf

2011-01-05

This research evaluated the antimicrobial effect of the winter savory (Satureja montana L.) essential oil (EO) against Clostridium perfringens type A (ATCC 3624) inoculated in mortadella-type sausages formulated with different levels of sodium nitrite (NaNO₂: 0 ppm, 100 ppm and 200 ppm) in addition to EO at concentrations of 0.0%, 0.78%, 1.56% and 3.125% stored at 25°C for 30 days. The EO extracted by hydrodistillation and analyzed by gas chromatography-mass spectrometry (CG-MS) was tested in vitro using an agar well diffusion method for determination of minimum inhibitory concentration (MIC) on C. perfringens. According to compositional analysis of the winter savory EO, 26 chemical compounds were identified, and the major constituents were thymol (28.99%), p-cymene (12.00%), linalool (11.00%) and carvacrol (10.71%). The results obtained showed that EO applied at a concentration of 1.56%, which was defined as the MIC, exhibited antimicrobial activity against C. perfringens in the in vitro assays, and the transmission electron microscopy (TEM) revealed structural damage and cell lysis of C. perfringens caused by EO treatment. A synergistic effect between NaNO₂ and EO was observed. In mortadella-type sausages formulated with 100 ppm of NaNO₂ and EO at all concentrations tested, the population of target microorganisms was reduced (p≤0.05) compared to control samples during all storage period. This data suggests the potential combined use of savory EO and minimal amounts of the synthetic additive, NaNO₂ to control C. perfringens in mortadella, which goes according to current market trends, where consumers are requesting natural products. Copyright © 2010 Elsevier B.V. All rights reserved.
In vitro activity of origanum vulgare essential oil against candida species

PubMed Central

Cleff, Marlete Brum; Meinerz, Ana Raquel; Xavier, Melissa; Schuch, Luiz Filipe; Schuch, Luiz Filipe; Araújo Meireles, Mário Carlos; Alves Rodrigues, Maria Regina; de Mello, João Roberto Braga

2010-01-01

The aim of this study was to evaluate the in vitro activity of the essential oil extracted from Origanum vulgare against sixteen Candida species isolates. Standard strains tested comprised C. albicans (ATCC strains 44858, 4053, 18804 and 3691), C. parapsilosis (ATCC 22019), C. krusei (ATCC 34135), C. lusitaniae (ATCC 34449) and C. dubliniensis (ATCC MY646). Six Candida albicans isolates from the vaginal mucous membrane of female dogs, one isolate from the cutaneous tegument of a dog and one isolate of a capuchin monkey were tested in parallel. A broth microdilution technique (CLSI) was used, and the inoculum concentration was adjusted to 5 x 106 CFU mL-1. The essential oil was obtained by hydrodistillation in a Clevenger apparatus and analyzed by gas chromatography. Susceptibility was expressed as Minimal Inhibitory Concentration (MIC) and Minimal Fungicidal Concentration (MFC). All isolates tested in vitro were sensitive to O. vulgare essential oil. The chromatographic analysis revealed that the main compounds present in the essential oil were 4-terpineol (47.95%), carvacrol (9.42%), thymol (8.42%) and □-terpineol (7.57%). C. albicans isolates obtained from animal mucous membranes exhibited MIC and MFC values of 2.72 μL mL-1 and 5 μL mL-1, respectively. MIC and MFC values for C. albicans standard strains were 2.97 μL mL-1 and 3.54 μL mL-1, respectively. The MIC and MFC for non-albicans species were 2.10 μL mL-1 and 2.97 μL mL-1, respectively. The antifungal activity of O. vulgare essential oil against Candida spp. observed in vitro suggests its administration may represent an alternative treatment for candidiasis. PMID:24031471

In vivo study of the efficacy of the aromatic water of Zataria multiflora on hydatid cysts.

PubMed

Moazeni, Mohammad; Larki, Sara; Saharkhiz, Mohammad Jamal; Oryan, Ahmad; Ansary Lari, Maryam; Mootabi Alavi, Amir

2014-10-01

Gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) were employed to determine the chemical composition of the essential oil (EO) from aromatic water (AW) of Zataria multiflora. Thymol (66.9%), carvacrol (15.2%), and carvone (7.3%) were found to be the major EO constituents. Eighty laboratory BALB/c mice were infected intraperitoneally by injection of 1,500 viable protoscolices and were divided into prevention (40 mice) and therapeutic (40 mice) groups. To prove the preventive effect of the Z. multiflora AW on development of hydatid cysts, the 40 infected mice were allocated into three treatment groups, including the albendazole group (10 mice that received 150 mg/kg body weight/day for 10 days), the Z. multiflora AW group (15 mice that received 20 ml/liter in drinking water for 8 months), and a control group (15 mice that received no treatment). To estimate the therapeutic effect of the Z. multiflora AW on the hydatid cyst, after 8 months of infection, the 15 remaining mice were allocated into three experimental treatment groups of five animals each, including the albendazole group (300 mg/kg/day for 20 days), Z. multiflora AW group (40 ml/liter in drinking water for 30 days), and control group (no treatment). All mice were then euthanized, and the sizes and weights of the cysts as well as their ultrastructural changes were investigated. The weights and sizes of the hydatid cysts significantly decreased upon treatment with the Z. multiflora AW in both the preventive and therapeutic groups (P < 0.05). The results of scanning electron microscopy also showed considerable damage in the germinal layer of the hydatid cysts recovered from the treated animals. Copyright © 2014, American Society for Microbiology. All Rights Reserved.
Efficacy of plant essential oils on postharvest control of rots caused by fungi on different stone fruits in vivo.

PubMed

Lopez-Reyes, Jorge Giovanny; Spadaro, Davide; Prelle, Ambra; Garibaldi, Angelo; Gullino, Maria Lodovica

2013-04-01

The antifungal activity of plant essential oils was evaluated as postharvest treatment on stone fruit against brown rot and grey mold rot of stone fruit caused by Monilinia laxa and Botrytis cinerea, respectively. The essential oils from basil (Ocimum basilicum), fennel (Foeniculum sativum), lavender (Lavandula officinalis), marjoram (Origanum majorana), oregano (Origanum vulgare), peppermint (Mentha piperita), rosemary (Rosmarinus officinalis), sage (Salvia officinalis), savory (Satureja montana), thyme (Thymus vulgaris), and wild mint (Mentha arvensis) were tested at two different concentrations on apricots (cv. Kyoto and cv. Tonda di Costigliole), nectarines (cv. Big Top and cv. Nectaross) and plums (cv. Italia and cv. TC Sun). The volatile composition of the essential oils tested was determined by gas chromatography-mass spectrometry analysis. The treatments containing essential oils from oregano, savory, and thyme at 1% (vol/vol) controlled both B. cinerea and M. laxa growing on apricots cv. Tonda di Costigliole and plums cv. Italia and cv. TC Sun; however, the same treatments were phytotoxic for the carposphere of nectarines cv. Big Top and cv. Nectaross. Treatments with 10% (vol/vol) essential oils were highly phytotoxic, notwithstanding their efficacy against the pathogens tested. The essential oils containing as major components α-pinene, p-cymene, carvacrol, and thymol showed similar results on stone fruit, so their antimicrobial activity and the phytotoxicity produced could be based on the concentration of their principal compounds and their synergistic activity. The efficacy of the essential oil treatments on control of fungal pathogens in postharvest depended on the fruit cultivar, the composition and concentration of the essential oil applied, and the length of storage.
The bovine TRPV3 as a pathway for the uptake of Na+, Ca2+, and NH4+

PubMed Central

Liebe, Franziska; Liebe, Hendrik

2018-01-01

Absorption of ammonia from the gastrointestinal tract results in problems that range from hepatic encephalopathy in humans to poor nitrogen efficiency of cattle with consequences for the global climate. Previous studies on epithelia and cells from the native ruminal epithelium suggest functional involvement of the bovine homologue of TRPV3 (bTRPV3) in ruminal NH4+ transport. Since the conductance of TRP channels to NH4+ has never been studied, bTRPV3 was overexpressed in HEK-293 cells and investigated using the patch-clamp technique and intracellular calcium imaging. Control cells contained the empty construct. Divalent cations blocked the conductance for monovalent cations in both cell types, with effects higher in cells expressing bTRPV3. In bTRPV3 cells, but not in controls, menthol, thymol, carvacrol, or 2-APB stimulated whole cell currents mediated by Na+, Cs+, NH4+, and K+, with a rise in intracellular Ca2+ observed in response to menthol. While only 25% of control patches showed single-channel events (with a conductance of 40.8 ± 11.9 pS for NH4+ and 25.0 ± 5.8 pS for Na+), 90% of bTRPV3 patches showed much larger conductances of 127.8 ± 4.2 pS for Na+, 240.1 ± 3.6 pS for NH4+, 34.0 ± 1.7 pS for Ca2+, and ~ 36 pS for NMDG+. Open probability, but not conductance, rose with time after patch excision. In conjunction with previous research, we suggest that bTRPV3 channels may play a role in the transport of Na+, K+, Ca2+ and NH4+ across the rumen with possible repercussions for understanding the function of TRPV3 in other epithelia. PMID:29494673
The bovine TRPV3 as a pathway for the uptake of Na+, Ca2+, and NH4.

PubMed

Schrapers, Katharina T; Sponder, Gerhard; Liebe, Franziska; Liebe, Hendrik; Stumpff, Friederike

2018-01-01

Absorption of ammonia from the gastrointestinal tract results in problems that range from hepatic encephalopathy in humans to poor nitrogen efficiency of cattle with consequences for the global climate. Previous studies on epithelia and cells from the native ruminal epithelium suggest functional involvement of the bovine homologue of TRPV3 (bTRPV3) in ruminal NH4+ transport. Since the conductance of TRP channels to NH4+ has never been studied, bTRPV3 was overexpressed in HEK-293 cells and investigated using the patch-clamp technique and intracellular calcium imaging. Control cells contained the empty construct. Divalent cations blocked the conductance for monovalent cations in both cell types, with effects higher in cells expressing bTRPV3. In bTRPV3 cells, but not in controls, menthol, thymol, carvacrol, or 2-APB stimulated whole cell currents mediated by Na+, Cs+, NH4+, and K+, with a rise in intracellular Ca2+ observed in response to menthol. While only 25% of control patches showed single-channel events (with a conductance of 40.8 ± 11.9 pS for NH4+ and 25.0 ± 5.8 pS for Na+), 90% of bTRPV3 patches showed much larger conductances of 127.8 ± 4.2 pS for Na+, 240.1 ± 3.6 pS for NH4+, 34.0 ± 1.7 pS for Ca2+, and ~ 36 pS for NMDG+. Open probability, but not conductance, rose with time after patch excision. In conjunction with previous research, we suggest that bTRPV3 channels may play a role in the transport of Na+, K+, Ca2+ and NH4+ across the rumen with possible repercussions for understanding the function of TRPV3 in other epithelia.
Anti-tubercular activity of eleven aromatic and medicinal plants occurring in Colombia.

PubMed

Bueno-Sánchez, Juan Gabriel; Martínez-Morales, Jairo René; Stashenko, Elena E; Ribón, Wellman

2009-03-01

Human tuberculosis is a contagious-infectious disease mainly caused by Mycobacterium tuberculosis. Although regimens exist for treating tuberculosis, they are far from ideal. Development of effective strategies for treatment of human tuberculosis has posed a challenge, considering the increase in infections associated with the human immunodeficiency virus and immunocompromised patients. Essential oils--volatile, aromatic oil extracts from plants--have been used in traditional treatment of many diseases; however careful investigation of these oils has not been undertaken with respect to treatments of tuberculosis. The in vitro antitubercular activity of essential oils from 11 medicinal plants grown in Colombia were assessed for efficacy as new medications (phytomedicines) for treatment of M. tuberculosis H37Rv. Essential oil extraction and analysis were performed as described Stashenko et al. (2004). Minimal inhibitory concentrations were determined by a colorimetric macrodilution method, following the protocol described by Abate et al. (1998). Isoniazide and rifampin were used as control treatments. Bactericidal and bacteriostatic activity was measured using the method developed by the Clinical and Laboratory Standards Institute consigned in the M26-A protocol. Essential oils from Achyrocline alata and Swinglea glutinosa were the most active with minimal inhibitory concentrations of 62.5 +/- 0.1 and 100 +/- 36 microg ml(-1), respectively. Carvacrol, thymol, p-cymene, 1,8-cineole, limonene, and beta-pinene were the major components, most often identified in the 11 plant extracts of essential oils. Time-kill curve assays demonstrated the bacteriostatic activity of these essential oils. The essential oils from A. alata and S. glutinosa plants, and the components identified therein, are candidates as potential phytotherapeutic agents for human tuberculosis control.
The antibacterial effect of Ziziphora clinopodioides essential oil and nisinagainst Salmonella typhimurium and Staphylococcus aureus in doogh, a yoghurt-based Iranian drink.

PubMed

Shahbazi, Yasser

2016-01-01

Doogh is the most popular and commonly consumed yoghurt-based Iranian drink. The aim of this study was to investigate the antibacterial effects of Ziziphora clinopodioides essential oil (ZEO) at 0.10 and 0.20% concentrations, nisin at 250 and 500 IU mL -1 , and their combination against Salmonella typhimurium and Staphylococcus aureus in doogh during storage at 4 ˚C for 9 days. Nine batches were studied as follows: control: no ZEO or nisin added, A: 0.10% ZEO, B: 0.20% ZEO, C: 250 IU mL -1 nisin, D: 500 IU mL -1 nisin, E: 0.10% ZEO + 250 IU mL -1 nisin, F: 0.10% ZEO + 500 IU mL -1 nisin, G: 0.20% ZEO + 250 IU mL -1 nisin and H: 0.20% ZEO + 500 IU mL -1 nisin. Based on gas-chromatography and mass spectrometry, carvacrol (65.22%), thymol (19.51%), p -cymene (4.86%) and ɣ -terpinene (4.63%) were the major components of ZEO. The populations of S. typhimurium and S. aureus in samples treated with all concentrations of the ZEO and nisin were kept below 1 log CFU mL -1 on day 5 of storage, while the count of S . typhimurium and S. aureus was found as 2.72 ± 0.02 and 2.21 ± 0.00 log CFU mL -1 on day 5 for untreated samples, respectively. The ZEO separately and in combination with nisin, was very effective against these two common food-borne pathogens. The ZEO alone and in combination with nisin could be considered as a potential strong antimicrobial agent that can be used for the growth inhibition of aforementioned bacteria in food products especially doogh.
Quantification of urinary uric acid in the presence of thymol and thimerosal by high-performance liquid chromatography

NASA Technical Reports Server (NTRS)

Chen, Y.; Pietrzyk, R. A.; Whitson, P. A.

1997-01-01

A high-performance liquid chromatographic method was developed as an alternative to automated enzymatic analysis of uric acid in human urine preserved with thymol and/or thimerosal. Uric acid (tR = 10 min) and creatinine (tR = 5 min) were separated and quantified during isocratic elution (0.025 M acetate buffer, pH 4.5) from a mu Bondapak C18 column. The uric-acid peak was identified chemically by incubating urine samples with uricase. The thymol/thimerosal peak appeared at 31 min during the washing step and did not interfere with the analysis. We validated the high-performance liquid chromatographic method for linearity, precision and accuracy, and the results were found to be excellent.
Pharmacological Properties and Molecular Mechanisms of Thymol: Prospects for Its Therapeutic Potential and Pharmaceutical Development

PubMed Central

Nagoor Meeran, Mohamed Fizur; Javed, Hayate; Al Taee, Hasan; Azimullah, Sheikh; Ojha, Shreesh K.

2017-01-01

Thymol, chemically known as 2-isopropyl-5-methylphenol is a colorless crystalline monoterpene phenol. It is one of the most important dietary constituents in thyme species. For centuries, it has been used in traditional medicine and has been shown to possess various pharmacological properties including antioxidant, free radical scavenging, anti-inflammatory, analgesic, antispasmodic, antibacterial, antifungal, antiseptic and antitumor activities. The present article presents a detailed review of the scientific literature which reveals the pharmacological properties of thymol and its multiple therapeutic actions against various cardiovascular, neurological, rheumatological, gastrointestinal, metabolic and malignant diseases at both biochemical and molecular levels. The noteworthy effects of thymol are largely attributed to its anti-inflammatory (via inhibiting recruitment of cytokines and chemokines), antioxidant (via scavenging of free radicals, enhancing the endogenous enzymatic and non-enzymatic antioxidants and chelation of metal ions), antihyperlipidemic (via increasing the levels of high density lipoprotein cholesterol and decreasing the levels of low density lipoprotein cholesterol and low density lipoprotein cholesterol in the circulation and membrane stabilization) (via maintaining ionic homeostasis) effects. This review presents an overview of the current in vitro and in vivo data supporting thymol’s therapeutic activity and the challenges concerning its use for prevention and its therapeutic value as a dietary supplement or as a pharmacological agent or as an adjuvant along with current therapeutic agents for the treatment of various diseases. It is one of the potential candidates of natural origin that has shown promising therapeutic potential, pharmacological properties and molecular mechanisms as well as pharmacokinetic properties for the pharmaceutical development of thymol. PMID:28694777
Enhancement of orofacial antinociceptive effect of carvacrol, a monoterpene present in oregano and thyme oils, by β-cyclodextrin inclusion complex in mice.

PubMed

Silva, Juliane C; Almeida, Jackson R G S; Quintans, Jullyana S S; Gopalsamy, Rajiv Gandhi; Shanmugam, Saravanan; Serafini, Mairim Russo; Oliveira, Maria R C; Silva, Bruno A F; Martins, Anita O B P B; Castro, Fyama F; Menezes, Irwin R A; Coutinho, Henrique D M; Oliveira, Rita C M; Thangaraj, Parimelazhagan; Araújo, Adriano A S; Quintans-Júnior, Lucindo J

2016-12-01

Orofacial pain is associated with diagnosis of chronic pain of head, face, mouth, neck and all the intraoral structures. Carvacrol, a naturally occurring isoprenoid with diverse class of biological activities including anti-inflammatory, analgesic, antitumor and antioxidant properties. Now, the antinociceptive effect was studied in mice pretreatment with carvacrol (CARV) and β-cyclodextrin complex containing carvacrol (CARV-βCD) in formalin-, capsaicin-, and glutamate- induced orofacial nociception. Mice were pretreated with vehicle (0.9% Nacl, p.o.), CARV (10 and 20mg/kg, p.o.), CARV-βCD (10 and 20mg/kg, p.o.) or MOR (10mg/kg, i.p.) before the nociceptive behavior induced by subcutaneous injections (s.c.) of formalin (20μl, 2%), capsaicin (20μl, 2.5μg) or glutamate (20μl, 25μM) into the upper lip respectively. The interference on motor coordination was determined using rotarod and grip strength meter apparatus. CARV-βCD reduced the nociceptive during the two phases of the formalin test, whereas CARV did not produced the reduction in face-rubbing behavior in the initial phase. CARV-βCD (20mg/kg, p.o.) produced 49.3% behavior pain while CARV alone at 20mg/kg, p.o, produced 28.7% of analgesic inhibition in the second phase of formalin test. CARV, CARV-βCD and Morphine (MOR) showed a significant reduction against nociception caused by capsaicin or glutamate injection. Thus the encapsulation of carvacrol in β-cyclodextrin can acts as a considerable therapeutic agent with pharmacological interest for the orofacial pain management. Copyright © 2016 Elsevier Masson SAS. All rights reserved.
Soil microorganisms alleviate the allelochemical effects of a thyme monoterpene on the performance of an associated grass species.

PubMed

Ehlers, Bodil K

2011-01-01

Plant allelochemicals released into the soil can significantly impact the performance of associated plant species thereby affecting their competitive ability. Soil microbes can potentially affect the interaction between plant and plant chemicals by degrading the allelochemicals. However, most often plant-plant chemical interactions are studied using filter paper bioassays examining the pair-wise interaction between a plant and a plant chemical, not taking into account the potential role of soil microorganisms. To explore if the allelopathic effects on a grass by the common thyme monoterpene "carvacrol" are affected by soil microorganisms. Seedlings of the grass Agrostis capillaris originating from 3 different thyme sites were raised in the greenhouse. Seedlings were grown under four different soil treatments in a 2*2 fully factorial experiment. The monoterpene carvacrol was either added to standard greenhouse soil or left out, and soil was either sterilized (no soil microorganisms) or not (soil microorganisms present in soil). The presence of carvacrol in the soil strongly increased mortality of Agrostis plants, and this increase was highest on sterile soil. Plant biomass was reduced on soil amended with carvacrol, but only when the soil was also sterilized. Plants originating from sites where thyme produces essential oils containing mostly carvacrol had higher survival on soil treated with that monoterpene than plants originating from a site where thyme produced different types of terpenes, suggesting an adaptive response to the locally occurring terpene. The study shows that presence of soil microorganisms can alleviate the negative effect of a common thyme monoterpene on the performance of an associated plant species, emphasizing the role of soil microbes in modulating plant-plant chemical interactions.
Antibacterial activity of essential oil components and their potential use in seed disinfection.

PubMed

Lo Cantore, Pietro; Shanmugaiah, Vellasamy; Iacobellis, Nicola Sante

2009-10-28

Among the main (> or = 0.7%) components of some essential oils, considerable antibacterial activity was shown by terpenoid and phenylpropanoid derivatives containing phenol and alcohol functionalities. A reduced or no activity was shown by those derivatives containing ketones, aldehydes, ethers, and ester functionalities as well as the remaining terpenoids. Eugenol emulsion treatments (1-8 mg/mL) of bean seeds bearing about 2.6 x 10(6) cfu/seed of strain ICMP239 of Xanthomonas campestris pv. phaseoli var. fuscans determined a highly significant reduction of the bacteria on seeds. In particular, eugenol at 4 mg/mL disinfect seeds bearing about 7.0 x 10(2) cfu/seed and lower densities. However, after 72 h, incubation treatments with 2, 4, and 8 mg/mL of eugenol caused germination reduction of 3%, 7%, and 16%, respectively, which was significantly different from the controls. No effect on germination was observed with 1 mg/mL eugenol emulsion treatment. These data indicate eugenol as potentially useful for bean seed disinfection from X. campestris pv. phaseoli var. fuscans. Further studies on the effects on seed vitality and on formulation of essential oils are needed.
Eugenol and its structural analogs inhibit monoamine oxidase A and exhibit antidepressant-like activity.

PubMed

Tao, Guoxin; Irie, Yoshifumi; Li, Dian-Jun; Keung, Wing Ming

2005-08-01

Eugenol (1) is an active principle of Rhizoma acori graminei, a medicinal herb used in Asia for the treatment of symptoms reminiscent of Alzheimer's disease (AD). It has been shown to protect neuronal cells from the cytotoxic effect of amyloid beta peptides (Abetas) in cell cultures and exhibit antidepressant-like activity in mice. Results from this study show that eugenol inhibits monoamine oxidase A (MAOA) preferentially with a K(i)=26 microM. It also inhibits MAOB but at much higher concentrations (K(i)=211 microM). In both cases, inhibition is competitive with respect to the monoamine substrate. Survey of compounds structurally related to eugenol has identified a few that inhibit MAOs more potently. Structure activity relationship reveals structural features important for MAOA and MAOB inhibition. Molecular docking experiments were performed to help explain the SAR outcomes. Four of these compounds, two (1, 24) inhibiting MAOA selectively and the other two (19, 21) inhibiting neither MAOA nor MAOB, were tested for antidepressant-like activity using the forced swim test in mice. Results suggest a potential link between the antidepressant activity of eugenol and its MAOA inhibitory activity.
[Treatment of cough in respiratory tract infections - the effect of combining the natural active compounds with thymol].

PubMed

Schönknecht, Karina; Krauss, Hanna; Jambor, Jerzy; Fal, Andrzej M

Cough is one of the characteristic symptoms of upper respiratory tract infections (URI). Herbal medicines are often used in the treatment of the cough associated with infection and to accelerate recovery or support the immune system. An example of such products are extracts of thyme and primrose, and also their combination with thymol. Thymus vulgaris is a spasmolytic, antimicrobial, anti-inflammatory, immunomodulatory and antioxidant agent. The most important component responsible for the activity of thyme is thymol contained in the volatile thyme oil. Primrose is, most of all, a saponine agent with expectorant and secretolytic activity, showing also spasmolytic, anti-inflammatory and antimicrobial effects. Because of the additive effects of the mentioned extracts and their wide activity profile they are often used as a combination drug. The use of this combination was assessed in the URI with the effects of alleviation of cough and dyspnea, and shortening the length of the disease. The effectiveness of the drug containing the extracts of thyme and primrose with the addition of thymol (Bronchosol®) was comparable to synthetic ambroxol and its safety has been proved. Moreover, the in-vitro antibacterial and antifungal effects of this drug have been evaluated.
Inhibitory Effect of Cinnamaldehyde, Citral, and Eugenol on Aflatoxin Biosynthetic Gene Expression and Aflatoxin B1 Biosynthesis in Aspergillus flavus.

PubMed

Liang, Dandan; Xing, Fuguo; Selvaraj, Jonathan Nimal; Liu, Xiao; Wang, Limin; Hua, Huijuan; Zhou, Lu; Zhao, Yueju; Wang, Yan; Liu, Yang

2015-12-01

In order to reveal the inhibitory effects of cinnamaldehyde, citral, and eugenol on aflatoxin biosynthesis, the expression levels of 5 key aflatoxin biosynthetic genes were evaluated by real-time PCR. Aspergillus flavus growth and AFB1 production were completely inhibited by 0.80 mmol/L of cinnamaldehyde and 2.80 mmol/L of citral. However, at lower concentration, cinnamaldehyde (0.40 mmol/L), eugenol (0.80 mmol/L), and citral (0.56 mmol/L) significantly reduced AFB1 production with inhibition rate of 68.9%, 95.4%, and 41.8%, respectively, while no effect on fungal growth. Real-time PCR showed that the expressions of aflR, aflT, aflD, aflM, and aflP were down-regulated by cinnamaldehyde (0.40 mmol/L), eugenol (0.80 mmol/L), and citral (0.56 mmol/L). In the presence of cinnamaldehyde, AflM was highly down-regulated (average of 5963 folds), followed by aflP, aflR, aflD, and aflT with the average folds of 55, 18, 6.5, and 5.8, respectively. With 0.80 mmol/L of eugenol, aflP was highly down-regulated (average of 2061-folds), followed by aflM, aflR, aflD, and aflT with average of 138-, 15-, 5.2-, and 4.8-folds reduction, respectively. With 0.56 mmol/L of citral, aflT was completely inhibited, followed by aflM, aflP, aflR, and aflD with average of 257-, 29-, 3.5-, and 2.5-folds reduction, respectively. These results suggest that the reduction in AFB1 production by cinnamaldehyde, eugenol, and citral at low concentration may be due to the down-regulations of the transcription level of aflatoxin biosynthetic genes. Cinnamaldehyde and eugenol may be employed successfully as a good candidate in controlling of toxigenic fungi and subsequently contamination with aflatoxins in practice. © 2015 Institute of Food Technologists®
Basic emotions evoked by eugenol odor differ according to the dental experience. A neurovegetative analysis.

PubMed

Robin, O; Alaoui-Ismaïli, O; Dittmar, A; Vernet-Maury, E

1999-06-01

Subjective individual experiences seem to indicate that odors may form strong connections with memories, especially those charged with emotional significance. In the dental field, this could be the case with the odorant eugenol, responsible for the typical clinging odor impregnating the dental office. The odor of eugenol could evoke memories of unpleasant dental experiences and, therefore, negative feelings such as anxiety and fear, since eugenates (cements containing eugenol) are used in potentially painful restorative dentistry. This hypothesis was tested by evaluating the emotional impact of the odor of eugenol through autonomic nervous system (ANS) analysis. The simultaneous variations of six ANS parameters (two electrodermal, two thermovascular and two cardiorespiratory), induced by the inhalation of this odorant, were recorded on volunteer subjects. Vanillin (a pleasant odorant) and propionic acid (an unpleasant one) served as controls. After the experiment, subjects were asked to rate the pleasantness versus unpleasantness of each odorant on an 11-point hedonic scale. The patterns of autonomic responses, obtained for each odorant and each subject, were transcribed into one of the six basic emotions defined by Ekman et al. (happiness, surprise, sadness, fear, anger and disgust). Results were compared between two groups of subjects divided according to their dental experience (fearful and non-fearful dental care subjects) and showed significant differences only for eugenol. This odorant was rated as pleasant by non-fearful dental subjects but unpleasant by fearful dental subjects. The evoked autonomic responses were mainly associated with positive basic emotions (happiness and surprise) in non-fearful dental subjects and with negative basic emotions (fear, anger, disgust) in fearful dental subjects. These results suggest that eugenol can be responsible for different emotional states depending on the subjects' dental experience, which seems to confirm the potential role of odors as elicitors of emotional memories. This study also supports the possible influence of the ambient odor impregnating the dental office, strengthening a negative conditioning toward dental care in some anxious patients.
Critical Synergistic Concentration of Lecithin Phospholipids Improves the Antimicrobial Activity of Eugenol against Escherichia coli

PubMed Central

Zhang, Haoshu; Dudley, Edward G.

2017-01-01

ABSTRACT In this study, the effect of individual lecithin phospholipids on the antimicrobial properties of eugenol against Escherichia coli C600 was investigated. We tested five major phospholipids common in soy or egg lecithin (1,2-dihexadecanoyl-sn-glycero-3-phosphocholine [DPPC], 1,2-dioctadecanoyl-sn-glycero-3-phosphocholine [DSPC], 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine [DPPE], 1,2-dihexadecanoyl-sn-glycero-3-phosphate [sodium salt] [DPPA], and 1,2-dihexadecanoyl-sn-glycero-3-phospho-l-serine [DPPS]) and one synthetic cationic phospholipid (1,2-dioctadecanoyl-sn-glycero-3-ethylphosphocholine [18:0 EPC]). Among the six phospholipids, DPPC, DSPC, DPPE, DPPA, and the cationic 18:0 EPC showed critical synergistic concentrations that significantly improved the inactivation effect of eugenol against E. coli after 30 min of exposure. At the critical synergistic concentration, an additional ca. 0.4 to 1.9 log reduction (ca. 0.66 to 2.17 log CFU/ml reduction) in the microbial population was observed compared to eugenol-only (control) treatments (ca. 0.25 log reduction). In all cases, increasing the phospholipid amount above the critical synergistic concentration (which was different for each phospholipid) resulted in antimicrobial properties similar to those seen with the eugenol-only (control) treatments. DPPS did not affect the antimicrobial properties of eugenol at the tested concentrations. The critical synergistic concentration of phospholipids was correlated with their critical micelle concentrations (CMC). IMPORTANCE Essential oils (EOs) are naturally occurring antimicrobials, with limited use in food due to their hydrophobicity and strong aroma. Lecithin is used as a natural emulsifier to stabilize EOs in aqueous systems. We previously demonstrated that, within a narrow critical-concentration window, lecithin can synergistically enhance the antimicrobial properties of eugenol. Since lecithin is a mixture of different phospholipids, we aimed to identify which phospholipids are crucial for the observed synergistic effect. This research studied the bioactivity of lecithin phospholipids, contributing to a rational design in using lecithin to effectively control foodborne pathogens in foods. PMID:28842540
Eugenol Nanoemulsion Stabilized with Zein and Sodium Caseinate by Self-Assembly.

PubMed

Wang, Lei; Zhang, Yue

2017-03-31

Eugenol-loaded nanoemulsion by zein and sodium caseinate (NaCas) was prepared without using specific equipment or organic solvents. The deprotonated eugenol in hot alkaline was added to NaCas/zein mixtures with different mass ratios at pH 11.5 and then neutralized to pH 7.0. The nanoemulsions showed a well-defined diameter (around 109-139 nm) and a negative surface potential (from -28.5 to -35.8 mV) with spherical morphology. The entrapment efficiency (EE) of 1% (v/v) eugenol reached 84.24% by 2% (m/v) NaCas/zein at a mass ratio of 1:1. This formulation also showed the narrowest size distribution and extraordinary stability during ambient storage (22 °C) up to 30 days and retained good redispersibility after spray- or freeze-drying. The current study showed a promising clean and low-cost strategy to deliver lipophilic compounds containing the hydroxyl group.
Plant terpenoids: acute toxicities and effects on flight motor activity and wing beat frequency in the blow fly Phaenicia sericata.

PubMed

Waliwitiya, Ranil; Belton, Peter; Nicholson, Russell A; Lowenberger, Carl A

2012-02-01

We evaluated the acute toxicities and the physiological effects of plant monoterpenoids (eugenol, pulegone, citronellal and alpha-terpineol) and neuroactive insecticides (malathion, dieldrin and RH3421) on flight muscle impulses (FMI) and wing beat signals (WBS) of the blow fly (Phaenicia sericata). Topically-applied eugenol, pulegone, citronellal, and alpha-terpineol produced neurotoxic symptoms, but were less toxic than malathion, dieldrin, or RH3421. Topical application of eugenol, pulegone, and citronellal reduced spike amplitude in one of the two banks of blow fly dorsolongitudinal flight muscles within 6-8 min, but with citronellal, the amplitude of FMIs reverted to a normal pattern within 1 hr. In contrast to pulegone and citronellal, where impulse frequency remained relatively constant, eugenol caused a gradual increase, then a decline in the frequency of spikes in each muscle bank. Wing beating was blocked permanently within 6-7 min of administering pulegone or citronellal and within 16 mins with eugenol. alpha-Terpineol-treated blow flies could not beat their wings despite normal FMI patterns. The actions of these monoterpenoids on blow fly flight motor patterns are discussed and compared with those of dieldrin, malathion, RH3421, and a variety of other neuroactive substances we have previously investigated in this system. Eugenol, pulegone and citronellal readily penetrate blow fly cuticle and interfere with flight muscle and/or central nervous function. Although there were differences in the effects of these compounds, they mainly depressed flight-associated responses, and acted similarly to compounds that block sodium channels and facilitate GABA action.
Biological monitoring of environment exposure to safrole and the Taiwanese betel quid chewing.

PubMed

Chang, M J W; Ko, C Y; Lin, R F; Hsieh, L L

2002-11-01

A rapid and sensitive biological monitoring (BM) method for assessing exposure to the environmental carcinogen safrole has been developed. The method is an isocratic high-performance liquid chromatographic (HPLC) analysis of urinary dihydroxychavicol (DHAB) and eugenol, the urinary metabolites of safrole. Good linearity, precision, and accuracy were demonstrated. A recovery of 98.8 +/- 5.4% (SD, n = 3) was found for DHAB and 84.1 +/- 3.4% (n = 3) for eugenol. The quantitation limits of the method were 8 ng for DHAB and 10 ng for eugenol. The validity of the method was demonstrated by a linear dose-response relationship observed in rats given oral doses of safrole at 30, 75, and 150 mg/kg body weight. The method was also used to monitor the environmental exposure to the Taiwanese betel quid (TBQ) chewing, because TBQ used in Taiwan not only contains areca (betel) nut, slaked lime, and catechu but also Piper betle inflorescence or its leaves. Both of the latter have a high content of safrole. The feasibility of the method to monitor TBQ chewing was demonstrated by an analysis of 153 spot human urine samples. The results showed that the p value of the nonparametric group comparison was < 0.001 for DHAB and 0.832 for eugenol. The TBQ chewers also exhibited a significantly higher rate of urinary DHAB (but not eugenol) than the nonchewers with an odd ratio of 3.47 (95% CI, 1.61-7.51). However, when only the eugenol-positive subjects were taken into analysis, the ratio rose to 24.38 (95% CI, 3.00-197.90).
Evidence for Lack of Acquisition of Tolerance in Salmonella enterica Serovar Typhimurium ATCC 14028 after Exposure to Subinhibitory Amounts of Origanum vulgare L. Essential Oil and Carvacrol

PubMed Central

Luz, Isabelle da Silva; Gomes Neto, Nelson Justino; Tavares, Adassa Gama; Nunes, Pollyana Campos; Magnani, Marciane

2012-01-01

Overnight exposure of Salmonella enterica serovar Typhimurium to sublethal amounts of Origanum vulgare essential oil (OV) and carvacrol (CAR) did not result in direct and cross-bacterial protection. Cells subcultured with increasing amounts of OV or CAR survived up to the MIC of either compound, revealing few significant changes in bacterial susceptibility. PMID:22544235

Combined action of nisin and carvacrol on Bacillus cereus and Listeria monocytogenes.

PubMed

Pol, I E; Smid, E J

1999-09-01

Nisin, a small antimicrobial protein, was tested for its bactericidal action against Listeria monocytogenes and Bacillus cereus and a typical biphasic reduction of the viable count was observed. The reduction was most fast during the first 10 min of exposure, while the viable count remained stable in the last part of the exposure period. Bacillus cereus was more sensitive towards nisin than L. monocytogenes and the inhibitory effect of nisin was stronger towards cells cultivated and exposed at 8 degrees C than towards cells cultivated and exposed at 20 degrees C. Combining nisin with sublethal doses of carvacrol resulted in an increased reduction in the viable count of both organisms, indicating synergy between nisin and carvacrol. Addition of lysozyme as a third preservative factor increased the synergistic effect between nisin and carvone, especially in the last part of the exposure period.
Combined effect of carnosol, rosmarinic acid and thymol on the oxidative stability of soybean oil using a simplex centroid mixture design.

PubMed

Saoudi, Salma; Chammem, Nadia; Sifaoui, Ines; Jiménez, Ignacio A; Lorenzo-Morales, Jacob; Piñero, José E; Bouassida-Beji, Maha; Hamdi, Moktar; L Bazzocchi, Isabel

2017-08-01

Oxidation taking place during the use of oil leads to the deterioration of both nutritional and sensorial qualities. Natural antioxidants from herbs and plants are rich in phenolic compounds and could therefore be more efficient than synthetic ones in preventing lipid oxidation reactions. This study was aimed at the valorization of Tunisian aromatic plants and their active compounds as new sources of natural antioxidant preventing oil oxidation. Carnosol, rosmarinic acid and thymol were isolated from Rosmarinus officinalis and Thymus capitatus by column chromatography and were analyzed by nuclear magnetic resonance. Their antioxidant activities were measured by DPPH, ABTS and FRAP assays. These active compounds were added to soybean oil in different proportions using a simplex-centroid mixture design. Antioxidant activity and oxidative stability of oils were determined before and after 20 days of accelerated oxidation at 60 °C. Results showed that bioactive compounds are effective in maintaining oxidative stability of soybean oil. However, the binary interaction of rosmarinic acid and thymol caused a reduction in antioxidant activity and oxidative stability of soybean oil. Optimum conditions for maximum antioxidant activity and oxidative stability were found to be an equal ternary mixture of carnosol, rosmarinic acid and thymol. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.
Preliminary evaluation of antimicrobial activity of some chemicals on in vitro apple shoots infected by 'Candidatus Phytoplasma mali'.

PubMed

Aldaghi, M; Massart, S; Druart, Ph; Bertaccini, A; Jijakli, M H; Lepoivre, P

2008-01-01

Phytoplasmas are associated with several hundred plant diseases worldwide, including numerous ones with important economical impact. Control of epidemic outbreak of phytoplasma diseases can be theoretically carried out by antibiotics. However, they are expensive, not allowed or prohibited in several countries, and even not always efficient. Presently, effective but safe antimicrobial agents are needed to control severe phytoplasma diseases in field. The aim of the present study was to evaluate the susceptibility of 'Candidatus Phytoplasma mali' to several chemical or synthetic antimicrobial agents. We tested nisin, esculetin, pyrithione and chloramphenicol as molecules having different target activities against micro-organisms. Because of their antimicrobial properties against fungi and bacteria, 4 phyto-essential oils (carvacrol, eugenol, terpineol, alpha-pinene) had also been tested. The activity of these molecules was compared with two antibiotics (tetracycline and enrofloxacin) used as control products. All these compounds were tested in in vitro culture of apples (MM106) infected by 'Ca. P. mall'. All compounds were added to the proliferation medium (modified MS) after autoclaving at 3 concentrations (100, 500, 1,000 ppm), except nisin and pyrithione which were tested at 10, 100 and 500 ppm. Phytoplasma infection was quantified in plant materials by real-time PCR before their transfer and after one or two months of culture in the presence of antimicrobial agents. Primary results showed that phytoplasma were not detectable after one and two months in the presence of pyrithione (at 10 and 100 ppm). Moreover, some other products reduced the concentration of phytoplasma after two months. Shoots died or withered on media enriched with essential oils; that made them impossible to assess, especially when they were used at concentration of 500 and 1,000 ppm.
Inactivation of Staphylococcus aureus in Oat and Soya Drinks by Enterocin AS-48 in Combination with Other Antimicrobials.

PubMed

Burgos, María José Grande; Aguayo, M Carmen López; Pulido, Rubén Pérez; Gálvez, Antonio; López, Rosario Lucas

2015-09-01

The presence of toxicogenic Staphylococcus aureus in foods and the dissemination of methicillin-resistant S. aureus (MRSA) in the food chain are matters of concern. In the present study, the circular bacteriocin enterocin AS-48, applied singly or in combination with phenolic compounds (carvacrol, eugenol, geraniol, and citral) or with 2-nitro-1-propanol (2NPOH), was investigated in the control of a cocktail made from 1 methicillin-sensitive and 1 MRSA strains inoculated on commercial oat and soya drinks. Enterocin AS-48 exhibited low bactericidal activity against staphylococci in the drinks investigated when applied singly. The combinations of sub-inhibitory concentrations of enterocin AS-48 (25 μg/mL) and phenolic compounds or 2NPOH caused complete inactivation of staphylococci in the drinks within 24 h of incubation at 22 °C. When tested in oat and soya drinks stored for 7 d at 10 °C, enterocin AS-48 (25 μg/mL) in combination with 2NPOH (5.5 mM) reduced viable counts rapidly in the case of oat drink (4.2 log cycles after 12 h) or slowly in soya drink (3.8 log cycles after 3 d). The same combined treatment applied on drinks stored at 22 °C achieved a fast inactivation of staphylococci within 12 to 24 h in both drinks, and no viable staphylococci were detected for up to 7 d of storage. Results from the study highlight the potential of enterocin AS-48 in combination with 2NPOH for inactivation of staphylococci. © 2015 Institute of Food Technologists®
Critical Concentration of Lecithin Enhances the Antimicrobial Activity of Eugenol against Escherichia coli.

PubMed

Zhang, Haoshu; Dudley, Edward G; Davidson, P Michael; Harte, Federico

2017-04-15

Lecithin is a natural emulsifier used in a wide range of food and nonfood applications to improve physical stability, with no known bioactive effects. In this study, the effect of lecithin on the antimicrobial performance of a constant eugenol concentration was tested against three Escherichia coli strains (C600, 0.1229, and O157:H7 strain ATCC 700728). This is the first study, to our knowledge, focusing on lecithin at concentrations below those commonly used in foods to improve the stability of oil in water emulsions (≤10 mg/100 ml). For all three cultures, significant synergistic antimicrobial effects were observed when E. coli cultures were exposed to a constant eugenol concentration (ranging from 0.043 to 0.050% [wt/wt]) together with critical lecithin concentrations ranging from 0.5 to 1 mg/100 ml. Increasing the concentration of lecithin above 1 mg/100 ml (up to 10 mg/100 ml lecithin) diminished the antibacterial effect to values similar to those with eugenol-only treatments. The formation of aggregates (<100 nm) at the critical lecithin concentration was observed using cryo-transmission electron microscopy (cryo-TEM), together with a reduction in light absorbance at 284 nm. At critically low concentrations of lecithin, the formation of nanoscale aggregates is responsible for improving eugenol antimicrobial effects. IMPORTANCE Essential oils (EOs) are effective natural antimicrobials. However, their hydrophobicity and strong aromatic character limit the use of essential oils in food systems. Emulsifiers (e.g., lecithin) increase the stability of EOs in water-based systems but fail to consistently improve antimicrobial effects. We demonstrate that lecithin, within a narrow critical concentration window, can enhance the antimicrobial properties of eugenol. This study highlights the potential bioactivity of lecithin when utilized to effectively control foodborne pathogens. Copyright © 2017 American Society for Microbiology.
Boll weevil (Coleoptera: Curculionidae) response to and volatilization rates of grandlure when combined with varying doses of eugenol in the extended-life pheromone lure.

PubMed

Armstrong, J S

2010-04-01

Boll weevil, Anthonomus grandis grandis Boheman (Coleoptera: Curculionidae), trapping and pheromone quantitative analysis of extended-life pheromone lures manufactured with 0, 10, 20, and 30 mg of eugenol was conducted in the Rio Grande Valley of Texas under spring and summer conditions. Boll weevils responded positively to eugenol on one of 12 trapping weeks when densities were high, but when densities were low (<2 weevils trap(-1) wk(-1)), there were no significant differences in captures for any dosage of eugenol offered in a standard boll weevil trap. Weekly grandlure volatilization did not differ by eugenol dose but was significantly different when evaluated over three different trapping periods and by week within trapping period due to differences in ambient temperature. The amount of grandlure that remained after 4 wk in moderate temperatures of spring was 13.1 +/- 0.19 mg (55.7% of original 25 mg of content) compared with 5.5 +/- 0.15 mg remaining (22.8% of original 25 mg content) after for 4 wk in summer heat. Weekly volatilization of grandlure for the summer trapping period was 9.8 +/- 0.32 mg for the first week, declining steadily to 1.0 +/- 0.09 mg by the fourth week of age. The data indicate that at high summer temperatures >30 degrees C, accumulative grandlure loss per week may be too high, leaving too little residual grandlure to effectively attract boll weevils at the end of 3 wk of trapping. Eugenol plays no role in reserving or encouraging the release of grandlure, or in increasing boll weevil captures when boll weevil densities are low.
Critical Concentration of Lecithin Enhances the Antimicrobial Activity of Eugenol against Escherichia coli

PubMed Central

Zhang, Haoshu; Dudley, Edward G.; Davidson, P. Michael

2017-01-01

ABSTRACT Lecithin is a natural emulsifier used in a wide range of food and nonfood applications to improve physical stability, with no known bioactive effects. In this study, the effect of lecithin on the antimicrobial performance of a constant eugenol concentration was tested against three Escherichia coli strains (C600, 0.1229, and O157:H7 strain ATCC 700728). This is the first study, to our knowledge, focusing on lecithin at concentrations below those commonly used in foods to improve the stability of oil in water emulsions (≤10 mg/100 ml). For all three cultures, significant synergistic antimicrobial effects were observed when E. coli cultures were exposed to a constant eugenol concentration (ranging from 0.043 to 0.050% [wt/wt]) together with critical lecithin concentrations ranging from 0.5 to 1 mg/100 ml. Increasing the concentration of lecithin above 1 mg/100 ml (up to 10 mg/100 ml lecithin) diminished the antibacterial effect to values similar to those with eugenol-only treatments. The formation of aggregates (<100 nm) at the critical lecithin concentration was observed using cryo-transmission electron microscopy (cryo-TEM), together with a reduction in light absorbance at 284 nm. At critically low concentrations of lecithin, the formation of nanoscale aggregates is responsible for improving eugenol antimicrobial effects. IMPORTANCE Essential oils (EOs) are effective natural antimicrobials. However, their hydrophobicity and strong aromatic character limit the use of essential oils in food systems. Emulsifiers (e.g., lecithin) increase the stability of EOs in water-based systems but fail to consistently improve antimicrobial effects. We demonstrate that lecithin, within a narrow critical concentration window, can enhance the antimicrobial properties of eugenol. This study highlights the potential bioactivity of lecithin when utilized to effectively control foodborne pathogens. PMID:28213539
Effectiveness of a spontaneous carvacrol nanoemulsion against Salmonella enterica Enteritidis and Escherichia coli O157:H7 on contaminated broccoli and radish seeds.

PubMed

Landry, Kyle S; Micheli, Sean; McClements, David Julian; McLandsborough, Lynne

2015-10-01

The incidence of foodborne illness associated with the consumption of fresh produce has continued to increase over the past decade. Sprouts, such as mung bean, alfalfa, radish, and broccoli, are minimally processed and have been sources for foodborne illness. Currently, a 20,000 ppm calcium hypochlorite soak is recommended for the treatment of sprouting seeds. In this study, the efficacy of an antimicrobial carvacrol nanoemulsion was tested against Salmonella enterica subspecies enterica serovar Enteritidis (ATCC BAA-1045) or EGFP expressing Escherichia coli O157:H7 (ATCC 42895) contaminated sprouting seeds. Antimicrobial treatments were performed by soaking inoculated seeds in nanoemulsions (4000 or 8000 ppm) for 30 or 60 min. Following treatment, surviving cells were determined by performing plate counts and/or Most Probable Number (MPN) enumeration. Treated seeds were sprouted and tested for the presence of pathogens. Treatment successfully inactivated low levels (2 and 3 log CFU/g) of S. Enteritidis and E. coli on radish seeds when soaked for 60 min at concentrations ≥4000 (0.4%) ppm carvacrol. This treatment method was not affective on contaminated broccoli seeds. Total sprout yield was not influenced by any treatments. These results show that carvacrol nanoemulsions may be an alternative treatment method for contaminated radish seeds. Copyright © 2015 Elsevier Ltd. All rights reserved.
Anxiolytic-like effect of Carvacrol (5-isopropyl-2-methylphenol) in mice: involvement with GABAergic transmission.

PubMed

Melo, Francisca Helvira Cavalcante; Venâncio, Edith Teles; de Sousa, Damião Pergentino; de França Fonteles, Marta Maria; de Vasconcelos, Silvânia Maria Mendes; Viana, Glauce Socorro Barros; de Sousa, Francisca Cléa Florenço

2010-08-01

Carvacrol (5-isopropyl-2-methylphenol) is a monoterpenic phenol present in the essencial oil of many plants. It is the major component of the essential oil fraction of oregano and thyme. This work presents the behavioral effects of carvacrol in animal models of elevated plus maze (EPM), open field, Rotarod and barbiturate-induced sleeping time tests in mice. Carvacrol (CVC) was administered orally, in male mice, at single doses of 12.5; 25 and 50 mg/kg while diazepam 1 or 2 mg/kg was used as standard drug and flumazenil (2.5 mg/kg) was used to elucidate the possible anxiolytic mechanism of CVC on the plus maze test. The results showed that CVC, at three doses, had no effect on the spontaneous motor activity in the Rotarod test nor in the number of squares crossed in the open-field test. However, CVC decreased the number of groomings in the open-field test. In the plus maze test, CVC, at three doses significantly increased all the observed parameters in the EPM test and flumazenil was able to reverse the effects of diazepam and CVC. Therefore, CVC did not alter the sleep latency and sleeping time in the barbiturate-induced sleeping time test. These results show that CVC presents anxiolytic effects in the plus maze test which are not influenced by the locomotor activity in the open-field test.
Eugenol wash and chitosan based coating reduces Campylobacter jejuni counts on poultry products

USDA-ARS?s Scientific Manuscript database

Campylobacter, a leading cause of foodborne illness globally in humans, is strongly associated with the consumption of contaminated poultry products. Unfortunately, current strategies to reduce Campylobacter counts in poultry have had limited success. Our study investigated the efficacy of eugenol ...
Synthetic scaffolds with full pore interconnectivity for bone regeneration prepared by supercritical foaming using advanced biofunctional plasticizers.

PubMed

Salerno, Aurelio; Diéguez, Sara; Diaz-Gomez, Luis; Gómez-Amoza, José L; Magariños, Beatriz; Concheiro, Angel; Domingo, Concepción; Alvarez-Lorenzo, Carmen; García-González, Carlos A

2017-06-30

Supercritical foaming allows for the solvent-free processing of synthetic scaffolds for bone regeneration. However, the control on the pore interconnectivity and throat pore size with this technique still needs to be improved. The use of plasticizers may help overcome these limitations. Eugenol, a GRAS natural compound extracted from plants, is proposed in this work as an advanced plasticizer with bioactive properties. Eugenol-containing poly(ε-caprolactone) (PCL) scaffolds were obtained by supercritical foaming (20.0 MPa, 45 °C, 17 h) followed by a one or a two-step depressurization profile. The effects of the eugenol content and the depressurization profile on the porous structure of the material and the physicochemical properties of the scaffold were evaluated. The combination of both processing parameters was successful to simultaneously tune the pore interconnectivity and throat sizes to allow mesenchymal stem cells infiltration. Scaffolds with eugenol were cytocompatible, presented antimicrobial activity preventing the attachment of Gram positive (S. aureus, S. epidermidis) bacteria and showed good tissue integration.
Determination of the exposure parameters that maximise the concentrations of the anaesthetic/sedative eugenol in rainbow trout (Oncorhynchus mykiss) skin-on fillet tissue.

PubMed

Meinertz, J R; Porcher, S T; Smerud, J R; Gaikowski, M P

2014-01-01

Studies were conducted to determine the anaesthetic/sedative concentrations and durations that would maximise anaesthetic/sedative residue concentrations in rainbow trout (Oncorhynchus mykiss) skin-on fillet tissue. Rainbow trout (167-404 g) were exposed to 50 mg l(-1) AQUI-S(®) 20E (10% active ingredient, eugenol) in 17°C freshwater for durations up to 1440 min, 100 and 250 mg l(-1) AQUI-S(®) 20E for durations up to 240 min, and 500 and 1000 mg l(-1) AQUI-S(®) 20E for durations up to 90 min. Fish exposed to 100 mg l(-1) AQUI-S(®) 20E for durations of 30, 60, 120 and 240 min had the greatest eugenol concentrations in the fillet tissue, 50, 58, 54 and 62 µg g(-1), respectively. All other exposure concentrations and durations resulted in significantly lower eugenol concentrations, i.e. all < 39 µg g(-1).
Determination of the exposure parameters that maximise the concentrations of the anaesthetic/sedative eugenol in rainbow trout (Oncorhynchus mykiss) skin-on fillet tissue

USGS Publications Warehouse

Meinertz, Jeffery R.; Porcher, Scott T.; Smerud, Justin R.

2014-01-01

Studies were conducted to determine the anaesthetic/sedative concentrations and durations that would maximize anaesthetic/sedative residue concentrations in rainbow trout (Oncorhynchus mykiss) skin-on fillet tissue. Rainbow trout (167–404 g) were exposed to 50 mg l−1 AQUI-S® 20E (10% active ingredient, eugenol) in 17°C freshwater for durations up to 1440 min, 100 and 250 mg l−1 AQUI-S® 20E for durations up to 240 min, and 500 and 1000 mg l−1 AQUI-S® 20E for durations up to 90 min. Fish exposed to 100 mg l−1 AQUI-S® 20E for durations of 30, 60, 120 and 240 min had the greatest eugenol concentrations in the fillet tissue, 50, 58, 54 and 62 µg g−1, respectively. All other exposure concentrations and durations resulted in significantly lower eugenol concentrations, i.e. all −1.
Isolation of Bioactive Compounds That Relate to the Anti-Platelet Activity of Cymbopogon ambiguus

PubMed Central

Grice, I. Darren; Rogers, Kelly L.; Griffiths, Lyn R.

2011-01-01

Infusions and decoctions of Cymbopogon ambiguus have been used traditionally in Australia for the treatment of headache, chest infections and muscle cramps. The aim of the present study was to screen and identify bioactive compounds from C. ambiguus that could explain this plant's anti-headache activity. A dichloromethane extract of C. ambiguus was identified as having activity in adenosine-diphosphate-induced human platelet aggregation and serotonin-release inhibition bioassays. Subsequent fractionation of this extract led to the isolation of four phenylpropenoids, eugenol, elemicin, eugenol methylether and trans-isoelemicin. While both eugenol and elemicin exhibited dose-dependent inhibition of ADP-induced human platelet serotonin release, only eugenol displayed potent inhibitory activity with an IC50 value of 46.6 μM, in comparison to aspirin, with an IC50 value of 46.1 μM. These findings provide evidence to support the therapeutic efficacy of C. ambiguus in the non-conventional treatment of headache and inflammatory conditions. PMID:20047890
Preparation and characterization of clove essential oil-loaded liposomes.

PubMed

Sebaaly, Carine; Jraij, Alia; Fessi, Hatem; Charcosset, Catherine; Greige-Gerges, Hélène

2015-07-01

In this study, suitable formulations of natural soybean phospholipid vesicles were developed to improve the stability of clove essential oil and its main component, eugenol. Using an ethanol injection method, saturated (Phospholipon 80H, Phospholipon 90H) and unsaturated soybean (Lipoid S100) phospholipids, in combination with cholesterol, were used to prepare liposomes at various eugenol and clove essential oil concentrations. Liposomal batches were characterized and compared for their size, polydispersity index, Zeta potential, loading rate, encapsulation efficiency and morphology. The liposomes were tested for their stability after storing them for 2 months at 4°C by monitoring changes in their mean size, polydispersity index and encapsulation efficiency (EE) values. It was found that liposomes exhibited nanometric oligolamellar and spherical shaped vesicles and protected eugenol from degradation induced by UV exposure; they also maintained the DPPH-scavenging activity of free eugenol. Liposomes constitute a suitable system for encapsulation of volatile unstable essential oil constituents. Copyright © 2015 Elsevier Ltd. All rights reserved.
Critical Synergistic Concentration of Lecithin Phospholipids Improves the Antimicrobial Activity of Eugenol against Escherichia coli.

PubMed

Zhang, Haoshu; Dudley, Edward G; Harte, Federico

2017-11-01

In this study, the effect of individual lecithin phospholipids on the antimicrobial properties of eugenol against Escherichia coli C600 was investigated. We tested five major phospholipids common in soy or egg lecithin (1,2-dihexadecanoyl-sn-glycero-3-phosphocholine [DPPC], 1,2-dioctadecanoyl-sn-glycero-3-phosphocholine [DSPC], 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine [DPPE], 1,2-dihexadecanoyl-sn-glycero-3-phosphate [sodium salt] [DPPA], and 1,2-dihexadecanoyl-sn-glycero-3-phospho-l-serine [DPPS]) and one synthetic cationic phospholipid (1,2-dioctadecanoyl-sn-glycero-3-ethylphosphocholine [18:0 EPC]). Among the six phospholipids, DPPC, DSPC, DPPE, DPPA, and the cationic 18:0 EPC showed critical synergistic concentrations that significantly improved the inactivation effect of eugenol against E. coli after 30 min of exposure. At the critical synergistic concentration, an additional ca. 0.4 to 1.9 log reduction (ca. 0.66 to 2.17 log CFU/ml reduction) in the microbial population was observed compared to eugenol-only (control) treatments (ca. 0.25 log reduction). In all cases, increasing the phospholipid amount above the critical synergistic concentration (which was different for each phospholipid) resulted in antimicrobial properties similar to those seen with the eugenol-only (control) treatments. DPPS did not affect the antimicrobial properties of eugenol at the tested concentrations. The critical synergistic concentration of phospholipids was correlated with their critical micelle concentrations (CMC). IMPORTANCE Essential oils (EOs) are naturally occurring antimicrobials, with limited use in food due to their hydrophobicity and strong aroma. Lecithin is used as a natural emulsifier to stabilize EOs in aqueous systems. We previously demonstrated that, within a narrow critical-concentration window, lecithin can synergistically enhance the antimicrobial properties of eugenol. Since lecithin is a mixture of different phospholipids, we aimed to identify which phospholipids are crucial for the observed synergistic effect. This research studied the bioactivity of lecithin phospholipids, contributing to a rational design in using lecithin to effectively control foodborne pathogens in foods. Copyright © 2017 American Society for Microbiology.
Gastroprotective activity of essential oil of the Syzygium aromaticum and its major component eugenol in different animal models.

PubMed

Santin, José Roberto; Lemos, Marivane; Klein-Júnior, Luiz Carlos; Machado, Isabel Daufenback; Costa, Philipe; de Oliveira, Ana Paula; Tilia, Crislaine; de Souza, Juliana Paula; de Sousa, João Paulo Barreto; Bastos, Jairo Kenupp; de Andrade, Sérgio Faloni

2011-02-01

Syzygium aromaticum, a medicinal plant commonly known as clove, is used to treat toothache, respiratory disorders, inflammation, and gastrointestinal disorders. From the flower buds of S. aromaticum, it is possible to obtain an essential oil comprised of a mixture of aliphatic and cyclic volatile terpenes and phenylpropanoids, being eugenol as the main component. The aims of this study were: (1) to extract the essential oil of the flower buds of S. aromaticum, (2) to identify and quantify the main component of the essential oil, and (3) to evaluate its antiulcer activity using different animal models. Assays were performed using the following protocols in rats: indomethacin-induced and ethanol/HCl-induced ulcer model. Both essential oils from S. aromaticum and eugenol displayed antiulcer activities in the rat models of indomethacin- and ethanol-induced ulcer. Studies focusing on the possible mechanisms of gastroprotection were also undertaken using the following experiments: evaluation of gastric secretion by the pylorus-ligated model, determination of mucus in gastric content, participation of nitric oxide (NO) and endogenous sulfhydryl in gastric protection. The results show that there was no significant effect on the volume of gastric juice and total acidity. However, the quantification of free gastric mucus showed that the clove oil and eugenol were capable of significantly enhancing mucus production. With regard to the NO and endogenous sulfhydryls, the results demonstrated that the gastroprotection induced by clove oil and eugenol are not related to the activities of the nitric oxide and endogenous sulfhydryls. No sign of toxicity was observed in the acute toxicity study. In conclusion, the results of this study show that essential oil of S. aromaticum, as well as its main component (eugenol), possesses antiulcer activity. The data suggest that the effectiveness of the essential oil and eugenol is based on its ability to stimulate the synthesis of mucus, an important gastroprotective factor. However, further pharmacological and toxicological investigations are required to enable its use for the treatment of gastric ulcer.
Chemopreventive efficacy of a betel leaf extract against benzo[a]pyrene-induced forestomach tumors in mice.

PubMed

Bhide, S V; Zariwala, M B; Amonkar, A J; Azuine, M A

1991-09-01

The effect of betel leaf extract and some of its constituents, eugenol, hydroxychavicol, beta-carotene and alpha-tocopherol, on benzo[a]pyrene-induced forestomach neoplasia in male Swiss mice was examined. Betel leaf and its constituents decreased the number of papillomas per animal with the maximum protection, considering molar dosage, exhibited by beta-carotene and alpha-tocopherol. Except for beta-carotene, eugenol, hydroxychavicol and alpha-tocopherol increased the levels of reduced glutathione in the liver while glutathione S-transferase activity was enhanced by all except eugenol. Of seven sources, Banarasi betel leaves showed the maximum amounts of beta-carotene and alpha-tocopherol.
Sensitivity of human dental pulp cells to eighteen chemical agents used for endodontic treatments in dentistry.

PubMed

Kobayashi, Morio; Tsutsui, Takeo W; Kobayashi, Tomoko; Ohno, Maki; Higo, Yukari; Inaba, Tomohiro; Tsutsui, Takeki

2013-01-01

To determine the adverse effects against human dental pulp tissue, the sensitivity of human dental pulp cells (D824 cells) to 18 chemical agents used for endodontic treatments in dentistry was examined. The cytotoxicity, as determined by a decrease in colony-forming ability of cells treated with the chemical agents, increased as the concentration increased. As a quantitative measure of the cytotoxic effect, LC(50), the concentration which induces a 50% lethality, was extrapolated from the concentration-response curves. The rank of the chemical agents according to their cytotoxic effect (LC(50)) was sodium arsenite > formaldehyde > hydrogen peroxide > zinc oxide > thymol ≈ iodoform ≈ eugenol > guaiacol > ethylenediaminetetraacetic acid ≈ iodine > procaine > lidocaine ≈ chloramphenicol ≈ m-cresol > calcium hydroxide ≈ sodium hypochlorite ≈ phenol ≈ p-phenolsulfonic acid. To compare the cytotoxicity and the levels of apoptosis and mRNA expression of five genes related to the function of dental pulp tissue, D824 cells treated with the LC(50) concentrations of chemical agents were assayed by the TUNEL method and quantitative reverse transcription polymerase chain reaction analysis, respectively. The inducibility of apoptotic cells and the level of mRNA expression of the genes varied with the chemical agents, indicating that both effects occurred independent of the rank of cytotoxic effect of the chemical agents. The results not only provide information concerning cytotoxicity of various chemical agents to human dental pulp cells, but also show an insight into the diversity of the pharmacodynamic action of the chemical agents.
Novel polymeric micelles for insect pest control: encapsulation of essential oil monoterpenes inside a triblock copolymer shell for head lice control.

PubMed

Lucia, Alejandro; Toloza, Ariel Ceferino; Guzmán, Eduardo; Ortega, Francisco; Rubio, Ramón G

2017-01-01

Essential oil components (EOCs) are molecules with interesting application in pest control, these have been evaluated against different insect pest from more than 100 years, but their practical use is rather limited. Thus, the enhancement of their bioavailability and manageability due to their dispersion in water can open new perspective for the preparation of formulations for the control of insect pest. In this work, we studied the encapsulation of different monoterpenes in a poloxamer shell in order to prepare aqueous formulations that can be used for the development of platforms used in pest control. Micellar systems containing a 5 wt% of poloxamer 407 and 1.25 wt% of the different monoterpenes were prepared. Dynamic Light Scattering (DLS) experiments were carried out to characterize the dispersion of the EOCs in water. The pediculicidal activity of these micellar systems was tested on head lice using an ex vivo immersion test. The poloxamers allowed the dispersion of EOCs in water due to their encapsulation inside the hydrophobic core of the copolymer micelles. From this study, we concluded that it is possible to make stable micellar systems containing water (>90 wt%), 1.25 wt% of different monoterpenes and a highly safe polymer (5wt% Poloxamer 407). These formulations were effective against head lice with mortality ranging from 30 to 60%, being the most effective emulsions those containing linalool, 1,8-cineole, α -terpineol, thymol, eugenol, geraniol and nonyl alcohol which lead to mortalities above 50%. Since these systems showed good pediculicidal activity and high physicochemical stability, they could be a new route for the green fabrication of biocompatible and biosustainable insecticide formulations.

Novel polymeric micelles for insect pest control: encapsulation of essential oil monoterpenes inside a triblock copolymer shell for head lice control

PubMed Central

Guzmán, Eduardo; Ortega, Francisco; Rubio, Ramón G.

2017-01-01

Background Essential oil components (EOCs) are molecules with interesting application in pest control, these have been evaluated against different insect pest from more than 100 years, but their practical use is rather limited. Thus, the enhancement of their bioavailability and manageability due to their dispersion in water can open new perspective for the preparation of formulations for the control of insect pest. In this work, we studied the encapsulation of different monoterpenes in a poloxamer shell in order to prepare aqueous formulations that can be used for the development of platforms used in pest control. Methods Micellar systems containing a 5 wt% of poloxamer 407 and 1.25 wt% of the different monoterpenes were prepared. Dynamic Light Scattering (DLS) experiments were carried out to characterize the dispersion of the EOCs in water. The pediculicidal activity of these micellar systems was tested on head lice using an ex vivo immersion test. Results The poloxamers allowed the dispersion of EOCs in water due to their encapsulation inside the hydrophobic core of the copolymer micelles. From this study, we concluded that it is possible to make stable micellar systems containing water (>90 wt%), 1.25 wt% of different monoterpenes and a highly safe polymer (5wt% Poloxamer 407). These formulations were effective against head lice with mortality ranging from 30 to 60%, being the most effective emulsions those containing linalool, 1,8-cineole, α-terpineol, thymol, eugenol, geraniol and nonyl alcohol which lead to mortalities above 50%. Discussion Since these systems showed good pediculicidal activity and high physicochemical stability, they could be a new route for the green fabrication of biocompatible and biosustainable insecticide formulations. PMID:28439460
Blossom thinning in apple and peach with an essential oil

USDA-ARS?s Scientific Manuscript database

A series of experiments were conducted with apple (Malus xdomestica) and peach [Prunus persica (L.) Batsch] from 2003-2008 to evaluate the flower thinning efficacy of eugenol and a eugenol-based essential oil. Flower thinning effects by hand defoliation and alternative chemical agents were compared...
Intra-laboratory study to determine the reproducibility of LLNA:BrdU-ELISA for the prediction of the skin sensitizing potential of chemicals.

PubMed

Chen, Wei; Xing, Caihong; Hou, Fenxia

The Local Lymph Node Assay (LLNA) has been designated as the first-choice in vivo assay for identification the skin sensitization potential of new chemicals. The LLNA:BrdU-ELISA is a validated non-radioactive modification to the LLNA. An intra-laboratory reproducibility study for the LLNA:BrdU-ELISA was conducted to demonstrate its adequate performance in our laboratory. Ten independent LLNA:BrdU-ELISAs with the preferred positive controls (PCs), i.e., 25% hexyl cinnamic aldehyde (HCA) and 25% eugenol, were conducted within a period of less than one year. In addition, different concentrations of 2,4-dinitrochlorobenzene (DNCB, an extreme sensitizer) (0.01, 0.1 and 0.3%), HCA (10, 25 and 50%) and eugenol (10, 25 and 50%), were tested to determine the EC1.6 values. Special Pathogen Free female CBA/J mice of 8-10weeks old were randomly allocated to the groups, each group having 4 mice. 25μl of AOO (vehicle, acetone: olive oil=4:1, v/v) or HCA, eugenol, DNCB at the needed concentration was applied to the dorsum of each ear of the mice, daily for 3 consecutive days. A single intraperitoneal injection of 0.5ml of BrdU solution (10mg/ml) was given on day 5. On day 6, a pair of auricular lymph nodes from each mouse was excised, and BrdU ELISA analysis was conducted. The result for each group is expressed as the mean Stimulation Index (SI). The mean of the 10 mean SIs for 25% HCA (2.58±0.95) and 25% eugenol (3.51±1.25) was not significantly different to that from the Interagency Coordinating Committee on the Validation of Alternative Methods (ICCVAM) (i.e., the data on the formal validation study for the LLNA:BrdU-ELISA by the ICCVAM) (3.03±2.00 for 25% HCA, 6.13±6.06 for 25% eugenol) (P>0.05), with even smaller Coefficient of Variations (CV) (36.8% for 25% HCA, 35.6% for 25% eugenol) than that from the ICCVAM (66.0% for 25% HCA, 98.8% for 25% eugenol). In addition, the EC1.6 values for HCA, eugenol and DNCB (15.2, 12.5 and 0.25%, respectively) were consistent with that from the ICCVAM (12.92, 8.85 and 0.34%, respectively). The results indicate that the reliability for our laboratory to conduct the LLNA:BrdU-ELISA is successfully determined. Copyright © 2016 Elsevier Inc. All rights reserved.
Identification of repellent odorants to the body louse, Pediculus humanus corporis, in clove essential oil.

PubMed

Iwamatsu, Takuma; Miyamoto, Daisuke; Mitsuno, Hidefumi; Yoshioka, Yoshiaki; Fujii, Takeshi; Sakurai, Takeshi; Ishikawa, Yukio; Kanzaki, Ryohei

2016-04-01

The control of body lice is an important issue for human health and welfare because lice act as vectors of disease such as typhus, relapsing fever, and trench fever. Body lice exhibit avoidance behavior to some essential oils, including clove essential oil. Therefore, odorants containing clove essential oil components may potentially be useful in the development of repellents to body lice. However, such odorants that induce avoidance behavior in body lice have not yet been identified from clove essential oil. Here, we established an analysis method to evaluate the avoidance behavior of body lice to specific odorants. The behavioral analysis of the body lice in response to clove essential oil and its constituents revealed that eugenol, a major component of clove essential oil, has strong repellent effect on body lice, whereas the other components failed to induce obvious avoidance behavior. A comparison of the repellent effects of eugenol with those of other structurally related odorants revealed possible moieties that are important for the avoidance effects to body lice. The repellent effect of eugenol to body lice was enhanced by combining it with the other major component of clove essential oil, β-caryophyllene. We conclude that a synthetic blend of eugenol and β-caryophyllene is the most effective repellent to body lice. This finding will be valuable as the potential use of eugenol as body lice repellent.
Antimicrobial eugenol nanoemulsion prepared by gum arabic and lecithin and evaluation of drying technologies.

PubMed

Hu, Qiaobin; Gerhard, Hannah; Upadhyaya, Indu; Venkitanarayanan, Kumar; Luo, Yangchao

2016-06-01

The purpose of present work was to develop eugenol oil nanoemulsions using gum arabic and lecithin as food grade natural emulsifiers, and study their antimicrobial activity. In addition, our study also evaluated different drying techniques (spray drying and freeze drying) on the morphology and redispersibility of nanoemulsion powders. The optimal fabrication method, physicochemical and structural characterization, stability, and antimicrobial activity were investigated. Results showed that nanoemusions with a particle size of 103.6±7.5nm were obtained by mixing aqueous phase (0.5% gum arabic, 0.5% lecithin, w/v) and eugenol oil (1.25%, w/v), which was premixed with ethanol (as a co-surfactant), followed by high speed homogenization process. The molecular interactions among emulsifiers and eugenol were evidenced by Fourier transform infrared spectroscopy. Buchi B-90 Nano Spray Dryer was evaluated as a powerful tool to obtain ultrafine spherical powders with a size of less than 500nm, compared to flake-like aggregation obtained by freeze-drying. The dried powders exhibited excellent re-dispersibility in water and maintained their physicochemical properties after re-hydration. The nanoemulsions did not adversely affect the antimicrobial activity of eugenol against Listeria monocytogenes and Salmonella Enteritidis. Therefore, the nanoemulsions have the potential to be applied in the food industry as a food preservative or sanitizer. Copyright © 2016 Elsevier B.V. All rights reserved.
Electrochemical oxidation mechanism of eugenol on graphene modified carbon paste electrode and its analytical application to pharmaceutical analysis.

PubMed

Yildiz, Gulcemal; Aydogmus, Zeynep; Cinar, M Emin; Senkal, Filiz; Ozturk, Turan

2017-10-01

Electrochemical properties of eugenol were investigated on a graphene modified carbon paste electrode (CPE) by using voltammetric methods, which exhibited a well-defined irreversible peak at about 0.7V vs Ag/AgCl, NaCl (3M) in Britton-Robinson buffer at pH 2.0. Mechanism of the electrochemical reaction of eugenol was studied by performing density functional theory (DFT) computations and mass spectroscopic analysis. (CPCM:water)-wB97XD/aug-cc-PVTZ//(CPCM:water)-wB97XD/6-31G(d) level calculations predicted that the formation of product P2, possessing a para-quinoid structure, is preferred rather than the product P1, suggested in the literature, having an ortho-quinoid system. Determination of eugenol in a pharmaceutical sample was realized in the light of the electrochemical findings, and a validated voltammetric method for quantitative analysis of eugenol in a pharmaceutical formulation was proposed. The differential pulse voltammogram (DPV) peak currents were found to be linear in the concentration range of 1.0 × 10 -7 to 1.7 × 10 -5 M. The limit of detection (LOD) and the limit of quantification (LOQ) were obtained to be 7.0 × 10 -9 and 2.3 × 10 -8 , respectively. Copyright © 2017 Elsevier B.V. All rights reserved.
Preparation of eugenol-based polyurethane

NASA Astrophysics Data System (ADS)

Li, Yupeng; Luo, Fang; Cheng, Chuanjie

2018-03-01

The regenerative eugenol was used as the starting material to prepare diol species by two steps, with a total yield of 28%. Furthermore, the prepared diol reacts with 1,6-hexadiisocyanate(HDI) to afford the corresponding polyurethane (PU). The structure of intermediates and PU are characterized by 1H-NMR or IR.
40 CFR 180.1067 - Methyl eugenol and malathion combination; exemption from the requirement of a tolerance.

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 25 2012-07-01 2012-07-01 false Methyl eugenol and malathion... Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) PESTICIDE PROGRAMS TOLERANCES AND EXEMPTIONS FOR.... Department of Agriculture, in accordance with the following directions and specifications: (a) The...
40 CFR 180.1067 - Methyl eugenol and malathion combination; exemption from the requirement of a tolerance.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 23 2010-07-01 2010-07-01 false Methyl eugenol and malathion... Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) PESTICIDE PROGRAMS TOLERANCES AND EXEMPTIONS FOR.... Department of Agriculture, in accordance with the following directions and specifications: (a) The...
Antifungal activity against Candida albicans of starch Pickering emulsion with thymol or amphotericin B in suspension and calcium alginate films.

PubMed

Cossu, Andrea; Wang, Min S; Chaudhari, Amol; Nitin, Nitin

2015-09-30

Conventional antifungal treatments against Candida albicans in the oral cavity often result in increased cytotoxicity. The goal of this study was to determine the potential of starch Pickering emulsion as a delivery vehicle for an antifungal natural phenolic compound such as thymol in simulated saliva fluid (SSF) compared to amphotericin B. An oil-in-water (o/w) emulsion was stabilized using starch particles. Physical stability of the emulsion and disruption induced by α-amylase activity in SSF was evaluated. Encapsulated thymol in o/w emulsion was compared to encapsulated amphotericin B for antifungal activity against C. albicans in suspension using emulsions or zone inhibition assay on agar plates using emulsions dispersed in alginate films. Results showed that the emulsions were stable for at least three weeks. Digestion of the emulsion by α-amylase led to coalescence of emulsion droplets. The antifungal activity of thymol and amphotericin B in emulsion formulation was enhanced upon incubation with α-amylase. Results from the zone inhibition assay demonstrated efficacy of the emulsions dispersed in alginate films. Interestingly, addition of α-amylase to the alginate films resulted in a decreased inhibitory effect. Overall, this study showed that starch Pickering emulsions have a potential to deliver hydrophobic antifungal compounds to treat oral candidiasis. Copyright © 2015 Elsevier B.V. All rights reserved.
Cell viability of Candida albicans against the antifungal activity of thymol.

PubMed

de Vasconcelos, Laís César; Sampaio, Fabio Correia; Albuquerque, Allan de Jesus dos Reis; Vasconcelos, Laurylene César de Souza

2014-01-01

Candida albicans is a commensal fungus, but circumstantially it may cause superficial infections of the mucous membranes, such as denture stomatitis, when a biofilm is formed on the surface of dental prostheses. This study evaluated the cell viability of C. albicans biofilms against the antifungal activity of thymol when compared with miconazole, by the fluorescence imaging using SYTO 9 and propidium iodide dyes, and counting of colony forming units. C. albicans standard strains (ATCC 11006) were used. The minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) of drugs were determined by broth microdilution tests and the inoculum was standardized to match 0.5 on the McFarland scale (106 cfu/mL). Biofilms were grown on the surface of acrylic resin disks in parallel flow chambers from Sabouraud broth supplemented with 10% dextrose. For counting of colony forming units, the fungal solution was sequentially diluted and plated in Sabouraud dextrose agar. Data were analyzed using two-way ANOVA and Tukey's test (a=5%). Biofilms treated with thymol and miconazole presented low numbers of viable cells at the evaluated exposure times. There was statistically significant difference (p<0.05) when compared with control, and the mean value of the exposure times between miconazole and thymol did not differ significantly (p>0.05). In conclusion, both drugs have similar efficiency as antifungal agents against biofilms of C. albicans formed on acrylic surfaces.
Effect of storage duration/solution on microshear bond strength of composite to enamel.

PubMed

Tosun, Gul; Sener, Yagmur; Sengun, Abdulkadir

2007-01-01

The aim of this study was to determine the effect of three storage solutions and two storage durations on microshear bond strength (microSBS) of a resin composite. Sixty non-carious human permanent molars were stored in three storage solutions (0.1% thymol, 10% formalin, and distilled water). Each tooth was separated mesio-distally into two parts. Specimens of the first part were stored for 24 hours, while specimens of the second part were stored for two months in the solutions. After each storage period, the enamel surface was covered with a composite resin in combination with an etch-rinse adhesive system. Specimens were then serially sectioned into sticks of 1 mm' bond area and subjected to microSBS test. There were no statistically significant differences between the two storage periods for each solution (p>0.05). The thymol solution group showed lower microSBS values than those of distilled water for both storage periods (p<0.05). As for the formalin group, its microSBS values were not statistically different from those of distilled water and thymol groups at each storage period (p>0.05). In conclusion, the thymol solution caused the microSBS of the resin composite to decrease when compared to both formalin and distilled water after 24 hours and two months. However, the microSBS of the resin composite was not affected by storage duration.
Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils.

PubMed

Tabanca, Nurhayat; Demirci, Betul; Crockett, Sara L; Başer, Kemal Hüsnü Can; Wedge, David E

2007-10-17

Essential oils from three different Asteraceae obtained by hydrodistillation of aerial parts were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC/MS). Main compounds obtained from each taxon were found as follows: Arnica longifolia carvacrol 37.3%, alpha-bisabolol 8.2%; Aster hesperius hexadecanoic acid 29.6%, carvacrol 15.2%; and Chrysothamnus nauseosus var. nauseosus beta-phellandrene 22.8% and beta-pinene 19.8%. Essential oils were also evaluated for their antimalarial and antimicrobial activity against human pathogens, and antifungal activities against plant pathogens. No antimalarial and antimicrobial activities against human pathogens were observed. Direct bioautography demonstrated antifungal activity of the essential oils obtained from three Asteraceae taxa and two pure compounds, carvacrol and beta-bisabolol, to the plant pathogens Colletotrichum acutatum, C. fragariae and C. gloeosporioides. Subsequent evaluation of antifungal compounds using a 96-well micro-dilution broth assay indicated that alpha-bisabolol showed weak growth inhibition of the plant pathogen Botrytis cinerea after 72 h.
Antioxidant Activity of the Essential Oil and its Major Terpenes of Satureja macrostema (Moc. and Sessé ex Benth.) Briq.

PubMed

Torres-Martínez, Rafael; García-Rodríguez, Yolanda Magdalena; Ríos-Chávez, Patricia; Saavedra-Molina, Alfredo; López-Meza, Joel Edmundo; Ochoa-Zarzosa, Alejandra; Garciglia, Rafael Salgado

2018-01-01

The aim of this study was to investigate the in vitro antioxidant activity of Satureja macrostema (Moc. and Sessé ex Benth.) Briq. (Lamiaceae) essential oil, a Mexican medicinal plant known as nurite. Fresh aerial parts of S. macrostema plants cultivated in greenhouse for 3 months were subjected to hydrodistillation in a Clevenger apparatus to obtain essential oil. Volatile compounds were identified by gas chromatography (GC) and GC/mass spectrometry. Antioxidant effectiveness of essential oil and its major terpenes of S. macrostema was examined by three different radical scavenging methods: 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), and total antioxidant capacity (TAC). The concentrations tested were 0.001, 0.01, 0.1, and 1 mg/mL. The major volatile compounds were caryophyllene, limonene, linalool, pulegone, menthone, and thymol. S. macrostema essential oil showed the highest free radical scavenging activity with DPPH and ABTS methods (53.10% and 92.12%, respectively) at 1 mg/mL and 98% with TAC method at 0.1 mg/mL. Thymol exerted the highest antioxidant capacity with 0.1 mg/mL, reaching 83.38%, 96.96%, and 98.57% by DPPH, ABTS, and TAC methods. Caryophyllene, limonene, linalool, pulegone, and menthone exhibited an antioxidant capacity <25% with the DPPH and ABTS methods; however, limonene showed a TAC of 85.41% with 0.01 mg/mL. The essential oil of S. macrostema and thymol showed a free radical scavenging activity close to that of the synthetic butylated hydroxytoluene. The major volatile compounds of essential oil of Satureja macrostema were caryophyllene, limonene, linalool, pulegone, menthone and thymolThe essential oil of S. macrostema showed a high free radical scavengingThymol exerted the highest antioxidant capacity by DPPH, ABTS and TAC methods. Abbreviations used: GC: Gas Chromatography; DPPH: 2,2-diphenyl-1-picrylhydrazyl; ABTS: 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid; TAC: Total antioxidant capacity.
Modeling the Inactivation of Intestinal Pathogenic Escherichia coli O157:H7 and Uropathogenic E. coli in Ground Chicken by High Pressure Processing and Thymol

PubMed Central

Chien, Shih-Yung; Sheen, Shiowshuh; Sommers, Christopher H.; Sheen, Lee-Yan

2016-01-01

Disease causing Escherichia coli commonly found in meat and poultry include intestinal pathogenic E. coli (iPEC) as well as extraintestinal types such as the Uropathogenic E. coli (UPEC). In this study we compared the resistance of iPEC (O157:H7) to UPEC in chicken meat using High Pressure Processing (HPP) in with (the hurdle concept) and without thymol essential oil as a sensitizer. UPEC was found slightly more resistant than E. coli O157:H7 (iPEC O157:H7) at 450 and 500 MPa. A central composite experimental design was used to evaluate the effect of pressure (300–400 MPa), thymol concentration (100–200 ppm), and pressure-holding time (10–20 min) on the inactivation of iPEC O157:H7 and UPEC in ground chicken. The hurdle approach reduced the high pressure levels and thymol doses imposed on the food matrices and potentially decreased food quality damaged after treatment. The quadratic equations were developed to predict the impact (lethality) on iPEC O157:H7 (R2 = 0.94) and UPEC (R2 = 0.98), as well as dimensionless non-linear models [Pr > F (<0.0001)]. Both linear and non-linear models were validated with data obtained from separated experiment points. All models may predict the inactivation/lethality within the same order of accuracy. However, the dimensionless non-linear models showed potential applications with parameters outside the central composite design ranges. The results provide useful information of both iPEC O157:H7 and UPEC in regard to how they may survive HPP in the presence or absence of thymol. The models may further assist regulatory agencies and food industry to assess the potential risk of iPEC O157:H7 and UPEC in ground chicken. PMID:27379050
Attraction of Diabrotica barberi Smith and Lawrence (Coleoptera: Chrysomelidae) to eugenol-baited traps in soybean

USDA-ARS?s Scientific Manuscript database

Diabrotica barberi Smith and Lawrence (the northern corn rootworm) is a native North American leaf beetle and a major pest of corn. However, adult D. barberi forage in various habitats outside of corn, including soybean, roadside vegetation, and prairie. Eugenol is a common floral volatile that ha...
Terminalia larval host fruit reduces the response of Bactrocera dorsalis adults to the male lure methyl eugenol

USDA-ARS?s Scientific Manuscript database

Methyl eugenol(ME) is a powerful semiochemical attractant to males of the oriental fruit fly, Bactrocera dorsalis, and is the keystone of detection, control, and eradication programs against this polyphagous and highly invasive tephritid pest. Despite its status as a model lure against B.dorsalis, v...
Using Ozone in Organic Chemistry Lab: The Ozonolysis of Eugenol

ERIC Educational Resources Information Center

Branan, Bruce M.; Butcher, Joshua T.; Olsen, Lawrence R.

2007-01-01

An ozonolysis experiment, suitable for undergraduate organic chemistry lab, is presented. Ozonolysis of eugenol (clove oil), followed by reductive workup furnishes an aldehyde that is easily identified by its NMR and IR spectra. Ozone (3-5% in oxygen) is produced using an easily built generator. (Contains 2 figures and 1 scheme.)
Evaluation of bioactivity of linalool-rich essential oils from Ocimum basilucum and Coriandrum sativum varieties.

PubMed

Duman, Ahmet D; Telci, Isa; Dayisoylu, Kenan S; Digrak, Metin; Demirtas, Ibrahim; Alma, Mehmet H

2010-06-01

Essential oils from Ocimum basilicum L. and Coriandrum sativum L. varieties originating from Turkey were investigated for their antimicrobial properties. The antimicrobial effects of the oil varieties were evaluated by the disc diffusion and minimum inhibitory concentration (MIC) methods against eight bacteria and three fungi. The compositions of the essential oils were analyzed and identified by GC and GC-MS. O. basilicum, C. sativum var. macrocarpum and var. microcarpum oils revealed the presence of linalool (54.4%), eugenol (9.6%), methyl eugenol (7.6%); linalool (78.8%), gamma-terpinene (6.0%), nerol acetate (3.5%); and linalool (90.6%), and nerol acetate (3.3%) as the major components, respectively. The oils exhibited antibacterial activity ranging from 1.25 to 10 microL disc(-1) against the test organisms with inhibition zones of 9.5-39.0 mm and minimal inhibitory concentrations values in the range 0.5- > or =1 microL/L. Linalool, eugenol, and methyl eugenol at 1.25 microL disc(-1) had antimicrobial effects on all microorganisms, giving inhibition zones ranging from 7 to 19 mm.
Synthesis of Eugenol–Lauryl Methacrylate Copolymers via Cationic Polymerization

NASA Astrophysics Data System (ADS)

Fajrin, A.; Marliana, SD; Handayani, D. S.

2018-04-01

Eugenol is one of the most abundant natural resources in Indonesia. The recently bio-based polymer resin is created based on eugenol because eugenol is functionalized with the polymerizable group. In order to improve the functional properties of eugenol, in this research Eugenol–Lauryl Methacrylate copolymers (co-poly(Eg-LMA)) were synthesized by cationic polymerization using H2SO4 as an initiator under the nitrogen atmosphere. Structure identification of the copolymer showed the absorption of the vinyl group from the monomers disappear at the analysis through FTIR at the wave number 1637-1639 and 985-995 cm-1 and also 1H-NMR on the chemical shift 5,97 and 5,08 ppm. The resulting copolymers obtained brown powder in 32.03 % yieldsand melting point at 96 – 97 °C. Solubility test of the co-poly(Eg-LMA) showed that the polymer couldnot soluble in water but soluble in chloroform, diethyl ether, and benzene. Average molecular weight of co-poly(Eg-LMA) Led Ostwald viscometry was obtained 42020 with the degree of polymerization by 200.

Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester

PubMed Central

Koeduka, Takao; Fridman, Eyal; Gang, David R.; Vassão, Daniel G.; Jackson, Brenda L.; Kish, Christine M.; Orlova, Irina; Spassova, Snejina M.; Lewis, Norman G.; Noel, Joseph P.; Baiga, Thomas J.; Dudareva, Natalia; Pichersky, Eran

2006-01-01

Phenylpropenes such as chavicol, t-anol, eugenol, and isoeugenol are produced by plants as defense compounds against animals and microorganisms and as floral attractants of pollinators. Moreover, humans have used phenylpropenes since antiquity for food preservation and flavoring and as medicinal agents. Previous research suggested that the phenylpropenes are synthesized in plants from substituted phenylpropenols, although the identity of the enzymes and the nature of the reaction mechanism involved in this transformation have remained obscure. We show here that glandular trichomes of sweet basil (Ocimum basilicum), which synthesize and accumulate phenylpropenes, possess an enzyme that can use coniferyl acetate and NADPH to form eugenol. Petunia (Petunia hybrida cv. Mitchell) flowers, which emit large amounts of isoeugenol, possess an enzyme homologous to the basil eugenol-forming enzyme that also uses coniferyl acetate and NADPH as substrates but catalyzes the formation of isoeugenol. The basil and petunia phenylpropene-forming enzymes belong to a structural family of NADPH-dependent reductases that also includes pinoresinol–lariciresinol reductase, isoflavone reductase, and phenylcoumaran benzylic ether reductase. PMID:16782809
Synergistic Interactions of Eugenol-tosylate and Its Congeners with Fluconazole against Candida albicans.

PubMed

Ahmad, Aijaz; Wani, Mohmmad Younus; Khan, Amber; Manzoor, Nikhat; Molepo, Julitha

2015-01-01

We previously reported the antifungal properties of a monoterpene phenol "Eugenol" against different Candida strains and have observed that the addition of methyl group to eugenol drastically increased its antimicrobial potency. Based on the results and the importance of medicinal synthetic chemistry, we synthesized eugenol-tosylate and its congeners (E1-E6) and tested their antifungal activity against different clinical fluconazole (FLC)- susceptible and FLC- resistant C. albicans isolates alone and in combination with FLC by determining fractional inhibitory concentration indices (FICIs) and isobolograms calculated from microdilution assays. Minimum inhibitory concentration (MIC) results confirmed that all the tested C. albicans strains were variably susceptible to the semi-synthetic derivatives E1-E6, with MIC values ranging from 1-62 μg/ml. The test compounds in combination with FLC exhibited either synergy (36%), additive (41%) or indifferent (23%) interactions, however, no antagonistic interactions were observed. The MICs of FLC decreased 2-9 fold when used in combination with the test compounds. Like their precursor eugenol, all the derivatives showed significant impairment of ergosterol biosynthesis in all C. albicans strains coupled with down regulation of the important ergosterol biosynthesis pathway gene-ERG11. The results were further validated by docking studies, which revealed that the inhibitors snugly fitting the active site of the target enzyme, mimicking fluconazole, may well explain their excellent inhibitory activity. Our results suggest that these compounds have a great potential as antifungals, which can be used as chemosensitizing agents with the known antifungal drugs.
Antihypercholesterolemic and Antioxidative Potential of an Extract of the Plant, Piper betle, and Its Active Constituent, Eugenol, in Triton WR-1339-Induced Hypercholesterolemia in Experimental Rats.

PubMed

Venkadeswaran, Karuppasamy; Muralidharan, Arumugam Ramachandran; Annadurai, Thangaraj; Ruban, Vasanthakumar Vasantha; Sundararajan, Mahalingam; Anandhi, Ramalingam; Thomas, Philip A; Geraldine, Pitchairaj

2014-01-01

Hypercholesterolemia is a dominant risk factor for atherosclerosis and cardiovascular diseases. In the present study, the putative antihypercholesterolemic and antioxidative properties of an ethanolic extract of Piper betle and of its active constituent, eugenol, were evaluated in experimental hypercholesterolemia induced by a single intraperitoneal injection of Triton WR-1339 (300 mg/kg b.wt) in Wistar rats. Saline-treated hypercholesterolemic rats revealed significantly higher mean blood/serum levels of glucose, total cholesterol, triglycerides, low density and very low density lipoprotein cholesterol, and of serum hepatic marker enzymes; in addition, significantly lower mean serum levels of high density lipoprotein cholesterol and significantly lower mean activities of enzymatic antioxidants and nonenzymatic antioxidants were noted in hepatic tissue samples from saline-treated hypercholesterolemic rats, compared to controls. However, in hypercholesterolemic rats receiving the Piper betle extract (500 mg/kg b.wt) or eugenol (5 mg/kg b.wt) for seven days orally, all these parameters were significantly better than those in saline-treated hypercholesterolemic rats. The hypercholesterolemia-ameliorating effect was better defined in eugenol-treated than in Piper betle extract-treated rats, being as effective as that of the standard lipid-lowering drug, lovastatin (10 mg/kg b.wt). These results suggest that eugenol, an active constituent of the Piper betle extract, possesses antihypercholesterolemic and other activities in experimental hypercholesterolemic Wistar rats.
Antihypercholesterolemic and Antioxidative Potential of an Extract of the Plant, Piper betle, and Its Active Constituent, Eugenol, in Triton WR-1339-Induced Hypercholesterolemia in Experimental Rats

PubMed Central

Venkadeswaran, Karuppasamy; Muralidharan, Arumugam Ramachandran; Annadurai, Thangaraj; Ruban, Vasanthakumar Vasantha; Sundararajan, Mahalingam; Anandhi, Ramalingam; Thomas, Philip A.; Geraldine, Pitchairaj

2014-01-01

Hypercholesterolemia is a dominant risk factor for atherosclerosis and cardiovascular diseases. In the present study, the putative antihypercholesterolemic and antioxidative properties of an ethanolic extract of Piper betle and of its active constituent, eugenol, were evaluated in experimental hypercholesterolemia induced by a single intraperitoneal injection of Triton WR-1339 (300 mg/kg b.wt) in Wistar rats. Saline-treated hypercholesterolemic rats revealed significantly higher mean blood/serum levels of glucose, total cholesterol, triglycerides, low density and very low density lipoprotein cholesterol, and of serum hepatic marker enzymes; in addition, significantly lower mean serum levels of high density lipoprotein cholesterol and significantly lower mean activities of enzymatic antioxidants and nonenzymatic antioxidants were noted in hepatic tissue samples from saline-treated hypercholesterolemic rats, compared to controls. However, in hypercholesterolemic rats receiving the Piper betle extract (500 mg/kg b.wt) or eugenol (5 mg/kg b.wt) for seven days orally, all these parameters were significantly better than those in saline-treated hypercholesterolemic rats. The hypercholesterolemia-ameliorating effect was better defined in eugenol-treated than in Piper betle extract-treated rats, being as effective as that of the standard lipid-lowering drug, lovastatin (10 mg/kg b.wt). These results suggest that eugenol, an active constituent of the Piper betle extract, possesses antihypercholesterolemic and other activities in experimental hypercholesterolemic Wistar rats. PMID:24523820
The effect of root canal sealers and timing of cementation on the microlekage of the parapost luted with resin cement

PubMed Central

Al Kahtani, Ahmed M.

2010-01-01

Objectives The objectives of the study were to study the effect of root canal sealers either eugenol or non-eugenol and timing of cementation on microleakage of the parapost luted with resin cement. Materials and methods Seventy extracted human, single-rooted teeth were instrumented using a crown-down technique. All teeth were instrumented up to a size 50 .04 taper ProFile followed by the use of Gates Glidden drills from size 2 up to 5. Following instrumentation, the teeth were randomly divided into four experimental groups of fifteen teeth each, based on type of root canal sealer (eugenol or non-eugenol sealer) and timing of post cementation (immediate or delayed). The remaining ten teeth were divided into two control groups with five teeth per group. All teeth were tested for microleakage using a fluid filtration method. Results The microleakage of the paraposts luted with resin cement increased over time, irrespective of sealer type or timing of post cementation. Immediate post cementation following obturation with AH26 (non-eugenol sealer) produced the least microleakage at all three time periods at 24 h, 2 months and 3 months. Conclusions The microleakage paraposts luted with resin cement was not influenced by either sealer type or timing of post placement. All experimental groups demonstrated a significant increase in microleakage over time as well as the presence of voids at the resin–dentin interface. PMID:24109165
Characterization of Essential Oil Composition in Different Basil Species and Pot Cultures by a GC-MS Method.

PubMed

Muráriková, Andrea; Ťažký, Anton; Neugebauerová, Jarmila; Planková, Alexandra; Jampílek, Josef; Mučaji, Pavel; Mikuš, Peter

2017-07-20

Basil ( Ocimum L.) species are used as medicinal plants due to their essential oils exhibiting specific biological activity. The present work demonstrated that both the variety and season/conditions of cultivation had a significant effect on (i) the produced amount (extraction yield), (ii) qualitative, as well as (iii) quantitative profile of basil essential oil. Among studied basil varieties, a new variety, 'Mánes', was characterized for the first time. Based on our quantitative evaluation of GC-MS profiles, the following chemotypes and average concentrations of a main component were detected in the studied basil varieties: 'Ohře', 'Lettuce Leaf', 'Purple Opaal', 'Dark Green' (linalool, 5.99, 2.49, 2.34, 2.01 mg/mL, respectively), and 'Mammolo Genovese', 'Mánes', 'Red Rubin' (eucalyptol, 1.34, 0.96, 0.76 mg/mL, respectively). At the same time, when considering other compounds identified in GC-MS profiles, all the studied varieties, except from 'Lettuce Leaf', were methyl eugenol-rich with a strong dependence of the eugenol:methyl eugenol ratio on the seasonal changes (mainly solar irradiation, but also temperature and relative humidity). More complex and/or variable (depending on the season and cultivation) chemotypes were observed with 'Lettuce Leaf' (plus estragole, 2.27 mg/mL), 'Dark Green' (plus eucalyptol, 1.36 mg/mL), 'Mammolo Genovese' (plus eugenol, 1.19 mg/mL), 'Red Rubin' (plus linalool and eugenol, 0.46 and 0.56 mg/mL, respectively), and 'Mánes' (plus linalool and eugenol, 0.58 and 0.40 mg/mL, respectively). When considering superior extraction yield (ca. 17 mL·kg -1 , i.e., two to five times higher than other examined varieties) and consistent amounts (yields) of essential oil when comparing inter-seasonal or inter-year data (RSD and inter-year difference in mean yield values ˂2.5%), this new basil variety is very promising for use in the pharmaceutical, food, and cosmetic industries.
Cytotoxicity and anti-inflammatory effects of zinc ions and eugenol during setting of ZOE in immortalized human oral keratinocytes grown as three-dimensional spheroids.

PubMed

Lee, Jung-Hwan; Lee, Hae-Hyoung; Kim, Kyoung-Nam; Kim, Kwang-Mahn

2016-05-01

The objective of this study is to assess the cytotoxic and anti-inflammatory effects of ZOE cement during setting in two-dimensional (2D) or three-dimensional (3D) cultures of immortalized human oral keratinocytes (IHOKs) with determining the extract components responsible for these effects. Extracts of mixed ZOE at different stages of setting were analyzed by a digital pH meter, ICP-MS, and GC-MS. Serial concentrations of extract and their mixture of ZnCl2, ZnSO4·H2O, and eugenol liquid were added to the 2D and 3D IHOK cultures to determine the half maximal effective concentration in investigating the cause of cytotoxicity by means of WST assay and to investigate mRNA expression levels of inflammatory cytokines by RT-PCR. Zn(2+) and eugenol (4-19 ppm) were detected in the extracts. In the early setting stage, significant cytotoxicity was observed in the 2D and 3D IHOK cultures (P<0.05). The EC50 of Zn(2+) from ZnCl2 was 5-44 ppm in both cultures, whereas the EC50 of eugenol was not detectable under 100 ppm. Along with the lower levels of inflammatory cytokine gene expressions in the extract, treatment of the 2D IHOKs with Zn(2+) alone and treatment of the 3D IHOKs with Zn(2+) plus eugenol resulted in significantly lower expression levels of IL-1β, IL-6, and IL-8 (P<0.05). The cytotoxic effect of ZOE on IHOKs was greater during the setting stage owing to the presence of Zn(2+). The anti-inflammatory response to ZOE was induced by a combination of Zn(2+) and eugenol. Cytotoxic and anti-inflammatory effects differed between the 2D and 3D IHOK cultures. Copyright © 2016. Published by Elsevier Ltd.
Characterization of Thymol blue Radiochromic dosimeters for high dose applications

NASA Astrophysics Data System (ADS)

Aldweri, Feras M.; Abuzayed, Manar H.; Al-Ajaleen, Musab S.; Rabaeh, Khalid A.

2018-03-01

Thymol blue (TB) solutions and Thymol blue Polyvinyl Alcohol (TB-PVA) films have been introduced as Radiochromic dosimeter for high dose applications. The dosimeters were irradiated with gamma ray (60Co source) from 5 to 30 kGy for film, and from 0.150 kGy to 4 kGy for solution. The optical density of unirradiated and irradiated TB solution as well as TB-PVA film dosimeters were studied in terms of absorbance at 434 nm using UV/VIS spectrophotometer. The effects of scan temperature, light pre-gamma irradiation, dose rate, relative humidity and stability of the absorbance of solutions and films after irradiation were investigated. We found the dose sensitivity of TB solution and TB-PVA film dosimeters increases significantly with increases of the absorbed dose as well as with the increases of TB dye concentrations. The useful dose range of developed TB solutions and TB-PVA films dosimeters is in the range 0.125-1 kGy and of 5-20 kGy, respectively.
Trachyspermum ammi (L.) sprague: chemical composition of essential oil and antimicrobial activities of respective fractions.

PubMed

Moein, Mahmoodreza R; Zomorodian, Kamiar; Pakshir, Keyvan; Yavari, Farnoosh; Motamedi, Marjan; Zarshenas, Mohammad M

2015-01-01

Resistance to antibacterial agents has become a serious problem for global health. The current study evaluated the antimicrobial activities of essential oil and respective fractions of Trachyspermum ammi (L.) Sprague. Seeds of the essential oil were extracted and fractionated using column chromatography. All fractions were then analyzed by gas chromatography/mass spectrometry. Antifungal and antibacterial activities of the oil and its fractions were assessed using microdilution method. Compounds γ-terpinene (48.07%), ρ-cymene (33.73%), and thymol (17.41%) were determined as major constituents. The effect of fraction II was better than total essential oil, fraction I, and standard thymol. The greater effect of fraction II compared to standard thymol showed the synergistic effects of the ingredients in this fraction. As this fraction and also total oil were effective on the studied microorganism, the combination of these products with current antimicrobial agents could be considered as new antimicrobial compounds in further investigations. © The Author(s) 2014.
Antimicrobial effects of essential oils in combination with chlorhexidine digluconate.

PubMed

Filoche, S K; Soma, K; Sissons, C H

2005-08-01

The aim of the present study was to compare antimicrobial effects of essential oils alone and in combination with chlorhexidine digluconate against planktonic and biofilm cultures of Streptococcus mutans and Lactobacillus plantarum. The essential oils included cinnamon, tea-tree (Melaleuca alternifola), manuka (Leptospermum scoparium), Leptospermum morrisonii, arnica, eucalyptus, grapefruit, the essential oil mouthrinse Cool Mint Listerine and two of its components, menthol and thymol. Cinnamon exhibited the greatest antimicrobial potency (1.25-2.5 mg/ml). Manuka, L. morrisonii, tea-tree oils, and thymol also showed antimicrobial potency but to a lesser extent. The combination effect of the essential oil-chlorhexidine was greater against biofilm cultures of both S. mutans and L. plantarum than against planktonic cultures. The amount of chlorhexidine required to achieve an equivalent growth inhibition against the biofilm cultures was reduced 4-10-fold in combination with cinnamon, manuka, L. morrisonii, thymol, and Listerine. We conclude that there may be a role for essential oils in the development of novel anticaries treatments.
Methyl Eugenol: Its Occurrence, Distribution, and Role in Nature, Especially in Relation to Insect Behavior and Pollination

PubMed Central

Tan, Keng Hong; Nishida, Ritsuo

2012-01-01

This review discusses the occurrence and distribution (within a plant) of methyl eugenol in different plant species (> 450) from 80 families spanning many plant orders, as well as various roles this chemical plays in nature, especially in the interactions between tephritid fruit flies and plants. PMID:22963669
Gene expression response of Salmonella enterica serotype Enteritidis phage type 8 to the subinhibitory concentrations of the plant-derived compounds,trans-cinnamaldehyde,and eugenol

USDA-ARS?s Scientific Manuscript database

Background: Salmonella Enteritidis phage type 8 (PT8) is a major poultry-associated Salmonella strain implicated in foodborne outbreaks in the United States. We previously reported that two GRAS-status, plant-derived compounds, trans-cinnamaldehyde (TC) and eugenol (EG) significantly reduced S. Ent...
Effect of therapeutic supplementation of plant molecules, trans-cinnamaldehyde and eugenol on Salmonella Enteritidis colonization in market-age broiler chickens

USDA-ARS?s Scientific Manuscript database

This study investigated the therapeutic efficacy of food-grade plant compounds, trans-cinnamaldehyde (TC) and eugenol (EG) on reducing SE in commercial, market-age broiler chickens. In two separate experiments, day-old commercial broiler chicks were randomly grouped into six groups of 14 birds each ...
Evolution of olfactory receptor in oriental fruit fly Dacus dorsalis

PubMed Central

Metcalf, Robert L.; Metcalf, Esther R.; Mitchell, W. C.; Lee, Lena W. Y.

1979-01-01

Male oriental fruit flies (Dacus dorsalis) from colonies in Taiwan and Hawaii were evaluated for limit of response to various analogues of methyl eugenol. The results are interpreted in terms of the geometry and allosteric requirements of the antennal receptor that triggers the characteristic methyl eugenol reflex. This receptor has evolved for complementarity to all portions of the methyl eugenol molecule and responds only to ortho-substituted benzenes with adjacent oxygen atoms or isoelectronic equivalents. Substantial differences in responses of Taiwan and Hawaiian D. dorsalis suggest that perceptible evolution of the receptor protein has occurred during the past 50 years. A plausible scheme for the coevolution of dacini flies with plants containing phenylpropionoid essential oils is outlined. Images PMID:16592640
Effectiveness of a novel spontaneous carvacrol nanoemulsion against Salmonella enterica Enteritidis and Escherichia coli O157:H7 on contaminated mung bean and alfalfa seeds.

PubMed

Landry, Kyle S; Chang, Yuhua; McClements, David Julian; McLandsborough, Lynne

2014-09-18

Outbreaks of foodborne illness from consumption of sprouts have been linked to contaminated seeds prior to germination. Due to the long sprouting period at ambient temperatures and high humidity, germinating seeds contaminated with low pathogen levels (0.1logCFU/g) can result in sprouts with high numbers (≥10(8)CFU/g) of pathogens. Currently, the recommended treatment method involves soaking seeds in 20,000ppm (2%) calcium hypochlorite prior to germination. In this study, an alternative treatment involving soaking seeds in a carvacrol nanoemulsion was tested for its efficacy against Salmonella enterica subspecies enterica serovar Enteritidis (ATCC BAA-1045) or EGFP expressing E. coli O157:H7 (ATCC 42895) contaminated mung bean and alfalfa seeds. The antimicrobial treatment was performed by soaking inoculated seed batches in the spontaneous nanoemulsion (4000 or 8000ppm) for 30 or 60min. The spontaneous nanoemulsion was formed by titrating the oil phase (carvacrol and medium chain triglycerides) and water-soluble surfactant (Tween 80®) into sodium citrate buffer. Following treatment, the numbers of surviving cells were determined by suspending the seeds in TSB and performing plate counts and/or Most Probable Number (MPN) enumeration. Treated seeds were sprouted and tested for the presence of the appropriate pathogen. This treatment successfully inactivated low levels (2 and 3logCFU/g) of S. Enteritidis and E. coli on either seed types when soaked for either 30 or 60min at nanoemulsion concentrations corresponding to 4000 (0.4%) or 8000 (0.8%) ppm carvacrol. Inoculated alfalfa seeds treated with 4000ppm nanoemulsion, required a 60min treatment time to show a similar 2-3 log reduction. Complete inactivation was confirmed by germinating treated seeds and performing microbiological testing. Total sprout yield was not compromised by any of the tested treatments. These results show that carvacrol nanoemulsions may be an alternative antimicrobial treatment method for mung bean and alfalfa seeds. Copyright © 2014 Elsevier B.V. All rights reserved.
Supercritical carbon dioxide extraction of compounds with antimicrobial activity from Origanum vulgare L.: determination of optimal extraction parameters.

PubMed

Santoyo, S; Cavero, S; Jaime, L; Ibañez, E; Señoráns, F J; Reglero, G

2006-02-01

Oregano leaves were extracted using a pilot-scale supercritical fluid extraction plant under a wide range of extraction conditions, with the goal of determining the extraction and fractionation conditions to obtain extracts with optimal antimicrobial activity. In this investigation, the essential oil-rich fractions were selectively precipitated in the second separator, and their chemical composition and antimicrobial activity were investigated. Gas chromatography-mass spectrometry analysis of the various fractions resulted in the identification of 27 compounds of the essential oil. The main components of these fractions were carvacrol, trans-sabinene hydrate, cis-piperitol, borneol, terpinen-4-ol, and linalool. Antimicrobial activity was investigated by the disk diffusion and broth dilution methods against six different microbial species, including two gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), two gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), a yeast (Candida albicans), and a fungus (Aspergillus niger). All of the supercritical fluid extraction fractions obtained showed antimicrobial activity against all of the microorganisms tested, although the most active fraction was the one obtained in experiment 5 (fraction was obtained with 7% ethanol at 150 bar and 40 degrees C). C. albicans was the most sensitive microorganism to the oregano extracts, whereas the least susceptible was A. niger. Carvacrol, sabinene hydrate, borneol, and linalool standards also showed antimicrobial activity against all of the microorganisms tested, with carvacrol being the most effective. Consequently, it was confirmed that essential oil from experiment 5, with the best antimicrobial activity, also presented the highest quantity of carvacrol.
[In vitro and in vivo recoveries of cutaneous micro-dialysis probe of paeonol, eugenol and piperine].

PubMed

Yang, Chang; Bai, Jie; Du, Shou-Ying; Cui, Ya-Hua; Zhang, Qin-Shuai; Ma, Jun-Ming

2016-11-01

To establish a method for detecting micro-dialysis recovery of paeonol, eugenol and piperine in Huoxue Zhitong patch, in order to provide the basis for further percutaneous pharmacokinetics studies. The concentrations of paeonol, eugenol and piperine in dialysates were determined by HPLC, and probe deliveries were calculated respectively. The effects of concentration and calibration approaches on the micro-dialysis probe deliveries of the three components were investigated, and their probe absorbability, in vitro and in vivo probe stability and repeatability were also studied.The results indicated that little paeonol, eugenol and piperine were observed in probes with 30% alcohol as the perfusate, and could be cleaned from probe in a short time. And the in vivo and in vitro probe deliveries of three components were stable within 8 h, drug-containing solution and blank perfusate were alternatively used for three times, and the in vivo and in vitro probe deliveries of three components were basically unchanged. The in vitro recoveries of paeonol, eugenol and piperine with a range of concentration were respectively (45.7±4.66)%, (27.82±2.95)%, (41.3±3.96)%, which indicated no concentration independent. Under the same conditions, the similar delivery was observed by dialysis, retrodialysis and no-net flux. Therefore, the concentrations of analyses of the collected fraction could be calibrated by in vitro or in vivo recoveries. Meanwhile, this also proved that the micro-dialysis method built by this study is applicable to the study on percutaneous pharmacokinetics of Huoxue Zhitong patch. Copyright© by the Chinese Pharmaceutical Association.
Effect of temporary cements on the microtensile bond strength of self-etching and self-adhesive resin cement.

PubMed

Carvalho, Edilausson Moreno; Carvalho, Ceci Nunes; Loguercio, Alessandro Dourado; Lima, Darlon Martins; Bauer, José

2014-11-01

The aim of this study was to evaluate the microtensile bond strength (µTBS) of self-etching and self-adhesive resin cement systems to dentin affected by the presence of remnants of either eugenol-containing or eugenol-free temporary cements. Thirty extracted teeth were obtained and a flat dentin surface was exposed on each tooth. Acrylic blocks were fabricated and cemented either with one of two temporary cements, one zinc oxide eugenol (ZOE) and one eugenol free (ZOE-free), or without cement (control). After cementation, specimens were stored in water at 37°C for 1 week. The restorations and remnants of temporary cements were removed and dentin surfaces were cleaned with pumice. Resin composite blocks were cemented to the bonded dentin surfaces with one of two resin cements, either self-etching (Panavia F 2.0) or self-adhesive (RelyX U-100). After 24 h, the specimens were sectioned to obtain beams for submission to µTBS. The fracture mode was evaluated under a stereoscopic loupe and a scanning electron microscope (SEM). Data from µTBS were submitted to two-way repeated-measure ANOVA and the Tukey test (alpha = 0.05). The cross-product interaction was statistically significant (p < 0.0003). The presence of temporary cements reduced the bond strength to Panavia self-etching resin cements only (p < 0.05). Fracture occurred predominantly at the dentin-adhesive interface. The presence of eugenol-containing temporary cements did not interfere in the bond strength to dentin of self-adhesive resin cements.
Effects and interactions of gallic acid, eugenol and temperature on thermal inactivation of Salmonella spp. in ground chicken

USDA-ARS?s Scientific Manuscript database

The combined effects of heating temperature (55 to 65C), gallic acid (0 to 2.0%), and eugenol (0 to 2.0%) on thermal inactivation of Salmonella in ground chicken were assessed. Thermal death times were determined in bags submerged in a heated water bath maintained at various set temperatures, follo...
Evaluation of attractive toxic sugar bait (ATSB)-barrier for control of vector and nuisance mosquitoes and its effect on non-target organisms in sub-tropical environments in Florida

USDA-ARS?s Scientific Manuscript database

We evaluated the efficacy of attractive toxic sugar baits (ATSB) in the laboratory and the field with the Environmental Protection Agency exempt active ingredient eugenol against vector and nuisance mosquitoes. In the laboratory, eugenol combined in attractive sugar bait (ASB) solution provided high...

Field trappping Bactrocera latifrons (Diptera: Tephritidae) with select eugenol analogs that have been found to attract other "nonresponsive" fruit fly species

USDA-ARS?s Scientific Manuscript database

Bactrocera latifrons (Hendel) (Diptera: Tephritidae) is a pest fruit fly species native to Oriental Asia which has invaded and established in Hawaii and Tanzania and has been recovered in detection trapping in California. It is largely non-responsive to the male lures cuelure and methyl eugenol. Alp...
Evaluation of antifungal activity in essential oil of the Syzygium aromaticum (L.) by extraction, purification and analysis of its main component eugenol

PubMed Central

Rana, Inder Singh; Rana, Aarti Singh; Rajak, Ram Charan

2011-01-01

Antifungal properties of some essential oils have been well documented. Clove oil is reported to have strong antifungal activity against many fungal species. In this study we have evaluated antifungal potential of essential oil of Syzygium aromaticum (L.) against some common fungal pathogens of plants and animals namely, Fusarium moniliforme NCIM 1100, Fusarium oxysporum MTCC 284, Aspergillus sp., Mucor sp., Trichophyton rubrum and Microsporum gypseum. All fungal species were found to be inhibited by the oil when tested through agar well diffusion method. Minimum inhibitory concentration (MIC) was determined for all the species. Column chromatography was performed to separate the eugenol rich fraction from clove oil. Out of seven fractions maximum activity was obtained in column fraction II. TLC and HPLC data confirmed presence of considerable Eugenol in fraction II and clove oil. Microscopic study on effect of clove oil and column fraction II on spores of Mucor sp. and M. gypseum showed distortion and shrinkage while it was absent in other column fractions. So it can be concluded that the antifungal action of clove oil is due to its high eugenol content. PMID:24031751
Acaricidal Activity of Eugenol Based Compounds against Scabies Mites

PubMed Central

Pasay, Cielo; Mounsey, Kate; Stevenson, Graeme; Davis, Rohan; Arlian, Larry; Morgan, Marjorie; Vyszenski-Moher, DiAnn; Andrews, Kathy; McCarthy, James

2010-01-01

Backgound Human scabies is a debilitating skin disease caused by the “itch mite” Sarcoptes scabiei. Ordinary scabies is commonly treated with topical creams such as permethrin, while crusted scabies is treated with topical creams in combination with oral ivermectin. Recent reports of acaricide tolerance in scabies endemic communities in Northern Australia have prompted efforts to better understand resistance mechanisms and to identify potential new acaricides. In this study, we screened three essential oils and four pure compounds based on eugenol for acaricidal properties. Methodology/Principal Findings Contact bioassays were performed using live permethrin-sensitive S. scabiei var suis mites harvested from pigs and permethrin-resistant S. scabiei var canis mites harvested from rabbits. Results of bioassays showed that clove oil was highly toxic against scabies mites. Nutmeg oil had moderate toxicity and ylang ylang oil was the least toxic. Eugenol, a major component of clove oil and its analogues –acetyleugenol and isoeugenol, demonstrated levels of toxicity comparable to benzyl benzoate, the positive control acaricide, killing mites within an hour of contact. Conclusions The acaricidal properties demonstrated by eugenol and its analogues show promise as leads for future development of alternative topical acaricides to treat scabies. PMID:20711455
Evaluation of antifungal activity in essential oil of the Syzygium aromaticum (L.) by extraction, purification and analysis of its main component eugenol.

PubMed

Rana, Inder Singh; Rana, Aarti Singh; Rajak, Ram Charan

2011-10-01

Antifungal properties of some essential oils have been well documented. Clove oil is reported to have strong antifungal activity against many fungal species. In this study we have evaluated antifungal potential of essential oil of Syzygium aromaticum (L.) against some common fungal pathogens of plants and animals namely, Fusarium moniliforme NCIM 1100, Fusarium oxysporum MTCC 284, Aspergillus sp., Mucor sp., Trichophyton rubrum and Microsporum gypseum. All fungal species were found to be inhibited by the oil when tested through agar well diffusion method. Minimum inhibitory concentration (MIC) was determined for all the species. Column chromatography was performed to separate the eugenol rich fraction from clove oil. Out of seven fractions maximum activity was obtained in column fraction II. TLC and HPLC data confirmed presence of considerable Eugenol in fraction II and clove oil. Microscopic study on effect of clove oil and column fraction II on spores of Mucor sp. and M. gypseum showed distortion and shrinkage while it was absent in other column fractions. So it can be concluded that the antifungal action of clove oil is due to its high eugenol content.
Development and Sequential Analysis of a New Multi-Agent, Anti-Acne Formulation Based on Plant-Derived Antimicrobial and Anti-Inflammatory Compounds.

PubMed

Saviuc, Crina; Ciubucă, Bianca; Dincă, Gabriela; Bleotu, Coralia; Drumea, Veronica; Chifiriuc, Mariana-Carmen; Popa, Marcela; Gradisteanu Pircalabioru, Gratiela; Marutescu, Luminita; Lazăr, Veronica

2017-01-17

The antibacterial and anti-inflammatory potential of natural, plant-derived compounds has been reported in many studies. Emerging evidence indicates that plant-derived essential oils and/or their major compounds may represent a plausible alternative treatment for acne, a prevalent skin disorder in both adolescent and adult populations. Therefore, the purpose of this study was to develop and subsequently analyze the antimicrobial activity of a new multi-agent, synergic formulation based on plant-derived antimicrobial compounds (i.e., eugenol, β-pinene, eucalyptol, and limonene) and anti-inflammatory agents for potential use in the topical treatment of acne and other skin infections. The optimal antimicrobial combinations selected in this study were eugenol/β-pinene/salicylic acid and eugenol/β-pinene/2-phenoxyethanol/potassium sorbate. The possible mechanisms of action revealed by flow cytometry were cellular permeabilization and inhibition of efflux pumps activity induced by concentrations corresponding to sub-minimal inhibitory (sub-MIC) values. The most active antimicrobial combination represented by salycilic acid/eugenol/β-pinene/2-phenoxyethanol/potassium sorbate was included in a cream base, which demonstrated thermodynamic stability and optimum microbiological characteristics.
Acute toxicity and repellent activity of the Origanum scabrum Boiss. & Heldr. (Lamiaceae) essential oil against four mosquito vectors of public health importance and its biosafety on non-target aquatic organisms.

PubMed

Govindarajan, Marimuthu; Kadaikunnan, Shine; Alharbi, Naiyf S; Benelli, Giovanni

2016-11-01

The recent outbreaks of dengue, chikungunya, and Zika virus highlighted the pivotal importance of mosquito vector control in tropical and subtropical areas worldwide. However, mosquito control is facing hot challenges, mainly due to the rapid development of pesticide resistance in Culicidae and the limited success of biocontrol programs on Aedes mosquitoes. In this framework, screening botanicals for their mosquitocidal potential may offer effective and eco-friendly tools in the fight against mosquitoes. In the present study, the essential oil (EO) obtained from the medicinal plant Origanum scabrum was analyzed by GC-MS and evaluated for its mosquitocidal and repellent activities towards Anopheles stephensi, Aedes aegypti, Culex quinquefasciatus, and Culex tritaeniorhynchus. GC-MS analysis showed a total of 28 compounds, representing 97.1 % of the EO. The major constituents were carvacrol (48.2 %) and thymol (16.6 %). The EO was toxic effect to the A. stephensi, A. aegypti, C. quinquefasciatus, and C. tritaeniorhynchus larvae, with LC 50 of 61.65, 67.13, 72.45, and 78.87 μg/ml, respectively. Complete ovicidal activity was observed at 160, 200, 240, and 280 μg/ml, respectively. Against adult mosquitoes, LD 50 were 122.38, 134.39, 144.53, and 158.87 μg/ml, respectively. In repellency assays, the EOs tested at 1.0, 2.5, and 5.0 mg/cm 2 concentration of O. scabrum gave 100 % protection from mosquito bites up to 210, 180, 150, and 120 min, respectively. From an eco-toxicological point of view, the EO was tested on three non-target mosquito predators, Gambusia affinis, Diplonychus indicus, and Anisops bouvieri, with LC 50 ranging from 4162 to 12,425 μg/ml. Overall, the EO from O. scabrum may be considered as a low-cost and eco-friendly source of phytochemicals to develop novel repellents against Culicidae.
Clinical and mycological evaluation of an herbal antifungal formulation in canine Malassezia dermatitis.

PubMed

Nardoni, S; Mugnaini, L; Pistelli, L; Leonardi, M; Sanna, V; Perrucci, S; Pisseri, F; Mancianti, F

2014-09-01

Malassezia pachydermatis is a common cause of more widespread dermatitis in dogs (CMD). Recurrences are common, and this disorder can be very troubling for both dogs and for the pet owner. The treatment of 20 dogs affected by dermatitis due to M. pachydermatis, with Malacalm(®), a commercially available mixture consisting of essential oils (Citrus aurantium 1%, Lavandula officinalis 1%, Origanum vulgare 0.5%, Origanum majorana 0.5%, Mentha piperita 0.5% and Helichrysum italicum var. italicum 0.5%, in sweet almond oil and coconut oil) is reported. The effectiveness of the whole mixture, of component essential oils and of their more represented compounds against clinical isolates was evaluated by a microdilution test. Twenty animals were topically administered the mixture twice daily for 1 month. Ten animals were treated with a conventional therapy based on ketoconazole 10mg/kg/day and chlorhexidine 2% twice a week for 3 weeks. At the end of both treatments animals significantly improved their clinical status. Adverse effects were never noticed. Follow-up visit performed on day 180th allowed to observe a recurrence of clinical signs in all the subjects treated conventionally, while not significant clinical changes were referred in dogs treated with Malacalm(®). The overall MIC value of Malacalm(®) was 0.3%. O. vulgare showed the lowest minimum inhibitory concentrations (MIC), being active at 0.8%, followed by M. piperita (1%), O. majorana (1.3%), C. aurantium (2%) and L. officinalis (4%) while H. italicum did not yield any antimycotic effect up to 10%. Active major compounds were thymol, carvacrol, p-cymene, 1,8-cineol, limonene and menthol. The phytotherapic treatment achieved a good clinical outcome, and no recurrence of skin disorders on day 180th was recorded. This herbal remedium appeared to be a safe tool for limiting recurrences of CMD. Copyright © 2014 Elsevier Masson SAS. All rights reserved.
Bergamot versus beetle: evidence for intraspecific chemical specialization

PubMed Central

Keefover-Ring, Ken

2015-01-01

A large proportion of phytophagous insects show host plant specificity (monophagy or oligophagy), often determined by host secondary chemistry. Yet, even specialists can be negatively affected by host chemistry at high levels or with novel compounds, which may manifest itself if their host species is chemically variable. This study tested for reciprocal effects of a specialist tortoise beetle (Physonota unipunctata) feeding on a host plant (Monarda fistulosa) with two monoterpene chemotypes [thymol (T) and carvacrol (C)] using a controlled field experiment where larvae fed on caged plants of both chemotypes, haphazardly collected natural plants with and without beetle damage, and growth chamber experiments where larvae that hatched and briefly fed on one chemotype were reared on either chemotype. In the field experiment, plant chemotype did not affect larval weight or length, but did influence larval survival with almost 8.3 % more surviving on T plants. Herbivores reduced seed head area (86.5 % decrease), stem mass (41.2 %) and stem height (21.1 %) of caged plants, but this was independent of host chemotype. Natural plants experienced similar reductions in these variables (74.0, 41.4 and 8.7 %) and T chemotypes were more frequently damaged. In the growth chamber, larval relative growth rate (RGR) differed for both feeding history and year. Larvae from T natal plants reared on T hosts grew at almost twice the rate of those from C and reared on T. Larvae from either T or C natal plants reared on C plants showed intermediate growth rates. Additional analyses revealed natal plant chemotype as the most important factor, with the RGR of larvae from T natal plants almost one-third higher than that of those from C natal plants. These cumulative results demonstrate intraspecific variation in plant resistance that may lead to herbivore specialization on distinct host chemistry, which has implications for the evolutionary trajectory of both the insect and plant species. PMID:26578745
Bergamot versus beetle: evidence for intraspecific chemical specialization.

PubMed

Keefover-Ring, Ken

2015-11-16

A large proportion of phytophagous insects show host plant specificity (monophagy or oligophagy), often determined by host secondary chemistry. Yet, even specialists can be negatively affected by host chemistry at high levels or with novel compounds, which may manifest itself if their host species is chemically variable. This study tested for reciprocal effects of a specialist tortoise beetle (Physonota unipunctata) feeding on a host plant (Monarda fistulosa) with two monoterpene chemotypes [thymol (T) and carvacrol (C)] using a controlled field experiment where larvae fed on caged plants of both chemotypes, haphazardly collected natural plants with and without beetle damage, and growth chamber experiments where larvae that hatched and briefly fed on one chemotype were reared on either chemotype. In the field experiment, plant chemotype did not affect larval weight or length, but did influence larval survival with almost 8.3 % more surviving on T plants. Herbivores reduced seed head area (86.5 % decrease), stem mass (41.2 %) and stem height (21.1 %) of caged plants, but this was independent of host chemotype. Natural plants experienced similar reductions in these variables (74.0, 41.4 and 8.7 %) and T chemotypes were more frequently damaged. In the growth chamber, larval relative growth rate (RGR) differed for both feeding history and year. Larvae from T natal plants reared on T hosts grew at almost twice the rate of those from C and reared on T. Larvae from either T or C natal plants reared on C plants showed intermediate growth rates. Additional analyses revealed natal plant chemotype as the most important factor, with the RGR of larvae from T natal plants almost one-third higher than that of those from C natal plants. These cumulative results demonstrate intraspecific variation in plant resistance that may lead to herbivore specialization on distinct host chemistry, which has implications for the evolutionary trajectory of both the insect and plant species. Published by Oxford University Press on behalf of the Annals of Botany Company.
Effect of Origanum chemotypes on broiler intestinal bacteria.

PubMed

Betancourt, Liliana; Rodriguez, Fernando; Phandanouvong, Vienvilay; Ariza-Nieto, Claudia; Hume, Michael; Nisbet, David; Afanador-Téllez, German; Van Kley, Alexandra Martynova; Nalian, Armen

2014-10-01

Essential oils have been proposed as alternatives to antibiotic use in food animal production. This study evaluated 3 chemotypes of the Origanum genus, containing varying amounts of secondary metabolites carvacrol, thymol, and sabinene, in the broiler chicken diet. Aerial parts of Origanum vulgare L. (OL), O. vulgare L. ssp. hirtum (OH), and O. majorana (OM) were collected from a greenhouse located in the high altitude Sabana de Bogotá (Savanna of Bogotá) and O. vulgare L. ssp. hirtum (OG) produced and ground in Greece. Oregano essential oils (OEO) from these plants were obtained by steam distillation and analyzed by gas chromatography coupled to a mass spectrometer. Six treatments were evaluated: 200 mg/kg of OEO from OH, OL, and OM, 50 mg/kg of OEO from OG, 500 mg/kg of chlortetracycline, and without additives. Broiler chicks were maintained at 2,600 m above sea level, placed in brooder cages under a completely randomized design. Template DNA was isolated from duodenal, jejunal, ileal, and cecal contents in each group and bacterial 16S rDNA patterns were analyzed by denaturing gradient gel electrophoresis. Dendrograms of denaturing gradient gel electrophoresis band patterns revealed 2 main clusters, OEO-treated chicks and nontreated control chicks, in each intestinal segment. Band patterns from different gut compartments revealed major bacterial population shifts in the foregut (duodenum, jejunum, and ileum) compared with the hindgut (cecum and colon) at all ages evaluated (P < 0.05). The OEO groups showed less shift (62.7% similarity coefficient) between these 2 compartments versus the control groups (53.7% similarity coefficient). A reduction of 59% in mortality from ascites was seen in additive-supplemented groups compared with the control group. This study represents the first work to evaluate the effects of the 3 main chemotypes of Origanum genus in broilers. ©2014 Poultry Science Association Inc.
Comparative efficacies of Zataria multiflora essential oil and itraconazole against disseminated Candida albicans infection in BALB/c mice

PubMed Central

Khosravi, A.R.; Shokri, H.; Tootian, Z.; Alizadeh, M.; Yahyaraeyat, R.

2009-01-01

Disseminated candidiasis is a serious problem in public health that results from the invasion of Candida species, in particular Candida albicans. The aim of this study was to compare the efficacies of Zataria multiflora essential oil and itraconazole in clearing C. albicans from the visceral organs of BALB/c mice suffered from disseminated candidiasis. Zataria multiflora essential oil was extracted using Clevenger-type apparatus and analyzed by gas chromatography mass spectrometry (GC-MS). For clearance experiment, mice (20-25 g, N=8 per group) received essential oil at doses of 30, 48 and 64 mg/kg and itraconazole at dose of 200 mg/kg intraperitoneally (IP) 2 days before and after intravenous inoculation of 0.5 × 106 C. albicans blastospores. The treated animals were sacrificed on day 20, and 0.1 g of the tissue homogenates was plated onto specific media. In GC-Mass, the main components of the essential oil were carvacrol (61.29%) and thymol (25.18%). The results demonstrated that IP administration of 64 mg/kg of the essential oil had the highest efficacy in reducing C. albicans and produced 39.5, 21.8, 141.5, 174 and 501-fold reductions in mean CFUs per 0.1 gram in Candida infections of the liver, spleen, lungs, brain and kidneys, respectively, compared to positive control. Itraconazole showed significantly more responsiveness than the essential oil at dose of 30 mg/kg in clearing C. albicans from the kidneys (P<0.02), brain (P<0.02) and spleen (P<0.04), and less responsiveness than that of 64 mg/kg in clearing the organism from the brain (P<0.01), lungs (P<0.0005) and kidneys (P<0.0005), whereas no significant difference was observed between this drug and Z. multiflora at dose of 48 mg/kg. These data explain the increased rate of yeast clearance and reduced dissemination to the viscera of Z. multiflora treated mice. PMID:24031384
Chemical composition and antioxidant properties of clove leaf essential oil.

PubMed

Jirovetz, Leopold; Buchbauer, Gerhard; Stoilova, Ivanka; Stoyanova, Albena; Krastanov, Albert; Schmidt, Erich

2006-08-23

The antioxidant activity of a commercial rectified clove leaf essential oil (Eugenia caryophyllus) and its main constituent eugenol was tested. This essential oil comprises in total 23 identified constituents, among them eugenol (76.8%), followed by beta-caryophyllene (17.4%), alpha-humulene (2.1%), and eugenyl acetate (1.2%) as the main components. The essential oil from clove demonstrated scavenging activity against the 2,2-diphenyl-1-picryl hydracyl (DPPH) radical at concentrations lower than the concentrations of eugenol, butylated hydroxytoluene (BHT), and butylated hydroxyanisole (BHA). This essential oil also showed a significant inhibitory effect against hydroxyl radicals and acted as an iron chelator. With respect to the lipid peroxidation, the inhibitory activity of clove oil determined using a linoleic acid emulsion system indicated a higher antioxidant activity than the standard BHT.
Antioxidant Activity of the Essential Oil and its Major Terpenes of Satureja macrostema (Moc. and Sessé ex Benth.) Briq.

PubMed Central

Torres-Martínez, Rafael; García-Rodríguez, Yolanda Magdalena; Ríos-Chávez, Patricia; Saavedra-Molina, Alfredo; López-Meza, Joel Edmundo; Ochoa-Zarzosa, Alejandra; Garciglia, Rafael Salgado

2017-01-01

Background: The aim of this study was to investigate the in vitro antioxidant activity of Satureja macrostema (Moc. and Sessé ex Benth.) Briq. (Lamiaceae) essential oil, a Mexican medicinal plant known as nurite. Materials and Methods: Fresh aerial parts of S. macrostema plants cultivated in greenhouse for 3 months were subjected to hydrodistillation in a Clevenger apparatus to obtain essential oil. Volatile compounds were identified by gas chromatography (GC) and GC/mass spectrometry. Antioxidant effectiveness of essential oil and its major terpenes of S. macrostema was examined by three different radical scavenging methods: 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2’-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), and total antioxidant capacity (TAC). The concentrations tested were 0.001, 0.01, 0.1, and 1 mg/mL. Results: The major volatile compounds were caryophyllene, limonene, linalool, pulegone, menthone, and thymol. S. macrostema essential oil showed the highest free radical scavenging activity with DPPH and ABTS methods (53.10% and 92.12%, respectively) at 1 mg/mL and 98% with TAC method at 0.1 mg/mL. Thymol exerted the highest antioxidant capacity with 0.1 mg/mL, reaching 83.38%, 96.96%, and 98.57% by DPPH, ABTS, and TAC methods. Caryophyllene, limonene, linalool, pulegone, and menthone exhibited an antioxidant capacity <25% with the DPPH and ABTS methods; however, limonene showed a TAC of 85.41% with 0.01 mg/mL. Conclusion: The essential oil of S. macrostema and thymol showed a free radical scavenging activity close to that of the synthetic butylated hydroxytoluene. SUMMARY The major volatile compounds of essential oil of Satureja macrostema were caryophyllene, limonene, linalool, pulegone, menthone and thymolThe essential oil of S. macrostema showed a high free radical scavengingThymol exerted the highest antioxidant capacity by DPPH, ABTS and TAC methods. Abbreviations used: GC: Gas Chromatography; DPPH: 2,2-diphenyl-1-picrylhydrazyl; ABTS: 2,2’-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid; TAC: Total antioxidant capacity. PMID:29491647
Evaluation of essential oils in beef cattle manure slurries and applications of select compounds to beef feedlot surfaces to control zoonotic pathogens.

PubMed

Wells, J E; Berry, E D; Guerini, M N; Varel, V H

2015-02-01

To evaluate natural terpene compounds for antimicrobial activities and determine whether these compounds could be used to control microbial activities and pathogens in production animal facilities. Thymol, geraniol, glydox, linalool, pine oil, plinol and terpineol were tested in laboratory studies for ability to control the production of odorous volatile fatty acid compounds and reduce pathogen levels in manure slurry preparations. Thymol is a terpene phenolic compound and was most effective for reducing fermentation products and pathogen levels (P < 0.05), followed by the extracts linalool, pine oil and terpineol, which are terpene alcohols. Select compounds thymol, linalool and pine oil were further evaluated in two separate studies by applying the agents to feedlot surfaces in cattle pens. Feedlot surface material (FSM; manure and soil) was collected and analysed for fermentation products, levels of coliforms and total Escherichia coli, and the presence of E. coli O157:H7, Campylobacter, Salmonella, Listeria and L. monocytogenes. The reduction in fermentation products but not pathogens was dependent on the moisture present in the FSM. Treatment with 2000 ppm thymol reduced the prevalence of E. coli O157:H7 but not Listeria. In a separate study, treatment with 4000 ppm pine oil reduced E. coli O157:H7, Listeria and Campylobacter (P < 0.05). Linalool was tested at two levels (2000 and 4000 ppm) and did not affect pathogen levels at either concentration. Natural compounds bearing terpenes can control pathogenic bacteria in treated manures and when applied to the feedlot surface in production cattle systems. Pine oil is a cheaper alternative to thymol and may be a useful treatment for controlling pathogens. The control of bacterial pathogens in animal productions systems is an important step in preharvest food safety. Waste products, such as pine oil extract, from the pulp wood industry may have application for treating feedlot pens and manures to reduce the pathogen load. Published 2014. This article is a U.S. Government work and is in the public domain in the USA.
Field trials of solid triple lure (trimedlure, methyl eugenol, raspberry ketone, and DDVP) dispensers for detection and male annihilation of Ceratitis capitata (Wiedemann), Bactrocera dorsalis (Hendel) and Bactrocera cucurbit

USDA-ARS?s Scientific Manuscript database

Solid Mallet TMR (trimedlure [TML], methyl eugenol [ME], raspberry ketone [RK]) wafers and Mallet CMR (ceralure, ME, RK, benzyl acetate) wafers impregnated with DDVP insecticide were evaluated in traps as potential detection and male annihilation devices. Comparisons were made with 1) liquid lure a...
Weathering and chemical degradation of methyl eugenol and raspberry ketone solid dispensers for detection, monitoring and male annihilation of Bactrocera dorsalis and Bactrocera cucurbitae (Diptera: Tephritidae) in Hawaii

USDA-ARS?s Scientific Manuscript database

Solid male lure dispensers containing methyl eugenol (ME) and raspberry ketone (RK), or mixtures of the lures (ME + RK), and dimethyl dichloro-vinyl phosphate (DDVP) were evaluated in AWPM bucket or Jackson traps in commercial papaya (Carica papaya L.) orchards where both oriental fruit fly, Bactroc...
Determination of free and glucosidically-bound volatiles in plants. Two case studies: L-menthol in peppermint (Mentha x piperita L.) and eugenol in clove (Syzygium aromaticum (L.) Merr. & L.M.Perry).

PubMed

Sgorbini, Barbara; Cagliero, Cecilia; Pagani, Alberto; Sganzerla, Marla; Boggia, Lorenzo; Bicchi, Carlo; Rubiolo, Patrizia

2015-09-01

This study arises from both the today's trend towards exploiting plant resources exhaustively, and the wide quantitative discrepancy between the amounts of commercially-valuable markers in aromatic plants and those recovered from the related essential oil. The study addresses the determination of both the qualitative composition and the exhaustive distribution of free and glucosidically-bound L-menthol in peppermint aerial parts (Mentha x piperita L., Lamiaceae) and of eugenol in dried cloves (Syzygium aromaticum (L.) Merr. & L.M.Perry, Myrtaceae), two plants known to provide widely ranging essential oil yields. The two markers were investigated in essential oils and residual hydrodistillation waters, before and after enzymatic hydrolysis. Their amounts were related to those in the headspace taken as reference. The results showed that the difference between marker compound in headspace and in essential oil amounted to 22.8% for L-menthol in peppermint, and 16.5% for eugenol in cloves. The aglycones solubilised in the residual hydrodistillation waters were 7.2% of the headspace reference amount for L-menthol, and 13.3% for eugenol, respectively representing 9.3% and 15.9% of their amounts in the essential oil. The amount of L-menthol from its glucoside in residual hydrodistillation waters was 20.6% of that in the related essential oil, while eugenol from its glucoside accounted for 7.7% of the amount in clove essential oil. The yield of L-menthol, after submitting the plant material to enzymatic hydrolysis before hydrodistillation, increased by 23.1%, and for eugenol the increase was 8.1%, compared to the amount in the respective conventional essential oils. This study also aimed to evaluate the reliability of recently-introduced techniques that are little applied, if at all, in this field. The simultaneous use of high-concentration-capacity sample preparation techniques (SBSE, and HS-SPME and in-solution SPME) to run quali-quantitative analysis without sample manipulation, and direct LC-MS glucoside analysis, provided cross-validation of the results. Copyright © 2015 Elsevier Ltd. All rights reserved.
Thymus vulgaris L. and thymol assist murine macrophages (RAW 264.7) in the control of in vitro infections by Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albicans.

PubMed

de Oliveira, Jonatas Rafael; Figueira, Leandro Wagner; Sper, Fábia Lugli; Meccatti, Vanessa Marques; Camargo, Samira Esteves Afonso; de Oliveira, Luciane Dias

2017-08-01

Microorganisms are capable to combat defense cells by means of strategies that contribute to their stabilization and proliferation in invaded tissues. Frequently antimicrobial-resistant strains appear; therefore, alternative methods to control them must be investigated, for example, the use of plant products. The capacity of the thyme extract (Thymus vulgaris L.) and phytocompound thymol in the control of in vitro infections by Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albicans in murine macrophages (RAW 264.7) was evaluated. Minimal inhibitory concentrations (MIC) of the plant products were used. The effect of these MIC were analyzed in the assays of phagocytosis and immunoregulation by analysis of the production of cytokines (IL-1β, TNF-α, and IL-10) and nitric oxide (NO). The plant products effectively assisted the macrophages in the phagocytosis of microorganisms, presenting significant reductions of S. aureus and P. aeruginosa. The macrophages also regulated the production of inflammatory mediators in the infections by S. aureus, P. aeruginosa, and C. albicans. In addition, thyme provided a satisfactory effect in response to the bacterial infections, regarding generation of NO. Thus, the effectiveness of the thyme and thymol to control in vitro infections by S. aureus, P. aeruginosa, and C. albicans was observed. Phagocytosis of S. aureus by RAW 264.7 was enhanced with thymol Thyme enhanced the phagocytosis of P. aeruginosa by RAW 264.7 Plant products provided immunoregulation of inflammatory cytokines Production of nitric oxide was improved with the treatments in bacterial infections.
Development and evaluation of thymol-chitosan hydrogels with antimicrobial-antioxidant activity for oral local delivery.

PubMed

Alvarez Echazú, María Inés; Olivetti, Christian Ezequiel; Anesini, Claudia; Perez, Claudio Javier; Alvarez, Gisela Solange; Desimone, Martin Federico

2017-12-01

Nowadays, the research of innovative drug delivery devices is focused on the design of multiple drug delivery systems, the prevention of drug side effects and the reduction of dosing intervals. Particularly, new mucosal delivery systems for antimicrobials, antioxidants and anti-inflammatory drugs has a growing development, regards to the avoidance of side effects, easy administration and a suitable drug concentration in the mucosa. In this work, chitosan hydrogels are evaluated as a biodegradable scaffold and as a bioactive agent carrier of an antioxidant-antimicrobial compound called thymol. Throughout the study, swelling behavior, viscoelastic properties and thermal analysis are highlighted to present its advantages for a biomedical application. Furthermore, the in vitro results obtained indicate that thymol-chitosan hydrogels are biocompatible when exposed to [3T3] fibroblasts, exhibit antimicrobial activity against Staphylococcus aureus and Streptococcus mutans for 72h and antioxidant activity for 24h. These are desirable properties for a mucosal delivery system for an antimicrobial-antioxidant dual therapy for periodontal disease. Copyright © 2017 Elsevier B.V. All rights reserved.
Microbial transformation of citral by Penicillium sp..

PubMed

Esmaeili, Akbar; Tavassoli, Afsaneh

2010-01-01

Thymol is present in the essential oils from herbs and spices, such as thyme. It is produced by these plant species as a chemical defense against phytopathogenic microorganisms. Therefore, this compound has attracted great attention in food industry, i.e., it has been used as a natural preservative in foods such as cheese to prevent fungal growth. Previous studies concerning the biotransformation of nerol by Penicillium sp. and microbial transformation of citral by sporulated surface cultures method (SSCM) of Penicillium digitatum have been reported. The objective of this research was to study the pathway involved during biotransformation of citral by Penicillium sp. using two methods. The culture preparation was done using different microbial methods and incubation periods to obtain Penicillium for citral biotransformation. The biotransformation products were identified by gas chromatography (GC) and gas chromatography/mass spectroscopy (GC/MS). A comparison of the two methods showed that SSCM was more effective, its major products were thymol (21.5 %), geranial (18.6 %) and nerol (13.7 %). LM produced only one compound — thymol — with a low efficiency.

Plant Essential Oils Synergize and Antagonize Toxicity of Different Conventional Insecticides against Myzus persicae (Hemiptera: Aphididae)

PubMed Central

Faraone, Nicoletta; Hillier, N. Kirk; Cutler, G. Christopher

2015-01-01

Plant-derived products can play an important role in pest management programs. Essential oils from Lavandula angustifolia (lavender) and Thymus vulgaris (thyme) and their main constituents, linalool and thymol, respectively, were evaluated for insecticidal activity and synergistic action in combination with insecticides against green peach aphid, Myzus persicae (Sulzer) (Hemiptera: Aphididae). The essential oils and their main constituents exerted similar insecticidal activity when aphids were exposed by direct sprays, but were non-toxic by exposure to treated leaf discs. In synergism experiments, the toxicity of imidacloprid was synergized 16- to 20-fold by L. angustifolia and T. vulgaris essential oils, but far less synergism occurred with linalool and thymol, indicating that secondary constituents of the oils were probably responsible for the observed synergism. In contrast to results with imidacloprid, the insecticidal activity of spirotetramat was antagonized by L. angustifolia and T. vulgaris essential oils, and linalool and thymol. Our results demonstrate the potential of plant essential oils as synergists of insecticides, but show that antagonistic action against certain insecticides may occur. PMID:26010088
Dietary Supplementation of Benzoic Acid and Essential Oil Compounds Affects Buffering Capacity of the Feeds, Performance of Turkey Poults and Their Antioxidant Status, pH in the Digestive Tract, Intestinal Microbiota and Morphology

PubMed Central

Giannenas, I.; Papaneophytou, C. P.; Tsalie, E.; Pappas, I.; Triantafillou, E.; Tontis, D.; Kontopidis, G. A.

2014-01-01

Three trials were conducted to evaluate the effect of supplementation of a basal diet with benzoic acid or thymol or a mixture of essential oil blends (MEO) or a combination of benzoic acid with MEO (BMEO) on growth performance of turkey poults. Control groups were fed a basal diet. In trial 1, benzoic acid was supplied at levels of 300 and 1,000 mg/kg. In trial 2, thymol or the MEO were supplied at levels of 30 mg/kg. In trial 3, the combination of benzoic acid with MEO was evaluated. Benzoic acid, MEO and BMEO improved performance, increased lactic acid bacteria populations and decreased coliform bacteria in the caeca. Thymol, MEO and BMEO improved antioxidant status of turkeys. Benzoic acid and BMEO reduced the buffering capacity compared to control feed and the pH values of the caecal content. Benzoic acid and EOs may be suggested as an effective alternative to AGP in turkeys. PMID:25049947
In vitro effects of some herbs used in Egyptian traditional medicine on viability of protoscolices of hydatid cysts.

PubMed

Yones, Doaa A; Taher, Gamal A; Ibraheim, Zedan Z

2011-09-01

The present work evaluated the effects of alcoholic extracts of salvia (Salvia officinalis), thyme (Thymus vulgaris), and 2 pure compounds (thymol and menthol) on the viability of Echinococcus granulosus protoscolices in vitro. Four different concentrations of each extract (2,500, 1,500, 1,000, and 500 µg/ml) and 3 different concentrations each of thymol and menthol (50, 10, and 1 µg/ml) were used. Concentration of 2,500 µg/ml of both extracts showed a significant protoscolicidal activity on the 6th day. Complete loss of viability of protoscolices occurred with 500 µg/ml concentration of both extracts at day 6 and day 7 post-treatment (PT), respectively. Pure compounds, i.e., menthol and thymol, showed potent effects with 50 µg/ml concentration at day 2 and day 5 PT, respectively. These effects were compared with those of albendazole sulfoxide (800 µg/ml), a commonly used treatment drug for hydatidosis. Krebs-Ringer solution and the hydatid cystic fluid at a ratio of 4:1 was a good preservative solution which kept the protoscolices viable for 15 days.
Increasing antioxidant activity and reducing decay of blueberries by essential oils.

PubMed

Wang, Chien Y; Wang, Shiow Y; Chen, Chitsun

2008-05-28

Several naturally occurring essential oils including carvacrol, anethole, cinnamaldehyde, cinnamic acid, perillaldehyde, linalool, and p-cymene were evaluated for their effectiveness in reducing decay and increasing antioxidant levels and activities in 'Duke' blueberries ( Vaccinium corymbosum). Carvacrol, anethole, and perillaldehyde showed the capability to promote total anthocyanins and total phenolics and enhance antioxidant activity in fruit tissues expressed as oxygen radical absorbance capacity (ORAC) and hydroxyl radical ( (*)OH) scavenging capacity. All of the essential oils tested in this study were able to inhibit fruit decay development to some degree compared to controls. The most effective compound for mold retardation was p-cymene, followed by linalool, carvacrol, anethole, and perillaldehyde. Cinnamic acid and cinnamaldehyde also suppressed mold growth, but to a lesser extent. Treatment with carvacrol, anethole, or perillaldehyde also significantly increased the levels of fructose, glucose, and citric acid. Individual flavonoids were variably affected by the essential oils. Levels of chlorogenic acid, which was the major phenolic compound in blueberry fruit, were enhanced by all of the essential oils in this study. Increased amounts of quercetin 3-galactoside and quercetin 3-arabinoside were also found in all treated fruit except samples treated with linalool or p-cymene. The major anthocyanin, malvidin 3-galactoside, was enhanced by all essential oils tested except linalool and p-cymene. The levels of other individual anthocyanins including petunidin 3-galactoside, delphinidin 3-galactoside, petunidin 3-glucoside, petunidin 3-arabinoside, delphinidin 3-arabinoside, and cyanidin 3-galactoside were higher in treated fruit compared to controls. Those essential oils that have positive effects on enhancing anthocyanins, phenolic compounds, and antioxidant activity of fruit, but inhibitory effects on microbial growth and decay development, deserve further evaluation.
In vitro inhibition of Eimeria tenella invasion of epithelial cells by phytochemicals.

PubMed

Burt, S A; Tersteeg-Zijderveld, M H G; Jongerius-Gortemaker, B G M; Vervelde, L; Vernooij, J C M

2013-01-31

Resistance to coccidiostats and possible future restrictions on their use raise the need for alternative methods of reducing coccidiosis in poultry. The aim of this study was to evaluate the effect of selected phytochemicals on Eimeria tenella sporozoite invasion in vitro. Four phytochemicals were selected on the basis that they reduce the virulence of Eimeria spp. and/or provide immune modulatory benefits to host cells: betaine, carvacrol, curcumin and Echinacea purpurea extract (EP). Madin-Darby bovine kidney (MDBK) cells were covered by medium containing phytochemicals at the highest concentration which was non-toxic to the cells. Salinomycin 50 μg/ml was positive control; negative control was medium only. E. tenella (Houghton strain) sporozoites were added to wells and after incubation for 2, 4 or 20 h at 37°C, cells were fixed and stained with hematoxylin-eosin. Ten evenly spaced fields per well were photographed and the percentage of cells invaded by sporozoites was calculated and normalized to the control. At 2h, carvacrol, curcumin and EP showed a significantly lower percentage of sporozoite invasion than the untreated control; in contrast, betaine treatment represented a significantly higher invasion percentage. Combining carvacrol with EP inhibited E. tenella invasion more effectively than applying the compounds individually, but the further addition of curcumin did not reduce invasion further. In conclusion, this study shows that invasion of MDBK epithelial cells by E. tenella sporozoites is inhibited in the presence of carvacrol, curcumin, or EP and enhanced by betaine. There may be potential for developing these phytochemicals as anti-coccidial feed or water additives for poultry. Copyright © 2012 Elsevier B.V. All rights reserved.
Soil Microorganisms Alleviate the Allelochemical Effects of a Thyme Monoterpene on the Performance of an Associated Grass Species

PubMed Central

Ehlers, Bodil K.

2011-01-01

Background Plant allelochemicals released into the soil can significantly impact the performance of associated plant species thereby affecting their competitive ability. Soil microbes can potentially affect the interaction between plant and plant chemicals by degrading the allelochemicals. However, most often plant-plant chemical interactions are studied using filter paper bioassays examining the pair-wise interaction between a plant and a plant chemical, not taking into account the potential role of soil microorganisms. Methodology/Principal findings To explore if the allelopathic effects on a grass by the common thyme monoterpene “carvacrol” are affected by soil microorganisms. Seedlings of the grass Agrostis capillaris originating from 3 different thyme sites were raised in the greenhouse. Seedlings were grown under four different soil treatments in a 2*2 fully factorial experiment. The monoterpene carvacrol was either added to standard greenhouse soil or left out, and soil was either sterilized (no soil microorganisms) or not (soil microorganisms present in soil). The presence of carvacrol in the soil strongly increased mortality of Agrostis plants, and this increase was highest on sterile soil. Plant biomass was reduced on soil amended with carvacrol, but only when the soil was also sterilized. Plants originating from sites where thyme produces essential oils containing mostly carvacrol had higher survival on soil treated with that monoterpene than plants originating from a site where thyme produced different types of terpenes, suggesting an adaptive response to the locally occurring terpene. Conclusions/Significance The study shows that presence of soil microorganisms can alleviate the negative effect of a common thyme monoterpene on the performance of an associated plant species, emphasizing the role of soil microbes in modulating plant-plant chemical interactions. PMID:22125596
Carvacrol suppresses high pressure high temperature inactivation of Bacillus cereus spores.

PubMed

Luu-Thi, Hue; Corthouts, Jorinde; Passaris, Ioannis; Grauwet, Tara; Aertsen, Abram; Hendrickx, Marc; Michiels, Chris W

2015-03-16

The inactivation of bacterial spores generally proceeds faster and at lower temperatures when heat treatments are conducted under high pressure, and high pressure high temperature (HPHT) processing is, therefore, receiving an increased interest from food processors. However, the mechanisms of spore inactivation by HPHT treatment are poorly understood, particularly at moderately elevated temperature. In the current work, we studied inactivation of the spores of Bacillus cereus F4430/73 by HPHT treatment for 5 min at 600MPa in the temperature range of 50-100°C, using temperature increments of 5°C. Additionally, we investigated the effect of the natural antimicrobial carvacrol on spore germination and inactivation under these conditions. Spore inactivation by HPHT was less than about 1 log unit at 50 to 70°C, but gradually increased at higher temperatures up to about 5 log units at 100°C. DPA release and loss of spore refractility in the spore population were higher at moderate (≤65°C) than at high (≥70°C) treatment temperatures, and we propose that moderate conditions induced the normal physiological pathway of spore germination resulting in fully hydrated spores, while at higher temperatures this pathway was suppressed and replaced by another mechanism of pressure-induced dipicolinic acid (DPA) release that results only in partial spore rehydration, probably because spore cortex hydrolysis is inhibited. Carvacrol strongly suppressed DPA release and spore rehydration during HPHT treatment at ≤65°C and also partly inhibited DPA release at ≥65°C. Concomitantly, HPHT spore inactivation was reduced by carvacrol at 65-90°C but unaffected at 95-100°C. Copyright © 2014 Elsevier B.V. All rights reserved.
An experimental evaluation of the anti-atherogenic potential of the plant, Piper betle, and its active constitutent, eugenol, in rats fed an atherogenic diet.

PubMed

Venkadeswaran, Karuppasamy; Thomas, Philip A; Geraldine, Pitchairaj

2016-05-01

Hypercholesterolemia is a major risk factor for systemic atherosclerosis and subsequent cardiovascular disease. Lipoperoxidation-mediated oxidative damage is believed to contribute strongly to the progression of atherogenesis. In the current investigation, putative anti-atherogenic and antioxidative properties of an ethanolic extract of Piper betle and of its active constituent, eugenol, were sought in an experimental animal model of chronic hypercholesterolemia. Atherogenic diet-fed rats that received either Piper betle extract orally (500mg/kg b.wt) or eugenol orally (5mg/kg b.wt) for 15days (commencing 30days after the atherogenic diet had been started) exhibited the following variations in different parameters, when compared to atherogenic diet-fed rats that received only saline: (1) significantly lower mean levels of total cholesterol, triglycerides, low-density lipoprotein cholesterol and very low density lipoprotein cholesterol in both serum and hepatic tissue samples; (2) lower mean serum levels of aspartate amino-transferase, alanine amino-transferase, alkaline phosphatase, lactate dehydrogenase and lipid-metabolizing enzymes (lipoprotein lipase, 3-hydroxy-3-methyl-glutaryl-CoA reductase; (3) significantly lower mean levels of enzymatic antioxidants (catalase, superoxide dismutase, glutathione peroxidase, glutathione-S-transferase) and non-enzymatic antioxidants (reduced glutathione, vitamin C and vitamin E) and significantly higher mean levels of malondialdehyde in haemolysate and hepatic tissue samples. Histopathological findings suggested a protective effect of the Piper betle extract and a more pronounced protective effect of eugenol on the hepatic and aortic tissues of atherogenic diet-fed (presumed atherosclerotic) rats. These results strongly suggest that the Piper betle extract and its active constituent, eugenol, exhibit anti-atherogenic effects which may be due to their anti-oxidative properties. Copyright © 2016 Elsevier Masson SAS. All rights reserved.
Insecticidal activity of basil oil, trans-anethole, estragole, and linalool to adult fruit flies of Ceratitis capitata, Bactrocera dorsalis, and Bactrocera cucurbitae.

PubMed

Chang, Chiou Ling; Cho, Il Kyu; Li, Qing X

2009-02-01

Basil oil and its three major active constituents (trans-anethole, estragole, and linalool) obtained from basil (Oscimum basilicum L.) were tested on three tephritid fruit fly species [Ceratitis capitata (Wiedemann), Bactrocera dorsalis (Hendel), and Bactrocera cucurbitae (Coquillett)] for insecticidal activity. All test chemicals acted fast and showed a steep dose-response relationship. The lethal times for 90% mortality/knockdown (LT90) of the three fly species to 10% of the test chemicals were between 8 and 38 min. The toxic action of basil oil in C. capitata occurred significantly faster than in B. cucurbitae but slightly faster than in B. dorsalis. Estragole acted faster in B. dorsalis than in C. capitata and B. cucurbitae. Linalool action was faster in B. dorsalis and C. capitata than in B. cucurbitae. trans-Anethole action was similar to all three species. Methyl eugenol acted faster in C. capitata and B. cucurbitae than in B. dorsalis. When linalool was mixed with cuelure (attractant to B. cucurbitae male), its potency to the three fly species decreased as the concentration of cuelure increased. This was due to linalool hydrolysis catalyzed by acetic acid from cuelure degradation, which was confirmed by chemical analysis. When methyl eugenol (B. dorsalis male attractant) was mixed with basil oil, trans-anethole, estragole, or linalool, it did not affect the toxicity of basil oil and linalool to B. dorsalis, but it did significantly decrease the toxicity of trans-anethole and estragole. Structural similarity between methyl eugenol and trans-anethole and estragole suggests that methyl eugenol might act at a site similar to that of trans-anethole and estragole and serve as an antagonist if an action site exists. Methyl eugenol also may play a physiological role on the toxicity reduction.
Inhibitory Effect of Essential Oils on Aspergillus ochraceus Growth and Ochratoxin A Production

PubMed Central

Selvaraj, Jonathan Nimal; Wang, Yan; Zhao, Yueju; Zhou, Lu; Liu, Xiao; Liu, Yang

2014-01-01

Ochratoxin A (OTA) is a mycotoxin which is a common contaminant in grains during storage. Aspergillus ochraceus is the most common producer of OTA. Essential oils play a crucial role as a biocontrol in the reduction of fungal contamination. Essential oils namely natural cinnamaldehyde, cinnamon oil, synthetic cinnamaldehyde, Litsea citrate oil, citral, eugenol, peppermint, eucalyptus, anise and camphor oils, were tested for their efficacy against A. ochraceus growth and OTA production by fumigation and contact assays. Natural cinnamaldehyde proved to be the most effective against A. ochraceus when compared to other oils. Complete fungal growth inhibition was obtained at 150–250 µL/L with fumigation and 250–500 µL/L with contact assays for cinnamon oil, natural and synthetic cinnamaldehyde, L. citrate oil and citral. Essential oils had an impact on the ergosterol biosynthesis and OTA production. Complete inhibition of ergosterol biosynthesis was observed at ≥100 µg/mL of natural cinnamaldehyde and at 200 µg/mL of citral, but total inhibition was not observed at 200 µg/mL of eugenol. But, citral and eugenol could inhibit the OTA production at ≥75 µg/mL and ≥150 µg/mL respectively, while natural cinnamaldehyde couldn’t fully inhibit OTA production at ≤200 µg/mL. The inhibition of OTA by natural cinnamaldehyde is mainly due to the reduction in fungal biomass. However, citral and eugenol could significant inhibit the OTA biosynthetic pathway. Also, we observed that cinnamaldehyde was converted to cinnamic alcohol by A. ochraceus, suggesting that the antimicrobial activity of cinnamaldehyde was mainly attributed to its carbonyl aldehyde group. The study concludes that natural cinnamaldehyde, citral and eugenol could be potential biocontrol agents against OTA contamination in storage grains. PMID:25255251
Appetite-enhancing effects of vanilla flavours such as vanillin.

PubMed

Ogawa, Kakuyou; Tashima, Akira; Sadakata, Momoko; Morinaga, Osamu

2018-06-01

Vanilla flavour is familiar to consumers through foods, cosmetics, household products and some medicines. Vanilla flavouring agents typically contain vanillin or its analogue ethyl vanillin. Our previous study revealed that the inhalation of eugenol, which contains a vanillyl group, has an appetite-enhancing effect, and the inhalation of aroma compounds containing the vanillyl group or its analogues led to increased food intake in mice. Here, we found that vanillin, ethyl vanillin and eugenol showed appetite-enhancing effects, whereas isoeugenol and safrole did not. These results suggest that the appetite-enhancing effects could be attributable to the vanillyl group and could be affected by the position of the double bond in the aliphatic chain. Furthermore, the results of intraperitoneal administration of eugenol and vanillin suggest that their appetite-enhancing effects could occur via stimulation of olfactory receptors.
Specialized (iso)eugenol-4-O-methyltransferases (s-IEMTs) and methods of making and using the same

DOEpatents

Liu, Chang-Jun; Cai, Yuanheng

2017-01-31

Specialized (iso)eugenol 4-O-methyltransferase (s-IEMT) enzymes having increased capacity for methylation of monolignols are disclosed. The s-IEMTs have unique activity favoring methylation of coniferyl alcohol versus sinapyl alcohol. Various s-IEMTs methylate ferulic acid. Means for producing the various s-IEMTs are provided. The s-IEMTs are useful for modification of lignin content and production of aromatic compounds.
Evaluation of in vitro anticancer activity of Ocimum basilicum, Alhagi maurorum, Calendula officinalis and their parasite Cuscuta campestris.

PubMed

Behbahani, Mandana

2014-01-01

The present investigation was carried out to study the relationship between presence of cytotoxic compounds in Ocimum basilicum, Alhagi maurorum, Calendula officinalis and their parasite Cuscuta campestris. The cytotoxic activity of the pure compounds was performed by MTT assay against breast cancer cell lines (MCF-7 and MDA-MB-231) and normal breast cell line (MCF 10A). The induction of apoptosis was measured by the expression levels of p53, bcl-2, bax and caspase-3 genes using quantitative Real Time PCR. Three active fractions were detected by nuclear magnetic resonance as lutein, lupeol and eugenol, respectively, in C. officinalis, A. maurorum and O. basilicum. These compounds and their epoxidized forms were also detected in their parasite C. campestris. The cytotoxic activity of lutein epoxide, lupeol epoxide and eugenol epoxide was significantly more than lutein, lupeol and eugenol. The mRNA expression level of p53, caspase-3 and bax genes were increased in both cancer cells treated with all pure compounds. However, bcl-2 gene expression decreased in treated breast cancer cells. In conclusion, all the data indicated that the epoxide forms of lupeol, lutein and eugenol are potential drug candidates for inducing apoptosis in human breast cancer cells.
Evaluation of In Vitro Anticancer Activity of Ocimum Basilicum, Alhagi Maurorum, Calendula Officinalis and Their Parasite Cuscuta Campestris

PubMed Central

Behbahani, Mandana

2014-01-01

The present investigation was carried out to study the relationship between presence of cytotoxic compounds in Ocimum basilicum, Alhagi maurorum, Calendula officinalis and their parasite Cuscuta campestris. The cytotoxic activity of the pure compounds was performed by MTT assay against breast cancer cell lines (MCF-7 and MDA-MB-231) and normal breast cell line (MCF 10A). The induction of apoptosis was measured by the expression levels of p53, bcl-2, bax and caspase-3 genes using quantitative Real Time PCR. Three active fractions were detected by nuclear magnetic resonance as lutein, lupeol and eugenol, respectively, in C. officinalis, A. maurorum and O. basilicum. These compounds and their epoxidized forms were also detected in their parasite C. campestris. The cytotoxic activity of lutein epoxide, lupeol epoxide and eugenol epoxide was significantly more than lutein, lupeol and eugenol. The mRNA expression level of p53, caspase-3 and bax genes were increased in both cancer cells treated with all pure compounds. However, bcl-2 gene expression decreased in treated breast cancer cells. In conclusion, all the data indicated that the epoxide forms of lupeol, lutein and eugenol are potential drug candidates for inducing apoptosis in human breast cancer cells. PMID:25548920
Anethol, cinnamaldehyde, and eugenol inclusion in feed affects postweaning performance and feeding behavior of piglets.

PubMed

Blavi, L; Solà-Oriol, D; Mallo, J J; Pérez, J F

2016-12-01

The early exposure of the fetus to certain volatiles may result in a further preference for these compounds later in life and could positively affect the acceptance of feed containing a similar flavor and the zootechnical responses. The study consisted of 2 trials to determine if including Fluidarom 1003 (a commercially flavored feed additive containing >25% anethol and cinnamaldehyde and >10% eugenol; Norel S.A., Madrid, Spain, Spain) in sow and postweaning piglet diets 1) provokes the presence or absence of 3 major volatile compounds (anethol, cinnamaldehyde, and eugenol) in amniotic fluid and milk, affecting piglet performance (BW, ADG, ADFI, and feed conversion ratio) after weaning, and 2) modifies creep feed consumption and feed preference in a 2-choice test. The major compounds, anethol, cinnamaldehyde, and eugenol, were detected in amniotic fluid; however, only traces were observed in milk. The inclusion of flavor in the sow diets improved piglet consumption and growth after weaning ( = 0.001). Furthermore, the positive reward associated with the flavor included in the sow diet was stronger when piglets were offered a nonflavored creep feed ( < 0.05). Therefore, early exposure of pigs' fetuses to maternal dietary clues at the end of gestation might allow for conditioning pigs after weaning.
Identification of Insecticidal Constituents from the Essential Oil from the Aerial Parts Stachys riederi var. japonica.

PubMed

Quan, Meirong; Liu, Qi Zhi; Liu, Zhi Long

2018-05-17

The essential oil of Stachys riederi var. japonica (Family: Lamiaceae) was extracted by hydrodistillation and determined by GC and GC-MS. A total of 40 components were identified, representing 96.01% of the total oil composition. The major compounds in the essential oil were acetanisole (15.43%), anisole (9.43%), 1,8-cineole (8.07%), geraniol (7.89%), eugenol (4.54%), caryophyllene oxide (4.47%), caryophyllene (4.21%) and linalool (4.07%). Five active constituents (acetanisole, anisole, 1,8-cineole, eugenol and geraniol) were identified by bioactivity-directed fractionation. The essential oil possessed fumigant toxicity against maize weevils ( Sitophilus zeamais ) and booklice ( Liposcelis bostrychophila ), with LC 50 values of 15.0 mg/L and 0.7 mg/L, respectively. Eugenol and anisole exhibited stronger fumigant toxicity than the oil against booklice. 1,8-Cineole showed stronger toxicity, and anisole as well as eugenol exhibited the same level of fumigant toxicity as the essential oil against maize weevils. The essential oil also exhibited contact toxicity against S. zeamais adults and L. bostrychophila , with LC 50 values of 21.8 µg/adult and 287.0 µg/cm², respectively. The results indicated that the essential oil of S. riederi var. japonica and its isolates show potential as fumigants, and for their contact toxicity against grain storage insects.
Development of antimicrobial nanoemulsion-based delivery systems against selected pathogenic bacteria using a thymol-rich Thymus daenensis essential oil.

PubMed

Ghaderi, L; Moghimi, R; Aliahmadi, A; McClements, D J; Rafati, H

2017-10-01

Thymol-rich medicinal plants have been used in traditional medicine to relieve infectious diseases. However, the application of essential oils as medicine is limited by its low water solubility and high vapour pressure. The objective of this study was to produce stable nanoemulsions of Thymus daenensis oil in water by preventing Ostwald ripening and phase separation. The antibacterial activity of bulk and emulsified essential oil against selected pathogenic bacteria including Gram-negative (Haemophilus influenzae, Pseudomonas aeruginosa) and Gram-positive (Streptococcus pneumoniae) were investigated in the liquid and vapour phase. The optimum formulation (L2) contained 2% Tween 80 (surfactant) and 0·1% lecithin (cosurfactant) had a mean droplet diameter of 131 nm. In the liquid phase, the optimized nanoemulsion exhibited good antibacterial activity against S. pneumonia with MIC value of 0·0039 mg mL -1 . In the vapour phase, the MIC values against S. pneumonia were similar (<7·35 μL L -1 ) for both bulk and emulsified essential oil. However, there was no antibacterial activity in the vapour phase against H. influenzae and P. aeruginosa. Analysis of thymol concentration in the head space indicated that the nanoemulsion retarded the release of thymol into the vapour phase. These findings highlight the potential applications of nanoemulsions containing essential oils as antibacterial products. The results of the current study highlight the advantages of nanoemulsification for improvement of the physicochemical properties and the antibacterial activity of T. daenensis EOs in the liquid and vapour phase for therapeutic purposes. © 2017 The Society for Applied Microbiology.
Effects of UV Rays and Thymol/Thymus vulgaris L. Extract in an ex vivo Human Skin Model: Morphological and Genotoxicological Assessment.

PubMed

Cornaghi, Laura; Arnaboldi, Francesca; Calò, Rossella; Landoni, Federica; Baruffaldi Preis, William Franz; Marabini, Laura; Donetti, Elena

2016-01-01

Ultraviolet (UV) radiation is the major environmental factor affecting functions of the skin. Compounds rich in polyphenols, such as Thymus vulgaris leaf extract and thymol, have been proposed for the prevention of UV-induced skin damage. We compared the acute effects induced by UVA and UVB rays on epidermal morphology and proliferation, cytotoxicity, and genotoxicity. Normal human skin explants were obtained from young healthy women (n = 7) after informed consent and cultured at the air-liquid interface overnight. After 24 h, the samples were divided in 2 groups: the former exposed to UVA (16 or 24 J/cm2) and the latter irradiated with UVB (0.24 or 0.72 J/cm2). One hour after the end of irradiation, supernatants were collected for evaluation of the lactate dehydrogenase activity. Twenty-four hours after UVB exposure, biopsies were processed for light and transmission electron microscopy analysis, proliferation, cytotoxicity, and genotoxicity. UVB and UVA rays induced early inhibition of cell proliferation and DNA damage compared to controls. In particular, UVB rays were always more cytotoxic and genotoxic than UVA ones. For this reason, we evaluated the effect of either T. vulgaris L. extract (1.82 µg/ml) or thymol (1 µg/ml) on all samples treated for 1 h before UVB irradiation. While Thymus had a protective action for all of the endpoints evaluated, the action of the extract was less pronounced on epidermal proliferation and morphological features. The results presented in this study could be the basis for investigating the mechanism of thymol and T. vulgaris L. extract against the damage induced by UV radiation. © 2016 S. Karger AG, Basel.
Polycyanurates and Polycarbonates Based on Eugenol: Alternatives to Thermosetting and Thermoplastic Polymers Based on Bisphenol A

DTIC Science & Technology

2014-08-14

to 5a. CONTRACT NUMBER In-House Thermosetting and Thermoplastic Polymers based on Bisphenol A 5b. GRANT NUMBER 5c. PROGRAM ELEMENT NUMBER 6...Francisco, CA, 14 August 2014. PA#14389 14. ABSTRACT Polycyanurate thermosetting networks, polycarbonate thermoplastics, and homogenous polycarbonate...ON EUGENOL: ALTERNATIVES TO THERMOSETTING AND THERMOPLASTIC POLYMES BASED ON BISPHENOL A 14 August 2014 Andrew J. Guenthner1, Benjamin G. Harvey2
Efficacy of Essential Oils of Thymus vulgaris and Origanum vulgare on Echinococcus granulosus

PubMed Central

Pensel, P. E.; Maggiore, M. A.; Gende, L. B.; Eguaras, M. J.; Denegri, M. G.; Elissondo, M. C.

2014-01-01

The aim of the present work was to determine the in vitro effect of T. vulgaris and O. vulgare essential oils against E. granulosus protoscoleces and cysts. Essential oils were added to the medium resulting in thymol final concentrations of 10 μg/mL. The essential oils had a time-dependent effect provoking the complete loss of protoscolex viability after 72 days of postincubation. The results were confirmed at the ultrastructure level. Loss of infectivity in protoscoleces incubated with O. vulgare after 60 days was observed. On the other hand, the weight of cysts recorded in mice inoculated with T. vulgaris treated protoscoleces was significantly lower than that obtained in control group. Gamma-glutamyl-transpeptidase activity was readily detected in the culture supernatant of protoscoleces treated either with the essential oils or thymol. T. vulgaris and O. vulgare essential oils and thymol can induce cell apoptosis of protoscoleces after short incubation times. The efficacy of T. vulgaris and O. vulgare essential oils was also demonstrated in vitro on E. granulosus murine cysts. Our data suggest that essential oils of T. vulgaris and O. vulgare have anthelmintic effect against protoscoleces and cysts of E. granulosus. PMID:25180033

Phenolic constituents from the roots of Mikania micrantha and their allelopathic effects.

PubMed

Xu, Qiaolin; Xie, Haihui; Xiao, Huilin; Wei, Xiaoyi

2013-07-31

Four new thymol derivatives, 8,10-dihydroxy-9-benzoyloxythymol (1), 9-isobutyryloxy-10-hydroxythymol (2), 7,8,9,10-tetrahydroxythymol (3), and 7,8,10-trihydroxy-9-E-feruloyloxythymol (4), were isolated from the fresh roots of Mikania micrantha , along with 8,9,10-trihydroxythymol (5), 8,10-dihydroxy-9-acetoxythymol (6), 8,10-dihydroxy-9-isobutyryloxythymol (7), 8,10-dihydroxy-9-(2-methylbutyryloxy)thymol (8), 8,9-dehydro-10-hydroxythymol (9), 8-methoxy-9-hydroxythymol (10), ethyl caffeate (11), ethyl ferulate (12), 3,5-di-O-caffeoylquinic acid (13), and mikanin (14). Their structures were determined by spectroscopic methods. The known thymol derivatives (5-10) were obtained from the genus Mikania for the first time. Allelopathic effects of these compounds on Arabidopsis thaliana seeds were evaluated by a filter paper assay. After the treatment at 0.1 mM for 4 days, the seed germination rate with compound 8 was 48% and the inhibitory rates of shoot growth with compounds 1, 2, 7-10, and 12 were over 40%. The IC50 values of compounds 1 and 8 on shoot growth were 342.5 and 625 μM, respectively.
O-methylation of natural phenolic compounds based on green chemistry using dimethyl carbonate

NASA Astrophysics Data System (ADS)

Prakoso, N. I.; Pangestu, P. H.; Wahyuningsih, T. D.

2016-02-01

The alkyl aryl ether compounds, of which methyl eugenol and veratraldehyde are the simplest intermediates can be synthesized by reacting eugenol and vanillin with the green reagent dimethyl carbonate (DMC). The reaction was carried out under mild of temperature and pressure. Excellent yields and selective products were obtained (95-96%) after a few hours. In the end of the reaction, the catalysts (base and Phase Transfer Catalyst) can be recovered and regenerated.
Synthesis and leishmanicidal activity of eugenol derivatives bearing 1,2,3-triazole functionalities.

PubMed

Teixeira, Róbson Ricardo; Gazolla, Poliana Aparecida Rodrigues; da Silva, Adalberto Manoel; Borsodi, Maria Paula Gonçalves; Bergmann, Bartira Rossi; Ferreira, Rafaela Salgado; Vaz, Boniek Gontijo; Vasconcelos, Géssica Adriana; Lima, Wallace Pacienza

2018-02-25

In this paper, it is described the synthesis and the evaluation of the leishmanicidal activity of twenty-six eugenol derivatives bearing 1,2,3-triazole functionalities. The evaluation of the compounds on promastigotes of Leishmania amazonensis (WHOM/BR/75/Josefa) showed that eugenol derivatives present leishmanicidal activities with varying degrees of effectiveness. The most active compound, namely 4-(3-(4-allyl-2-methoxyphenoxy)propyl)-1-(4-methylbenzyl)-1H-1,2,3-triazole (7k) (IC 50  = 7.4 ± 0.8 μmol L -1 ), also targeted Leishmania parasites inside peritoneal macrophages (IC 50  = 1.6 μmol L -1 ) without interfering with cell viability. The cytotoxicity of 7k against macrophage cells presented IC 50 of 211.9 μmol L -1 and the selective index was equal to 132.5. Under similar conditions, compound 7k was more effective than glucantime and pentamidine, two drugs currently in the clinic. In addition, theoretical calculations showed that this compound also presents most physicochemical and pharmacokinetic properties within the ranges expected for orally available drugs. It is believed that eugenol bearing 1,2,3-triazole functionalities may represent a scaffold to be explored toward the development of new agents to treat leishmaniasis. Copyright © 2018 Elsevier Masson SAS. All rights reserved.
Efficacy of Benzocaine, Eugenol and Menthol as Anesthetics for Freshwater Angelfish (Pterophyllum scalare).

PubMed

de Souza Romaneli, Rafael; Boaratti, André Zuffo; Tellechea Rodrigues, Andressa; de Almeida Ueiroz, Daniel Monge; Khan, Kifayat Ullah; Nascimento, Thiago Matias Torres; Fernandes, João Batista Kochenborger

2018-05-29

For the production and commercialization of ornamental fish species, it is indispensable to collect biometric data for the selection of animals for trade and genetic improvement of the stock. However, during handling processes, fishes receive more stress if proper anesthetics are not used. Thus, using appropriate anesthetics is an important tool for minimizing stress in animals. The objective of this study was to determine the effective concentrations of benzocaine, eugenol and menthol for angelfish (Pterophyllum scalare) anesthesia and to develop induction and recovery response curves for different concentrations of these anesthetics. A total of 75 fish were exposed to five concentrations of three different anesthetics, benzocaine (60, 85, 110, 135 and 160 mg L -1 ), eugenol (40, 80, 120, 160 and 200 mg L -1 ) and menthol (50, 75, 150, 200 and 250 mg L -1 ) in a completely randomized design. Each concentration (5 fish per concentration) consisted of five replicates and each replicate was represented by a single fish (1 fish per replicate). The results indicate that the tested substances have met the criteria of anesthetic efficiency. The effective concentrations of benzocaine, eugenol and menthol determined to be 89.25 mg L -1 , 90.6 mg L -1 and 92.1 mg L -1 , respectively for the anesthesia of freshwater angelfish. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.
Poly (DL-lactide-co-glycolide) (PLGA) nanoparticles with entrapped trans-cinnamaldehyde and eugenol for antimicrobial delivery applications.

PubMed

Gomes, Carmen; Moreira, Rosana G; Castell-Perez, Elena

2011-03-01

Eugenol and trans-cinnamaldehyde are natural compounds known to be highly effective antimicrobials; however, both are hydrophobic molecules, a limitation to their use within the food industry. The goal of this study was to synthesize spherical poly (DL-lactide-co-glycolide) (PLGA) nanoparticles with entrapped eugenol and trans-cinnamaldehyde for future antimicrobial delivery applications. The emulsion evaporation method was used to form the nanoparticles in the presence of poly (vinyl alcohol) (PVA) as a surfactant. The inclusion of antimicrobial compounds into the PLGA nanoparticles was accomplished in the organic phase. Synthesis was followed by ultrafiltration (performed to eliminate the excess of PVA and antimicrobial compound) and freeze-drying. The nanoparticles were characterized by their shape, size, entrapment efficiency, and antimicrobial efficiency. The entrapment efficiency for eugenol and trans-cinnamaldehyde was approximately 98% and 92%, respectively. Controlled release experiments conducted in vitro at 37 °C and 100 rpm for 72 h showed an initial burst followed by a slower rate of release of the antimicrobial entrapped inside the PLGA matrix. All loaded nanoparticles formulations proved to be efficient in inhibiting growth of Salmonella spp. (Gram-negative bacterium) and Listeria spp. (Gram-positive bacterium) with concentrations ranging from 20 to 10 mg/mL. Results suggest that the application of these antimicrobial nanoparticles in food systems may be effective at inhibiting specific pathogens. Nanoencapsulation of lipophilic antimicrobial compounds has great potential for improving the effectiveness and efficiency of delivery in food systems. This study consisted of synthesizing PLGA nanoparticles with entrapped eugenol and trans-cinnamaldehyde. By characterizing these new delivery systems, one can understand the controlled-release mechanism and antimicrobial efficiency that provides a foundation that will enable food manufacturers to design smart food systems for future delivery applications, including packaging and processing, capable of ensuring food safety to consumers.
Sublethal injury and virulence changes in Listeria monocytogenes and Listeria innocua treated with antimicrobials carvacrol and citral.

PubMed

Silva, A; Genovés, S; Martorell, P; Zanini, S F; Rodrigo, D; Martinez, A

2015-09-01

The aim of this study was to evaluate the effect of two antimicrobial substances, carvacrol and citral, on Listeria monocytogenes and Listeria innocua cells, as well as possible virulence changes in injured cells, using Caenorhabditis elegans as a model test. The results indicated that the percentage of sublethal damage was higher in L. monocytogenes than in L. innocua. The results of the study carried out by using C. elegans indicated that C. elegans fed in a lawn of L. monocytogenes previously treated with carvacrol showed a loss in life span (p ≤ 0.05) as compared with L. monocytogenes treated with citral, Escherichia coli OP50 as a negative control, and treated and untreated L. innocua. Egg laying was also affected: worms fed in a lawn of treated and untreated L. monocytogenes laid fewer eggs than those fed in a lawn of treated and untreated L. innocua or fed with OP50 as a negative control. Worms fed in a lawn of treated and untreated L. innocua also laid fewer eggs than those fed with OP50 as a negative control. A phenotype named bag of worms and an undescribed new one, "vulva inflammation", were also observed. Copyright © 2015 Elsevier Ltd. All rights reserved.
Cellulose nanocrystals from Actinidia deliciosa pruning residues combined with carvacrol in PVA_CH films with antioxidant/antimicrobial properties for packaging applications.

PubMed

Luzi, Francesca; Fortunati, Elena; Giovanale, Geremia; Mazzaglia, Angelo; Torre, Luigi; Balestra, Giorgio Mariano

2017-11-01

Kiwi Actinidia deliciosa pruning residues were here used for the first time as precursors for the extraction of high performing cellulose nanocrystals (CNC) by applying a bleaching treatment followed by an acidic hydrolysis. The resultant cellulosic nanostructures, obtained by an optimize extraction procedure (0.7% wt/v two times of sodium chlorite NaClO 2 ) followed by an hydrolysis step, were then used as reinforcements phases in poly(vinyl alcohol) (PVA) blended with natural chitosan (CH) based films and also combined, for the first time, with carvacrol used here as active agent. Morphological and optical characteristics, mechanical response, thermal and migration properties, moisture content and antioxidant and antimicrobial assays were conducted. The morphological, optical and colorimetric results underlined that no particular alterations were induced on the transparency and color of PVA and PVA_CH blend by the presence of CNC and carvacrol, while they were able to modulate the mechanical responses, to induce antioxidant activities maintaining the migration levels below the permitted limits and suggesting the possible application in industrial sectors. Finally, inhibitions on bacterial development were detected for multifunctional systems, suggesting their protective function against microorganisms contamination. Copyright © 2017 Elsevier B.V. All rights reserved.
Edible apple film wraps containing plant antimicrobials inactivate foodborne pathogens on meat and poultry products.

PubMed

Ravishankar, Sadhana; Zhu, Libin; Olsen, Carl W; McHugh, Tara H; Friedman, Mendel

2009-10-01

Apple-based edible films containing plant antimicrobials were evaluated for their activity against pathogenic bacteria on meat and poultry products. Salmonella enterica or E. coli O157:H7 (10(7) CFU/g) cultures were surface inoculated on chicken breasts and Listeria monocytogenes (10(6) CFU/g) on ham. The inoculated products were then wrapped with edible films containing 3 concentrations (0.5%, 1.5%, and 3%) of cinnamaldehyde or carvacrol. Following incubation at either 23 or 4 degrees C for 72 h, samples were stomached in buffered peptone water, diluted, and plated for enumeration of survivors. The antimicrobial films exhibited concentration-dependent activities against the pathogens tested. At 23 degrees C on chicken breasts, films with 3% antimicrobials showed the highest reductions (4.3 to 6.8 log CFU/g) of both S. enterica and E. coli O157:H7. Films with 1.5% and 0.5% antimicrobials showed 2.4 to 4.3 and 1.6 to 2.8 log reductions, respectively. At 4 degrees C, carvacrol exhibited greater activity than did cinnamaldehyde. Films with 3%, 1.5%, and 0.5% carvacrol reduced the bacterial populations by about 3, 1.6 to 3, and 0.8 to 1 logs, respectively. Films with 3% and 1.5% cinnamaldehyde induced 1.2 to 2.8 and 1.2 to 1.3 log reductions, respectively. For L. monocytogenes on ham, carvacrol films induced greater reductions than did cinnamaldehyde films at all concentrations tested. In general, the reduction of L. monocytogenes on ham at 23 degrees C was greater than at 4 degrees C. Added antimicrobials had minor effects on physical properties of the films. The results suggest that the food industry and consumers could use these films as wrappings to control surface contamination by foodborne pathogenic microorganisms.
Comparative evaluation of zinc oxide eugenol versus gelatin sponge soaked in plasma rich in growth factor in the treatment of dry socket: An initial study

PubMed Central

Pal, U. S.; Singh, Balendra Pratap; Verma, Vikas

2013-01-01

Purpose: The aim of this study was to report a comparison between the zinc oxide eugenol dressing and plasma rich in growth factor (PRGF) with gelatin sponge in the treatment of dry socket. Materials and Methods: This study comprised of 45 patients of dry socket in the span of one year. The patients were randomly divided into three groups on the basis of treatments: Group A (PRGF with gelatin sponge), group B (zinc oxide eugenol group), and group C (irrigation with sterile saline only). The clinical progress was noted at 1st, 2nd, 3rd, 7th, and 15th day after the treatment. Results: Patient's healing was better in group A than in group B but symptomatic pain relief was faster in group B. Group C fared worst in both aspects. Conclusion: We conclude that PRGF with gelatin sponge might be a treatment of choice in the management of dry socket. PMID:23853450
Ternary liquid-liquid equilibrium for eugenol + tert-butanol + water system at 303.15 and 323.15K and atmospheric pressure

NASA Astrophysics Data System (ADS)

Sucipto, Retno Kumala Hesti; Kuswandi, Wibawa, Gede

2017-05-01

The objective of this study was to determine ternary liquid-liquid equilibrium for eugenol + tert-butanol + water system at 303.15 and 323.15K and atmospheric pressure. Using 25 mL equilibrium cell equipped jacketted water connected to water bath to maintain equilibrium temperature constant. The procedure of this experiment was conducted by inserting mixture of eugenol + tert-butanol + water system at certain composition into equilibrium cell. The solution was stirred for 4 hours and then was allowed for 20 hours in order to separate aqueous and organic phases completely. The temperature equilibrium cell of and the atmosphere pressure were recorded as equilibrium temperature and pressure for each measurenment. The equilibrium compositions of each phase were analyzed using Gas Chromatography. The experimental data obtained in this work were correlated with NRTL and UNIQUAC models with root mean square deviation between esperimental and calculated equilibrium compositions of 0.03% and 0.04% respectively.
Free Radical Metabolism of Methyleugenol and Related Compounds

PubMed Central

2015-01-01

Methyleugenol, the methyl ether of eugenol, both of which are flavorant constituents of spices, has been listed by the National Toxicology Program’s Report on Carcinogens as reasonably anticipated to be a human carcinogen. This finding is based on the observation of increased incidence of malignant tumors at multiple tissue sites in experimental animals of different species. By contrast, eugenol is not listed. In this study, we show that both methyleugenol and eugenol readily undergo peroxidative metabolism in vitro to form free radicals with large hyperfine interactions of the methylene allylic hydrogen atoms. These large hyperfine splittings indicate large electron densities adjacent to those hydrogen atoms. Methyleugenol undergoes autoxidation such that the commercial product contains 10–30 mg/L hydroperoxide and is capable of activating peroxidases without the presence of added hydrogen peroxide. Additionally, the hydroperoxide is not a good substrate for catalase, which demonstrates that these antioxidant defenses will not be effective in protecting against methyleugenol exposure. PMID:24564854
Clove (Syzygium aromaticum): a precious spice

PubMed Central

Cortés-Rojas, Diego Francisco; de Souza, Claudia Regina Fernandes; Oliveira, Wanderley Pereira

2014-01-01

Clove (Syzygium aromaticum) is one of the most valuable spices that has been used for centuries as food preservative and for many medicinal purposes. Clove is native of Indonesia but nowadays is cultured in several parts of the world including Brazil in the state of Bahia. This plant represents one of the richest source of phenolic compounds such as eugenol, eugenol acetate and gallic acid and posses great potential for pharmaceutical, cosmetic, food and agricultural applications. This review includes the main studies reporting the biological activities of clove and eugenol. The antioxidant and antimicrobial activity of clove is higher than many fruits, vegetables and other spices and should deserve special attention. A new application of clove as larvicidal agent is an interesting strategy to combat dengue which is a serious health problem in Brazil and other tropical countries. Pharmacokinetics and toxicological studies were also mentioned. The different studies reviewed in this work confirm the traditional use of clove as food preservative and medicinal plant standing out the importance of this plant for different applications. PMID:25182278
The mutagenicities of safrole, estragole, eugenol, trans-anethole, and some of their known or possible metabolites for Salmonella typhimurium mutants.

PubMed

Swanson, A B; Chambliss, D D; Blomquist, J C; Miller, E C; Miller, J A

1979-04-01

Safrole, estragole, anethole, and eugenol and some of their known or possible metabolites were tested for mutagenic activity for S. typhimurium TA1535, TA100, and TA98. Highly purified 1'-hydroxyestragole and 1'-hydroxysafrole were mutagenic (approximately 15 and 10 revertants/micromole, respectively) for strain TA100 in the absence of fortified liver microsomes; trans-anethole and estragole appeared to have very weak activity. 3'-Hydroxyanethole was too toxic for an adequate test. Supplementation with NADPH-fortified rat-liver microsomes and cytosol converted 3'-hydroxyanethole to a mutagen(s) and increased the mutagenic activities for strain TA100 of 1'-hydroxyestragole, 1'-hydroxysafrole, estragole, and anethole. No mutagenicity was detected for safrole or eugenol with or without added NADPH-fortified liver preparations. The electrophilic 2',3'-oxides of safrole, 1'-hydroxysafrole, 1'-acetoxysafrole, 1'-oxosafrole, estragole, 1'-hydroxyestragole, and eugenol showed dose-dependent mutagenic activities for strain TA1535 in the absence of fortified liver microsomes. These mutagenic activities ranged from about 330 revertants/micromole for 1'-oxosafrole-2',3'-oxide to about 7000 revertants/micromole for safrole-2',3'-oxide. The arylalkenes, their hydroxylated derivatives, or their epoxides did not show mutagenic activity for strain TA98, except for 1'-oxosafrole-2',3'-oxide, which had weak activity. Since the arylalkenes are hydroxylated and/or epoxidized by hepatic microsomes, hydroxy and epoxide derivatives appear to be proximate and ultimate mutagenic metabolites, respectively, of the arylalkenes.
CCoAOMT Down-Regulation Activates Anthocyanin Biosynthesis in Petunia1

PubMed Central

Shaipulah, Nur Fariza M.; Muhlemann, Joëlle K.; Woodworth, Benjamin D.; Van Moerkercke, Alex; Ramirez, Aldana A.; Haring, Michel A.; Schuurink, Robert C.

2016-01-01

Anthocyanins and volatile phenylpropenes (isoeugenol and eugenol) in petunia (Petunia hybrida) flowers have the precursor 4-coumaryl coenzyme A (CoA) in common. These phenolics are produced at different stages during flower development. Anthocyanins are synthesized during early stages of flower development and sequestered in vacuoles during the lifespan of the flowers. The production of isoeugenol and eugenol starts when flowers open and peaks after anthesis. To elucidate additional biochemical steps toward (iso)eugenol production, we cloned and characterized a caffeoyl-coenzyme A O-methyltransferase (PhCCoAOMT1) from the petals of the fragrant petunia ‘Mitchell’. Recombinant PhCCoAOMT1 indeed catalyzed the methylation of caffeoyl-CoA to produce feruloyl CoA. Silencing of PhCCoAOMT1 resulted in a reduction of eugenol production but not of isoeugenol. Unexpectedly, the transgenic plants had purple-colored leaves and pink flowers, despite the fact that cv Mitchell lacks the functional R2R3-MYB master regulator ANTHOCYANIN2 and has normally white flowers. Our results indicate that down-regulation of PhCCoAOMT1 activated the anthocyanin pathway through the R2R3-MYBs PURPLE HAZE (PHZ) and DEEP PURPLE, with predominantly petunidin accumulating. Feeding cv Mitchell flowers with caffeic acid induced PHZ expression, suggesting that the metabolic perturbation of the phenylpropanoid pathway underlies the activation of the anthocyanin pathway. Our results demonstrate a role for PhCCoAOMT1 in phenylpropene production and reveal a link between PhCCoAOMT1 and anthocyanin production. PMID:26620524
Cytotoxicity Testing of Temporary Luting Cements with Two- and Three-Dimensional Cultures of Bovine Dental Pulp-Derived Cells

PubMed Central

Ülker, Hayriye Esra; Ülker, Mustafa; Gümüş, Hasan Önder; Yalçın, Muhammet; Şengün, Abdulkadir

2013-01-01

This study evaluated the cytotoxicity of eugenol-containing and eugenol-free temporary luting cements. For cytotoxicity testing, bovine pulp-derived cells transfected with Simian virus 40 Large T antigen were exposed to extracts of eugenol-containing (Rely X Temp E) and eugenol-free (Provicol, PreVISION CEM, and Rely X Temp NE) temporary luting cements for 24 h. The cytotoxicity of the same materials was also evaluated in a dentin barrier test device using three-dimensional cell cultures of bovine pulp-derived cells. The results of the cytotoxicity studies with two-dimensional cultures of bovine dental pulp-derived cells revealed that cell survival with the extracts of Rely X Temp E, Provicol, PreVISION CEM, and Rely X Temp NE was 89.1%, 84.9%, 92.3%, and 66.8%, respectively. Rely X Temp NE and Provicol showed cytotoxic effects on bovine dental pulp-derived cells (P < 0.05). The results of the dentin barrier test revealed that cell survival with the above-mentioned temporary cement was 101.5%, 91.9%, 93.5%, and 90.6%, respectively. None of the temporary luting cements significantly reduced cell survival compared with the negative control in the dentin barrier test (P > 0.05). Biologically active materials released from temporary luting cements may not influence the dentine-pulp complex if the residual dentine layer is at least 0.5 mm thick. PMID:23984419
A time course study of glucose levels and innate immune response in gilthead seabream (Sparus aurata L.) after exposure to clove oil-eugenol derived anaesthetic.

PubMed

Bahi, A; Guardiola, F A; Esteban, M A

2018-06-01

Clove oil is used as an anaesthetic for many species of fish worldwide; however, relatively few studies have assessed its effects on the innate immune response on these species. The present work aimed to investigate the effects of clove oil-eugenol derived anaesthetic on some humoral and cellular immune response in gilthead seabream (Sparus aurata L.). To compare with an unexposed control group, fish were exposed to 55 ppm clove oil for 5 min, before being sampled at 1, 24 and 48 h post-exposure. Serum glucose level was also measured to obtain information on the fish physiological response after clove oil anaesthesia. One hour after exposure the haemolytic complement activity of fish was lower than in the unexposed group. By contrast, the leucocyte peroxidase activity in head-kidney was significantly stimulated 24 h after exposure to clove oil-eugenol. The rest of innate immune parameters evaluated and the glucose levels not were affected by clove oil exposure at any sampling point. Overall, the use of clove oil at 55 ppm as anaesthetic did not seem to alter the innate immune response and neither did it trigger a stress response. The use of clove oil-eugenol derived had become common practice in aquaculture, and its use with gilthead seabream can be considered safe as it does not cause immunodepression in anesthetized fish. Copyright © 2018 Elsevier Ltd. All rights reserved.
Impact of essential oils on the taste acceptance of tomato juice, vegetable soup, or poultry burgers.

PubMed

Espina, Laura; García-Gonzalo, Diego; Pagán, Rafael

2014-08-01

Despite the vast body of available literature on the possibilities of essential oils (EOs) as food preservatives or functional ingredients, the sensory impact of their addition to foods has barely been approached. This work focuses on the hedonic taste acceptance of 3 food products (tomato juice, vegetable soup, and poultry burgers) when they are incorporated with potentially antimicrobial concentrations (20 to 200 μL/L) of 6 selected EOs (lemon, pennyroyal mint, thyme, and rosemary) and individual compounds (carvacrol, p-cymene). Although addition of 20 μL/L of pennyroyal mint or lemon EO did not change the taste acceptance of tomato juice, higher concentrations of these compounds or any concentration of the other 4 compounds did. In vegetable soup, the tolerance limit for rosemary EO, thyme EO, carvacrol, or p-cymene was 20 μL/L, while the addition of 200 μL/L of lemon EO was accepted. Tolerance limits in poultry burgers were established in 20 μL/L for carvacrol and thyme EOs, 100 μL/L for pennyroyal mint EO and p-cymene, and 200 μL/L for lemon and rosemary EOs. Moreover, incorporation of pennyroyal mint EO to tomato juice or poultry burgers, and enrichment of vegetable soup with lemon EO, could contribute to the development of food products with an improved sensory appeal. © 2014 Institute of Food Technologists®
In vitro antibacterial, antifungal, and antioxidant activities of the essential oil and methanol extracts of herbal parts and callus cultures of Satureja hortensis L.

PubMed

Güllüce, M; Sökmen, M; Daferera, D; Ağar, G; Ozkan, H; Kartal, N; Polissiou, M; Sökmen, A; Sahin, F

2003-07-02

The present study was designated to evaluate the antimicrobial and antioxidant activities of the essential oil, obtained by using a Clevenger distillation apparatus, water soluble (polar) and water insoluble (nonpolar) subfractions of the methanol extracts from aerial parts of Satureja hortensis L. plants, and methanol extract from calli established from the seeds using Gamborg's B5 basal media supplemented with indole-3-butyric acid (1.0 ppm), 6-benzylaminopurine (N(6)-benzyladenine) (1.0 ppm), and sucrose (2.5%). The antimicrobial test results showed that the essential oil of S. hortensis had great potential antimicrobial activities against all 23 bacteria and 15 fungi and yeast species tested. In contrast, the methanol extract from callus cultures and water soluble subfraction of the methanol extract did not show antimicrobial activities, but the nonpolar subfraction had antibacterial activity against only five out of 23 bacterial species, which were Bacillus subtilis, Enterococcus fecalis, Pseudomonas aeruginosa, Salmonella enteritidis, and Streptococcus pyogenes. Antioxidant studies suggested that the polar subfractions of the methanol extract of intact plant and methanol extract of callus cultures were able to reduce the stable free radical 2,2-diphenyl-1-picrylhydrazyl to the yellow-colored diphenylpicrylhydrazine. In this assay, the strongest effect was observed for the tissue culture extract, with an IC(50) value of 23.76 +/- 0.80 microgram/mL, which could be compared with the synthetic antioxidant agent butylated hydroxytoluene. On the other hand, linoleic acid oxidation was 95% inhibited in the presence of the essential oil while the inhibition was 90% with the chloroform subfraction of the intact plant. The chemical composition of a hydrodistilled essential oil of S. hortensis was analyzed by gas chromatography (GC)/flame ionization detection (FID) and a GC-mass spectrometry system. A total 22 constituents representing 99.9% of the essential oil were identified by GC-FID analaysis. Thymol (29.0%), carvacrol (26.5%), gamma-terpinene (22.6%), and p-cymene (9.3%) were the main components.
Eugenol oil nanoemulsion: antifungal activity against Fusarium oxysporum f. sp. vasinfectum and phytotoxicity on cottonseeds

NASA Astrophysics Data System (ADS)

Abd-Elsalam, Kamel A.; Khokhlov, Alexei R.

2015-02-01

The current research deals with the formulation and characterization of bio-based oil-in-water nanoemulsion. The formulated eugenol oil nanoemulsion was characterized by dynamic light scattering, stability test, transmission electron microscopy and thin layer chromatography. The nanoemulsion droplets were found to have a Z-average diameter of 80 nm and TEM study reveals the spherical shape of eugenol oil nanoemulsion (EON). The size of the nanoemulsion was found to be physically stable up to more than 1-month when it was kept at room temperature (25 °C). The TEM micrograph showed that the EON was spherical in shape and moderately mono or di-dispersed and was in the range of 50-110 nm. Three concentrations of the nanoformulation were used to evalute the anti-fusarium activity both in vitro and in vivo experiments. SDS-PAGE results of total protein from the Fusarium oxysporum f. sp. vasinfectum (FOV) isolate before and after treatment with eugenol oil nanoemulsion indicate that the content of extra cellular soluble small molecular proteins decreased significantly in EON-treated fungus. Light micrographs of mycelia and spores treated with EON showed the disruption of the fungal structures. The analysis of variance (ANOVA) for Fusarium wilt incidence indicated highly significant ( p = 0.000) effects of concentration, genotype, and their interaction. The difference in wilt incidence between concentrations and control was not the same for each genotype, that is, the genotypes responded differently to concentrations. Effects of three EON concentration on germination percentage, and radicle length, were determined in the laboratory. One very interesting finding in the current study is that cotton genotypes was the most important factors in determining wilt incidence as it accounted for 93.18 % of the explained (model) variation. In vitro experiments were conducted to evaluate the potential phytotoxic effect of three EON concentrations. Concentration, genotype and concentration x genotype interaction were all highly significant sources of variation in seed germination; however, interaction was the first in importance as a source of variation followed by the concentration, while genotype was the least important source of variation. These results suggest the potential use of eugenol oil nanoemulsion for protecting seedcotton from Fusarium wilt infection.
Eugenol-rich Fraction of Syzygium aromaticum (Clove) Reverses Biochemical and Histopathological Changes in Liver Cirrhosis and Inhibits Hepatic Cell Proliferation

PubMed Central

Ali, Shakir; Prasad, Ram; Mahmood, Amena; Routray, Indusmita; Shinkafi, Tijjani Salihu; Sahin, Kazim; Kucuk, Omer

2014-01-01

Background: Dried flower bud of Syzygium aromaticum (clove) is rich in eugenol, an antioxidant and antiinflammatory compound that can protect liver against injury. Clove, besides eugenol, also contains other pharmacologically active phytochemicals such as β-sitosterol and ascorbic acid. This study reports the effect of eugenol-rich fraction (ERF) of clove on liver cirrhosis induced by thioacetamide. Methods: Cirrhosis of the liver, which predisposes to hepatocellular carcinoma, was induced by administering thioacetamide (0.03%) in drinking water for 16 weeks. Cirrhotic animals were divided into two groups; the treated group was administered ERF for 9 weeks, one week after discontinuation of thioacetamide, while the other group received normal saline for a similar duration of time. Results: The treatment with ERF, as determined by histopathology and through a battery of biochemical markers of hepatic injury, oxidative stress and drug metabolizing enzymes, significantly ameliorated the signs of liver cirrhosis. It lowered the elevated levels of alkaline phosphatase, γ-glutamyl transferase and other biochemical changes in liver cirrhosis. Histopathology of the liver corroborated the effect of ERF with biochemical findings. ERF treatment further inhibited cell proliferation, as demonstrated by reduced [3H]-thymidine uptake. Conclusions: Data provide evidence supporting the protective action of ERF on liver cirrhosis. The study assumes significance because cirrhosis predisposes the liver to cancer, which is characterized by abnormal cell proliferation. ERF in this study is reported to inhibit hepatic cell proliferation and at the same time decrease oxidative stress, which might be the mechanism of protection against liver cirrhosis. PMID:25574464

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