Chemical composition and biological activities of leaf and fruit essential oils from Eucalyptus camaldulensis.

PubMed

Dogan, Gulden; Kara, Nazan; Bagci, Eyup; Gur, Seher

2017-10-26

The chemical composition of the essential oils from the leaves and fruit of Eucalyptus camaldulensis grown in Mersin, Turkey was analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) techniques. The biological activities (antibacterial and antifungal) were examined using the agar well diffusion method. The main leaf oil constituents were p-cymene (42.1%), eucalyptol (1,8-cineole) (14.1%), α-pinene (12.7%) and α-terpinol (10.7%). The main constituents of the fruit oil were eucalyptol (1,8-cineole) (34.5%), p-cymene (30.0%), α-terpinol (15.1%) and α-pinene (9.0%). Our results showed that both types of oils are rich in terms of monoterpene hydrocarbons and oxygenated monoterpenes. The leaf and fruit essential oils of E. camaldulensis significantly inhibited the growth of Gram-positive (Staphylococcus aureus and Bacillus subtilis) and Gram-negative (Escherichia coli and Streptococcus sp.) bacteria (p<0.05). The oils also showed fungicidal activity against Candida tropicalis and C. globrata. Leaf essential oils showed more activity than fruit essential oils, probably due to the higher p-cymene concentration in leaves.

Design, Synthesis and Characterisation of New Chimeric Ruthenium(II)-Gold(I) Complexes as Improved Cytotoxic Agents

PubMed Central

Massai, Lara; Fernández-Gallardo, Jacob; Guerri, Annalisa; Arcangeli, Annarosa; Pillozzi, Serena

2015-01-01

Two heterobimetallic complexes, i.e. [RuCl2(p-cymene)(µ-dppm)AuC] (1) and [RuCl2(p-cymene)(µ-dppm)Au S(thiazoline)] (3), based on known cytotoxic [Ru(p-cymene)Cl2(PR3)] and [AuX(PR3)] (X = Cl, SR) molecular scaffolds, with the diphosphane linker 1,1-bis(diphenylphosphino) methane, dppm, were conveniently prepared and characterised. Remarkably, the new compounds manifested a more favourable in vitro pharmacological profile toward cancer cells than individual ruthenium and gold species being either more cytotoxic or more selective. The interactions of the study compounds with (pBR322) DNA and their inhibitory effects on cathepsin B were also assessed. In addition, their reactivity toward suitable models of protein targets was explored and clear evidence gained for disruption of the bimetallic motif and for protein binding of monometallic fragments. Overall, the data reported here strongly support the concept of multifunctional heterometallic compounds as “improved” candidate agents for cancer treatment. The mechanistic and pharmacological implications of the present findings are discussed. PMID:25996553

Design, synthesis and characterisation of new chimeric ruthenium(II)-gold(I) complexes as improved cytotoxic agents.

PubMed

Massai, Lara; Fernández-Gallardo, Jacob; Guerri, Annalisa; Arcangeli, Annarosa; Pillozzi, Serena; Contel, María; Messori, Luigi

2015-06-28

Two heterobimetallic complexes, i.e. [RuCl2(p-cymene)(μ-dppm)AuC] (1) and [RuCl2(p-cymene)(μ-dppm)Au(S-thiazoline)] (3), based on known cytotoxic [Ru(p-cymene)Cl2(PR3)] and [AuX(PR3)] (X = Cl, SR) molecular scaffolds, with the diphosphane linker 1,1-bis(diphenylphosphino)methane, dppm, were conveniently prepared and characterised. Remarkably, the new compounds manifested a more favourable in vitro pharmacological profile toward cancer cells than individual ruthenium and gold species being either more cytotoxic or more selective. The interactions of the studied compounds with (pBR322) DNA and their inhibitory effects on cathepsin B were also assessed. In addition, their reactivity toward suitable models of protein targets was explored and clear evidence gained for disruption of the bimetallic motif and for protein binding of monometallic fragments. Overall, the data reported here strongly support the concept of multifunctional heterometallic compounds as "improved" candidate agents for cancer treatment. The mechanistic and pharmacological implications of the present findings are discussed.

Rate and pathways for the reaction of OH with the biogenic p-cymene, an alkylated aromatic

NASA Astrophysics Data System (ADS)

Strekowski, R.; Rayez, M.-T.; Rayez, J.-C.; Zetzsch, C.

2009-04-01

Aromatics are known to contribute strongly to tropospheric formation of ozone, and p-cymene (4-isopropyltoluene) is one of only a few biogenic, volatile aromatic hydrocarbons. In spite of its symmetry, this molecule (CH3 - °-CH(CH3)2) has a multitude of potential pathways of its reaction with OH radicals. Addition of OH is well-known to be the predominating primary step in the tropospheric transformation of aromatic hydrocarbons. The addition is expected to occur preferably at a non-occupied position, where four positions are available: two equivalent ones ortho to the methyl group and two equivalent ones ortho to the isopropyl group. Furthermore, various C-H bonds (4 aromatic and 10 aliphatic) are available for abstraction, leading to benzyl-type radicals in two cases. The present study combines theoretical calculations with kinetic experiments in the gas phase. The theoretical calculations are based on electronic quantum chemistry DFT method for the investigation of the possible pathways in the potential energy surface of the reaction. The experiments are carried out by the flash photolysis/resonance fluorescence technique. OH radicals are produced by pulsed vacuum-UV photolysis of H2O (> 115 nm) in the presence of p-cymene in a slow flow of He as carrier gas. Their pseudo-first-order decays are monitored by resonance fluorescence, storing the photon counts by multichannel scaling in a PC and accumulating 50 decays each; see Koch et al. (2007) for details of the technique and evaluation of data. The temperature was varied between room temperature (295 K) and 345K, the He pressure was 250 mbar, and the level of p-cymene was increased stepwise, up to 3 x 1013 molecules/cm3. The decays of OH were observed to be exponential at room temperature, becoming clearly biexponential at higher temperatures, thus indicating reversible addition of OH according to the equilibration OH + p-cymene ⇔ p-cymene-OH (1, -1) These reactions might be accompanied by various abstraction channels, summarized as OH + p-cymene ⇒ alkylbenzyl + H2O (2) A value of 1.4 x 10-11 cm3 s-1 at 295 K is obtained for the sum k1 + k2, in good agreement with a value of 1.51 x 10-11 cm3 s-1determined by Corchnoy and Atkinson (1990) in a smog chamber at 295 K. The sum k1 + k2 decreases slightly with increasing temperature, falling below 10-11 cm3 s-1 at 345 K. The Arrhenius plot reveals a curved behaviour with a negative activation energy, approximately 1 x 10-12 exp (60 K/T) cm3 s-1. The biexponential behaviour corresponds to an apparent equilibrium constant of k1/k-1 = 8 x 10-25 exp [(-8500 ± 400) K/T] cm3 s-1. On the other hand, the bond energy of OH in the adduct can hardly be obtained from this biexponential behaviour alone since the abstraction of H atoms from the alkyl groups of p-cymene can be estimated to contribute markedly. Extrapolating the respective abstraction channels of toluene and the xylenes to two methyl substituents would yield k2= 1.6 x 10-18 T2exp (-38 K/T) cm3 s-1 (Atkinson, 1989). This amounts to 1.2x10-12 cm3 s-1 at 295 K (about 9% of the observed reactivity) and 1.7x10-12 cm3 s-1 at 345K (>17% of the observed reactivity) and does not even take the possibly largerreactivity of the isopropyl group (as compared to CH3) into account. The abstraction channel has been found to predominate in the analogous reaction of atomic Cl with p-cymene (Finlayson-Pitts et al, 1999), and further experiments by other methods are required to clarify the reaction channels for OH radicals. References Atkinson, R. (1989) Kinetics and Mechanisms of the Gas-Phase Reactions of the Hydroxyl Radical with Organic Compounds. J. Phys. Chem. Ref. Data, Monograph 1, Am. Chem. Soc./Am. Inst. Phys./NIST, p. 229. Corchnoy, S.B., Atkinson, R. (1990) Kinetics of the gas-phase reactions of OH and NO3 radicals with 2-Carene, 1,8-CineoIe, p-Cymene, and Terpinolene. Environ. Sci. Technol. 24, 1497-1502. Finlayson-Pitts, B. J., Keoshian, C.J., Buehler, B., Ezell, A.A. (1999) Kinetics of reaction of chlorine atoms with some biogenic organics. Int . J. Chem. Kinet. 31, 491-499. Koch, R., Knispel, R. Elend, M., Siese, M., Zetzsch, C. (2007) Consecutive reactions of aromatic-OH adducts with NO, NO2 and O2: benzene, naphthalene, toluene, m- and p-xylene, hexamethylbenzene, phenol, m-cresol and aniline. Atmos. Chem. Phys. 7, 2057-2071.

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.

A green analytical chemistry approach for lipid extraction: computation methods in the selection of green solvents as alternative to hexane.

PubMed

Cascant, Mari Merce; Breil, Cassandra; Garrigues, Salvador; de la Guardia, Miguel; Fabiano-Tixier, Anne Silvie; Chemat, Farid

2017-05-01

There is a great interest in finding alternatives and green solvents in extraction processes to replace petroleum based solvents. In order to investigate these possibilities, computational methods, as Hansen solubility parameters (HSP) and conductor-like screening model for real solvent (COSMO-RS), were used in this work to predict the solvation power of a series of solvents in salmon fish lipids. Additionally, experimental studies were used to evaluate the performance in lipids extraction using 2-methyltetrahydrofurane, cyclopentyl methyl ether, dimethyl carbonate, isopropanol, ethanol, ethyl acetate, p-cymene and d-limonene compared with hexane. Lipid classes of extracts were obtained by using high performance thin-layer chromatography (HPTLC), whereas gas chromatography with a flame ionization detector (GC/FID) technique was employed to obtain fatty acid profiles. Some differences between theoretical and experimental results were observed, especially regarding the behavior of p-cymene and d-limonene, which separate from the predicted capability. Results obtained from HPTLC indicated that p-cymene and d-limonene extract triglycerides (TAGs) and diglycerides (DAGs) at levels of 73 and 19%, respectively, whereas the other studied extracts contain between 75 and 76% of TAGs and between 16 and 17% of DAGs. Fatty acid profiles, obtained by using GC-FID, indicated that saturated fatty acids (SFAs) between 19.5 and 19.9% of extracted oil, monounsaturated fatty acids (MUFAs) in the range between 43.5 and 44.9%, and PUFAs between 31.2 and 34.6% were extracted. p-Cymene and limonene extracts contained lower percentages than the other studied solvents of some PUFAs due probably to the fact that these unsaturated fatty acids are more susceptible to oxidative degradation than MUFAs. Ethyl acetate has been found to be the best alternative solvent to hexane for the extraction of salmon oil lipids. Graphical Abstract ᅟ.

Benefits of a silica-based fluoride toothpaste containing o-cymen-5-ol, zinc chloride and sodium fluoride.

PubMed

Newby, Craig S; Rowland, Joanna L; Lynch, Richard J M; Bradshaw, David J; Whitworth, Darren; Bosma, Mary Lynn

2011-08-01

Fluoride toothpastes in conjunction with tooth brushing are used to clean teeth, control plaque build-up and for anti-caries benefits. Toothpastes are designed with attractive flavours and appearances to encourage regular prolonged use to maximise these benefits. The incorporation of additional ingredients into toothpaste is a convenient way to provide supplementary protection that fits into people's everyday oral care routine. Such ingredients should not compromise the primary health benefits of toothpaste nor discourage its use. o-Cymen-5-ol and zinc chloride have been incorporated into a sodium fluoride (NaF)/silica toothpaste at 0.1%w/w and 0.6%w/w respectively to provide additional benefits. These include improved gingival health maintenance, in terms of the reduction of plaque, gingival index and bleeding, and an immediate and long lasting reduction in volatile sulfur compounds (VSCs) measured on breath. These benefits can be attributed to the antimicrobial and neutralisation actions of the toothpaste. The use of established fluoride models demonstrated no compromise in NaF bioavailability. The toothpaste was formulated without compromising product aesthetics. The combination of o-cymen-5-ol and zinc chloride in toothpaste gave superior maintenance of gingival health and reduction in malodour related VSCs without compromising the primary health benefits of the toothpaste or diminishing attributes preferred for the product's use. © 2011 FDI World Dental Federation.

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®

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

Study of the solubility and stability of polystyrene wastes in a dissolution recycling process

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

Garcia, Maria Teresa; Gracia, Ignacio; Duque, Gema

2009-06-15

Dissolution with suitable solvents is one of the cheapest and more efficient processes for polystyrene waste management. In this work the solubility of polystyrene foams in several solvents benzene, toluene, xylene, tetrahydrofuran, chloroform, 1,3-butanediol, 2-butanol, linalool, geraniol, d-limonene, p-cymene, terpinene, phellandrene, terpineol, menthol, eucalyptol, cinnamaldheyde, nitrobenzene, N,N-dimethylformamide and water has been determined. Experimental results have shown that to develop a 'green process' the constituents of essential oils, d-limonene, p-cymene, terpinene, phellandrene, are the most appropriate solvents. The action of these solvent does not produce any degradation of polymer chains. The solubility of the polymer in the mentioned solvents at differentmore » temperatures has been investigated. The solvent can be easily recycled by distillation.« less

Synthesis, structure, DNA binding and anticancer activity of mixed ligand ruthenium(II) complex

NASA Astrophysics Data System (ADS)

Gilewska, Agnieszka; Masternak, Joanna; Kazimierczuk, Katarzyna; Trynda, Justyna; Wietrzyk, Joanna; Barszcz, Barbara

2018-03-01

In order to obtain a potential chemotherapeutic which is not affected on the normal BALB/3T3 cell line, a new arene ruthenium(II) complex {[RuCl(L1)(η6-p-cymene)]PF6}2 · H2O has been synthesized by a direct reaction of precursor, [{(η6-p-cymene)Ru(μ-Cl)}2Cl2], with N,N-chelating ligand (L1 - 2,2‧-bis(4,5-dimethylimidazole). The compound has been fully characterized by elemental analysis, X-ray diffraction, IR, UV-Vis and 1H, 13C NMR spectroscopies. X-ray analysis have confirmed that the compound crystallized in the monoclinic group Cc as an inversion twin. The asymmetric unit contains two symmetrically independent cationic complexes [RuCl(L1)(η6-p-cymene)]+ whose charge is balanced by two PF6- counterions. The shape of each cationic coordination polyhedral can be described as a distorted dodecahedron and shows a typical piano-stool geometry. In addition, an analysis of the crystal structure and the Hirshfeld surface analysis were used to detect and visualize important hydrogen bonds and intermolecular interaction. Moreover, the antiproliferative behavior of the obtained complex was assayed against three human cells: MV-4-11, LoVo, MCF-7 and BALB/3T3 - normal mice fibroblast cells. To predict a binding mode, a potential interaction of ruthenium complex with calf thymus DNA (CT-DNA) has been explored using UV absorption and circular dichroism (CD).

Inert Reassessment Document for Camphor - CAS No. 76-22-2

EPA Pesticide Factsheets

Camphor is used as a topical liniment, preservative in pharmaceuticalsand cosmetics, moth repellant, and plasticizer for esters, as well as in lacquers & varnishes, explosives, embalming fluid, and the manufacture of plastics and cymene.

Refractive index and solubility control of para-cymene solutions for index-matched fluid-structure interaction studies

NASA Astrophysics Data System (ADS)

Fort, Charles; Fu, Christopher D.; Weichselbaum, Noah A.; Bardet, Philippe M.

2015-12-01

To deploy optical diagnostics such as particle image velocimetry or planar laser-induced fluorescence (PLIF) in complex geometries, it is beneficial to use index-matched facilities. A binary mixture of para-cymene and cinnamaldehyde provides a viable option for matching the refractive index of acrylic, a common material for scaled models and test sections. This fluid is particularly appropriate for large-scale facilities and when a low-density and low-viscosity fluid is sought, such as in fluid-structure interaction studies. This binary solution has relatively low kinematic viscosity and density; its use enables the experimentalist to select operating temperature and to increase fluorescence signal in PLIF experiments. Measurements of spectral and temperature dependence of refractive index, density, and kinematic viscosity are reported. The effect of the binary mixture on solubility control of Rhodamine 6G is also characterized.

Reaction of the Anticancer Organometallic Ruthenium Compound, [(η6-p-Cymene)Ru(ATSC)Cl]PF6 with Human Serum Albumin

PubMed Central

Beckford, Floyd A.

2010-01-01

The reaction of [(η6-p-cymene)Ru(ATSC)Cl]PF6 (ATSC = 9-anthraldehyde thiosemicarbazone) with human serum albumin was investigated at different temperatures using fluorescence and infrared spectrophotometry. The binding constant, K, for the reaction was determined using a number of different methods. Using a modified Stern-Volmer equation, K was determined to be 9.09 × 104, 12.1 × 104, and 13.1 × 104 M−1 at 293 K, 298 K, and 308 K, respectively. A thermodynamic analysis showed that the reaction is spontaneous with ΔG being negative. The enthalpy of reaction ΔH = 16.5kJ mol−1 and the entropy of reaction ΔS = 152 Jmol−1K−1. The values of ΔH and ΔS suggest that hydrophobic forces are dominant in the mode of interaction and that the process is mostly entropy driven. PMID:20671814

Analysis of the essential oil components from different Carum copticum L. samples from Iran.

PubMed

Zarshenas, Mohammad M; Samani, Soliman Mohammadi; Petramfar, Peyman; Moein, Mahmoodreza

2014-01-01

The family Apiaceae is defined with the diversity of essential oil. Fruits of Ajwain (Carum copticum), a famous herb of Apiaceae, accumulate up to 5% essential oil which is remarked as important natural product for food and flavoring industry, as well as pharmacological approaches. It is believed that differences in essential oil profile in a certain plant are resulted from various cultivation situations and locations, time of cultivation and also different extracting method. Present study aimed to evaluate major components of ten different collected Ajwain samples from random cultivation locations of Iran. Samples were individually subjected to hydrodistillation using a Clevenger-type apparatus for the extraction of essential oil. GC/MS analysis for samples was carried out using Agilent technologies model 7890A gas chromatograph with a mass detector. The yield of extracted essential oil was calculated as 2.2 to 4.8% (v/w) for ten samples. Major oil components were thymol, para-cymene and gamma-terpinene. Five of ten samples have thymol as the main component with amount of 35.04 to 63.31%. On the other hand, for four samples, para-cymene was major with amount of 40.20 to 57.31% and one sample had gamma-terpinene as main constituent containing 37.43% of total oil. Accordingly, three different chemotypes, thymol, para-cymene and gamma-terpinene can be speculated from collected samples. While these components possess pharmacological effect, screening of different chemotypes not only represent the effect of cultivation situations and locations but also can be beneficial in further investigation.

PHOTOCHEMISTRY OF SOME NATURALLY EMITTED HYDROCARBONS

EPA Science Inventory

Six C10H16 monoterpenes, p-cymene, and isoprene, all known or thought to be emitted to the atmosphere by vegetation, were irradiated in the presence of NOx. The terpenes studied included one acyclic triolefin (myrcene), two monocyclic diolefins (d-limonene, terpinolene), and thre...

Synthesis, crystal structure and cytotoxic activity of ruthenium(II) piano-stool complex with N,N-chelating ligand

NASA Astrophysics Data System (ADS)

Rogala, Patrycja; Jabłońska-Wawrzycka, Agnieszka; Kazimierczuk, Katarzyna; Borek, Agnieszka; Błażejczyk, Agnieszka; Wietrzyk, Joanna; Barszcz, Barbara

2016-12-01

A mononuclear compound of the general formula [(η6-p-cymene)RuIICl(2,2‧-PyBIm)]PF6 has been synthesized from a bidentate N,N-donor ligand, viz. 2,-(2‧-pyridyl)benzimidazole (2,2‧-PyBIm) and the corresponding chloro-complex [(η6-p-cymene)Ru(μ-Cl)Cl]2 (precursor). The isolated coordination compound was characterized by IR, UV-vis and 1H, 13C NMR spectroscopies. The single crystal X-ray analysis of the complex reveals that the asymmetric part of the unit cell consists of two symmetrically independent, [(η6-p-cymene)RuCl(2,2‧-PyBIm)]+ cationic complexes. Each cation exhibits a pseudo-octahedral three-legged piano-stool geometry, in which three "legs" are occupied by one chloride ion and two nitrogen donor atoms of the chelating ligand 2,2‧-PyBIm. The Hirshfeld surface analysis of obtained complex was determined, too. The ionic nature of the compound is identified by a strong band at around 830 cm-1 due to the νP-F stretching mode of the PF6- counter ion. The electronic spectrum of this monomeric complex displays high intensity bands in the ultraviolet region assignable to π→π*/n→π* transitions, as well as a band attributable to the metal-to-ligand charge transfer (MLCT) dπ(Ru)→π*(L) transition. Additionally, the complex has been screened for its cytotoxicity against three human cancer lines: non-small cell lung carcinoma (A549), colon adenocarcinoma (HT29) and breast adenocarcinoma (MCF-7) as well as normal mice fibroblast cells (BALB/3T3). The complex demonstrated a moderate antiproliferative activity against the cell lines tested.

In Situ Generated Ruthenium-Arene Catalyst for Photoactivated Ring-Opening Metathesis Polymerization through Photolatent N-Heterocyclic Carbene Ligand.

PubMed

Pinaud, Julien; Trinh, Thi Kim Hoang; Sauvanier, David; Placet, Emeline; Songsee, Sriprapai; Lacroix-Desmazes, Patrick; Becht, Jean-Michel; Tarablsi, Bassam; Lalevée, Jacques; Pichavant, Loïc; Héroguez, Valérie; Chemtob, Abraham

2018-01-09

1,3-Bis(mesityl)imidazolium tetraphenylborate (IMesH + BPh 4 - ) can be synthesized in one step by anion metathesis between the corresponding imidazolium chloride and sodium tetraphenylborate. In the presence of 2-isopropylthioxanthone (sensitizer), an IMes N-heterocyclic carbene (NHC) ligand can be photogenerated under irradiation at 365 nm through coupled electron/proton transfer reactions. By combining this tandem NHC photogenerator system with metathesis inactive [RuCl 2 (p-cymene)] 2 precatalyst, the highly active RuCl 2 (p-cymene)(IMes) complex can be formed in situ, enabling a complete ring-opening metathesis polymerization (ROMP) of norbornene in the matter of minutes at room temperature. To the best of our knowledge, this is the first example of a photogenerated NHC. Its exploitation in photoROMP has resulted in a simplified process compared to current photocatalysts, because only stable commercial or easily synthesized reagents are required. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium–arene complexes

PubMed Central

Borguet, Yannick; Sauvage, Xavier; Zaragoza, Guillermo; Demonceau, Albert

2010-01-01

Summary The tandem catalysis of ring-closing metathesis/atom transfer radical reactions was investigated with the homobimetallic ruthenium–indenylidene complex [(p-cymene)Ru(μ-Cl)3RuCl(3-phenyl-1-indenylidene)(PCy3)] (1) to generate active species in situ. The two catalytic processes were first carried out independently in a case study before the whole sequence was optimized and applied to the synthesis of several polyhalogenated bicyclic γ-lactams and lactones from α,ω-diene substrates bearing trihaloacetamide or trichloroacetate functionalities. The individual steps were carefully monitored by 1H and 31P NMR spectroscopies in order to understand the intimate details of the catalytic cycles. Polyhalogenated substrates and the ethylene released upon metathesis induced the clean transformation of catalyst precursor 1 into the Ru(II)–Ru(III) mixed-valence compound [(p-cymene)Ru(μ-Cl)3RuCl2(PCy3)], which was found to be an efficient promoter for atom transfer radical reactions under the adopted experimental conditions. PMID:21160564

Essential Oil from the Resin of Protium heptaphyllum: Chemical Composition, Cytotoxicity, Antimicrobial Activity, and Antimutagenicity.

PubMed

de Lima, Ewelyne Miranda; Cazelli, Didley Sâmia Paiva; Pinto, Fernanda Endringer; Mazuco, Renata Alves; Kalil, Ieda Carneiro; Lenz, Dominik; Scherer, Rodrigo; de Andrade, Tadeu Uggere; Endringer, Denise Coutinho

2016-01-01

Protium heptaphyllum (Aubl.) March is popularly used as an analgesic and anti-inflammatory agent. This study aimed to evaluate the chemical composition of P. heptaphyllum essential oil, its cytotoxicity in a breast cancer cell line (MCF-7), antimicrobial activity, and its antimutagenicity in vivo. The chemical composition of the essential oil collected in three 3 years was determined by gas chromatography-mass spectrometry. The cytotoxicity was evaluated using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Annexin V conjugated with fluorescein isothiocyanate, caspase-3, and tumor necrosis factor-alpha (TNF-α) assays were performed to evaluate apoptosis and inflammatory events. The antimutagenic activity at doses of 25, 50, and 100 mg/kg was determined using a micronucleus test in murine bone marrow. The essential oil showed a predominance of monoterpene compounds, being the terpinolene, p-cymene-8-ol, and p-cymene, present in the essential oil extracted in the 3 years. The essential oil showed a protection against cyclophosphamide-induced genotoxicity, and the cytotoxicity index polychromatic erythrocytes/normochromatic erythrocytes ratio in animals treated with oil at all doses (1.34 ± 0.33; 1.15 ± 0.1; 1.11 ± 0.13) did not differ from the negative control animal (1.31 ± 0.33), but from the cyclophosphamide group (0.61 ± 0.12). Cytotoxicity, at a concentration of 40.0 μg/mL, and antimicrobial activity were not observed for the essential oil (minimum inhibitory concentration ≥0.5 mg/mL). The essential oil did not change the levels of caspase-3 in the TNF-α level. The essential oil showed antimutagenic activity due to its chemical composition. Terpinolene, p-cymene-8-ol, and p-cymene are the main constituents of the essential oil of P. heptaphyllum collected within 3-yearsThe essential oil of P. heptaphyllum did not show antimicrobial activity (MIC >0.5 mg/mL) against E. coli, S. aureus, E. faecalis, and C. albicansThe essential oil of P. heptaphyllum has activity against S. mutans (MIC = 0.5 mg/mL)The essential oil showed a protection against cyclophosphamide-induced genotoxicity in the micronuclei assay. Abbreviations used: GC-MS: Gas Chromatography-Mass Spectrometry, MTT: 3-(4,5dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, Annexin V-FITC: Annexin V conjugated with fluorescein isothiocyanate, TNF-α: Tumor necrosis factor alpha, MIC: Minimum Inhibitory Concentration.

Two new diterpene phenols from Calocedrus decurrans

Treesearch

Sheeba Veluthoor; Shujun Li; Rick G. Kelsey; Marc C. Dolan; Nicholas A. Panella; Joe Karchesy

2010-01-01

Two new p-cymene based diphenols (1-2) were isolated from the heartwood of Calocedrus decurrans. Structures were elucidated by 1D and 2D NMR techniques and HRMS. Libocedroquinone (3) was also isolated as a natural product for the first time. A new system of nomenclature is proposed for description of such oligomeric p...

Management of postharvest grape withering to optimise the aroma of the final wine: A case study on Amarone.

PubMed

Bellincontro, A; Matarese, F; D'Onofrio, C; Accordini, D; Tosi, E; Mencarelli, F

2016-12-15

Amarone wine is different from regular dry wine due to the postharvest withering of Corvina, Corvinone and Rondinella grapes. Grapes were withered in a commercial facility with variability in terms of temperature and relative humidity (R.H.). Sugar content reached 230-240gL(-1) and 280gL(-1) at 20% and 30% mass loss, respectively. Most of VOCs (volatile organic compounds) decreased during withering but few VOCs increased during withering and we considered as markers; in Corvinone they were methylhexanoate, dimethylsuccinate, nerol, nonanoic acid, and benzyl alcohol; in Corvina, benzyl alcohol, isoamyl alcohol, 1-hexanol, p-cymen-8-ol, 2,3 pinanediol, 3-oxo-ionol and 3-methyl-1-pentanol, coumaran and damascenone; in Rondinella, hexanol, nonanoic acid, methyl vanillate, damascenone, 3-oxo-ionol, eugenol, p-cymen-8-ol, 2,3 pinanediol, coumaran and raspberry keton. Olfactive descriptors of the wines and the potential aroma of the combination of Corvina wine with the wines of the other two varieties at different percentages of mass loss are reported. Copyright © 2016 Elsevier Ltd. All rights reserved.

New procedure for extraction of algal lipids from wet biomass: a green clean and scalable process.

PubMed

Dejoye Tanzi, Celine; Abert Vian, Maryline; Chemat, Farid

2013-04-01

A new procedure, called Simultaneous Distillation and Extraction Process (SDEP), for lipid extraction from wet microalgae (Nannochloropsis oculata and Dunaliella salina) was reported. This method does not require a pre-drying of the biomass and employs alternative solvents such as d-limonene, α-pinene and p-cymene. This procedure has been compared with Soxhlet extraction (Sox) and Bligh & Dyer method (B&D). For N. oculata, results showed that SDEP-cymene provided similar lipid yields to B&D (21.45% and 23.78%), while SDEP-limonene and pinene provided lower yields (18.73% and 18.75% respectively). For D. salina, SDEP-pinene provided the maximum lipid yield (3.29%) compared to the other solvents, which is quite close to B&D result (4.03%). No significant differences in terms of distribution of lipid classes and fatty acid composition have been obtained for different techniques. Evaluation of energy consumption indicates a substantial saving in the extraction cost by SDEP compared to the conventional extraction technique, Soxhlet. Copyright © 2013 Elsevier Ltd. All rights reserved.

Chemotyping of diverse Eucalyptus species grown in Egypt and antioxidant and antibacterial activities of its respective essential oils.

PubMed

Salem, Mohamed Z M; Ashmawy, Nader A; Elansary, Hosam O; El-Settawy, Ahmed A

2015-01-01

The chemical composition of the essential oil from the leaves of Eucalyptus camaldulensis, Eucalyptus camaldulensis var. obtusa and Eucalyptus gomphocephala grown in northern Egypt was analysed by using GC-FID and GC-MS techniques. The antibacterial (agar disc diffusion and minimum inhibitory concentration methods) and antioxidant activities (2,2'-diphenypicrylhydrazyl) were examined. The main oils constituents were 1,8-cineole (21.75%), β-pinene (20.51%) and methyleugenol (6.10%) in E. camaldulensis; spathulenol (37.46%), p-cymene (17.20%) and crypton (8.88%) in E. gomphocephala; spathulenol (18.37%), p-cymene (19.38%) and crypton (16.91%) in E. camaldulensis var. obtusa. The essential oils from the leaves of Eucalyptus spp. exhibited considerable antibacterial activity against Gram-positive and Gram-negative bacteria. The values of total antioxidant activity were 70 ± 3.13%, 50 ± 3.34% and 84 ± 4.64% for E. camaldulensis, E. camaldulensis var. obtusa and E. gomphocephala, respectively. The highest antioxidant activity value of 84 ± 4.64% could be attributed to the high amount of spathulenol (37.46%).

Experiments in Thermodynamics and Kinetics of Phosphine Substitution in (p-Cymene)RuCl[subscript 2](PR[subscript 3])

ERIC Educational Resources Information Center

Ozerov, Oleg V.; Fafard, Claudia M.; Hoffman, Norris W.

2007-01-01

This manuscript describes a set of three experiments that investigates the thermodynamic and kinetic aspects of phosphine substitution at a Ru center. In the first experiment, the students synthesize a Ru organometallic complex containing a phosphine ligand. In the second, equilibria for phosphine substitution involving several different…

Repellency of the Origanum onites L. Essential Oil and Constituents to the Lone Star Tick and Yellow Fever Mosquito

USDA-ARS?s Scientific Manuscript database

The oregano, Origanum onites L., essential oil (EO) was tested in laboratory behavioral bioassays for repellent activity against Amblyomma americanum (L.) and Aedes aegypti (L.). The O. onites EO was characterized using GC-FID and GC-MS. Carvacrol (75.70 %), linalool (9.0 %), p-cymene (4.33 %) and t...

Alternative control of Aedes aegypti resistant to pyrethroids: lethal and sublethal effects of monoterpene bioinsecticides.

PubMed

Silva, Indira Ma; Martins, Gustavo F; Melo, Carlisson R; Santana, Alisson S; Faro, Ruan Rn; Blank, Arie F; Alves, Péricles B; Picanço, Marcelo C; Cristaldo, Paulo F; Araújo, Ana Paula A; Bacci, Leandro

2018-04-01

The mosquito Aedes aegypti is intensively controlled because it is a vector of viruses that cause numerous diseases, especially in tropical regions. As a consequence of the indiscriminate use of insecticides, populations from different regions have become resistant to pyrethroids. Here, we analyzed the lethal and sublethal effects of essential oil of Aristolochia trilobata and its major compounds on A. aegypti from susceptible and pyrethroid-resistant populations. Our results showed that the toxicity of the different compounds and behavioral changes in response to them are dependent on the stage of the insect life cycle. The monoterpene ρ-cymene caused high mortality in both larvae and adult females of A. aegypti, including those from the pyrethroid-resistant population. The monoterpenes limonene and linalool caused a sublethal effect in the larvae, triggering changes in the swimming pattern. This study highlights the potential of the essential oil of A. trilobata and its major compounds ρ-cymene and limonene for the control of A. aegypti and reveals the importance of analyzing sublethal effects on the population dynamics of the A. aegypti mosquito. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Essential Oils of Echinophora lamondiana (Apiales: Umbelliferae): A Relationship Between Chemical Profile and Biting Deterrence and Larvicidal Activity Against Mosquitoes (Diptera: Culicidae)

DTIC Science & Technology

2015-01-01

majority of compounds. Essential oil from herbal parts of E. lamondiana is reported to be rich in d-3-carene (48%), a-phellandrene (28%), and p-cymene (7...of six Echinophora species from Turkey. J. Essent. Oil Res. 10: 345–351. Baytop, T. 1984. Therapy with medicinal plants in Turkey (Past and Present

Internal flow characteristics in scaled pressure-swirl atomizer

NASA Astrophysics Data System (ADS)

Malý, Milan; Sapík, Marcel; Jedelský, Jan; Janáčková, Lada; Jícha, Miroslav; Sláma, Jaroslav; Wigley, Graham

2018-06-01

Pressure-swirl atomizers are used in a wide range of industrial applications, e.g.: combustion, cooling, painting, food processing etc. Their spray characteristics are closely linked to the internal flow which predetermines the parameters of the liquid sheet formed at the discharge orifice. To achieve a better understanding of the spray formation process, the internal flow was characterised using Laser Doppler Anemometry (LDA) and high-speed imaging in a transparent model made of cast PMMA (Poly(methyl methacrylate)). The design of the transparent atomizer was derived from a pressure-swirl atomizer as used in a small gas turbine. Due to the small dimensions, it was manufactured in a scale of 10:1. It has modular concept and consists of three parts which were ground, polished and bolted together. The original kerosene-type jet A-1 fuel had to be replaced due to the necessity of a refractive index match. The new working liquid should also be colourless, non-aggressive to the PMMA and have the appropriate viscosity to achieve the same Reynolds number as in the original atomizer. Several liquids were chosen and tested to satisfy these requirements. P-Cymene was chosen as the suitable working liquid. The internal flow characteristics were consequently examined by LDA and high-speed camera using p-Cymene and Kerosene-type jet A-1 in comparative manner.

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

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.

Chemical Composition, Enantiomeric Distribution, and Antifungal Activity of the Oleoresin Essential Oil of Protium amazonicum from Ecuador.

PubMed

Satyal, Prabodh; Powers, Chelsea N; Parducci V, Rafael; McFeeters, Robert L; Setzer, William N

2017-09-23

Background: Protium species (Burseraceae) have been used in the treatment of various diseases and conditions such as ulcers and wounds. Methods: The essential oil from the oleoresin of Protium amazonicum was obtained by hydrodistillation and analyzed by GC-MS, GC-FID, and chiral GC-MS. P. amazonicum oleoresin oil was screened for antifungal activity against Candida albicans , Aspergillus niger , and Cryptococcus neoformans . Results: A total of 54 components representing 99.6% of the composition were identified in the oil. The essential oil was dominated by δ-3-carene (47.9%) with lesser quantities of other monoterpenoids α-pinene (4.0%), p -cymene (4.1%), limonene (5.1%), α-terpineol (5.5%) and p -cymen-8-ol (4.8%). Chiral GC-MS revealed most of the monoterpenoids to have a majority of levo enantiomers present with the exceptions of limonene and α-terpineol, which showed a dextro majority. P. amazonicum oleoresin oil showed promising activity against Cryptococcus neoformans , with MIC = 156 μg/mL. Conclusions: This account is the first reporting of both the chemical composition and enantiomeric distribution of the oleoresin essential oil of P. amazonicum from Ecuador. The oil was dominated by (-)-δ-3-carene, and this compound, along with other monoterpenoids, likely accounts for the observed antifungal activity of the oil.

Homobimetallic Ruthenium-N-Heterocyclic Carbene Complexes For Olefin Metathesis

NASA Astrophysics Data System (ADS)

Sauvage, Xavier; Demonceau, Albert; Delaude, Lionel

In this chapter, the synthesis and catalytic activity towards olefin metathesis of homobimetallic ruthenium (Ru)-alkylidene, -cyclodiene or -arene complexes bearing phosphine or N-heterocyclic carbene (NHC) ligands are reviewed. Emphasis is placed on the last category of bimetallic compounds. Three representatives of this new type of molecular scaffold were investigated. Thus, [(p-cymene)Ru(m-Cl)3RuCl (h2-C2H4)(L)] complexes with L = PCy3 (15a), IMes (16a), or IMesCl2 (16b) were prepared. They served as catalyst precursors for cross-metathesis (CM) of various styrene derivatives. These experiments revealed the outstanding aptitude of complex 16a (and to a lesser extent of 16b) to catalyze olefin metathesis reactions. Contrary to monometallic Ru-arene complexes of the [RuCl2(p-cymene)(L)] type, the new homobimetallic species did not require the addition of a diazo compound nor visible light illumination to initiate the ring-opening metathesis of norbornene or cyclooctene. When diethyl 2,2-diallylmalonate and N,N-diallyltosylamide were exposed to 16a,b, a mixture of cycloisomerization and ring-closing metathesis (RCM) products was obtained in a nonselective way. Addition of phenylacetylene enhanced the metathetical activity while completely repressing the cycloisomerization process.

Chemical Composition, Enantiomeric Distribution, and Antifungal Activity of the Oleoresin Essential Oil of Protium amazonicum from Ecuador

PubMed Central

Satyal, Prabodh; Powers, Chelsea N.; Parducci V., Rafael; McFeeters, Robert L.; Setzer, William N.

2017-01-01

Background: Protium species (Burseraceae) have been used in the treatment of various diseases and conditions such as ulcers and wounds. Methods: The essential oil from the oleoresin of Protium amazonicum was obtained by hydrodistillation and analyzed by GC-MS, GC-FID, and chiral GC-MS. P. amazonicum oleoresin oil was screened for antifungal activity against Candida albicans, Aspergillus niger, and Cryptococcus neoformans. Results: A total of 54 components representing 99.6% of the composition were identified in the oil. The essential oil was dominated by δ-3-carene (47.9%) with lesser quantities of other monoterpenoids α-pinene (4.0%), p-cymene (4.1%), limonene (5.1%), α-terpineol (5.5%) and p-cymen-8-ol (4.8%). Chiral GC-MS revealed most of the monoterpenoids to have a majority of levo enantiomers present with the exceptions of limonene and α-terpineol, which showed a dextro majority. P. amazonicum oleoresin oil showed promising activity against Cryptococcus neoformans, with MIC = 156 μg/mL. Conclusions: This account is the first reporting of both the chemical composition and enantiomeric distribution of the oleoresin essential oil of P. amazonicum from Ecuador. The oil was dominated by (−)-δ-3-carene, and this compound, along with other monoterpenoids, likely accounts for the observed antifungal activity of the oil. PMID:28946630

Chemical characterization of emissions from a municipal solid waste treatment plant.

PubMed

Moreno, A I; Arnáiz, N; Font, R; Carratalá, A

2014-11-01

Gaseous emissions are an important problem in municipal solid waste (MSW) treatment plants. The sources points of emissions considered in the present work are: fresh compost, mature compost, landfill leaks and leachate ponds. Hydrogen sulphide, ammonia and volatile organic compounds (VOCs) were analysed in the emissions from these sources. Hydrogen sulphide and ammonia were important contributors to the total emission volume. Landfill leaks are significant source points of emissions of H2S; the average concentration of H2S in biogas from the landfill leaks is around 1700 ppmv. The fresh composting site was also an important contributor of H2S to the total emission volume; its concentration varied between 3.2 and 1.7 ppmv and a decrease with time was observed. The mature composting site showed a reduction of H2S concentration (<0.1 ppmv). Leachate pond showed a low concentration of H2S (in order of ppbv). Regarding NH3, composting sites and landfill leaks are notable source points of emissions (composting sites varied around 30-600 ppmv; biogas from landfill leaks varied from 160 to 640 ppmv). Regarding VOCs, the main compounds were: limonene, p-cymene, pinene, cyclohexane, reaching concentrations around 0.2-4.3 ppmv. H2S/NH3, limonene/p-cymene, limonene/cyclohexane ratios can be useful for analysing and identifying the emission sources. Copyright © 2014 Elsevier Ltd. All rights reserved.

Sweetening ruthenium and osmium: organometallic arene complexes containing aspartame.

PubMed

Gray, Jennifer C; Habtemariam, Abraha; Winnig, Marcel; Meyerhof, Wolfgang; Sadler, Peter J

2008-09-01

The novel organometallic sandwich complexes [(eta(6)-p-cymene)Ru(eta(6)-aspartame)](OTf)(2) (1) (OTf = trifluoromethanesulfonate) and [(eta(6)-p-cymene)Os(eta(6)-aspartame)](OTf)(2) (2) incorporating the artificial sweetener aspartame have been synthesised and characterised. A number of properties of aspartame were found to be altered on binding to either metal. The pK(a) values of both the carboxyl and the amino groups of aspartame are lowered by between 0.35 and 0.57 pH units, causing partial deprotonation of the amino group at pH 7.4 (physiological pH). The rate of degradation of aspartame to 3,6-dioxo-5-phenylmethylpiperazine acetic acid (diketopiperazine) increased over threefold from 0.12 to 0.36 h(-1) for 1, and to 0.43 h(-1) for 2. Furthermore, the reduction potential of the ligand shifted from -1.133 to -0.619 V for 2. For the ruthenium complex 1 the process occurred in two steps, the first (at -0.38 V) within a biologically accessible range. This facilitates reactions with biological reductants such as ascorbate. Binding to and activation of the sweet taste receptor was not observed for these metal complexes up to concentrations of 1 mM. The factors which affect the ability of metal-bound aspartame to interact with the receptor site are discussed.

Fatty acids, essential oil, and phenolics modifications of black cumin fruit under NaCl stress conditions.

PubMed

Bourgou, Soumaya; Bettaieb, Iness; Saidani, Moufida; Marzouk, Brahim

2010-12-08

This research evaluated the effect of saline conditions on fruit yield, fatty acids, and essential oils compositions and phenolics content of black cumin (Nigella sativa). This plant is one of the most commonly found aromatics in the Mediterranean kitchen. Increasing NaCl levels to 60 mM decreased significantly the fruits yield by 58% and the total fatty acids amount by 35%. Fatty acids composition analysis indicated that linoleic acid was the major fatty acid (58.09%) followed by oleic (19.21%) and palmitic (14.77%) acids. Salinity enhanced the linoleic acid percentage but did not affect the unsaturation degree of the fatty acids pool and thus the oil quality. The essential oil yield was 0.39% based on the dry weight and increased to 0.53, 0.56, and 0.72% at 20, 40, and 60 mM NaCl. Salinity results on the modification of the essential oil chemotype from p-cymene in controls to γ-terpinene/p-cymene in salt-stressed plants. The amounts of total phenolics were lower in the treated plants. Salinity decreased mainly the amount of the major class, benzoics acids, by 24, 29, and 44% at 20, 40, and 60 mM NaCl. The results suggest that salt treatment may regulate bioactive compounds production in black cumin fruits, influencing their nutritional and industrial values.

Orchids and Bee's Knees: Investigating the Euglossine Syndrome with Gas Chromatography/Fourier Transform Infrared GC/FT-IR

NASA Astrophysics Data System (ADS)

McClure, Gregory L.; Williams, N. H...; Whitten, W. M.

1985-12-01

The GC/FT-IR analysis of a fragrance obtained from a Gongora tricolor orchid is described. The significance of this type of analysis is explained in terms of the elucidation of the complex relationship between orchids and bees known as "The Euglossine Syndrome". The fragrance sample was found to contain p-cresol, p-methylanisole and a variety of terpenoids, including myrcene, cineole, limonene, cymene, ipsdienol, and an olefinic product which appears to be the dehydration product of ipsdienol.

Incorporation of organometallic Ru complexes into apo-ferritin cage.

PubMed

Takezawa, Yusuke; Böckmann, Philipp; Sugi, Naoki; Wang, Ziyue; Abe, Satoshi; Murakami, Tatsuya; Hikage, Tatsuo; Erker, Gerhard; Watanabe, Yoshihito; Kitagawa, Susumu; Ueno, Takafumi

2011-03-14

Spherical protein cages such as an iron storage protein, ferritin, have great potential as nanometer-scale capsules to assemble and store metal ions and complexes. We report herein the synthesis of a composite of an apo-ferritin cage and Ru(p-cymene) complexes. Ru complexes were efficiently incorporated into the ferritin cavity without degradation of its cage structure. X-Ray crystallography revealed that the Ru complexes were immobilized on the interior surface of the cage mainly by the coordination of histidine residues.

Essential Oils of Myrtaceae Species Growing Wild in Tunisia: Chemical Variability and Antifungal Activity Against Biscogniauxia mediterranea, the Causative Agent of Charcoal Canker.

PubMed

Yangui, Islem; Zouaoui Boutiti, Meriem; Boussaid, Mohamed; Messaoud, Chokri

2017-07-01

The chemical composition of five Eucalyptus species and five Myrtus communis L. populations was investigated using GC/MS and GC-FID. For Eucalyptus essential oils, 32 compounds, representing 88.56 - 96.83% of the total oil according to species, were identified. The main compounds were 1,8-cineole, α-pinene, p-cymene, γ-gurjunene, α-aromadendrene, and β-phellandrene. For Myrtle essential oils, 26 compounds, representing 93.13 - 98.91% of the total oil were identified. α-Pinene, 1,8-cineole, linalool, and myrtenyl acetate were found to be the major compounds. Principal component analysis (PCA) showed chemical differentiation between Eucalyptus species and between Myrtle populations. Biscogniauxia mediterranea, the causative agent of charcoal canker, was identified according to its morphological and molecular characteristics. Essential oils of the investigated Eucalyptus species and Myrtle populations were tested for their antifungal capacity against this fungus. The antifungal activity varied according to the essential oil composition. Biscogniauxia mediterranea exhibited powerful resistance to some essential oils including them of Eucalyptus lehmannii and Eucalyptus sideroxylon but it was very sensitive to Eucalyptus camaldulensis oil (IC 50  = 3.83 mg/ml) and M. communis oil from Zaghouan (IC 50  = 1 mg/ml). This sensitivity was found to be correlated to some essential oil compounds such as p-cymene, carvacrol, cuminaldehyde, and linalool. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

Distribution of primary and specialized metabolites in Nigella sativa seeds, a spice with vast traditional and historical uses.

PubMed

Botnick, Ilan; Xue, Wentao; Bar, Einat; Ibdah, Mwafaq; Schwartz, Amnon; Joel, Daniel M; Lev, Efraim; Fait, Aaron; Lewinsohn, Efraim

2012-08-24

Black cumin (Nigella sativa L., Ranunculaceae) is an annual herb commonly used in the Middle East, India and nowadays gaining worldwide acceptance. Historical and traditional uses are extensively documented in ancient texts and historical documents. Black cumin seeds and oil are commonly used as a traditional tonic and remedy for many ailments as well as in confectionery and bakery. Little is known however about the mechanisms that allow the accumulation and localization of its active components in the seed. Chemical and anatomical evidence indicates the presence of active compounds in seed coats. Seed volatiles consist largely of olefinic and oxygenated monoterpenes, mainly p-cymene, thymohydroquinone, thymoquinone, γ-terpinene and α-thujene, with lower levels of sesquiterpenes, mainly longifolene. Monoterpene composition changes during seed maturation. γ-Terpinene and α-thujene are the major monoterpenes accumulated in immature seeds, and the former is gradually replaced by p-cymene, carvacrol, thymo-hydroquinone and thymoquinone upon seed development. These compounds, as well as the indazole alkaloids nigellidine and nigellicine, are almost exclusively accumulated in the seed coat. In contrast, organic and amino acids are primarily accumulated in the inner seed tissues. Sugars and sugar alcohols, as well as the amino alkaloid dopamine and the saponin α-hederin accumulate both in the seed coats and the inner seed tissues at different ratios. Chemical analyses shed light to the ample traditional and historical uses of this plant.

Experience-induced habituation and preference towards non-host plant odors in ovipositing females of a moth.

PubMed

Wang, Hua; Guo, Wen-Fei; Zhang, Peng-Jun; Wu, Zhi-Yi; Liu, Shu-Sheng

2008-03-01

In phytophagous insects, experience can increase positive responses towards non-host plant extracts or induce oviposition on non-host plants, but the underlying chemical and behavioral mechanisms are poorly understood. By using the diamondback moth, Plutella xylostella, its host plant Chinese cabbage, and a non-host plant Chrysanthemum morifolium, as a model system, we observed the experience-altered olfactory responses of ovipositing females towards volatiles of the non-host plant, volatiles of pure chemicals (p-cymene and alpha-terpinene) found in the non-host plant, and volatiles of host plants treated with these chemicals. We assessed the experience-altered oviposition preference towards host plants treated with p-cymene. Naive females showed aversion to the odors of the non-host plant, the pure chemicals, and the pure chemical-treated host plants. In contrast, experienced females either became attracted by these non-host odors or were no longer repelled by these odors. Similarly, naive females laid a significantly lower proportion of eggs on pure chemical-treated host plants than on untreated host plants, but experienced females laid a similar or higher proportion of eggs on pure chemical-treated host plants compared to untreated host plants. Chemical analysis indicated that application of the non-host pure chemicals on Chinese cabbage induced emissions of volatiles by this host plant. We conclude that induced preference for previously repellent compounds is a major mechanism that leads to behavioral changes of this moth towards non-host plants or their extracts.

Cycloruthenated complexes from imine-based heterocycles: synthesis, characterization, and reactivity toward alkynes.

PubMed

Cuesta, Luciano; Soler, Tatiana; Urriolabeitia, Esteban P

2012-11-19

Novel cycloruthenated complexes 2 a-c, 4 a-c, and 6 a, b based on heteroaromatic cores have been synthesized by reaction of a series of heterocycle-based imines with [{RuCl(η(6)-p-cymene)}(2)(μ-Cl)(2)] and Cu(OAc)(2). This approach has proved efficient for the cyclometalation of thiophene, benzothiophene, furan, benzofuran, pyrrole, and indole derivatives. In addition, even a double cyclometalation process over the same heterocyclic ring is possible, yielding unprecedented bimetallic complexes. These ruthenacycles react with 3-hexyne through an unexpected pathway, which involves the coupling of the original imino heterocycle and acetylene followed by dearomatization to afford fused hetero-hydropyridyl ligands bonded to the {Ru(p-cymene)} organometallic moiety (i.e., 7 a-c and 8 a-c). These complexes represent, as far as we know, the first examples of this type of compound within the context of cyclometalation, and an exhaustive analysis of their structure was carried out in solution and solid state. Furthermore, these unique species react with CuCl(2), which promotes the rearomatization and the release of highly valuable aromatic fused bis-heterocycles (i.e., 9 a-c, 10 a-c, 11 a, and 12 a/12 a'), providing a novel and appealing synthetic route to this extraordinary family of molecules. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Isomerization of α-pinene in the terpentin oil with TCA/Natural Zeolite using microwave irradiation

NASA Astrophysics Data System (ADS)

Wijayati, N.; Supartono; Kusumastuti, E.

2018-04-01

The catalytic potensial of trichloroacetic acid (TCA)//Natural Zeolite in the isomerization of α-pinene in the terpentin oil was investigated. The purpose of this study is to investigate the influence of the power of microvawe on activity and selectivity of catalyst. The main product were champhene, terpinene, limonene, p-cymene, and terpinolene. The highest selectivity was 28.26% with a conversion of 23.25%, whereas the higher conversion was 98.99% with selectivity of 16.90% at room temperature using power of microwave 640 W.

Essential oil composition of Eucalyptus microtheca and Eucalyptus viminalis.

PubMed

Maghsoodlou, Malek Taher; Kazemipoor, Nasrin; Valizadeh, Jafar; Falak Nezhad Seifi, Mohsen; Rahneshan, Nahid

2015-01-01

Eucalyptus (Fam. Myrtaceae) is a medicinal plant and various Eucalyptus species possess potent pharmacological actions against diabetes, hepatotoxicity, and inflammation. This study aims to investigate essential oil composition from leaves and flowers of E. microtheca and E. viminalis leaves growing in the Southeast of Iran. The aerial parts of these plants were collected from Zahedan, Sistan and Baluchestan province, Iran in 2013. After drying the plant materials in the shade, the chemical composition of the essential oils was obtained by hydro-distillation method using a Clevenger-type apparatus and analyzed by GC/MS. In the essential oil of E. microtheca leaves, 101 compounds representing 100%, were identified. Among them, α-phellandrene (16.487%), aromadendrene (12.773%), α-pinene (6.752%), globulol (5.997%), ledene (5.665%), P-cymen (5.251%), and β-pinene (5.006%) were the major constituents. In the oil of E. microtheca flowers, 88 compounds representing 100%, were identified in which α-pinene (16.246%), O-cymen (13.522%), β-pinene (11.082%), aromadendrene (7.444%), α-phellandrene (7.006%), globulol (5.419%), and 9-octadecenamide (5.414%) were the major components. Sixty six compounds representing 100% were identified in the oil of E. viminalis leaves. The major compounds were 1, 8-cineole (57.757%), α-pinene (13.379%), limonene (5.443%), and globulol (3.054%). The results showed the essential oils from the aerial parts of Eucalyptus species are a cheap source for the commercial isolation of α-phellandrene, α-pinene, and 1, 8-cineole compounds to be used in medicinal and food products. Furthermore, these plants could be an alternative source of insecticide agents.

The chemistry of (ring)Ru sup 2+ (ring = tetramethylthiophene, p-cymene)

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

Ganja, E.A.; Rauchfuss, T.B.; Stern, C.L.

1991-01-01

Described are the compounds ((ring)Ru(OTf){sub 2}){sub x}, where ring = 2,3,4,5-tetramethylthiophene (TMT, 1), and p-cymene (2). These electrophilic reagents serve as precursors to ((ring)RuL{sub 3}){sup 2+}, where L{sub 3} = (H{sub 2}O){sub 3}, (NH{sub 3}){sub 3}, and (PH{sub 3}){sub 3}. Solutions of 1 and 2 react with carbon monoxide to give (ring)Ru(CO)(OTf){sub 2}. The addition of thiophenes to CH{sub 2}Cl{sub 2} solutions of 1 or 2 leads to the precipitation of the sandwich compounds ((ring)(SC{sub 4}R{sub 4})Ru)(OTf){sub 2}, where SC{sub 4}R{sub 4} = thiophene, 2,5-dimethylthiophene, and TMT. ((TMT)Ru(H{sub 2}O){sub 3})(OTf){sub 2} was characterized by single-crystal X-ray crystallography, which established amore » piano-stool geometry with a planar TMT ligand. ((TMT)Ru(D{sub 2}O){sub 3})(OTf){sub 2} decomposes in D{sub 2}O solution at 150C to give ((TMT){sub 2}Ru){sup 2+}, which undergoes selective deuteration at the 2,5-methyl groups. D{sub 2}O solutions of ((TMT){sub 2}Ru){sup 2+} undergo photochemical loss of one TMT ligand in water to give ((TMT)Ru(H{sub 2}O){sub 3}){sup 2+}. A procedure is described for the reversible loading of 1 onto {gamma}-alumina, which in turn was characterized by {sup 13}C CP-MAS NMR spectroscopy.« less

Continuous multistep synthesis of perillic acid from limonene by catalytic biofilms under segmented flow.

PubMed

Willrodt, Christian; Halan, Babu; Karthaus, Lisa; Rehdorf, Jessica; Julsing, Mattijs K; Buehler, Katja; Schmid, Andreas

2017-02-01

The efficiency of biocatalytic reactions involving industrially interesting reactants is often constrained by toxification of the applied biocatalyst. Here, we evaluated the combination of biologically and technologically inspired strategies to overcome toxicity-related issues during the multistep oxyfunctionalization of (R)-(+)-limonene to (R)-(+)-perillic acid. Pseudomonas putida GS1 catalyzing selective limonene oxidation via the p-cymene degradation pathway and recombinant Pseudomonas taiwanensis VLB120 were evaluated for continuous perillic acid production. A tubular segmented-flow biofilm reactor was used in order to relieve oxygen limitations and to enable membrane mediated substrate supply as well as efficient in situ product removal. Both P. putida GS1 and P. taiwanensis VLB120 developed a catalytic biofilm in this system. The productivity of wild-type P. putida GS1 encoding the enzymes for limonene bioconversion was highly dependent on the carbon source and reached 34 g L tube -1  day -1 when glycerol was supplied. More than 10-fold lower productivities were reached irrespective of the applied carbon source when the recombinant P. taiwanensis VLB120 harboring p-cymene monooxygenase and p-cumic alcohol dehydrogenase was used as biocatalyst. The technical applicability for preparative perillic acid synthesis in the applied system was verified by purification of perillic acid from the outlet stream using an anion exchanger resin. This concept enabled the multistep production of perillic acid and which might be transferred to other reactions involving volatile reactants and toxic end-products. Biotechnol. Bioeng. 2017;114: 281-290. © 2016 Wiley Periodicals, Inc. © 2016 Wiley Periodicals, Inc.

Detecting insect infestation with poly3-hexylthiophenethin thin film sensor

NASA Astrophysics Data System (ADS)

Weerakoon, Kanchana; Li, Suiquing; Shu, Hungjen J.; Chin, Bryan A.

2009-05-01

The financial losses and destruction of crops due to insect infestation in the United States are estimated by the USDA to exceed 20 billion dollars annually. Much of these losses could be avoided by having a sensor that could effectively identify the early stages of insect infestation. However, traditional detection methods are time consuming, require trained personnel, and are not sufficient for early detection. Several previous research studies showed that emitting organic volatile compounds is a defensive mechanism activated by some plant species after being attacked by herbivores and parasites. Corn, cotton, pine, Brussels sprouts when attacked by Beet army worm, spider mites, bark beetles and caterpillars respectively, emits different blends of plant volatiles including γ-terpinene, α-pinene, p-cymene, farnesene, limonene and cis-hexenyl acetate, with a concentration of about 50 ppm. Therefore, monitoring for these volatile compounds may enable on-site early detection of insect infestations. In this study, a chemical resistor sensor to detect plant volatiles was designed and fabricated. The sensor platform consists of micro electronically fabricated interdigitated electrodes. On to this platform, a poly3-hexylthiophene (P3HT) thin film was deposited, using a spin coater at 8000 rpm for 30 seconds. The sensor was tested and found to be sensitive to a variety of plant volatiles, including γ-terpinene, α-pinene, p-cymene, farnesene, limonene and cis-hexenyl acetate at room temperature. These vapors interacted with the P3HT film causing an increase in the resistance of the sensor by more than one order of magnitude

Chemical profile and pharmacological effects of the resin and essential oil from Bursera slechtendalii: A medicinal "copal tree" of southern Mexico.

PubMed

Villa-Ruano, Nemesio; Pacheco-Hernández, Yesenia; Becerra-Martínez, Elvia; Zárate-Reyes, José Alejo; Cruz-Durán, Ramiro

2018-05-16

This study reports on the volatile profile and pharmacological activities of the essential oil and resin from Bursera slechtendalii, an aromatic medicinal tree commercialized in southern Mexico. The essential oil contained 25 volatiles including p-cymen-8-ol (25.4-35.7%), n-hexyl hexanoate (6.8-17.6%) and n-octyl hexanoate (7.6-14.8%), whereas the crystallized resin contained 14 volatiles, including n-octyl acetate (29.6-34.2%), limonene (15.8-18.7%) and n-octyl butyrate (12.6-17-6%). The inhalation of vapors from the resin and essential oil caused a significant anxiolytic-like effect (p < .01) in ICR mice after 20 min of exposure at a dose of 50-150 mg L -1 . The prolonged inhalation of the essential oil (for 40 days, for 15 min, twice a day) produced a significant decrease (p < .01) in total cholesterol and LDL-c content as well as an increase of HDL-c levels in the same murine model. Interestingly, levels of hepatic lipid hydroperoxide decreased, whereas the hepatic activity of superoxide dismutase and glutathione peroxidase was significantly enhanced (P < .05). The detection of p-cymen-8-ol and n-octyl acetate in the plasma of mice strongly suggests their bioavailability and possible role in the biological activities described herein. Also, both the resin and essential oil from B. slechtendalii, as well as their main volatiles, showed a potent repellence activity against Aedes aegypti (p < .01). Copyright © 2018 Elsevier B.V. All rights reserved.

Assessing the chemotaxis behavior of Physarum polycephalum to a range of simple volatile organic chemicals.

PubMed

de Lacy Costello, Ben P J; Adamatzky, Andrew I

2013-09-01

The chemotaxis behavior of the plasmodial stage of the true slime mold Physarum Polycephalum was assessed when given a binary choice between two volatile organic chemicals (VOCs) placed in its environment. All possible binary combinations were tested between 19 separate VOCs selected due to their prevalence and biological activity in common plant and insect species. The slime mold exhibited positive chemotaxis toward a number of VOCs with the following order of preference:   Farnesene > β-myrcene > tridecane > limonene > p-cymene > 3-octanone > β-pinene > m-cresol > benzylacetate > cis-3-hexenylacetate. For the remaining compounds, no positive chemotaxis was observed in any of the experiments, and for most compounds there was an inhibitory effect on the growth of the slime mold. By assessing this lack of growth or failure to propagate, it was possible to produce a list of compounds ranked in terms of their inhibitory effect: nonanal > benzaldehyde > methylbenzoate > linalool > methyl-p-benzoquinone > eugenol > benzyl alcohol > geraniol > 2-phenylethanol. This analysis shows a distinct preference of the slime mold for non-oxygenated terpene and terpene-like compounds (farnesene, β-myrcene, limonene, p-cymene and β-pinene). In contrast, terpene-based alcohols such as geraniol and linalool were found to have a strong inhibitory effect on the slime mold. Both the aldehydes utilized in this study had the strongest inhibitory effect on the slime mold of all the 19 VOCs tested. Interestingly, 3-octanone, which has a strong association with a "fungal odor," was the only compound with an oxygenated functionality where Physarum Polycephalum exhibits distinct positive chemotaxis.

Assessing the chemotaxis behavior of Physarum polycephalum to a range of simple volatile organic chemicals

PubMed Central

de Lacy Costello, Ben P.J.; Adamatzky, Andrew I.

2013-01-01

The chemotaxis behavior of the plasmodial stage of the true slime mold Physarum Polycephalum was assessed when given a binary choice between two volatile organic chemicals (VOCs) placed in its environment. All possible binary combinations were tested between 19 separate VOCs selected due to their prevalence and biological activity in common plant and insect species. The slime mold exhibited positive chemotaxis toward a number of VOCs with the following order of preference:   Farnesene > β-myrcene > tridecane > limonene > p-cymene > 3-octanone > β-pinene > m-cresol > benzylacetate > cis-3-hexenylacetate. For the remaining compounds, no positive chemotaxis was observed in any of the experiments, and for most compounds there was an inhibitory effect on the growth of the slime mold. By assessing this lack of growth or failure to propagate, it was possible to produce a list of compounds ranked in terms of their inhibitory effect: nonanal > benzaldehyde > methylbenzoate > linalool > methyl-p-benzoquinone > eugenol > benzyl alcohol > geraniol > 2-phenylethanol. This analysis shows a distinct preference of the slime mold for non-oxygenated terpene and terpene-like compounds (farnesene, β-myrcene, limonene, p-cymene and β-pinene). In contrast, terpene-based alcohols such as geraniol and linalool were found to have a strong inhibitory effect on the slime mold. Both the aldehydes utilized in this study had the strongest inhibitory effect on the slime mold of all the 19 VOCs tested. Interestingly, 3-octanone, which has a strong association with a “fungal odor,” was the only compound with an oxygenated functionality where Physarum Polycephalum exhibits distinct positive chemotaxis. PMID:24265848

Phytochemical, chromatographic and spectroscopic investigation of Carum copticum seeds and their potential as immunomodulatory agents.

PubMed

Sonar, Pankaj K; Singh, Ranjit; Saraf, Shailendra K

2016-01-01

Carum copticum seeds have been prescribed in the traditional system of medicine for the treatment of immune disorders, such as asthma and rheumatism. The objective of this study was to determine immunomodulatory effects of the alcoholic extract and isolated compounds in Swiss albino mice. Seeds of C. copticum were extracted with 95% v/v alcohol. The immunomodulatory activity of the crude extract was evaluated at the doses of 100, 300, and 500 mg/kg body weight of mice, administered in mice once daily (orally) for 25 days. Volatile oil of C. copticum was isolated by steam distillation and was characterized by GLC and HPLC. Bio-assay-guided fractionation and isolation were carried out and the isolated compounds were characterized and subjected to immunomodulatory activity studies. The n-hexane fraction yielded p-cymene, carvacrol, and α-pinene. The LD50 value of the crude extract was found to be 4500 mg/kg and the values reported for p-cymene, carvacrol, and α-pinene in the literature were 4750, 810, and 3700 mg/kg, respectively. The oral administration of crude extract, n-hexane fraction (HEF), and isolated oils at the dose of 500, 150, and 50 mg/kg body weight, respectively, showed a significant increase in the HA titers, DTH-response, and phagocytosis. The stimulatory effect observed, on humoral and cellular immunity, was compared with the standard (levamisole treated) and control groups. The results obtained in the study endorse the traditional use of the seeds of C. copticum and the isolated constituents act as immunostimulants.

A novel dual-functioning ruthenium(II)-arene complex of an anti-microbial ciprofloxacin derivative - Anti-proliferative and anti-microbial activity.

PubMed

Ude, Ziga; Romero-Canelón, Isolda; Twamley, Brendan; Fitzgerald Hughes, Deirdre; Sadler, Peter J; Marmion, Celine J

2016-07-01

7-(4-(Decanoyl)piperazin-1-yl)-ciprofloxacin, CipA, (1) which is an analogue of the antibiotic ciprofloxacin, and its ruthenium(II) complex [Ru(η(6)-p-cymene)(CipA-H)Cl], (2) have been synthesised and the x-ray crystal structures of 1·1.3H2O·0.6CH3OH and 2·CH3OH·0.5H2O determined. The complex adopts a typical pseudo-octahedral 'piano-stool' geometry, with Ru(II) π-bonded to the p-cymene ring and σ-bonded to a chloride and two oxygen atoms of the chelated fluoroquinolone ligand. The complex is highly cytotoxic in the low μM range and is as potent as the clinical drug cisplatin against the human cancer cell lines A2780, A549, HCT116, and PC3. It is also highly cytotoxic against cisplatin- and oxaliplatin-resistant cell lines suggesting a different mechanism of action. The complex also retained low μM cytotoxicity against the human colon cancer cell line HCT116p53 in which the tumour suppressor p53 had been knocked out, suggesting that the potent anti-proliferative properties associated with this complex are independent of the status of p53 (in contrast to cisplatin). The complex also retained moderate anti-bacterial activity in two Escherichia coli, a laboratory strain and a clinical isolate resistant to first, second and third generation β-lactam antibiotics. Copyright © 2016 The Authors. Published by Elsevier Inc. All rights reserved.

Distillation Time as Tool for Improved Antimalarial Activity and Differential Oil Composition of Cumin Seed Oil.

PubMed

Zheljazkov, Valtcho D; Gawde, Archana; Cantrell, Charles L; Astatkie, Tess; Schlegel, Vicki

2015-01-01

A steam distillation extraction kinetics experiment was conducted to estimate essential oil yield, composition, antimalarial, and antioxidant capacity of cumin (Cuminum cyminum L.) seed (fruits). Furthermore, regression models were developed to predict essential oil yield and composition for a given duration of the steam distillation time (DT). Ten DT durations were tested in this study: 5, 7.5, 15, 30, 60, 120, 240, 360, 480, and 600 min. Oil yields increased with an increase in the DT. Maximum oil yield (content, 2.3 g/100 seed), was achieved at 480 min; longer DT did not increase oil yields. The concentrations of the major oil constituents α-pinene (0.14-0.5% concentration range), β-pinene (3.7-10.3% range), γ-cymene (5-7.3% range), γ-terpinene (1.8-7.2% range), cumin aldehyde (50-66% range), α-terpinen-7-al (3.8-16% range), and β-terpinen-7-al (12-20% range) varied as a function of the DT. The concentrations of α-pinene, β-pinene, γ-cymene, γ-terpinene in the oil increased with the increase of the duration of the DT; α-pinene was highest in the oil obtained at 600 min DT, β-pinene and γ-terpinene reached maximum concentrations in the oil at 360 min DT; γ-cymene reached a maximum in the oil at 60 min DT, cumin aldehyde was high in the oils obtained at 5-60 min DT, and low in the oils obtained at 240-600 min DT, α-terpinen-7-al reached maximum in the oils obtained at 480 or 600 min DT, whereas β-terpinen-7-al reached a maximum concentration in the oil at 60 min DT. The yield of individual oil constituents (calculated from the oil yields and the concentration of a given compound at a particular DT) increased and reached a maximum at 480 or 600 min DT. The antimalarial activity of the cumin seed oil obtained during the 0-5 and at 5-7.5 min DT timeframes was twice higher than the antimalarial activity of the oils obtained at the other DT. This study opens the possibility for distinct marketing and utilization for these improved oils. The antioxidant capacity of the oil was highest in the oil obtained at 30 min DT and lowest in the oil from 360 min DT. The Michaelis-Menton and the Power nonlinear regression models developed in this study can be utilized to predict essential oil yield and composition of cumin seed at any given duration of DT and may also be useful to compare previous reports on cumin oil yield and composition. DT can be utilized to obtain cumin seed oil with improved antimalarial activity, improved antioxidant capacity, and with various compositions.

Comparative Analysis of Flower Volatiles from Nine Citrus at Three Blooming Stages

PubMed Central

Azam, Muhammad; Song, Min; Fan, Fangjuan; Zhang, Bo; Xu, Yaying; Xu, Changjie; Chen, Kunsong

2013-01-01

Volatiles from flowers at three blooming stages of nine citrus cultivars were analyzed by headspace-solid phase microextraction (HS-SPME)-GC-MS. Up to 110 volatiles were detected, with 42 tentatively identified from citrus flowers for the first time. Highest amounts of volatiles were present in fully opened flowers of most citrus, except for pomelos. All cultivars were characterized by a high percentage of either oxygenated monoterpenes or monoterpene hydrocarbons, and the presence of a high percentage of nitrogen containing compounds was also observed. Flower volatiles varied qualitatively and quantitatively among citrus types during blooming. Limonene was the most abundant flower volatile only in citrons; α-citral and β-citral ranked 2nd and 3rd only for Bergamot, and unopened flowers of Ponkan had a higher amount of linalool and β-pinene while much lower amount of γ-terpinene and p-cymene than Satsuma. Taking the average of all cultivars, linalool and limonene were the top two volatiles for all blooming stages; β-pinene ranked 3rd in unopened flowers, while indole ranked 3rd for half opened and fully opened flower volatiles. As flowers bloomed, methyl anthranilate increased while 2-hexenal and p-cymene decreased. In some cases, a volatile could be high in both unopened and fully opened flowers but low in half opened ones. Through multivariate analysis, the nine citrus cultivars were clustered into three groups, consistent with the three true citrus types. Furthermore, an influence of blooming stages on clustering was observed, especially with hybrids Satsuma and Huyou. Altogether, it was suggested that flower volatiles can be suitable markers for revealing the genetic relationships between citrus cultivars but the same blooming stage needs to be strictly controlled. PMID:24232454

Comparative analysis of flower volatiles from nine citrus at three blooming stages.

PubMed

Azam, Muhammad; Song, Min; Fan, Fangjuan; Zhang, Bo; Xu, Yaying; Xu, Changjie; Chen, Kunsong

2013-11-13

Volatiles from flowers at three blooming stages of nine citrus cultivars were analyzed by headspace-solid phase microextraction (HS-SPME)-GC-MS. Up to 110 volatiles were detected, with 42 tentatively identified from citrus flowers for the first time. Highest amounts of volatiles were present in fully opened flowers of most citrus, except for pomelos. All cultivars were characterized by a high percentage of either oxygenated monoterpenes or monoterpene hydrocarbons, and the presence of a high percentage of nitrogen containing compounds was also observed. Flower volatiles varied qualitatively and quantitatively among citrus types during blooming. Limonene was the most abundant flower volatile only in citrons; α-citral and β-citral ranked 2nd and 3rd only for Bergamot, and unopened flowers of Ponkan had a higher amount of linalool and β-pinene while much lower amount of γ-terpinene and p-cymene than Satsuma. Taking the average of all cultivars, linalool and limonene were the top two volatiles for all blooming stages; β-pinene ranked 3rd in unopened flowers, while indole ranked 3rd for half opened and fully opened flower volatiles. As flowers bloomed, methyl anthranilate increased while 2-hexenal and p-cymene decreased. In some cases, a volatile could be high in both unopened and fully opened flowers but low in half opened ones. Through multivariate analysis, the nine citrus cultivars were clustered into three groups, consistent with the three true citrus types. Furthermore, an influence of blooming stages on clustering was observed, especially with hybrids Satsuma and Huyou. Altogether, it was suggested that flower volatiles can be suitable markers for revealing the genetic relationships between citrus cultivars but the same blooming stage needs to be strictly controlled.

Anaerobic Microbial Degradation of Hydrocarbons: From Enzymatic Reactions to the Environment.

PubMed

Rabus, Ralf; Boll, Matthias; Heider, Johann; Meckenstock, Rainer U; Buckel, Wolfgang; Einsle, Oliver; Ermler, Ulrich; Golding, Bernard T; Gunsalus, Robert P; Kroneck, Peter M H; Krüger, Martin; Lueders, Tillmann; Martins, Berta M; Musat, Florin; Richnow, Hans H; Schink, Bernhard; Seifert, Jana; Szaleniec, Maciej; Treude, Tina; Ullmann, G Matthias; Vogt, Carsten; von Bergen, Martin; Wilkes, Heinz

2016-01-01

Hydrocarbons are abundant in anoxic environments and pose biochemical challenges to their anaerobic degradation by microorganisms. Within the framework of the Priority Program 1319, investigations funded by the Deutsche Forschungsgemeinschaft on the anaerobic microbial degradation of hydrocarbons ranged from isolation and enrichment of hitherto unknown hydrocarbon-degrading anaerobic microorganisms, discovery of novel reactions, detailed studies of enzyme mechanisms and structures to process-oriented in situ studies. Selected highlights from this program are collected in this synopsis, with more detailed information provided by theme-focused reviews of the special topic issue on 'Anaerobic biodegradation of hydrocarbons' [this issue, pp. 1-244]. The interdisciplinary character of the program, involving microbiologists, biochemists, organic chemists and environmental scientists, is best exemplified by the studies on alkyl-/arylalkylsuccinate synthases. Here, research topics ranged from in-depth mechanistic studies of archetypical toluene-activating benzylsuccinate synthase, substrate-specific phylogenetic clustering of alkyl-/arylalkylsuccinate synthases (toluene plus xylenes, p-cymene, p-cresol, 2-methylnaphthalene, n-alkanes), stereochemical and co-metabolic insights into n-alkane-activating (methylalkyl)succinate synthases to the discovery of bacterial groups previously unknown to possess alkyl-/arylalkylsuccinate synthases by means of functional gene markers and in situ field studies enabled by state-of-the-art stable isotope probing and fractionation approaches. Other topics are Mo-cofactor-dependent dehydrogenases performing O2-independent hydroxylation of hydrocarbons and alkyl side chains (ethylbenzene, p-cymene, cholesterol, n-hexadecane), degradation of p-alkylated benzoates and toluenes, glycyl radical-bearing 4-hydroxyphenylacetate decarboxylase, novel types of carboxylation reactions (for acetophenone, acetone, and potentially also benzene and naphthalene), W-cofactor-containing enzymes for reductive dearomatization of benzoyl-CoA (class II benzoyl-CoA reductase) in obligate anaerobes and addition of water to acetylene, fermentative formation of cyclohexanecarboxylate from benzoate, and methanogenic degradation of hydrocarbons. © 2016 S. Karger AG, Basel.

Unraveling the polymorphism of [(p-cymene)Ru(κN-INA)Cl₂] through dispersion-corrected DFT and NMR GIPAW calculations.

PubMed

Presti, Davide; Pedone, Alfonso; Menziani, Maria Cristina

2014-08-04

The structural and (13)C/(1)H NMR parameters of the four crystal forms (1α, 1·H2O, 1β, and 1γ) of the solid wheel-and-axle (WAA) metal-organic compound [(p-cymene)Ru(κN-INA)Cl2] have been studied by means of periodic DFT calculations. The quality of the results obtained strongly depends on a correct description of long-range interactions; thus, in the geometry refinement protocol used, the pure DFT functionals need to be coupled with a dispersion-correction term (B3LYP-D2, B3LYP-D*). The solid-state (13)C/(1)H NMR δ(iso) parameters and (13)C MAS NMR spectra, calculated by means of the PBE-GIPAW method, agree well with the experimental data for the four crystal forms (mean absolute deviations of the (13)C and (1)H δ(iso) data values lie in the ranges 1.3-2.9 and 0.3-1.0 ppm, respectively). In this context, some revisions in the experimental assignment of the (13)C/(1)H NMR δ(iso) parameters of the 1·H2O, 1β, and 1γ crystal forms can be suggested. The mismatch in the assignment seems to be due to the rotation of the -COOH moiety, which occurs at the 1α-1·H2O transition and was not considered in the experiments. Finally, the results obtained suggest the presence of two COOH···Cl hydrogen bonds of comparable strength established by the two molecules in the asymmetric unit of the 1γ polymorph, in partial disagreement with previous findings.

Chemical Composition and Biological Activity of Essential Oils from Different Species of Piper from Panama.

PubMed

Santana, Ana I; Vila, Roser; Cañigueral, Salvador; Gupta, Mahabir P

2016-07-01

The chemical composition of leaf essential oils from 11 species of Piper from Panama was analyzed by a combination GC-FID and GC-MS procedures. Six of them had sesquiterpene hydrocarbons as major constituents, three were characterized by monoterpene hydrocarbons, one by a diterpene, and one by a phenylpropanoid, dillapiole. The main components identified in each species were: cembratrienol (25.4 %) in Piper augustum; β-pinene (26.6 %) in Piper corrugatum; α-pinene (19.4 %) in Piper curtispicum; trans-β-farnesene (63.7 %) in Piper darienense; p-cymene (43.9 %) in Piper grande; dillapiole (57.7 %) in Piper hispidum; linalool (14.5 %), α-phellandrene (13.8 %), and limonene (12.2 %) in Piper jacquemontianum; β-caryophyllene (45.2 %) in Piper longispicum; linalool (16.5 %), α-phellandrene (11.8 %), limonene (11.4 %), and p-cymene (9.0 %) in Piper multiplinervium; β-selinene (19.0 %), β-elemene (16.1 %), and α-selinene (15.5 %) in Piper reticulatum; and germacrene D (19.7 %) in Piper trigonum. The essential oils of P. hispidum and P. longispicum at a concentration of 250 µg/mL showed larvicidal activity against Aedes aegypti, while the oils from P. curtispicum, P. multiplinervium, P. reticulatum, and P. trigonum were inactive (LC100 ≥ 500 µg/mL). The essential oils of P. grande, P. jacquemontianum, and P. multiplinervium showed no significant antifungal activity (MIC > 250 µg/mL) against several yeasts and filamentous fungal strains. Georg Thieme Verlag KG Stuttgart · New York.

Biological evaluation of water soluble arene Ru(II) enantiomers with amino-oxime ligands.

PubMed

de la Cueva-Alique, Isabel; Sierra, Sara; Muñoz-Moreno, Laura; Pérez-Redondo, Adrián; Bajo, Ana M; Marzo, Isabel; Gude, Lourdes; Cuenca, Tomás; Royo, Eva

2018-06-01

New water soluble, enantiopure arene ruthenium compound S Ru S N -(1R,4S)-[(η 6 -p-cymene)Ru{ĸNH(Bn),ĸNOH}Cl]Cl (Bn = benzyl, 1a') has been synthesized. The novel compound along with that previously described R Ru R N -(1S,4R)-[(η 6 -p-cymene)Ru{ĸNH(Bn),ĸNOH}Cl]Cl (1a) was evaluated by polarimetry, ultra-violet and circular dichroism spectroscopy. The structure of novel ruthenium derivative 1a' was determined by single crystal X-ray crystallography. Both enantiomers have been tested against several cancer cell lines in vitro: prostate PC-3, lung A-549, pancreas MIA PaCa-2, colorectal HCT-116, leukemia Jurkat and cervical HeLa. Both enantiomers are active and versatile cytotoxic agents, showing IC 50 values from 2 to 12 times lower than those found for cisplatin in the different cell lines evaluated. The mechanism of cell death induced by the metal compounds was analyzed in A-549 and Jurkat cell lines. Derivatives 1a and 1a' induced apoptotic cell death of A-549 cells while dose-dependent cell death mechanisms have been found in the Jurkat cell line. Compound-DNA interactions have been investigated by equilibrium dialysis, Fluorescence Resonance Energy Transfer (FRET) melting assays and viscometric titrations, revealing moderate binding affinity of 1a and 1a' towards duplex DNA. Finally, the efficacy of 1a in a preliminary in vivo assay of PC-3 xenografts in nude mice has been evaluated, resulting in a promising inhibition of tumor growth by 45%. Analysis of tumor tissue also showed a significant decrease of levels of crucial molecules in the invasive phenotype of PC-3 cells. Copyright © 2018 Elsevier Inc. 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.

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

Chemical composition, insecticidal and insect repellent activity of Schinus molle L. leaf and fruit essential oils against Trogoderma granarium and Tribolium castaneum.

PubMed

Abdel-Sattar, Essam; Zaitoun, Ahmed A; Farag, Mohamed A; Gayed, Sabah H El; Harraz, Fathalla M H

2010-02-01

Fruit and leaf essential oils of Schinus molle showed insect repellent and insecticidal activity against Trogoderma granarium and Tribolium castaneum. In these oils, 65 components were identified by GC-MS analysis. Hydrocarbons dominated the oil composition with monoterpenes occurring in the largest amounts in fruits and leaves, 80.43 and 74.84%, respectively. p-Cymene was identified as a major component in both oils. The high yield and efficacy of S. molle essential oil against T. granarium and T. castaneum suggest that it may provide leads for active insecticidal agents.

Chemical composition and in vitro antimicrobial activity of the essential oils of two Helichrysum species from Tanzania.

PubMed

Bougatsos, Christos; Ngassapa, Olipa; Runyoro, Deborah K B; Chinou, Ioanna B

2004-01-01

The chemical composition of the essential oils obtained from the aerial parts of Helichrysum cymosum and H. fulgidum, from Tanzania, were analyzed by GC and GC/MS. A total of sixty-five compounds, representing 92.4% and 88.2% of the two oils, respectively, were identified. trans-Caryophyllene, caryophyllene oxide, beta-pinene, p-cymene, spathulenol and beta-bourbonene were found to be the main components. Furthermore, the oils were tested against six gram (+/-) bacteria and three pathogenic fungi. It was found that the oil of H. fulgidum exhibited significant antimicrobial activity, while the oil of H. cymosum was not active at all.

Antioxidant and repellent activities of the essential oil from Colombian Triphasia trifolia (Burm. f.) P. Wilson.

PubMed

Jaramillo Colorado, Beatriz E; Martelo, Irina P; Duarte, Edisson

2012-06-27

The chemical composition of essential oils isolated from aerial parts of Triphasia trifolia (Burm. f.) P. Wilson was analyzed using hydrodistillation by GC-MS. The main constituents found were β-pinene (64.36%), (+)-sabinene (8.75%), hexadecanoic acid (6.03%), α-limonene (4.24%) and p-cymene (2.73%). The essential oil from T. trifolia shows high antioxidant potential (94.53%), an effect that is comparable with ascorbic acid (96.40%), used as standard. In addition, these oils had high repellent effects on the insect Tribolium castaneum Herbst (99% ± 1) at 0.2 μL/cm(2) after 2 h of exposure.

Distillation Time as Tool for Improved Antimalarial Activity and Differential Oil Composition of Cumin Seed Oil

PubMed Central

Zheljazkov, Valtcho D.; Gawde, Archana; Cantrell, Charles L.; Astatkie, Tess; Schlegel, Vicki

2015-01-01

A steam distillation extraction kinetics experiment was conducted to estimate essential oil yield, composition, antimalarial, and antioxidant capacity of cumin (Cuminum cyminum L.) seed (fruits). Furthermore, regression models were developed to predict essential oil yield and composition for a given duration of the steam distillation time (DT). Ten DT durations were tested in this study: 5, 7.5, 15, 30, 60, 120, 240, 360, 480, and 600 min. Oil yields increased with an increase in the DT. Maximum oil yield (content, 2.3 g/100 seed), was achieved at 480 min; longer DT did not increase oil yields. The concentrations of the major oil constituents α-pinene (0.14–0.5% concentration range), β-pinene (3.7–10.3% range), γ-cymene (5–7.3% range), γ-terpinene (1.8–7.2% range), cumin aldehyde (50–66% range), α-terpinen-7-al (3.8–16% range), and β-terpinen-7-al (12–20% range) varied as a function of the DT. The concentrations of α-pinene, β-pinene, γ-cymene, γ-terpinene in the oil increased with the increase of the duration of the DT; α-pinene was highest in the oil obtained at 600 min DT, β-pinene and γ-terpinene reached maximum concentrations in the oil at 360 min DT; γ-cymene reached a maximum in the oil at 60 min DT, cumin aldehyde was high in the oils obtained at 5–60 min DT, and low in the oils obtained at 240–600 min DT, α-terpinen-7-al reached maximum in the oils obtained at 480 or 600 min DT, whereas β-terpinen-7-al reached a maximum concentration in the oil at 60 min DT. The yield of individual oil constituents (calculated from the oil yields and the concentration of a given compound at a particular DT) increased and reached a maximum at 480 or 600 min DT. The antimalarial activity of the cumin seed oil obtained during the 0–5 and at 5–7.5 min DT timeframes was twice higher than the antimalarial activity of the oils obtained at the other DT. This study opens the possibility for distinct marketing and utilization for these improved oils. The antioxidant capacity of the oil was highest in the oil obtained at 30 min DT and lowest in the oil from 360 min DT. The Michaelis-Menton and the Power nonlinear regression models developed in this study can be utilized to predict essential oil yield and composition of cumin seed at any given duration of DT and may also be useful to compare previous reports on cumin oil yield and composition. DT can be utilized to obtain cumin seed oil with improved antimalarial activity, improved antioxidant capacity, and with various compositions. PMID:26641276

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

Asubay, Sezai; Durap, Feyyaz; Aydemir, Murat

An organic-inorganic junction was fabricated by forming [Ru(Cy{sub 2}PNHCH{sub 2}-C{sub 4}H{sub 3}O)(η{sup 6}-p-cymene)Cl{sub 2}] complex thin film using spin coating technique on n-Si and evaporating Au metal on the film. It was seen that the structure had perfect rectification property. Current-voltage (I-V) measurements were carried out in dark and under various illumination conditions (between 50-100 mW/cm{sup 2}) and with the temperature range from 303 to 380 K. The structure showed unusually forward and reverse bias temperature and light sensing behaviors. It was seen that the current both in forward and reverse bias increased with the increase in light intensity and temperature.

Ruthenium-Catalyzed Cascade C—H Functionalization of Phenylacetophenones**

PubMed Central

Mehta, Vaibhav P; García-López, José-Antonio; Greaney, Michael F

2014-01-01

Three orthogonal cascade C—H functionalization processes are described, based on ruthenium-catalyzed C—H alkenylation. 1-Indanones, indeno indenes, and indeno furanones were accessed through cascade pathways by using arylacetophenones as substrates under conditions of catalytic [{Ru(p-cymene)Cl2}2] and stoichiometric Cu(OAc)2. Each transformation uses C—H functionalization methods to form C—C bonds sequentially, with the indeno furanone synthesis featuring a C—O bond formation as the terminating step. This work demonstrates the power of ruthenium-catalyzed alkenylation as a platform reaction to develop more complex transformations, with multiple C—H functionalization steps taking place in a single operation to access novel carbocyclic structures. PMID:24453063

Calix[4]arene-phosphine dimers: precursors of flexible metallo-capsules and self-compacting molecules.

PubMed

Sameni, Soheila; Jeunesse, Catherine; Matt, Dominique; Toupet, Loïc

2009-10-12

The first diphosphines based on a double calixarene, namely 1,4 (or 1,3)-bis-(5-diphenylphosphino-25,26,27,28-tetrapropoxycalix[4]aren-17-yl)benzene (L(2), L(3)) were each prepared in four steps starting from 5,17-dibromo-25,26,27,28-tetrapropoxycalix[4]arene. Upon reaction of L(2) with [Au(tht)(thf)]BF(4), (tht = C(4)H(8)S) a rigid metallo-capsule was quantitatively formed, which adopts an oblique form owing to the distinct nature of the spacers linking the two calixarene half-spheres. In the solid state, the 1,4-substituted phenylene linker is turned towards the gold ion, suggesting the existence of weak bonding interactions between two aromatic CH protons of this ring and the metal centre (AuH =2.67 A). In contrast to this gold complex, the related silver complex shows dynamic behaviour in solution, the exchange between two enantiomeric oblique forms being facilitated by the greater stereochemical flexibility of Ag(I) vs. Au(I). A heteronuclear (109)Ag{(1)H} HMQC experiment established strong correlations between the CH protons of the phenylene linker and the (109)Ag ion. Dynamic behaviour similar to that observed for the silver complex was further observed in trans-[PtCl(2)L(2)], a chelate complex that could be obtained quantitatively from L(2) and [PtCl(2)(PhCN)(2)]. The intended formation of a chelate complex leading to a capsule with an endo-oriented metal centre was achieved by reacting L(3) with [Pd(allyl)(thf)(2)]BF(4). The complex thus formed constitutes the first organometallic transition metal complex embedded in a cavity with large portals. Binding of [RuCl(2)(p-cymene)] to L(2) and L(3) resulted in self-compacting bimetallic complexes in which each calixarene basket entraps a Ru(p-cymene) unit, thereby forming molecules occupying a minimal volume.

Synthesis, characterization, and anticancer activity of a series of ketone-N(4)-substituted thiosemicarbazones and their ruthenium(II) arene complexes.

PubMed

Su, Wei; Qian, Quanquan; Li, Peiyuan; Lei, Xiaolin; Xiao, Qi; Huang, Shan; Huang, Chusheng; Cui, Jianguo

2013-11-04

A series of ketone-N(4)-substituted thiosemicarbazone (TSC) compounds (L1-L9) and their corresponding [(η(6)-p-cymene)Ru(II)(TSC)Cl](+/0) complexes (1-9) were synthesized and characterized by NMR, IR, elemental analysis, and HR-ESI-mass spectrometry. The molecular structures of L4, L9, 1-6, and 9 were determined by single-crystal X-ray diffraction analysis. The compounds were further evaluated for their in vitro antiproliferative activities against the SGC-7901 human gastric cancer, BEL-7404 human liver cancer, and HEK-293T noncancerous cell lines. Furthermore, the interactions of the compounds with DNA were followed by electrophoretic mobility spectrometry studies.

Biferrocene-Based Diphosphine Ligands: Synthesis and Application of Walphos Analogues in Asymmetric Hydrogenations

PubMed Central

2013-01-01

A total of four biferrocene-based Walphos-type ligands have been synthesized, structurally characterized, and tested in the rhodium-, ruthenium- and iridium-catalyzed hydrogenation of alkenes and ketones. Negishi coupling conditions allowed the biferrocene backbone of these diphosphine ligands to be built up diastereoselectively from the two nonidentical and nonracemic ferrocene fragments (R)-1-(N,N-dimethylamino)ethylferrocene and (SFc)-2-bromoiodoferrocene. The molecular structures of (SFc)-2-bromoiodoferrocene, the coupling product, two ligands, and the two complexes ([PdCl2(L)] and [RuCl(p-cymene)(L)]PF6) were determined by X-ray diffraction. The structural features of complexes and the catalysis results obtained with the newly synthesized biferrocene-based ligands were compared with those of the corresponding Walphos ligands. PMID:23457421

Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis

PubMed Central

2015-01-01

Recent US legislation permitting recreational use of marijuana in certain states brings the use of marijuana odor as probable cause for search and seizure to the forefront of forensic science, once again. This study showed the use of solid-phase microextraction with multidimensional gas chromatography—mass spectrometry and simultaneous human olfaction to characterize the total aroma of marijuana. The application of odor activity analysis offers an explanation as to why high volatile chemical concentration does not equate to most potent odor impact of a certain compound. This suggests that more attention should be focused on highly odorous compounds typically present in low concentrations, such as nonanal, decanol, o-cymene, benzaldehyde, which have more potent odor impact than previously reported marijuana headspace volatiles. PMID:26657499

Chemical Diversity in Lippia alba (Mill.) N. E. Brown Germplasm

PubMed Central

Camêlo, Lídia Cristina Alves; Pinheiro, José Baldin; Andrade, Thiago Matos; Alves, Péricles Barreto

2015-01-01

The aim of this study was to perform chemical characterization of Lippia alba accessions from the Active Germplasm Bank of the Federal University of Sergipe. A randomized block experimental design with two replications was applied. The analysis of the chemical composition of the essential oils was conducted using a gas chromatograph coupled to a mass spectrometer. The chemical composition of the essential oils allowed the accessions to be allocated to the following six groups: group 1: linalool, 1,8-cineole, and caryophyllene oxide; group 2: linalool, geranial, neral, 1,8-cineol, and caryophyllene oxide; group 3: limonene, carvone, and sabinene; group 4: carvone, limonene, g-muurolene, and myrcene; group 5: neral, geranial, and caryophyllene oxide; and group 6: geranial, neral, o-cymene, limonene, and caryophyllene oxide. PMID:26075292

[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.

The influence of arene-ring size on stacking interaction with canonical base pairs

NASA Astrophysics Data System (ADS)

Formánek, Martin; Burda, Jaroslav V.

2014-04-01

Stacking interactions between aromatic molecules (benzene, p-cymene, biphenyl, and di- and tetra-hydrogen anthracene) and G.C and A.T canonical Watson-Crick (WC) base pairs are explored. Two functionals with dispersion corrections: ω-B97XD and B3LYP-D3 are used. For a comparison also the MP2 and B3LYP-D3/PCM methods were used for the most stable p-cymene…WC geometries. It was found that the stacking interaction increases with the size of π-conjugation system. Its extent is in agreement with experimental finding on anticancer activity of Ru(II) piano-stool complexes where intercalation of these aromatic molecules should play an important role. The explored structures are considered as ternary system so that decomposition of the interaction energy to pairwise and non-additivity contributions is also examined.

Identification of volatiles in leaves of Alpinia zerumbet 'Variegata' using headspace solid-phase microextraction-gas chromatography-mass spectrometry.

PubMed

Chen, Jian Yan; Ye, Zheng Mei; Huang, Tian Yi; Chen, Xiao Dan; Li, Yong Yu; Wu, Shao Hua

2014-07-01

Alpinia zerumbet 'Variegata' is an aromatic medicinal plant, its foliage producing an intense, unique fragrant odor. This study identified 46 volatile compounds in the leaf tissue of this plant using headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS). The major compounds included 1, 8-cineole (43.5%), p-cymene (14.7%), humulene (5.5%), camphor (5.3%), linalool (4.7%), (E)-methyl cinnamate (3.8%), gamma-cadinene (3.3%), humulene oxide II (2.1%) and a-terpineol (1.5%). The majority of the volatiles were terpenoids of which oxygenated monoterpenes were the most abundant, accounting for 57.2% of the total volatiles. Alcohols made up the largest (52.8%) and aldehydes the smallest (0.2%) portions of the volatiles. Many bioactive compounds were present in the volatiles.

Antifungal and phytotoxic activity of essential oil from root of Senecio amplexicaulis Kunth. (Asteraceae) growing wild in high altitude-Himalayan region.

PubMed

Singh, Rajendra; Ahluwalia, Vivek; Singh, Pratap; Kumar, Naresh; Prakash Sati, Om; Sati, Nitin

2016-08-01

This work was aimed to evaluate the essential oil from root of medicinally important plant Senecio amplexicaulis for chemical composition, antifungal and phytotoxic activity. The chemical composition analysed by GC/GC-MS showed the presence of monoterpene hydrocarbons in high percentage with marker compounds as α-phellandrene (48.57%), o-cymene (16.80%) and β-ocimene (7.61%). The essential oil exhibited significant antifungal activity against five phytopathogenic fungi, Sclerotium rolfsii, Macrophomina phaseolina, Rhizoctonia solani, Pythium debaryanum and Fusarium oxysporum. The oil demonstrated remarkable phytotoxic activity in tested concentration and significant reduction in seed germination percentage of Phalaris minor and Triticum aestivum at higher concentrations. The roots essential oil showed high yield for one of its marker compound (α-phellandrene) which makes it important natural source of this compound.

Influence of Phenological Stages on Yield and Quality of Oregano (Origanum vulgare L.) Under the Agroclimatic Condition of Doon Valley (Uttarakhand)

PubMed Central

Chauhan, N. K.; Singh, S.; Haider, S. Z.; Lohani, H.

2013-01-01

A field experiment was conducted under the agroclimatic conditions of Doon valley, in order to determine the effects of phenological stages on herbage yield and quality of oil in oregano (Origanum vulgare L.). Plants were harvested in five phenological stages, i.e. early vegetative, late vegetative, flower initiation, full bloom, and fruit set stages. Results showed the significant effects of phenological stages on herbage, yield, and quality of oregano. Harvesting at full bloom stage showed better results in terms of herbage and oil yield. The quality of essential oil was evaluated using GC and GC/MS. Thymol content was rich in all the stages (46.90-62.26%) followed by γ-terpinene (1.11-11.75%) and p-cymene (3.11-5.32%). PMID:24302806

Oxidation of Alkyl-substituted Cyclic Hydrocarbons by a Nocardia during Growth on n-Alkanes

PubMed Central

Davis, J. B.; Raymond, R. L.

1961-01-01

Nocardia 107-332, a soil isolate, oxidizes short-chain alkyl-substituted cyclic hydrocarbons to cyclic acids while growing on n-alkanes. Cyclic acids are produced also from relatively long-chain alkyl-substituted cyclics such as n-nonylbenzene or n-dodecylbenzene which alone support growth in a mineral-salts medium. ω-Oxidation of the alkyl substituents is followed by β-oxidation. It is of particular interest that cyclic acids such as cyclohexaneacetic and phenylacetic with C2 residual carboxylic acid substituents are resistant to further oxidation by the nocardia but cyclic acids with C1 or C3 substituents are readily oxidized and utilized for growth. The specificity of microbial oxidations is demonstrated by the conversion of p-isopropyltoluene (p-cymene) to p-isopropylbenzoic acid in n-alkane, growth-supported nocardia cultures. PMID:13720182

Diastereoselective formation of metallamacrocyclic (arene)Ru(II) and CpRh(III) complexes.

PubMed

Lehaire, Marie-Line; Scopelliti, Rosario; Herdeis, Lorenz; Polborn, Kurt; Mayer, Peter; Severin, Kay

2004-03-08

The reaction of [(arene)RuCl(2)](2) (arene = cymene, 1,3,5-C(6)H(3)Me(3)) and [CpRhCl(2)](2) half-sandwich complexes with tridentate heterocyclic ligands in the presence of base has been investigated. In all cases, the chloro-ligands were substituted to give metallacyclic products with ring sizes between 4 and 18 atoms. The cyclization occurs in a highly diastereoselective fashion with chiral recognition between the different metal fragments. The complexes were comprehensively characterized by elemental analysis, NMR spectroscopy, and single crystal X-ray crystallography. For 2-hydroxy-nicotinic acid and 2-amino-nicotinic acid, dinuclear structures were obtained (15-17) whereas for 2,3-dihydroxyquinoline, 2,3-dihydroxyquinoxaline, and 6-methyl-2,3-phenazinediol, trimeric assemblies were found (19-22), and for 4-imidazolecarboxylic acid, a tetrameric assembly (18) was found.

Effect of chitosan-lemon essential oil coatings on volatile profile of strawberries during storage.

PubMed

Perdones, Ángela; Escriche, Isabel; Chiralt, Amparo; Vargas, Maria

2016-04-15

Chitosan coatings containing lemon essential oils were described as effective at controlling fruit fungal decay at 20°C during 7 days. In this work, GC-MS was used to characterise the volatile compounds of strawberries during cold storage in order to analyse the influence of fruit coatings with chitosan, containing or not containing lemon essential oil, on the volatile profile of the fruits. The coatings affected the metabolic pathways and volatile profile of the fruits. Pure chitosan promoted the formation of esters and dimethyl furfural in very short time after coating, while coatings containing lemon essential oil incorporated terpenes (limonene, γ-terpinene, p-cymene and α-citral) to the fruit volatiles and enhanced the fermentative process, modifying the typical fruit aroma composition. No effect of chitosan coatings was sensorially perceived, the changes induced by lemon essential oil were notably appreciated. Copyright © 2015 Elsevier Ltd. All rights reserved.

Antimicrobial activity of the essential oil obtained from roots and chemical composition of the volatile constituents from the roots, stems, and leaves of Ballota nigra from Serbia.

PubMed

Vukovic, Nenad; Sukdolak, Slobodan; Solujic, Slavica; Niciforovic, Neda

2009-04-01

The chemical composition of essential oils obtained from the roots, stems, and leaves of Ballota nigra, growing in Serbia, was investigated by gas chromatography/mass spectrometry analyses. Kovats indices, mass spectra, and standard compounds were used to identify a total of 115 individual compounds. The plant produces two types of essential oils. Oils derived from stems and leaves were sesquiterpene rich (78.17% and 88.40%, respectively), containing principally beta-caryophyllene, germacrene D, and alpha-humulene, present in appreciable amounts. In contrast, oil derived from the root was dominated by p-vinylguiacol (9.24%), borneol (7.51%), myrtenol (7.13%), trans-pinocarveol (5.22%), pinocarvone (4.37%), 2-methyl-3-phenylpropanal (4.32%), and p-cymen-8-ol (4.30%). Essential oil obtained from the roots was evaluated for the antimicrobial activity against seven bacterial species and one fungi.

Essential oil from the leaves of Annona vepretorum: chemical composition and bioactivity.

PubMed

Costa, Emmanoel Vilaça; Dutra, Lívia Macedo; Nogueira, Paulo Cesar de Lima; Moraes, Valéria Regina de Souza; Salvador, Marcos José; Ribeiro, Luis Henrique Gonzaga; Gadelha, Fernanda Ramos

2012-02-01

The essential oil from the leaves of Annona vepretorun was obtained by hydrodistillation using a Clevenger-type apparatus and analyzed by GC-MS and GC-FID. Eighteen compounds representing 98.1% of the crude essential oil were identified. The major compounds identified were bicyclogermacrene (43.7%), spathulenol (11.4%), alpha-felandrene (10.0%), alpha-pinene (7.1%), (E)-beta-ocimene (6.8%), germacrene D (5.8%), and p-cymene (4.2%). The trypanocidal activity against Trypanosoma cruzi epimastigote forms, as well as, the antimicrobial and antioxidant proprieties was investigated. The essential oil showed a potent trypanocidal activity with IC50 value of 31.9 +/-1.3 microg x mL(-1). For antimicrobial activity, the best result was observed against Candida tropicalis with a MIC value of 100 microg x mL(-1). For antioxidant capacity the essential oil showed weak activity.

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.

Effect of phosphorus concentration of the nutrient solution on the volatile constituents of leaves and bracts of Origanum dictamnus.

PubMed

Economakis, C; Skaltsa, Helen; Demetzos, Costas; Soković, M; Thanos, Costas A

2002-10-23

The chemical composition of the essential oils obtained from the leaves and bracts of hydroponically cultivated Origanum dictamnus were analyzed by GC-MS techniques. Three different concentrations of phosphorus (5, 30, and 60 mg/L) in the nutrient solution were used for the cultivation, using the nutrient film technique (NFT). A total of 46 different compounds were identified and significant differences (qualitative and quantitative) were observed between the samples. Carvacrol and p-cymene were identified as the main compounds in all samples analyzed, whereas thymoquinone was found in higher percentage in the leaves than in bracts. The essential oils were tested for their antibacterial activity against Gram-positive and Gram-negative bacteria. The oils obtained from the bracts were found to be more active. The results obtained from GC-MS analyses were submitted to chemometric analysis.

A detailed study of the volatile components of Plectranthus asirensis of Saudi Arabian origin.

PubMed

Al-Saleem, Muneera S M; Khan, Merajuddin; Alkhathlan, Hamad Z

2016-10-01

Essential oil composition of Plectranthus asirensis grown in Saudi Arabia was chemically analysed for the first time by various gas chromatography techniques (GC-MS, GC-FID, Co-GC, LRI determination and database and literature searches) using two different stationary phase columns (polar and nonpolar). This analysis led to the characterisation of a total of 124 components representing 98.5% of the total oil composition. The results revealed that P. asirensis oil was mainly dominated by monoterpenoids (90.7%) in which most representative constituents were thymol (66.0 ± 0.36%), γ-terpinene (14.0 ± 0.18%), p-cymene (5.2 ± 0.06%) and β-caryophyllene (3.0 ± 0.03%). It is worth mentioning here that this is the first report on the phytochemical constituents of P. asirensis.

Fumigant and repellent activities of essential oil extracted from Artemisia dubia and its main compounds against two stored product pests.

PubMed

Liang, Jun-Yu; Guo, Shan-Shan; Zhang, Wen-Juan; Geng, Zhu-Feng; Deng, Zhi-Wei; Du, Shu-Shan; Zhang, Ji

2018-05-01

The major chemical constituents of the essential oil extracted from Artemisia dubia wall. ex Bess. (Family: Asteraceae) were found as terpinolene (19.02%), limonene (17.40%), 2,5-etheno[4.2.2]propella-3,7,9-triene (11.29%), isoelemicin (11.05%) and p-cymene-8-ol (5.93%). Terpinolene and limonene were separated as main components from the essential oil. The essential oil showed fumigant toxicity against Tribolium castaneum and Liposcelis bostrychophila with LC 50 values of 49.54 and 0.74 mg/L, respectively. The essential oil and isolated compounds of A. dubia showed repellency activities against both insects. Terpinolene and limonene showed the fumigant toxicity against T. castaneum. Terpinolene showed obvious fumigant toxicity against L. bostrychophila. The results indicated that the essential oil of A. dubia had potential to be developed into natural insecticides for controlling stored product pests.

The synthesis, lipophilicity and cytotoxic effects of new ruthenium(II) arene complexes with chromone derivatives.

PubMed

Pastuszko, Adam; Majchrzak, Kinga; Czyz, Malgorzata; Kupcewicz, Bogumiła; Budzisz, Elzbieta

2016-06-01

A series of arene ruthenium(II) complexes with the general formula [(η(6)-arene)Ru(L)X2] (where arene=p-cymene, benzene, hexamethylbenzene or mesitylene, L=aminoflavone or aminochromone derivatives and X=Cl, I) were synthesized and characterized by elemental analysis, MS, IR and (1)H NMR spectroscopy. The stability of the selected complexes was assessed by UV-Vis spectroscopy in 24-hour period. The lipophilicity of the synthesized complexes was determined by the shake-flask method, and their cytotoxicity evaluated in vitro on patient-derived melanoma populations. The most active complexes against melanoma cells contain 7-aminoflavone and 6-aminoflavone as a ligand. The relationship between the cytotoxicity of all the obtained compounds and their logP values was determined and briefly analyzed with two different patterns observed. Copyright © 2016 Elsevier Inc. All rights reserved.

Self-Assembly of New Arene-Ruthenium Rectangles Containing Triptycene Building Block and Their Application in Fluorescent Detection of Nitro Aromatics

PubMed Central

Dubey, Abhishek; Mishra, Anurag; Min, Jin Wook; Lee, Min Hyung; Kim, Hyunuk; Stang, Peter J.; Chi, Ki-Whan

2014-01-01

A suite of two new tetraruthenium metallarectangles 5 and 6 have been obtained from [2 + 2] self-assemblies between dipyridylethynyltriptycene 2 and one of the two dinuclear arene ruthenium clips, [Ru2 (μ-η4-OO∩OO) (η6-p-cymene)2][OTf]2 ; (OO∩OO = oxalate 3; 6,11-dihydroxy-5,12-naphthacenedionato (dotq) 4; OTf = triflate). These molecular rectangles are fully characterized by 1H NMR spectroscopy, electrospray mass spectrometry. A single crystal of 6 was suitable for X-ray diffraction structural characterization. These new metallarectangles showed fluorescence behavior in solution, have been examined for emission quenching effects with various aromatic compounds, and show high quenching selectivity and sensitivity towards nitroaromatics, particularly picric acid and trinitrotoluene. Excited-state charge transfer from the rectangles to nitro aromatic substrates can be used to develop selective fluorescent sensors for nitro aromatics. PMID:26321767

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.

Comparison of different real time VOC measurement techniques in a ponderosa pine forest

NASA Astrophysics Data System (ADS)

Kaser, L.; Karl, T.; Schnitzhofer, R.; Graus, M.; Herdlinger-Blatt, I. S.; DiGangi, J. P.; Sive, B.; Turnipseed, A.; Hornbrook, R. S.; Zheng, W.; Flocke, F. M.; Guenther, A.; Keutsch, F. N.; Apel, E.; Hansel, A.

2013-03-01

Volatile organic compound (VOC) mixing ratios measured by five independent instruments are compared at a forested site dominated by ponderosa pine (Pinus Ponderosa) during the BEACHON-ROCS field study in summer 2010. The instruments included a Proton Transfer Reaction Time of Flight Mass Spectrometer (PTR-TOF-MS), a Proton Transfer Reaction Quadrupole Mass Spectrometer (PTR-MS), a Fast Online Gas-Chromatograph coupled to a Mass Spectrometer (GC/MS; TOGA), a Thermal Dissociation Chemical Ionization Mass Spectrometer (PAN-CIMS) and a Fiber Laser-Induced Fluorescence Instrument (FILIF). The species discussed in this comparison include the most important biogenic VOCs and a selected suite of oxygenated VOCs that are thought to dominate the VOC reactivity at this particular site as well as typical anthropogenic VOCs that showed low mixing ratios at this site. Good agreement was observed for methanol, the sum of the oxygenated hemiterpene 2-methyl-3-buten-2-ol (MBO) and the hemiterpene isoprene, acetaldehyde, the sum of acetone and propanal, benzene and the sum of methyl ethyl ketone (MEK) and butanal. Measurements of the above VOCs conducted by different instruments agree within 20%. The ability to differentiate the presence of toluene and cymene by PTR-TOF-MS is tested based on a comparison with GC-MS measurements, suggesting a study-average relative contribution of 74% for toluene and 26% for cymene. Similarly, 2-hydroxy-2-methylpropanal (HMPR) is found to interfere with the sum of methyl vinyl ketone and methacrolein (MVK + MAC) using PTR-(TOF)-MS at this site. A study-average relative contribution of 85% for MVK + MAC and 15% for HMPR was determined. The sum of monoterpenes measured by PTR-MS and PTR-TOF-MS was generally 20-25% higher than the sum of speciated monoterpenes measured by TOGA, which included α-pinene, β-pinene, camphene, carene, myrcene, limonene, cineole as well as other terpenes. However, this difference is consistent throughout the study, and likely points to an offset in calibration, rather than a difference in the ability to measure the sum of terpenes. The contribution of isoprene relative to MBO inferred from PTR-MS and PTR-TOF-MS was smaller than 12% while GC-MS data suggested an average of 21% of isoprene relative to MBO. This comparison demonstrates that the current capability of VOC measurements to account for OH reactivity associated with the measured VOCs is within 20%.

Comparison of different real time VOC measurement techniques in a ponderosa pine forest

NASA Astrophysics Data System (ADS)

Kaser, L.; Karl, T.; Schnitzhofer, R.; Graus, M.; Herdlinger-Blatt, I. S.; DiGangi, J. P.; Sive, B.; Turnipseed, A.; Hornbrook, R. S.; Zheng, W.; Flocke, F. M.; Guenther, A.; Keutsch, F. N.; Apel, E.; Hansel, A.

2012-10-01

Volatile organic compound (VOC) mixing ratios measured by five independent instruments are compared at a forested site dominated by ponderosa pine (Pinus Ponderosa) during the BEACHON-ROCS field study in summer 2010. The instruments included a Proton Transfer Reaction Time of Flight Mass Spectrometer (PTR-TOF-MS), a Proton Transfer Reaction Quadrupole Mass Spectrometer (PTR-MS), a Fast Online Gas-Chromatograph coupled to a Mass Spectrometer (GC/MS; TOGA), a Thermal Dissociation Chemical Ionization Mass Spectrometer (PAN-CIMS) and a Fiber Laser-Induced Fluorescence Instrument (FILIF). The species discussed in this comparison include the most important biogenic VOCs and a selected suite of oxygenated VOCs that are thought to dominate the VOC reactivity at this particular site as well as typical anthropogenic VOCs that showed low mixing ratios at this site. Good agreement was observed for methanol, the sum of the oxygenated hemiterpene 2-methyl-3-buten-2-ol (MBO) and the hemiterpene isoprene, acetaldehyde, the sum of acetone and propanal, benzene and the sum of methyl ethyl ketone (MEK) and butanal. Measurements of the above VOCs conducted by different instruments agree within 20%. The ability to differentiate the presence of toluene and cymene by PTR-TOF-MS is tested based on a comparison with GC-MS measurements, suggesting a study-average relative contribution of 74% for toluene and 26% for cymene. Similarly, 2-hydroxy-2-methylpropanal (HMPR) is found to interfere with the sum of methyl vinyl ketone and methacrolein (MVK+MAC) using PTR-(TOF)-MS at this site. A study-average relative contribution of 85% for MVK+MAC and 15% for HMPR was determined. The sum of monoterpenes measured by PTR-MS and PTR-TOF-MS was generally 20-25% higher than the sum of speciated monoterpenes measured by TOGA, which included α-pinene, β-pinene, camphene, carene, myrcene, limonene, cineole as well as other terpenes. However, this difference is consistent throughout the study, and likely points to an offset in calibration, rather than a difference in the ability to measure the sum of terpenes. The contribution of isoprene relative to MBO inferred from PTR-MS and PTR-TOF-MS was smaller than 12% while GC-MS data suggested an average of 21% of isoprene relative to MBO. This comparison demonstrates that the current capability of VOC measurements to account for OH reactivity associated with the measured VOCs is within 20%.

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.

The effect of microbial degradation on the chromatographic profiles of tiki torch fuel, lamp oil, and turpentine.

PubMed

Turner, Dee A; Goodpaster, John V

2011-07-01

Biodegradation can result in selective removal of many of the compounds required for the identification of an ignitable liquid. In this study, the effects of microbial degradation on tiki torch fuel, lamp oil, and turpentine are reported. Samples of soil spiked with 20 μL of the liquids were stored at room temperature for up to 7 days. The ignitable liquids were then recovered using passive headspace concentration onto charcoal strips followed by solvent elution using pentane. Microbial degradation of tiki torch fuel resulted in the loss of the n-alkanes relative to the branched alkanes. Changes in the profile of the lamp oil were minor due to the highly branched nature of its alkanes. Microbial degradation of turpentine resulted in the selective loss of limonene and o-cymene. Overall, significant degradation by microbial action could result in the inability to identify the presence of an ignitable liquid or misclassify the ignitable liquid found. © 2011 American Academy of Forensic Sciences.

GC-MS characterisation and antibacterial activity evaluation of Nigella sativa oil against diverse strains of Salmonella.

PubMed

Sarwar, Arslan; Latif, Zakia

2015-01-01

Salmonella resistance is becoming a worldwide serious health issue in these days; therefore, it is an urgent need to develop some alternative approaches to overcome this problem. Twenty bacterial strains were isolated and purified from different environmental sources and confirmed as Salmonella by morphological and biochemical analyses. Further confirmation was done by 16s rRNA sequencing. Antibiotic susceptibility test was performed by well diffusion assay against different concentrations of Ceftriaxone and Ciprofloxacin. The behaviour of both antibiotics was different against diverse strains of Salmonella. Salmonella strains resistant to both antibiotics were analysed for antibacterial activity of natural extracts of Nigella sativa (black seeds). N. sativa oil was found to be more effective against Salmonella species for which even Ceftriaxone and Ciprofloxacin were ineffective. Gas chromatography and mass spectrometry analysis of N. sativa oil was also accomplished, exhibiting 10 compounds including thymoquinone, p-cymene, cis-carveol, thymol, α-phellandrene, α-pinene, β-pinene, trans-anethole, α-longipinene and longifolene.

Plants of the Melaleuca Genus as Antimicrobial Agents: From Farm to Pharmacy.

PubMed

Sharifi-Rad, Javad; Salehi, Bahare; Varoni, Elena Maria; Sharopov, Farukh; Yousaf, Zubaida; Ayatollahi, Seyed Abdulmajid; Kobarfard, Farzad; Sharifi-Rad, Mehdi; Afdjei, Mohammad Hossain; Sharifi-Rad, Majid; Iriti, Marcello

2017-10-01

Plants belonging to Melaleuca genus (Myrtaceae family) are native to Oceania, where they have been used for ages by Aborigine people in Australian traditional medicine, mainly because of their broad-spectrum antimicrobial activity. Although, M. linariifolia, M. dissitiflora, and other species of Melaleuca can also be used, the tea tree oil, an essential oil obtained from M. alternifolia shows the longest history of medicinal uses. Tea tree oil contains for the 80-90% several monoterpenes (terpinen-4-ol, α-terpinene, 1,8-cineol, p-cymene, α-terpineol, α-pinene, terpinolene, limonene, and sabinene). Sesquiterpenes and aromatic compounds further compose this oil. The essential oil of Melaleuca spp. has been reported to possess effective antibacterial and antifungal properties in vitro. In particular, data show that 1,8-cineol, terpinen-4-ol and methyl eugenol play the key role in mediating this oil's antimicrobial activity. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

GC-FID coupled with chemometrics for quantitative and chemical fingerprinting analysis of Alpinia oxyphylla oil.

PubMed

Miao, Qing; Kong, Weijun; Zhao, Xiangsheng; Yang, Shihai; Yang, Meihua

2015-01-01

Analytical methods for quantitative analysis and chemical fingerprinting of volatile oils from Alpinia oxyphylla were established. The volatile oils were prepared by hydrodistillation, and the yields were between 0.82% and 1.33%. The developed gas chromatography-flame ionization detection (GC-FID) method showed good specificity, linearity, reproducibility, stability and recovery, and could be used satisfactorily for quantitative analysis. The results showed that the volatile oils contained 2.31-77.30 μL/mL p-cymene and 12.38-99.34 mg/mL nootkatone. A GC-FID fingerprinting method was established, and the profiles were analyzed using chemometrics. GC-MS was used to identify the principal compounds in the GC-FID profiles. The profiles of almost all the samples were consistent and stable. The harvesting time and source were major factors that affected the profile, while the volatile oil yield and the nootkatone content had minor secondary effects. Copyright © 2014 Elsevier B.V. All rights reserved.

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.

The chemical composition, antimicrobial, and antioxidant activities of Pycnocycla spinosa and Pycnocyla flabellifolia essential oils.

PubMed

Mahboubi, Mohaddese; Mahdizadeh, Elaheh; Heidary Tabar, Rezvan

2016-11-01

The purpose of our study was to compare the chemical compositions and antimicrobial and antioxidant activities of Pycnocycla spinosa and Pycnocycla flabellifolia essential oils. cis-Asarone (62.5%) and widdra-2,4(14)-diene (9%) were the main components of P. spinosa aerial part essential oil, while elemicin (60.1%) and caryophyllene oxide (9.8%) were the main components of P. spinosa seed essential oil. α-Phellandrene (25.5%), p-cymene (15.3%), and limonene (13.3%) were found in P. flabellifolia essential oil. The inhibition zone diameters for P. flabellifolia essential oil were significantly higher than for the two other essential oils from P. spinosa (p<0.05). In broth dilution assay (µL/mL), the sensitive microorganism to Pycnocycla sp. (P. spinosa, P. flabellifolia) was Aspergillus niger, followed by Candida albicans. In 2,2-diphenyl-1-picrylhydrazyl (DPPH) system, P. spinosa aerial parts essential oil (IC50=548 µg/mL) had higher antioxidant activity than that of two other essential oils.

Comparative investigation of Umbellularia californica and Laurus nobilis leaf essential oils and identification of constituents active against Aedes aegypti.

PubMed

Tabanca, Nurhayat; Avonto, Cristina; Wang, Mei; Parcher, Jon F; Ali, Abbas; Demirci, Betul; Raman, Vijayasankar; Khan, Ikhlas A

2013-12-18

Umbellularia californica (California bay laurel) and Laurus nobilis (Mediterranean bay laurel) leaves may be mistaken or used as a substitute on the market due to their morphological similarity. In this study, a comparison of anatomical and chemical features and biological activity of both plants is presented. L. nobilis essential oil biting deterrent and larvicidal activity were negligible. On the other hand, U. californica leaf oil showed biting deterrent activity against Aedes aegypti . The identified active repellents was thymol, along with (-)-umbellulone, 1,8-cineole, and (-)-α-terpineol. U. californica essential oil also demonstrated good larvicidal activity against 1-day-old Ae. aegypti larvae with a LD50 value of 52.6 ppm. Thymol (LD50 = 17.6 ppm), p-cymene, (-)-umbellulone, and methyleugenol were the primary larvicidal in this oil. Umbellulone was found as the principal compound (37%) of U. californica essential oil, but was not present in L. nobilis essential oil. Umbellulone mosquito activity is here reported for the first time.

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.

Screening of the constituents, antimicrobial and antioxidant activity of endemic Origanum hypericifolium O. Schwartz & P.H. Davis.

PubMed

Celik, Ali; Nur Herken, E; Arslan, Idris; Zafer Ozel, M; Mercan, Nazime

2010-10-01

The chemical compositions, total phenol content, antioxidant and antimicrobial activities with oxidant status of the essential oil from an endemic Turkish species, Origanum hypericifolium, were investigated. Steam distillation (SD) was used to isolate the essential oils, and the chemical analyses were performed by gas chromatography-mass spectrometry (GC-MS). The antimicrobial activity was tested by agar disc diffusion method against Morganella morganii (clinic isolate), Micrococcus flavus (clinic isolate), Micrococcus luteus NRLL B-4375, Proteus vulgaris RSKK 96026, Escherichia coli ATCC 11230, Escherichia coli ATCC 25922, Yersinia enterecolitica RSKK 1501, Staphylococcus aureus ATCC 25923, S. aureus ATCC 25933, S. aureus ATCC 12598, S. aureus (clinic isolate), MRSA 1 (clinic isolate), MRSA 2 (clinic isolate), MRSA 3 (clinic isolate) and MRSA 4 (clinic isolate). The major compounds found in volatiles of O. hypericifolium were p-cymene, carvacrol and γ-terpinene. Results showed that O. hypericifolium has the potential for being used in food and medicine because of its antioxidant and antibacterial activity.

Control of stored grain pest, Callosobruchus maculatus (F.) (Coleoptera: Bruchidae) using the essential oil isolated from Plectranthus zeylanicus.

PubMed

Balachandra, B A H E; Pathirathna, P U; Paranagama, P A

2012-01-01

The bruchid, Callosobruchus maculatus (F.) causes major losses during the storage of cowpea seeds [Vigna unguiculata (L.)Walp.] in Sri Lanka. Essential oil isolated from Plectranthus zeylanicus plant was tested for potential insecticidal activity against C. maculatus. The gas chromatography studies of the essential oil of P. zeylanicus showed that ρ-cymene (3.5%), β-caryophyllene (0.2%), geranyl acetate (9.3%) and geraniol (7.2%) were the major constituents. The adults of C. maculatus were susceptible to both fumigant and contact toxicity of P. zeylanicus plant oil. LC(50) values of 0.927 and 0.010 g L(-1) were obtained for fumigant toxicity and contact toxicity assays, respectively. Oviposition and F(1) adult emergence were significantly inhibited by P. zeylanicus plant oil at a concentration higher than 0.001 g L(-1) in both fumigant and contact toxicities. The analysis of olfactometer and choice camber bioassays revealed the repellent effects of the oil of P. zeylanicus plant.

Comparative study of the chemical profiling, antioxidant and antimicrobial activities of essential oils of different parts of Thymus willdenowii Boiss & Reut.

PubMed

Ouknin, Mohamed; Romane, Abderrahmane; Costa, Jean; Majidi, Lhou

2018-02-27

The analysis of Thymus willdenowii Boiss & Reut essential oils (TW EOs) shows 33 components accounting for (96.3-97.7%) of all identified. The main constituents of TW EOs were thymol (35.5-47.3%), p-cymene (13.9-23.8%), γ-terpinene (8.9-20.3%). The antioxidant assays revealed that all TW EOs tested showed strong activities, the antimicrobial effect of TW EOs has been tested against isolated clinical strains of Proteus mirabilis (ATCC 35659), Escherichia coli (ATCC 25922), Candida albicans (ATCC 10231), Bacillus cereus (ATCC 10876), and Aspergillus brasilliensis (ATCC 16404). The antimicrobial test indicates that TW EOs show an inhibition effect against all the tested bacteria with a MIC of 6.9 to 27.6 μg/mL -1 . These results proving that the essential oils extracted from Thymus willdenowii Boiss & Reut may be a new potential source of natural antimicrobial applied in pharmaceutical and food industries.

Impact of blanching, sweating and drying operations on pungency, aroma and color of Piper borbonense.

PubMed

Weil, M; Shum Cheong Sing, A; Méot, J M; Boulanger, R; Bohuon, P

2017-03-15

Low pungency, high aromatic potential and red color, give to Piper borbonense its originality when compared to Piper nigrum. Effects of blanching, sweating and drying on these characteristics were assessed. The three operations had no impact on the concentration of piperine and essential oil but affected the composition of essential oil slightly and considerably affected the color of the pepper. The "wet process", including blanching, sweating and drying, had the largest impact on the composition of aroma, increasing para-cymene content by 89% and reducing safrole content by 33% in dried pepper compared to fresh. Blanching increased the drying rate thus reducing drying time. Drying had a major impact on color, which changed from red to brown. The biggest differences observed led to reductions of 2.2, 7.9 and 8.4units in L ∗ , a ∗ and b ∗ values, when chromatic values measured in fresh pepper were compared to those of dried pepper. Copyright © 2016 Elsevier Ltd. All rights reserved.

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.

Evolutionary Engineering Improves Tolerance for Replacement Jet Fuels in Saccharomyces cerevisiae

PubMed Central

Brennan, Timothy C. R.; Williams, Thomas C.; Schulz, Benjamin L.; Palfreyman, Robin W.; Nielsen, Lars K.

2015-01-01

Monoterpenes are liquid hydrocarbons with applications ranging from flavor and fragrance to replacement jet fuel. Their toxicity, however, presents a major challenge for microbial synthesis. Here we evolved limonene-tolerant Saccharomyces cerevisiae strains and sequenced six strains across the 200-generation evolutionary time course. Mutations were found in the tricalbin proteins Tcb2p and Tcb3p. Genomic reconstruction in the parent strain showed that truncation of a single protein (tTcb3p1-989), but not its complete deletion, was sufficient to recover the evolved phenotype improving limonene fitness 9-fold. tTcb3p1-989 increased tolerance toward two other monoterpenes (β-pinene and myrcene) 11- and 8-fold, respectively, and tolerance toward the biojet fuel blend AMJ-700t (10% cymene, 50% limonene, 40% farnesene) 4-fold. tTcb3p1-989 is the first example of successful engineering of phase tolerance and creates opportunities for production of the highly toxic C10 alkenes in yeast. PMID:25746998

Composition of essential oils in subterranean organs of three species of Valeriana L.

PubMed

Samaneh, Ekhteraei Tousi; Tayebeh, Radjabian; Hassan, Ebrahimzadeh; Vahid, Niknam

2010-11-01

Essential oils from the subterranean organs of three species of Valeriana L. from Iran (Valeriana sisymbriifolia Vahl, Valeriana alliariifolia Adams and Valeriana officinalis L.) belonging to Valerianaceae family have been obtained by hydrodistillation and analysed by gas chromatography-mass spectrometry in order to discern the differences and similarities between the volatile chemical compositions of these species. More than 100 components were identified in essential oils of the studied plants (Supplementary Table S1--online only). The principal common constituents of the three species of Valeriana were spathulenol, limonene, γ-terpinene, vulgarone B and p-cymene. The main essential oil ingredients were α-selinene (7.83%) in V. sisymbriifolia, limonene (3.53%) in V. alliariifolia and spathulenol (13.33%), α-campholenal (11.48%), vulgarone B (8.38%) and valerenal (8.32%) in V. officinalis plants. Ageratochromene (precocene II), a chromene substance with antibacterial, antifungal, insecticidal and antijuvenile hormonal activities, was found at high levels (35.59% and 36.58%) in the essential oils of V. sisymbriifolia plants.

Floral scent compounds of Amazonian Annonaceae species pollinated by small beetles and thrips.

PubMed

Jürgens, A; Webber, A C; Gottsberger, G

2000-11-01

Chemical analysis (GC-MS) yielded a total of 58 volatile compounds in the floral scents of six species of Annonaceae distributed in four genera (Xylopia, Anaxagorea, Duguetia, and Rollinia), Xylopia aromatica is pollinated principally by Thysanoptera and secondarily by small beetles (Nitidulidae and Staphylinidae), whereas the five other species were pollinated by Nitidulidae and Staphylinidae only. Although the six Annonaceae species attract a similar array of pollinator groups, the major constituents of their floral scents are of different biochemical origin. The fragrances of flowers of Anaxagorea brevipes and Anaxagorea dolichocarpa were dominated by esters of aliphatic acids (ethyl 2-methylbutanoate, ethyl 3-methylbutanoate), which were not detected in the other species. Monoterpenes (limonene, p-cymene, alpha-pinene) were the main scent compounds of Duguetia asterotricha, and naphthalene prevailed in the scent of Rollinia insignis flowers. The odors of X. aromatica and Xylopia benthamii flowers were dominated by high amounts of benzenoids (methylbenzoate, 2-phenylethyl alcohol).

Chemical composition and antifungal activity of the essential oil of Origanum virens on Candida species.

PubMed

Salgueiro, L R; Cavaleiro, C; Pinto, E; Pina-Vaz, C; Rodrigues, A G; Palmeira, A; Tavares, C; Costa-de-Oliveira, S; Gonçalves, M J; Martinez-de-Oliveira, J

2003-09-01

The composition and the antifungal activity of the essential oil of Origanum virens on Candida species were studied. The essential oil was obtained from the aerial parts of the plant by hydrodistillation and analyzed by GC and GC-MS. The oil was characterized by its high content of carvacrol (68.1 %) and its biogenetic precursors, gamma-terpinene (9.9 %) and p-cymene (4.5 %). The minimal inhibitory concentration (MIC) and the minimal lethal concentration (MLC) were used to evaluate the antifungal activity against Candida strains (7 clinical isolates and 3 ATCC type strains). The inhibition of germ tube formation and flow cytometry, using the fluorescent probe propidium iodide (PI), were used to evaluate their mechanisms of action. MIC and MLC values were similar for most tested strains, ranging from 0.16 to 0.32 microL/mL. Concentrations lower than MIC values strongly prevent germ tube formation. The fungicidal effect is primarily due to an extensive lesion of the membrane.

GC-MS evaluation of Cymbopogon citratus (DC) Stapf oil obtained using modified hydrodistillation and microwave extraction methods.

PubMed

Ajayi, E O; Sadimenko, A P; Afolayan, A J

2016-10-15

Bioactive compounds of Cymbopogon citratus essential oil, using different media have been tentatively identified with the aid of gas chromatography-mass spectrometry (GC-MS). Hydrodistillation was complemented using weakly acidic and alkaline media for the oil extraction. Solvent-free microwave extraction (SFME) was also used. Analyses of the oils revealed the presence of 7, 16, 22, and 15 compounds in the water-distilled (WD), microwave-distilled (MD), acid-distilled (AD), and base-distilled (BD), essential oils, respectively. Total yield of the volatile fractions was 0.73%, 0.64%, 0.70%, and 0.45%, respectively. Citral was found to be the major component, the base extraction having the highest content. This was followed by 2-isopropenyl-5-methylhex-4-enal, p-cymene, and 2-thujene. The antimicrobial, antibacterial, and antioxidant activities and assessment of medicinal/nutritional uses of the essential oils are subjects of future studies. Copyright © 2016. Published by Elsevier Ltd.

Validation of models to estimate the fumigant and larvicidal activity of Eucalyptus essential oils against Aedes aegypti (Diptera: Culicidae).

PubMed

Lucia, Alejandro; Juan, Laura W; Zerba, Eduardo N; Harrand, Leonel; Marcó, Martín; Masuh, Hector M

2012-05-01

The aim of this work is to validate the pre-existing models that relate the larvicidal and adulticidal activities of the Eucalyptus essential oils on Aedes aegypti. Previous works at our laboratory described that the larvicidal activity of Eucalyptus essential oils can be estimated from the relative concentration of two main components (p-cymene and 1,8-cineole) and that the adulticidal effectiveness can be explained, to a great extent, by the presence of large amounts of the component 1,8-cineole in it. In general, the results show that the higher adulticidal effect of essential oils the lower their larvicidal activity. Fresh leaves was harvested and distilled. Once the essential oil was obtained, the chemical composition was analysed, evaluating the biological activity of 15 species of the genus Eucalyptus (Eucalyptus badjensis Beuzev and Welch, Eucalyptus badjensis × nitens, Eucalyptus benthamii var Benthamii Maiden and Cambage, Eucalyptus benthamii var dorrigoensis Maiden and Cambage, Eucalyptus botryoides Smith, Eucalyptus dalrympleana Maiden, Eucalyptus fastigata Deane and Maiden, Eucalyptus nobilis L.A.S. Johnson and K.D.Hill, Eucalyptus polybractea R. Baker, Eucalyptus radiata ssp radiata Sieber ex Spreng, Eucalyptus resinifera Smith, Eucalyptus robertsonii Blakely, Eucalyptus robusta Smith, Eucalyptus rubida Deane and Maiden, Eucalyptus smithii R. Baker). Essential oils of these plant species were used for the validation of equations from preexistent models, in which observed and estimated values of the biological activity were compared. The regression analysis showed a strong validation of the models, re-stating the trends previously observed. The models were expressed as follows: A, fumigant activity [KT(50(min)) = 10.65-0.076 × 1,8-cineole (%)](p < 0.01; F, 397; R (2), 0.79); B, larval mortality (%)((40 ppm)) = 103.85 + 0.482 × p-cymene (%) - 0.363 × α-pinene (%) - 1.07 × 1,8-cineole (%) (p < 0.01; F, 300; R (2), 0.90). These results confirmed the importance of the mayor components in the biological activity of Eucalyptus essential oils on A. aegypti. However, it is worth mentioning that two or three species differ in the data estimated by the models, and these biological activity results coincide with the presence of minor differential components in the essential oils. According to what was previously mentioned, it can be inferred that the model is able to estimate very closely the biological activity of essential oils of Eucalyptus on A. aegypti.

Indoor terpene emissions from cooking with herbs and pepper and their secondary organic aerosol production potential

PubMed Central

Klein, Felix; Farren, Naomi J.; Bozzetti, Carlo; Daellenbach, Kaspar R.; Kilic, Dogushan; Kumar, Nivedita K.; Pieber, Simone M.; Slowik, Jay G.; Tuthill, Rosemary N.; Hamilton, Jacqueline F.; Baltensperger, Urs; Prévôt, André S. H.; El Haddad, Imad

2016-01-01

Cooking is widely recognized as an important source of indoor and outdoor particle and volatile organic compound emissions with potential deleterious effects on human health. Nevertheless, cooking emissions remain poorly characterized. Here the effect of herbs and pepper on cooking emissions was investigated for the first time to the best of our knowledge using state of the art mass spectrometric analysis of particle and gas-phase composition. Further, the secondary organic aerosol production potential of the gas-phase emissions was determined by smog chamber aging experiments. The emissions of frying meat with herbs and pepper include large amounts of mono-, sesqui- and diterpenes as well as various terpenoids and p-cymene. The average total terpene emission rate from the use of herbs and pepper during cooking is estimated to be 46 ± 5 gg-1Herbs min-1. These compounds are highly reactive in the atmosphere and lead to significant amounts of secondary organic aerosol upon aging. In summary we demonstrate that cooking with condiments can constitute an important yet overlooked source of terpenes in indoor air. PMID:27830718

Stable isotope dilution assay (SIDA) and HS-SPME-GCMS quantification of key aroma volatiles for fruit and sap of Australian mango cultivars.

PubMed

San, Anh T; Joyce, Daryl C; Hofman, Peter J; Macnish, Andrew J; Webb, Richard I; Matovic, Nicolas J; Williams, Craig M; De Voss, James J; Wong, Siew H; Smyth, Heather E

2017-04-15

Reported herein is a high throughput method to quantify in a single analysis the key volatiles that contribute to the aroma of commercially significant mango cultivars grown in Australia. The method constitutes stable isotope dilution analysis (SIDA) in conjunction with headspace (HS) solid-phase microextraction (SPME) coupled with gas-chromatography mass spectrometry (GCMS). Deuterium labelled analogues of the target analytes were either purchased commercially or synthesised for use as internal standards. Seven volatiles, hexanal, 3-carene, α-terpinene, p-cymene, limonene, α-terpinolene and ethyl octanoate, were targeted. The resulting calibration functions had determination coefficients (R 2 ) ranging from 0.93775 to 0.99741. High recovery efficiencies for spiked mango samples were also achieved. The method was applied to identify the key aroma volatile compounds produced by 'Kensington Pride' and 'B74' mango fruit and by 'Honey Gold' mango sap. This method represents a marked improvement over current methods for detecting and measuring concentrations of mango fruit and sap volatiles. Copyright © 2016 Elsevier Ltd. All rights reserved.

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.

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.

Composition, antibacterial, antioxidant and antiproliferative activities of essential oils from three Origanum species growing wild in Lebanon and Greece.

PubMed

Marrelli, Mariangela; Conforti, Filomena; Formisano, Carmen; Rigano, Daniela; Arnold, Nelly Apostolides; Menichini, Francesco; Senatore, Felice

2016-01-01

The essential oils from Origanum dictamnus, Origanum libanoticum and Origanum microphyllum were analysed by GC-MS, finding carvacrol, p-cymene, linalool, γ-terpinene and terpinen-4-ol as major components. The antioxidant activity by the DPPH and FRAP tests and the antiproliferative activity against two human cancer cell lines, LoVo and HepG2, were investigated, showing that the essential oil of O. dictamnus was statistically the most inhibitory on both the cell lines, while all the oils exerted a weak antioxidant activity. Furthermore, the samples were tested against 10 Gram-negative and Gram-positive bacteria; all the oils were active on Gram-positive bacteria but O. dictamnus essential oil was the most effective (MIC = 25-50 μg/mL), showing also a good activity against the Gram-negative Escherichia coli (MIC = 50 μg/mL). Data suggest that these essential oils and particularly O. dictamnus oil could be used as valuable new flavours with functional properties for food or nutraceutical products.

Indoor terpene emissions from cooking with herbs and pepper and their secondary organic aerosol production potential

NASA Astrophysics Data System (ADS)

Klein, Felix; Farren, Naomi J.; Bozzetti, Carlo; Daellenbach, Kaspar R.; Kilic, Dogushan; Kumar, Nivedita K.; Pieber, Simone M.; Slowik, Jay G.; Tuthill, Rosemary N.; Hamilton, Jacqueline F.; Baltensperger, Urs; Prévôt, André S. H.; El Haddad, Imad

2016-11-01

Cooking is widely recognized as an important source of indoor and outdoor particle and volatile organic compound emissions with potential deleterious effects on human health. Nevertheless, cooking emissions remain poorly characterized. Here the effect of herbs and pepper on cooking emissions was investigated for the first time to the best of our knowledge using state of the art mass spectrometric analysis of particle and gas-phase composition. Further, the secondary organic aerosol production potential of the gas-phase emissions was determined by smog chamber aging experiments. The emissions of frying meat with herbs and pepper include large amounts of mono-, sesqui- and diterpenes as well as various terpenoids and p-cymene. The average total terpene emission rate from the use of herbs and pepper during cooking is estimated to be 46 ± 5 gg-1Herbs min-1. These compounds are highly reactive in the atmosphere and lead to significant amounts of secondary organic aerosol upon aging. In summary we demonstrate that cooking with condiments can constitute an important yet overlooked source of terpenes in indoor air.

Chemically engineered papain as artificial formate dehydrogenase for NAD(P)H regeneration.

PubMed

Haquette, Pierre; Talbi, Barisa; Barilleau, Laure; Madern, Nathalie; Fosse, Céline; Salmain, Michèle

2011-08-21

Organometallic complexes of the general formula [(η(6)-arene)Ru(N⁁N)Cl](+) and [(η(5)-Cp*)Rh(N⁁N)Cl](+) where N⁁N is a 2,2'-dipyridylamine (DPA) derivative carrying a thiol-targeted maleimide group, 2,2'-bispyridyl (bpy), 1,10-phenanthroline (phen) or ethylenediamine (en) and arene is benzene, 2-chloro-N-[2-(phenyl)ethyl]acetamide or p-cymene were identified as catalysts for the stereoselective reduction of the enzyme cofactors NAD(P)(+) into NAD(P)H with formate as a hydride donor. A thorough comparison of their effectiveness towards NAD(+) (expressed as TOF) revealed that the Rh(III) complexes were much more potent catalysts than the Ru(II) complexes. Within the Ru(II) complex series, both the N⁁N and arene ligands forming the coordination sphere had a noticeable influence on the activity of the complexes. Covalent anchoring of the maleimide-functionalized Ru(II) and Rh(III) complexes to the cysteine endoproteinase papain yielded hybrid metalloproteins, some of them displaying formate dehydrogenase activity with potentially interesting kinetic parameters.

Crystal structure of bis-[μ-(4-meth-oxy-phen-yl)methane-thiol-ato-κ(2) S:S]bis-[chlorido-(η(6)-1-isopropyl-4-methyl-benzene)-ruthenium(II)] chloro-form disolvate.

PubMed

Stíbal, David; Süss-Fink, Georg; Therrien, Bruno

2015-10-01

The mol-ecular structure of the title complex, [Ru2(C8H9OS)2Cl2(C10H14)2]·2CHCl3 or (p-MeC6H4Pr (i) )2Ru2(SCH2-p-C6H5-OCH3)2Cl2·2CHCl3, shows inversion symmetry. The two symmetry-related Ru(II) atoms are bridged by two 4-meth-oxy-α-toluene-thiol-ato [(4-meth-oxy-phen-yl)methane-thiol-ato] units. One chlorido ligand and the p-cymene ligand complete the typical piano-stool coordination environment of the Ru(II) atom. In the crystal, the CH moiety of the chloro-form mol-ecule inter-acts with the chlorido ligand of the dinuclear complex, while one Cl atom of the solvent inter-acts more weakly with the methyl group of the bridging 4-meth-oxy-α-toluene-thiol-ato unit. This assembly leads to the formation of supra-molecular chains extending parallel to [021].

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.

Response of Biomass Development, Essential Oil, and Composition of Plectranthus amboinicus (Lour.) Spreng. to Irrigation Frequency and Harvest Time.

PubMed

Sabra, Ali S; Astatkie, Tessema; Alataway, Abed; Mahmoud, Abeer A; Gendy, Ahmed S H; Said-Al Ahl, Hussein A H; Tkachenko, Kirill G

2018-03-01

A greenhouse experiment was conducted to study the effects of four irrigation intervals (4, 8, 12, and 16 days) and six harvests (2, 4, 6, 8, 10, and 12 months after transplanting) on biomass, essential oil content, and composition of Plectranthus amboinicus (Lour.) Spreng. Fresh weight and essential oil yield decreased with increasing irrigation interval; whereas, essential oil content was stimulated by water stress and increased as the irrigation interval increased. Fresh weight of Plectranthus amboinicus irrigated every 4 days peaked when harvested at 6 months, but essential oil content peaked when irrigated every 16 days and harvested at 2 months after transplantation. On the other hand, essential oil yield peaked when irrigated every 8 days and harvested at 6 months. Thymol, p-cymene, γ-terpinene, and β-caryophyllene were the major compounds, and they peaked at different irrigation intervals and harvest times. This study showed biomass, essential oil content, and yield as well as the major and minor constituents of Plectranthus amboinicus are influenced by irrigation interval and the timing of harvest. © 2018 Wiley-VHCA AG, Zurich, Switzerland.

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

Indoor terpene emissions from cooking with herbs and pepper and their secondary organic aerosol production potential.

PubMed

Klein, Felix; Farren, Naomi J; Bozzetti, Carlo; Daellenbach, Kaspar R; Kilic, Dogushan; Kumar, Nivedita K; Pieber, Simone M; Slowik, Jay G; Tuthill, Rosemary N; Hamilton, Jacqueline F; Baltensperger, Urs; Prévôt, André S H; El Haddad, Imad

2016-11-10

Cooking is widely recognized as an important source of indoor and outdoor particle and volatile organic compound emissions with potential deleterious effects on human health. Nevertheless, cooking emissions remain poorly characterized. Here the effect of herbs and pepper on cooking emissions was investigated for the first time to the best of our knowledge using state of the art mass spectrometric analysis of particle and gas-phase composition. Further, the secondary organic aerosol production potential of the gas-phase emissions was determined by smog chamber aging experiments. The emissions of frying meat with herbs and pepper include large amounts of mono-, sesqui- and diterpenes as well as various terpenoids and p-cymene. The average total terpene emission rate from the use of herbs and pepper during cooking is estimated to be 46 ± 5 gg -1 Herbs min -1 . These compounds are highly reactive in the atmosphere and lead to significant amounts of secondary organic aerosol upon aging. In summary we demonstrate that cooking with condiments can constitute an important yet overlooked source of terpenes in indoor air.

Probing hydrogen bond networks in half-sandwich Ru(II) building blocks by a combined 1H DQ CRAMPS solid-state NMR, XRPD, and DFT approach.

PubMed

Chierotti, Michele R; Gobetto, Roberto; Nervi, Carlo; Bacchi, Alessia; Pelagatti, Paolo; Colombo, Valentina; Sironi, Angelo

2014-01-06

The hydrogen bond network of three polymorphs (1α, 1β, and 1γ) and one solvate form (1·H2O) arising from the hydration-dehydration process of the Ru(II) complex [(p-cymene)Ru(κN-INA)Cl2] (where INA is isonicotinic acid), has been ascertained by means of one-dimensional (1D) and two-dimensional (2D) double quantum (1)H CRAMPS (Combined Rotation and Multiple Pulses Sequences) and (13)C CPMAS solid-state NMR experiments. The resolution improvement provided by homonuclear decoupling pulse sequences, with respect to fast MAS experiments, has been highlighted. The solid-state structure of 1γ has been fully characterized by combining X-ray powder diffraction (XRPD), solid-state NMR, and periodic plane-wave first-principles calculations. None of the forms show the expected supramolecular cyclic dimerization of the carboxylic functions of INA, because of the presence of Cl atoms as strong hydrogen bond (HB) acceptors. The hydration-dehydration process of the complex has been discussed in terms of structure and HB rearrangements.

Impacts of simulated herbivory on VOC emission profiles from coniferous plants

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

Faiola, C. L.; Jobson, B. T.; VanReken, T. M.

The largest global source of volatile organic compounds (VOCs) in the atmosphere is from biogenic emissions. Plant stressors associated with a changing environment can alter both the quantity and composition of the compounds that are emitted. This study investigated the effects of one global change stressor, increased herbivory, on plant emissions from five different coniferous species: bristlecone pine ( Pinus aristata), blue spruce ( Picea pungens), western redcedar ( Thuja plicata), grand fir ( Abies grandis), and Douglas-fir ( Pseudotsugas menziesii). Herbivory was simulated in the laboratory via exogenous application of methyl jasmonate, an herbivory proxy. Gas-phase species were measuredmore » continuously with a gas chromatograph coupled to a mass spectrometer and flame ionization detector (GC-MS-FID). Stress responses varied between the different plant types and even between experiments using the same set of saplings. The compounds most frequently impacted by the stress treatment were alpha-pinene, beta-pinene, 1,8-cineol, beta-myrcene, terpinolene, limonene, and the cymene isomers. Individual compounds within a single experiment often exhibited a different response to the treatment from one another.« less

Impacts of simulated herbivory on volatile organic compound emission profiles from coniferous plants

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

Faiola, C. L.; Jobson, B. T.; VanReken, T. M.

The largest global source of volatile organic compounds (VOCs) in the atmosphere is from biogenic emissions. Plant stressors associated with a changing environment can alter both the quantity and composition of the compounds that are emitted. This study investigated the effects of one global change stressor, increased herbivory, on plant emissions from five different coniferous species: bristlecone pine ( Pinus aristata), blue spruce ( Picea pungens), western redcedar ( Thuja plicata), grand fir ( Abies grandis), and Douglas-fir ( Pseudotsuga menziesii). Herbivory was simulated in the laboratory via exogenous application of methyl jasmonate (MeJA), a herbivory proxy. Gas-phase species weremore » measured continuously with a gas chromatograph coupled to a mass spectrometer and flame ionization detector (GC–MS–FID). Stress responses varied between the different plant types and even between experiments using the same set of saplings. Here, the compounds most frequently impacted by the stress treatment were alpha-pinene, beta-pinene, 1,8-cineol, beta-myrcene, terpinolene, limonene, and the cymene isomers. Individual compounds within a single experiment often exhibited a different response to the treatment from one another.« less

Antimicrobial activity of five essential oils from lamiaceae against multidrug-resistant Staphylococcus aureus.

PubMed

Kot, Barbara; Wierzchowska, Kamila; Piechota, Małgorzata; Czerniewicz, Paweł; Chrzanowski, Grzegorz

2018-06-11

Analysis of Lamiaceae essential oils (EOs) by GC-FID-MS revealed the presence as the major constituents of linalool (16.8%), linalyl acetate (15.7%) in Lavandula angustifolia, menthol (29.0%), menthone (22.7%), menthyl acetate (19.2%) in Mentha x piperita, terpinen-4-ol (27.1%), (E)-sabinene hydrate (12.1%), γ-terpinene (10.0%) in Origanum majorana, α-thujone (19.5%), camphor (19.0%), viridiflorol (13.5%) in Salvia officinalis, thymol (61.9%), p-cymene (10.0%), γ-terpinene (10.0%) in Thymus vulgaris. Based on the MIC and MBC values (0.09-0.78 mg/mL) and ratio MBC/MIC showed that EO from T. vulgaris (TO) had the strong inhibitory and bactericidal effect against multidrug-resistant Staphylococcus aureus. The bacterial cells were total killed by TO at 2MIC concentration after 6 h. The higher concentrations of other EOs were needed to achieve bactericidal effects. The strong bactericidal effect of TO against these bacteria indicates the possibility of topical use of TO but it requires research under clinical conditions.

Chemical composition and antimicrobial activity of Satureja kitaibelii essential oil against pathogenic microbial strains.

PubMed

Mihajilov-Krstev, Tatjana; Kitić, Dusanka; Radnović, Dragan; Ristić, Mihajlo; Mihajlović-Ukropina, Mira; Zlatković, Bojan

2011-08-01

Plant species Satureja kitaibelii Wierzb. ex Heuff. is used as a spice and as a natural preservative for food and herbal tea, owing to its characteristic scent and flavor as well as high antimicrobial activity. In the present study, the antimicrobial activity of isolated essential oil of S. kitaibelii was tested against a panel of 30 pathogenic microorganisms (foodborne microbes, selected multiresistant bacterial isolates from the patient wounds and dermatophyte isolates). Limonene (15.54%), p-cymene (9.99%), and borneol (8.91%) appeared as the main components in 44 identified compounds representing 98.44% of the oil. Essential oil of S. kitaibelii showed significant activity against a wide spectrum of foodborne microbes (MIC=0.18-25.5 microg mL(-1)) and multiresistant bacterial isolates (MIC=6.25-50.0 microg mL(-1)), as well as against dermatophyte strains (MIC=12.5-50.0 microg mL(-1)). These results demonstrate that S. kitaibelii essential oil could be used as a natural potential antimicrobial agent against pathogenic strains in the treatment of foodborne disease, wound and skin infections.

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.

Characterization of Volatile Compounds of Eleven Achillea Species from Turkey and Biological Activities of Essential Oil and Methanol Extract of A. hamzaoglui Arabacı & Budak.

PubMed

Turkmenoglu, Fatma Pinar; Agar, Osman Tuncay; Akaydin, Galip; Hayran, Mutlu; Demirci, Betul

2015-06-22

According to distribution of genus Achillea, two main centers of diversity occur in S.E. Europe and S.W. Asia. Diversified essential oil compositions from Balkan Peninsula have been numerously reported. However, report on essential oils of Achillea species growing in Turkey, which is one of the main centers of diversity, is very limited. This paper represents the chemical compositions of the essential oils obtained by hydrodistillation from the aerial parts of eleven Achillea species, identified simultaneously by gas chromatography and gas chromatography-mass spectrometry. The main components were found to be 1,8-cineole, p-cymene, viridiflorol, nonacosane, α-bisabolol, caryophyllene oxide, α-bisabolon oxide A, β-eudesmol, 15-hexadecanolide and camphor. The chemical principal component analysis based on thirty compounds identified three species groups and a subgroup, where each group constituted a chemotype. This is the first report on the chemical composition of A. hamzaoglui essential oil; as well as the antioxidant and antimicrobial evaluation of its essential oil and methanolic extract.

Impacts of simulated herbivory on VOC emission profiles from coniferous plants

DOE PAGES

Faiola, C. L.; Jobson, B. T.; VanReken, T. M.

2014-09-18

The largest global source of volatile organic compounds (VOCs) in the atmosphere is from biogenic emissions. Plant stressors associated with a changing environment can alter both the quantity and composition of the compounds that are emitted. This study investigated the effects of one global change stressor, increased herbivory, on plant emissions from five different coniferous species: bristlecone pine ( Pinus aristata), blue spruce ( Picea pungens), western redcedar ( Thuja plicata), grand fir ( Abies grandis), and Douglas-fir ( Pseudotsugas menziesii). Herbivory was simulated in the laboratory via exogenous application of methyl jasmonate, an herbivory proxy. Gas-phase species were measuredmore » continuously with a gas chromatograph coupled to a mass spectrometer and flame ionization detector (GC-MS-FID). Stress responses varied between the different plant types and even between experiments using the same set of saplings. The compounds most frequently impacted by the stress treatment were alpha-pinene, beta-pinene, 1,8-cineol, beta-myrcene, terpinolene, limonene, and the cymene isomers. Individual compounds within a single experiment often exhibited a different response to the treatment from one another.« less

Impacts of simulated herbivory on volatile organic compound emission profiles from coniferous plants

DOE PAGES

Faiola, C. L.; Jobson, B. T.; VanReken, T. M.

2015-01-28

The largest global source of volatile organic compounds (VOCs) in the atmosphere is from biogenic emissions. Plant stressors associated with a changing environment can alter both the quantity and composition of the compounds that are emitted. This study investigated the effects of one global change stressor, increased herbivory, on plant emissions from five different coniferous species: bristlecone pine ( Pinus aristata), blue spruce ( Picea pungens), western redcedar ( Thuja plicata), grand fir ( Abies grandis), and Douglas-fir ( Pseudotsuga menziesii). Herbivory was simulated in the laboratory via exogenous application of methyl jasmonate (MeJA), a herbivory proxy. Gas-phase species weremore » measured continuously with a gas chromatograph coupled to a mass spectrometer and flame ionization detector (GC–MS–FID). Stress responses varied between the different plant types and even between experiments using the same set of saplings. Here, the compounds most frequently impacted by the stress treatment were alpha-pinene, beta-pinene, 1,8-cineol, beta-myrcene, terpinolene, limonene, and the cymene isomers. Individual compounds within a single experiment often exhibited a different response to the treatment from one another.« less

Selective borane reduction of phosphinoferrocene carbaldehydes to phosphinoalcohol-borane adducts. The coordination behaviour of 1-(diphenylphosphino)-1'-(methoxymethyl)ferrocene, a new ferrocene O,P-hybrid donor prepared from such an adduct.

PubMed

Stěpnička, Petr; Císařová, Ivana

2013-03-14

The reduction of ferrocene phosphino-aldehydes, R(2)PfcCHO (R = Ph, 2; Cy, 3; fc = ferrocene-1,1'-diyl, Cy = cyclohexyl) and (S(p))-[Fe(η(5)-C(5)H(3)-1-CHO-2-PPh(2))(η(5)-C(5)H(5))] ((S(p))-4), with BH(3)·THF or BH(3)·SMe(2) in THF at 0 °C selectively afforded the corresponding phosphinoalcohol-borane adducts, R(2)PfcCH(2)OH·BH(3) (R = Ph, 5; Cy, 6) and (S(p))-[Fe(η(5)-C(5)H(3)-1-CH(2)OH-2-PPh(2))(η(5)-C(5)H(5))]·BH(3) ((S(p))-7), in quantitative yields. In contrast, the reactions performed at elevated temperatures favoured the formation of methyl derivatives (e.g., Ph(2)PfcCH(3)·BH(3) (8)) resulting from overreduction (deoxygenation). The crystal structures of 3, 5, (S(p))-7, 8 and Cy(2)PfcBr (9) have been determined by single-crystal X-ray diffraction analysis. The crystal assemblies of adducts 5 and (S(p))-7 are built up by means of C-H...O contacts, O-H...HB dihydrogen bonds and other soft interactions but, surprisingly, not via the conventional O-H...O hydrogen bonds. Adduct 5 was smoothly deprotected to give the corresponding free phosphine, Ph(2)PfcCH(2)OH (1), and was further used for the preparation of a hybrid phosphinoether ligand, Ph(2)PfcCH(2)OMe (11). The latter compound was studied as a donor for Group 8-10 metal ions and for Cu(i), whereupon the following complexes were isolated and structurally characterised: [(η(6)-p-cymene)RuCl(2)(11-κP)] (12*), [(η(6)-p-cymene)RuCl(11-κP)(MeCN)][SbF(6)] (13*), [RhCl(cod)(11-κP)] (cod = η(2):η(2)-cycloocta-1,5-diene; 14), trans-[PdCl(2)(11-κP)(2)] (trans-15*), [PdCl(μ-Cl)(11-κP)](2) (16*), cis- and trans-[PtCl(2)(11-κP)(2)] (cis-17 and trans-17*), and [Cu(CF(3)SO(3)-κO)(11-κP)(H(2)O)] (18) (the asterisk indicates that the crystal structure was determined). In all these compounds, ligand 11 behaves as a P-monodentate donor while its ether group remains uncoordinated. This probably reflects structural flexibility of 11 resulting from the presence of the methylene linker and also distinguishes 11 from its known, non-spaced analogue Ph(2)PfcOMe.

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.

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

A new bioactive monoterpene-flavonoid from Satureja khuzistanica.

PubMed

Malmir, Maryam; Gohari, Ahmad Reza; Saeidnia, Soodabeh; Silva, Olga

2015-09-01

A new monoterpene-flavonoid, saturejin (3'-(2,5-dihydroxy-p-cymene) 5,7,4'-trihydroxy flavone) (4), together with twelve known flavonoids consist of two flavanonols (aromadendrin (8) and taxifolin (12)), two flavanones (naringenin (3) and 5,7,3',5'-tetrahydroxy flavanone (9)) and eight flavones (xanthomicrol (1), acacetin (2), cirsimaritin (5), 7-methoxy luteolin (6), apigenin (7), cirsilineol (10), diosmetin (11) and 6-hydroxyluteolin 7,3'-dimethyl ether (13)), were isolated from an ethyl acetate extract and identified for the first time in the dried aerial parts of Satureja khuzistanica Jamzad, an endemic medicinal plant traditionally used as dental anesthetic, oral antiseptic and anti-inflammatory among the nomadic inhabitants of southwestern Iran. The structures of these compounds were determined using the usual spectroscopic methods including 2D-NMR and MS analyses. Saturejin showed a significant β-glucosidase inhibitory activity at concentration of 10 μg as well as positive antioxidant activity at the amount of 1 μg. These results could be correlated with the in vitro and in vivo anti-inflammatory, anti-oxidant and anti-diabetic properties reported from this medicinal plant. Similar activities were also described for some of the other isolated compounds. Copyright © 2015 Elsevier B.V. All rights reserved.

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.

An investigation of matched index of refraction technique and its application in optical measurements of fluid flow

NASA Astrophysics Data System (ADS)

Amini, Noushin; Hassan, Yassin A.

2012-12-01

Optical distortions caused by non-uniformities of the refractive index within the measurement volume is a major impediment for all laser diagnostic imaging techniques applied in experimental fluid dynamic studies. Matching the refractive indices of the working fluid and the test section walls and interfaces provides an effective solution to this problem. The experimental set-ups designed to be used along with laser imaging techniques are typically constructed of transparent solid materials. In this investigation, different types of aqueous salt solutions and various organic fluids are studied for refractive index matching with acrylic and fused quartz, which are commonly used in construction of the test sections. One aqueous CaCl2·2H2O solution (63 % by weight) and two organic fluids, Dibutyl Phthalate and P-Cymene, are suggested for refractive index matching with fused quartz and acrylic, respectively. Moreover, the temperature dependence of the refractive indices of these fluids is investigated, and the Thermooptic Constant is calculated for each fluid. Finally, the fluid viscosity for different shear rates is measured as a function of temperature and is applied to characterize the physical behavior of the proposed fluids.

Citral stabilization and characterization of nanoemulsions stabilized by a mixture of gelatin and Tween 20 in an acidic system.

PubMed

Tian, Huaixiang; Li, Danfeng; Xu, Ting; Hu, Jing; Rong, Yuzhi; Zhao, Bo

2017-07-01

Citral is one of the most important flavor compounds in fresh juice and lemon oil. Unfortunately, citral is chemically unstable and degrades over time in aqueous solutions. Here, citral nanoemulsions including a mixture of gelatin and Tween 20 as emulsifiers were produced in an effort to maintain the stability of citral in an acidic system. The mean droplet size and polydispersity index of the citral nanoemulsion were 467.83 nm and 0.259 respectively when the mass ratio of gelatin/Tween 20 was 3:1 and the total emulsifier concentration of the emulsion system was 10 g kg -1 . The citral nanoemulsion remained stable during storage for 14 days at 30 °C. Therefore this nanoemulsion system effectively protected citral from degradation and decreased the formation of off-flavor compounds (e.g. p-cymene, p-cresol and p-methylacetophenone) relative to a single emulsifier. The mixture of gelatin and Tween 20 enhanced the stability of citral under acidic conditions and could be used as an effective emulsifier to protect citral from degradation under acidic environments in the food industry. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

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.

Screening chemical composition and in vitro antioxidant and antimicrobial activities of the essential oils from Origanum syriacum L. growing in Turkey.

PubMed

Alma, Mehmet Hakki; Mavi, Ahmet; Yildirim, Ali; Digrak, Metin; Hirata, Toshifumi

2003-12-01

In the present study, essential oil from the leaves of Syrian oreganum [Origanum syriacum L. (Lauraceae)] grown in Turkish state forests of the Dortyol district, Turkey, was obtained by steam distillation. The chemical composition of oil was analysed by GC and GC-MS, and was found to contain 49.02% monoterpenes, 36.60% oxygenated monoterpenes and 12.59% sesquiterpenes. The major components are as follows: gamma-terpinene, carvacrol, p-cymene and beta-caryophyllene. Subsequently, the reducing power, antioxidant and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activities of the essential oil were studied. The reducing power was compared with ascorbic acid, and the other activities were compared with 2,6-di-tert-butyl-4-methyl phenol (BHT, butylated hydroxytoluene). The results showed that the activities were concentration dependent. The antioxidant activities of the oil were slightly lower than those of ascorbic acid or BHT, so the oil can be considered an effective natural antioxidant. Antimicrobial activities of the essential oil from the leaves of Origanum syriacum was also determined on 16 microorganisms tested using the agar-disc diffusion method, and showed antimicrobial activity against 13 of these.

The Biological Activity and Composition of the Essential Oil of Sclerorhachis leptoclada (Asteraceae-Anthemideae) from Iran

PubMed Central

Sonboli, Ali; Mirjalili, Mohammad Hossein; Hadian, Javad; Yousefzadi, Morteza

2014-01-01

The biological activity and composition of the essential oil of Sclerorhachis leptoclada Rech. f. an endemic species from northeast of Iran was studied. The essential oil was isolated from the aerial flowering parts of the plant and analyzed by GC and GC-MS. Fifty-four compounds accounting for 95.9% of the total oil were characterized. The main constituents were (E)-nerolidol (14.5%), terpinen-4-ol (13.3%), camphor (6.1%), 1,8-cineole (4.8%) and p-cymene (4.5%). The antimicrobial activity of the essential oil of S. leptoclada was tested against eight microbial strains and a fungi. The results of the bioassays showed that the Gram-positive bacteria, Bacillus subtilis and Staphylococcus epidermidis, were the most sensitive to the oil than others with the MIC value of 1.8 mg/mL. The tested fungi, Saccharomyces cerevisiae was highly inhibited by the oil of S. leptoclada with MIC value of 10 mg/mL. In the case of cytotoxicity, IC50 values estimated to be 312, 1250, 625 and 1250 μg oil/mL respectively, for the Vero, SW480, MCF7, and JET 3 cancer cell lines. PMID:25276213

Impact of various lipophilic substituents on ruthenium(II), rhodium(III) and iridium(III) salicylaldimine-based complexes: synthesis, in vitro cytotoxicity studies and DNA interactions.

PubMed

Cassells, Irwin; Stringer, Tameryn; Hutton, Alan T; Prince, Sharon; Smith, Gregory S

2018-05-30

A series of bidentate salicylaldimine ligands was prepared and reacted with either [RuCl(µ-Cl)(p-cymene)] 2 , [RhCl(µ-Cl)(Cp*)] 2 or [IrCl(µ-Cl)(Cp*)] 2 . All of the compounds were characterised using an array of spectroscopic and analytical techniques, namely, nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy and mass spectrometry. Single crystal X-ray diffraction (XRD) was used to confirm the bidentate coordination mode of the salicylaldimine ligand to the metal centre. The platinum group metal (PGM) complexes were screened against the MCF7 breast cancer cell line. The ruthenium and iridium salicylaldimine complexes showed comparable or greater cytotoxicity than cisplatin against the MCF7 cancer cells, as well as greater cytotoxicity than their rhodium counterparts. Three of the salicylaldimine complexes showed potent activity in the range 18-21 µM. Two of these complexes had a greater affinity for cancerous cells than for CHO non-cancerous cells (SI > 4). Preliminary mechanistic studies suggest that the ruthenium complexes undergo solvation prior to 5'-GMP binding, whereas the iridium complexes were inert to the solvation process.

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.

Chemoprevention by essential oil of turmeric leaves (Curcuma longa L.) on the growth of Aspergillus flavus and aflatoxin production.

PubMed

Sindhu, S; Chempakam, B; Leela, N K; Suseela Bhai, R

2011-05-01

Turmeric is well known for a wide range of medicinal properties. Essential oil of turmeric leaves (Curcuma longa L.) were evaluated at varying concentrations of 0.01, 0.05, 0.1, 0.5, 0.75, 1.0 and 1.5% (v/v) in Yeast Extract Sucrose (YES) broth inoculated with spore suspension of Aspergillus flavus of 10(6)conidia/ml. These were evaluated for their potential in the control of aflatoxigenic fungus A. flavus and aflatoxin production. Turmeric leaf oil exhibited 95.3% and 100% inhibition of toxin production respectively at 1.0% and 1.5%. The extent of inhibition of fungal growth and aflatoxin production was dependent on the concentration of essential oil used. The oil exhibited significant inhibition of fungal growth as well as aflatoxins B(1) and G(1) production. The LD(50) and LD(90) were also determined. GC-MS analysis of the oil showed α-phellandrene, p-cymene and terpinolene as the major components in turmeric leaf oil. The possibility of using these phytochemical components as bio-preservatives for storage of spices is discussed. Copyright © 2011 Elsevier Ltd. All rights reserved.

Comparison of chemical composition and antibacterial activity of Nigella sativa seed essential oils obtained by different extraction methods.

PubMed

Kokoska, L; Havlik, J; Valterova, I; Sovova, H; Sajfrtova, M; Jankovska, I

2008-12-01

Nigella sativa L. seed essential oils obtained by hydrodistillation (HD), dry steam distillation (SD), steam distillation of crude oils obtained by solvent extraction (SE-SD), and supercritical fluid extraction (SFE-SD) were tested for their antibacterial activities, using the broth microdilution method and subsequently analyzed by gas chromatography and gas chromatography-mass spectrometry. The results showed that the essential oils tested differed markedly in their chemical compositions and antimicrobial activities. The oils obtained by HD and SD were dominated by p-cymene, whereas the major constituent identified in both volatile fractions obtained by SD of extracted oils was thymoquinone (ranging between 0.36 and 0.38 g/ml, whereas in oils obtained by HD and SD, it constituted only 0.03 and 0.05 g/ml, respectively). Both oils distilled directly from seeds showed lower antimicrobial activity (MICs > or = 256 and 32 microg/ml for HD and SD, respectively) than those obtained by SE-SD and SFE-SD (MICs > or = 4 microg/ml). All oil samples were significantly more active against gram-positive than against gram-negative bacteria. Thymoquinone exhibited potent growth-inhibiting activity against gram-positive bacteria, with MICs ranging from 8 to 64 microg/ml.

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

Antitumour Activity of the Microencapsulation of Annona vepretorum Essential Oil.

PubMed

Bomfim, Larissa M; Menezes, Leociley R A; Rodrigues, Ana Carolina B C; Dias, Rosane B; Rocha, Clarissa A Gurgel; Soares, Milena B P; Neto, Albertino F S; Nascimento, Magaly P; Campos, Adriana F; Silva, Lidércia C R C E; Costa, Emmanoel V; Bezerra, Daniel P

2016-03-01

Annona vepretorum Mart. (Annonaceae), popularly known as 'bruteira', has nutritional and medicinal uses. This study investigated the chemical composition and antitumour potential of the essential oil of A. vepretorum leaf alone and complexed with β-cyclodextrin in a microencapsulation. The essential oil was obtained by hydrodistillation using a Clevenger-type apparatus and analysed using GC-MS and GC-FID. In vitro cytotoxicity of the essential oil and some of its major constituents in tumour cell lines from different histotypes was evaluated using the alamar blue assay. Furthermore, the in vivo efficacy of essential oil was demonstrated in mice inoculated with B16-F10 mouse melanoma. The essential oil included bicyclogermacrene (35.71%), spathulenol (18.89%), (E)-β-ocimene (12.46%), α-phellandrene (8.08%), o-cymene (6.24%), germacrene D (3.27%) and α-pinene (2.18%) as major constituents. The essential oil and spathulenol exhibited promising cytotoxicity. In vivo tumour growth was inhibited by the treatment with the essential oil (inhibition of 34.46%). Importantly, microencapsulation of the essential oil increased in vivo tumour growth inhibition (inhibition of 62.66%). © 2015 Nordic Association for the Publication of BCPT (former Nordic Pharmacological Society).

Identification of Volatile Flavor Components by Headspace Analysis: A Quick and Easy Experiment for Introducing GC/MS

NASA Astrophysics Data System (ADS)

Kjonaas, Richard; Soller, Jean L.; McCoy, Leslee A.

1997-09-01

By placing a piece of chewing gum (Wrigley's) or a crushed piece of hard candy (LifeSavers or Runts) into a vial, followed by GC/MS analysis of a five microliter sample of the headspace, students are able to identify several of the volatile flavoring components which are present. The experiment has been used successfully with sophomore organic chemistry students, and with visiting groups of talented high school students over a three year period. Identification is simplified by handing out a list of the structural formulas of some likely candidates. Some of the components that these students easily identity include ethyl acetate, isobutyl acetate, isoamyl acetate, ethyl butyrate, benzaldehyde, benzyl alcohol, limonene, and cinnamaldehyde. Some of the more difficult to identify components include menthol, menthone, carvone, cineole, myrcene, alpha-pinene, beta-pinene, para-cymene, and gama-terpinene. Most of the major headspace components give signals whose size is comparable to that of the carbon dioxide which is present in each injection. Even with split injection, the background noise is trivial compared to the signals from the major components. The experiments were carried out with a commercially available tabletop GC/MS (Varian 3400 with Saturn MS).

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.

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.

Constituents of Cajanus cajan (L.) Millsp., Moringa oleifera Lam., Heliotropium indicum L. and Bidens pilosa L. from Nigeria.

PubMed

Ogunbinu, Akinola O; Flamini, Guido; Cioni, Pier L; Adebayo, Muritala A; Ogunwande, Isiaka A

2009-04-01

The essential oils of four plant species from Nigeria have been extracted by hydrodistillation and analyzed by GC and GC-MS. The oils of Cajanus cajan were comprised of sesquiterpenes (92.5%, 81.2% and 94.3% respectively in the leaves, stem and seeds). The major compounds identified were alpha-himachalene (9.0-11.5%), beta-himachalene (8.0-11.0%), gamma-himachalene (6.9-8.1%), alpha-humulene (7.1-8.7%) and alpha-copaene (4.5-5.6%). However, monoterpenoid compounds (81.8%) dominated the oil of Moringa oleifera with an abundance of alpha-phellandrene (25.2%) and p-cymene (24.9%). On the other hand, aldehydes (52.8%) occurred in the highest amount in Heliotropium indicum, represented by phenylacetaldehyde (22.2%), (E)-2-nonenal (8.3%) and (E, Z)-2-nonadienal (6.1%), with a significant quantity of hexahydrofarnesylacetone (8.4%). The leaf and stem oils of Bidens pilosa were dominated by sesquiterpenes (82.3% and 59.3%, respectively). The main compounds in the leaf oil were caryophyllene oxide (37.0%), beta-caryophyllene (10.5%) and humulene oxide (6.0%), while the stem oils had an abundance of hexahydrofarnesyl acetone (13.4%), delta-cadinene (12.0%) and caryophyllene oxide (11.0%). The observed chemical patterns differ considerably from previous investigations.

Observations of speciated monoterpenes above a Southeastern United States Forest and comparison with a 0-D model

NASA Astrophysics Data System (ADS)

Mcavey, K. M.; Groff, C. J.; Harkins, A. D.; Bertman, S. B.; Starn, T.; Seeley, J. S.; Shepson, P. B.

2013-12-01

Biogenic emissions of monoterpenes play a role in the formation of secondary organic aerosols (SOA) and tropospheric ozone, as well as impacting the fate of nitrogen through production of organic nitrates. Monoterpene emissions can interact with anthropgenic emissions (e.g. sulfate aerosol) to produce a variety of SOA components, such as organosulfates. Concentrations of several monoterpenes, including some combination of α-pinene, β-pinene, camphene, limonene, terpinolene, γ-terpinene, myrcene, and ρ-cymene (depending on chromatographic resolution) were quantified in a forested site in rural Alabama using an automated solid sorbent sampler/2D-GC, as part of the Southern Oxidant and Aerosol Study (SOAS). Monoterpene concentrations were relatively large in this mixed coniferous/deciduous forest, with individual terpenes maximizing at concentrations as high as 1 ppb or more, making them important OH sinks, as well as organic nitrate precursors. α-pinene was the dominant terpene measured. Diurnal patterns show a clear increase in observed monoterpene concentrations occurring in the later evening hours. In this presentation we will compare the observed terpene distribution with that from a simple landcover survey and emissions model, and discuss the relative role of isoprene and the terpenes as OH sinks, and precursors to organic nitrates, which are themselves potentially important SOA components.

Essential Oil of Aristolochia trilobata: Synthesis, Routes of Exposure, Acute Toxicity, Binary Mixtures and Behavioral Effects on Leaf-Cutting Ants.

PubMed

de Oliveira, Bruna Maria S; Melo, Carlisson R; Alves, Péricles B; Santos, Abraão A; Santos, Ane Caroline C; Santana, Alisson da S; Araújo, Ana Paula A; Nascimento, Pedro E S; Blank, Arie F; Bacci, Leandro

2017-02-25

Plants of the genus Aristolochia have been frequently reported as important medicinal plants. Despite their high bioactive potential, to date, there are no reports of their effects on leaf-cutting ants. Therefore, the present study aimed to evaluate the insecticidal activity of the essential oil of Aristolochia trilobata and its major components on Atta sexdens and Acromyrmex balzani , two species of leaf-cutting ants. The bioassays were performed regarding routes of exposure, acute toxicity, binary mixtures of the major components and behavioral effects. Twenty-five components were identified in the essential oil of A. trilobata using a gas chromatographic system equipped with a mass spectrometer and a flame ionization detector. The components found in higher proportions were sulcatyl acetate, limonene, p -cymene and linalool. The essential oil of A. trilobata and its individual major components were efficient against A. balzani and A. sexdens workers when applied by fumigation. These components showed fast and efficient insecticidal activity on ants. The components acted synergistically and additively on A. balzani and A. sexdens , respectively, and caused a strong repellency/irritability in the ants. Thus, our results demonstrate the great potential of the essential oil of A. trilobata and its major components for the development of new insecticides.

Enhanced inhibition of Aspergillus niger on sedge (Lepironia articulata) treated with heat-cured lime oil.

PubMed

Matan, N; Matan, N; Ketsa, S

2013-08-01

This study aimed to examine heat curing effect (30-100°C) on antifungal activities of lime oil and its components (limonene, p-cymene, β-pinene and α-pinene) at concentrations ranging from 100 to 300 μl ml(-1) against Aspergillus niger in microbiological medium and to optimize heat curing of lime oil for efficient mould control on sedge (Lepironia articulata). Broth dilution method was employed to determine lime oil minimum inhibitory concentration, which was at 90 μl ml(-1) with heat curing at 70°C. Limonene, a main component of lime oil, was an agent responsible for temperature dependencies of lime oil activities observed. Response surface methodology was used to construct the mathematical model describing a time period of zero mould growth on sedge as functions of heat curing temperature and lime oil concentration. Heat curing of 90 μl ml(-1) lime oil at 70°C extended a period of zero mould growth on sedge to 18 weeks under moist conditions. Heat curing at 70°C best enhanced antifungal activity of lime oil against A. niger both in medium and on sedge. Heat curing of lime oil has potential to be used to enhance the antifungal safety of sedge products. © 2013 The Society for Applied Microbiology.

Essential Oil Yield Pattern and Antibacterial and Insecticidal Activities of Trachyspermum ammi and Myristica fragrans.

PubMed

Soni, Rajgovind; Sharma, Gaurav; Jasuja, Nakuleshwar Dut

2016-01-01

Two Indian spices, Trachyspermum ammi and Myristica fragrans, were studied for their essential oil (EO) yielding pattern, insecticidal activity, antibacterial activity, and composition. The essential oils (EOs) of T. ammi (1.94 ± 30 mL/100 gm) and M. fragrans (5.93 ± 90 mL/100 gm) were extracted using hydrodistillation method. In Gas Chromatography analysis, the beta-pinene, alpha-pinene, alpha-p-menth-1-en-4-ol, Limonene, and elemicin were found as major constituents of T. ammi essential oil whereas M. fragrans essential oil mostly contains Gamma-Terpinolene, p-Cymene, Thymol, and beta-pinene. The insecticidal activities of EO were demonstrated using LC50 values against Plodia interpunctella and EO of T. ammi was found comparatively more effective than EO of M. fragrans. Further, individual EO and combination of essential oil were examined for antibacterial activity against three Gram (-) bacterial strains (E. coli-MTCC 443, P. vulgaris-MTCC 1771, and K. pneumoniae-MTCC number 7028) and three Gram (+) bacterial strains (S. aureus-MTCC 3381, B. subtilis-MTCC 10619, and B. megaterium-MTCC 2412) by well agar diffusion method. The essential oil in combination (CEO) exhibited higher antibacterial activity as compared with individual essential oils.

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.

Monoterpenes released from fruit, plant, and vegetable systems.

PubMed

Iqbal, Mohammad Asif; Kim, Ki-Hyun; Ahn, Jeong Hyeon

2014-09-29

To quantify the emission rate of monoterpenes (MTs) from diverse natural sources, the sorbent tube (ST)-thermal desorption (TD) method was employed to conduct the collection and subsequent detection of MTs by gas chromatography. The calibration of MTs, when made by both mass spectrometric (MS) and flame ionization detector (FID), consistently exhibited high coefficient of determination values (R2 > 0.99). This approach was employed to measure their emission rate from different fruit/plant/vegetable (F/P/V) samples with the aid of an impinger-based dynamic headspace sampling system. The results obtained from 10 samples (consisting of carrot, pine needle (P. sylvestris), tangerine, tangerine peel, strawberry, sepals of strawberry, plum, apple, apple peel, and orange juice) marked α-pinene, β-pinene, myrcene, α-terpinene, R-limonene, γ-terpinene, and p-cymene as the most common MTs. R-limonene was the major species emitted from citrus fruits and beverages with its abundance exceeding 90%. In contrast, α-pinene was the most abundant MT (37%) for carrot, while it was myrcene (31%) for pine needle. The overall results for F/P/V samples confirmed α-pinene, β-pinene, myrcene, α-terpinene, and γ-terpinene as common MTs. Nonetheless, the types and magnitude of MTs released from fruits were distinguished from those of vegetables and plants.

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.

Assessment of chemical and genetic variability in Tanacetum gracile accessions collected from cold desert of Western Himalaya.

PubMed

Mahajan, Vidushi; Chouhan, Rekha; Kitchlu, Surinder; Bindu, Kushal; Koul, Sushma; Singh, Bikarma; Bedi, Yashbir S; Gandhi, Sumit G

2018-06-01

Genetic diversity is essential for survival and adaptation of high altitude plants such as those of Tanacetum genus, which are constantly exposed to environmental stress. We collected flowering shoots of ten accessions of Tanacetum gracile Hook.f. & Thomson (Asteraceae) (Tg 1-Tg 10), from different regions of cold desert of Western Himalaya. Chemical profile of the constituents, as inferred from GC-MS, exhibited considerable variability. Percentage yield of essential oil ranged from 0.2 to 0.75% (dry-weight basis) amongst different accessions. Tg 1 and Tg 6 were found to produce high yields of camphor (46%) and lavandulol (41%), respectively. Alpha -phellendrene, alpha -bisabool, p -cymene and chamazulene were the main oil components in other accessions. Genetic variability among the accessions was studied using RAPD markers as well as by sequencing and analyzing nuclear 18S rDNA, and plastid rbcL and matK loci. The polymorphic information content (PIC) of RAPD markers ranged from 0.18 to 0.5 and the analysis clustered the accessions into two major clades. The present study emphasized the importance of survey, collection, and conservation of naturally existing chemotypes of medicinal and aromatic plants, considering their potential use in aroma and pharmaceutical industry.

Aphid-induced Defences in Chilli Affect Preferences of the Whitefly, Bemisia tabaci (Hemiptera: Aleyrodidae).

PubMed

Saad, Khalid A; Mohamad Roff, M N; Hallett, Rebecca H; Idris, A B

2015-09-03

The sweetpotato whitefly (WF), Bemisia tabaci, is a major pest that damages a wide range of vegetable crops in Malaysia. WF infestation is influenced by a variety of factors, including previous infestation of the host plant by other insect pests. This study investigated the effects of previous infestation of host chilli plants by the green peach aphid (Myzus persicae) on the olfactory behavioural response of B. tabaci, using free-choice bioassay with a Y-tube olfactometer. We analysed volatile organic compounds (VOCs) emitted by non-infested and M. persicae-infested chilli plants using solid-phase microextraction and gas chromatography-mass spectrometry. Our results showed that female WFs preferred non-infested to pre-infested plants. Collection and analysis of volatile compounds emitted by infested plants confirmed that there were significant increases in the production of monoterpenes (cymene; 1,8-cineole), sesquiterpenes (β-cadinene, α-copaene), and methyl salicylate (MeSA) compared to non-infested plants. Our results suggest that host plant infestation by aphids may induce production of secondary metabolites that deter B. tabaci from settling on its host plants. These results provide important information for understanding WF host selection and dispersal among crops, and also for manipulating WF behaviour to improve IPM in chilli.

Bioactive Secondary Metabolites from Schizogyne sericea (Asteraceae) Endemic to Canary Islands.

PubMed

Venditti, Alessandro; Bianco, Armandodoriano; Muscolo, Camilla; Zorzetto, Christian; Sánchez-Mateo, Candelaria C; Rabanal, Rosa M; Quassinti, Luana; Bramucci, Massimo; Damiano, Silvia; Iannarelli, Romilde; Lupidi, Giulio; Papa, Fabrizio; Petrelli, Dezemona; Vitali, Luca A; Vittori, Sauro; Maggi, Filippo

2016-07-01

Schizogyne sericea (Asteraceae) is a halophytic shrub endemic to the Canary Islands and traditionally employed as analgesic, astringent, anti-inflammatory, and vulnerary. A comprehensive phytochemical investigation was conducted on the flowering aerial parts by analyzing both essential oil constituents and polar compounds. The essential oil was dominated by p-cymene, with the noteworthy occurrence of β-pinene and thymol esters. From the EtOH extract, eight compounds were isolated and structurally elucidated. Essential oil, polar fractions, and isolates (2), (4), and (5) were separately in vitro assayed for antiproliferative activity on human tumor cell lines (A375, MDA-MB 231, and HCT116) by MTT assay, for antioxidant potential by DPPH, ABTS, and FRAP assays, and for antimicrobial activity by the agar disk diffusion method. Results revealed that essential oil and compounds 1 and 2 exert a strong inhibition on tumor cells, and in some cases, higher than that of cisplatin. Fractions containing thymol derivatives (1 and 2) and caffeoylquinic acid derivatives 4 and 5 displayed antioxidant activity comparable to that of Trolox, making S. sericea extract an interesting natural product with potential applications as preservative or in the treatment of diseases in which oxidative stress plays an important role. © 2016 Wiley-VHCA AG, Zürich.

Composition, In Vitro Antioxidant and Antimicrobial Activities of Essential Oil and Oleoresins Obtained from Black Cumin Seeds (Nigella sativa L.)

PubMed Central

Singh, Sunita; Das, S. S.; Singh, G.; Schuff, Carola; de Lampasona, Marina P.; Catalán, César A. N.

2014-01-01

Gas chromatography-mass spectrometry (GC-MS) analysis revealed the major components in black cumin essential oils which were thymoquinone (37.6%) followed by p-cymene (31.2%), α-thujene (5.6%), thymohydroquinone (3.4%), and longifolene (2.0%), whereas the oleoresins extracted in different solvents contain linoleic acid as a major component. The antioxidant activity of essential oil and oleoresins was evaluated against linseed oil system at 200 ppm concentration by peroxide value, thiobarbituric acid value, ferric thiocyanate, ferrous ion chelating activity, and 1,1-diphenyl-2-picrylhydrazyl radical scavenging methods. The essential oil and ethyl acetate oleoresin were found to be better than synthetic antioxidants. The total phenol contents (gallic acid equivalents, mg GAE per g) in black cumin essential oil, ethyl acetate, ethanol, and n-hexane oleoresins were calculated as 11.47 ± 0.05, 10.88 ± 0.9, 9.68 ± 0.06, and 8.33 ± 0.01, respectively, by Folin-Ciocalteau method. The essential oil showed up to 90% zone inhibition against Fusarium moniliforme in inverted petri plate method. Using agar well diffusion method for evaluating antibacterial activity, the essential oil was found to be highly effective against Gram-positive bacteria. PMID:24689064

A review on the inhibitory potential of Nigella sativa against pathogenic and toxigenic fungi.

PubMed

Shokri, Hojjatollah

2016-01-01

Nigella sativa (N. sativa) grows in various parts of the world, particularly in Iran. It has been traditionally used as a folk remedy to treat a number of diseases. The seeds of this plant contain moisture, proteins, carbohydrates, crude fiber, alkaloids, saponins, ash, fixed oils and essential oil. The major components of the essential oil are thymoquinone, p-cymene, trans-anethole, 2-methyl-5(1-methyl ethyl)-Bicyclo[3.1.0]hex-2-en and γ-terpinene. So far, several pharmacological effects such as anti-oxidant, anti-inflammatory, anti-cancer and anti-microbial have been reported for N. sativa or its active compounds. Thymoquinone, thymohydroquinone and thymol are the most active constituents which have different beneficial properties. The oil, extracts and some of N. sativa active components possessed moderate in vitro and in vivo inhibitory activity against pathogenic yeasts, dermatophytes, non-dermatophytic filamentous fungi and aflatoxin-producing fungi. The main morphological changes of pathogenic and toxigenic fungi treated with N. sativa oil were observed in the cell wall, plasma membrane and membranous organelles, particularly in the nuclei and mitochondria. Although this review represents first step in the search for a new anti-fungal drug, the full potential of N. sativa as a fungitoxic agent has not been exploited and necessitates further investigations.

Composition, in vitro antioxidant and antimicrobial activities of essential oil and oleoresins obtained from black cumin seeds (Nigella sativa L.).

PubMed

Singh, Sunita; Das, S S; Singh, G; Schuff, Carola; de Lampasona, Marina P; Catalán, César A N

2014-01-01

Gas chromatography-mass spectrometry (GC-MS) analysis revealed the major components in black cumin essential oils which were thymoquinone (37.6%) followed by p-cymene (31.2%), α-thujene (5.6%), thymohydroquinone (3.4%), and longifolene (2.0%), whereas the oleoresins extracted in different solvents contain linoleic acid as a major component. The antioxidant activity of essential oil and oleoresins was evaluated against linseed oil system at 200 ppm concentration by peroxide value, thiobarbituric acid value, ferric thiocyanate, ferrous ion chelating activity, and 1,1-diphenyl-2-picrylhydrazyl radical scavenging methods. The essential oil and ethyl acetate oleoresin were found to be better than synthetic antioxidants. The total phenol contents (gallic acid equivalents, mg GAE per g) in black cumin essential oil, ethyl acetate, ethanol, and n-hexane oleoresins were calculated as 11.47 ± 0.05, 10.88 ± 0.9, 9.68 ± 0.06, and 8.33 ± 0.01, respectively, by Folin-Ciocalteau method. The essential oil showed up to 90% zone inhibition against Fusarium moniliforme in inverted petri plate method. Using agar well diffusion method for evaluating antibacterial activity, the essential oil was found to be highly effective against Gram-positive bacteria.

Chemical composition, antimicrobial, antioxidant and cytotoxic activity of the essential oil from the leaves of Acanthopanax leucorrhizus (Oliv.) Harms.

PubMed

Hu, Haobin; Zheng, Xudong; Hu, Huaisheng

2012-09-01

The leaf essential oil of Acanthopanax leucorrhizus, a widely used medicinal plant, was obtained by hydrodistillation and analyzed by using combination of capillary GC-FID, GC-MS and RI. Fifty-nine components, representing 93.1% of the total oil, were identified in the essential oil and the main components of the oil were β-pinene (7.3%), linalool (6.5%), p-cymene (6.3%), β-elemene (3.8%), γ-terpinene (3.7%), spathulenol (3.2%) and cis-sabinene hydrate (3.1%). Furthermore, the in vitro antimicrobial, antioxidant and cytotoxic activities of the essential oil were examined. The test results showed that the essential oil exhibited a broad spectrum of anti-microbial activity against all microorganisms tested. Gram-positive bacteria were more sensitive to the oil than gram-negative bacteria and yeasts. The oil possessed moderate cytotoxicity on human tumor cells with lower IC(50) values of 25.65μg/ml (Hep G2), 28.71μg/ml (Hela), 30.15μg/ml (Bel-7402) and 37.55μg/ml (A-549). The moderate antioxidant activity of the oil was also evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical method. Copyright © 2012 Elsevier B.V. All rights reserved.

Essential oil composition and antibacterial activity of Tanacetum argenteum (Lam.) Willd. ssp. argenteum and T. densum (Lab.) Schultz Bip. ssp. amani heywood from Turkey.

PubMed

Polatoğlu, Kaan; Demirci, Fatih; Demirci, Betül; Gören, Nezhun; Başer, Kemal Hüsnü Can

2010-01-01

Water-distilled essential oils from aerial parts of Tanacetum argenteum ssp. argenteum and T. densum ssp. amani from Turkey were analyzed by GC and GC/MS. The essential oil of T. argenteum ssp. argenteum was characterized with alpha-pinene 36.7%, beta-pinene 27.5% and 1,8-cineole 9.8%. T. densum ssp. amani was characterized with beta-pinene 27.2%, 1,8-cineole 13.1%, alpha-pinene 9.7% and p-cymene 8.9%. Antibacterial activity of the oils were evaluated for five Gram-positive and five Gram-negative bacteria by using a broth microdilution assay. The highest inhibitory activity was observed against Bacillus cereus for T. argenteum ssp. argenteum oil (125 microg/mL) when compared with positive control chloramphenicol it showed the same inhibition potency. However, the same oil showed lower inhibitory activity against B. subtilis when compared. The oil of T. densum ssp. amani did not show significant activity against the tested microorganisms. DPPH radical scavenging activity of the T. argenteum ssp. argenteum oil was investigated for 15 and 10 mg/mL concentrations. However, the oil did not show significant activity when compared to positive control alpha-tocopherol. Both oils showed toxicity to Vibrio fischeri in the TLC-bioluminescence assay.

Ligand effects on the hydrogenation of biomass-inspired substrates with bifunctional Ru, Ir, and Rh complexes.

PubMed

Jansen, Eveline; Jongbloed, Linda S; Tromp, Dorette S; Lutz, Martin; de Bruin, Bas; Elsevier, Cornelis J

2013-09-01

We herein report on the application and structural investigation of a new set of complexes that contain bidentate N-heterocyclic carbenes (NHCs) and primary amine moieties of the type [M(arene)Cl(L)] [M=Ru, Ir, or Rh; arene=p-cymene or pentamethylcyclopentadienyl; L=1-(2-aminophenyl)-3-(n-alkyl)imidazol-2-ylidine]. These complexes were tested and compared in the hydrogenation of acetophenone with hydrogen. Structural variations in the chelate ring size of the heteroditopic ligand revealed that smaller chelate ring sizes in combination with ring conjugation in the ligand are beneficial for the activity of this type of catalyst, favoring an inner-sphere coordination pathway. Additionally, increasing the steric bulk of the alkyl substituent on the NHC aided the reaction, showing almost no induction period and formation of a more active catalyst for the n-butyl complex relative to complexes with smaller Me and Et substituents. As is common in hydrogenation reactions, the activity of the complexes decreases in the order Ru>Ir>Rh. The application of [Ru(p-cym)Cl(L)]PF6 , which outperforms its reported analogues, has been successfully extended to the hydrogenation of more challenging biomass-inspired substrates. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Combined effects of oregano essential oil and salt on the growth of Escherichia coli in salad dressing.

PubMed

Cattelan, Marília Gonçalves; Nishiyama, Yara Paula de Oliveira; Gonçalves, Tânia Maria Vinturim; Coelho, Alexandre Rodrigo

2018-08-01

There is a broad research interest in the search for alternatives to chemical additives for use as natural food preservatives. Although many natural compounds have biological in vitro properties evidenced, in situ studies are still scarce. This study evaluated the effect of oregano essential oil (OEO) and salt (NaCl) concentrations against Escherichia coli (ATCC 8739), in salad dressing, using the response surface methodology. The experiment included a 2 2 central composite rotatable design (CCRD) in a total of 11 formulations of salad dressings. Oregano essential oil was characterized by gas chromatography and salad dressings by ash, lipids, proteins and moisture. OEO was composed mainly by carvacrol (65.1%) and p-cymene (12.0%). Salad dressings showed similar chemical profiles. A mathematical model for the prediction of the antibacterial activity in salad dressing was obtained. The results revealed that the interaction between OEO and salt showed effect on the bacterial count. However, the effect of salt was negative suggesting that the highest NaCl concentrations decreases the bacterial count. Therefore, within the parameters studied, the use of OEO to control E. coli in salad dressing can be considered promising and allows reduction in the levels of salt to be incorporated in food. Copyright © 2018 Elsevier Ltd. All rights reserved.

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

In vitro analysis of the properties of Beiqishen tea.

PubMed

Blázovics, A; Szentmihályi, K; Lugasi, A; Balázs, A; Hagymási, K; Bányai, E; Then, M; Rapavi, E; Héthelyi, E

2003-10-01

Chinese Beiqishen tea was studied in an in vitro test system. Phytochemical screening, trace element analysis, and the analysis of antioxidant properties were carried out. Characteristic constituents were determined by chromatographic (capillary gas chromatography and GCQ Ion Trap mass spectrometry) and spectrometric (ultraviolet and UV-VIS) methods. Element concentrations were determined by inductively coupled plasma optical emission spectrometry. Antioxidant capacity was studied by spectrophotometric and luminometric techniques using a Berthold Lumat 9501 luminometer. Hydrogen-donating activity, reducing power, and total scavenger capacity were measured. Total polyphenol content was 20.77 +/- 0.52 g/100 g of drug; total flavonoid content was 0.485 +/- 0.036 g/100 g of drug; and tannin content was 9.063 +/- 0.782 g/100 g of drug. Caffeine content was 1.08 mg/100 g of drug. Essential oils were identified by gas chromatography: (+)-limonene (21%), p-cymene (1.7%), estragol (3.2%), beta-ocimene (1.4%), and thymol (2.6%). Metallic ion analysis showed significantly high concentrations of Al, As, Ba, Cr, Cu, Fe, Mn, Ni, and Ti in the drug. Antioxidant and scavenger properties were identified as a function of concentration. The tea infusion contained some non-desirable trace elements and caffeine in addition to polyphenols and tannins in high concentrations. Therefore, the consumption of this tea may involve risks.

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.

Characterization of the volatile constituents in the essential oil of Pistacia lentiscus L. from different origins and its antifungal and antioxidant activity.

PubMed

Barra, Andrea; Coroneo, Valentina; Dessi, Sandro; Cabras, Paolo; Angioni, Alberto

2007-08-22

Essential oil (EO) from aerial parts (leaves, juvenile branches, and flowers when present) of Pistacia lentiscus L. growing wild in five localities of Sardinia (Italy) was extracted by steam-distillation (SD) and analyzed by gas chromatography (GC), FID, and GC-ion trap mass spectrometry (ITMS). Samples of P. lentiscus L. were harvested between April and October to study the seasonal chemical variability of the EO. A total of 45 compounds accounting for 97.5-98.4% of the total EO were identified, and the major compounds were alpha-pinene (14.8-22.6%), beta-myrcene (1-19.4%), p-cymene (1.6-16.2%), and terpinen-4-ol (14.2-28.3%). The yields of EO (v/dry w) ranged between 0.09 and 0.32%. Similar content of the major compounds was found in samples from different origins and seasonal variability was also observed. The EOs were tested for their antifungal activity against Aspergillus flavus, Rhizoctonia solani, Penicillium commune, Fusarium oxysporum. Two samples were weakly effective against Aspergillus flavus. Furthermore, terpinenol and alpha-terpineol, two of the major components of EO of Pistacia lentiscus L., totally inhibited the mycelian growth of A. flavus. Quite good antioxidant activity of the EO was also found.

Antimycotoxigenic characteristics of Rosmarinus officinalis and Trachyspermum copticum L. essential oils.

PubMed

Rasooli, Iraj; Fakoor, Mohammad Hadi; Yadegarinia, Davod; Gachkar, Latif; Allameh, Abdolamir; Rezaei, Mohammad Bagher

2008-02-29

Aflatoxin B1 (AFB1) is a highly toxic and carcinogenic metabolite produced by Aspergillus species on food and agricultural commodities. Natural products may regulate the cellular effects of aflatoxins and evidence suggests that aromatic organic compounds of spices can control the production of aflatoxins. With a view to controlling aflatoxin production, the essential oils from Rosmarinus officinalis and Trachyspermum copticum L. were obtained by hydrodistillation. Antifungal activities of the oils were studied with special reference to the inhibition of Aspergillus parasiticus growth and aflatoxin production. Minimal inhibitory (MIC) and minimal fungicidal (MFC) concentrations of the oils were determined. T. copticum L. oil showed a stronger inhibitory effect than R. officinalis on the growth of A. parasiticus. Aflatoxin production was inhibited at 450 ppm of both oils with that of R. officinalis being stronger inhibitor. The oils were analyzed by GC and GC/MS. The major components of R. officinalis and T. copticum L. oils were Piperitone (23.65%), alpha-pinene (14.94%), Limonene (14.89%), 1,8-Cineole (7.43%) and Thymol (37.2%), P-Cymene (32.3%), gamma-Terpinene (27.3%) respectively. It is concluded that the essential oils could be safely used as preservative materials on some kinds of foods to protect them from toxigenic fungal infections.

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.

Osmium Atoms and Os2 Molecules Move Faster on Selenium-Doped Compared to Sulfur-Doped Boronic Graphenic Surfaces.

PubMed

Barry, Nicolas P E; Pitto-Barry, Anaïs; Tran, Johanna; Spencer, Simon E F; Johansen, Adam M; Sanchez, Ana M; Dove, Andrew P; O'Reilly, Rachel K; Deeth, Robert J; Beanland, Richard; Sadler, Peter J

2015-07-28

We deposited Os atoms on S- and Se-doped boronic graphenic surfaces by electron bombardment of micelles containing 16e complexes [Os(p-cymene)(1,2-dicarba-closo-dodecarborane-1,2-diselenate/dithiolate)] encapsulated in a triblock copolymer. The surfaces were characterized by energy-dispersive X-ray (EDX) analysis and electron energy loss spectroscopy of energy filtered TEM (EFTEM). Os atoms moved ca. 26× faster on the B/Se surface compared to the B/S surface (233 ± 34 pm·s(-1) versus 8.9 ± 1.9 pm·s(-1)). Os atoms formed dimers with an average Os-Os distance of 0.284 ± 0.077 nm on the B/Se surface and 0.243 ± 0.059 nm on B/S, close to that in metallic Os. The Os2 molecules moved 0.83× and 0.65× more slowly than single Os atoms on B/S and B/Se surfaces, respectively, and again markedly faster (ca. 20×) on the B/Se surface (151 ± 45 pm·s(-1) versus 7.4 ± 2.8 pm·s(-1)). Os atom motion did not follow Brownian motion and appears to involve anchoring sites, probably S and Se atoms. The ability to control the atomic motion of metal atoms and molecules on surfaces has potential for exploitation in nanodevices of the future.

Chemical Components of Four Essential Oils in Aromatherapy Recipe.

PubMed

Tadtong, Sarin; Kamkaen, Narisa; Watthanachaiyingcharoen, Rith; Ruangrungsi, Nijsiri

2015-06-01

This study focused on characterization of the chemical components of an aromatherapy recipe. The formulation consisted of four blended essential oils; rosemary oil, eucalyptus oil, pine oil and lime oil (volume ratio 6 : 2 : 1 : 1). The single and combination essential oils were identified by gas chromatography-mass spectrometry (GC-MS). The analysis of GC-MS data revealed that several components exist in the mixture. The five most important components of the blended essential oils were 1,8-cineole (35.6 %), α-pinene (11.1%), limonene (9.6%), camphor (8.4%), and camphene (6.6%). The main components of rosemary oil were 1,8-cineole (37.3%), α-pinene (19.3%), camphor (14.7%), camphene (8.8%), and β-pinene (5.5%); of eucalyptus oil 1,8-cineole (82.6%) followed by limonene (7.4%), o-cymene (4.3%), γ-terpinene (2.7%), and α-pinene (1.5%); of pine oil terpinolene (26.7%), α-terpineol (20.50%), 1-terpineol (10.8%), α-pinene (6.0%), and γ-terpineol (5.3%); and of lime oil limonene (62.9%), γ-terpinene (11.5%), α-terpineol (7.6%), terpinolene (6.0%), and α-terpinene (2.8%). The present study provided a theoretical basis for the potential application of blended essential oils to be used as an aromatherapy essential oil recipe. GC-MS serves as a suitable and reliable method for the quality control of the chemical markers.

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.

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.

Nematicidal activity of essential oils and volatiles derived from Portuguese aromatic flora against the pinewood nematode, Bursaphelenchus xylophilus

PubMed Central

Barbosa, P.; Lima, A. S.; Vieira, P.; Dias, L. S.; Tinoco, M. T.; Barroso, J. G.; Pedro, L. G.; Figueiredo, A. C.

2010-01-01

Twenty seven essential oils, isolated from plants representing 11 families of Portuguese flora, were screened for their nematicidal activity against the pinewood nematode (PWN), Bursaphelenchus xylophilus. The essential oils were isolated by hydrodistillation and the volatiles by distillation-extraction, and both were analysed by GC and GC-MS. High nematicidal activity was achieved with essential oils from Chamaespartium tridentatum, Origanum vulgare, Satureja montana, Thymbra capitata, and Thymus caespititius. All of these essential oils had an estimated minimum inhibitory concentration ranging between 0.097 and 0.374 mg/ml and a lethal concentration necessary to kill 100% of the population (LC100) between 0.858 and 1.984 mg/ml. Good nematicidal activity was also obtained with the essential oil from Cymbopogon citratus. The dominant components of the effective oils were 1–octen-3-ol (9%), n–nonanal, and linalool (both 7%) in C. tridentatum, geranial (43%), neral (29%), and β-myrcene (25%) in C. citratus, carvacrol (36% and 39%), γ-terpinene (24% and 40%), and p-cymene (14% and 7%) in O. vulgare and S. montana, respectively, and carvacrol (75% and 65%, respectively) in T. capitata and T. caespititius. The other essential oils obtained from Portuguese flora yielded weak or no activity. Five essential oils with nematicidal activity against PWN are reported for the first time. PMID:22736831

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

Larvicidal Activity of Essential Oils of Five Apiaceae Taxa and Some of Their Main Constituents Against Culex quinquefasciatus.

PubMed

Pavela, Roman; Maggi, Filippo; Cianfaglione, Kevin; Bruno, Maurizio; Benelli, Giovanni

2018-01-01

Apiaceae are aromatic herbs producing essential oils which are used on an industrial scale for various purposes. Notably, Apiaceae essential oils may replace synthetic insecticides keeping most of their efficacy and avoiding environmental pollution and human poisoning. In the present work, we explored the insecticidal potential of the essential oils from five Apiaceae taxa, namely Sison amomum, Echinophora spinosa, Heracleum sphondylium subsp. sphondylium, Heracleum sphondylium subsp. ternatum, and Trachyspemum ammi, as well as their major constituents (sabinene, p-cymene, terpinolene, myristicin, and thymol), against the filariasis vector Culex quinquefasciatus. For the purpose, the essential oils were obtained by hydrodistillation and their composition was achieved by gas chromatography/mass spectrometry (GC/MS). Their acute toxicity on third instar larvae of C. quinquefasciatus was determined. The two most active essential oils were those from T. ammi fruits and E. spinosa roots, showing LC 50 below 20 μl/l and LD 90 below 50 μl/l. These oils were dominated by the monoterpene phenol thymol and the phenylpropanoid myristicin, respectively, which showed the strongest larvicidal activity (LC 50 of 15.1 and 16.3 μl/l, respectively) among the pure compounds tested. These results showed that Apiaceae may be useful as source of larvicidal compounds to be used for the development of cheap, effective and eco-friendly insecticidal formulations. © 2018 Wiley-VHCA AG, Zurich, Switzerland.

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.

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.

Biomolecular characterization of wild sicilian oregano: phytochemical screening of essential oils and extracts, and evaluation of their antioxidant activities.

PubMed

Tuttolomondo, Teresa; La Bella, Salvatore; Licata, Mario; Virga, Giuseppe; Leto, Claudio; Saija, Antonella; Trombetta, Domenico; Tomaino, Antonio; Speciale, Antonio; Napoli, Edoardo M; Siracusa, Laura; Pasquale, Andrea; Curcuruto, Giusy; Ruberto, Giuseppe

2013-03-01

An extensive survey of wild Sicilian oregano was made. A total of 57 samples were collected from various sites, followed by taxonomic characterization from an agronomic perspective. Based on morphological and production characteristics obtained from the 57 samples, cluster analysis was used to divide the samples into homogeneous groups, to identify the best biotypes. All samples were analyzed for their phytochemical content, applying a cascade-extraction protocol and hydrodistillation, to obtain the non volatile components and the essential oils, respectively. The extracts contained thirteen polyphenol derivatives, i.e., four flavanones, seven flavones, and two organic acids. Their qualitative and quantitative characterization was carried out by LC/MS analyses. The essential oils were characterized using a combination of GC-FID and GC/MS analyses; a total of 81 components were identified. The major components of the oils were thymol, p-cymene, and γ-terpinene. Cluster analysis was carried out on both phytochemical profiles and resulted in the division of the oregano samples into different chemical groups. The antioxidant activity of the essential oils and extracts was investigated by the Folin-Ciocalteau (FC) colorimetric assay, by UV radiation-induced peroxidation in liposomal membranes (UV-IP test), and by determining the O(2)(∙-)-scavenging activity. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.

Cytotoxic hydrogen bridged ruthenium quinaldamide complexes showing induced cancer cell death by apoptosis.

PubMed

Lord, Rianne M; Allison, Simon J; Rafferty, Karen; Ghandhi, Laura; Pask, Christopher M; McGowan, Patrick C

2016-08-16

This report presents the first known p-cymene ruthenium quinaldamide complexes which are stabilised by a hydrogen-bridging atom, [{(p-cym)Ru(II)X(N,N)}{H(+)}{(N,N)XRu(II)(p-cym)}][PF6] (N,N = functionalised quinaldamide and X = Cl or Br). These complexes are formed by a reaction of [p-cymRu(μ-X)2]2 with a functionalised quinaldamide ligand. When filtered over NH4PF6, and under aerobic conditions the equilibrium of NH4PF6 ⇔ NH3 + HPF6 enables incorporation of HPF6 and the stabilisation of two monomeric ruthenium complexes by a bridging H(+), which are counter-balanced by a PF6 counterion. X-ray crystallographic analysis is presented for six new structures with OO distances of 2.420(4)-2.448(15) Å, which is significant for strong hydrogen bonds. Chemosensitivity studies against HCT116, A2780 and cisplatin-resistant A2780cis human cancer cells showed the ruthenium complexes with a bromide ancillary ligand to be more potent than those with a chloride ligand. The 4'-fluoro compounds show a reduction in potency for both chloride and bromide complexes against all cell lines, but an increase in selectivity towards cancer cells compared to non-cancer ARPE-19 cells, with a selectivity index >1. Mechanistic studies showed a clear correlation between IC50 values and induction of cell death by apoptosis.

The storage stability of biogenic volatile organic compounds (BVOCs) in polyester aluminum bags

NASA Astrophysics Data System (ADS)

Ahn, Jeong-Hyeon; Deep, Akash; Kim, Ki-Hyun

2016-09-01

In this study, the sorptive loss properties of biogenic volatile organic compounds (BVOCs) in polyester aluminum bags were investigated as a function of storage duration. To this end, the relative recovery of gas phase standards of BVOCs, obtained via vaporization of liquid phase standards, was computed by calibrating their standards (response factors: RF) represnting each phase. Accordingly, the results indicated either slight loss (-5.59% (isoprene), -2.39% (camphene), -1.69% ((R)-(+)-limonene), -0.88% (p-cymene)) or gain (1.47% (γ-terpinene), 2.27% (α-terpinene), 2.63% (α-phellandrene), 2.73% ((+)-3-carene), 3.93% ((+)-β-pinene), and 5.98% ((+)-α-pinene)). Through comparison of the calibration results across storage time, the temporal stability of BVOCs was assessed. Longer BVOC storage time in polyester aluminum (PEA) bags lowered the relative recovery of BVOCs. The relative loss of BVOCs, if calculated in terms of mean bag standard RF ratios (relative to liquid standard) across elapsed time, decreased systematically: 0.99 ± 0.05 (0 h), 0.88 ± 0.06 (24 h), 0.66 ± 0.11 (72 h), and 0.62 ± 0.14 (120 h). It is thus recommended to complete the analysis of BVOC in PEA bags within 24 h of sample acquisition. As such, it is important to apply appropriate sampling approaches with a proper storage plan when measuring ambient BVOCs collected by bag sampling methods.

Chemical composition and biological activities of Tunisian Cuminum cyminum L. essential oil: a high effectiveness against Vibrio spp. strains.

PubMed

Hajlaoui, Hafedh; Mighri, Hedi; Noumi, Emira; Snoussi, Mejdi; Trabelsi, Najla; Ksouri, Riadh; Bakhrouf, Amina

2010-01-01

Essential oil extracted by hydrodistillation from Tunisian variety of Cuminumcyminum was characterized by means of GC and GC-MS. Twenty-one components were identified and C. cyminum contained cuminlaldehyde (39.48%), gamma-terpinene (15.21%), O-cymene (11.82%), beta-pinene (11.13%), 2-caren-10-al (7.93%), trans-carveol (4.49%) and myrtenal (3.5%) as a major components. Moreover, C. cyminum oil exhibited higher antibacterial and antifungal activities with a high effectiveness against Vibrio spp. strains with a diameter of inhibition zones growth ranging from 11 to 23 mm and MIC and MBC values ranging from (0.078-0.31 mg/ml) to (0.31-1.25mg/ml), respectively. On the other hand, the cumin oil was investigated for its antioxidant activities using four different tests then compared with BHT. Results showed that cumin oil exhibit a higher activity in each antioxidant system with a special attention for beta-carotene bleaching test (IC(50): 20 microg/ml) and reducing power (EC(50): 11 microg/ml). In the light of these findings, we suggested that C. cyminum essential oil may be considered as an interesting source of antibacterial, antifungal and antioxidants components used as potent agents in food preservation and for therapeutic or nutraceutical industries. Copyright (c) 2010. Published by Elsevier Ltd.

Chemical compositions and antibacterial activities of the essential oils from aerial parts and corollas of Origanum acutidens (Hand.-Mazz.) Ietswaart, an endemic species to Turkey.

PubMed

Cosge, Belgin; Turker, Arzu; Ipek, Arif; Gurbuz, Bilal

2009-04-30

Essential oils extracted by hydrodistillation from the aerial parts and corollas of Origanum acutidens (Hand.-Mazz.) Ietswaart, an endemic Turkish flora species, were analyzed by GC-MS. The amounts of essential oil obtained from the aerial parts and the corollas were 0.73% and 0.93%, respectively. Twenty-five components in both the aerial parts oil and the corolla oil, representing 95.11% and 93.88%, respectively, were identified. The aerial parts and corolla oils were characterized by the predominance of two components: p-cymene (9.43% and 17.51%) and carvacrol (67.51% and 52.33%), respectively. The essential oils were also evaluated for their antimicrobial activity against ten bacteria by the disc diffusion assay. Our findings showed the following order in the sensitivity to the essential oils, as indicated by the corresponding inhibition zones: Proteus vulgaris > Salmonella typhimurium > Enterobacter cloacae > Klebsiella pneumonia > Escherichia coli > Serratia marcescens > Pseudomonas aeruginosa for the aerial parts essential oil, and Salmonella typhimurium > Proteus vulgaris > Enterobacter cloacae > Escherichia coli > Klebsiella pneumoniae > Serratia marcescens > Pseudomonas aeruginosa for the corolla essential oil. The studied essential oils thus exhibited a broad-spectrum of activity against both Gram-positive and Gram-negative bacteria, whereas the tested Gram-positive bacteria were more susceptible to the essential oil samples.

Relationship between sensory attributes and volatile compounds of polish dry-cured loin

PubMed Central

Górska, Ewa; Nowicka, Katarzyna; Jaworska, Danuta; Przybylski, Wiesław; Tambor, Krzysztof

2017-01-01

Objective The aim of this work was to determine the relationship between objective sensory descriptors and volatile flavour compound composition of Polish traditional dry-cured loin. Methods The volatile compounds were investigated by using solid phase microextraction (SPME) and gas chromatography–mass spectrometry (GC–MS). For sensory assessment, the quantitative descriptive analysis (QDA) method was used. Results A total of 50 volatile compounds were found and assigned to 17 chemical families. Most of the detected volatile compounds derived from smoking, lipid oxidative reactions and seasoning (46.8%, 21.7%, and 18.9%, respectively). The dominant compounds were: aromatic hydrocarbon (toluene); alkanes (hexane, heptane, and 2,2,4-trimethylpentane); aldehyde (hexanal); alcohol (2-furanmethanol); ketone (3-hydroxy-2-butanone); phenol (guaiacol); and terpenes (eucalyptol, cymene, γ-terpinen, and limonene). Correlation analysis showed that some compounds derived from smoking were positively correlated with the intensity of cured meat odour and flavour and negatively with the intensity of dried meat odour and flavour, while terpenes were strongly correlated with odour and flavour of added spices. Conclusion The analysed dry-cured loins were characterized by specific and unique sensory profile. Odour and flavour of studied loins was mainly determined by volatile compounds originating from smoking, seasoning and lipid oxidation. Obtained results suggest that smoking process is a crucial stage during Polish traditional dry-cured loins production. PMID:27456422

Cyclopentadienyl ruthenium-nickel catalysts for biomimetic hydrogen evolution: electrocatalytic properties and mechanistic DFT studies.

PubMed

Canaguier, Sigolène; Vaccaro, Loredana; Artero, Vincent; Ostermann, Rainer; Pécaut, Jacques; Field, Martin J; Fontecave, Marc

2009-09-21

The new dinuclear nickel-ruthenium complexes [Ni(xbsms)RuCp(L)][PF(6)] (H(2)xbsms = 1,2-bis(4-mercapto-3,3-dimethyl-2-thiabutyl)benzene; Cp(-) = cyclopentadienyl; L = DMSO, CO, PPh(3), and PCy(3)) are reported and are bioinspired mimics of NiFe hydrogenases. These compounds were characterized by X-ray diffraction techniques and display novel structural motifs. Interestingly, [Ni(xbsms)RuCpCO][PF(6)] is stereochemically nonrigid in solution and an isomerization mechanism was derived with the help of density functional theory (DFT) calculations. Because of an increased electron density on the metal centers [Eur. J. Inorg. Chem. 2007, 18, 2613-2626] with respect to the previously described [Ni(xbsms)Ru(CO)(2)Cl(2)] and [Ni(xbsms)Ru(p-cymene)Cl](+) complexes, [Ni(xbsms)RuCp(dmso)][PF(6)] catalyzes hydrogen evolution from Et(3)NH(+) in DMF with an overpotential reduced by 180 mV and thus represents the most efficient NiFe hydrogenase functional mimic. DFT calculations were carried out with several methods to investigate the catalytic cycle and, coupled with electrochemical measurements, allowed a mechanism to be proposed. A terminal or bridging hydride derivative was identified as the active intermediate, with the structure of the bridging form similar to that of the Ni-C active state of NiFe hydrogenases.

GC-MS Analysis: In Vivo Hepatoprotective and Antioxidant Activities of the Essential Oil of Achillea biebersteinii Afan. Growing in Saudi Arabia.

PubMed

Al-Said, Mansour S; Mothana, Ramzi A; Al-Yahya, Mohammed M; Rafatullah, Syed; Al-Sohaibani, Mohammed O; Khaled, Jamal M; Alatar, Abdulrahman; Alharbi, Naiyf S; Kurkcuoglu, Mine; Baser, Husnu C

2016-01-01

Liver disease is a worldwide problem. It represents one of the main causes of morbidity and mortality in humans. Achillea biebersteinii is used as herbal remedy for various ailments including liver diseases. But the scientific basis for its medicinal use remains unknown. Thus, this research was undertaken to evaluate the efficiency of A. biebersteinii essential oil (ABEO) (0.2 mL/kg) in the amelioration of CCl4-induced hepatotoxicity in rodent model. Moreover, the chemical content of the oil was investigated using GC and GC-MS. The following biochemical parameters were evaluated: serum glutamic oxaloacetic transaminase (GOT), glutamic-pyruvic transaminase (GPT), gamma-glutamyl-transpeptidase (γ-GGT), alkaline phosphatase (ALP), and total bilirubin. Furthermore, lipid profile, malondialdehyde (MDA), nonprotein sulfhydryl (NP-SH), and total protein (TP) contents in liver tissue were estimated. 44 components (92.0%) of the total oil have been identified by GC-MS analysis where α-terpinene and p-cymene were the most abundant. The high serum enzymatic (GOT, GPT, GGT, and ALP) and bilirubin concentrations as well as the level of MDA, NP-SH, and TP contents in liver tissues were significantly reinstated towards normalization by the ABEO. Histopathological study further confirmed these findings. In addition, ABEO showed mild antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and β-carotene-linoleic acid assays.

Control of Tetranychus urticae Koch by extracts of three essential oils of chamomile, marjoram and Eucalyptus.

PubMed

Abd El-Moneim, M R Afify; Fatma, S Ali; Turky, A F

2012-01-01

To evaluate the acaricidal activity of extracts of three essential oils of chamomile, marjoram and Eucalyptus against Tetranychus urticae (T. urticae) Koch. Extracts of three essential oils of chamomile, marjoram and Eucalyptus with different concentrations (0.5%, 1.0%, 2.0%, 3.0% and 4.0%) were used to control T. urticae Koch. The results showed that chamomile (Chamomilla recutita) represented the most potent efficient acaricidal agent against Tetranychus followed by marjoram (Marjorana hortensis) and Eucalyptus. The LC50 values of chamomile, marjoram and Eucalyptus for adults were 0.65, 1.84 and 2.18, respectively and for eggs 1.17, 6.26 and 7.33, respectively. Activities of enzymes including glutathione-S-transferase, esterase (α-esterase and β-esterase) and alkaline phosphatase in susceptible mites were determined and activities of enzymes involved in the resistance of acaricides were proved. Protease enzyme was significantly decreased at LC50 of both chamomile and marjoram compared with positive control. Gas chromatography-mass spectrometer (GC-MS) proved that the major compositions of Chamomilla recutita are α-bisabolol oxide A (35.251%), and trans-β-farersene (7.758%), while the main components of Marjorana hortensis are terpinene-4-ol (23.860%), p-cymene (23.404%) and sabinene (10.904%). It can be concluded that extracts of three essential oils of chamomile, marjoram and Eucalyptus possess acaricidal activity against T. urticae.

Antifungal activity of essential oils extract from Origanum floribundum Munby, Rosmarinus officinalis L. and Thymus ciliatus Desf. against Candida albicans isolated from bovine clinical mastitis.

PubMed

Ksouri, S; Djebir, S; Bentorki, A A; Gouri, A; Hadef, Y; Benakhla, A

2017-06-01

The aim of this study is to limit the antibiotic use in mastitis treatment and to find other alternatives. The antifungal activity of the essential oils from Origanum floribundum Munby., Rosmarinus officinalis L. and Thymus ciliatus Desf. is studied in the present work against a Candida albicans reference strain and ten C. albicans isolated strains from bovine clinical mastitis. Essential oils were extracted by hydrodistillation technique using Clevenger apparatus. Their chromatographic analysis was performed with a Gas Chromatograph/Mass Spectrometer (GC/MS). Antifungal activities of essential oils were investigated by macrobroth method of dilution in tubes to determine the Minimum Inhibitory Concentrations (MIC 80%). Analysis of the essential oil showed chemical profile dominated by thymol (50.47 and 62.41%) and P-cymene (24.22 and 15.51%) in the oregano and the thyme respectively, 1, 8-cineol (31.50%) and α-pinene (18.33%) in Rosemary. The three essential oils revealed highly effective anticandidal activity, with an MIC of 80% values ranged from 15.02 to 31.08μg/mL. These results suggest that essential oils studied can be real alternatives in the control of mastitis fungi but deserving studies more in-depth and detailed on their application in vivo. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Effect of the concentration of essential oil on orange peel waste biomethanization: Preliminary batch results.

PubMed

Calabrò, P S; Pontoni, L; Porqueddu, I; Greco, R; Pirozzi, F; Malpei, F

2016-02-01

The cultivation of orange (Citrus×sinensis) and its transformation is a major industry in many countries in the world, it leads to the production of about 25-30Mt of orange peel waste (OPW) per year. Until now many options have been proposed for the management of OPW but although they are technically feasible, in many cases their economic/environmental sustainability is questionable. This paper analyse at lab scale the possibility of using OPW as a substrate for anaerobic digestion. Specific objectives are testing the possible codigestion with municipal biowaste, verifying the effect on methane production of increasingly high concentration of orange essential oil (EO, that is well known to have antioxidant properties that can slower or either inhibit biomass activity) and obtaining information on the behaviour of d-limonene, the main EO component, during anaerobic digestion. The results indicate that OPW can produce up to about 370LnCH4/kgVS in mesophilic conditions and up to about 300LnCH4/kgVS in thermophilic conditions. The presence of increasingly high concentrations of EO temporary inhibits methanogenesis, but according to the results of batch tests, methane production restarts while d-limonene is partially degraded through a pathway that requires its conversion into p-cymene as the main intermediate. Copyright © 2015 Elsevier Ltd. 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.

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.

Antifungal Activity of Essential Oil of Eucalyptus camaldulensis Dehnh. against Selected Fusarium spp.

PubMed Central

Maina, Angeline W.; Wagacha, John M.

2017-01-01

The objective of this study was to evaluate the antifungal activity of essential oil (EO) of Eucalyptus camaldulensis Dehnh. against five Fusarium spp. commonly associated with maize. The essential oil had been extracted by steam distillation in a modified Clevenger-type apparatus from leaves of E. camaldulensis and their chemical composition characterized by gas chromatography mass spectrometry. Poisoned food technique was used to determine the percentage inhibition of mycelial growth, minimum inhibitory concentration, and minimum fungicidal concentration of the EO on the test pathogens. Antifungal activity of different concentrations of the EO was evaluated using disc diffusion method. The most abundant compounds identified in the EO were 1,8-cineole (16.2%), α-pinene (15.6%), α-phellandrene (10.0%), and p-cymene (8.1%). The EO produced complete mycelial growth inhibition in all the test pathogens at a concentration of 7-8 μL/mL after five days of incubation. The minimum inhibitory concentration and minimum fungicidal concentration of the EO on the test fungi were in the range of 7-8 μL/mL and 8–10 μL/mL, respectively. These findings confirm the fungicidal properties of E. camaldulensis essential oils and their potential use in the management of economically important Fusarium spp. and as possible alternatives to synthetic fungicides. PMID:28127308

Main compounds responsible for off-odour of strawberries infected by Phytophthora cactorum.

PubMed

Jeleń, H H; Krawczyk, J; Larsen, T O; Jarosz, A; Gołebniak, B

2005-01-01

Volatile compounds present in strawberries infected with Phytophthora cactorum, especially those responsible for the characteristic off-odour of such fruits were the subject of this study. Six strawberry varieties (Redgauntlet, Selva, Korona, Tenira, Real, Pegasus) inoculated with P. cactorum strain (PC-5), isolated from naturally infected fruit and one variety inoculated with 15 strains of P. cactorum in the laboratory were analysed. All the samples had a distinct, to a various degree, off-odour reminiscent of watercolour paint with phenolic notes. Volatile compounds were isolated by solid phase microextraction and simultaneous distillation extraction methods. To detect compounds responsible for the characteristic off-odour, gas chromatography-olfactometry was used. Two compounds were found to be responsible for the characteristic off-odour of strawberries infected by P. cactorum: 4-ethyl phenol and 4-ethyl-2-metoxy phenol (4-ethyl guaiacol). The content of these compounds in infected varieties ranged from 1.12 to 22.56 mg kg(-1) and 0.14-1.05 mg kg(-1) respectively. Other volatile compounds, not detected in noninoculated sound strawberries, were also identified: camphene, 1-octene-3-ol, 3-octanone, o-cymene, phenyl methanol, cis-linaloloxide, nonanal, phenyl ethyl alcohol, 2-undecanone and alpha-muurolene. Volatile compounds responsible for the characteristic off-odour of strawberries infected with P. cactorum were identified. Also compounds produced as a result of P. cactorum growth on strawberry fruit were characterized.

Volatile Profile of Raw Lamb Meat Stored at 4 ± 1 °C: The Potential of Specific Aldehyde Ratios as Indicators of Lamb Meat Quality

PubMed Central

2018-01-01

The objectives of the present study were: (a) to evaluate the aroma evolution of raw lamb packaged in multi-layer coating film and stored at 4 ± 1 °C, with respect to storage time and (b) to investigate whether specific aldehyde ratios could serve as markers of lamb meat freshness and degree of oxidation. Volatile compounds were determined using headspace solid phase microextraction coupled to gas chromatography/mass spectrometry. Results showed that the most dominant volatiles were 2,2,4,6,6-pentamethyl-heptane, hexanal, 1-octen-3-ol, 1-hexanol, carbon disulfide and p-cymene. Volatile compound content was increased during storage time. However, statistically significant differences were recorded only for hexanal, heptanal, and nonanal (p < 0.05). Additionally, the evolution of aldehydes during storage recorded a positive Pearson’s correlation (r) (p < 0.05), whereas hexanal to nonanal, heptanal to nonanal, octanal to nonanal ratios, along with the sum of aldehydes to nonanal ratio, were positively correlated (r = 0.83–1.00) with the degree of oxidation (mg malonic dialdehyde per kg of lamb meat). A perfect Pearson’s correlation (r = 1) was obtained for the ratio hexanal to nonanal. Therefore, this ratio is proposed as an indicator of lamb meat freshness and overall quality. PMID:29547528

Chemical Diversity, Biological Activity, and Genetic Aspects of Three Ocotea Species from the Amazon

PubMed Central

da Silva, Joyce Kelly; da Trindade, Rafaela; Moreira, Edith Cibelle; Maia, José Guilherme S.; Dosoky, Noura S.; Miller, Rebecca S.; Cseke, Leland J.; Setzer, William N.

2017-01-01

Ocotea species present economic importance and biological activities attributed to their essential oils (EOs) and extracts. For this reason, various strategies have been developed for their conservation. The chemical compositions of the essential oils and matK DNA sequences of O. caudata, O. cujumary, and O. caniculata were subjected to comparison with data from O. floribunda, O. veraguensis, and O. whitei, previously reported. The multivariate analysis of chemical composition classified the EOs into two main clusters. Group I was characterized by the presence of α-pinene (9.8–22.5%) and β-pinene (9.7–21.3%) and it includes O. caudata, O. whitei, and O. floribunda. In group II, the oils of O. cujumary and O. caniculata showed high similarity due amounts of β-caryophyllene (22.2% and 18.9%, respectively). The EO of O. veraguensis, rich in p-cymene (19.8%), showed minor similarity among all samples. The oils displayed promising antimicrobial and cytotoxic activities against Escherichia coli (minimum inhibitory concentration (MIC) < 19.5 µg·mL−1) and MCF-7 cells (median inhibitory concentration (IC50) ≅ 65.0 µg·mL−1), respectively. The analysis of matK gene displayed a good correlation with the main class of chemical compounds present in the EOs. However, the matK gene data did not show correlation with specific compounds. PMID:28524091

Quality evaluation of terpinen-4-ol-type Australian tea tree oils and commercial products: an integrated approach using conventional and chiral GC/MS combined with chemometrics.

PubMed

Wang, Mei; Zhao, Jianping; Avula, Bharathi; Wang, Yan-Hong; Chittiboyina, Amar G; Parcher, Jon F; Khan, Ikhlas A

2015-03-18

GC/MS, chiral GC/MS, and chemometric techniques were used to evaluate a large set (n=104) of tea tree oils (TTO) and commercial products purported to contain TTO. Twenty terpenoids were determined in each sample and compared with the standards specified by ISO-4730-2004. Several of the oil samples that were ISO compliant when distilled did not meet the ISO standards in this study primarily due to the presence of excessive p-cymene and/or depletion of terpinenes. Forty-nine percent of the commercial products did not meet the ISO specifications. Four terpenes, viz., α-pinene, limonene, terpinen-4-ol, and α-terpineol, present in TTOs with the (+)-isomer predominant were measured by chiral GC/MS. The results clearly indicated that 28 commercial products contained excessive (+)-isomer or contained the (+)-isomer in concentrations below the norm. Of the 28 outliers, 7 met the ISO standards. There was a substantial subset of commercial products that met ISO standards but displayed unusual enantiomeric+/-ratios. A class predictive model based on the oils that met ISO standards was constructed. The outliers identified by the class predictive model coincided with the samples that displayed an abnormal chiral ratio. Thus, chiral and chemometric analyses could be used to confirm the identification of abnormal commercial products including those that met all of the ISO standards.

Antimicrobial activity of basil (Ocimum basilicum) oil against Salmonella enteritidis in vitro and in food.

PubMed

Rattanachaikunsopon, Pongsak; Phumkhachorn, Parichat

2010-01-01

Nine essential oils were examined for antimicrobial activity against reference and clinical strains of Salmonella Enteritidis. Based on the size of the inhibition zone and the minimal inhibitory concentration, basil oil had the strongest antimicrobial activity against all the tested bacteria, and S. Enteritidis SE3 was the most sensitive strain to all the tested oils. Gas chromatography/mass spectrometry analysis revealed that the major constituents of the oil were linalool (64.35%), 1,8-cineole (12.28%), eugenol (3.21%), germacrene D (2.07%), alpha-terpineol (1.64%), and rho-cymene (1.03%). When applied in nham, a fermented pork sausage, experimentally inoculated with S. Enteritidis SE3 and stored at 4 degrees C, basil oil inhibited the bacterium in a dose-dependent fashion. Basil oil at a concentration of 50 ppm reduced the number of bacteria in the food from 5 to 2log cfu/g after storage for 3 d. An unmeasurable level of the bacterium in the food was observed at days 2 and 3 of storage when 100 and 150 ppm of basil oil was used, respectively. Sensory evaluation suggested that the addition of 100 but not of 150 ppm to nham would be acceptable to consumers. The results from this study confirm the potential use of basil oil as an antimicrobial agent to control S. Enteritidis in food.

Analysis of volatile secondary metabolites from Colombian Xylopia aromatica (Lamarck) by different extraction and headspace methods and gas chromatography.

PubMed

Stashenko, Elena E; Jaramillo, Beatriz E; Martínez, Jairo René

2004-01-30

Hydrodistillation (HD), simultaneous distillation-solvent extraction (SDE), microwave-assisted hydrodistillation (MWHD), and supercritical fluid (CO2) extraction (SFE), were employed to isolate volatile secondary metabolites from Colombian Xylopia aromatica (Lamarck) fruits. Static headspace (S-HS), simultaneous purge and trap (P&T) in solvent (CH2Cl2), and headspace (HS) solid-phase microextraction (SPME) were utilised to obtain volatile fractions from fruits of X. aromatica trees, which grow wild in Central and South America, and are abundant in Colombia. Kováts indices, mass spectra or standard compounds, were used to identify more than 50 individual components in the various volatile fractions. beta-Phellandrene was the main component found in the HD and MWHD essential oils, SDE and SFE extracts (61, 65, 57, and ca. 40%, respectively), followed by beta-myrcene (9.1, 9.3, 8.2 and 5.1%), and alpha-pinene (8.1, 7.3, 8.1 and 5.9%). The main components present in the volatile fractions of the X. aromatica fruits, isolated by S-HS, P&T and HS-SPME were beta-phellandrene (53.8, 35.7 and 39%), beta-myrcene (13.3, 12.3 and 10.1%), p-mentha-1(7),8-diene (7.1, 10.6 and 10.4%), alpha-phellandrene (2.2, 5.0 and 6.4%), and p-cymene (2.2,4.7 and 4.4%), respectively.

Changes of Peel Essential Oil Composition of Four Tunisian Citrus during Fruit Maturation

PubMed Central

Bourgou, Soumaya; Rahali, Fatma Zohra; Ourghemmi, Iness; Saïdani Tounsi, Moufida

2012-01-01

The present work investigates the effect of ripening stage on the chemical composition of essential oil extracted from peel of four citrus: bitter orange (Citrus aurantium), lemon (Citrus limon), orange maltaise (Citrus sinensis), and mandarin (Citrus reticulate) and on their antibacterial activity. Essential oils yields varied during ripening from 0.46 to 2.70%, where mandarin was found to be the richest. Forty volatile compounds were identified. Limonene (67.90–90.95%) and 1,8-cineole (tr-14.72%) were the most represented compounds in bitter orange oil while limonene (37.63–69.71%), β-pinene (0.63–31.49%), γ-terpinene (0.04–9.96%), and p-cymene (0.23–9.84%) were the highest ones in lemon. In the case of mandarin, the predominant compounds were limonene (51.81–69.00%), 1,8-cineole (0.01–26.43%), and γ-terpinene (2.53–14.06%). However, results showed that orange peel oil was dominated mainly by limonene (81.52–86.43%) during ripening. The results showed that ripening stage influenced significantly the antibacterial activity of the oils against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. This knowledge could help establish the optimum harvest date ensuring the maximum essential oil, limonene, as well as antibacterial compounds yields of citrus. PMID:22645427

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.

Short communication: Cheese supplemented with Thymus algeriensis oil, a potential natural food preservative.

PubMed

Bukvicki, Danka; Giweli, Abdulhmid; Stojkovic, Dejan; Vujisic, Ljubodrag; Tesevic, Vele; Nikolic, Milos; Sokovic, Marina; Marin, Petar D

2018-05-01

The essential oil of Thymus algeriensis was analyzed as a potential preservative in soft cheese. We developed a novel method to test the preserving properties of essential oil in soft cheese. Contamination incidence of Penicillium aurantiogriseum was absent after 30 d of storage at 4°C with 25 µL of essential oil added. The antimicrobial activity was tested against 8 bacteria and 8 fungi. Thymus algeriensis oil showed inhibitory activity against tested bacteria at 0.03 to 0.09 mg/mL, and bactericidal activity was achieved at 0.05 to 0.15 mg/mL. For antifungal activity, minimum inhibitory concentrations ranged between 0.01 and 0.04 mg/mL and minimum fungicidal concentrations between 0.01 and 0.04 mg/mL. Furthermore, the oil was also screened for antiradical activity using the 1,1-diphenyl-2-picrylhydrazyl assay. The results showed that the oil was active and achieved half-maximal inhibitory activity at 0.132 mg/mL. We used gas chromatography, gas chromatography-mass spectrometry, and nuclear magnetic resonance spectrometry to investigate the volatile compounds from the oil. Carvacrol was identified as the main compound in the oil, represented by 80.9% of the total constituents, followed by p-cymene (7.7%). Copyright © 2018 American Dairy Science Association. Published by Elsevier Inc. All rights reserved.

Hydrodistillation extraction time effect on essential oil yield, composition, and bioactivity of coriander oil.

PubMed

Zheljazkov, Valtcho D; Astatkie, Tess; Schlegel, Vicki

2014-01-01

Coriander (Coriandrum sativum L.) is a major essential oil crop grown throughout the world. Coriander essential oil is extracted from coriander fruits via hydrodistillation, with the industry using 180-240 min of distillation time (DT), but the optimum DT for maximizing essential oil yield, composition of constituents, and antioxidant activities are not known. This research was conducted to determine the effect of DT on coriander oil yield, composition, and bioactivity. The results show that essential oil yield at the shorter DT was low and generally increased with increasing DT with the maximum yields achieved at DT between 40 and 160 min. The concentrations of the low-boiling point essential oil constituents: α-pinene, camphene, β-pinene, myrcene, para-cymene, limonene, and γ-terpinene were higher at shorter DT (< 2.5 min) and decreased with increasing DT; but the trend reversed for the high-boiling point constituents: geraniol and geranyl-acetate. The concentration of the major essential oil constituent, linalool, was 51% at DT 1.15 min, and increased steadily to 68% with increasing DT. In conclusion, 40 min DT is sufficient to maximize yield of essential oil; and different DT can be used to obtain essential oil with differential composition. Its antioxidant capacity was affected by the DT, with 20 and 240 min DT showing higher antioxidant activity. Comparisons of coriander essential oil composition must consider the length of the DT.

Osmium Atoms and Os2 Molecules Move Faster on Selenium-Doped Compared to Sulfur-Doped Boronic Graphenic Surfaces

PubMed Central

2015-01-01

We deposited Os atoms on S- and Se-doped boronic graphenic surfaces by electron bombardment of micelles containing 16e complexes [Os(p-cymene)(1,2-dicarba-closo-dodecarborane-1,2-diselenate/dithiolate)] encapsulated in a triblock copolymer. The surfaces were characterized by energy-dispersive X-ray (EDX) analysis and electron energy loss spectroscopy of energy filtered TEM (EFTEM). Os atoms moved ca. 26× faster on the B/Se surface compared to the B/S surface (233 ± 34 pm·s–1versus 8.9 ± 1.9 pm·s–1). Os atoms formed dimers with an average Os–Os distance of 0.284 ± 0.077 nm on the B/Se surface and 0.243 ± 0.059 nm on B/S, close to that in metallic Os. The Os2 molecules moved 0.83× and 0.65× more slowly than single Os atoms on B/S and B/Se surfaces, respectively, and again markedly faster (ca. 20×) on the B/Se surface (151 ± 45 pm·s–1 versus 7.4 ± 2.8 pm·s–1). Os atom motion did not follow Brownian motion and appears to involve anchoring sites, probably S and Se atoms. The ability to control the atomic motion of metal atoms and molecules on surfaces has potential for exploitation in nanodevices of the future. PMID:26525180

Variability of Pinus halepensis Mill. Essential Oils and Their Antioxidant Activities Depending on the Stage of Growth During Vegetative Cycle.

PubMed

Djerrad, Zineb; Djouahri, Abderrahmane; Kadik, Leila

2017-04-01

The impact of growth stages during vegetative cycle (B 0  - B 5 ) on chemical composition and antioxidant activities of Pinus halepensis Mill. needles essential oils was investigated for the first time. GC and GC/MS analyses pointed to a quantitative variability of components; terpene hydrocarbons derivatives, represented by α-pinene (8.5 - 12.9%), myrcene (17.5 - 21.6%), p-cymene (7.9 - 11.9%) and (Z)-β-caryophyllene (17.3 - 21.2%) as major components, decreased from 88.9% at B 0 growth stage to 66.9% at B 5 growth stage, whereas oxygenated derivatives, represented by caryophyllene oxide (5.4 - 12.6%) and terpinen-4-ol (0.4 - 3.3%) as major components, increased from 7% at B 0 growth stage to 28.4% at B 5 growth stage. Furthermore, our findings showed that essential oil of P. halepensis needles collected at B 5 growth stage possess higher antioxidant activities by four different testing systems than those collected at B 0  - B 4 growth stages. This highlighted variability led to conclude that we should select essential oils to be investigated carefully depending on growth stage, in order to have the highest effectiveness of essential oil in terms of biological activities for human health purposes. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

Lavender (Lavandula stoechas L.) essential oils attenuate hyperglycemia and protect against oxidative stress in alloxan-induced diabetic rats

PubMed Central

2013-01-01

Background The present study described the phytochemical profile of Lavandula stoechas essential oils, collected in the area of Ain-Draham (North-West of Tunisia), as well as their protective effects against alloxan-induced diabetes and oxidative stress in rat. Methods Essential oils samples were obtained from the aerial parts of the plant by hydrodistillation and analyzed by GC–MS. Rats were divided into four groups: Healthy Control (HC); Diabetic Control (DC); Healthy + Essential Oils (H + EO) and Diabetic + Essential Oils (D + EO). Antidiabetic and antioxidant activities were evaluated after subacute intraperitoneally injection of Lavandula stoechas essential oils (50 mg/kg b.w., i.p.) to rats during 15 days. Results The principal compounds detected are: D-Fenchone (29.28%), α-pinene (23.18%), Camphor (15.97%), Camphene (7.83%), Eucapur (3.29%), Limonene, (2.71%) Linalool, (2.01%) Endobornyl Acetate (1.03%). The essential oils also contained smaller percentages of Tricyclene, Cymene, Delta-Cadinene, Selina-3,7(11)-diene. Furthermore, we found that Lavandula stoechas essential oils significantly protected against the increase of blood glucose as well as the decrease of antioxidant enzyme activities induced by aloxan treatment. Subacute essential oils treatment induced a decrease of lipoperoxidation as well as an increase of antioxidant enzyme activities. Conclusions These findings suggested that lavandula stoechas essential oils protected against diabetes and oxidative stress induced by alloxan treatment. These effects are in partly due to its potent antioxidant properties. PMID:24373672

Organometallic ruthenium anticancer complexes inhibit human glutathione-S-transferase π.

PubMed

Lin, Yu; Huang, Yongdong; Zheng, Wei; Wang, Fuyi; Habtemariam, Abraha; Luo, Qun; Li, Xianchan; Wu, Kui; Sadler, Peter J; Xiong, Shaoxiang

2013-11-01

The organometallic ruthenium(II) anticancer complexes [(η(6)-arene)Ru(en)Cl](+) (arene = p-cymene (1), biphenyl (2) or 9,10-dihydrophenanthrene (3); en = ethylenediamine), exhibit in vitro and in vivo anticancer activities. In the present work, we show that they inhibit human glutathione-S-transferase π (GSTπ) with IC50 values of 59.4 ± 1.3, 63.2 ± 0.4 and 37.2 ± 1.1 μM, respectively. Mass spectrometry revealed that complex 1 binds to the S-donors of Cys15, Cys48 within the G-site and Cys102 at the interface of the GSTπ dimer, while complex 2 binds to Cys48 and Met92 at the dimer interface and complex 3 to Cys15, Cys48 and Met92. Moreover, the binding of complex 1 to Cys15 and Cys102, complex 2 to Cys48 and complex 3 to Cys15 induces the irreversible oxidation of the coordinated thiolates to sulfenates. Molecular modeling studies indicate that the coordination of the {(arene)Ru(en)}(2+) fragment to Cys48 blocks the hydrophilic G-site sterically, perhaps preventing substrate from proper positioning and accounting for the reduction in enzymatic activity of ruthenated GSTπ. The binding of the ruthenium arene complexes to Cys102 or Met92 disrupts the dimer interface which is an essential structural feature for the proper functioning of GSTπ, perhaps also contributing to the inhibition of GSTπ. © 2013.

Down-regulatory effect of Thymus vulgaris L. on growth and Tri4 gene expression in Fusarium oxysporum strains.

PubMed

Divband, Kolsum; Shokri, Hojjatollah; Khosravi, Ali Reza

2017-03-01

The aims of this study were to evaluate the efficacy of Thymus vulgaris (T. vulgaris) essential oil on the fungal growth and Tri4 gene expression in Fusarium oxysporum (F. oxysporum) strains. The oil was obtained by water-distillation using a Clevenger-type system. The chemical composition of the essential oil was obtained by gas chromatography- mass spectroscopy (GC-MS) and by retention indices. The antifungal activity was evaluated by broth microdilution assay. A quantitative real time RT-PCR (qRT-PCR) assay was also developed specific for F. oxysporum on the basis of trichothecene biosynthetic gene, Tri4, which allowed discrimination from F. oxysporum. Results showed thymol (32.67%) and p-cymene (16.68%) as the main components of T. vulgaris. Minimum inhibitory concentration (MIC) values varied from 5 to 20 μg/ml with T. vulgaris (mean: 10.50 μg/ml), while minimum fungicidal concentration (MFC) values ranged from 8 to 30 μg/ml with mean value of 16.20 μg/ml qRT-PCR results revealed a downregulation from 4.04 to 6.27 fold of Tri4 gene expression of the fungi exposed to T. vulgaris essential oil. The results suggest that T. vulgaris oil can be considered potential alternative natural fungicide to the synthetic chemicals that are currently used to prevent and control seed-borne diseases. Copyright © 2017 Elsevier Ltd. All rights reserved.

Antifungal and antiaflatoxigenic properties of Cuminum cyminum (L.) seed essential oil and its efficacy as a preservative in stored commodities.

PubMed

Kedia, Akash; Prakash, Bhanu; Mishra, Prashant K; Dubey, N K

2014-01-03

The study reports potential of Cuminum cyminum (cumin) seed essential oil (EO) as a plant based shelf life enhancer against fungal and aflatoxin contamination and lipid peroxidation. The EO showed efficacy as a preservative in food systems (stored wheat and chickpeas). A total of 1230 fungal isolates were obtained from food samples, with Aspergillus flavus LHP(C)-D6 identified as the highest aflatoxin producer. Cumin seed EO was chemically characterized through GC-MS where cymene (47.08%) was found as the major component. The minimum inhibitory concentration and minimum aflatoxin inhibitory concentration of EO were 0.6 and 0.5 μl/ml respectively. The EO showed toxicity against a broad spectrum of food borne fungi. The antifungal action of EO on ergosterol content in the plasma membrane of A. flavus was determined. The EO showed strong antioxidant potential having IC50 0.092 μl/ml. As a fumigant in food systems, the EO provided sufficient protection of food samples against fungal association without affecting seed germination. In view of the antifungal and antiaflatoxigenic nature, free radical scavenging potential and efficacy in food system, cumin seed EO may be able to provide protection of food commodities against quantitative and qualitative losses, thereby enhancing their shelf life. The present investigation comprises the first report on antifungal mode of action of cumin seed EO and its efficacy as fumigant in food systems. © 2013.

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.

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.

Control of Tetranychus urticae Koch by extracts of three essential oils of chamomile, marjoram and Eucalyptus

PubMed Central

Abd El-Moneim, MR Afify; Fatma, S Ali; Turky, AF

2012-01-01

Objective To evaluate the acaricidal activity of extracts of three essential oils of chamomile, marjoram and Eucalyptus against Tetranychus urticae (T. urticae) Koch. Methods Extracts of three essential oils of chamomile, marjoram and Eucalyptus with different concentrations (0.5%, 1.0%, 2.0%, 3.0% and 4.0%) were used to control T. urticae Koch. Results The results showed that chamomile (Chamomilla recutita) represented the most potent efficient acaricidal agent against Tetranychus followed by marjoram (Marjorana hortensis) and Eucalyptus. The LC50 values of chamomile, marjoram and Eucalyptus for adults were 0.65, 1.84 and 2.18, respectively and for eggs 1.17, 6.26 and 7.33, respectively. Activities of enzymes including glutathione-S-transferase, esterase (α-esterase and β-esterase) and alkaline phosphatase in susceptible mites were determined and activities of enzymes involved in the resistance of acaricides were proved. Protease enzyme was significantly decreased at LC50 of both chamomile and marjoram compared with positive control. Gas chromatography-mass spectrometer (GC-MS) proved that the major compositions of Chamomilla recutita are α-bisabolol oxide A (35.251%), and trans-β-farersene (7.758%), while the main components of Marjorana hortensis are terpinene-4-ol (23.860%), p-cymene (23.404%) and sabinene (10.904%). Conclusions It can be concluded that extracts of three essential oils of chamomile, marjoram and Eucalyptus possess acaricidal activity against T. urticae. PMID:23569829

In vitro biological activity and essential oil composition of four indigenous South African Helichrysum species.

PubMed

Lourens, A C U; Reddy, D; Başer, K H C; Viljoen, A M; Van Vuuren, S F

2004-12-01

Helichrysum species are used widely to treat various medical conditions. In this study, the anti-microbial, anti-oxidant (DPPH assay) and anti-inflammatory activity (5-lipoxygenase assay) of Helichrysum dasyanthum, Helichrysum felinum, Helichrysum excisum and Helichrysum petiolare were investigated. The essential oil compositions of these species were determined. The acetone and methanol extracts as well as the essential oils exhibited activity against Gram-positive bacteria, while both the methanol and acetone extracts of all four species were active in the anti-oxidant assay. The essential oils, on the other hand, displayed activity in the 5-lipoxygenase assay, which was used as an indication of anti-inflammatory activity. Two extracts exhibited promising activity in the anti-microbial assay, the acetone extract of Helichrysum dasyanthum with a MIC value of 15.63 microg/ml and the methanol extract of Helichrysum excisum with a MIC value of 62.5 microg/ml. The acetone extract of Helichrysum dasyanthum was the most active free radical scavenger in the DPPH assay (IC(50) of 9.53 microg/ml) while values for the anti-inflammatory activity of the essential oils ranged between 25 and 32 microg/ml. The essential oil compositions of three species (Helichrysum dasyanthum, Helichrysum excisum and Helichrysum petiolare) were dominated by the presence of monoterpenes such as alpha-pinene, 1,8-cineole and p-cymene. In the oil of Helichrysum felinum, monoterpenes were largely absent. Its profile consisted of a variety of sesquiterpenes in low concentrations with beta-caryophyllene dominating.

(Tetramethylthiophene)ruthenium in dichloride dimer: A versatile synthetic intermediate in thiophene coordination chemistry

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

Lockemeyer, J.R.; Rauchfuss, T.B.; Wilson, S.R.

1989-11-22

The thermal reaction of ((cymene)RuCl{sub 2}){sub 2} and tetramethylthiophene (TMT) gives ((TMT)RuCl{sub 2}){sub 2} (1). Treatment of 1 with silver salts in the presence of various ligands gives salts of ((TMT)RuL{sub 3}){sup 2+} where L{sub 3} = (H{sub 2}O){sub 3}, (CH{sub 3}CN){sub 3}, and TMT. A crystallographic study demonstrated that ((TMT){sub 2}Ru)(BF{sub 4}){sub 2} {times} 2CH{sub 3}NO{sub 2} adopts a sandwich structure with sulfur atoms sited cis on the pseudooctahedron. Cyclic voltammetry studies show that ((TMT){sub 2}Ru){sup 2+} undergoes 2 reversible one-electron reductions. Solutions of 1 and phosphine and amine donors react to give well-behaved monometallic derivatives of the typemore » (TMT)RuCl{sub 2}L where L is PR{sub 3} and NH{sub 2}C{sub 6}H{sub 4}Me. For bulky L = PPh{sub 3} and P(C{sub 6}H{sub 4}Me){sub 3}, variable-temperature NMR studies demonstrate hindered rotation about the Ru-P and Ru{hor ellipsis} TMT axes. Treatment of 1 with (Me{sub 3}Si){sub 2}S gives the cluster ((TMT)RuCl){sub 3}S{sup +} whose PF{sub 6}{sup {minus}} salt was examined by X-ray crystallography. The cluster is comprised of 3 conjoined pseudooctahedral Ru centers bridged by 1 {mu}{sub 3}-S and 3 {mu}-Cl atoms.« less

Microwave-assisted extraction of Nigella sativa L. essential oil and evaluation of its antioxidant activity.

PubMed

Abedi, Abdol-Samad; Rismanchi, Marjan; Shahdoostkhany, Mehrnoush; Mohammadi, Abdorreza; Mortazavian, Amir Mohammad

2017-11-01

It has been previously reported that the essential oil of Nigella sativa L. seeds and its major active component, thymoquinone (TQ), possess a broad variety of biological activities and therapeutic properties. In this work, microwave-assisted extraction (MAE) of the essential oil from Nigella sativa L. seeds and its antioxidant activity were studied. Response surface methodology based on central composite design was used to evaluate the effects of extraction time, irradiation power and moisture content on extraction yield and TQ content. Optimal parameters obtained by CCD and RSM were extraction time 30 min, irradiation power 450 W, and moisture content 50%. The extraction yield and TQ content of the essential oil were 0.33 and 20% under the optimum conditions, respectively. In contrast, extraction yield and TQ amount of oil obtained by hydrodistillation (HD) were 0.23 and 3.71%, respectively. The main constituents of the essential oil extracted by MAE and HD were p -cymene, TQ, α-thujene and longifolene, comprising more than 60% of total peak area. The antioxidant capacity of essential oils extracted by different methods were evaluated using 2,2-diphenyl-1-picrylhydrazyl and Ferric reducing antioxidant power assays, and compared with traditional antioxidants. The results showed that MAE method was a viable alternative to HD for the essential oil extraction from N. sativa seeds due to the excellent extraction efficiency, higher thymoquinone content, and stronger antioxidant activity.

Lavender (Lavandula stoechas L.) essential oils attenuate hyperglycemia and protect against oxidative stress in alloxan-induced diabetic rats.

PubMed

Sebai, Hichem; Selmi, Slimen; Rtibi, Kais; Souli, Abdelaziz; Gharbi, Najoua; Sakly, Mohsen

2013-12-28

The present study described the phytochemical profile of Lavandula stoechas essential oils, collected in the area of Ain-Draham (North-West of Tunisia), as well as their protective effects against alloxan-induced diabetes and oxidative stress in rat. Essential oils samples were obtained from the aerial parts of the plant by hydrodistillation and analyzed by GC-MS. Rats were divided into four groups: Healthy Control (HC); Diabetic Control (DC); Healthy + Essential Oils (H + EO) and Diabetic + Essential Oils (D + EO).Antidiabetic and antioxidant activities were evaluated after subacute intraperitoneally injection of Lavandula stoechas essential oils (50 mg/kg b.w., i.p.) to rats during 15 days. The principal compounds detected are: D-Fenchone (29.28%), α-pinene (23.18%), Camphor (15.97%), Camphene (7.83%), Eucapur (3.29%), Limonene, (2.71%) Linalool, (2.01%) Endobornyl Acetate (1.03%). The essential oils also contained smaller percentages of Tricyclene, Cymene, Delta-Cadinene, Selina-3,7(11)-diene. Furthermore, we found that Lavandula stoechas essential oils significantly protected against the increase of blood glucose as well as the decrease of antioxidant enzyme activities induced by aloxan treatment. Subacute essential oils treatment induced a decrease of lipoperoxidation as well as an increase of antioxidant enzyme activities. These findings suggested that lavandula stoechas essential oils protected against diabetes and oxidative stress induced by alloxan treatment. These effects are in partly due to its potent antioxidant properties.

Lavandula angustifolia and Lavandula latifolia Essential Oils from Spain: Aromatic Profile and Bioactivities.

PubMed

Carrasco, Alejandro; Martinez-Gutierrez, Ramiro; Tomas, Virginia; Tudela, Jose

2016-01-01

Compositions of true lavender (Lavandula angustifolia) and spike lavender (Lavandula latifolia) essential oils, cultivated and extracted in the Southeast of Spain, were determined by gas chromatography coupled with mass spectrometry detection, obtaining both relative (peak area) and absolute (using standard curves) concentrations. Linalool (37-54 %), linalyl acetate (21-36 %) and (E)-β-caryophyllene (1-3 %) were the most abundant components for L. angustifolia. Linalool (35-51 %), eucalyptol (26-32 %), camphor (10-18 %), α-pinene (1-2 %), α-terpineol (1-2 %) and α-bisabolene (1-2 %) were the most abundant components for L. latifolia. The characterization was completed with enantioselective gas chromatography, in which the determined main molecules were (-)-linalool, (-)-linalyl acetate and (+)-camphor. (S)-(-)-camphene, (R)-(+)-limonene, (1R, 9S)-(-)-(E)-β-caryophyllene and (1R, 4R, 6R, 10S)-(-)-caryophyllene oxide were found in this study as the predominant enantiomers in Spanish L. angustifolia. The characterised essential oils were tested for their antioxidant activity against free radicals ABTS, DPPH, ORAC, chelating, and reducing power. Inhibitory activity on lipoxygenase was observed indicating a possible anti-inflammatory activity, mainly due to linalool, camphor, p-cymene and limonene. These results can be the starting point for a future study of the potential use of L. angustifolia and L. latifolia essential oils as natural cosmetic and natural pharmaceutical ingredients for several skin diseases. Georg Thieme Verlag KG Stuttgart · New York.

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

A novel ruthenium (II)-derived organometallic compound, TQ-6, potently inhibits platelet aggregation: Ex vivo and in vivo studies.

PubMed

Hsia, Chih-Hsuan; Velusamy, Marappan; Sheu, Joen-Rong; Khamrang, Themmila; Jayakumar, Thanasekaran; Lu, Wan-Jung; Lin, Kuan-Hung; Chang, Chao-Chien

2017-08-25

Arterial thrombosis plays a key role in cardiovascular diseases. Hence, developing more effective antithrombotic agents is necessary. We designed a ruthenium (II)-derived complex, [Ru(η 6 -cymene)2-(1H-benzoimidazol-2-yl)-quinoline Cl]BF 4 (TQ-6), as a new antiplatelet drug. TQ-6 (0.3 µM) exhibited extremely strong inhibitory activity against platelet aggregation, Src, and Syk phosphorylation stimulated by agonists in human platelets. In collagen-activated platelets, TQ-6 also inhibited ATP-release, [Ca +2 ]i, P-selectin expression, FITC-PAC-1 binding, and hydroxyl radical formation, as well as the phosphorylation of phospholipase Cγ2, protein kinase C, mitogen-activated protein kinases, and Akt. Neither FITC-JAQ1 nor FITC-triflavin binding or integrin β 3 phosphorylation stimulated by immobilized fibrinogen were diminished by TQ-6. Furthermore, TQ-6 had no effects in cyclic nucleotide formation. Moreover, TQ-6 substantially prolonged the closure time in whole blood, increased the occlusion time of thrombotic platelet plug formation and bleeding time in mice. In conclusion, TQ-6 has a novel role in inhibiting platelet activation through the inhibition of the agonist receptors-mediated inside-out signaling such as Src-Syk-PLCγ2 cascade and subsequent suppression of granule secretion, leading to disturb integrin α IIb β 3 -mediated outside-in signaling, and ultimately inhibiting platelet aggregation. Therefore, TQ-6 has potential to develop as a therapeutic agent for preventing or treating thromboembolic disorders.

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.

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.

Volatile organic compounds and isoprene oxidation products at a temperate deciduous forest site

NASA Astrophysics Data System (ADS)

Helmig, Detlev; Greenberg, Jim; Guenther, Alex; Zimmerman, Pat; Geron, Chris

1998-09-01

Biogenic volatile organic compounds (BVOCs) and their role in atmospheric oxidant formation were investigated at a forest site near Oak Ridge, Tennessee, as part of the Nashville Southern Oxidants Study (SOS) in July 1995. Of 98 VOCs detected, a major fraction were anthropogenic VOCs such as chlorofluorocarbons (CFCs), alkanes, alkenes and aromatic compounds. Isoprene was the dominant BVOC during daytime. Primary products from BVOC oxidation were methylvinylketone, methacrolein and 3-methylfuran. Other compounds studied include the BVOCs α-pinene, camphene, β-pinene, p-cymene, limonene and cis-3-hexenyl acetate and a series of light alkanes, aromatic hydrocarbons and seven of the CFCs. The correlation of meteorological parameters, with the mixing ratios of these different compounds, reveals information on atmospheric oxidation processes and transport. Long-lived VOCs show very steady mixing ratio time series. Regionally and anthropogenically emitted VOCs display distinct diurnal cycles with a strong mixing ratio decrease in the morning from the breakup of the nocturnal boundary layer. Nighttime mixing ratio increases of CFCs and anthropogenic VOCs are suspected to derive from emissions within the Knoxville urban area into the shallow nocturnal boundary layer. In contrast, the time series of BVOCs and their oxidation products are determined by a combination of emission control, atmospheric oxidation and deposition, and boundary layer dynamics. Mixing ratio time series data for monoterpenes and cis-3-hexenyl acetate suggest a temporarily emission rate increase during and after heavy rain events. The isoprene oxidation products demonstrate differences in the oxidation pathways during night and day and in their dry and wet deposition rates.

Characterisation of volatile organic compounds (VOCs) released by the composting of different waste matrices.

PubMed

Schiavon, Marco; Martini, Luca Matteo; Corrà, Cesare; Scapinello, Marco; Coller, Graziano; Tosi, Paolo; Ragazzi, Marco

2017-12-01

The complaints arising from the problem of odorants released by composting plants may impede the construction of new composting facilities, preclude the proper activity of existing facilities or even lead to their closure, with negative implications for waste management and local economy. Improving the knowledge on VOC emissions from composting processes is of particular importance since different VOCs imply different odour impacts. To this purpose, three different organic matrices were studied in this work: dewatered sewage sludge (M1), digested organic fraction of municipal solid waste (M2) and untreated food waste (M3). The three matrices were aerobically biodegraded in a bench-scale bioreactor simulating composting conditions. A homemade device sampled the process air from each treatment at defined time intervals. The samples were analysed for VOC detection. The information on the concentrations of the detected VOCs was combined with the VOC-specific odour thresholds to estimate the relative weight of each biodegraded matrix in terms of odour impact. When the odour formation was at its maximum, the waste gas from the composting of M3 showed a total odour concentration about 60 and 15,000 times higher than those resulting from the composting of M1 and M2, respectively. Ethyl isovalerate showed the highest contribution to the total odour concentration (>99%). Terpenes (α-pinene, β-pinene, p-cymene and limonene) were abundantly present in M2 and M3, while sulphides (dimethyl sulphide and dimethyl disulphide) were the dominant components of M1. Copyright © 2017 Elsevier Ltd. All rights reserved.

Coupling limonene formation and oxyfunctionalization by mixed-culture resting cell fermentation.

PubMed

Willrodt, Christian; Hoschek, Anna; Bühler, Bruno; Schmid, Andreas; Julsing, Mattijs K

2015-09-01

Metabolic engineering strategies mark a milestone for the fermentative production of bulk and fine chemicals. Yet, toxic products and volatile reaction intermediates with low solubilities remain challenging. Prominent examples are artificial multistep pathways like the production of perillyl acetate (POHAc) from glucose via limonene. For POHAc, these limitations can be overcome by mixed-culture fermentations. A limonene biosynthesis pathway and cytochrome P450 153A6 (CYP153A6) as regioselective hydroxylase are used in two distinct recombinant E. coli. POHAc formation from glucose in one recombinant cell was hindered by ineffective coupling of limonene synthesis and low rates of oxyfunctionalization. The optimization of P450 gene expression led to the formation of 6.20 ± 0.06 mg gcdw (-1) POHAc in a biphasic batch cultivation with glucose as sole carbon and energy source. Increasing the spatial proximity between limonene synthase and CYP153A6 by a genetic fusion of both enzymes changed the molar limonene/POHAc ratio from 3.2 to 1.6. Spatial separation of limonene biosynthesis from its oxyfunctionalization improved POHAc concentration 3.3-fold to 21.7 mg L(-1) as compared to a biphasic fermentation. Mixed-cultures of E. coli BL21 (DE3) containing the limonene biosynthesis pathway and E. coli MG1655 harboring either CYP153A6, or alternatively a cymene monooxygenase, showed POHAc formation rates of 0.06 or 0.11 U gcdw (-1) , respectively. This concept provides a novel framework for fermentative syntheses involving toxic, volatile, or barely soluble compounds or pathway intermediates. © 2015 Wiley Periodicals, Inc.

Chemical Composition, Antioxidant and Biological Activities of the Essential Oil and Extract of the Seeds of Glycine max (Soybean) from North Iran.

PubMed

Ghahari, Somayeh; Alinezhad, Heshmatollah; Nematzadeh, Ghorban Ali; Tajbakhsh, Mahmood; Baharfar, Robabeh

2017-04-01

Glycine max (L.) Merrill (soybean) is a major leguminous crop, cultivated globally as well as in Iran. This study examines the chemical composition of soybean essential oil, and evaluates the antioxidant and antimicrobial activities of seeds on various plant pathogens that commonly cause irreparable damages to agricultural crops. The essential oil of soybean seeds was analyzed by gas chromatography coupled to mass spectrometry. Antimicrobial activity was tested against 14 microorganisms, including three gram-positive, five gram-negative bacteria, and six fungi, using disk diffusion method and the Minimum Inhibitory Concentration technique. The soybean seeds were also subjected to screening for possible antioxidant activity by using catalase, peroxidase, superoxide dismutase, and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. Forty components were identified, representing 96.68% of the total oil. The major constituents of the oil were carvacrol (13.44%), (E,E)-2,4-decadienal (9.15%), p-allylanisole (5.65%), p-cymene (4.87%), and limonene (4.75%). The oil showed significant activity against Pseudomonas syringae subsp. syringae, Rathayibacter toxicus with MIC = 25 µg/mL, and Pyricularia oryzae with MIC = 12.5 µg/mL. In addition, the free radical scavenging capacity of the essential oil was determined with an IC 50 value of 162.35 µg/mL. Our results suggest that this plant may be a potential source of biocide, for economical and environmentally friendly disease control strategies. It may also be a good candidate for further biological and pharmacological investigations.

Generation of sub-ppb level vapor phase mixtures of biogenic volatile organic compounds from liquid phase standards and stepwise characterization of their volatilization properties by thermal desorption-gas chromatography-mass spectrometry.

PubMed

Iqbal, Mohammad Asif; Kim, Ki-Hyun

2014-12-19

In the analysis of biogenic volatile organic compounds (BVOCs) in ambient air, preparation of a sub-ppb level standard is an important factor. This task is very challenging as most BVOCs (e.g., monoterpenes) are highly volatile and reactive in nature. As a means to produce sub-ppb gaseous standards for BVOCs, we investigated the dynamic headspace (HS) extraction technique through which their vapors are generated from a liquid standard (mixture of 10 BVOCs: (1) α-pinene, (2) β-pinene, (3) 3-carene, (4) myrcene, (5) α-phellandrene, (6) α-terpinene, (7) R-limonene, (8) γ-terpinene, (9) p-cymene, and (10) Camphene) spiked into a chamber-style impinger. The quantification of BVOCs was made by collection on multiple-bed sorbent tubes (STs) and subsequent analysis by thermal desorption-gas chromatography-mass spectrometry (TD-GC-MS). Using this approach, sub-ppb level mixtures of gaseous BVOCs were generated at different sweep cycles. The mean concentrations of 10 BVOCs generated from the most stable conditions (i.e., in the third sweep cycle) varied in the range of 0.37±0.05 to 7.27±0.86ppb depending on the initial concentration of liquid standard spiked into the system. The reproducibility of the gaseous BVOCs generated as mixture standards, if expressed in terms of relative standard error using the concentration datasets acquired under stable conditions, ranged from 1.64 (α-phellandrene) to 9.67% (R-limonene). Copyright © 2014 Elsevier B.V. All rights reserved.

Repellent and Larvicidal Activity of the Essential Oil From Eucalyptus nitens Against Aedes aegypti and Aedes albopictus (Diptera: Culicidae).

PubMed

Alvarez Costa, Agustín; Naspi, Cecilia V; Lucia, Alejandro; Masuh, Héctor M

2017-05-01

Dengue, chikungunya, and yellow fever are important vector-borne diseases transmitted by female mosquitoes when they feed on humans. The use of repellents based on natural products is an alternative for personal protection against these diseases. Application of chemicals with larvicidal activity is another strategy for controlling the mosquito population. The repellent and larvicidal activities of the essential oil from Eucalyptus nitens were tested against Aedes aegypti and Aedes albopictus, the main vectors of these arboviruses. The essential oil was extracted by hydrodistillation and then analyzed by gas chromatography-mass spectrometry. The main components of Eucalyptus nitens essential oil were found to be terpenes such as 1,8-cineole and p-cymene, followed by β-triketones and alkyl esters. The repellent activity of the essential oil against both species was significantly higher when compared with the main component, 1,8-cineole, alone. These results indicate that the repellent effect of E. nitens is not due only to the main component, 1,8-cineole, but also that other compounds may be responsible. Aedes aegypti was found to be more tolerant to the essential oil larvicidal effects than Ae. albopictus (Ae. aegypti LC50 = 52.83 ppm, Ae. albopictus LC 50 = 28.19 ppm). The repellent and larvicidal activity could be associated to the presence of cyclic β-triketones such as flavesone, leptospermone, and isoleptospermone. © 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 oil composition and antibacterial activity of Origanum vulgare subsp. glandulosum Desf. at different phenological stages.

PubMed

Béjaoui, Afef; Chaabane, Hédia; Jemli, Maroua; Boulila, Abdennacer; Boussaid, Mohamed

2013-12-01

Variation in the quantity and quality of the essential oil (EO) of wild population of Origanum vulgare at different phenological stages, including vegetative, late vegetative, and flowering set, is reported. The oils of air-dried samples were obtained by hydrodistillation. The yield of oils (w/w%) at different stages were in the order of late vegetative (2.0%), early vegetative (1.7%), and flowering (0.6%) set. The oils were analyzed by gas chromatography (GC) and GC-mass spectrometry (GC-MS). In total, 36, 33, and 16 components were identified and quantified in vegetative, late vegetative, and flowering set, representing 94.47%, 95.91%, and 99.62% of the oil, respectively. Carvacrol was the major compound in all samples. The ranges of major constituents were as follows: carvacrol (61.08-83.37%), p-cymene (3.02-9.87%), and γ-terpinene (4.13-6.34%). Antibacterial activity of the oils was tested against three Gram-positive and two Gram-negative bacteria by the disc diffusion method and determining their diameter of inhibition and the minimum inhibitory concentration (MIC) values. The inhibition zones and MIC values for bacterial strains, which were sensitive to the EO of O. vulgare subsp. glandulosum, were in the range of 9-36 mm and 125-600 μg/mL, respectively. The oils of various phenological stages showed high activity against all tested bacteria, of which Bacillus subtilis was the most sensitive and resistant strain, respectively. Thus, they represent an inexpensive source of natural antibacterial substances that exhibited potential for use in pathogenic systems.

Ferrocene and (arene)ruthenium(II) complexes of the natural anticancer naphthoquinone plumbagin with enhanced efficacy against resistant cancer cells and a genuine mode of action.

PubMed

Spoerlein-Guettler, Cornelia; Mahal, Katharina; Schobert, Rainer; Biersack, Bernhard

2014-09-01

A series of ferrocene and (arene)ruthenium(II) complexes attached to the naturally occurring anticancer naphthoquinones plumbagin and juglone was tested for efficacy against various cancer cell lines and for alterations in the mode of action. The plumbagin ferrocene and (p-cymene)Ru(II) conjugates 1c and 2a overcame the multi-drug drug resistance of KB-V1/Vbl cervix carcinoma cells and showed IC50 (72 h) values around 1 μM in growth inhibition assays using 3-(4,5-dimethyl-2-yl)-2,5-diphenyltetrazolium bromide (MTT). They were further investigated for their influence on the cell cycle of KB-V1/Vbl and HCT-116 colon carcinoma cells, on the generation of reactive oxygen species (ROS) by the latter cell line, for their substrate character for the P-glycoprotein drug eflux pump via the calcein-AM efflux assays, and for DNA affinity by the electrophoretic mobility shift assay (EMSA). The derivatives 1c and 2a increased the number of dead cancer cells (sub-G0/G1 fraction) in a dose- and time-dependent manner. ROS levels were significantly increased upon treatment with 1c and 2a. These compounds also showed a greater affinity to linear DNA than plumbagin. While plumbagin did not affect calcein-AM transport by P-glycoprotein the derivatives 1c and 2a exhibited a 50% or 80% inhibition of the P-glycoprotein-mediated calcein-AM efflux relative to the clinically established sensitizer verapamil. Copyright © 2014 Elsevier Inc. All rights reserved.

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 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.

Activity of Six Essential Oils Extracted from Tunisian Plants against Legionella pneumophila.

PubMed

Chaftar, Naouel; Girardot, Marion; Quellard, Nathalie; Labanowski, Jérôme; Ghrairi, Tawfik; Hani, Khaled; Frère, Jacques; Imbert, Christine

2015-10-01

The aim of this study was to investigate the composition of six essential oils extracted from Tunisian plants, i.e., Artemisia herba-alba Asso, Citrus sinensis (L.) Osbeck, Juniperus phoenicea L., Rosmarinus officinalis L., Ruta graveolens L., and Thymus vulgaris L., and to evaluate their activity against Legionella pneumophila (microdilution assays). Eight Legionella pneumophila strains were studied, including the two well-known serogroup 1 Lens and Paris strains as controls and six environmental strains isolated from Tunisian spas belonging to serogroups 1, 4, 5, 6, and 8. The essential oils were generally active against L. pneumophila. The activities of the A. herba-alba, C. sinensis, and R. officinalis essential oils were strain-dependent, whereas those of the J. phoenicea and T. vulgaris oils, showing the highest anti-Legionella activities, with minimum inhibitory concentrations (MICs) lower than 0.03 and lower than or equal to 0.07 mg/ml, respectively, were independent of the strains' serogroup. Moreover, the microorganisms treated with T. vulgaris essential oil were shorter, swollen, and less electron-dense compared to the untreated controls. Isoborneol (20.91%), (1S)-α-pinene (18.30%) β-phellandrene (8.08%), α-campholenal (7.91%), and α-phellandrene (7.58%) were the major components isolated from the J. phoenicea oil, while carvacrol (88.50%) was the main compound of the T. vulgaris oil, followed by p-cymene (7.86%). This study highlighted the potential interest of some essential oils extracted from Tunisian plants as biocides to prevent the Legionella risk. Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich.

New metal catalyzed syntheses of nanostructured boron nitride and alkenyldecaboranes

NASA Astrophysics Data System (ADS)

Chatterjee, Shahana

The goals of the research described in this dissertation were two-fold. The first goal was to develop new methods, employing metal-catalyzed chemical vapor deposition reactions of molecular polyborane precursors, for the production of boron nitride nanostructured materials, including both boron nitride nanotubes (BNNTs) and boron nitride nanosheets (BNNS). The second goal was to develop new systematic metal-catalyzed reactions for polyboranes that would facilitate their functionalization for possible biomedical and/or materials applications. The syntheses of multi- and double-walled BNNTs were achieved with the aid of a floating nickel catalyst via the catalytic chemical vapor deposition (CCVD) of borazine (B3N3H6) or decaborane (B10H14) molecular precursors in ammonia atmospheres, with each precursor having its own advantages. While borazine is a single-source precursor containing both boron and nitrogen, the decaborane-based syntheses required the additional step of reaction with ammonia. However, the higher observed BNNT yields and the ease of handling and commercial availability of decaborane are distinct advantages. The BNNTs derived from both precursors were crystalline with highly ordered structures. The BNNTs grown at 1200 ºC from borazine were mainly double walled, with lengths up to 0.2 µm and ˜2 nm diameters. The BNNTs grown at 1200-1300 ºC from decaborane were double- and multi-walled, with the double-walled nanotubes having ˜2 nm inner diameters and the multi-walled nanotubes (˜10 walls) having ˜4-5 nm inner diameters and ˜12-14 nm outer diameters. BNNTs grown from decaborane at 1300 ºC were longer, averaging ˜0.6 µm, whereas those grown at 1200 ºC had average lengths of ˜0.2 µm. The BNNTs were characterized using scanning and transmission electron microscopies (SEM and TEM), and electron energy loss spectroscopy (EELS). This floating catalyst method now provides a catalytic and potentially scalable route to BNNTs with low defect density from safe and commercially available precursor compounds. A catalytic CVD method, employing the thermally induced reactions of ammonia with decaborane on polycrystalline nickel and copper foils, was also successfully developed for the production of BNNS. The metals were readily etched and the BNNS transferred to other substrates. The EELS and Raman spectra and the electron diffraction patterns of the BNNS confirmed the formation of h-BN and their optical, AFM and TEM characterizations showed BNNS with large micron-scale areas with some crumpling and folding. Most of the BNNS deposited on Ni were two- or three-layered; however, some regions were thicker containing up to six BN sheets. The films on Cu also contained two- and three-layered BNNS, but had large amorphous BN regions. Many of the BNNS grown on Ni exhibited well-defined angular edges, with near regular angles of 30º, 60º or 90º, suggesting that with a fine-tuning of the decaborane/ammonia pressure and growth conditions, controlled growth of regular polygonal BNNS structures can be achieved. To achieve the second goal, transition-metal-catalyzed decaborane-alkyne hydroboration reactions were developed that provide high-yield routes to the previously unknown di- and monoalkenyldecaboranes. An unusual catalyst product selectivity was observed, with the reactions catalyzed by the [RuCl2 (p-cymene)]2 and [Cp*IrCl2]2 complexes giving the β-E alkenyldecaboranes and the corresponding reactions with the [RuI2(p-cymene)]2 complex giving the α-alkenyldecaborane isomers. These product selectivities coupled with the differences observed in NMR studies of catalyzed reactions in progress, suggest quite distinct mechanistic steps for the different catalysts. It was further demonstrated that the new alkenyldecaboranes could be easily modified with the aid of metal-catalyzed hydroborations and homo and cross metathesis reactions to yield both linked cage and chemically active derivatives. These results demonstrate that the alkenyldecaboranes could serve as important materials for many potential polyborane biomedical and/or materials applications.

A novel interpretation of the Fractional Inhibitory Concentration Index: The case Origanum vulgare L. and Leptospermum scoparium J. R. et G. Forst essential oils against Staphylococcus aureus strains.

PubMed

Fratini, Filippo; Mancini, Simone; Turchi, Barbara; Friscia, Elisabetta; Pistelli, Luisa; Giusti, Giulia; Cerri, Domenico

2017-01-01

Origanum vulgare (oregano) and Leptospermum scoparium (manuka) were traditionally employed as natural remedies for infected wounds and skin injuries where Staphylococcus aureus is mainly involved. The first aim of this study was to investigate oregano and manuka essential oils (EOs) chemical compositions and evaluate their antibacterial activity (MIC, Minimum Inhibitory Concentration) against fourteen S. aureus wild strains. The second aim was to evaluate the antibacterial activities of oregano and manuka EOs mixed in different combination (FIC, Fractional Inhibitory Concentration) with an improved chequerboard technique. This allowed to avoid the usual uncertainty in the determination of MIC and FIC values and to obtain a more precise interpretation of FIC indexes (FICIs). Moreover, FICIs were discussed on the basis of a novel interpretation method to evaluate the synergistic/antagonistic effect of EOs mixtures. The most representative compounds in oregano EO were Carvacrol (65.93%), p-Cymene (9.33%) and γ-Terpinene (5.25%), while in manuka EO were Leptospermone (31.65%), cis-Calamenene (15.93%) and Flavesone (6.92%). EOs presented MIC values ranging from 1:2048 to 1:4096 v/v and FIC values ranging from 0.125 to 1. According to our interpretation, a synergistic effect (34.68%), a commutative effect (15.32%) and an indifferent effect (50.00%) and no antagonistic effect were observed. Conversely, according to two previously proposed FICI interpretation models, 1.80% synergistic effect could be observed and, respectively, 98.20% indifferent effect or 48.20% additive effect and 50.00% indifferent effect. As practical results, oregano and manuka EOs may be an effective alternative to chemotherapic drugs in staphylococcal infections and useful tools to enhance food security. Copyright © 2016 Elsevier GmbH. All rights reserved.

Isolation and identification of host cues from mango, Mangifera indica, that attract gravid female oriental fruit fly, Bactrocera dorsalis.

PubMed

Jayanthi, Pagadala D Kamala; Woodcock, Christine M; Caulfield, John; Birkett, Michael A; Bruce, Toby J A

2012-04-01

The oriental fruit fly, Bactrocera dorsalis, is an economically damaging, polyphagous pest of fruit crops in South-East Asia and Hawaii, and a quarantine pest in other parts of the world. The objective of our study was to identify new attractants for B. dorsalis from overripe mango fruits. Headspace samples of volatiles were collected from two cultivars of mango, 'Alphonso' and 'Chausa', and a strong positive behavioral response was observed when female B. dorsalis were exposed to these volatiles in olfactometer bioassays. Coupled GC-EAG with female B. dorsalis revealed 7 compounds from 'Alphonso' headspace and 15 compounds from 'Chausa' headspace that elicited an EAG response. The EAG-active compounds, from 'Alphonso', were identified, using GC-MS, as heptane, myrcene, (Z)-ocimene, (E)-ocimene, allo-ocimene, (Z)-myroxide, and γ-octalactone, with the two ocimene isomers being the dominant compounds. The EAG-active compounds from 'Chausa' were 3-hydroxy-2-butanone, 3-methyl-1-butanol, ethyl butanoate, ethyl methacrylate, ethyl crotonate, ethyl tiglate, 1-octen-3-ol, ethyl hexanoate, 3-carene, p-cymene, ethyl sorbate, α-terpinolene, phenyl ethyl alcohol, ethyl octanoate, and benzothiazole. Individual compounds were significantly attractive when a standard dose (1 μg on filter paper) was tested in the olfactometer. Furthermore, synthetic blends with the same concentration and ratio of compounds as in the natural headspace samples were highly attractive (P < 0.001), and in a choice test, fruit flies did not show any preference for the natural samples over the synthetic blends. Results are discussed in relation to developing a lure for female B. dorsalis to bait traps with.

Efficacy of Nanoencapsulated Thymus eriocalyx and Thymus kotschyanus Essential Oils by a Mesoporous Material MCM-41 Against Tetranychus urticae (Acari: Tetranychidae).

PubMed

Ebadollahi, Asgar; Sendi, Jalal Jalali; Aliakbar, Alireza

2017-12-05

Inspite of well-established potentiality of plant essential oils as biopesticides, their environmentally low persistence is considered as a hindering obstacle for its commercialization. In the present study, chemical composition and toxicity of essential oils isolated from leaves of Thymus eriocalyx and Thymus kotschyanus were evaluated against two-spotted spider mite, Tetranychus urticae. The chemicals present in the crude oil were found to be thymol (28.83%), oleic acid (11.51%), palmitic acid (8.60%), borneol (5.72%), ρ-cymene (3.60%), and 1,8-cineole (3.57%) in the essential oil of T. eriocalyx, and camphene (35.59%), linalyl acetate (20.47%), linalool (14.75%), α-terpineol (13.87%), and geranyl acetate (3.07%) in the essential oil of T. kotschyanus. The essential oils had strong fumigant toxicity on the adult females of Te. urticae and their fumigation persistence was prolonged until 6 and 5 d, respectively, for T. eriocalyx and T. kotschyanus. Loading of essential oils in MCM-41 increased their stability and persistence was extended up to 20 and 18 d for T. eriocalyx and T. kotschyanus. Further, mite mortality increased from 80 to 203 mites by T. eriocalyx and from 58 to 186 mites by T. kotschyanus nanoencapsulated essential oils. Based on these results, nanoencapsulation of T. eriocalyx and T. kotschyanus essential oils in MCM-41 may be a useful method for their application in the management of Te. urticae. © The Author(s) 2017. Published by Oxford University Press on behalf of Entomological Society of America. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.

Ruthenium(II) arene complexes with chelating chloroquine analogue ligands: Synthesis, characterization and in vitro antimalarial activity†

PubMed Central

Glans, Lotta; Ehnbom, Andreas; de Kock, Carmen; Martínez, Alberto; Estrada, Jesús; Smith, Peter J.; Haukka, Matti; Sánchez-Delgado, Roberto A.; Nordlander, Ebbe

2012-01-01

Three new ruthenium complexes with bidentate chloroquine analogue ligands, [Ru(η6-cym)(L1)Cl]Cl (1, cym = p-cymene, L1 = N-(2-((pyridin-2-yl)methylamino)ethyl)-7-chloroquinolin-4-amine), [Ru(η6-cym)(L2)Cl]Cl (2, L2 = N-(2-((1-methyl-1H-imidazol-2-yl)methylamino)ethyl)-7-chloroquinolin-4-amine) and [Ru(η6-cym)(L3)Cl] (3, L3 = N-(2-((2-hydroxyphenyl)methylimino)ethyl)-7-chloroquinolin-4-amine) have been synthesized and characterized. In addition, the X-ray crystal structure of 2 is reported. The antimalarial activity of complexes 1–3 and ligands L1, L2 and L3, as well as the compound N-(2-(bis((pyridin-2-yl)methyl)amino)ethyl)-7-chloroquinolin-4-amine (L4), against chloroquine sensitive and chloroquine resistant Plasmodium falciparum malaria strains was evaluated. While 1 and 2 are less active than the corresponding ligands, 3 exhibits high antimalarial activity. The chloroquine analogue L2 also shows good activity against both the choloroquine sensitive and the chloroquine resistant strains. Heme aggregation inhibition activity (HAIA) at an aqueous buffer/n-octanol interface (HAIR50) and lipophilicity (D, as measured by water/n-octanol distribution coefficients) have been measured for all ligands and metal complexes. A direct correlation between the D and HAIR50 properties cannot be made because of the relative structural diversity of the complexes, but it may be noted that these properties are enhanced upon complexation of the inactive ligand L3 to ruthenium, to give a metal complex (3) with promising antimalarial activity. PMID:22249579

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.

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

Ratcliff, Matthew A.; Burton, Jonathan; Sindler, Petr

Several high octane number oxygenates that could be derived from biomass were blended with gasoline and examined for performance properties and their impact on knock resistance and fine particle emissions in a single cylinder direct-injection spark-ignition engine. The oxygenates included ethanol, isobutanol, anisole, 4-methylanisole, 2-phenylethanol, 2,5-dimethyl furan, and 2,4-xylenol. These were blended into a summertime blendstock for oxygenate blending at levels ranging from 10 to 50 percent by volume. The base gasoline, its blends with p-xylene and p-cymene, and high-octane racing gasoline were tested as controls. Relevant gasoline properties including research octane number (RON), motor octane number, distillation curve, andmore » vapor pressure were measured. Detailed hydrocarbon analysis was used to estimate heat of vaporization and particulate matter index (PMI). Experiments were conducted to measure knock-limited spark advance and particulate matter (PM) emissions. The results show a range of knock resistances that correlate well with RON. Molecules with relatively low boiling point and high vapor pressure had little effect on PM emissions. In contrast, the aromatic oxygenates caused significant increases in PM emissions (factors of 2 to 5) relative to the base gasoline. Thus, any effect of their oxygen atom on increasing local air-fuel ratio was outweighed by their low vapor pressure and high double-bond equivalent values. For most fuels and oxygenate blend components, PMI was a good predictor of PM emissions. However, the high boiling point, low vapor pressure oxygenates 2-phenylethanol and 2,4-xylenol produced lower PM emissions than predicted by PMI. This was likely because they did not fully evaporate and combust, and instead were swept into the lube oil.« less

Evaluation of antifungal activities of the essential oil and various extracts of Nigella sativa and its main component, thymoquinone against pathogenic dermatophyte strains.

PubMed

Mahmoudvand, H; Sepahvand, A; Jahanbakhsh, S; Ezatpour, B; Ayatollahi Mousavi, S A

2014-12-01

Plant extracts and plant-derived compounds are valuable sources as folk medicine for the treatment and prevention of a wide range of diseases including infectious diseases. In the present study, the antifungal activities of the essential oil and various extracts Nigella sativa and its active principle, thymoquinone against Trichophyton mentagrophytes, Microsporum canis and Microsporum gypseum as pathogenic dermatophyte strains have been evaluated. In addition, the cytotoxic effects of N. sativa against murine macrophage cells were determined. In this study, the antifungal activity was studied by disk diffusion method and assessment of minimum inhibitory concentration (MIC) of extracts using broth macrodilution method. In addition, the cytotoxic activity of N. sativa was evaluated by colorimetric assay (MTT). The components of the N. sativa essential oil were also identified by gas chromatography/mass spectroscopy (GC/MS) analysis. The results showed that the essential oil and various extracts of N. sativa particularly thymoquinone have potent antifungal effects on T. mentagrophytes, M. canis and M. gypseum as pathogenic dermatophyte strains. In the assessment of the cytotoxicity activity, it could be observed that N. sativa had no significant cytotoxicity in the murine macrophages at low concentrations. While, thymoquinone in comparison with essential oil and various extracts of N. sativa showed higher cytotoxicity on murine macrophage cells. In the GC/MS analysis, thymoquinone (42.4%), p-cymene (14.1%), carvacrol (10.3%) and longifolene (6.1%) were found to be the major components of N. sativa essential oil. The findings of this study suggest a first step in the search of new antidermatophytic drugs and aid the use of N. sativa seeds in the traditional medicine for dermatophytic infections. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

In vivo and in vitro control activity of plant essential oils against three strains of Aspergillus niger.

PubMed

Kumar, Peeyush; Mishra, Sapna; Kumar, Atul; Kumar, Sanjeev; Prasad, Chandra Shekhar

2017-09-01

Contamination of environment and food from the prevalent spores and mycotoxins of Aspergillus niger has led to several diseases in humans and other animals. The present study investigated the control activity of plant essential oils against three strains of A. niger. In the elaborate assays done through microdilution plate assay and agar disk diffusion assay in the lab condition and in vivo assay on the stored wheat grains, the essential oil of Thymus vulgaris depicted overall superior efficacy. In microdilution plate assay, the oil of Anethum graveolens showed best fungistatic activity, while best fungicidal activity was depicted by Syzygium aromaticum oil. The oil of T. vulgaris showed moderate control efficacy against A. niger strains with its antifungal activity resulting mainly due to killing of microorganism rather than growth inhibition. In agar disk diffusion assay, T. vulgaris oil with a zone of inhibition (ZOI) of 23.3-61.1% was the most effective fungicide. The in vivo assay to evaluate the protection efficacy of oils for stored wheat grains against A. niger (AN1) revealed T. vulgaris (90.5-100%) to be the best control agent, followed by the oil of S. aromaticum (61.9-100%). The GC-MS analysis of T. vulgaris oil indicated the presence of thymol (39.11%), γ-terpinene (19.73%), o-cymene (17.21%), and β-pinene (5.38%) as major oil components. Phytotoxic effects of the oils on wheat seeds showed no significant phytotoxic effect of oils in terms of seed germination or seedling growth. The results of the study demonstrated control potentiality of essential oils for the protection of stored wheat against A. niger with prospect for development of eco-friendly antifungal products.

Insecticide Activity of Essential Oils of Mentha longifolia, Pulicaria gnaphalodes and Achillea wilhelmsii Against Two Stored Product Pests, the Flour Beetle, Tribolium castaneum, and the Cowpea Weevil, Callosobruchus maculatus

PubMed Central

Khani, Abbas; Asghari, Javad

2012-01-01

Essential oils extracted from the foliage of Mentha longifolia (L.) (Lamiales: Lamiaceae) and Pulicaria gnaphalodes Ventenat (Asterales: Asteraceae), and flowers of Achillea wilhelmsii C. Koch (Asterales: Asteraceae) were tested in the laboratory for volatile toxicity against two storedproduct insects, the flour beetle, Tribolium castaneum Herbst (Coleoptera: Tenebrionidae) and the cowpea weevil, Callosobruchus maculatus F. (Coleoptera: Bruchidae). The chemical composition of the isolated oils was examined by gas chromatography-mass spectrometry. InM longifolia, the major compounds were piperitenon (43.9%), tripal (14.3%), oxathiane (9.3%), piperiton oxide (5.9%), and d-limonene (4.3%). In P. gnaphalodes, the major compounds were chrysanthenyl acetate (22.38%), 2L -4L-dihydroxy eicosane (18.5%), verbenol (16.59%), dehydroaromadendrene (12.54%), β-pinen (6.43%), and 1,8 cineol (5.6%). In A. wilhelmsii, the major compounds were 1,8 cineole (13.03%), caranol (8.26%), alpha pinene (6%), farnesyl acetate (6%), and p-cymene (6%). C maculatus was more susceptible to the tested plant products than T castaneum. The oils of the three plants displayed the same insecticidal activity against C. maculatus based on LC50 values (between 1.54µl/L air in P. gnaphalodes, and 2.65 µl/L air in A. wilhelmsii). While the oils of A. wilhelmsii and M. longifolia showed the same strong insecticidal activity against T. castaneum (LC50 = 10.02 and 13.05 µl/L air, respectively), the oil of P. gnaphalodes revealed poor activity against the insect (LC50 = 297.9 µl/L air). These results suggested that essential oils from the tested plants could be used as potential control agents for stored-product insects. PMID:23413994

Insecticide activity of essential oils of Mentha longifolia, Pulicaria gnaphalodes and Achillea wilhelmsii against two stored product pests, the flour beetle, Tribolium castaneum, and the cowpea weevil, Callosobruchus maculatus.

PubMed

Khani, Abbas; Asghari, Javad

2012-01-01

Essential oils extracted from the foliage of Mentha longifolia (L.) (Lamiales: Lamiaceae) and Pulicaria gnaphalodes Ventenat (Asterales: Asteraceae), and flowers of Achillea wilhelmsii C. Koch (Asterales: Asteraceae) were tested in the laboratory for volatile toxicity against two storedproduct insects, the flour beetle, Tribolium castaneum Herbst (Coleoptera: Tenebrionidae) and the cowpea weevil, Callosobruchus maculatus F. (Coleoptera: Bruchidae). The chemical composition of the isolated oils was examined by gas chromatography-mass spectrometry. InM longifolia, the major compounds were piperitenon (43.9%), tripal (14.3%), oxathiane (9.3%), piperiton oxide (5.9%), and d-limonene (4.3%). In P. gnaphalodes, the major compounds were chrysanthenyl acetate (22.38%), 2L -4L-dihydroxy eicosane (18.5%), verbenol (16.59%), dehydroaromadendrene (12.54%), β-pinen (6.43%), and 1,8 cineol (5.6%). In A. wilhelmsii, the major compounds were 1,8 cineole (13.03%), caranol (8.26%), alpha pinene (6%), farnesyl acetate (6%), and p-cymene (6%). C maculatus was more susceptible to the tested plant products than T castaneum. The oils of the three plants displayed the same insecticidal activity against C. maculatus based on LC(50) values (between 1.54µl/L air in P. gnaphalodes, and 2.65 µl/L air in A. wilhelmsii). While the oils of A. wilhelmsii and M. longifolia showed the same strong insecticidal activity against T. castaneum (LC(50) = 10.02 and 13.05 µl/L air, respectively), the oil of P. gnaphalodes revealed poor activity against the insect (LC(50) = 297.9 µl/L air). These results suggested that essential oils from the tested plants could be used as potential control agents for stored-product insects.

Molecular and phytochemical investigation of Angelica dahurica and Angelica pubescentis essential oils and their biological activity against Aedes aegypti, Stephanitis pyrioides, and Colletotrichum species.

PubMed

Tabanca, Nurhayat; Gao, Zengping; Demirci, Betul; Techen, Natascha; Wedge, David E; Ali, Abbas; Sampson, Blair J; Werle, Chris; Bernier, Ulrich R; Khan, Ikhlas A; Baser, Kemal Husnu Can

2014-09-03

In this study, Angelica dahurica and Angelica pubescentis root essential oils were investigated as pest management perspectives, and root samples were also analyzed genetically using the nuclear ribosomal internal transcribed spacer (ITS) region as a DNA barcode marker. A. pubescentis root essential oil demonstrated weak antifungal activity against Colletotrichum acutatum, Colletotrichum fragariae, and Colletotrichum gloeosporioides, whereas A. dahurica root essential oil did not show antifungal activity. Conversely, A. dahurica root essential oil demonstrated better biting deterrent and insecticidal activity against yellow fever mosquito, Aedes aegypti, and azalea lace bugs, Stephanitis pyrioides, than A. pubescentis root oil. The major compounds in the A. dahurica oil were found as α-pinene (46.3%), sabinene (9.3%), myrcene (5.5%), 1-dodecanol (5.2%), and terpinen-4-ol (4.9%). α-Pinene (37.6%), p-cymene (11.6%), limonene (8.7%), and cryptone (6.7%) were the major compounds found in the A. pubescentis oil. In mosquito bioassays, 1-dodecanol and 1-tridecanol showed antibiting deterrent activity similar to the positive control DEET (N,N-diethyl-3-methylbenzamide) at 25 nmol/cm(2) against Ae. aegypti, whereas only 1-tridecanol showed repellent activity in human-based cloth patch bioassay with minimum effective dosages (MED) of 0.086 ± 0.089 mg/cm(2) (DEET = 0.007 ± 0.003 mg/cm(2)). In larval bioassays, 1-tridecanol was more toxic with an LC50 value of 2.1 ppm than 1-dodecanol having an LC50 value of 5.2 ppm against 1-day-old Ae. aegypti larvae. 1-Dodecanol and 1-tridecanol could be useful for the natural mosquito control agents.

Fungitoxic activity of 12 essential oils against four postharvest citrus pathogens: chemical analysis of thymus capitatus oil and its effect in subatmospheric pressure conditions.

PubMed

Arras, G; Usai, M

2001-07-01

The fungitoxic activity against Penicillium digitatum, Penicillium italicum, Botrytis cinerea, and Alternaria citri of 12 essential oils (EOs) distilled from medicinal plants is reported. The results of the in vitro trials show strong fungitoxic activity of Thymus capitatus (L.) Hofmgg EOs, which inhibited the growth of the four fungi at a concentration of 250 ppm (vol/vol). The other 11 essences reduced the development of the fungi from 95 to 9% at 250 ppm (vol/vol). The fungitoxic activity of T. capitatus EOs (75, 150, and 250 ppm) on healthy orange fruits, inoculated with P. digitatum (10(8) conidia ml(-1)) by spraying and placed in 10-liter desiccators, was weak at atmospheric pressure (3 to 10% inhibition at all three concentrations), while in vacuum conditions (0.5 bar), conidial mortality on the exocarp was high (90 to 97% at all three concentrations). These data proved not to be statistically different from treatments with thiabendazole-TBZ (2,000 ppm). Scanning electron microscope observations showed that T. capitatus EO vapors altered the morphology of P. digitatum hyphae and conidia. The gas-chromatographic analyses of thyme EO indicated that carvacrol was present at 81 to 83%, p-cymene at 4.5 to 5%, gamma-terpinene at 2.6 to 3.3%, caryophyllene at 1.5 to 1.6%, beta-myrcene at 1.6%, and linalool at 1.1 to 1.2%. Carvacrol proved to be the most important fungitoxic compound among the thyme EO constituents, but, unlike thyme EO, it caused alterations to the fruit at the concentration of 75 ppm.

Chemical composition and anticancer and antioxidant activities of Schinus molle L. and Schinus terebinthifolius Raddi berries essential oils.

PubMed

Bendaoud, Houcine; Romdhane, Mehrez; Souchard, Jean Pierre; Cazaux, Sylvie; Bouajila, Jalloul

2010-08-01

Essential oils were obtained by steam distillation from berries of Schinus molle L. and Schinus terebinthifolius Raddi originating from southern of Tunisia and analyzed by GC-FID and GC-MS. Among 57 and 62 compounds (%[mg/100 g dry matter]) identified in these oils, the main were alpha-phellandrene (46.52%[1256.15] and 34.38%[859.60]), beta-phellandrene (20.81%[561.74] and 10.61%[265.15]), alpha-terpineol (8.38%[226.26] and 5.60%[140.03]), alpha-pinene (4.34%[117.29] and 6.49%[162.25]), beta-pinene (4.96%[133.81] and 3.09%[77.30]) and p-cymene (2.49%[67.28] and 7.34%[183.40]), respectively. A marked quantity of gamma-cadinene (18.04%[451.05]) was also identified in the S. terebinthifolius essential oil whereas only traces (0.07%[1.81]) were detected in the essential oil of S. molle. The in vitro antioxidant and antiradical scavenging properties of the investigated essential oils were evaluated by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-Azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. Essential oil of S. terebinthifolius expressed stronger antioxidant activity in the ABTS assay, with an IC(50) of 24 +/- 0.8 mg/L, compared to S. molle (IC(50)= 257 +/- 10.3 mg/L). Essential oils were also evaluated for their anticancer activities against human breast cancer cells (MCF-7). S. terebinthifolius essential oil was more effective against tested cell lines (IC(50)= 47 +/- 9 mg/L) than that from S. molle (IC(50)= 54 +/- 10 mg/L). Suggestions on relationships between chemical composition and biological activities are outlined.

Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants.

PubMed

Escande, Vincent; Renard, Brice-Loïc; Grison, Claude

2015-04-01

Among the phytotechnologies used for the reclamation of degraded mining sites, phytoextraction aims to diminish the concentration of polluting elements in contaminated soils. However, the biomass resulting from the phytoextraction processes (highly enriched in polluting elements) is too often considered as a problematic waste. The manganese-enriched biomass derived from native Mn-hyperaccumulating plants of New Caledonia was presented here as a valuable source of metallic elements of high interest in chemical catalysis. The preparation of the catalyst Eco-Mn1 and reagent Eco-Mn2 derived from Grevillea exul exul and Grevillea exul rubiginosa was investigated. Their unusual polymetallic compositions allowed to explore new reactivity of low oxidative state of manganese-Mn(II) for Eco-Mn1 and Mn(IV) for Eco-Mn2. Eco-Mn1 was used as a Lewis acid to catalyze the acetalization/elimination of aldehydes into enol ethers with high yields; a new green and stereoselective synthesis of (-)-isopulegol via the carbonyl-ene cyclization of (+)-citronellal was also performed with Eco-Mn1. Eco-Mn2 was used as a mild oxidative reagent and controlled the oxidation of aliphatic alcohols into aldehydes with quantitative yields. Oxidative cleavage was interestingly noticed when Eco-Mn2 was used in the presence of a polyol. Eco-Mn2 allowed direct oxidative iodination of ketones without using iodine, which is strongly discouraged by new environmental legislations. Finally, the combination of the properties in the Eco-Mn catalysts and reagents gave them an unprecedented potential to perform sequential tandem oxidation processes through new green syntheses of p-cymene from (-)-isopulegol and (+)-citronellal; and a new green synthesis of functionalized pyridines by in situ oxidation of 1,4-dihydropyridines.

Essential Oil Composition and Antibacterial Activity of Origanum vulgare subsp. glandulosum Desf. at Different Phenological Stages

PubMed Central

Chaabane, Hédia; Jemli, Maroua; Boulila, Abdennacer; Boussaid, Mohamed

2013-01-01

Abstract Variation in the quantity and quality of the essential oil (EO) of wild population of Origanum vulgare at different phenological stages, including vegetative, late vegetative, and flowering set, is reported. The oils of air-dried samples were obtained by hydrodistillation. The yield of oils (w/w%) at different stages were in the order of late vegetative (2.0%), early vegetative (1.7%), and flowering (0.6%) set. The oils were analyzed by gas chromatography (GC) and GC–mass spectrometry (GC-MS). In total, 36, 33, and 16 components were identified and quantified in vegetative, late vegetative, and flowering set, representing 94.47%, 95.91%, and 99.62% of the oil, respectively. Carvacrol was the major compound in all samples. The ranges of major constituents were as follows: carvacrol (61.08–83.37%), p-cymene (3.02–9.87%), and γ-terpinene (4.13–6.34%). Antibacterial activity of the oils was tested against three Gram-positive and two Gram-negative bacteria by the disc diffusion method and determining their diameter of inhibition and the minimum inhibitory concentration (MIC) values. The inhibition zones and MIC values for bacterial strains, which were sensitive to the EO of O. vulgare subsp. glandulosum, were in the range of 9–36 mm and 125–600 μg/mL, respectively. The oils of various phenological stages showed high activity against all tested bacteria, of which Bacillus subtilis was the most sensitive and resistant strain, respectively. Thus, they represent an inexpensive source of natural antibacterial substances that exhibited potential for use in pathogenic systems. PMID:24320986

Synergistic antimicrobial activity of Boswellia serrata Roxb. ex Colebr. (Burseraceae) essential oil with various azoles against pathogens associated with skin, scalp and nail infections.

PubMed

Sadhasivam, S; Palanivel, S; Ghosh, S

2016-12-01

Antimicrobials from natural sources have gained immense importance in recent times to combat the global challenge of antibiotic resistance. Essential oils are implicated in antimicrobial action against several species. Here, we have screened nine commercially available essential oils for their antimicrobial activity against organisms associated with skin, scalp and nail infections mainly Propionibacterium acnes, Malassezia spp., Candida albicans and Trichophyton spp. Among nine essential oils, Boswellia serrata essential oil demonstrated superior antimicrobial activity against all the micro-organisms and surprisingly it showed maximum activity against Trichophyton spp. The gas chromatography-mass spectrometry analysis of B. serrata oil indicates a major composition of α thujene, ρ cymene and sabinene. Additionally, B. serrata oil was found to inhibit Staphylococcus epidermidis biofilm, and its combination with azoles has shown synergistic activity against azole-resistant strain of C. albicans. These broad-spectrum antimicrobial activities of B. serrata oil will make it an ideal candidate for topical use. Eradication of skin and nail infections still remain a challenge and there are serious concerns regarding the recurrence of the diseases associated with these infections. Antimicrobials from plant sources are gaining importance in therapeutics because they encounter minimal challenges of emergence of resistance. We have demonstrated the antimicrobial activity of Boswellia serrata essential oil against micro-organisms involved in skin, scalp and nail infections, especially if it has shown favourable synergistic antifungal activity in combination with azoles against the azole-resistant Candida albicans strain. Thus, B. serrata oil can be one of the plausible therapeutic agents for management of skin, scalp and nail infections. © 2016 The Society for Applied Microbiology.

Lipophilicity-dependent ruthenium N-heterocyclic carbene complexes as potential anticancer agents.

PubMed

Lv, Gaochao; Guo, Liubin; Qiu, Ling; Yang, Hui; Wang, Tengfei; Liu, Hong; Lin, Jianguo

2015-04-28

Five Ru(II)-N-heterocyclic carbenes (NHC) (1-5) were synthesized by reacting the appropriately substituted imidazolium chlorides with Ag2O, forming the NHC-silver chloride in situ followed by transmetalation with dimeric p-cymene ruthenium(II) dichloride. All the complexes were characterized by NMR and ESI-MS, and complex 1 was also characterized by single-crystal X-ray diffraction. The IC50 values of these five complexes were determined by the MTT-based assay on four human cancer cell lines, SKOV-3 (ovarian), PC-3 (prostate), MDA-MB-231 (breast) and EC109 (esophagus). The cytotoxicities of these complexes changed from a moderate effect to a fine one, corresponding to the increasing lipophilicity order of the complex of 2 < 1 < 3 < 4 < 5 (0.91, 0.88, 1.36, 1.85 and 2.62 for 1–5 respectively). Complex 5 showed the most cytotoxicity with the IC50 values 10.3 ± 0.3 μM for SKOV-3, 2.9 ± 0.1 μM for PC-3, 8.2 ± 0.6 μM for MDA-MB-231, 6.4 ± 0.2 μM for EC109 cell lines. Due to the superior cytotoxicity of complex 5 against the PC-3 cell lines, further biological evaluations were carried out to elucidate its action mechanism. The morphologic changes and cell cycle analysis showed that complex 5 can inhibit PC-3 cell lines by inducing cell cycle arrest at the G2/M phase. The DNA binding experiments further demonstrate that complex 5 has a better binding ability for DNA (Kb = 2.2 × 10(6) M(-1)) than complexes 1-4 (3.8 × 10(5), 7.0 × 10(5), 5.7 × 10(5), and 1.9 × 10(5) respectively).

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.

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.

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.

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 .

Relation between chemical composition or antioxidant activity and antihypertensive activity for six essential oils.

PubMed

Yvon, Yan; Raoelison, Emmanuel Guy; Razafindrazaka, René; Randriantsoa, Adolphe; Romdhane, Mehrez; Chabir, Naziha; Mkaddem, Mounira Guedri; Bouajila, Jalloul

2012-08-01

Six essential oils (EOs), Juniperus phoenicea (leaves and berries), Thymus capitatus, Lauris nobilis, Melaleuca armillaris, and Eucalyptus gracilis, were screened for their antioxidant and antihypertensive activity as well as their chemical compositions. We identified and quantified 24 compounds (representing 99.8% of total oil) for J. phoenicea leaves, 14 compounds (representing 98.8% of total oil) for J. phoenicea berries, 11 compounds (representing 99.6% of total oil) for T. capitatus, 32 compounds (representing 98.9% of total oil) for L. nobilis, 32 compounds (representing 98.7% of total oil) for M. armillaris, and 26 compounds (representing 99.3% of total oil) for E. gracilis. In the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, the antioxidant activity was in the range of 0.59 to 2183.6 mg/L, whereas T. capitatus (1.24 ± 0.05 mg/L) gave the best activity in the 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonate assay. Antihypertensive activity was evaluated by testing the vasorelaxing capacity of EOs on rat aorta precontracted by phenylephrine (10(-6) M). T. capitatus and L. nobilis were most active for an antihypertensive activity (29 ± 3 and 59 ± 2 mg/L, respectively). Correlations between chemical composition or antioxidant activity and/or antihypertensive activity were studied. Significant correlation has been found for antihypertensive activity and p-cymene (R(2) = 0.86), β-elemene (R(2) = 0.90), and β-myrcene (R(2) = 0.76). A good correlation has been found between antihypertensive activity and antioxidant activity by DPPH assay (R(2) = 0.98). Antioxidant activity can contribute to the prevention of the increase of the blood pressure. According to the literature, no study has been reported until now of correlation between antihypertensive activity and antioxidant activity. Natural EOs can find its interest and application in a medicinal area. © 2012 Institute of Food Technologists®

Clausena anisata and Dysphania ambrosioides essential oils: from ethno-medicine to modern uses as effective insecticides.

PubMed

Pavela, Roman; Maggi, Filippo; Lupidi, Giulio; Mbuntcha, Hélène; Woguem, Verlaine; Womeni, Hilaire Macaire; Barboni, Luciano; Tapondjou, Léon Azefack; Benelli, Giovanni

2018-04-01

Dysphania ambrosioides (L.) Mosyakin & Clemants (Amaranthaceae) and Clausena anisata (Willd.) Hook. f. ex Benth. (Rutaceae) are two aromatic species traditionally used in Cameroon to repel and kill insects. The present work was carried out to substantiate this traditional use and to evaluate the possible incorporation in commercial botanical insecticides of their essential oils (EOs). The EOs were distilled from leaves of C. anisata and aerial parts of D. ambrosioides and analyzed by gas chromatography-mass spectrometry (GC-MS). The insecticidal activity of both EOs was investigated against the filariasis vector, Culex quinquefasciatus, and the housefly, Musca domestica. As possible mode of action, the inhibition of acetylcholinesterase (AChE) by the two EOs was investigated as well. The D. ambrosioides EO was characterized by the monoterpene peroxide ascaridole (61.4%) and the aromatic p-cymene (29.0%), whereas the C. anisata EO was dominated by the phenylpropanoids (E)-anethole (64.6%) and (E)-methyl isoeugenol (16.1%). The C. anisata EO proved to be very toxic to third instar larvae of C. quinquefasciatus showing LC 50 of 29.3 μl/l, whereas D. ambrosioides EO was more toxic to adults of M. domestica showing a LD 50 of 51.7 μg/adult. The mixture of both EOs showed a significant synergistic effect against mosquito larvae with LC 50 estimated as 19.3 μl/l, whereas this phenomenon was not observed upon application to M. domestica adults (LD 50 = 75.9 μg/adult). Of the two EOs, the D. ambrosioides one provided a good inhibition of AChE (IC 50 = 77 μg/ml), whereas C. anisata oil was not effective. These findings provide new evidences supporting the ethno-botanical use of these two Cameroonian plants, and their possible application even in synergistic binary blends, to develop new eco-friendly, safe and effective herbal insecticides.

Selective Essential Oils from Spice or Culinary Herbs Have High Activity against Stationary Phase and Biofilm Borrelia burgdorferi

PubMed Central

Feng, Jie; Zhang, Shuo; Shi, Wanliang; Zubcevik, Nevena; Miklossy, Judith; Zhang, Ying

2017-01-01

Although the majority of patients with acute Lyme disease can be cured with the standard 2–4 week antibiotic treatment, about 10–20% of patients continue suffering from chronic symptoms described as posttreatment Lyme disease syndrome. While the cause for this is debated, one possibility is that persister bacteria are not killed by the current Lyme antibiotics and remain active in the system. It has been reported that essential oils have antimicrobial activities and some have been used by patients with persisting Lyme disease symptoms. However, the activity of essential oils against the causative agent Borrelia burgdorferi (B. burgdorferi) has not been well studied. Here, we evaluated the activity of 34 essential oils against B. burgdorferi stationary phase culture as a model for persister bacteria. We found that not all essential oils had activity against the B. burgdorferi stationary phase culture, with top five essential oils (oregano, cinnamon bark, clove bud, citronella, and wintergreen) at a low concentration of 0.25% showing high anti-persister activity that is more active than the known persister drug daptomycin. Interestingly, some highly active essential oils were found to have excellent anti-biofilm ability as shown by their ability to dissolve the aggregated biofilm-like structures. The top three hits, oregano, cinnamon bark, and clove bud completely eradicated all viable cells without any regrowth in subculture in fresh medium, whereas but not citronella and wintergreen did not have this effect. Carvacrol was found to be the most active ingredient of oregano oil showing excellent activity against B. burgdorferi stationary phase cells, while other ingredients of oregano oil p-cymene and α-terpinene had no apparent activity. Future studies are needed to characterize and optimize the active essential oils in drug combination studies in vitro and in vivo and to address their safety and pharmacokinetic properties before they can be considered as a novel treatment of persistent Lyme disease. PMID:29075628

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.

Evaluation of antioxidant and antimicrobial activities of essential oils from Carum copticum seed and Ferula assafoetida latex.

PubMed

Kavoosi, Gholamreza; Tafsiry, Asad; Ebdam, Ali Asghar; Rowshan, Vahid

2013-02-01

Carum copticum and Ferula assafoetida have several medicinal properties including antispasmodic, carminative, sedative, analgesic, and antiseptic. Reactive oxygen species (ROS), reactive nitrogen species (RNS), hydrogen peroxide (H(2) O(2) ), and thiobarbituric acid reactive substances (TBARS) scavenging activities of Carum and Ferula oils along with their antibacterial and antifungal activities were examined. Thymol (40.25%), γ-terpinene (38.7%) and p-cymene (15.8%) were detected as the main components of Carum oil while, β-pinene (47.1%), α-pinene (21.36%), and 1, 2-dithiolane (18.6%) were the main components of Ferula oil. Inhibitory concentrations (IC50) for total radical scavenging were between 40 and 60 and 130 and 160 μg/mL of Carum and Ferula oil, respectively. Minimal inhibitory concentration (MIC) for Salmonella typhi, Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Aspergillus niger, and Candida albicans were 78 ± 8, 65 ± 7, 14 ± 3, 5 ± 2, 5.6 ± 1.3, and 8.8 ± 2.2 μg/mL of Carum oil, respectively. MIC for S. typhi, E. coli, S. aureus, B. subtilis, A. niger, and C. albicans were >200, >200, 125 ± 17, 80 ± 12, 85 ± 5, and 90 ± 11 μg/mL of Ferula oil, respectively. Accordingly, Carum and Ferula oils could be used as safe and effective natural antioxidants to improve the oxidative stability of fatty foods during storage and to preserve foods against food burn pathogens. This study clearly demonstrates the potential of Carum and Ferula oil especially Carum oil as natural antioxidant and antimicrobial agent. The chemical composition of essential oils was identified. Thus, identification of such compounds also helps to discover of new antioxidant, antibacterial and antifungal agents for potential applications in food safety and food preservation. © 2013 Institute of Food Technologists®

Chemical composition of essential oils and in vitro antioxidant activity of fresh and dry leaves crude extracts of medicinal plant of Lactuca Sativa L. native to Sultanate of Oman.

PubMed

Al Nomaani, Rahma Said Salim; Hossain, Mohammad Amzad; Weli, Afaf Mohammed; Al-Riyami, Qasim; Al-Sabahi, Jamal Nasser

2013-05-01

To isolate and analyse the chemical composition in the essential oils and free radical scavenging activity of different crude extracts from the fresh and dry leaves of vegetable plants of Lactuca sativa L. (L. sativa). The essential oils and volatile chemical constituents were isolated from the fresh and dry leaves of L. sativa (lettuce) grown in Sultanate of Oman by hydro distillation method. The antioxidant activity of the crude extracts was carried out by well established free radical scavenging activity (DPPH) method. About 20 chemical compounds of different concentration representing 83.07% and 79.88% respectively were isolated and identified by gas chromatography-mass spectroscopy in the essential oils isolated from the fresh and dry leaves as α-pinene (5.11% and 4.05%), γ-cymene (2.07% and 1.92%), thymol (11.55% and 10.73%), durenol (52.00% and 49.79%), α-terpinene (1.66% and 1.34%), thymol acetate (0.99% and 0.67%), caryophyllene (2.11% and 1.98%), spathulenol (3.09% and 2.98%), camphene (4.11% and 3.65%), limonene (1.28% and 1.11%) representing these major chemical compounds. However, some other minor chemical constituents were also isolated and identified from the essential oil of lettuce including β-pinene, α-terpinolene, linalool, 4-terpineol, α-terpineol, o-methylthymol, L-alloaromadendrene and viridiflorene. The chemical constituents in the essential oils from the locally grown lettuce were identified in the following classes or groups of chemical compounds such as monoterpenes, sesquiterpenes volatile organic compounds and their oxygenated hydrocarbons. Therefore, the essential oils and the crude extracts from Omani vegetable species of lettuce are active candidates which would be used as antioxidant, antifungal or antimicrobial agents in new drugs preparation for therapy of infectious diseases.

Effect of essential oil from fresh leaves of Ocimum gratissimum L. on mycoflora during storage of peanuts in Benin.

PubMed

Adjou, Euloge S; Kouton, Sandrine; Dahouenon-Ahoussi, Edwige; Soumanou, Mohamed M; Sohounhloue, Dominique C K

2013-02-01

The aim of this study was to evaluate the effect of essential oil from fresh leaves of Sweet Fennel (Ocimum gratissimum) on mycoflora and Aspergillus section Flavi populations in stored peanuts. Aspergillus, Fusarium and Mucor spp. were the most common genera identified from peanuts at post-harvest in Benin by using a taxonomic schemes primarily based on morphological characters of mycelium and conidia. The isolated fungi include Aspergillus niger, A. parasiticus, A. flavus, A. ochraceus, Fusarium graminearum, F. solani, F. oxysporum and Mucor spp. The most prevalent fungi recorded were A. niger (94.18 %), A. flavus (83.72 %), A. parasiticus (77.90 %), A. ochraceus (72.09 %), F. graminearum (59.30 %) and F. oxysporum (51.16 %). Antifungal assay, performed by the agar medium assay, indicated that essential oil exhibited high antifungal activity against the growth of A. flavus, A. parasiticus, A. ochraceus and F. oxysporium. The minimal inhibitory concentration (MIC) of the essential oil was found to be 7.5 μl/ml for A. flavus and A. parasiticus and 5.5 μl/ml for A. ochraceus and F. oxysporium. The minimal fungicidal concentration (MFC) was recorded to be 8.0 μl/ml for A. flavus and A. parasiticus, 6,5 μl/ml for A. ochraceus and 6.0 μl/ml for F. oxysporium. The essential oil was found to be strongly fungicidal and inhibitory to aflatoxin production. Chemical analysis by GC/MS of the components of the oil led to the identification of 31 components characterized by myrcene (6.4 %), α-thujene (8.2 %), p-cymene (17.6 %), γ-terpinene (20.0 %), and thymol (26.9 %) as major components. The essential oil of Sweet Fennel, with fungal growth and mycotoxin inhibitory properties, offers a novel approach to the management of storage, thus opening up the possibility to prevent mold contamination in stored peanuts.

Volatile aroma components and antioxidant activities of the flavedo peel extract of unripe Shiikuwasha (Citrus depressa Hayata).

PubMed

Asikin, Yonathan; Taira, Ikuko; Inafuku, Sayuri; Sumi, Hidekazu; Sawamura, Masayoshi; Takara, Kensaku; Wada, Koji

2012-04-01

The flavedo peel extracts of unripe Shiikuwasha (Citrus depressa Hayata) fruits were extracted using steam distillation (SD) or a cold-press (CP) system. Volatile aroma content and composition were determined using gas chromatography (GC) and each compound was identified using gas chromatography-mass spectrophotometry (GC-MS). The major constituents of the extracts were monoterpene hydrocarbons (91.75-93.75%[709.32-809.05 mg/100 g of fresh flavedo peel]) including limonene (43.08-45.13%[341.46-379.81 mg/100 g of fresh flavedo peel]), γ-terpinene (27.88-29.06%[219.90-245.86 mg/100 g of fresh flavedo peel]), and p-cymene (8.13-11.02%[61.47-97.22 mg/100 g of fresh flavedo peel]). The extraction process used was determined to be a decisive factor that affects the composition of key citrus aroma components, as well as the antioxidant activities of the Shiikuwasha fruit. Antioxidant capabilities of the extracts were examined by assay of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity and β-carotene bleaching inhibition. The cold-press extraction system may better retain the total phenolic content of the flavedo peel and display superior antioxidant activities, compared to the steam distillation extraction method. Shiikuwasha (Citrus depressa Hayata) is a type of small citrus fruit, and has been used as raw material for beverage and food additive productions in Japan. It had a unique aroma composition in which the limonene content of its peels is lower than that of other commonly known citrus peels. The present study detailed the volatile aroma composition, as well as antioxidant capabilities of Shiikuwasha peel extracts of different extraction methods, that are cold-press and steam distillation methods. The results of this study may provide a basis for selection of Shiikuwasha peel extracts in food industry for citrus flavor production. © 2012 Institute of Food Technologists®

Salinity alters curcumin, essential oil and chlorophyll of turmeric (Curcuma longa L.).

PubMed

Mostajeran, A; Gholaminejad, A; Asghari, G

2014-01-01

Turmeric (Curcuma longa L.) is a perennial rhizomatous plant from the family of Zingibraceae, native in South Asia. The main components of turmeric are curcuminoids and essential oil which are responsible for turmeric characteristic such as odor and taste. Due to the large areas of saline land in Iran and less information related to cultivation of turmeric, in this research, the effect of salinity on growth, curcumin and essential oil of turmeric was evaluated. Rhizomes were planted in coco peat and perlite for germination. Then uniform germinated rhizomes transferred to hydroponic condition containing Hoagland's solution. Two months old plants were exposed to salinity (0, 20, 60 and 100 mM NaCl) for two months via hydroponic media using Hoagland's solution. Then dry weight of different plant parts, chlorophyll, curcumin and essential oil components of turmeric were determined. The result indicated that, dry weight reductions in 100 mM NaCl were 191%, 141%, 56%, 30% in leaf, pseudo-stem, root and rhizome, respectively (This is almost equal to 6.9, 2.87, 0.34 and 0.23 mg plant(-1) mM(-1)NaCl reduction of dry weight, respectively). The reductions in chlorophyll a and b are almost 3.32 and 0.79 μg/gFW respectively due to one unit addition of NaCl (P < 0.05). The addition of curcumin of rhizome for four months old plant versus three months were almost 5 fold for 0 mM NaCl and 2 fold for 100 mM NaCl due to one month of delay in harvest. Low salinity has positive effect in curcumin production but higher salinity (higher than 60 mM) had adverse effect and causes 24% reduction of curcumin compared to control plants. There were more para-cymene and terpineol in volatile oils of turmeric rhizome than the other components, most of the volatile oil compounds were unchanged or varied slightly as salinity changed.

The effects of evaporating essential oils on indoor air quality

NASA Astrophysics Data System (ADS)

Su, Huey-Jen; Chao, Chung-Jen; Chang, Ho-Yuan; Wu, Pei-Chih

Essential oils, predominantly comprised of a group of aromatic chemicals, have attracted increasing attention as they are introduced into indoor environments through various forms of consumer products via different venues. Our study aimed to characterize the profiles and concentrations of emitted volatile organic compounds (VOCs) when evaporating essential oils indoors. Three popular essential oils in the market, lavender, eucalyptus, and tea tree, based on a nation-wide questionnaire survey, were tested. Specific aromatic compounds of interest were sampled during evaporating the essential oils, and analyzed by GC-MS. Indoor carbon monoxide (CO), carbon dioxide (CO 2), total volatile organic compounds (TVOCs), and particulate matters (PM 10) were measured by real-time, continuous monitors, and duplicate samples for airborne fungi and bacteria were collected in different periods of the evaporation. Indoor CO (average concentration 1.48 vs. 0.47 ppm at test vs. background), CO 2 (543.21 vs. 435.47 ppm), and TVOCs (0.74 vs. 0.48 ppm) levels have increased significantly after evaporating essential oils, but not the PM 10 (2.45 vs. 2.42 ppm). The anti-microbial activity on airborne microbes, an effect claimed by the use of many essential oils, could only be found at the first 30-60 min after the evaporation began as the highest levels of volatile components in these essential oils appeared to emit into the air, especially in the case of tea tree oil. High emissions of linalool (0.092-0.787 mg m -3), eucalyptol (0.007-0.856 mg m -3), D-limonene (0.004-0.153 mg m -3), ρ-cymene (0.019-0.141 mg m -3), and terpinene-4-ol-1 (0.029-0.978 mg m -3), all from the family of terpenes, were observed, and warranted for further examination for their health implications, especially for their potential contribution to the increasing indoor levels of secondary pollutants such as formaldehyde and secondary organic aerosols (SOAs) in the presence of ozone.

Effects of Bark Beetle Infestation on Secondary Organic Aerosol Precursors in the Western United States

NASA Astrophysics Data System (ADS)

Huff Hartz, K. E.; Amin, H.; Dodson, C.; Atkins, P. T.; Hallar, G.

2009-12-01

Bark beetles are a potentially destructive force in forest ecosytems; however, it is not known how insect attacks affect the atmosphere. Other insects, such as the weevil (Strophosoma melanogrammum) attacks on spruce trees in Denmark, have a significant local effect on monoterpene emissions. In fact, a single weevil induced a three-fold increase in monoterpene emission, and the response lasted for several weeks. Mountain pine bark beetles (Dendroctonus ponderosae) have infested the forests in the vicinity of Storm Peak Laboratory near Steamboat Springs, Colorado. Emissions were sampled from the headspace of bark at the trunk and from the tree branches in the canopy from bark beetle infested and healthy lodgepole pine (Pinus contorta var. latifolia) and Engelmann spruce (Picea engelmannii) trees. The emissions were collected onto scent traps, containing 110 mg of Porapak Q sorbent, using PAS-500 micro air samplers set to a 0.4 mL/min flow rate for two hours. After collection, the scent traps were spiked with a recovery standard, perdeutrated decane, and extracted with 1.5 mL hexanes (in three portions). The analytes in the extracts were separated and detected using gas chromatography/mass spectroscopy. The analytes were identified and quantified using calibration curves from authentic standards, and when authentic standards were not available, the NIST mass spectra library and Adams retention time indices were used. The samples from lodgepole pine trees suggest an enhancement in the 3-carene, beta-phellandrene, and estragole (methyl chavicol) emissions upon bark beetle infestation. The samples from the Engelmann spruce trees suggest an enhancement in the 1,4-cineole, p-cymene, and beta-phellandrene emissions upon bark beetle infestation. A shift in the type and the quantity of VOC emissions due to bark beetle infestation may lead increases in SOA from these forests, since potent SOA precursors are produced.

Antibacterial activity of Artemisia asiatica essential oil against some common respiratory infection causing bacterial strains and its mechanism of action in Haemophilus influenzae.

PubMed

Huang, Jiehui; Qian, Chao; Xu, Hongjie; Huang, Yanjie

2018-01-01

The main objective of the current study was to investigate the chemical composition of the essential oil of Artemisia asiatica together with investigating the antibacterial effects it exerts on several common respiratory infection causing bacteria including Haemophilus influenzae. Its mechanism of action was studied using various state-of-the-art assays like scanning electron microscopy, DNA, RNA and protein leakage assays, growth curve assays etc. The essential oil was extracted from the leaves of A. asiatica by supercritical CO 2 fluid extraction technology. Chemical composition of essential oils was analyzed by gas chromatography-mass-spectrometry (GC-MS). The antibacterial activity was evaluated against 6 bacteria by the paper disc diffusion method. The minimum inhibitory concentration (MIC) and minimum bactericide concentration (MBC) values of the essential oil were estimated by agar dilution method. The antibacterial mechanism was evaluated by growth curve, the integrity of cell membrane and scanning electronmicroscope (SEM). Gas chromatographic analysis of the A. asiatica essential oil led to the identification of 16 chemical constituents accounting for 97.2% of the total oil composition. The major components were found to be Piperitone, (z)-davanone, p-cymene and 1, 8-cineole. The essential oil showed maximum growth inhibition against Haemophilus influenzae with a zone of inhibition of 24.5 mm and MIC/MBC values of 1.9/4.5 mg/mL respectively. Bacteria treated with the essential oil led to a rapid decrease in the number of viable cells. On adding the essential oil of A. asiatica to the bacterial culture, the constituents of the bacterial cell got released into the medium and this cell constituent release increased with increasing doses of the essential oil. SEM showed that the bacterial cells treated with the essential oil showed damaged cell wall, deformed cell morphology and shrunken cells. Copyright © 2017. Published by Elsevier Ltd.

A Phagostimulant Blend for the Asian Citrus Psyllid.

PubMed

Lapointe, Stephen L; Hall, David G; George, Justin

2016-09-01

Chemical cues that elicit orientation by the Asian citrus psyllid, Diaphorina citri Kuwayama (Hemiptera: Liviidae), are of interest because it is the primary vector of the causal pathogen of citrus greening disease. Non-pesticidal control methods for D. citri remain a high priority for the citrus industry. While searching for semiochemicals that may be involved in orientation to host plants, we previously identified a blend of formic and acetic acids that stimulated substrate probing by D. citri. Here, we applied geometric mixture designs and response surface modeling to identify and optimize a 3-component blend that further increased the number of salivary sheaths produced by D. citri on a wax substrate containing a 3.5:1.6:1 blend of formic acid, acetic acid, and p-cymene, respectively. No evidence was found for remote orientation by D. citri adults through olfaction to the phagostimulant blends. Increased probing in response to the presence of phagostimulants in the wax matrix occurred after contact with the substrate. Yellow wax beads always attracted more D. citri adults and received more probes compared with white wax beads. Yellow beads containing the 3-component blend of phagostimulants were probed by D. citri 2 to 3 times more often compared with yellow beads alone. The phagostimulant effect also was tested by covering wax beads containing the 3-component blend with a plastic film to minimize olfaction or contact chemoreception by antennation. The plastic film did not affect the probing response, thus suggesting that chemosensation was associated with mouthparts and not olfactory receptors. Salivary sheaths produced in wax beads containing the phagostimulant blend were 4.5 times longer than sheaths produced in beads without tastants. This phenomenon might be used to improve a trap, design an attract-and-kill product, or enhance other means of managing D. citri and citrus greening disease.

Pyrolysis-gas chromatography-isotope ratio mass spectrometry for monitoring natural additives in polylactic acid active food packages.

PubMed

Llana-Ruíz-Cabello, M; Pichardo, S; Jiménez-Morillo, N T; González-Vila, F J; Guillamón, E; Bermúdez, J M; Aucejo, S; Camean, A M; González-Pérez, J A

2017-11-24

Compound-specific isotope analysis (CSIA) usually requires preparative steps (pretreatments, extraction, derivatization) to get amenable chromatographic analytes from bulk geological, biological or synthetic materials. Analytical pyrolysis (Py-GC/MS) can help to overcome such sample manipulation. This communication describe the results obtained by hyphenating analytical pyrolysis (Py-GC) with carbon isotope-ratio mass spectrometry (IRMS) for the analysis of a polylactic acid (PLA) a based bio-plastic extruded with variable quantities of a natural plant extract or oregano essential oil. The chemical structural information of pyrolysates was first determined by conventional analytical pyrolysis and the measure of δ 13 C in specific compounds was done by coupling a pyrolysis unit to a gas chromatograph connected to a continuous flow IRMS unit (Py-GC-C-IRMS). Using this Py-CSIA device it was possible to trace natural additives with depleted δ 13 C values produced by C3 photosystem vegetation (cymene: -26.7‰±2.52; terpinene: -27.1‰±0.13 and carvacrol: -27.5‰±1.80 from oregano and two unknown structures: -23.3‰±3.32 and -24.4‰±1.70 and butyl valerate: -24.1‰±3.55 from Allium spp.), within the naturally isotopically enriched bio-plastic backbone derived from corn (C4 vegetation) starch (cyclopentanones: -14.2‰±2.11; lactide enantiomers: -9.2‰±1.56 and larger polymeric units: -17.2‰±1.71). This is the first application of Py-CSIA to characterize a bio-plastic and is shown as a promising tool to study such materials, providing not only a fingerprinting, but also valuable information about the origin of the materials, allowing the traceability of additives and minimizing sample preparation. Copyright © 2017 Elsevier B.V. All rights reserved.

The effect of terpene enhancer lipophilicity on the percutaneous permeation of hydrocortisone formulated in HPMC gel systems.

PubMed

El-Kattan, A F; Asbill, C S; Michniak, B B

2000-04-05

The percutaneous permeation of hydrocortisone (HC) was investigated in hairless mouse skin after application of an alcoholic hydrogel using a diffusion cell technique. The formulations contained one of 12 terpenes, the selection of which was based on an increase in their lipophilicity (log P 1.06-5.36). Flux, cumulative receptor concentrations, skin content, and lag time of HC were measured over 24 h and compared with control gels (containing no terpene). Furthermore, HC skin content and the solubility of HC in the alcoholic hydrogel solvent mixture in the presence of terpene were determined, and correlated to the enhancing activity of terpenes. The in vitro permeation experiments with hairless mouse skin revealed that the terpene enhancers varied in their ability to enhance the flux of HC. Nerolidol which possessed the highest lipophilicity (log P = 5.36+/-0.38) provided the greatest enhancement for HC flux (35.3-fold over control). Fenchone (log P = 2.13+/-0.30) exhibited the lowest enhancement of HC flux (10.1-fold over control). In addition, a linear relationship was established between the log P of terpenes and the cumulative amount of HC in the receptor after 24 h (Q(24)). Nerolidol, provided the highest Q(24) (1733+/-93 microg/cm(2)), whereas verbenone produced the lowest Q(24) (653+/-105 microg/cm(2)). Thymol provided the lowest HC skin content (1151+/-293 microg/g), while cineole produced the highest HC skin content (18999+/-5666 microg/g). No correlation was established between the log P of enhancers and HC skin content. A correlation however, existed between the log P of terpenes and the lag time. As log P increased, a linear decrease in lag time was observed. Cymene yielded the shortest HC lag time, while fenchone produced the longest lag time. Also, the increase in the log P of terpenes resulted in a proportional increase in HC solubility in the formulation solvent mixture.

Selective Essential Oils from Spice or Culinary Herbs Have High Activity against Stationary Phase and Biofilm Borrelia burgdorferi.

PubMed

Feng, Jie; Zhang, Shuo; Shi, Wanliang; Zubcevik, Nevena; Miklossy, Judith; Zhang, Ying

2017-01-01

Although the majority of patients with acute Lyme disease can be cured with the standard 2-4 week antibiotic treatment, about 10-20% of patients continue suffering from chronic symptoms described as posttreatment Lyme disease syndrome. While the cause for this is debated, one possibility is that persister bacteria are not killed by the current Lyme antibiotics and remain active in the system. It has been reported that essential oils have antimicrobial activities and some have been used by patients with persisting Lyme disease symptoms. However, the activity of essential oils against the causative agent Borrelia burgdorferi ( B. burgdorferi ) has not been well studied. Here, we evaluated the activity of 34 essential oils against B. burgdorferi stationary phase culture as a model for persister bacteria. We found that not all essential oils had activity against the B. burgdorferi stationary phase culture, with top five essential oils (oregano, cinnamon bark, clove bud, citronella, and wintergreen) at a low concentration of 0.25% showing high anti-persister activity that is more active than the known persister drug daptomycin. Interestingly, some highly active essential oils were found to have excellent anti-biofilm ability as shown by their ability to dissolve the aggregated biofilm-like structures. The top three hits, oregano, cinnamon bark, and clove bud completely eradicated all viable cells without any regrowth in subculture in fresh medium, whereas but not citronella and wintergreen did not have this effect. Carvacrol was found to be the most active ingredient of oregano oil showing excellent activity against B. burgdorferi stationary phase cells, while other ingredients of oregano oil p-cymene and α-terpinene had no apparent activity. Future studies are needed to characterize and optimize the active essential oils in drug combination studies in vitro and in vivo and to address their safety and pharmacokinetic properties before they can be considered as a novel treatment of persistent Lyme disease.

Chemical composition and antioxidant, antimicrobial activities of the essential oils of Thymus marschallianus Will. and Thymus proximus Serg.

PubMed

Jia, H L; Ji, Q L; Xing, S L; Zhang, P H; Zhu, G L; Wang, X H

2010-01-01

Chemical composition and antioxidant, antimicrobial activities of the essential oils from Thymus marschallianus Will. and Thymus proximus Serg. growing in the wild in Xinjiang were studied. Samples were collected from the aerial parts of the plants with simultaneous distillation-extraction apparatus. The yields ranged between 1.22%+/- 0.01 and 0.16%+/- 0.01 (weight/dry weight), respectively, 53 and 60 kinds of volatiles, representing 99.6% and 99.7% of the essential oils, respectively, were identified in extracts from T. marschallianus and T. proximus by GC/MS analysis. The main components were Thymol (28.0% to 32.9%), p-Cymene (7.7% to 25.4%), and gamma-Terpinene (18.0% to 22.4%). Antioxidant activities of the oils were evaluated using metal chelating, reductive potential, 2,2-diphenyl-1-picrylhydrazyl, hydroxyl radical, and modified thiobarbituric acid reactive substances assay. Antimicrobial activities of the oils were investigated on Escherichia coli, Staphylococcus aureus, Bacillus subtilis, yeast, Rhizopus, and Penicillium. The inhibition zones (IZ) and minimum inhibitory concentration (MIC) values were 5.0 to 35.7 mm in diameter and 1.81 to 4.52 microL/mL, respectively. Due to the economical impacts of spoiled foods and the consumer's concerns over the safety of foods, a lot of attention has been paid to naturally derived compounds. Fresh and dried Thymus species as well as their processed products have been widely used as flavorings since ancient times; however, during the last few decades, they also have become a subject for a search of natural antioxidants and antimicrobial agents. Biological activities of Thymus essential oils depend on their chemical composition, which is determined by the genotype and influenced by environmental conditions. Recent studies have showed that Thymus species have strong antimicrobial and antioxidant activities. To the best of our knowledge, the properties of Thymus species growing wild in the Xinjiang have not been reported before.

Chemical composition and antibacterial properties of essential oil and fatty acids of different parts of Ligularia persica Boiss

PubMed Central

Mohadjerani, Maryam; Hosseinzadeh, Rahman; Hosseini, Maryam

2016-01-01

Objective: The objective of this research was to investigate the chemical composition and antibacterial activities of the fatty acids and essential oil from various parts of Ligularia persica Boiss (L. persica) growing wild in north of Iran. Materials and Methods: Essential oils were extracted by using Clevenger-type apparatus. Antibacterial activity was tested on two Gram-positive and two Gram-negative bacteria by using micro dilution method. Results: GC and GC∕MS analysis of the oils resulted in detection of 94%, 96%, 93%, 99% of the total essential oil of flowers, stems, roots and leaves, respectively. The main components of flowers oil were cis-ocimene (15.4%), β-myrcene (4.4%), β-ocimene (3.9%), and γ-terpinene (5.0%). The major constituents of stems oil were β-phellandrene (5.4%), β-cymene (7.0%), valencene (3.9%). The main compounds of root oil were fukinanolid (17.0%), α-phellandrene (11.5%) and Β-selinene (5.0%) and in the case of leaves oil were cis-ocimene (4.8%), β-ocimene (4.9%), and linolenic acid methyl ester (4.7%). An analysis by GC-FID and GC-MS on the fatty-acid composition of the different parts of L. persica showed that major components were linoleic acid (11.3-31.6%), linolenic acid (4.7-21.8%) and palmitic acid (7.2-23.2%). Saturated fatty acids were found in lower amounts than unsaturated ones. The least minimum inhibition concentration (MIC) of the L. persica was 7.16 μg/ml against Pseudomonas aeruginosa. Conclusion: Our study indicated that the essential oil from L. persica stems and flowers showed high inhibitory effect on the Gram negative bacteria. The results also showed that fatty acids from the stems and leaves contained a high amount of poly-unsaturated fatty acids (PUFAs). PMID:27462560

Essential oils from Schinus species of northwest Argentina: Composition and antifungal activity.

PubMed

Sampietro, Diego A; Belizana, Maria Melina E; Baptista, Zareath P Terán; Vattuone, Marta A; Catalán, Cesar A N

2014-07-01

The composition of the essential oils from leaves (Sal) and fruits of S. areira (Saf), and fruits of S. fasciculatus (Sff) and S. gracilipes (Sgf) were analyzed by GC/MS. The major compounds identified were sabinene (26.0 +/- 0.5%), bicyclogermacrene (14.5 +/- 0.4%), and E-citral (6.7+/- 0.2%) in Sal oil, limonene (27.7 +/- 0.7%), sabinene (16.0+/- 0.5%), beta-phellandrene (14.6 +/- 0.8%) and bicyclogermacrene (8.1 +/- 0.2%) in Saf oil, sabinene (22.7 +/- 0.6%), alpha-phellandrene (18.7 +/- 0.3%), beta-phellandrene (15.7 +/- 0.4%), and bicyclogermacrene (8.1 +/- 0.2%) in Sff oil and beta-pinene (25.4 +/- 0.8%), alpha-pinene (24.7 +/- 0.7%), and sabinene (13.6 +/- 0.4%) in Sgf oil.The antifungal activity of the four oils was evaluated on strains of Fusarium verticillioides and F. graminearum, and the results compared with the effect of epoxyconazole, pyraclostrobin and thyme oil. The Sff oil had the highest antifungal activity among the Schinus oils tested, with MIC100 (F. graminearum) = 6 per thousand and MIC100 (F. verticillioides) = 12 per thousand. A principal component analysis suggests that 9 constituents (alpha-thujene, alpha-terpinene, p-cymene, gamma-terpinene, terpinolene, 1-terpineol, alpha-calacorene, alpha-phellandrene, and terpinen-4-ol) explain the higher antifungal effect of Sff. The MIC100s of Schinus oils were on average 30-60 and 8.5-17 fold lower than those obtained for thyme oil on F. verticillioides and F. graminearum, respectively. In the case of commercial fungicides, their MIC100s were three orders of magnitude lower than those of Schinus oils. The last ones showed an additive interaction when assayed in mixtures with the commecial fungicides and thyme oil. The results suggest that the doses of fungicides required for control of the Fusarium species can be reduced when they are assayed in mixtures with the Schinus oils.

Chemical composition of essential oils and in vitro antioxidant activity of fresh and dry leaves crude extracts of medicinal plant of Lactuca Sativa L. native to Sultanate of Oman

PubMed Central

Al Nomaani, Rahma Said Salim; Hossain, Mohammad Amzad; Weli, Afaf Mohammed; Al-Riyami, Qasim; Al-Sabahi, Jamal Nasser

2013-01-01

Objective To isolate and analyse the chemical composition in the essential oils and free radical scavenging activity of different crude extracts from the fresh and dry leaves of vegetable plants of Lactuca sativa L. (L. sativa). Methods The essential oils and volatile chemical constituents were isolated from the fresh and dry leaves of L. sativa (lettuce) grown in Sultanate of Oman by hydro distillation method. The antioxidant activity of the crude extracts was carried out by well established free radical scavenging activity (DPPH) method. Results About 20 chemical compounds of different concentration representing 83.07% and 79.88% respectively were isolated and identified by gas chromatography-mass spectroscopy in the essential oils isolated from the fresh and dry leaves as α-pinene (5.11% and 4.05%), γ-cymene (2.07% and 1.92%), thymol (11.55% and 10.73%), durenol (52.00% and 49.79%), α-terpinene (1.66% and 1.34%), thymol acetate (0.99% and 0.67%), caryophyllene (2.11% and 1.98%), spathulenol (3.09% and 2.98%), camphene (4.11% and 3.65%), limonene (1.28% and 1.11%) representing these major chemical compounds. However, some other minor chemical constituents were also isolated and identified from the essential oil of lettuce including β-pinene, α-terpinolene, linalool, 4-terpineol, α-terpineol, o-methylthymol, L-alloaromadendrene and viridiflorene. Conclusions The chemical constituents in the essential oils from the locally grown lettuce were identified in the following classes or groups of chemical compounds such as monoterpenes, sesquiterpenes volatile organic compounds and their oxygenated hydrocarbons. Therefore, the essential oils and the crude extracts from Omani vegetable species of lettuce are active candidates which would be used as antioxidant, antifungal or antimicrobial agents in new drugs preparation for therapy of infectious diseases. PMID:23646297

Salinity alters curcumin, essential oil and chlorophyll of turmeric (Curcuma longa L.)

PubMed Central

Mostajeran, A.; Gholaminejad, A.; Asghari, G.

2014-01-01

Turmeric (Curcuma longa L.) is a perennial rhizomatous plant from the family of Zingibraceae, native in South Asia. The main components of turmeric are curcuminoids and essential oil which are responsible for turmeric characteristic such as odor and taste. Due to the large areas of saline land in Iran and less information related to cultivation of turmeric, in this research, the effect of salinity on growth, curcumin and essential oil of turmeric was evaluated. Rhizomes were planted in coco peat and perlite for germination. Then uniform germinated rhizomes transferred to hydroponic condition containing Hoagland's solution. Two months old plants were exposed to salinity (0, 20, 60 and 100 mM NaCl) for two months via hydroponic media using Hoagland's solution. Then dry weight of different plant parts, chlorophyll, curcumin and essential oil components of turmeric were determined. The result indicated that, dry weight reductions in 100 mM NaCl were 191%, 141%, 56%, 30% in leaf, pseudo-stem, root and rhizome, respectively (This is almost equal to 6.9, 2.87, 0.34 and 0.23 mg plant-1 mM-1NaCl reduction of dry weight, respectively). The reductions in chlorophyll a and b are almost 3.32 and 0.79 μg/gFW respectively due to one unit addition of NaCl (P < 0.05). The addition of curcumin of rhizome for four months old plant versus three months were almost 5 fold for 0 mM NaCl and 2 fold for 100 mM NaCl due to one month of delay in harvest. Low salinity has positive effect in curcumin production but higher salinity (higher than 60 mM) had adverse effect and causes 24% reduction of curcumin compared to control plants. There were more para-cymene and terpineol in volatile oils of turmeric rhizome than the other components, most of the volatile oil compounds were unchanged or varied slightly as salinity changed. PMID:25598799

Measured and Predicted Vapor Liquid Equilibrium of Ethanol-Gasoline Fuels with Insight on the Influence of Azeotrope Interactions on Aromatic Species Enrichment and Particulate Matter Formation in Spark Ignition Engines

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

Ratcliff, Matthew A; McCormick, Robert L; Burke, Stephen

A relationship has been observed between increasing ethanol content in gasoline and increased particulate matter (PM) emissions from direct injection spark ignition (DISI) vehicles. The fundamental cause of this observation is not well understood. One potential explanation is that increased evaporative cooling as a result of ethanol's high HOV may slow evaporation and prevent sufficient reactant mixing resulting in the combustion of localized fuel rich regions within the cylinder. In addition, it is well known that ethanol when blended in gasoline forms positive azeotropes which can alter the liquid/vapor composition during the vaporization process. In fact, it was shown recentlymore » through a numerical study that these interactions can retain the aromatic species within the liquid phase impeding the in-cylinder mixing of these compounds, which would accentuate PM formation upon combustion. To better understand the role of the azeotrope interactions on the vapor/liquid composition evolution of the fuel, distillations were performed using the Advanced Distillation Curve apparatus on carefully selected samples consisting of gasoline blended with ethanol and heavy aromatic and oxygenated compounds with varying vapor pressures, including cumene, p-cymene, 4-tertbutyl toluene, anisole, and 4-methyl anisole. Samples collected during the distillation indicate an enrichment of the heavy aromatic or oxygenated additive with an increase in initial ethanol concentration from E0 to E30. A recently developed distillation and droplet evaporation model is used to explore the influence of dilution effects versus azeotrope interactions on the aromatic species enrichment. The results suggest that HOV-cooling effects as well as aromatic species enrichment behaviors should be considered in future development of predictive indices to forecast the PM potential of fuels containing oxygenated compounds with comparatively high HOV.« less

Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand.

PubMed

Jovanović, Katarina K; Tanić, Miljana; Ivanović, Ivanka; Gligorijević, Nevenka; Dojčinović, Biljana P; Radulović, Siniša

2016-10-01

Ruthenium(II)-arene complexes are promising drug candidates for the therapy of solid tumors. In previous work, seven new compounds of the general formula [Ru(η 6 -p-cymene)(L 1-7 )Cl] were synthesized and characterized, of which the complex with L=isoquinoline-3-carboxylic acid (RuT 7 ) was two times as active on HeLa cells compared to normal cell line MRC-5, as indicated by IC 50 values determined after 48h of incubation (45.4±3.0 vs. 84.2±5.7μM, respectively). In the present study, cell cycle analysis of HeLa cells treated with RuT 7 showed S phase arrest and an increase in sub-G1 population. The apoptotic potential of the title compound was confirmed with the Annexin V-FITC/PI assay together with a morphological evaluation of cells using fluorescent microscopy. Analysis of the intracellular accumulation of ruthenium showed 8.9ng Ru/10 6 cells after 6h of incubation. To gain further insight in the molecular mechanism of action of RuT 7 on HeLa cells, a whole-transcriptome microarray gene expression analysis was performed. Analysis of functional categories and signaling and biochemical pathways associated with the response of HeLa cells to treatment with RuT 7 showed that it leads the cells through the intrinsic (mitochondrial) apoptotic pathway, via indirect DNA damage due to the action of reactive oxygen species, and through direct DNA binding of RuT 7 . Statistical analysis for enrichment of gene sets associated with known drug-induced toxicities identified fewer associated toxicity profiles in RuT 7 -treated cells compared to cisplatin treatment. Altogether these results provide the basis for further development of RuT 7 in animal and pre-clinical studies as a potential drug candidate. Copyright © 2016 Elsevier Inc. All rights reserved.

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.

Evaluation of the analgesic and anti-inflammatory effects of the essential oil of Lippia gracilis leaves.

PubMed

Mendes, S S; Bomfim, R R; Jesus, H C R; Alves, P B; Blank, A F; Estevam, C S; Antoniolli, A R; Thomazzi, S M

2010-06-16

The aim of the present study is to investigate the antinociceptive, anti-inflammatory, and antioxidant activities of essential oil (EO) of Lippia gracilis Schauer (Verbenaceae) leaves to support the medicinal uses claimed by folklore practitioners in the caatinga region (semi-arid) of Northeastern Brazil. The chemical composition and antinociceptive and anti-inflammatory activities of the EO of Lippia gracilis leaves (50-200 mg/kg) were investigated. Antinociceptive activity of the EO was evaluated by writhing test. Anti-inflammatory activity of the EO was evaluated using paw oedema and peritonitis methods. Oral treatment with the EO of Lippia gracilis leaves elicited inhibitory activity on acetic acid effect at 50, 100, and 200 mg/kg (30.33+/-2.36, 25.20+/-1.48, and 21.00+/-1.54 abdominal writhes, respectively, P<0.05), as compared with the control group (36.73+/-1.92 writhes). The compound acetylsalicylic acid (ASA, 300 mg/kg) inhibited the acetic acid-induced writhing (12.67+/-0.50 abdominal writhes, P<0.001). Carrageenan-induced oedema formation was reduced with the EO of Lippia gracilis leaves at 200 mg/kg (0.72+/-0.06 mL h, P<0.001) and by the reference compound ASA (300 mg/kg, 0.85+/-0.04 mL h, P<0.001), as compared with the control group (1.76+/-0.06 mL h). Leukocyte migration into the peritoneal cavity induced by carrageenan was reduced with the EO of Lippia gracilis leaves at 50, 100, and 200 mg/kg (13.81+/-0.61, 11.77+/-0.91, and 10.30+/-0.60 leukocytes x 10(6)/mL, respectively, P<0.01), and by the compound dexamethasone (2 mg/kg, 5.34+/-0.33 leukocytes x 10(6)/mL, P<0.001), as compared with the control group (16.71+/-0.54 leukocytes x 10(6)/mL). The analyses of the essential oil allowed the identification of Lippia gracilis as a thymol-p-cymene chemotype (32.68% and 17.82%, respectively). The EO of Lippia gracilis leaves shows antinociceptive and anti-inflammatory activities. Copyright 2010 Elsevier Ireland Ltd. All rights reserved.

In-vitro antimicrobial activity and identification of bioactive components using GC-MS of commercially available essential oils in Saudi Arabia.

PubMed

Ashraf, Syed Amir; Al-Shammari, Eyad; Hussain, Talib; Tajuddin, Shaikh; Panda, Bibhu Prasad

2017-11-01

This study was designed to evaluate antimicrobial activity and chemical composition of four different plant essential oils i.e. Ginger oil (GiO), Black seed oil (BSO), Oregano oil (OO) and Rose oil (RO) against different bacterial and fungal strains. Anti-microbial activities of selected essential oils were determined by the microbiological technique using Agar well diffusion assay. After in vitro study, most of the essential oils showed antimicrobial activity against all the selected pathogens. Among all the tested oils, GiO showed strong antimicrobial activity. GiO showed highest antimicrobial activity against Shigella (119.79%), Enteococcus hirae (110.61%) and Escherichia coli (106.02%), when compared with the tetracycline (50 µg/mL) activity. However, Antifungal activity of GiO was found to be present against Candida albicans and Aspergilluas flavus , when compared with clotrimazole (50 µg/mL) activity. Among all the selected bacteria, BSO showed maximum antimicrobial activity against the E. coli followed by Citrobacter freundii. Moreover, BSO had highest zone of inhibition against the C. ablicans (33.58%). OO indicated that, Shigella had the highest sensitivity (12.6 ± 0.58, 131.25%), followed by E. hirae (19.1 ± 0.61, 96.46%) and Salmonella typhi (15.2 ± 0.27, 83.06%) when compared with tetracycline activity. OO showed poor sensitivity against all the selected fungal strains. Furthermore, Gas Chromatography analysis revealed that, Gingerol (10.86%) was the chief chemical constituents found in GiO followed by α -Sesquiphellandrene (6.29%), Zingiberene (5.88%). While, BSO, OO and RO had higher percentage of p-Cymene (6.90%), Carvacrol (15.87%) and Citronellol (8.07%) respectively. The results exhibited that the essential oils used for this study was the richest source for antimicrobial activity which indicates the presence of broad spectrum antimicrobial compounds in these essential oils. Hence, essential oils and their components can be recommended for therapeutic purposes as source of an alternative medicine.

Orbital cortex neuronal responses during an odor-based conditioned associative task in rats.

PubMed

Yonemori, M; Nishijo, H; Uwano, T; Tamura, R; Furuta, I; Kawasaki, M; Takashima, Y; Ono, T

2000-01-01

Neuronal activity in the rat orbital cortex during discrimination of various odors [five volatile organic compounds (acetophenone, isoamyl acetate, cyclohexanone, p-cymene and 1,8-cineole), and food- and cosmetic-related odorants (black pepper, cheese, rose and perfume)] and other conditioned sensory stimuli (tones, light and air puff) was recorded and compared with behavioral responses to the same odors (black pepper, cheese, rose and perfume). In a neurophysiological study, the rats were trained to lick a spout that protruded close to its mouth to obtain sucrose or intracranial self-stimulation reward after presentation of conditioned stimuli. Of 150 orbital cortex neurons recorded during the task, 65 responded to one or more types of sensory stimuli. Of these, 73.8% (48/65) responded during presentation of an odor. Although the mean breadth of responsiveness (entropy) of the olfactory neurons based on the responses to five volatile organic compounds and air (control) was rather high (0.795), these stimuli were well discriminated in an odor space resulting from multidimensional scaling using Pearson's correlation coefficients between the stimuli. In a behavioral study, a rat was housed in an equilateral octagonal cage, with free access to food and choice among eight levers, four of which elicited only water (no odor, controls), and four of which elicited both water and one of four odors (black pepper, cheese, rose or perfume). Lever presses for each odor and control were counted. Distributions of these five stimuli (four odors and air) in an odor space derived from the multidimensional scaling using Pearson's correlation coefficients based on behavioral responses were very similar to those based on neuronal responses to the same five stimuli. Furthermore, Pearson's correlation coefficients between the same five stimuli based on the neuronal responses and those based on behavioral responses were significantly correlated. The results demonstrated a pivotal role of the rat orbital cortex in olfactory sensory processing and suggest that the orbital cortex is important in the manifestation of various motivated behaviors of the animals, including odor-guided motivational behaviors (odor preference).

Technological Evaluation of Emulsions Containing The Volatile Oil from Leaves of Plectranthus Amboinicus Lour

PubMed Central

Lopes, Pablo Queiroz; Carneiro, Fabíola Bernardo; de Sousa, Ana Letícia Braz; Santos, Sócrates Golziodo; Oliveira, Elquio Eleamen; Soares, Luiz Alberto Lira

2017-01-01

Background: Plectranthus amboinicus Lour is a species which is widespread throughout tropical countries where it is widely used against respiratory tract disorders such as bronchodilator, antitussive, and expectorant conditions. Objective: This study aims to characterize the essential oil of P. amboinicus (PaEO) and produce and evaluate emulsions containing PaEO. Materials and Methods: The essential oil was characterized by physical-chemical analyses for density, refractive index, 90% ethanol solubility, color, appearance, and identification by gas chromatography coupled to mass spectrometry detection. The emulsions were prepared following a hydrophile-lipophile balance [HLB] spreadsheet design from two nonionic surfactants (Span 80® and Tween 20®) producing HLB values ranging from 4.3 to 16.7. The products were stored at room temperature at 5°C. The emulsion stabilities were tested both in the long and short-term. Results: The PaEO was obtained by steam distillation and the total extraction was reached after 3 hours yielding of 0.2% (w/w). This essential oil was characterized by physicochemical analyses for density [1.5 g.ml-1], refraction index [0.9167], ethanol 90% solubility [1:2], color, and appearance (yellow/clear). Nineteen components were identified in the oil, among them the sesquiterpenes: carvacrol [33.50%], p-cymene [28.20%] and γ-terpinene [14.77%]. The emulsions obtained successfully showed, for the first time, HLB values for essential oils from Plectranthus amboinicus [15.7]. Conclusion: The experimental data shows a relationship between HLB values of the surfactant mixtures contributing to the emulsified systems production containing phytopharmaceuticals. Such an approach is of great importance to the development of lipid carriers for therapeutic drugs. SUMMARY The essential oil from leaves of Plectranthus amboinicus was extracted by steam distillation and characterized.The emulsions containing essential oil were produced and the stability was performed in the short and long term.The critical hydrophilic-lipophilic balance (HLB) of the essential oil was 15.7 and was achieved by the combination of surfactants (Tween 80® and Span 20®). Abbreviations used: PaEO: essential oil of P. amboinicus, HLB: hydrophilic-lipophilic balance, CI: Creaming Index, MET: micro-emultocrit technique PMID:28216901

Anti-spasmodic assessment of hydroalcoholic extract and essential oil of aerial part of Pycnocycla caespitosa Boiss. & Hausskn on rat ileum contractions.

PubMed

Sadraei, Hassan; Asghari, Gholamreza; Alipour, Mahdi

2016-01-01

Pycnocycla caespitosa is an essential oil-containing plant naturally growing in southwest of Iran. The extract of this plant has been used as remedy in traditional medicine. Another species of Pycnocyla (P. spinosa) possessed antispasmodic activity. The pharmacological objective of this study was to look for relaxant effect of hydroalcoholic extract and essential oil of P. caespitosa on rat isolated ileum contractions for comparison with loperamide. The essential oil and the hydroalcoholic extract were prepared by hydrodistillation and percolation techniques, respectively. For antispasmodic studies a section of rat ileum was suspended in an organ bath containing Tyrode's solution. The tissue was stimulated with electrical field stimulation (EFS), KCl (80 mM) and acetylcholine (ACh 0.5 μM). The tissue was kept under 1 g tension at 37°C and continuously gassed with O2. The essential oil content in the aerial parts of P. caespitosa was found to be 0.16 % ml/g. The essential oil was analyzed by gas chromatography and gas chromatography-mass spectrometry. Seventy constituents, representing 97 % of the oil were identified. The major components of the oil were carvacrol (7.1%), β-eudesmol (6.4 %), ρ-cymene (5.7%), caryophyllene oxide (3.6%), α-pinine (1.4%) and α-phelandrene (1.1%). The hydroalcoholic extract of P. caespitosa inhibited the response to KCl (IC50 = 48 ± 3 μg/ml), ACh (IC50 = 61 ± 14.7 μg/ml) and EFS (IC50 = 77 ± 17 μg/ml) in a concentration-dependent manner. The essential oil of P. caespitosa also inhibited rat ileum contractions. The IC50 values for KCl, ACh and EFS were 9.2 ± 1.2 μg/ml, 7.6 ± 0.8 μg/ml and 6.4 ± 0.8 μg/ml, respectively. The inhibitory effect of both the essential oil and the extract were reversible. This research confirms the anti-spasmodic activity of both the essential oil and the extract of P. caespitosa on smooth muscle contraction of ileum.

Framework fluxionality of organometallic oxides: synthesis, crystal structure, EXAFS, and DFT studies on [[Ru(eta6-arene)]4Mo4O16] complexes.

PubMed

Laurencin, Danielle; Garcia Fidalgo, Eva; Villanneau, Richard; Villain, Françoise; Herson, Patrick; Pacifico, Jessica; Stoeckli-Evans, Helen; Bénard, Marc; Rohmer, Marie-Madeleine; Süss-Fink, Georg; Proust, Anna

2004-01-05

Reactions of the molybdates Na(2)MoO4.2 H2O and (nBu(4)N)2[Mo2O7] with [[Ru(arene)Cl(2)](2)] (arene=C(6)H5CH3, 1,3,5-C6H3(CH3)(3), 1,2,4,5-C6H2(CH3)4) in water or organic solvents led to formation of the triple-cubane organometallic oxides [[Ru(eta(6)-arene)](4)Mo4O16], whose crystal and molecular structures were determined. Refluxing triple cubane [[Ru(eta(6)-C6H5CH3)](4)Mo4O16] in methanol caused partial isomerization to the windmill form. The two isomers of [[Ru(eta(6)-C6H5CH3)](4)Mo4O16] were characterized by Raman and Mo K-edge X-ray absorption spectroscopy (XAS), both in the solid-state and in solution. This triple-cubane isomer was also used as a spectroscopic model to account for isomerization of the p-cymene windmill [[Ru(eta(6)-1,4-CH3C6H4CH(CH3)2)](4)Mo4O16] in solution. Using both Raman and XAS techniques, we were then able to determine the ratio between the windmill and triple-cubane isomers in dichloromethane and in chloroform. Density functional calculations on [[Ru(eta(6)-arene)](4)Mo4O16] (arene=C6H6, C6H5CH3, 1,3,5-C6H3(CH3)3, 1,4-CH3C6H4CH(CH3)2, C6(CH3)6) suggest that the windmill form is intrinsically more stable, provided the complexes are assumed to be isolated. Intramolecular electrostatic interactions and steric bulk induced by substituted arenes were found to modulate but not to reverse the energy difference between the isomers. The stability of the triple-cubane isomers should therefore be accounted for by effects of the surroundings that induce a shift in the energy balance between both forms.

Metabolically speaking: Possible reasons behind the tolerance of 'Sugar Belle' mandarin hybrid to huanglongbing.

PubMed

Killiny, Nabil; Valim, Maria Filomena; Jones, Shelley E; Omar, Ahmad A; Hijaz, Faraj; Gmitter, Fred G; Grosser, Jude W

2017-07-01

Huanglongbing (HLB) is currently considered the most destructive disease of citrus. Since its spread to the Americas, HLB has killed millions of trees and caused a sharp decline in production in many citrus growing regions. With the continuous spread of HLB disease in Florida and worldwide, there is an urgent need for the development of commercial citrus cultivars with a strong tolerance to HLB. Interestingly, field observations showed that some of the recently released mandarin hybrids such as 'Sugar Belle' were tolerant to HLB. In this study, we investigated the volatile and non-volatile metabolites of greenhouse-grown 'Sugar Belle' mandarin and four of its ancestors in order to understand why 'Sugar Belle' mandarin is relatively tolerant to HLB. Leaf volatiles were directly extracted with hexane and analyzed using gas chromatography-mass spectrometry (GC-MS). Leaf polar metabolites were extracted with a mixture of methanol:water (1:1, v/v), derivatized to their trimethylsilyl ethers, and analyzed using GC-MS. Forty-seven volatile compounds and forty-two polar metabolites were detected in 'Sugar Belle' mandarin leaves and its ancestors. 'Sugar Belle' was high in several volatiles such as α-thujene, para-cymene, γ-terpinene, thymol, β-elemene, and (E)-β-caryophyllene. Some of these volatiles, especially thymol, β-elemene, and (E)-β-caryophyllene are known for their anti-microbial activity. In addition, 'Sugar Belle' mandarin was the highest in synephrine, benzoic acid, ferulic acid, caffeic acid, chiro-inositol, fructose, glucose, threonic acid, saccharic acid, and galactaric acid, and the second in threonine, malic acid, and myo-inositol compared to the ancestors. Phenolic compounds such as benzoic, ferulic, and caffeic acids may act as antibacterial agents, whereas others like sugar alcohols may protect 'Sugar Belle' mandarin from stress during pathogen attack. The tolerance of 'Sugar Belle' and other newly released mandarin hybrids should be further evaluated using greenhouse controlled studies. If tolerance of these hybrids is confirmed, they could be used to replace the traditionally susceptible cultivars. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Chemical Composition, Antioxidant, Anti-Inflammatory and Anti-Proliferative Activities of Essential Oils of Plants from Burkina Faso

PubMed Central

Bayala, Bagora; Bassole, Imaël Henri Nestor; Gnoula, Charlemagne; Nebie, Roger; Yonli, Albert; Morel, Laurent; Figueredo, Gilles; Nikiema, Jean-Baptiste; Lobaccaro, Jean-Marc A.; Simpore, Jacques

2014-01-01

This research highlights the chemical composition, antioxidant, anti-inflammatory and anti-proliferative activities of essential oils from leaves of Ocimum basilicum, Ocimum americanum, Hyptis spicigera, Lippia multiflora, Ageratum conyzoides, Eucalyptus camaldulensis and Zingiber officinale. Essential oils were analyzed by gas chromatography–mass spectrometry and gas chromatography–flame ionization detector. Major constituents were α-terpineol (59.78%) and β-caryophyllene (10.54%) for Ocimum basilicum; 1, 8-cineol (31.22%), camphor (12.730%), α-pinene (6.87%) and trans α-bergamotene (5.32%) for Ocimum americanum; β-caryophyllene (21%), α-pinene (20.11%), sabinene (10.26%), β-pinene (9.22%) and α-phellandrene (7.03%) for Hyptis spicigera; p-cymene (25.27%), β-caryophyllene (12.70%), thymol (11.88), γ-terpinene (9.17%) and thymyle acetate (7.64%) for Lippia multiflora; precocene (82.10%)for Ageratum conyzoides; eucalyptol (59.55%), α-pinene (9.17%) and limonene (8.76%) for Eucalyptus camaldulensis; arcurcumene (16.67%), camphene (12.70%), zingiberene (8.40%), β-bisabolene (7.83%) and β-sesquiphellandrène (5.34%) for Zingiber officinale. Antioxidant activities were examined using 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) methods. O. basilicum and L. multiflora exhibited the highest antioxidant activity in DPPH and ABTS tests, respectively. Anti-inflammatory properties were evaluated by measuring the inhibition of lipoxygenase activity and essential oil of Z. officinale was the most active. Anti-proliferative effect was assayed by the measurement of MTT on LNCaP and PC-3 prostate cancer cell lines, and SF-763 and SF-767 glioblastoma cell lines. Essential oils from A. conyzoides and L. multiflora were the most active on LNCaP and PC-3 cell lines, respectively. The SF-767 glioblastoma cell line was the most sensitive to O. basilicum and L. multiflora EOs while essential oil of A. conyzoides showed the highest activity on SF-763 cells. Altogether these results justify the use of these plants in traditional medicine in Burkina Faso and open a new field of investigation in the characterization of the molecules involved in anti-proliferative processes. PMID:24662935

Chemical composition, antioxidant, anti-inflammatory and anti-proliferative activities of essential oils of plants from Burkina Faso.

PubMed

Bayala, Bagora; Bassole, Imaël Henri Nestor; Gnoula, Charlemagne; Nebie, Roger; Yonli, Albert; Morel, Laurent; Figueredo, Gilles; Nikiema, Jean-Baptiste; Lobaccaro, Jean-Marc A; Simpore, Jacques

2014-01-01

This research highlights the chemical composition, antioxidant, anti-inflammatory and anti-proliferative activities of essential oils from leaves of Ocimum basilicum, Ocimum americanum, Hyptis spicigera, Lippia multiflora, Ageratum conyzoides, Eucalyptus camaldulensis and Zingiber officinale. Essential oils were analyzed by gas chromatography-mass spectrometry and gas chromatography-flame ionization detector. Major constituents were α-terpineol (59.78%) and β-caryophyllene (10.54%) for Ocimum basilicum; 1, 8-cineol (31.22%), camphor (12.730%), α-pinene (6.87%) and trans α-bergamotene (5.32%) for Ocimum americanum; β-caryophyllene (21%), α-pinene (20.11%), sabinene (10.26%), β-pinene (9.22%) and α-phellandrene (7.03%) for Hyptis spicigera; p-cymene (25.27%), β-caryophyllene (12.70%), thymol (11.88), γ-terpinene (9.17%) and thymyle acetate (7.64%) for Lippia multiflora; precocene (82.10%)for Ageratum conyzoides; eucalyptol (59.55%), α-pinene (9.17%) and limonene (8.76%) for Eucalyptus camaldulensis; arcurcumene (16.67%), camphene (12.70%), zingiberene (8.40%), β-bisabolene (7.83%) and β-sesquiphellandrène (5.34%) for Zingiber officinale. Antioxidant activities were examined using 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) methods. O. basilicum and L. multiflora exhibited the highest antioxidant activity in DPPH and ABTS tests, respectively. Anti-inflammatory properties were evaluated by measuring the inhibition of lipoxygenase activity and essential oil of Z. officinale was the most active. Anti-proliferative effect was assayed by the measurement of MTT on LNCaP and PC-3 prostate cancer cell lines, and SF-763 and SF-767 glioblastoma cell lines. Essential oils from A. conyzoides and L. multiflora were the most active on LNCaP and PC-3 cell lines, respectively. The SF-767 glioblastoma cell line was the most sensitive to O. basilicum and L. multiflora EOs while essential oil of A. conyzoides showed the highest activity on SF-763 cells. Altogether these results justify the use of these plants in traditional medicine in Burkina Faso and open a new field of investigation in the characterization of the molecules involved in anti-proliferative processes.

Distillation time alters essential oil yield, composition, and antioxidant activity of male Juniperus scopulorum trees.

PubMed

Zheljazkov, Valtcho D; Astatkie, Tess; Jeliazkova, Ekaterina A; Schlegel, Vicki

2012-01-01

The objective of this study was to evaluate the effect of 15 distillation times (DT), ranging from 1.25 to 960 min, on oil yield, essential oil profiles, and antioxidant capacity of male J. scopulorum trees. Essential oil yields were 0.07% at 1.25 min DT and reached a maximum of 1.48% at 840 min DT. The concentrations of alpha-thujene (1.76-2.75%), alpha-pinene (2.9-8.7%), sabinene (45-74.7%), myrcene (2.4-3.4%), and para-cymene (0.8-3.1%) were highest at the shortest DT (1.5 to 5 min) and decreased with increasing DT. Cis-sabinene hydrate (0.5-0.97%) and linalool plus trans-sabinene (0.56-1.6%) reached maximum levels at 40 min DT. Maximum concentrations of limonene (2.3-2.8%) and pregeijerene-B (0.06-1.4%) were obtained at 360-480 min DT, and 4-terpinenol (0.7-5.7%) at 480 min DT. Alpha-terpinene (0.16-2.9%), gamma-terpinene (0.3-4.9%) and terpinolene (0.3-1.4%) reached maximum at 720 min DT. The concentrations of delta-cadinene (0.06-1.65%), elemol (0-6.0%), and 8-alpha-acetoxyelemol (0-4.4%) reached maximum at 840 min DT. The yield of the essential oil constituents increased with increasing DT. Only linalool/transsabinene hydrate reached a maximum yield at 360 min DT. Maximum yields of the following constituents were obtained at 720 min DT: alpha-thujene, alpha-pinene, camphene, sabinene, myrcene, alpha-terpinene, para-cimene, limonene, gamma-terpinene, terpinolene, and 4-terpinenol. At 840 min DT, cis-sabinene hydrate, prejeijerene-B, gamma muurolene, delta-cadinene, reached maximum. At 960 min DT, maximum yields of beta-pinene, elemol, alphaeudesmol/betaeudesmol, 8-alpha-acetoxyelemol were reached. These changes were adequately modeled by either the Michaelis-Menten or the Power (Convex) nonlinear regression models. Oils from the 480 min DT showed higher antioxidant activity compared to samples collected at 40, 160, or 960 min DT. These results show the potential for obtaining essential oils with various compositions and antioxidant capacity from male J. scopulorum by varying DT. This study can be used as a reference paper for comparing results of reports where different lengths of the DT were used.

Identification of highly effective antitrypanosomal compounds in essential oils from the Apiaceae family.

PubMed

Ngahang Kamte, Stephane L; Ranjbarian, Farahnaz; Cianfaglione, Kevin; Sut, Stefania; Dall'Acqua, Stefano; Bruno, Maurizio; Afshar, Fariba Heshmati; Iannarelli, Romilde; Benelli, Giovanni; Cappellacci, Loredana; Hofer, Anders; Maggi, Filippo; Petrelli, Riccardo

2018-07-30

The Apiaceae family encompasses aromatic plants of economic importance employed in foodstuffs, beverages, perfumery, pharmaceuticals and cosmetics. Apiaceae are rich sources of essential oils because of the wealth of secretory structures (ducts and vittae) they are endowed with. The Apiaceae essential oils are available on an industrial level because of the wide cultivation and disposability of the bulky material from which they are extracted as well as their relatively cheap price. In the fight against protozoal infections, essential oils may represent new therapeutic options. In the present work, we focused on a panel of nine Apiaceae species (Siler montanum, Sison amomum, Echinophora spinosa, Kundmannia sicula, Crithmum maritimum, Helosciadium nodiflorum, Pimpinella anisum, Heracleum sphondylium and Trachyspermum ammi) and their essential oils as a model for the identification of trypanocidal compounds to be used as alternative/integrative therapies in the treatment of Human African trypanosomiasis (HAT) and as starting material for drug design. The evaluation of inhibitory effects of the Apiaceae essential oils against Trypanosoma brucei showed that some of them (E. spinosa, S. amomum, C. maritimum and H. nodiflorum) were active, with EC 50 in the range 2.7-10.7 μg/mL. Most of these oils were selective against T. brucei, except the one from C. maritimum that was highly selective against the BALB/3T3 mammalian cells. Testing nine characteristic individual components (α-pinene, sabinene, α-phellandrene, p-cymene, limonene, β-ocimene, γ-terpinene, terpinolene, and myristicin) of these oils, we showed that some of them had much higher selectivity than the oils themselves. Terpinolene was particularly active with an EC 50 value of 0.035 μg/mL (0.26 µM) and a selectivity index (SI) of 180. Four other compounds with EC 50 in the range 1.0-6.0 μg/mL (7.4-44 µM) had also good SI: α-pinene (>100), β-ocimene (>91), limonene (>18) and sabinene (>17). In conclusion, these results highlight that the essential oils from the Apiaceae family are a reservoir of substances to be used as leading compounds for the development of natural drugs for the treatment of HAT. Copyright © 2018 Elsevier Inc. All rights reserved.

Neuropharmacological effects of essential oil from the leaves of Croton conduplicatus Kunth and possible mechanisms of action involved.

PubMed

Oliveira Júnior, Raimundo Gonçalves de; Ferraz, Christiane Adrielly Alves; Silva, Juliane Cabral; de Andrade Teles, Roxana Braga; Silva, Mariana Gama; Diniz, Tâmara Coimbra; Dos Santos, Uiliane Soares; de Souza, Ana Valéria Vieira; Nunes, Carlos Eduardo Pereira; Salvador, Marcos José; Lorenzo, Vitor Prates; Quintans Júnior, Lucindo José; Almeida, Jackson Roberto Guedes da Silva

2018-07-15

Croton conduplicatus Kunth (Euphorbiaceae) is a Brazilian aromatic medicinal plant, widely known as "quebra-faca". In folk medicine, its leaves and stem-barks are used as a natural analgesic for the treatment of headaches. In this study, we describe for the first time the neuropharmacological potential of the essential oil obtained from the leaves of Croton conduplicatus (EO) in experimental models of pain, anxiety and insomnia. The mechanisms of action involved in these activities were also investigated. Different experimental models were used to evaluate the antinociceptive (acetic acid, formalin-induced nociception and hot plate tests), anxiolytic (elevated plus maze and hole board tests) and sedative (thiopental-induced sleeping time) effects of EO in mice. EO was evaluated in three different doses (25, 50 and 100 mg/kg, i.p.) and compared with positive and negative controls in all experimental protocols. When appropriate, animals were pretreated with pharmacological antagonists (naloxone, atropine and flumazenil) in order to evaluate the mechanisms of action involved. A docking study also was performed to identify possible targets involved. EO (25, 50 and 100 mg/kg, i.p.) demonstrated a significant antinociceptive activity in all experimental models. Pretreatment with naloxone or atropine reversed the antinociceptive response (p < 0.05), suggesting the involvement of opioid and muscarinic receptors, respectively. A docking study was performed with the major components identified in EO (1,8 cineole - 21.42%, spathulenol - 15.47%, p-cymene - 12.41% and caryophyllene oxide - 12.15%), demonstrating favorable interaction profile with different subtypes of muscarinic (M2, M3 and M4) and opioids (delta and mu) receptors. EO also showed anxiolytic (mainly at doses of 25 and 50 mg/kg, i.p.) and sedative (only at the dose of 100 mg/kg, i.p.) effects in mice. These pharmacological responses were reversed by flumazenil (p < 0.05), indicating possible involvement of GABA A receptors. Our findings support the traditional use of this plant as a natural analgesic and suggest that EO is a multi-target natural product, presenting not only antinociceptive effect but also anxiolytic and sedative activities depending on the dose used. Copyright © 2018 Elsevier B.V. All rights reserved.

Large drought-induced variations in oak leaf volatile organic compound emissions during PINOT NOIR 2012.

PubMed

Geron, Chris; Daly, Ryan; Harley, Peter; Rasmussen, Rei; Seco, Roger; Guenther, Alex; Karl, Thomas; Gu, Lianhong

2016-03-01

Leaf-level isoprene and monoterpene emissions were collected and analyzed from five of the most abundant oak (Quercus) species in Central Missouri's Ozarks Region in 2012 during PINOT NOIR (Particle Investigations at a Northern Ozarks Tower - NOx, Oxidants, Isoprene Research). June measurements, prior to the onset of severe drought, showed isoprene emission rates and leaf temperature responses similar to those previously reported in the literature and used in Biogenic Volatile Organic Compound (BVOC) emission models. During the peak of the drought in August, isoprene emission rates were substantially reduced, and response to temperature was dramatically altered, especially for the species in the red oak subgenus (Erythrobalanus). Quercus stellata (in the white oak subgenus Leucobalanus), on the other hand, increased its isoprene emission rate during August, and showed no decline at high temperatures during June or August, consistent with its high tolerance to drought and adaptation to xeric sites at the prairie-deciduous forest interface. Mid-late October measurements were conducted after soil moisture recharge, but were affected by senescence and cooler temperatures. Isoprene emission rates were considerably lower from all species compared to June and August data. The large differences between the oaks in response to drought emphasizes the need to consider BVOC emissions at the species level instead of just the whole canopy. Monoterpene emissions from Quercus rubra in limited data were highest among the oaks studied, while monoterpene emissions from the other oak species were 80-95% lower and less than assumed in current BVOC emission models. Major monoterpenes from Q. rubra (and in ambient air) were p-cymene, α-pinene, β-pinene, d-limonene, γ-terpinene, β-ocimene (predominantly1,3,7-trans-β-ocimene, but also 1,3,6-trans-β-ocimene), tricyclene, α-terpinene, sabinene, terpinolene, and myrcene. Results are discussed in the context of canopy flux studies conducted at the site during PINOT NOIR, which are described elsewhere. The leaf isoprene emissions before and during the drought were consistent with above canopy fluxes, while leaf and branch monoterpene emissions were an order of magnitude lower than the observed above canopy fluxes, implying that other sources may be contributing substantially to monoterpene fluxes at this site. This strongly demonstrates the need for further simultaneous canopy and enclosure BVOC emission studies. Published by Elsevier Ltd.

Chemical composition and insecticidal activity of plant essential oils from Benin against Anopheles gambiae (Giles)

PubMed Central

2013-01-01

Background Insecticide resistance in sub-Saharan Africa and especially in Benin is a major public health issue hindering the control of the malaria vectors. Each Anopheles species has developed a resistance to one or several classes of the insecticides currently in use in the field. Therefore, it is urgent to find alternative compounds to conquer the vector. In this study, the efficacies of essential oils of nine plant species, which are traditionally used to avoid mosquito bites in Benin, were investigated. Methods Essential oils of nine plant species were extracted by hydrodistillation, and their chemical compositions were identified by GC-MS. These oils were tested on susceptible “kisumu” and resistant “ladji-Cotonou” strains of Anopheles gambiae, following WHO test procedures for insecticide resistance monitoring in malaria vector mosquitoes. Results Different chemical compositions were obtained from the essential oils of the plant species. The major constituents identified were as follows: neral and geranial for Cymbopogon citratus, Z-carveol, E-p-mentha-1(7),8-dien-2-ol and E-p-mentha-2,8-dienol for Cymbopogon giganteus, piperitone for Cymbopogon schoenanthus, citronellal and citronellol for Eucalyptus citriodora, p-cymene, caryophyllene oxide and spathulenol for Eucalyptus tereticornis, 3-tetradecanone for Cochlospermum tinctorium and Cochlospermum planchonii, methyl salicylate for Securidaca longepedunculata and ascaridole for Chenopodium ambrosioides. The diagnostic dose was 0.77% for C. citratus, 2.80% for E. tereticornis, 3.37% for E. citriodora, 4.26% for C. ambrosioides, 5.48% for C. schoenanthus and 7.36% for C. giganteus. The highest diagnostic doses were obtained with S. longepedunculata (9.84%), C. tinctorium (11.56%) and C. planchonii (15.22%), compared to permethrin 0.75%. A. gambiae cotonou, which is resistant to pyrethroids, showed significant tolerance to essential oils from C. tinctorium and S. longepedunculata as expected but was highly susceptible to all the other essential oils at the diagnostic dose. Conclusions C. citratus, E. tereticornis, E. citriodora, C. ambrosioides and C. schoenanthus are potential promising plant sources for alternative compounds to pyrethroids, for the control of the Anopheles malaria vector in Benin. The efficacy of their essential oils is possibly based on their chemical compositions in which major and/or minor compounds have reported insecticidal activities on various pests and disease vectors such as Anopheles. PMID:24298981

Composition, antimicrobial, antioxidant, and antiproliferative activity of Origanum dictamnus (dittany) essential oil

PubMed Central

Mitropoulou, Gregoria; Fitsiou, Eleni; Stavropoulou, Elisavet; Papavassilopoulou, Eleni; Vamvakias, Manolis; Pappa, Aglaia; Oreopoulou, Antigoni; Kourkoutas, Yiannis

2015-01-01

Background Nowadays, there has been an increased interest in essential oils from various plant origins as potential antimicrobial, antioxidant, and antiproliferative agents. This trend can be mainly attributed to the rising number and severity of food poisoning outbreaks worldwide along with the recent negative consumer perception against artificial food additives and the demand for novel functional foods with possible health benefits. Origanum dictamnus (dittany) is an aromatic, tender perennial plant that only grows wild on the mountainsides and gorges of the island of Crete in Greece. Objective The aim of the present study was to investigate the antimicrobial, antioxidant, and antiproliferative properties of O. dictamnus essential oil and its main components and assess its commercial potential in the food industry. Design O. dictamnus essential oil was initially analyzed by gas chromatography–mass spectrometry (GC–MS) to determine semi-quantitative chemical composition of the essential oils. Subsequently, the antimicrobial properties were assayed and the minimum inhibitory and non-inhibitory concentration values were determined. The antioxidant activity and cytotoxic action against the hepatoma adenocarcinoma cell line HepG2 of the essential oil and its main components were further evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and by the sulforhodamine B (SRB) assay, respectively. Results The main constituents of O. dictamnus essential oil identified by GC–MS analysis were carvacrol (52.2%), γ-terpinene (8.4%), p-cymene (6.1%), linalool (1.4%), and caryophyllene (1.3%). O. dictamnus essential oil and its main components were effective against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Listeria monocytogenes, Salmonella Enteritidis, Salmonella typhimurium, Saccharomyces cerevisiae, and Aspergillus niger. In addition, the estimated IC50 value for the DPPH radical scavenging activity for O. dictamnus essential oil was 0.045±0.0042% (v/v) and was mainly attributed to carvacrol. The EC50 value for the essential oil in the 72h SRB assay in HepG2 cells was estimated to be 0.0069±0.00014% (v/v). Among the individual constituents tested, carvacrol was the most bioactive compound and accounted for the observed antiproliferative activity of the essential oil. Conclusions The results revealed that O. dictamnus essential oil is a noteworthy growth inhibitor against the microbes studied. It also possesses significant antioxidant activity and demonstrated excellent cytotoxicity against HepG2 cells. Taken together, O. dictamnus essential oil may represent an effective and inexpensive source of potent natural antimicrobial agents with health-promoting properties, which may be incorporated in food systems. PMID:25952773

Bipyrimidine ruthenium(II) arene complexes: structure, reactivity and cytotoxicity.

PubMed

Betanzos-Lara, Soledad; Novakova, Olga; Deeth, Robert J; Pizarro, Ana M; Clarkson, Guy J; Liskova, Barbora; Brabec, Viktor; Sadler, Peter J; Habtemariam, Abraha

2012-10-01

The synthesis and characterization of complexes [(η(6)-arene)Ru(N,N')X][PF(6)], where arene is para-cymene (p-cym), biphenyl (bip), ethyl benzoate (etb), hexamethylbenzene (hmb), indane (ind) or 1,2,3,4-tetrahydronaphthalene (thn), N,N' is 2,2'-bipyrimidine (bpm) and X is Cl, Br or I, are reported, including the X-ray crystal structures of [(η(6)-p-cym)Ru(bpm)I][PF(6)], [(η(6)-bip)Ru(bpm)Cl][PF(6)], [(η(6)-bip)Ru(bpm)I][PF(6)] and [(η(6)-etb)Ru(bpm)Cl][PF(6)]. Complexes in which N,N' is 1,10-phenanthroline (phen), 1,10-phenanthroline-5,6-dione or 4,7-diphenyl-1,10-phenanthroline (bathophen) were studied for comparison. The Ru(II) arene complexes undergo ligand-exchange reactions in aqueous solution at 310 K; their half-lives for hydrolysis range from 14 to 715 min. Density functional theory calculations on [(η(6)-p-cym)Ru(bpm)Cl][PF(6)], [(η(6)-p-cym)Ru(bpm)Br][PF(6)], [(η(6)-p-cym)Ru(bpm)I][PF(6)], [(η(6)-bip)Ru(bpm)Cl][PF(6)], [(η(6)-bip)Ru(bpm)Br][PF(6)] and [(η(6)-bip)Ru(bpm)I][PF(6)] suggest that aquation occurs via an associative pathway and that the reaction is thermodynamically favourable when the leaving ligand is I > Br ≈ Cl. pK (a)* values for the aqua adducts of the complexes range from 6.9 to 7.32. A binding preference for 9-ethylguanine (9-EtG) compared with 9-ethyladenine (9-EtA) was observed for [(η(6)-p-cym)Ru(bpm)Cl][PF(6)], [(η(6)-hmb)Ru(bpm)Cl](+), [(η(6)-ind)Ru(bpm)Cl](+), [(η(6)-thn)Ru(bpm)Cl](+), [(η(6)-p-cym)Ru(phen)Cl](+) and [(η(6)-p-cym)Ru(bathophen)Cl](+) in aqueous solution at 310 K. The X-ray crystal structure of the guanine complex [(η(6)-p-cym)Ru(bpm)(9-EtG-N7)][PF(6)](2) shows multiple hydrogen bonding. Density functional theory calculations show that the 9-EtG adducts of all complexes are thermodynamically preferred compared with those of 9-EtA. However, the bmp complexes are inactive towards A2780 human ovarian cancer cells. Calf thymus DNA interactions for [(η(6)-p-cym)Ru(bpm)Cl][PF(6)] and [(η(6)-p-cym)Ru(phen)Cl][PF(6)] consist of weak coordinative, intercalative and monofunctional coordination. Binding to biomolecules such as glutathione may play a role in deactivating the bpm complexes.

Composition, antimicrobial, antioxidant, and antiproliferative activity of Origanum dictamnus (dittany) essential oil.

PubMed

Mitropoulou, Gregoria; Fitsiou, Eleni; Stavropoulou, Elisavet; Papavassilopoulou, Eleni; Vamvakias, Manolis; Pappa, Aglaia; Oreopoulou, Antigoni; Kourkoutas, Yiannis

2015-01-01

Nowadays, there has been an increased interest in essential oils from various plant origins as potential antimicrobial, antioxidant, and antiproliferative agents. This trend can be mainly attributed to the rising number and severity of food poisoning outbreaks worldwide along with the recent negative consumer perception against artificial food additives and the demand for novel functional foods with possible health benefits. Origanum dictamnus (dittany) is an aromatic, tender perennial plant that only grows wild on the mountainsides and gorges of the island of Crete in Greece. The aim of the present study was to investigate the antimicrobial, antioxidant, and antiproliferative properties of O. dictamnus essential oil and its main components and assess its commercial potential in the food industry. O. dictamnus essential oil was initially analyzed by gas chromatography-mass spectrometry (GC-MS) to determine semi-quantitative chemical composition of the essential oils. Subsequently, the antimicrobial properties were assayed and the minimum inhibitory and non-inhibitory concentration values were determined. The antioxidant activity and cytotoxic action against the hepatoma adenocarcinoma cell line HepG2 of the essential oil and its main components were further evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and by the sulforhodamine B (SRB) assay, respectively. The main constituents of O. dictamnus essential oil identified by GC-MS analysis were carvacrol (52.2%), γ-terpinene (8.4%), p-cymene (6.1%), linalool (1.4%), and caryophyllene (1.3%). O. dictamnus essential oil and its main components were effective against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Listeria monocytogenes, Salmonella Enteritidis, Salmonella typhimurium, Saccharomyces cerevisiae, and Aspergillus niger. In addition, the estimated IC50 value for the DPPH radical scavenging activity for O. dictamnus essential oil was 0.045±0.0042% (v/v) and was mainly attributed to carvacrol. The EC50 value for the essential oil in the 72h SRB assay in HepG2 cells was estimated to be 0.0069±0.00014% (v/v). Among the individual constituents tested, carvacrol was the most bioactive compound and accounted for the observed antiproliferative activity of the essential oil. The results revealed that O. dictamnus essential oil is a noteworthy growth inhibitor against the microbes studied. It also possesses significant antioxidant activity and demonstrated excellent cytotoxicity against HepG2 cells. Taken together, O. dictamnus essential oil may represent an effective and inexpensive source of potent natural antimicrobial agents with health-promoting properties, which may be incorporated in food systems.

Knockdown and larvicidal activity of six monoterpenes against Aedes aegypti (Diptera: Culicidae) and their structure-activity relationships.

PubMed

Lucia, Alejandro; Zerba, Eduardo; Masuh, Hector

2013-12-01

The relationships between physicochemical parameters of majority components of Eucalyptus essential oils and their insecticide effect were evaluated on Aedes aegypti (L.) (Diptera: Culicidae). The octanol-water partition coefficients of the monoterpenes were estimated by the atom/fragment contribution method and the vapor pressures were determined by our laboratory in previous studies. The larvicidal activity (LC50 (ppm)) and knockdown effect (KT50 (min)) of each component was determined. The results show that the toxicity of EOs main components of Eucalyptus on adults and larvae of A. aegypti is strongly related to their physicochemical properties (vapor pressure and Log P). However, the interaction of both variables (vapor pressure * Log P) explains the toxicological phenomenon more precisely. The regression models were expressed as follows: KT 50(min) =  - 10.9 + 3.7 * Log P + 1.9 * 1/Pvapor (R(2) = 0.80; F = 42.5) and LC 50(ppm) =  - 94.3 + 438.6 *  1/Log P + 2.8 *  1/Pvapor (F = 57.8; R(2) = 0.85). The six evaluated components present different functional groups. Therefore, it was considered to evaluate the monoterpenes as a group and separated in two groups: oxygenated monoterpenes (α-terpineol, 4-terpineol, and 1,8-cineole) and terpene hydrocarbons (γ-terpinene, p-cymene, and α-pinene). The results show the regression models for each group as follows: (A) oxygenated terpenes: KT 50(min) = - 515.3 + 1613.2 * 1/Log P + 5, 2 * 1/Pvapor (F = 3176.7 R(2) = 0.99) and LC 50(ppm)  =  - 1679.4 + 5402.1 * 1/Log P + 12.7 *  1/Pvapor (F = 282.9; R(2) = 0.99). (B) Hydrocarbons terpenes: KT 50(min) = 18.2 - 58.3 * 1/Log P + 2.7 * 1/Pvapor (F = 171.7;  R(2) = 0.97) and LC 50(ppm) = - 21.1 + 174.9 * 1/Log P - 14.3 * 1/Pvapor (F = 410.0; R(2) = 0.99). The association between the toxic effect of the evaluated monoterpenes against A. aegypti and the physicochemical properties can be better described when they are separated into functional groups (hydrocarbons vs. oxygenated terpenes).

Tunisian Salvia officinalis L. and Schinus molle L. essential oils: their chemical compositions and their preservative effects against Salmonella inoculated in minced beef meat.

PubMed

Hayouni, El Akrem; Chraief, Imed; Abedrabba, Manaf; Bouix, Marielle; Leveau, Jean-Yves; Mohammed, Hammami; Hamdi, Moktar

2008-07-31

The essential oils (EOs) extracted from the aerial parts of cultivated Salvia officinalis L. and the berries of Schinus molle L. were analysed by gas chromatography-mass spectrometry (GC-MS) and 68 and 67 constituents were identified, respectively. The major constituents were 1,8-cineole (33.27%), beta-thujone (18.40%), alpha-thujone (13.45%), borneol (7.39%) in S. officinalis oil and alpha-phellandrene (35.86%), beta-phellandrene (29.3%), beta-pinene (15.68%), p-cymene (5.43%) and alpha-pinene (5.22%) in S. molle oil. In its second part, the present study was conducted to evaluate the in vitro antimicrobial activity of both studied EOs. For this purpose, paper disc-diffusion method and broth microdilution test were used. The disc-diffusion method showed significant zone of lysis against all the pathogens studied (gram-negative and gram-positive bacteria, yeast). These activities remained stable after six months, and decreased approximately by 20% after one year of storage of the EOs at 4 to 7 degrees C. On comparing the efficiency of both EOs, S. officinalis EO exhibited higher antibacterial activity against the majority of strains and especially against Candida albicans (two fold more active according to the inhibition zones values). The minimal inhibitory concentrations (MICs) were reported between 4.5 mg/ml and 72 mg/ml on nutrient broth. The particular chemotype of each EO may be involved in its specific antimicrobial behaviour. Furthermore, the inhibitory effect of these EOs were evaluated against two foodborne pathogens belonging to Salmonella genus, experimentally inoculated (10(3) CFU/g) in minced beef meat, which was mixed with different concentrations of the EO and stored at 4 to 7 degrees C for 15 days. Although the antibacterial activities of both EOs in minced beef meat were clearly evident, their addition had notable effects on the flavour and taste of the meat at concentrations more than 2% for S. molle and 1.5% for S. officinalis. One solution to the above-mentioned problem may be the use of combinations of different food preservation systems. In this context, each of the EOs has been used along with low water activity (addition of NaCl) in addition to low refrigeration temperatures. Results on the Salmonella growth showed that some combinations could be recommended to eliminate germs from minced raw beef. By using this method, a stable and, from a microbiological point of view, safe meat can be produced without substantial loss in sensory quality. Results obtained herein, may suggest that the EOs of S. officinalis and S. molle possess antimicrobial activity, and therefore, they can be used in biotechnological fields as natural preservative ingredients in food and/or pharmaceutical industry.

Iridium and Ruthenium Complexes of N-Heterocyclic Carbene- and Pyridinol-Derived Chelates as Catalysts for Aqueous Carbon Dioxide Hydrogenation and Formic Acid Dehydrogenation: The Role of the Alkali Metal

PubMed Central

2017-01-01

Hydrogenation reactions can be used to store energy in chemical bonds, and if these reactions are reversible, that energy can be released on demand. Some of the most effective transition metal catalysts for CO2 hydrogenation have featured pyridin-2-ol-based ligands (e.g., 6,6′-dihydroxybipyridine (6,6′-dhbp)) for both their proton-responsive features and for metal–ligand bifunctional catalysis. We aimed to compare bidentate pyridin-2-ol based ligands with a new scaffold featuring an N-heterocyclic carbene (NHC) bound to pyridin-2-ol. Toward this aim, we have synthesized a series of [Cp*Ir(NHC-pyOR)Cl]OTf complexes where R = tBu (1), H (2), or Me (3). For comparison, we tested analogous bipy-derived iridium complexes as catalysts, specifically [Cp*Ir(6,6′-dxbp)Cl]OTf, where x = hydroxy (4Ir) or methoxy (5Ir); 4Ir was reported previously, but 5Ir is new. The analogous ruthenium complexes were also tested using [(η6-cymene)Ru(6,6′-dxbp)Cl]OTf, where x = hydroxy (4Ru) or methoxy (5Ru); 4Ru and 5Ru were both reported previously. All new complexes were fully characterized by spectroscopic and analytical methods and by single-crystal X-ray diffraction for 1, 2, 3, 5Ir, and for two [Ag(NHC-pyOR)2]OTf complexes 6 (R = tBu) and 7 (R = Me). The aqueous catalytic studies of both CO2 hydrogenation and formic acid dehydrogenation were performed with catalysts 1–5. In general, NHC-pyOR complexes 1–3 were modest precatalysts for both reactions. NHC complexes 1–3 all underwent transformations under basic CO2 hydrogenation conditions, and for 3, we trapped a product of its transformation, 3SP, which we characterized crystallographically. For CO2 hydrogenation with base and dxbp-based catalysts, we observed that x = hydroxy (4Ir) is 5–8 times more active than x = methoxy (5Ir). Notably, ruthenium complex 4Ru showed 95% of the activity of 4Ir. For formic acid dehydrogenation, the trends were quite different with catalytic activity showing 4Ir ≫ 4Ru and 4Ir ≈ 5Ir. Secondary coordination sphere effects are important under basic hydrogenation conditions where the OH groups of 6,6′-dhbp are deprotonated and alkali metals can bind and help to activate CO2. Computational DFT studies have confirmed these trends and have been used to study the mechanisms of both CO2 hydrogenation and formic acid dehydrogenation. PMID:29540958

Iridium and Ruthenium Complexes of N-Heterocyclic Carbene- and Pyridinol-Derived Chelates as Catalysts for Aqueous Carbon Dioxide Hydrogenation and Formic Acid Dehydrogenation: The Role of the Alkali Metal.

PubMed

Siek, Sopheavy; Burks, Dalton B; Gerlach, Deidra L; Liang, Guangchao; Tesh, Jamie M; Thompson, Courtney R; Qu, Fengrui; Shankwitz, Jennifer E; Vasquez, Robert M; Chambers, Nicole; Szulczewski, Gregory J; Grotjahn, Douglas B; Webster, Charles Edwin; Papish, Elizabeth T

2017-03-27

Hydrogenation reactions can be used to store energy in chemical bonds, and if these reactions are reversible, that energy can be released on demand. Some of the most effective transition metal catalysts for CO 2 hydrogenation have featured pyridin-2-ol-based ligands (e.g., 6,6'-dihydroxybipyridine (6,6'-dhbp)) for both their proton-responsive features and for metal-ligand bifunctional catalysis. We aimed to compare bidentate pyridin-2-ol based ligands with a new scaffold featuring an N -heterocyclic carbene (NHC) bound to pyridin-2-ol. Toward this aim, we have synthesized a series of [Cp*Ir(NHC-py OR )Cl]OTf complexes where R = t Bu ( 1 ), H ( 2 ), or Me ( 3 ). For comparison, we tested analogous bipy-derived iridium complexes as catalysts, specifically [Cp*Ir(6,6'-dxbp)Cl]OTf, where x = hydroxy ( 4 Ir ) or methoxy ( 5 Ir ); 4 Ir was reported previously, but 5 Ir is new. The analogous ruthenium complexes were also tested using [(η 6 -cymene)Ru(6,6'-dxbp)Cl]OTf, where x = hydroxy ( 4 Ru ) or methoxy ( 5 Ru ); 4 Ru and 5 Ru were both reported previously. All new complexes were fully characterized by spectroscopic and analytical methods and by single-crystal X-ray diffraction for 1 , 2 , 3 , 5 Ir , and for two [Ag(NHC-py OR ) 2 ]OTf complexes 6 (R = t Bu) and 7 (R = Me). The aqueous catalytic studies of both CO 2 hydrogenation and formic acid dehydrogenation were performed with catalysts 1 - 5 . In general, NHC-py OR complexes 1 - 3 were modest precatalysts for both reactions. NHC complexes 1 - 3 all underwent transformations under basic CO 2 hydrogenation conditions, and for 3 , we trapped a product of its transformation, 3 SP , which we characterized crystallographically. For CO 2 hydrogenation with base and dxbp-based catalysts, we observed that x = hydroxy ( 4 Ir ) is 5-8 times more active than x = methoxy ( 5 Ir ). Notably, ruthenium complex 4 Ru showed 95% of the activity of 4 Ir . For formic acid dehydrogenation, the trends were quite different with catalytic activity showing 4 Ir ≫ 4 Ru and 4 Ir ≈ 5 Ir . Secondary coordination sphere effects are important under basic hydrogenation conditions where the OH groups of 6,6'-dhbp are deprotonated and alkali metals can bind and help to activate CO 2 . Computational DFT studies have confirmed these trends and have been used to study the mechanisms of both CO 2 hydrogenation and formic acid dehydrogenation.

Investigation of urinary volatile organic metabolites as potential cancer biomarkers by solid-phase microextraction in combination with gas chromatography-mass spectrometry

PubMed Central

Silva, C L; Passos, M; Câmara, J S

2011-01-01

Background: Non-invasive diagnostic strategies aimed at identifying biomarkers of cancer are of great interest for early cancer detection. Urine is potentially a rich source of volatile organic metabolites (VOMs) that can be used as potential cancer biomarkers. Our aim was to develop a generally reliable, rapid, sensitive, and robust analytical method for screening large numbers of urine samples, resulting in a broad spectrum of native VOMs, as a tool to evaluate the potential of these metabolites in the early diagnosis of cancer. Methods: To investigate urinary volatile metabolites as potential cancer biomarkers, urine samples from 33 cancer patients (oncological group: 14 leukaemia, 12 colorectal and 7 lymphoma) and 21 healthy (control group, cancer-free) individuals were qualitatively and quantitatively analysed. Dynamic solid-phase microextraction in headspace mode (dHS-SPME) using a carboxen-polydimethylsiloxane (CAR/PDMS) sorbent in combination with GC-qMS-based metabolomics was applied to isolate and identify the volatile metabolites. This method provides a potential non-invasive method for early cancer diagnosis as a first approach. To fulfil this objective, three important dHS-SPME experimental parameters that influence extraction efficiency (fibre coating, extraction time and temperature of sampling) were optimised using a univariate optimisation design. The highest extraction efficiency was obtained when sampling was performed at 50°C for 60 min using samples with high ionic strengths (17% sodium chloride, w v−1) and under agitation. Results: A total of 82 volatile metabolites belonging to distinct chemical classes were identified in the control and oncological groups. Benzene derivatives, terpenoids and phenols were the most common classes for the oncological group, whereas ketones and sulphur compounds were the main classes that were isolated from the urine headspace of healthy subjects. The results demonstrate that compound concentrations were dramatically different between cancer patients and healthy volunteers. The positive rates of 16 patients among the 82 identified were found to be statistically different (P<0.05). A significant increase in the peak area of 2-methyl-3-phenyl-2-propenal, p-cymene, anisole, 4-methyl-phenol and 1,2-dihydro-1,1,6-trimethyl-naphthalene in cancer patients was observed. On average, statistically significant lower abundances of dimethyl disulphide were found in cancer patients. Conclusions: Gas chromatographic peak areas were submitted to multivariate analysis (principal component analysis and supervised linear discriminant analysis) to visualise clusters within cases and to detect the volatile metabolites that are able to differentiate cancer patients from healthy individuals. Very good discrimination within cancer groups and between cancer and control groups was achieved. PMID:22085842

Metal complexes as DNA intercalators.

PubMed

Liu, Hong-Ke; Sadler, Peter J

2011-05-17

DNA has a strong affinity for many heterocyclic aromatic dyes, such as acridine and its derivatives. Lerman in 1961 first proposed intercalation as the source of this affinity, and this mode of DNA binding has since attracted considerable research scrutiny. Organic intercalators can inhibit nucleic acid synthesis in vivo, and they are now common anticancer drugs in clinical therapy. The covalent attachment of organic intercalators to transition metal coordination complexes, yielding metallointercalators, can lead to novel DNA interactions that influence biological activity. Metal complexes with σ-bonded aromatic side arms can act as dual-function complexes: they bind to DNA both by metal coordination and through intercalation of the attached aromatic ligand. These aromatic side arms introduce new modes of DNA binding, involving mutual interactions of functional groups held in close proximity. The biological activity of both cis- and trans-diamine Pt(II) complexes is dramatically enhanced by the addition of σ-bonded intercalators. We have explored a new class of organometallic "piano-stool" Ru(II) and Os(II) arene anticancer complexes of the type [(η(6)-arene)Ru/Os(XY)Cl](+). Here XY is, for example, ethylenediamine (en), and the arene ligand can take many forms, including tetrahydroanthracene, biphenyl, or p-cymene. Arene-nucleobase stacking interactions can have a significant influence on both the kinetics and thermodynamics of DNA binding. In particular, the cytotoxic activity, conformational distortions, recognition by DNA-binding proteins, and repair mechanisms are dependent on the arene. A major difficulty in developing anticancer drugs is cross-resistance, a phenomenon whereby a cell that is resistant to one drug is also resistant to another drug in the same class. These new complexes are non-cross-resistant with cisplatin towards cancer cells: they constitute a new class of anticancer agents, with a mechanism of action that differs from the anticancer drug cisplatin and its analogs. The Ru-arene complexes with dual functions are more potent towards cancer cells than their nonintercalating analogs. In this Account, we focus on recent studies of dual-function organometallic Ru(II)- and Os(II)-arene complexes and the methods used to detect arene-DNA intercalation. We relate these interactions to the mechanism of anticancer activity and to structure-activity relationships. The interactions between these complexes and DNA show close similarities to those of covalent polycyclic aromatic carcinogens, especially to N7-alkylating intercalation compounds. However, Ru-arene complexes exhibit some new features. Classical intercalation and base extrusion next to the metallated base is observed for {(η(6)-biphenyl)Ru(ethylenediamine)}(2+) adducts of a 14-mer duplex, while penetrating arene intercalation occurs for adducts of the nonaromatic bulky intercalator {(η(6)-tetrahydroanthracene)Ru(ethylenediamine)}(2+) with a 6-mer duplex. The introduction of dual-function Ru-arene complexes introduces new mechanisms of antitumor activity, novel mechanisms for attack on DNA, and new concepts for developing structure- activity relationships. We hope this discussion will stimulate thoughtful and focused research on the design of anticancer chemotherapeutic agents using these unique approaches.

Antimosquito property of Petroselinum crispum (Umbellifereae) against the pyrethroid resistant and susceptible strains of Aedes aegypti (Diptera: Culicidae).

PubMed

Intirach, J; Junkum, A; Lumjuan, N; Chaithong, U; Jitpakdi, A; Riyong, D; Wannasan, A; Champakaew, D; Muangmoon, R; Chansang, A; Pitasawat, B

2016-12-01

The increasing and widespread resistance to conventional synthetic insecticides in vector populations has underscored the urgent need to establish alternatives in the mosquito management system. This study was carried out with the aim to investigate the antimosquito property, larvicidal and adulticidal potential, of plant products against both the pyrethroid-susceptible and resistant strains of Aedes aegypti. Seventeen plant products, including essential oils and ethanolic extracts, were obtained by steam distillation and extraction with 95 % ethanol, respectively. Their larvicidal activity was screened, using World Health Organization (WHO) procedures against A. aegypti, Muang Chiang Mai-susceptible (MCM-S) strain. The most effective product was a candidate for investigating larvicidal and adulticidal potential against three laboratory strains of A. aegypti, comprising MCM-S, Pang Mai Dang-resistant (PMD-R), and Upakut-resistant (UPK-R). Potential toxicity of the plant candidate was compared with that of synthetic temephos, permethrin, and deltamethrin. Chemical constituents of the most effective plant product also were analyzed by gas chromatography-mass spectrometry (GC-MS). Results obtained from the preliminary screening revealed the varying larvicidal efficacy of plant-derived products against MCM-S A. aegypti, with mortality ranging from 0 to 100 %. The larvicidal activity of seven effective plant products was found to be dose dependent, with the highest efficacy established from Petroselinum crispum fruit oil, followed by oils of Foeniculum vulgare, Myristica fragrans, Limnophila aromatica, Piper sarmentosum, Curcuma longa, and M. fragrans ethanolic extract (LC 50 values of 43.22, 44.84, 47.42, 47.94, 49.19, 65.51, and 75.45 ppm, respectively). Essential oil of P. crispum was then investigated further and proved to be a promising larvicide and adulticide against all strains of A. aegypti. The pyrethroid-resistant strains of both PMD-R and UPK-R A. aegypti showed significant resistance to temephos, permethrin, and deltamethrin in either the larval or adult stage. Interestingly, high susceptibility to P. crispum oil was observed in the larvae and adults of MCM-S, which are pyrethroid-susceptible A. aegypti, and comparable to those of the pyrethroid-resistant strains, PMD-R and UPK-R. GC-MS analysis of P. crispum oil demonstrated that 19 compounds, accounting for 98.25 % of the whole oil, were identified, with the main constituents being thymol (42.41 %), p-cymene (27.71 %), and γ-terpinene (20.98 %). In conclusion, the profound larvicidal and adulticidal potential of P. crispum oil promises to form a new larvicide and adulticide against either the pyrethroid-susceptible or resistant strain of A. aegypti. Consequently, P. crispum oil and its constituents can be used or incorporated with other chemicals/measures in integrated mosquito management for controlling A. aegypti, particularly in localities with high levels of pyrethroid and organophosphate resistance.

Four-coordinate, 14-electron Ru(II) complexes: unusual trigonal pyramidal geometry enforced by bis(phosphino)silyl ligation.

PubMed

MacInnis, Morgan C; McDonald, Robert; Ferguson, Michael J; Tobisch, Sven; Turculet, Laura

2011-08-31

Unprecedented diamagnetic, four-coordinate, formally 14-electron (Cy-PSiP)RuX (Cy-PSiP = [κ(3)-(2-R(2)PC(6)H(4))(2)SiMe](-); X = amido, alkoxo) complexes that do not require agostic stabilization and that adopt a highly unusual trigonal pyramidal coordination geometry are reported. The tertiary silane [(2-Cy(2)PC(6)H(4))(2)SiMe]H ((Cy-PSiP)H) reacted with 0.5 [(p-cymene)RuCl(2)](2) in the presence of Et(3)N and PCy(3) to afford [(Cy-PSiP)RuCl](2) (1) in 74% yield. Treatment of 1 with KO(t)Bu led to the formation of (Cy-PSiP)RuO(t)Bu (2, 97% yield), which was crystallographically characterized and shown to adopt a trigonal pyramidal coordination geometry in the solid state. Treatment of 1 with NaN(SiMe(3))(2) led to the formation of (Cy-PSiP)RuN(SiMe(3))(2) (3, 70% yield), which was also found to adopt a trigonal pyramidal coordination geometry in the solid state. The related anilido complexes (Cy-PSiP)RuNH(2,6-R(2)C(6)H(3)) (4, R = H; 5, R = Me) were also prepared in >90% yields by treating 1 with LiNH(2,6-R(2)C(6)H(3)) (R = H, Me) reagents. The solid state structure of 5 indicates a monomeric trigonal pyramidal complex that features a C-H agostic interaction. Complexes 2 and 3 were found to react readily with 1 equiv of H(2)O to form the dimeric hydroxo-bridged complex [(Cy-PSiP)RuOH](2) (6, 94% yield), which was crystallographically characterized. Complexes 2 and 3 also reacted with 1 equiv of PhOH to form the new 18-electron η(5)-oxocyclohexadienyl complex (Cy-PSiP)Ru(η(5)-C(6)H(5)O) (7, 84% yield). Both amido and alkoxo (Cy-PSiP)RuX complexes reacted with H(3)B·NHRR' reagents to form bis(σ-B-H) complexes of the type (Cy-PSiP)RuH(η(2):η(2)-H(2)BNRR') (8, R = R' = H; 9, R = R' = Me; 10, R = H, R' = (t)Bu), which illustrates that such four-coordinate (Cy-PSiP)RuX (X = amido, alkoxo) complexes are able to undergo multiple E-H (E = main group element) bond activation steps. Computational methods were used to investigate structurally related PCP, PPP, PNP, and PSiP four-coordinate Ru complexes and confirmed the key role of the strongly σ-donating silyl group of the PSiP ligand set in enforcing the unusual trigonal pyramidal coordination geometry featured in complexes 2-5, thus substantiating a new strategy for the synthesis of low-coordinate Ru species. The mechanism of the activation of ammonia-borane by such low-coordinate (R-PSiP)RuX (X = amido, alkoxo) species was also studied computationally and was determined to proceed most likely in a stepwise fashion via intramolecular deprotonation of ammonia and subsequent borane B-H bond oxidative addition steps.

In situ secondary organic aerosol formation from ambient pine forest air using an oxidation flow reactor

DOE PAGES

Palm, Brett B.; Campuzano-Jost, Pedro; Ortega, Amber M.; ...

2016-03-08

An oxidation flow reactor (OFR) is a vessel inside which the concentration of a chosen oxidant can be increased for the purpose of studying SOA formation and aging by that oxidant. During the BEACHON-RoMBAS (Bio-hydro-atmosphere interactions of Energy, Aerosols, Carbon, H 2O, Organics & Nitrogen–Rocky Mountain Biogenic Aerosol Study) field campaign, ambient pine forest air was oxidized by OH radicals in an OFR to measure the amount of SOA that could be formed from the real mix of ambient SOA precursor gases, and how that amount changed with time as precursors changed. High OH concentrations and short residence times allowedmore » for semicontinuous cycling through a large range of OH exposures ranging from hours to weeks of equivalent (eq.) atmospheric aging. A simple model is derived and used to account for the relative timescales of condensation of low-volatility organic compounds (LVOCs) onto particles; condensational loss to the walls; and further reaction to produce volatile, non-condensing fragmentation products. More SOA production was observed in the OFR at nighttime (average 3 µg m –3 when LVOC fate corrected) compared to daytime (average 0.9 µg m –3 when LVOC fate corrected), with maximum formation observed at 0.4–1.5 eq. days of photochemical aging. SOA formation followed a similar diurnal pattern to monoterpenes, sesquiterpenes, and toluene+ p-cymene concentrations, including a substantial increase just after sunrise at 07:00 local time. Higher photochemical aging (>10 eq. days) led to a decrease in new SOA formation and a loss of preexisting OA due to heterogeneous oxidation followed by fragmentation and volatilization. When comparing two different commonly used methods of OH production in OFRs (OFR185 and OFR254-70), similar amounts of SOA formation were observed. We recommend the OFR185 mode for future forest studies. Concurrent gas-phase measurements of air after OH oxidation illustrate the decay of primary VOCs, production of small oxidized organic compounds, and net production at lower ages followed by net consumption of terpenoid oxidation products as photochemical age increased. New particle formation was observed in the reactor after oxidation, especially during times when precursor gas concentrations and SOA formation were largest. Approximately 4.4 times more SOA was formed in the reactor from OH oxidation than could be explained by the VOCs measured in ambient air. To our knowledge this is the first time that this has been shown when comparing VOC concentrations with SOA formation measured at the same time, rather than comparing measurements made at different times. Several recently developed instruments have quantified ambient semivolatile and intermediate-volatility organic compounds (S/IVOCs) that were not detected by a proton transfer reaction time-of-flight mass spectrometer (PTR-TOF-MS). An SOA yield of 18–58 % from those compounds can explain the observed SOA formation. S/IVOCs were the only pool of gas-phase carbon that was large enough to explain the observed SOA formation. This work suggests that these typically unmeasured gases play a substantial role in ambient SOA formation. Our results allow ruling out condensation sticking coefficients much lower than 1. Lastly, these measurements help clarify the magnitude of potential SOA formation from OH oxidation in forested environments and demonstrate methods for interpretation of ambient OFR measurements.« less

In situ secondary organic aerosol formation from ambient pine forest air using an oxidation flow reactor

NASA Astrophysics Data System (ADS)

Palm, Brett B.; Campuzano-Jost, Pedro; Ortega, Amber M.; Day, Douglas A.; Kaser, Lisa; Jud, Werner; Karl, Thomas; Hansel, Armin; Hunter, James F.; Cross, Eben S.; Kroll, Jesse H.; Peng, Zhe; Brune, William H.; Jimenez, Jose L.

2016-03-01

An oxidation flow reactor (OFR) is a vessel inside which the concentration of a chosen oxidant can be increased for the purpose of studying SOA formation and aging by that oxidant. During the BEACHON-RoMBAS (Bio-hydro-atmosphere interactions of Energy, Aerosols, Carbon, H2O, Organics & Nitrogen-Rocky Mountain Biogenic Aerosol Study) field campaign, ambient pine forest air was oxidized by OH radicals in an OFR to measure the amount of SOA that could be formed from the real mix of ambient SOA precursor gases, and how that amount changed with time as precursors changed. High OH concentrations and short residence times allowed for semicontinuous cycling through a large range of OH exposures ranging from hours to weeks of equivalent (eq.) atmospheric aging. A simple model is derived and used to account for the relative timescales of condensation of low-volatility organic compounds (LVOCs) onto particles; condensational loss to the walls; and further reaction to produce volatile, non-condensing fragmentation products. More SOA production was observed in the OFR at nighttime (average 3 µg m-3 when LVOC fate corrected) compared to daytime (average 0.9 µg m-3 when LVOC fate corrected), with maximum formation observed at 0.4-1.5 eq. days of photochemical aging. SOA formation followed a similar diurnal pattern to monoterpenes, sesquiterpenes, and toluene+p-cymene concentrations, including a substantial increase just after sunrise at 07:00 local time. Higher photochemical aging (> 10 eq. days) led to a decrease in new SOA formation and a loss of preexisting OA due to heterogeneous oxidation followed by fragmentation and volatilization. When comparing two different commonly used methods of OH production in OFRs (OFR185 and OFR254-70), similar amounts of SOA formation were observed. We recommend the OFR185 mode for future forest studies. Concurrent gas-phase measurements of air after OH oxidation illustrate the decay of primary VOCs, production of small oxidized organic compounds, and net production at lower ages followed by net consumption of terpenoid oxidation products as photochemical age increased. New particle formation was observed in the reactor after oxidation, especially during times when precursor gas concentrations and SOA formation were largest. Approximately 4.4 times more SOA was formed in the reactor from OH oxidation than could be explained by the VOCs measured in ambient air. To our knowledge this is the first time that this has been shown when comparing VOC concentrations with SOA formation measured at the same time, rather than comparing measurements made at different times. Several recently developed instruments have quantified ambient semivolatile and intermediate-volatility organic compounds (S/IVOCs) that were not detected by a proton transfer reaction time-of-flight mass spectrometer (PTR-TOF-MS). An SOA yield of 18-58 % from those compounds can explain the observed SOA formation. S/IVOCs were the only pool of gas-phase carbon that was large enough to explain the observed SOA formation. This work suggests that these typically unmeasured gases play a substantial role in ambient SOA formation. Our results allow ruling out condensation sticking coefficients much lower than 1. These measurements help clarify the magnitude of potential SOA formation from OH oxidation in forested environments and demonstrate methods for interpretation of ambient OFR measurements.