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Sample records for acids phenolic compounds

  1. Phenolic compounds and fatty acid composition of organic and conventional grown pecan kernels

    Technology Transfer Automated Retrieval System (TEKTRAN)

    In this study, differences in contents of phenolic compounds and fatty acids in pecan kernels of organically versus conventionally grown pecan cultivars (‘Desirable’, ‘Cheyenne’, and ‘Wichita’) were evaluated. Although we were able to identify nine phenolic compounds (gallic acid, catechol, catechin...

  2. Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat

    PubMed Central

    Ma, Dongyun; Li, Yaoguang; Zhang, Jian; Wang, Chenyang; Qin, Haixia; Ding, Huina; Xie, Yingxin; Guo, Tiancai

    2016-01-01

    Polyphenols in whole grain wheat have potential health benefits, but little is known about the expression patterns of phenolic acid biosynthesis genes and the accumulation of phenolic acid compounds in different-colored wheat grains. We found that purple wheat varieties had the highest total phenolic content (TPC) and antioxidant activity. Among phenolic acid compounds, bound ferulic acid, vanillic, and caffeic acid levels were significantly higher in purple wheat than in white and red wheat, while total soluble phenolic acid, soluble ferulic acid, and vanillic acid levels were significantly higher in purple and red wheat than in white wheat. Ferulic acid and syringic acid levels peaked at 14 days after anthesis (DAA), whereas p-coumaric acid and caffeic acid levels peaked at 7 DAA, and vanillic acid levels gradually increased during grain filling and peaked near ripeness (35 DAA). Nine phenolic acid biosynthesis pathway genes (TaPAL1, TaPAL2, TaC3H1, TaC3H2, TaC4H, Ta4CL1, Ta4CL2, TaCOMT1, and TaCOMT2) exhibited three distinct expression patterns during grain filling, which may be related to the different phenolic acids levels. White wheat had higher phenolic acid contents and relatively high gene expression at the early stage, while purple wheat had the highest phenolic acid contents and gene expression levels at later stages. These results suggest that the expression of phenolic acid biosynthesis genes may be closely related to phenolic acids accumulation. PMID:27148345

  3. Peracetic Acid Depolymerization of Biorefinery Lignin for Production of Selective Monomeric Phenolic Compounds.

    PubMed

    Ma, Ruoshui; Guo, Mond; Lin, Kuan-Ting; Hebert, Vincent R; Zhang, Jinwen; Wolcott, Michael P; Quintero, Melissa; Ramasamy, Karthikeyan K; Chen, Xiaowen; Zhang, Xiao

    2016-07-25

    Lignin is the largest source of renewable material with an aromatic skeleton. However, due to the recalcitrant and heterogeneous nature of the lignin polymer, it has been a challenge to effectively depolymerize lignin and produce high-value chemicals with high selectivity. In this study, a highly efficient lignin-to-monomeric phenolic compounds (MPC) conversion method based on peracetic acid (PAA) treatment was reported. PAA treatment of two biorefinery lignin samples, diluted acid pretreated corn stover lignin (DACSL) and steam exploded spruce lignin (SESPL), led to complete solubilization and production of selective hydroxylated monomeric phenolic compounds (MPC-H) and monomeric phenolic acid compounds (MPC-A) including 4-hydroxy-2-methoxyphenol, p-hydroxybenzoic acid, vanillic acid, syringic acid, and 3,4-dihydroxybenzoic acid. The maximized MPC yields obtained were 18 and 22 % based on the initial weight of the lignin in SESPL and DACSL, respectively. However, we found that the addition of niobium pentoxide catalyst to PAA treatment of lignin can significantly improve the MPC yields up to 47 %. The key reaction steps and main mechanisms involved in this new lignin-to-MPC valorization pathway were investigated and elucidated.

  4. Peracetic Acid Depolymerization of Biorefinery Lignin for Production of Selective Monomeric Phenolic Compounds.

    PubMed

    Ma, Ruoshui; Guo, Mond; Lin, Kuan-Ting; Hebert, Vincent R; Zhang, Jinwen; Wolcott, Michael P; Quintero, Melissa; Ramasamy, Karthikeyan K; Chen, Xiaowen; Zhang, Xiao

    2016-07-25

    Lignin is the largest source of renewable material with an aromatic skeleton. However, due to the recalcitrant and heterogeneous nature of the lignin polymer, it has been a challenge to effectively depolymerize lignin and produce high-value chemicals with high selectivity. In this study, a highly efficient lignin-to-monomeric phenolic compounds (MPC) conversion method based on peracetic acid (PAA) treatment was reported. PAA treatment of two biorefinery lignin samples, diluted acid pretreated corn stover lignin (DACSL) and steam exploded spruce lignin (SESPL), led to complete solubilization and production of selective hydroxylated monomeric phenolic compounds (MPC-H) and monomeric phenolic acid compounds (MPC-A) including 4-hydroxy-2-methoxyphenol, p-hydroxybenzoic acid, vanillic acid, syringic acid, and 3,4-dihydroxybenzoic acid. The maximized MPC yields obtained were 18 and 22 % based on the initial weight of the lignin in SESPL and DACSL, respectively. However, we found that the addition of niobium pentoxide catalyst to PAA treatment of lignin can significantly improve the MPC yields up to 47 %. The key reaction steps and main mechanisms involved in this new lignin-to-MPC valorization pathway were investigated and elucidated. PMID:27373451

  5. Voltammetric response of ferroceneboronic acid to diol and phenolic compounds as possible pollutants.

    PubMed

    Takahashi, Shigehiro; Abiko, Naoyuki; Haraguchi, Nobuhiro; Fujita, Hiroyuki; Seki, Eriko; Ono, Tetsuya; Yoshida, Kentaro; Anzai, Jun-ichi

    2011-01-01

    A voltammetric determination of possible organic pollutants such as diol and phenolic compounds in water was studied using ferroceneboronic acid (FBA) as a redox-active marker. A cyclic voltammogram of FBA exhibited a pair of oxidation and reduction peaks at 230 and 170 mV at pH 7.0, respectively, while another pair of redox peaks was observed in the presence of diol or phenolic compounds tested. The results were rationalized based on the formation of boronate esters of FBA with the added compounds. The changes in the redox peak currents were dependent on the concentration of the additives, suggesting a usefulness of FBA in the electrochemical determination of these compounds in water. PMID:22066227

  6. Lipid encapsulated phenolic compounds by fluidization

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phenolic compounds exhibit antioxidant and antimicrobial activities with applications as functional food and feed additives. Ferulic acid, a phenolic compound present in grain crops and lignocellulose biomass, was encapsulated with saturated triglycerides using a laboratory fluidizer. Stability of t...

  7. Antagonism between lipid-derived reactive carbonyls and phenolic compounds in the Strecker degradation of amino acids.

    PubMed

    Delgado, Rosa M; Hidalgo, Francisco J; Zamora, Rosario

    2016-03-01

    The Strecker-type degradation of phenylalanine in the presence of 2-pentanal and phenolic compounds was studied to investigate possible interactions that either promote or inhibit the formation of Strecker aldehydes in food products. Phenylacetaldehyde formation was promoted by 2-pentenal and also by o- and p-diphenols, but not by m-diphenols. This is consequence of the ability of phenolic compounds to be converted into reactive carbonyls and produce the Strecker degradation of the amino acid. When 2-pentenal and phenolic compounds were simultaneously present, an antagonism among them was observed. This antagonism is suggested to be a consequence of the ability of phenolic compounds to either react with both 2-pentenal and phenylacetaldehyde, or compete with other carbonyl compounds for the amino acids, a function that is determined by their structure. All these results suggest that carbonyl-phenol reactions may be used to modulate flavor formation produced in food products by lipid-derived reactive carbonyls.

  8. Infusion and decoction of wild German chamomile: bioactivity and characterization of organic acids and phenolic compounds.

    PubMed

    Guimarães, Rafaela; Barros, Lillian; Dueñas, Montserrat; Calhelha, Ricardo C; Carvalho, Ana Maria; Santos-Buelga, Celestino; Queiroz, Maria João R P; Ferreira, Isabel C F R

    2013-01-15

    Natural products represent a rich source of biologically active compounds and are an example of molecular diversity, with recognised potential in drug discovery. Herein, the methanol extract of Matricaria recutita L. (German chamomile) and its decoction and infusion (the most consumed preparations of this herb) were submitted to an analysis of phytochemicals and bioactivity evaluation. The antioxidant activity was determined by free radicals scavenging activity, reducing power and inhibition of lipid peroxidation; the antitumour potential was tested in human tumour cell lines (breast, lung, colon, cervical and hepatocellular carcinomas), and the hepatotoxicity was evaluated using a porcine liver primary cell culture (non-tumour cells). All the samples revealed antioxidant properties. The decoction exhibited no antitumour activity (GI(50)>400 μg/mL) which could indicate that this bioactivity might be related to compounds (including phenolic compounds) that were not extracted or that were affected by the decoction procedure. Both plant methanol extract and infusion showed inhibitory activity to the growth of HCT-15 (GI(50) 250.24 and 298.23 μg/mL, respectively) and HeLa (GI(50) 259.36 and 277.67 μg/mL, respectively) cell lines, without hepatotoxicity (GI(50)>400 μg/mL). Infusion and decoction gave higher contents of organic acids (24.42 and 23.35 g/100g dw). Otherwise, the plant methanol extract contained the highest amounts of both phenolic acids (3.99 g/100g dw) and flavonoids (2.59 g/100g dw). The major compound found in all the preparations was luteolin O-acylhexoside. Overall, German chamomile contains important phytochemicals with bioactive properties (mainly antitumour potential selective to colon and cervical carcinoma cell lines) to be explored in the pharmaceutical, food and cosmetics industries. PMID:23122148

  9. Influence of technological processes on phenolic compounds, organic acids, furanic derivatives, and antioxidant activity of whole-lemon powder.

    PubMed

    García-Salas, Patricia; Gómez-Caravaca, Ana María; Arráez-Román, David; Segura-Carretero, Antonio; Guerra-Hernández, Eduardo; García-Villanova, Belén; Fernández-Gutiérrez, Alberto

    2013-11-15

    The healthy properties of citrus fruits have been attributed to ascorbic acid and phenolic compounds, mainly to flavonoids. Flavonoids are important phytonutrients because they have a wide range of biological effects that provide health-related properties. In this context, this study seeks to characterise the phenolic compounds in lemon and their stability in different drying processes (freeze-drying and vacuum-drying) and storage conditions (-18 and 50°C for 1 and 3months). A powerful high-performance liquid chromatography coupled to DAD and electrospray-ionization time-of-flight mass spectrometry (HPLC-ESI-TOF-MS) method has been applied for the separation, identification, and quantification of 19 phenolic compounds and 4 organic acids. To our knowledge, two hydroxycinnamic acids have been identified for the first time in lemon. Folin-Ciocalteu was applied to determine total phenolic compounds and TEAC, FRAP, and ORAC were applied to determine the antioxidant capacity of lemon. Total phenolic content significantly differed in the samples analysed, vacuum-dried lemon showing the highest phenolic content, followed by freeze-dried lemon and, finally, vacuum-dried lemon stored at 50°C for 1 and 3months. The content in furanic compounds was determined to evaluate the heat damage in lemon and it was showed an increase with the thermal treatment because of the triggering of Maillard reaction. As exception of ORAC, antioxidant-capacity assays were not correlated to phenolic content by HPLC due to the formation of antioxidant compounds during Maillard reaction. PMID:23790861

  10. Influence of technological processes on phenolic compounds, organic acids, furanic derivatives, and antioxidant activity of whole-lemon powder.

    PubMed

    García-Salas, Patricia; Gómez-Caravaca, Ana María; Arráez-Román, David; Segura-Carretero, Antonio; Guerra-Hernández, Eduardo; García-Villanova, Belén; Fernández-Gutiérrez, Alberto

    2013-11-15

    The healthy properties of citrus fruits have been attributed to ascorbic acid and phenolic compounds, mainly to flavonoids. Flavonoids are important phytonutrients because they have a wide range of biological effects that provide health-related properties. In this context, this study seeks to characterise the phenolic compounds in lemon and their stability in different drying processes (freeze-drying and vacuum-drying) and storage conditions (-18 and 50°C for 1 and 3months). A powerful high-performance liquid chromatography coupled to DAD and electrospray-ionization time-of-flight mass spectrometry (HPLC-ESI-TOF-MS) method has been applied for the separation, identification, and quantification of 19 phenolic compounds and 4 organic acids. To our knowledge, two hydroxycinnamic acids have been identified for the first time in lemon. Folin-Ciocalteu was applied to determine total phenolic compounds and TEAC, FRAP, and ORAC were applied to determine the antioxidant capacity of lemon. Total phenolic content significantly differed in the samples analysed, vacuum-dried lemon showing the highest phenolic content, followed by freeze-dried lemon and, finally, vacuum-dried lemon stored at 50°C for 1 and 3months. The content in furanic compounds was determined to evaluate the heat damage in lemon and it was showed an increase with the thermal treatment because of the triggering of Maillard reaction. As exception of ORAC, antioxidant-capacity assays were not correlated to phenolic content by HPLC due to the formation of antioxidant compounds during Maillard reaction.

  11. Antagonism between lipid-derived reactive carbonyls and phenolic compounds in the Strecker degradation of amino acids.

    PubMed

    Delgado, Rosa M; Hidalgo, Francisco J; Zamora, Rosario

    2016-03-01

    The Strecker-type degradation of phenylalanine in the presence of 2-pentanal and phenolic compounds was studied to investigate possible interactions that either promote or inhibit the formation of Strecker aldehydes in food products. Phenylacetaldehyde formation was promoted by 2-pentenal and also by o- and p-diphenols, but not by m-diphenols. This is consequence of the ability of phenolic compounds to be converted into reactive carbonyls and produce the Strecker degradation of the amino acid. When 2-pentenal and phenolic compounds were simultaneously present, an antagonism among them was observed. This antagonism is suggested to be a consequence of the ability of phenolic compounds to either react with both 2-pentenal and phenylacetaldehyde, or compete with other carbonyl compounds for the amino acids, a function that is determined by their structure. All these results suggest that carbonyl-phenol reactions may be used to modulate flavor formation produced in food products by lipid-derived reactive carbonyls. PMID:26471665

  12. Phenolic compounds, organic acids and antioxidant activity of grape juices produced in industrial scale by different processes of maceration.

    PubMed

    Lima, Marcos dos Santos; da Conceição Prudêncio Dutra, Maria; Toaldo, Isabela Maia; Corrêa, Luiz Claudio; Pereira, Giuliano Elias; de Oliveira, Débora; Bordignon-Luiz, Marilde Terezinha; Ninow, Jorge Luiz

    2015-12-01

    The effect of maceration process on the profile of phenolic compounds, organic acids composition and antioxidant activity of grape juices from new varieties of Vitis labrusca L. obtained in industrial scale was investigated. The extraction process presented a high yield without pressing the grapes. The use of a commercial pectinase resulted in an increase on extraction yield and procyanidins B1 and B2 concentrations and a decrease on turbidity and concentration of catechins. The combination of 60 °C and 3.0 mL 100 kg(-1) of enzyme resulted in the highest extraction of phenolic compounds, reducing the content of acetic acid. The juices presented high antioxidant activity, related to the great concentration of malvidin, cyanidin, catechin and caffeic, cinnamic and gallic acids. Among the bioactive compounds, the juices presented high concentration of procyanidin B1, caffeic acid and trans-resveratrol, with higher levels compared to those reported in the literature.

  13. Functional milk beverage fortified with phenolic compounds extracted from olive vegetation water, and fermented with functional lactic acid bacteria.

    PubMed

    Servili, M; Rizzello, C G; Taticchi, A; Esposto, S; Urbani, S; Mazzacane, F; Di Maio, I; Selvaggini, R; Gobbetti, M; Di Cagno, R

    2011-05-14

    Functional milk beverages (FMB100 and FMB200) fortified with phenolic compounds (100 and 200mg/l) extracted from olive vegetable water, and fermented with γ-amino butyric acid (GABA)-producing (Lactobacillus plantarum C48) and autochthonous human gastro-intestinal (Lactobacillus paracasei 15N) lactic acid bacteria were manufactured. A milk beverage (MB), without addition of phenolic compounds, was used as the control. Except for a longer latency phase of FMB200, the three beverages showed an almost similar kinetic of acidification, consumption of lactose and synthesis of lactic acid. Apart from the beverage, Lb. plantarum C48 showed a decrease of ca. Log 2.52-2.24 cfu/ml during storage. The cell density of functional Lb. paracasei 15N remained always above the value of Log 8.0 cfu/ml. During fermentation, the total concentration of free amino acids markedly increased without significant (P > 0.05) differences between beverages. The concentration of GABA increased during fermentation and further storage (63.0 ± 0.6-67.0 ± 2.1mg/l) without significant (P > 0.05) differences between beverages. After fermentation, FMB100 and FMB200 showed the same phenolic composition of the phenol extract from olive vegetable water but a different ratio between 3,4-DHPEA and 3,4-DHPEA-EDA. During storage, the concentrations of 3,4-DHPEA-EDA, p-HPEA and verbascoside of both FMB100 and FMB200 decreased. Only the concentration of 3,4-DHPEA increased. As shown by SPME-GC-MS analysis, diactetyl, acetoin and, especially, acetaldehyde were the main volatile compounds found. The concentration of phenolic compounds does not interfere with the volatile composition. Sensory analyses based on triangle and paired comparison tests showed that phenolic compounds at the concentrations of 100 or 200mg/l were suitable for addition to functional milk beverages.

  14. Decolorization of molasses melanoidins and palm oil mill effluent phenolic compounds by fermentative lactic acid bacteria.

    PubMed

    Limkhuansuwan, Vassanasak; Chaiprasert, Pawinee

    2010-01-01

    Lactobacillus plantarum SF5.6 is one of the lactic acid bacteria (LAB) that has the highest ability of molasses melanoidin (MM) decolorization among the 2114 strains of LAB. The strains were isolated from spoilage, pickle fruit and vegetable, soil and sludge from the wastewater treatment system by using technical step of enrichment, primary screening and secondary screening. This LAB strain SF5.6 was identified by 16S rDNA analysis and carbohydrate fermentation (API 50 CH). The top five LAB strains having high MM decolorization (> 55%), namely TBSF5.8-1, TBSF2.1-1, TBSF2.1, FF4A and SF5.6 were selected to determine the optimal condition. It was found that the temperature at 30 degrees C under facultative conditions in GPY-MM medium (0.5% glucose, 0.1% peptone, 0.1% yeast extract, 0.1% sodium acetate, 0.05% MgSO4 and 0.005% MnCl2 in MM solution at pH 6) giving a high microbial growth and MM decolorization for all five strains. It was noticed that the decolorization of MM by LAB strains might be cell growth associated. L. plantarum SF5.6 grew rapidly within one day while the other strains took 2-3 days. This L. plantarum SF5.6 could rapidly decolorize MM to 60.91% without any lag phase, and it also had the ability to remove 34.00% phenolic compounds and 15.88% color from treated palm oil mill effluent.

  15. Antioxidant activity of phenolic compounds added to a functional emulsion containing omega-3 fatty acids and plant sterol esters.

    PubMed

    Espinosa, Raquel Rainho; Inchingolo, Raffaella; Alencar, Severino Matias; Rodriguez-Estrada, Maria Teresa; Castro, Inar Alves

    2015-09-01

    The effect of eleven compounds extracted from red propolis on the oxidative stability of a functional emulsion was evaluated. Emulsions prepared with Echium oil as omega 3 (ω-3 FA) source, containing 1.63 g/100mL of α-linolenic acid (ALA), 0.73 g/100 mL of stearidonic acid (SDA) and 0.65 g/100mL of plant sterol esters (PSE) were prepared without or with phenolic compounds (vanillic acid, caffeic acid, trans-cinnamic acid, 2,4-dihydroxycinnamic acid, p-coumaric acid, quercetin, trans-ferulic acid, trans,trans-farnesol, rutin, gallic acid or sinapic acid). tert-Butylhydroquinone and a mixture containing ascorbic acid and FeSO4 were applied as negative and positive controls of the oxidation. Hydroperoxide, thiobarbituric acid reactive substances (TBARS), malondialdehyde and phytosterol oxidation products (POPs) were evaluated as oxidative markers. Based on hydroperoxide and TBARS analysis, sinapic acid and rutin (200 ppm) showed the same antioxidant activity than TBHQ, representing a potential alternative as natural antioxidant to be applied in a functional emulsion containing ω-3 FA and PSE.

  16. Phenolic compounds in Ross Sea water

    NASA Astrophysics Data System (ADS)

    Zangrando, Roberta; Barbaro, Elena; Gambaro, Andrea; Barbante, Carlo; Corami, Fabiana; Kehrwald, Natalie; Capodaglio, Gabriele

    2016-04-01

    Phenolic compounds are semi-volatile organic compounds produced during biomass burning and lignin degradation in water. In atmospheric and paleoclimatic ice cores studies, these compounds are used as biomarkers of wood combustion and supply information on the type of combusted biomass. Phenolic compounds are therefore indicators of paleoclimatic interest. Recent studies of Antarctic aerosols highlighted that phenolic compounds in Antarctica are not exclusively attributable to biomass burning but also derive from marine sources. In order to study the marine contribution to aerosols we developed an analytical method to determine the concentration of vanillic acid, vanillin, p-coumaric acid, syringic acid, isovanillic acid, homovanillic acid, syringaldehyde, acetosyringone and acetovanillone present in dissolved and particle phases in Sea Ross waters using HPLC-MS/MS. The analytical method was validated and used to quantify phenolic compounds in 28 sea water samples collected during a 2012 Ross Sea R/V cruise. The observed compounds were vanillic acid, vanillin, acetovanillone and p-coumaric acid with concentrations in the ng/L range. Higher concentrations of analytes were present in the dissolved phase than in the particle phase. Sample concentrations were greatest in the coastal, surficial and less saline Ross Sea waters near Victoria Land.

  17. Iron absorption and phenolic compounds: importance of different phenolic structures.

    PubMed

    Brune, M; Rossander, L; Hallberg, L

    1989-08-01

    The phenolic compounds (phenolic monomers, polyphenols, tannins) are considered to interfere with iron absorption by complex formation with iron in the gastro-intestinal lumen, making the iron less available for absorption. Very little is known about the extent to which different types of phenolic compounds of different size and chemical structure inhibit iron absorption. The relationship between iron absorption and the amount and type of phenolic compounds was studied by the extrinsic tag method. The aims of the studies were as follows: (i) To study the effect of small phenolic compounds with different hydroxylation patterns (gallic acid, catechin, chlorogenic acid) on iron absorption, (ii) To study the effect of different amounts of a hydrolysable tannin containing ten gallic acid residues (tannic acid) on iron absorption. (iii) To study the degree of inhibition of iron absorption by some foods and beverages (oregano, spinach, coffee and tea) in relation to their respective content of iron-binding phenolic groups, measured by a newly developed method. The inhibition of iron absorption by tannic acid was strongly dose-related. The smallest amount (5 mg) inhibited absorption by 20 per cent, 25 mg by 67 per cent and 100 mg by 88 per cent. Gallic acid inhibited iron absorption to the same extent as tannic acid, per mol galloyl groups, whereas no inhibition was observed when catechin was added to the test meal. Chlorogenic acid inhibited iron absorption to a lesser extent. Oregano and tea inhibited iron absorption in proportion to their respective content of galloyl groups, whereas the inhibitory effect of spinach was less marked. The inhibiting effect of coffee was explained mainly by its content of galloyl groups, but also by some other factor, probably chlorogenic acid. It is concluded that the content of iron-binding galloyl groups might be a major determinant of the inhibitory effect of phenolic compounds on iron absorption from the diet, whereas the phenolic

  18. Fluctuations of different endogenous phenolic compounds and cinnamic acid in the first days of the rooting process of cherry rootstock 'GiSelA 5' leafy cuttings.

    PubMed

    Trobec, Mateja; Stampar, Franci; Veberic, Robert; Osterc, Gregor

    2005-05-01

    The relationship between the phenol composition of rooting zones and rootability was studied in the first days after the establishment of cuttings. The trial included two different types of cuttings (basal and terminal). Additionally, the influence of exogenously applied auxin (IBA) was observed. The best rooting results (55.6%) were achieved with terminal IBA treated cuttings, while only 1.9% of basal cuttings formed roots. The auxin treatment increased the root formation in terminal, but not in basal cuttings. Low rooting rate of basal cuttings was probably due to higher lignification rate of the basal tissue which can represent a mechanical barrier for root emergence. When measuring phenolic compounds and cinnamic acid, terminal cuttings contained higher (rutin, vanillic acid, (-)-epicatechin, caffeic acid and sinapinic acid) or equal concentrations of detected phenols as basal cuttings, while applied auxin did not influence the level of any of discussed phenolics, neither of cinnamic acid. It is to assume that cuttings for starting of root induction phase should contain certain levels of several phenolic compounds, but higher influence on rooting success is to be ascribed to the impact of the auxin level. During the time of the experiment concentrations of monophenols sinapinic acid and vanillic acid rapidly decreased. This decrease was more pronounced in terminal cuttings, which might have a better mechanism of lowering those two compounds to which a negative influence on rooting is ascribed. Fluctuations and differences between treatments of other phenolics were not significant enough to influence the rooting process. PMID:15940876

  19. Fluctuations of different endogenous phenolic compounds and cinnamic acid in the first days of the rooting process of cherry rootstock 'GiSelA 5' leafy cuttings.

    PubMed

    Trobec, Mateja; Stampar, Franci; Veberic, Robert; Osterc, Gregor

    2005-05-01

    The relationship between the phenol composition of rooting zones and rootability was studied in the first days after the establishment of cuttings. The trial included two different types of cuttings (basal and terminal). Additionally, the influence of exogenously applied auxin (IBA) was observed. The best rooting results (55.6%) were achieved with terminal IBA treated cuttings, while only 1.9% of basal cuttings formed roots. The auxin treatment increased the root formation in terminal, but not in basal cuttings. Low rooting rate of basal cuttings was probably due to higher lignification rate of the basal tissue which can represent a mechanical barrier for root emergence. When measuring phenolic compounds and cinnamic acid, terminal cuttings contained higher (rutin, vanillic acid, (-)-epicatechin, caffeic acid and sinapinic acid) or equal concentrations of detected phenols as basal cuttings, while applied auxin did not influence the level of any of discussed phenolics, neither of cinnamic acid. It is to assume that cuttings for starting of root induction phase should contain certain levels of several phenolic compounds, but higher influence on rooting success is to be ascribed to the impact of the auxin level. During the time of the experiment concentrations of monophenols sinapinic acid and vanillic acid rapidly decreased. This decrease was more pronounced in terminal cuttings, which might have a better mechanism of lowering those two compounds to which a negative influence on rooting is ascribed. Fluctuations and differences between treatments of other phenolics were not significant enough to influence the rooting process.

  20. Effect of high hydrostatic pressure on phenolic compounds, ascorbic acid and antioxidant activity in cashew apple juice

    NASA Astrophysics Data System (ADS)

    Queiroz, C.; Moreira, C. F. F.; Lavinas, F. C.; Lopes, M. L. M.; Fialho, E.; Valente-Mesquita, V. L.

    2010-12-01

    The cashew apple is native to Brazil, but there is insufficient information regarding the nutritional properties of this fruit. The objective of this study was to evaluate the impact of high pressure processing (HPP) at room temperature (25 °C) on phenolic compound and ascorbic acid contents and antioxidant capacity of cashew apple juice. This study showed that HPP at 250 or 400 MPa for 3, 5 and 7 min did not change pH, acidity, total soluble solids, ascorbic acid or hydrolysable polyphenol contents. However, juice pressurized for 3 and 5 min showed higher soluble polyphenol contents. Antioxidant capacity, measured by the ferric-reducing antioxidant power method, was not altered by HPP, but when treated at 250 MPa for 3 min, it resulted in an increased value when 2,2-diphenyl-1-picrylhydrazyl was used. These data demonstrate that HPP can be used in the food industry for the generation of products with higher nutritional quality.

  1. Sacha inchi (Plukenetia volubilis): a seed source of polyunsaturated fatty acids, tocopherols, phytosterols, phenolic compounds and antioxidant capacity.

    PubMed

    Chirinos, Rosana; Zuloeta, Gledy; Pedreschi, Romina; Mignolet, Eric; Larondelle, Yvan; Campos, David

    2013-12-01

    Fatty acids (FA), phytosterols, tocopherols, phenolic compounds, total carotenoids and hydrophilic and lipophilic ORAC antioxidant capacities were evaluated in 16 cultivars of Sacha inchi (SI) seeds with the aim to valorise them and offer more information on the functional properties of SI seeds. A high α linolenic (α-Ln) fatty acid content was found in all cultivars (ω3, 12.8-16.0 g/100 g seed), followed by linoleic (L) fatty acid (ω6, 12.4-14.1g/100g seed). The ratio ω6/ω3 was within the 0.83-1.09 range. γ- and δ-tocopherols were the most important tocopherols, whereas the most representative phytosterols were β-sitosterol and stigmasterol. Contents of total phenolics, total carotenoids and hydrophilic and lipophilic antioxidant capacities ranged from 64.6 to 80 mg of gallic acid equivalent/100g seed; from 0.07 to 0.09 mg of β-carotene equivalent/100g of seed; from 4.3 to 7.3 and, from 1.0 to 2.8 μmol of Trolox equivalent/g of seed, respectively, among the evaluated SI cultivars. Results showed significant differences (p<0.05) among the evaluated SI cultivars in the contents of ω3, ω6, antioxidant capacities and other evaluated phytochemicals. SI seeds should be considered as an important dietary source of health promoting phytochemicals. PMID:23870885

  2. Sacha inchi (Plukenetia volubilis): a seed source of polyunsaturated fatty acids, tocopherols, phytosterols, phenolic compounds and antioxidant capacity.

    PubMed

    Chirinos, Rosana; Zuloeta, Gledy; Pedreschi, Romina; Mignolet, Eric; Larondelle, Yvan; Campos, David

    2013-12-01

    Fatty acids (FA), phytosterols, tocopherols, phenolic compounds, total carotenoids and hydrophilic and lipophilic ORAC antioxidant capacities were evaluated in 16 cultivars of Sacha inchi (SI) seeds with the aim to valorise them and offer more information on the functional properties of SI seeds. A high α linolenic (α-Ln) fatty acid content was found in all cultivars (ω3, 12.8-16.0 g/100 g seed), followed by linoleic (L) fatty acid (ω6, 12.4-14.1g/100g seed). The ratio ω6/ω3 was within the 0.83-1.09 range. γ- and δ-tocopherols were the most important tocopherols, whereas the most representative phytosterols were β-sitosterol and stigmasterol. Contents of total phenolics, total carotenoids and hydrophilic and lipophilic antioxidant capacities ranged from 64.6 to 80 mg of gallic acid equivalent/100g seed; from 0.07 to 0.09 mg of β-carotene equivalent/100g of seed; from 4.3 to 7.3 and, from 1.0 to 2.8 μmol of Trolox equivalent/g of seed, respectively, among the evaluated SI cultivars. Results showed significant differences (p<0.05) among the evaluated SI cultivars in the contents of ω3, ω6, antioxidant capacities and other evaluated phytochemicals. SI seeds should be considered as an important dietary source of health promoting phytochemicals.

  3. Influence of the acetification process on phenolic compounds.

    PubMed

    Andlauer, W; Stumpf, C; Fürst, P

    2000-08-01

    Little is known about the change of phenolic compounds and total phenolic content by the acetification process. The aim of this study was to assess the contents of selected phenolic compounds of cider and red and white wines in comparison to phenolic profiles in corresponding vinegars by using a new HPLC method for the simultaneous separation and quantification of polar phenolic acids and less polar flavonoids. Identifications were made by retention times and by means of mass spectra. Additionally, total phenolic contents of wines and vinegars were determined photometrically. The decrease in total phenol content by the acetification process was highest for cider vinegars (40%) and lower for red and white wine vinegars (13 and 8%, respectively). A decrease in the contents of individual phenolic compounds of vinegars from white white and ciders was not observed. In contrast, the contents of individual phenolic compounds in red wine vinegar decreased approximately 50%. PMID:10956145

  4. The effect of the phenol compound ellagic acid on Ca(2+) homeostasis and cytotoxicity in liver cells.

    PubMed

    Liang, Wei-Zhe; Chou, Chiang-Ting; Cheng, Jin-Shiung; Wang, Jue-Long; Chang, Hong-Tai; Chen, I-Shu; Lu, Ti; Yeh, Jeng-Hsien; Kuo, Daih-Huang; Shieh, Pochuen; Chen, Fu-An; Kuo, Chun-Chi; Jan, Chung-Ren

    2016-06-01

    Ellagic acid, a natural phenol compound found in numerous fruits and vegetables, causes various physiological effects in different cell models. However, the effect of this compound on Ca(2+) homeostasis in liver cells is unknown. This study examined the effect of ellagic acid on intracellular Ca(2+) concentration ([Ca(2+)]i) and established the relationship between Ca(2+) signaling and cytotoxicity in liver cells. The data show that ellagic acid induced concentration-dependent [Ca(2+)]i rises in HepG2 human hepatoma cells, but not in HA22T, HA59T human hepatoma cells or AML12 mouse hepatocytes. In HepG2 cells, this Ca(2+) signal response was reduced by removing extracellular Ca(2+) and was inhibited by store-operated Ca(2+) channel blockers (2-APB, econazole or SKF96365) and the protein kinase C (PKC) inhibitor GF109203X. In Ca(2+)-free medium, pretreatment with the endoplasmic reticulum Ca(2+) pump inhibitor thapsigargin abolished ellagic acid-induced [Ca(2+)]i rises. Conversely, incubation with ellagic acid abolished thapsigargin-induced [Ca(2+)]i rises. Inhibition of phospholipase C (PLC) with U73122 also abolished ellagic acid-induced [Ca(2+)]i rises. Ellagic acid (25-100μM) concentration-dependently caused cytotoxicity in HepG2, HA22T or HA59T cells, but not in AML12 cells. Furthermore, this cytotoxic effect was partially prevented by prechelating cytosolic Ca(2+) with BAPTA-AM only in HepG2 cells. Together, in HepG2 cells, ellagic acid induced [Ca(2+)]i rises by inducing PLC-dependent Ca(2+) release from the endoplasmic reticulum and Ca(2+) entry via PKC-sensitive store-operated Ca(2+) channels. Moreover, ellagic acid induced Ca(2+)-associated cytotoxicity. PMID:27038520

  5. Identification and characterization of phenolic compounds in castor seed.

    PubMed

    Chakravartula, Srinivas V S; Guttarla, Nagaraj

    2007-10-01

    Phenolic compounds, polyphenols, and flavonoids occur ubiquitously in plant kingdom, because they are important in plants for normal growth development and defense against infection and injury. Currently, there are no reports available on the phenolic compounds obtained from the residues of the oil-extracting process from defatted castor seed powder. Our studies, for the first time, in methanol-ether extract showed five low-molecular weight phenolic compounds namely p-coumaric acid, ferulic acid, o-coumaric acids, syringic, and cinnamic acids, which were in the soluble ether fractions. All these compounds showed strong absorbance at 240 nm. PMID:17852742

  6. Cinnamic acid, coumarin and vanillin: Alternative phenolic compounds for efficient Agrobacterium-mediated transformation of the unicellular green alga, Nannochloropsis sp.

    PubMed

    Cha, Thye-San; Chen, Chin-Fong; Yee, Willy; Aziz, Ahmad; Loh, Saw-Hong

    2011-03-01

    The use of acetosyringone in Agrobacterium-mediated gene transfer into plant hosts has been favored for the past few decades. The influence of other phenolic compounds and their effectiveness in Agrobacterium-mediated plant transformation systems has been neglected. In this study, the efficacy of four phenolic compounds on Agrobacterium-mediated transformation of the unicellular green alga Nannochloropsis sp. (Strain UMT-M3) was assessed by using β-glucuronidase (GUS) assay. We found that cinnamic acid, vanillin and coumarin produced higher percentages of GUS positive cells as compared to acetosyringone. These results also show that the presence of methoxy group in the phenolic compounds may not be necessary for Agrobacterium vir gene induction and receptor binding as suggested by previous studies. These findings provide possible alternative Agrobacterium vir gene inducers that are more potent as compared to the commonly used acetosyringone in achieving high efficiency of Agrobacterium-mediated transformation in microalgae and possibly for other plants.

  7. Assay of phenolic compounds from four species of Ber (Ziziphus mauritiana L.) Fruits: Comparision of three base hydrolysis procedure for quantification of total phenolic acids

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The present study was undertaken to investigate the flavonoids profile in four species of ber (Ziziphus mauritiana Lamk) fruit and to compare various techniques for the analysis of total phenolic acids. The 12 flavonoids identified were quercetin 3-O-robinobioside, quercetin 3-O-rutinoside, querceti...

  8. Anaerobic Degradation of Phenolic Compounds

    NASA Astrophysics Data System (ADS)

    Schink, B.; Philipp, B.; Müller, J.

    Mononuclear aromatic compounds are degraded anaerobically through three main pathways, the benzoyl-CoA pathway, the resorcinol pathway, and the phloroglucinol pathway. Various modification reactions channel a broad variety of mononuclear aromatics including aromatic hydrocarbons into either one of these three pathways. Recently, a further pathway was discovered with hydroxyhydroquinone as central intermediate through which especially nitrate-reducing bacteria degrade phenolic compounds and some hydroxylated benzoates. Comparison of the various strategies taken for the degradation of aromatics in the absence of oxygen demonstrates that the biochemistry of breakdown of these compounds is determined largely by the overall reaction energetics and, more precisely, by the redox potentials of the electron acceptor systems used. Nitrate reducers differ in their strategies significantly from those used by sulfate-reducing or fermenting bacteria.

  9. Effect of stevia and citric acid on the stability of phenolic compounds and in vitro antioxidant and antidiabetic capacity of a roselle (Hibiscus sabdariffa L.) beverage.

    PubMed

    Pérez-Ramírez, Iza F; Castaño-Tostado, Eduardo; Ramírez-de León, José A; Rocha-Guzmán, Nuria E; Reynoso-Camacho, Rosalía

    2015-04-01

    Plant infusions are consumed due to their beneficial effects on health, which is attributed to their bioactive compounds content. However, these compounds are susceptible to degradation during processing and storage. The objective of this research was to evaluate the effect of stevia and citric acid on the stability of phenolic compounds, antioxidant capacity and carbohydrate-hydrolysing enzyme inhibitory activity of roselle beverages during storage. The optimum extraction conditions of roselle polyphenolic compounds was of 95 °C/60 min, which was obtained by a second order experimental design. The incorporation of stevia increased the stability of colour and some polyphenols, such as quercetin, gallic acid and rosmarinic acid, during storage. In addition, stevia decreased the loss of ABTS, DPPH scavenging activity and α-amylase inhibitory capacity, whereas the incorporation of citric acid showed no effect. These results may contribute to the improvement of technological processes for the elaboration of hypocaloric and functional beverages.

  10. Colour Evaluation, Bioactive Compound Content, Phenolic Acid Profiles and in Vitro Biological Activity of Passerina del Frusinate White Wines: Influence of Pre-Fermentative Skin Contact Times.

    PubMed

    Carbone, Katya; Fiordiponti, Luciano

    2016-01-01

    Passerina del Frusinate is an autochthonous wine grape variety, which grows in the Lazio region that is currently being evaluated by local wine producers. In this study, colour properties (CIELab coordinates), bioactive compounds (total polyphenols and flavan-3-ols), HPLC-DAD phenolic acid profiles and in vitro biological activity of monovarietal Passerina del Frusinate white wines and the effect of different maceration times (0, 18 and 24 h) were evaluated based on these parameters. Results highlighted statistically significant differences for almost all analysed parameters due to a strong influence of the pre-fermentative skin contact time. The flavan content of macerated wines was six times higher than that of the control, while total polyphenols were 1.5 times higher. According to their phytochemical content, macerated wines showed the highest antiradical capacity tested by means of DPPH(•) and ABTS(+•) assays. Besides, prolonged maceration resulted in a reduction of CIELab coordinates as well as of the content of phenolic substances and antiradical capacity. Among the phenolic acids analysed, the most abundant were vanillic acid and caffeic acid; the latter proved to be the most susceptible to degradation as a result of prolonged maceration. Passerina del Frusinate appears as a phenol-rich white wine with a strong antioxidant potential similar to that of red wines. PMID:27455227

  11. Phenolic compounds, organic acids and antioxidant activity of grape juices produced from new Brazilian varieties planted in the Northeast Region of Brazil.

    PubMed

    Lima, Marcos Dos Santos; Silani, Igor de Souza Veras; Toaldo, Isabela Maia; Corrêa, Luiz Claudio; Biasoto, Aline Camarão Telles; Pereira, Giuliano Elias; Bordignon-Luiz, Marilde T; Ninow, Jorge Luiz

    2014-10-15

    The phenolic compounds, organic acids and the antioxidant activity were determined for grape juice samples from new Brazilian varieties grown in the Sub-middle São Francisco Valley in the Northeast Region of Brazil. The results showed that the Brazilian grape juices have high antioxidant activity, which was significantly correlated with the phenolic compounds catechin, epicatechin gallate, procyanidin B1, rutin, gallic acid, caffeic acid, p-coumaric acid, pelargonidin-3-glucoside, cyanidin-3-glucoside, cyaniding-3,5-diglucoside and delphinidin-3-glucoside. The produced juice samples showed higher concentrations of trans-resveratrol than those observed in juices made from different varieties of grapes from traditional growing regions. Organic acids concentrations were similar to those of juices produced from other classical varieties. It was demonstrated that it is possible to prepare juices from grapes of new varieties grown in the Northeast of Brazil containing a high content of bioactive compounds and typical characteristics of the tropical viticulture practised in the Sub-middle São Francisco Valley.

  12. Effect of drying of jujubes ( Ziziphus jujuba Mill.) on the contents of sugars, organic acids, α-tocopherol, β-carotene, and phenolic compounds.

    PubMed

    Gao, Qing-Han; Wu, Chun-Sen; Wang, Min; Xu, Bian-Na; Du, Li-Juan

    2012-09-26

    This study investigated the changes in sugars, organic acids, α-tocopherol, β-carotene, phenolic profiles, total phenolic content (TPC), and antioxidant capacity of jujube fruits after four drying treatments (sun-, oven-, microwave- and freeze-drying). Sugar, organic acid, phenolic compounds, α-tocopherol, and β-carotene were qualitatived and quantitatived by high-performance liquid chromatography. The TPC and antioxidant activity of jujube samples were evaluated using the Folin-Ciocalteau method and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical scavenging activity, respectively. Freeze-drying resulted in jujubes with higher antioxidant activity and was also a good choice for the preparation of β-carotene from jujubes for the food industry. Microwave-dried jujubes had a higher content of protocatechuic acid, catechin, and epicatechin and maintained the same antioxidant capacity with the freeze-dried jujubes. The combination of microwave- and freeze-drying may be an efficient alternative with shorter processing time and, consequently, less impact on the nutritional value of the jujube.

  13. Phenolic compound in beans as protection against mycotoxins.

    PubMed

    Telles, Annie Campello; Kupski, Larine; Furlong, Eliana Badiale

    2017-01-01

    Phenolic compounds, their inhibitory activity against fungal amylase and the occurrence of aflatoxins were determined in edible beans. The free, conjugated and bounded phenolic compounds and their phenolic acid profiles were determined in ten bean varieties. A method for aflatoxin B1, B2, G1 and G2 determination and confirmation by LC-MS/MS was validated. The red and carioca beans presented the highest total phenolic content (1.8 and 1.2mg.g(-1), respectively); the fradinho and white beans the lowest (0.18 and 0.19mg.g(-1), respectively). In the free and conjugated forms, chlorogenic acid was present in 60% of the samples, while in the bounded phenolic, ferulic acid was in 90% of the samples. The phenolic extracts were able to inhibit fungal amylase, and the PCA analysis confirmed that the relation between the chlorogenic and gallic acids is important to this effect. The absence of aflatoxins in samples confirm the protector effects of these phenolic compounds.

  14. Phenolic compound in beans as protection against mycotoxins.

    PubMed

    Telles, Annie Campello; Kupski, Larine; Furlong, Eliana Badiale

    2017-01-01

    Phenolic compounds, their inhibitory activity against fungal amylase and the occurrence of aflatoxins were determined in edible beans. The free, conjugated and bounded phenolic compounds and their phenolic acid profiles were determined in ten bean varieties. A method for aflatoxin B1, B2, G1 and G2 determination and confirmation by LC-MS/MS was validated. The red and carioca beans presented the highest total phenolic content (1.8 and 1.2mg.g(-1), respectively); the fradinho and white beans the lowest (0.18 and 0.19mg.g(-1), respectively). In the free and conjugated forms, chlorogenic acid was present in 60% of the samples, while in the bounded phenolic, ferulic acid was in 90% of the samples. The phenolic extracts were able to inhibit fungal amylase, and the PCA analysis confirmed that the relation between the chlorogenic and gallic acids is important to this effect. The absence of aflatoxins in samples confirm the protector effects of these phenolic compounds. PMID:27507478

  15. Radiation induced chemical changes of phenolic compounds in strawberries

    NASA Astrophysics Data System (ADS)

    Breitfellner, F.; Solar, S.; Sontag, G.

    2003-06-01

    In unirradiated strawberries four phenolic acids (gallic acid, p-coumaric acid, caffeic acid and 4-hydroxybenzoic acid), the flavonoids (+)-catechin, (-)-epicatechin and glycosides from kaempferol and quercetin were determined by reversed phase chromatography with diode array detection. Characteristic linear dose/concentration relationships were found for 4-hydroxybenzoic acid and two unidentified compounds. One of them may be usable as marker to prove an irradiation treatment.

  16. Consumption of argan oil (Morocco) with its unique profile of fatty acids, tocopherols, squalene, sterols and phenolic compounds should confer valuable cancer chemopreventive effects.

    PubMed

    Khallouki, F; Younos, C; Soulimani, R; Oster, T; Charrouf, Z; Spiegelhalder, B; Bartsch, H; Owen, R W

    2003-02-01

    The aim of this study was to evaluate the fatty acids, tocopherols, squalene, sterols and phenolic antioxidants in three types of argan oil (Moroccan food, Moroccan aesthetic and a French commercial variety) along with a basic comparison with extra virgin olive and sunflower oil. The fatty acid profiles in the argan oils were very similar, with oleic acid (43%) and linoleic acid (36%) and their respective monoacylglycerols predominating. The major vitamer identified was -tocopherol with a mean of 483+/-11 mg/kg, in contrast to -tocopherol, which is the major vitamer in olive (190+/-1 mg/kg) and sunflower oil (532+/-6 mg/kg). The squalene content of the argan oils was very similar with a mean of 313+/-4 mg/100 g, which is lower than that of the olive oil (499 mg/100 g) but significantly higher than in the sunflower oil (6 mg/100 g). In contrast to olive and sunflower oils in which -sitosterol is predominant, the major sterols detected in the argan oils were schottenol (mean 147+/-10 mg/kg) and spinasterol (mean 122+/-10 mg/kg). The only phenolic compounds other than the tocopherol vitamers which could be readily detected and quantitated were vanillic, syringic and ferulic (probably conjugated to glucose) acids along with tyrosol. In contrast to the extra virgin olive oil (793 mg/kg), the concentration of total phenolic compounds is extremely low (<5.0 mg/kg). Nevertheless, argan oil with its high content of the vitamer -tocopherol, squalene and oleic acid is likely to enhance the cancer prevention effects of the Moroccan diet.

  17. Modulation of Pb-induced stress in Prosopis shoots through an interconnected network of signaling molecules, phenolic compounds and amino acids.

    PubMed

    Zafari, Somaieh; Sharifi, Mohsen; Ahmadian Chashmi, Najmeh; Mur, Luis A J

    2016-02-01

    Lead (Pb) is a hazardous heavy metal present in the environment which elicits oxidative stress in plants. To characterize the physiological and biochemical basis of Pb tolerance, Prosopis farcta seedlings were exposed to Hoagland's solutions at six different Pb concentrations (0, 80, 160, 320, 400 and 480 μM) for different periods of time. As expected, application of Pb significantly increased hydrogen peroxide (H2O2) content. In response, P. farcta deployed the antioxidative defence mechanisms with significantly higher activities of superoxide dismutase (SOD), enzymes related to H2O2 removal, and also the increases in proline as a solute marker of stress. Increases were observed in nitric oxide (NO) production which could also act in triggering defense functions to detoxify Pb. Enhanced phenylalanine ammonia-lyase (PAL) activity at early days of exposure to Pb was correlated with increases in phenolic compounds. Significant increases in phenolic acids and flavonoids; daidzein, vitexin, ferulic acid and salicylic acid were observed with Pb treatment. Furthermore, the stress effects were followed by changes in free amino acid content and composition. Aspartic acid and glycine content was increased but glutamic acid significantly decreased. It is likely that stress signal transduction by NO and H2O2 mediated defence responses to Pb by coordination of antioxidative system and metabolic pathways of phenylpropanoid and amino acids.

  18. Isolation and identification of plant phenolic compounds in birch leaves: Air pollution stress and leaf phenolics

    NASA Astrophysics Data System (ADS)

    Loponen, Jyrki Mikael

    Chromatographic (analytical and preparative HPLC), chemical (hydrolysis) and spectroscopic (UV, 1H NMR, 13C NMR and MS) techniques proved to be suitable tools for the structure identification of plant phenolic compounds. More than 30 individual phenolic compounds were detected and quantified. Detailed information of the structures of individual compounds was determined after isolation from birch leaves. Ten flavonoid glycosides were identified. Two of them, myricetin-3-O-α-L-(acetyl)-rhamnopyranoside and quercetin-3-O-α-L-(4/prime'-O-acetyl)- rhamnopyranoside, have been rarely found in birch leaves. Further, some characterized major phenolics with non- flavonoid structures in our study were 1-O-galloyl- β-D-(2-O-acetyl)-glucopyranose, gallic, chlorogenic, neochlorogenic, cis- and trans-forms of 3- and 5-p-coumaroylquinic acids. The presence of gallotannin group was evidenced by strong positive correlations between concentrations of these gallotannins (preliminary identified by HPLC and UV spectra) and the protein precipitation capacity of extracts. Content of gallotannins decreased with leaf growth and maturation. It is known that concentrations of phenolic compounds regularly increase in slowly growing stressed plants and therefore, it is natural that they are also sensitive to different forms of air pollution. Total content and the contents of some individual phenolics correlated negatively with the distance from the pollution source in our study area. In addition to comparing absolute concentrations of compounds in question, the within-tree correlations or within-tree variations of the relevant compounds between polluted and control areas were an alternative approach. Differences in pairwise correlations between the investigated leaf phenolic compounds indicated the competition between some gallotannins and p-coumaroylquinic acids on the polluted but not on the control site. Air pollution seems to be a stress factor for birch trees associated with

  19. Phenolic Compounds in the Potato and Its Byproducts: An Overview.

    PubMed

    Akyol, Hazal; Riciputi, Ylenia; Capanoglu, Esra; Caboni, Maria Fiorenza; Verardo, Vito

    2016-01-01

    The potato (Solanum tuberosum L.) is a tuber that is largely used for food and is a source of different bioactive compounds such as starch, dietary fiber, amino acids, minerals, vitamins, and phenolic compounds. Phenolic compounds are synthetized by the potato plant as a protection response from bacteria, fungi, viruses, and insects. Several works showed that these potato compounds exhibited health-promoting effects in humans. However, the use of the potato in the food industry submits this vegetable to different processes that can alter the phenolic content. Moreover, many of these compounds with high bioactivity are located in the potato's skin, and so are eliminated as waste. In this review the most recent articles dealing with phenolic compounds in the potato and potato byproducts, along with the effects of harvesting, post-harvest, and technological processes, have been reviewed. Briefly, the phenolic composition, main extraction, and determination methods have been described. In addition, the "alternative" food uses and healthy properties of potato phenolic compounds have been addressed. PMID:27240356

  20. Phenolic Compounds in the Potato and Its Byproducts: An Overview.

    PubMed

    Akyol, Hazal; Riciputi, Ylenia; Capanoglu, Esra; Caboni, Maria Fiorenza; Verardo, Vito

    2016-05-27

    The potato (Solanum tuberosum L.) is a tuber that is largely used for food and is a source of different bioactive compounds such as starch, dietary fiber, amino acids, minerals, vitamins, and phenolic compounds. Phenolic compounds are synthetized by the potato plant as a protection response from bacteria, fungi, viruses, and insects. Several works showed that these potato compounds exhibited health-promoting effects in humans. However, the use of the potato in the food industry submits this vegetable to different processes that can alter the phenolic content. Moreover, many of these compounds with high bioactivity are located in the potato's skin, and so are eliminated as waste. In this review the most recent articles dealing with phenolic compounds in the potato and potato byproducts, along with the effects of harvesting, post-harvest, and technological processes, have been reviewed. Briefly, the phenolic composition, main extraction, and determination methods have been described. In addition, the "alternative" food uses and healthy properties of potato phenolic compounds have been addressed.

  1. Phenolic Compounds in the Potato and Its Byproducts: An Overview

    PubMed Central

    Akyol, Hazal; Riciputi, Ylenia; Capanoglu, Esra; Caboni, Maria Fiorenza; Verardo, Vito

    2016-01-01

    The potato (Solanum tuberosum L.) is a tuber that is largely used for food and is a source of different bioactive compounds such as starch, dietary fiber, amino acids, minerals, vitamins, and phenolic compounds. Phenolic compounds are synthetized by the potato plant as a protection response from bacteria, fungi, viruses, and insects. Several works showed that these potato compounds exhibited health-promoting effects in humans. However, the use of the potato in the food industry submits this vegetable to different processes that can alter the phenolic content. Moreover, many of these compounds with high bioactivity are located in the potato’s skin, and so are eliminated as waste. In this review the most recent articles dealing with phenolic compounds in the potato and potato byproducts, along with the effects of harvesting, post-harvest, and technological processes, have been reviewed. Briefly, the phenolic composition, main extraction, and determination methods have been described. In addition, the “alternative” food uses and healthy properties of potato phenolic compounds have been addressed. PMID:27240356

  2. Avocado roots treated with salicylic acid produce phenol-2,4-bis (1,1-dimethylethyl), a compound with antifungal activity.

    PubMed

    Rangel-Sánchez, Gerardo; Castro-Mercado, Elda; García-Pineda, Ernesto

    2014-02-15

    We demonstrated the ability of salicylic acid (SA) to induce a compound in avocado roots that strengthens their defense against Phytophthora cinnamomi. The SA content of avocado roots, before and after the application of exogenous SA, was determined by High-Performance Liquid Chromatography (HPLC). After 4h of SA feeding, the endogenous level in the roots increased to 223 μg g(-1) FW, which was 15 times the amount found in control roots. The methanolic extract obtained from SA-treated avocado roots inhibited the radial growth of P. cinnamomi. A thin layer chromatographic bioassay with the methanolic extract and spores of Aspergillus showed a distinct inhibition zone. The compound responsible for the inhibition was identified as phenol-2,4-bis (1,1-dimethylethyl) by gas chromatography and mass spectrometry. At a concentration of 100 μg/mL, the substance reduced germinative tube length in Aspergillus and radial growth of P. cinnamomi. A commercial preparation of phenol-2,4-bis (1,1-dimethylethyl) caused the same effects on mycelium morphology and radial growth as our isolate, confirming the presence of this compound in the root extracts. This is the first report of the induction of this compound in plants by SA, and the results suggest that it plays an important role in the defense response of avocado.

  3. Process for producing phenolic compounds from lignins

    DOEpatents

    Agblevor, Foster A.

    1998-01-01

    A process for the production of low molecular weight phenolic compounds from lignins through the pyrolysis of the lignins in the presence of a strong base. In a preferred embodiment, potassium hydroxide is present in an amount of from about 0.1% to about 5% by weight, the pyrolysis temperature is from about 400.degree. C. to about 600.degree. C. at atmospheric pressure, and the time period for substantial completion of the reaction is from about 1-3 minutes. Examples of low molecular weight phenolic compounds produced include methoxyphenols, non-methoxylated phenols, and mixtures thereof.

  4. Process for producing phenolic compounds from lignins

    DOEpatents

    Agblevor, F.A.

    1998-09-15

    A process is described for the production of low molecular weight phenolic compounds from lignins through the pyrolysis of the lignins in the presence of a strong base. In a preferred embodiment, potassium hydroxide is present in an amount of from about 0.1% to about 5% by weight, the pyrolysis temperature is from about 400 C to about 600 C at atmospheric pressure, and the time period for substantial completion of the reaction is from about 1--3 minutes. Examples of low molecular weight phenolic compounds produced include methoxyphenols, non-methoxylated phenols, and mixtures thereof. 16 figs.

  5. Phenolic compounds and antioxidant capacity of virgin olive oil.

    PubMed

    Franco, Ma Nieves; Galeano-Díaz, Teresa; López, Oscar; Fernández-Bolaños, José G; Sánchez, Jacinto; De Miguel, Concepción; Gil, Ma Victoria; Martín-Vertedor, Daniel

    2014-11-15

    The characterisation of virgin olive oil from Arbequina, Carrasqueña, Corniche, Manzanilla Cacereña, Morisca, Picual, and Verdial de Badajoz varieties according to the individual phenolic compounds at different ripening stage was carried out. In all olive oil varieties studied, secoiridoid derivatives were most abundant, followed by phenolic alcohols, flavonoids and phenolic acids. The secoiridoid derivatives of hydroxytyrosol were the most important complex phenols for Picual and Carrasqueña, whereas the tyrosol derivatives were the major ones found in Manzanilla Cacereña, and Verdial de Badajoz. For secoiridoid derivatives of hydroxytyrosol and tyrosol, Arbequina was the oil variety showing the lowest concentration. Tyrosol, hydroxytyrosol, vanillic acid, p-cumaric acid, luteolin, and apigenin levels were greater in early harvested samples in almost all oils analysed. Antioxidant activity measurements (antiradical, lipid peroxide inhibition, H2O2 and NO scavenging) were also accomplished for the seven varieties in the first ripening stage.

  6. Phenolic compounds and antioxidant capacity of virgin olive oil.

    PubMed

    Franco, Ma Nieves; Galeano-Díaz, Teresa; López, Oscar; Fernández-Bolaños, José G; Sánchez, Jacinto; De Miguel, Concepción; Gil, Ma Victoria; Martín-Vertedor, Daniel

    2014-11-15

    The characterisation of virgin olive oil from Arbequina, Carrasqueña, Corniche, Manzanilla Cacereña, Morisca, Picual, and Verdial de Badajoz varieties according to the individual phenolic compounds at different ripening stage was carried out. In all olive oil varieties studied, secoiridoid derivatives were most abundant, followed by phenolic alcohols, flavonoids and phenolic acids. The secoiridoid derivatives of hydroxytyrosol were the most important complex phenols for Picual and Carrasqueña, whereas the tyrosol derivatives were the major ones found in Manzanilla Cacereña, and Verdial de Badajoz. For secoiridoid derivatives of hydroxytyrosol and tyrosol, Arbequina was the oil variety showing the lowest concentration. Tyrosol, hydroxytyrosol, vanillic acid, p-cumaric acid, luteolin, and apigenin levels were greater in early harvested samples in almost all oils analysed. Antioxidant activity measurements (antiradical, lipid peroxide inhibition, H2O2 and NO scavenging) were also accomplished for the seven varieties in the first ripening stage. PMID:24912728

  7. Enhancing charge storage of conjugated polymer electrodes with phenolic acids

    NASA Astrophysics Data System (ADS)

    Wagner, Michal; Rębiś, Tomasz; Inganäs, Olle

    2016-01-01

    We here present studies of electrochemical doping of poly(1-aminoanthraquinone) (PAAQ) films with three structurally different phenolic acids. The examined phenolic acids (sinapic, ferulic and syringic acid) were selected due to their resemblance to redox active groups, which can be found in lignin. The outstanding electrochemical stability of PAAQ films synthesized for this work enabled extensive cycling of phenolic acid-doped PAAQ films. Potentiodynamic and charge-discharge studies revealed that phenolic acid-doped PAAQ films exhibited enhanced capacitance in comparison to undoped PAAQ films, together with appearance of redox activity characteristics specific for each dopant. Electrochemical kinetic studies performed on microelectrodes affirmed the fast electron transfer for hydroquinone-to-quinone reactions with these phenolic compounds. These results imply the potential application of phenolic acids in cheap and degradable energy storage devices.

  8. Enzymatic oxidation of phenolic compounds in coffee processing wastewater.

    PubMed

    Torres, Juliana Arriel; Batista Chagas, Pricila Maria; Silva, Maria Cristina; dos Santos, Custódio Donizete; Duarte Corrêa, Angelita

    2016-01-01

    Peroxidases can be used in the treatment of wastewater containing phenolic compounds. The effluent from the wet processing of coffee fruits contains high content of these pollutants and although some studies propose treatments for this wastewater, none targets specifically the removal of these recalcitrant compounds. This study evaluates the potential use of different peroxidase sources in the oxidation of caffeic acid and of total phenolic compounds in coffee processing wastewater (CPW). The identification and quantification of phenolic compounds in CPW was performed and caffeic acid was found to be the major phenolic compound. Some factors, such as reaction time, pH, amount of H2O2 and enzyme were evaluated, in order to determine the optimum conditions for the enzyme performance for maximum oxidation of caffeic acid. The turnip peroxidase (TPE) proved efficient in the removal of caffeic acid, reaching an oxidation of 51.05% in just 15 minutes of reaction. However, in the bioremediation of the CPW, the horseradish peroxidase (HRP) was more efficient with 32.70%±0.16 of oxidation, followed by TPE with 18.25%±0.11. The treatment proposed in this work has potential as a complementary technology, since the efficiency of the existing process is intimately conditioned to the presence of these pollutants.

  9. Enzymatic oxidation of phenolic compounds in coffee processing wastewater.

    PubMed

    Torres, Juliana Arriel; Batista Chagas, Pricila Maria; Silva, Maria Cristina; dos Santos, Custódio Donizete; Duarte Corrêa, Angelita

    2016-01-01

    Peroxidases can be used in the treatment of wastewater containing phenolic compounds. The effluent from the wet processing of coffee fruits contains high content of these pollutants and although some studies propose treatments for this wastewater, none targets specifically the removal of these recalcitrant compounds. This study evaluates the potential use of different peroxidase sources in the oxidation of caffeic acid and of total phenolic compounds in coffee processing wastewater (CPW). The identification and quantification of phenolic compounds in CPW was performed and caffeic acid was found to be the major phenolic compound. Some factors, such as reaction time, pH, amount of H2O2 and enzyme were evaluated, in order to determine the optimum conditions for the enzyme performance for maximum oxidation of caffeic acid. The turnip peroxidase (TPE) proved efficient in the removal of caffeic acid, reaching an oxidation of 51.05% in just 15 minutes of reaction. However, in the bioremediation of the CPW, the horseradish peroxidase (HRP) was more efficient with 32.70%±0.16 of oxidation, followed by TPE with 18.25%±0.11. The treatment proposed in this work has potential as a complementary technology, since the efficiency of the existing process is intimately conditioned to the presence of these pollutants. PMID:26744933

  10. Synergistic anti-Campylobacter jejuni activity of fluoroquinolone and macrolide antibiotics with phenolic compounds

    PubMed Central

    Oh, Euna; Jeon, Byeonghwa

    2015-01-01

    The increasing resistance of Campylobacter to clinically important antibiotics, such as fluoroquinolones and macrolides, is a serious public health problem. The objective of this study is to investigate synergistic anti-Campylobacter jejuni activity of fluoroquinolones and macrolides in combination with phenolic compounds. Synergistic antimicrobial activity was measured by performing a checkerboard assay with ciprofloxacin and erythromycin in the presence of 21 phenolic compounds. Membrane permeability changes in C. jejuni by phenolic compounds were determined by measuring the level of intracellular uptake of 1-N-phenylnaphthylamine (NPN). Antibiotic accumulation assays were performed to evaluate the level of ciprofloxacin accumulation in C. jejuni. Six phenolic compounds, including p-coumaric acid, sinapic acid, caffeic acid, vanillic acid, gallic acid, and taxifolin, significantly increased the susceptibility to ciprofloxacin and erythromycin in several human and poultry isolates. The synergistic antimicrobial effect was also observed in ciprofloxacin- and erythromycin-resistant C. jejuni strains. The phenolic compounds also substantially increased membrane permeability and antibiotic accumulation in C. jejuni. Interestingly, some phenolic compounds, such as gallic acid and taxifolin, significantly reduced the expression of the CmeABC multidrug efflux pump. Phenolic compounds increased the NPN accumulation in the cmeB mutant, indicating phenolic compounds may affect the membrane permeability. In this study, we successfully demonstrated that combinational treatment of C. jejuni with antibiotics and phenolic compounds synergistically inhibits C. jejuni by impacting both antimicrobial influx and efflux. PMID:26528273

  11. Synergistic anti-Campylobacter jejuni activity of fluoroquinolone and macrolide antibiotics with phenolic compounds.

    PubMed

    Oh, Euna; Jeon, Byeonghwa

    2015-01-01

    The increasing resistance of Campylobacter to clinically important antibiotics, such as fluoroquinolones and macrolides, is a serious public health problem. The objective of this study is to investigate synergistic anti-Campylobacter jejuni activity of fluoroquinolones and macrolides in combination with phenolic compounds. Synergistic antimicrobial activity was measured by performing a checkerboard assay with ciprofloxacin and erythromycin in the presence of 21 phenolic compounds. Membrane permeability changes in C. jejuni by phenolic compounds were determined by measuring the level of intracellular uptake of 1-N-phenylnaphthylamine (NPN). Antibiotic accumulation assays were performed to evaluate the level of ciprofloxacin accumulation in C. jejuni. Six phenolic compounds, including p-coumaric acid, sinapic acid, caffeic acid, vanillic acid, gallic acid, and taxifolin, significantly increased the susceptibility to ciprofloxacin and erythromycin in several human and poultry isolates. The synergistic antimicrobial effect was also observed in ciprofloxacin- and erythromycin-resistant C. jejuni strains. The phenolic compounds also substantially increased membrane permeability and antibiotic accumulation in C. jejuni. Interestingly, some phenolic compounds, such as gallic acid and taxifolin, significantly reduced the expression of the CmeABC multidrug efflux pump. Phenolic compounds increased the NPN accumulation in the cmeB mutant, indicating phenolic compounds may affect the membrane permeability. In this study, we successfully demonstrated that combinational treatment of C. jejuni with antibiotics and phenolic compounds synergistically inhibits C. jejuni by impacting both antimicrobial influx and efflux.

  12. [Phenolic acid derivatives from Alchornea trewioides].

    PubMed

    Qin, Ri-Dong; Cheng, Wei; Zhang, Qing-Ying; Liang, Hong

    2012-07-01

    To study the chemical constituents of Alchornea trewioides, silica gel column chromatography, Sephadex LH-20, reverse phase ODS column chromatography, MCI and semi-preparative HPLC were used to separate the 95% EtOH extract of the root of Alchornea trewioides. The structures were elucidated on the basis of spectroscopic studies including ESI-TOF-MS, 1H NMR, 13C NMR, HSQC and HMBC. Eight phenolic acids were obtained and identified as 1-O-galloyl-6-O-vanilloyl-beta-glucose (1), gallic acid (2), ethyl gallate (3), syringic acid (4), glucosyringic acid (5), erigeside C (6), 3, 4-dimethoxyphenyl-(6'-O-alpha-L-rhamnosyl)-beta-D-glucopyranoside (7) and 3, 4, 5-trimethoxyphenyl-(6'-O-galloyl)-O-beta-D-glucopyranoside (8). Among them, compound 1 is a new compound, compounds 4-8 are isolated from the genus Alchornea for the first time, and the others are isolated from the plant for the first time.

  13. Bismuth nanoparticles for phenolic compounds biosensing application.

    PubMed

    Mayorga-Martinez, Carmen C; Cadevall, Miquel; Guix, Maria; Ros, Josep; Merkoçi, Arben

    2013-02-15

    The rapid determination of trace phenolic compounds is of great importance for evaluating the total toxicity of contaminated water samples. Nowadays, electrochemical tyrosinase (Tyr) based biosensors constitute a promising technology for the in situ monitoring of phenolic compounds because of their advantages such as high selectivity, low production cost, promising response speed, potential for miniaturization, simple instrumentation and easy automatization. A mediator-free amperometric biosensor for phenolic compounds detection based on the combination of bismuth nanoparticles (BiNPs) and Tyr for phenol detections will be hereby reported. This is achieved through the integration of BiNPs/Tyr onto the working electrode of a screen printed electrode (SPE) by using glutaraldehyde as a cross-linking agent. BiNPs/Tyr biosensor is evaluated by amperometric measurements at -200 mV DC and a linear range of up to 71 μM and 100 μM and a correlation coefficient of 0.995 and 0.996 for phenol and catechol, respectively. The very low DC working potential ensures the avoidance of interferences making this biosensor an advantageous device for real sample applications. In addition, the response mechanism including the effect of BiNPs based on electrochemical studies and optical characterizations will be also discussed. The obtained results may open the way to many other BiNPs applications in the biosensing field.

  14. Antioxidant phenolic compounds of cassava (Manihot esculenta) from Hainan.

    PubMed

    Yi, Bo; Hu, Lifei; Mei, Wenli; Zhou, Kaibing; Wang, Hui; Luo, Ying; Wei, Xiaoyi; Dai, Haofu

    2011-12-07

    An activity-directed fractionation and purification process was used to isolate antioxidant components from cassava stems produced in Hainan. The ethyl acetate and n-butanol fractions showed greater DPPH˙and ABTS·+ scavenging activities than other fractions. The ethyl acetate fraction was subjected to column chromatography, to yield ten phenolic compounds: Coniferaldehyde (1), isovanillin (2), 6-deoxyjacareubin (3), scopoletin (4), syringaldehyde (5), pinoresinol (6), p-coumaric acid (7), ficusol (8), balanophonin (9) and ethamivan (10), which possess significant antioxidant activities. The relative order of DPPH· scavenging capacity for these compounds was ascorbic acid (reference) > 6 > 1 > 8 > 10 > 9 > 3 > 4 > 7 > 5 > 2, and that of ABTS·+ scavenging capacity was 5 > 7 > 1 > 10 > 4 > 6 > 8 > 2 > Trolox (reference compound) > 3 > 9. The results showed that these phenolic compounds contributed to the antioxidant activity of cassava.

  15. Phenolic compounds in ectomycorrhizal interaction of lignin modified silver birch

    PubMed Central

    Sutela, Suvi; Niemi, Karoliina; Edesi, Jaanika; Laakso, Tapio; Saranpää, Pekka; Vuosku, Jaana; Mäkelä, Riina; Tiimonen, Heidi; Chiang, Vincent L; Koskimäki, Janne; Suorsa, Marja; Julkunen-Tiitto, Riitta; Häggman, Hely

    2009-01-01

    Background The monolignol biosynthetic pathway interconnects with the biosynthesis of other secondary phenolic metabolites, such as cinnamic acid derivatives, flavonoids and condensed tannins. The objective of this study is to evaluate whether genetic modification of the monolignol pathway in silver birch (Betula pendula Roth.) would alter the metabolism of these phenolic compounds and how such alterations, if exist, would affect the ectomycorrhizal symbiosis. Results Silver birch lines expressing quaking aspen (Populus tremuloides L.) caffeate/5-hydroxyferulate O-methyltransferase (PtCOMT) under the 35S cauliflower mosaic virus (CaMV) promoter showed a reduction in the relative expression of a putative silver birch COMT (BpCOMT) gene and, consequently, a decrease in the lignin syringyl/guaiacyl composition ratio. Alterations were also detected in concentrations of certain phenolic compounds. All PtCOMT silver birch lines produced normal ectomycorrhizas with the ectomycorrhizal fungus Paxillus involutus (Batsch: Fr.), and the formation of symbiosis enhanced the growth of the transgenic plants. Conclusion The down-regulation of BpCOMT in the 35S-PtCOMT lines caused a reduction in the syringyl/guaiacyl ratio of lignin, but no significant effect was seen in the composition or quantity of phenolic compounds that would have been caused by the expression of PtCOMT under the 35S or UbB1 promoter. Moreover, the detected alterations in the composition of lignin and secondary phenolic compounds had no effect on the interaction between silver birch and P. involutus. PMID:19788757

  16. Phenolic Compounds and Antioxidant Activity of Phalaenopsis Orchid Hybrids

    PubMed Central

    Minh, Truong Ngoc; Khang, Do Tan; Tuyen, Phung Thi; Minh, Luong The; Anh, La Hoang; Quan, Nguyen Van; Ha, Pham Thi Thu; Quan, Nguyen Thanh; Toan, Nguyen Phu; Elzaawely, Abdelnaser Abdelghany; Xuan, Tran Dang

    2016-01-01

    Phalaenopsis spp. is the most commercially and economically important orchid, but their plant parts are often left unused, which has caused environmental problems. To date, reports on phytochemical analyses were most available on endangered and medicinal orchids. The present study was conducted to determine the total phenolics, total flavonoids, and antioxidant activity of ethanol extracts prepared from leaves and roots of six commercial hybrid Phalaenopsis spp. Leaf extracts of “Chian Xen Queen” contained the highest total phenolics with a value of 11.52 ± 0.43 mg gallic acid equivalent per g dry weight and the highest total flavonoids (4.98 ± 0.27 mg rutin equivalent per g dry weight). The antioxidant activity of root extracts evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging assay and β-carotene bleaching method was higher than those of the leaf extracts. Eleven phenolic compounds were identified, namely, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, syringic acid, vanillin, ferulic acid, sinapic acid, p-coumaric acid, benzoic acid, and ellagic acid. Ferulic, p-coumaric and sinapic acids were concentrated largely in the roots. The results suggested that the root extracts from hybrid Phalaenopsis spp. could be a potential source of natural antioxidants. This study also helps to reduce the amount of this orchid waste in industrial production, as its roots can be exploited for pharmaceutical purposes. PMID:27649250

  17. Phenolic Compounds and Antioxidant Activity of Phalaenopsis Orchid Hybrids.

    PubMed

    Minh, Truong Ngoc; Khang, Do Tan; Tuyen, Phung Thi; Minh, Luong The; Anh, La Hoang; Quan, Nguyen Van; Ha, Pham Thi Thu; Quan, Nguyen Thanh; Toan, Nguyen Phu; Elzaawely, Abdelnaser Abdelghany; Xuan, Tran Dang

    2016-09-14

    Phalaenopsis spp. is the most commercially and economically important orchid, but their plant parts are often left unused, which has caused environmental problems. To date, reports on phytochemical analyses were most available on endangered and medicinal orchids. The present study was conducted to determine the total phenolics, total flavonoids, and antioxidant activity of ethanol extracts prepared from leaves and roots of six commercial hybrid Phalaenopsis spp. Leaf extracts of "Chian Xen Queen" contained the highest total phenolics with a value of 11.52 ± 0.43 mg gallic acid equivalent per g dry weight and the highest total flavonoids (4.98 ± 0.27 mg rutin equivalent per g dry weight). The antioxidant activity of root extracts evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging assay and β-carotene bleaching method was higher than those of the leaf extracts. Eleven phenolic compounds were identified, namely, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, syringic acid, vanillin, ferulic acid, sinapic acid, p-coumaric acid, benzoic acid, and ellagic acid. Ferulic, p-coumaric and sinapic acids were concentrated largely in the roots. The results suggested that the root extracts from hybrid Phalaenopsis spp. could be a potential source of natural antioxidants. This study also helps to reduce the amount of this orchid waste in industrial production, as its roots can be exploited for pharmaceutical purposes.

  18. Phenolic Compounds and Antioxidant Activity of Phalaenopsis Orchid Hybrids.

    PubMed

    Minh, Truong Ngoc; Khang, Do Tan; Tuyen, Phung Thi; Minh, Luong The; Anh, La Hoang; Quan, Nguyen Van; Ha, Pham Thi Thu; Quan, Nguyen Thanh; Toan, Nguyen Phu; Elzaawely, Abdelnaser Abdelghany; Xuan, Tran Dang

    2016-01-01

    Phalaenopsis spp. is the most commercially and economically important orchid, but their plant parts are often left unused, which has caused environmental problems. To date, reports on phytochemical analyses were most available on endangered and medicinal orchids. The present study was conducted to determine the total phenolics, total flavonoids, and antioxidant activity of ethanol extracts prepared from leaves and roots of six commercial hybrid Phalaenopsis spp. Leaf extracts of "Chian Xen Queen" contained the highest total phenolics with a value of 11.52 ± 0.43 mg gallic acid equivalent per g dry weight and the highest total flavonoids (4.98 ± 0.27 mg rutin equivalent per g dry weight). The antioxidant activity of root extracts evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging assay and β-carotene bleaching method was higher than those of the leaf extracts. Eleven phenolic compounds were identified, namely, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, syringic acid, vanillin, ferulic acid, sinapic acid, p-coumaric acid, benzoic acid, and ellagic acid. Ferulic, p-coumaric and sinapic acids were concentrated largely in the roots. The results suggested that the root extracts from hybrid Phalaenopsis spp. could be a potential source of natural antioxidants. This study also helps to reduce the amount of this orchid waste in industrial production, as its roots can be exploited for pharmaceutical purposes. PMID:27649250

  19. Using phenolic compounds to reduce the allergenic properties of peanut extracts and peanut butter slurries.

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Since phenolic compounds may form insoluble complexes with proteins, we determined that their interaction with peanut allergens leads to a reduction in the allergenic properties of peanut extracts and peanut butter slurries. Phenolics, such as, caffeic acid, chlorogenic acid, and ferulic acid were e...

  20. [Antioxidant and antibacterial activities of dimeric phenol compounds].

    PubMed

    Ogata, Masahiro

    2008-08-01

    We studied the antioxidant and antibacterial activities of monomeric and dimeric phenol compounds. Dimeric compounds had higher antioxidant activities than monomeric compounds. Electron spin resonance spin-trapping experiments showed that phenol compounds with an allyl substituent on their aromatic rings directly scavenged superoxide, and that only eugenol trapped hydroxyl radicals. We developed a generation system of the hydroxyl radical without using any metals by adding L-DOPA and DMPO to PBS or MiliQ water in vitro. We found that eugenol trapped hydroxyl radicals directly and is metabolized to a dimer. On the other hand, dipropofol, a dimer of propofol, has strong antibacterial activity against Gram-positive bacteria. However, it lacks solubility in water and this property is assumed to limit its efficacy. We tried to improve the solubility and found a new solubilization method of dipropofol in water with the addition of a monosaccharide or ascorbic acid.

  1. Phenolic compounds as antioxidants: carbonic anhydrase isoenzymes inhibitors.

    PubMed

    Gülçin, Ilhami; Beydemir, Şükrü

    2013-03-01

    Antioxidant compounds can scavenge free radicals and increase shelf life by retarding the process of lipid peroxidation, which is one of the major reasons for deterioration of food, medicine and pharmaceutical products during processing and storage. An antioxidant molecule has been defined as any substance when found in low concentrations compared to that of an oxidizable substrate significantly delays or inhibits the oxidation. The major antioxidant compounds are especially phenolics and flavonoids, which are responsible for their health benefits. Carbonic anhydrase (EC 4.2.1.1., CA) is a pH regulatory/metabolic enzyme in all life kingdoms, being found in organisms all over the phylogenetic tree. It catalyzes the hydration of carbon dioxide (CO(2)) to bicarbonate (HCO(3) -) and the corresponding dehydration of HCO(3) -in acidic medium with regeneration of CO(2). Also, CA isoforms are found in a variety of tissues where they participate in several important biological processes such as acid-base balance, respiration, carbon dioxide and ion transport, bone resorption, ureagenesis, gluconeogenesis, lipogenesis and electrolyte secretion. On the other hand, the phenyl moiety of phenol was found to lay in the hydrophobic part of the CA active site, where CO(2), the physiologic substrate of the CAs, binds in the precatalytic complex, explaining thus the behavior of phenol as a unique CO(2) competitive inhibitor. This review consists of two main sections. The first section is devoted to main phenolic antioxidant compounds in the foodstuffs and beverages. The second general section is about some definitions of CA inhibitory effects of the main phenolic compounds used for antioxidant activity. The phenolic compounds and acids had marked especially CA I and CA II inhibitory effects and might be used as leads for generating CA isoenzyme inhibitors. This class of compounds may lead to isoform-selective inhibitors targeting just one or few of the medicinally relevant CAs. In

  2. Antinociception produced by Thalassia testudinum extract BM-21 is mediated by the inhibition of acid sensing ionic channels by the phenolic compound thalassiolin B

    PubMed Central

    2011-01-01

    Background Acid-sensing ion channels (ASICs) have a significant role in the sensation of pain and constitute an important target for the search of new antinociceptive drugs. In this work we studied the antinociceptive properties of the BM-21 extract, obtained from the sea grass Thalassia testudinum, in chemical and thermal models of nociception in mice. The action of the BM-21 extract and the major phenolic component isolated from this extract, a sulphated flavone glycoside named thalassiolin B, was studied in the chemical nociception test and in the ASIC currents of the dorsal root ganglion (DRG) neurons obtained from Wistar rats. Results Behavioral antinociceptive experiments were made on male OF-1 mice. Single oral administration of BM-21 produced a significant inhibition of chemical nociception caused by acetic acid and formalin (specifically during its second phase), and increased the reaction time in the hot plate test. Thalassiolin B reduced the licking behavior during both the phasic and tonic phases in the formalin test. It was also found that BM-21 and thalassiolin B selectively inhibited the fast desensitizing (τ < 400 ms) ASIC currents in DRG neurons obtained from Wistar rats, with a nonsignificant action on ASIC currents with a slow desensitizing time-course. The action of thalassiolin B shows no pH or voltage dependence nor is it modified by steady-state ASIC desensitization or voltage. The high concentration of thalassiolin B in the extract may account for the antinociceptive action of BM-21. Conclusions To our knowledge, this is the first report of an ASIC-current inhibitor derived of a marine-plant extract, and in a phenolic compound. The antinociceptive effects of BM-21 and thalassiolin B may be partially because of this action on the ASICs. That the active components of the extract are able to cross the blood-brain barrier gives them an additional advantage for future uses as tools to study pain mechanisms with a potential therapeutic

  3. Effect of cultivar and variety on phenolic compounds and antioxidant activity of cherry wine.

    PubMed

    Xiao, Zuobing; Fang, Lingling; Niu, Yunwei; Yu, Haiyan

    2015-11-01

    To compare the influence of cultivar and variety on the phenolic compounds and antioxidant activity (AA) of cherry wines, total phenolic (TP), total flavonoid (TF), total anthocyanin (TA), total tannin (TT), five individual phenolic acids, and AA were determined. An ultra-performance liquid chromatography tandem mass spectrometry (HPLC-DAD/ESI-MS) method was developed for the determination of gallic acid (GAE), p-hydroxybenzoic acid (PHB), chlorogenic acid (CHL), vanillic acid (VAN), and caffeic acid (CAF). A principal component analysis (PCA) and a cluster analysis (CA) were used to analyze differences related to cultivar and variety. The TP, TF, TA, TT, and AA of samples sourced from the Shandong province of China were higher than those from the Jiangsu province. The PCA and CA results showed that phenolic compounds in cherry wines were closely related to cultivar and variety and that cultivar had more influence on the phenolic compounds of cherry wines than variety. PMID:25976793

  4. Characterisation of phenolic compounds in processed fibres from the juice industry.

    PubMed

    Delpino-Rius, Antoni; Eras, Jordi; Vilaró, Francisca; Cubero, Miguel Ángel; Balcells, Mercè; Canela-Garayoa, Ramon

    2015-04-01

    The content of phenolic compounds was determined in nine industrially processed fibres derived from the juice industry. Apple, peach, and pear as non-citrus fruit fibres were examined, as well as orange peel and flesh, tangerine peel and flesh, and lemon flesh as citrus fruit fibres, and carrot as vegetable fibre. The extractable phenolic profile of all fibres was obtained by UPLC-PDA-FLR-MS/MS. Forty phenolic compounds were identified and their concentrations determined. In addition, bound phenolic acids and proanthocyanidins were measured in solid residues in order to determine the phenolic compounds remaining. Also, to allow the comparison of the profiles and contents in the fresh fruit and fibres, we analysed extractable and bound phenolic compounds in lyophilized peel and pulp from fresh fruit. The profile and phenolic content of the fibres was similar to that of the fresh fruit, except for flavan-3-ols, which registered lower values.

  5. Gallic acid, a phenolic compound, exerts anti-angiogenic effects via the PTEN/AKT/HIF-1α/VEGF signaling pathway in ovarian cancer cells.

    PubMed

    He, Zhiping; Chen, Allen Y; Rojanasakul, Yon; Rankin, Gary O; Chen, Yi Charlie

    2016-01-01

    Gallic acid (GA), a polyphenol, is widely found in numerous fruits and vegetables, particularly in hickory nuts. In the present study, we found that gallic acid, a natural phenolic compound isolated from fruits and vegetables, had a more potent growth inhibitory effect on two ovarian cancer cell lines, OVCAR-3 and A2780/CP70, than the effect on a normal ovarian cell line, IOSE-364. These results demonstrated that GA selectively inhibits the growth of cancer cells. Gene expression was examined by ELISA and western blot analysis, and gene pathways were examined by luciferase assay. It was found that GA inhibited VEGF secretion and suppressed in vitro angiogenesis in a concentration-dependent manner. GA downregulated AKT phosphorylation as well as HIF-1α expression but promoted PTEN expression. The luciferase assay results suggest that the PTEN/AKT/HIF-1α pathway accounts for the inhibitory effect of GA on VEGF expression and in vitro angiogenesis. These findings provide strong support for the high potential of GA in the prevention and therapy of ovarian cancer.

  6. Gallic acid, a phenolic compound, exerts anti-angiogenic effects via the PTEN/AKT/HIF-1α/VEGF signaling pathway in ovarian cancer cells

    PubMed Central

    HE, ZHIPING; CHEN, ALLEN Y.; ROJANASAKUL, YON; RANKIN, GARY O.; CHEN, YI CHARLIE

    2016-01-01

    Gallic acid (GA), a polyphenol, is widely found in numerous fruits and vegetables, particularly in hickory nuts. In the present study, we found that gallic acid, a natural phenolic compound isolated from fruits and vegetables, had a more potent growth inhibitory effect on two ovarian cancer cell lines, OVCAR-3 and A2780/CP70, than the effect on a normal ovarian cell line, IOSE-364. These results demonstrated that GA selectively inhibits the growth of cancer cells. Gene expression was examined by ELISA and western blot analysis, and gene pathways were examined by luciferase assay. It was found that GA inhibited VEGF secretion and suppressed in vitro angiogenesis in a concentration-dependent manner. GA downregulated AKT phosphorylation as well as HIF-1α expression but promoted PTEN expression. The luciferase assay results suggest that the PTEN/AKT/HIF-1α pathway accounts for the inhibitory effect of GA on VEGF expression and in vitro angiogenesis. These findings provide strong support for the high potential of GA in the prevention and therapy of ovarian cancer. PMID:26530725

  7. Assessment of total (free and bound) phenolic compounds in spent coffee extracts.

    PubMed

    Monente, Carmen; Ludwig, Iziar A; Irigoyen, Angel; De Peña, María-Paz; Cid, Concepción

    2015-05-01

    Spent coffee is the main byproduct of the brewing process and a potential source of bioactive compounds, mainly phenolic acids easily extracted with water. Free and bound caffeoylquinic (3-CQA, 4-CQA, 5-CQA), dicaffeoylquinic (3,4-diCQA, 3,5-diCQA, 4,5-diCQA), caffeic, ferulic, p-coumaric, sinapic, and 4-hydroxybenzoic acids were measured by HPLC, after the application of three treatments (alkaline, acid, saline) to spent coffee extracts. Around 2-fold higher content of total phenolics has been estimated in comparison to free compounds. Phenolic compounds with one or more caffeic acid molecules were approximately 54% linked to macromolecules such as melanoidins, mainly by noncovalent interactions (up to 81% of bound phenolic compounds). The rest of the quantitated phenolic acids were mainly attached to other structures by covalent bonds (62-97% of total bound compounds). Alkaline hydrolysis and saline treatment were suitable to estimate total bound and ionically bound phenolic acids, respectively, whereas acid hydrolysis is an inadequate method to quantitate coffee phenolic acids.

  8. Determination of phenolic compounds and antioxidant activity in leaves from wild Rubus L. species.

    PubMed

    Oszmiański, Jan; Wojdyło, Aneta; Nowicka, Paulina; Teleszko, Mirosława; Cebulak, Tomasz; Wolanin, Mateusz

    2015-03-18

    Twenty-six different wild blackberry leaf samples were harvested from various localities throughout southeastern Poland. Leaf samples were assessed regarding their phenolic compound profiles and contents by LC/MS QTOF, and their antioxidant activity by ABTS and FRAP. Thirty-three phenolic compounds were detected (15 flavonols, 13 hydroxycinnamic acids, three ellagic acid derivatives and two flavones). Ellagic acid derivatives were the predominant compounds in the analyzed leaves, especially sanguiin H-6, ellagitannins, lambertianin C, and casuarinin. The content of phenolic compounds was significantly correlated with the antioxidant activity of the analyzed samples. The highest level of phenolic compounds was measured for R. perrobustus, R. wimmerianus, R. pedemontanus and R. grabowskii. The study showed that wild blackberry leaves can be considered a good source of antioxidant compounds. There is clear potential for the utilization of blackberry leaves as a food additive, medicinal source or herbal tea.

  9. Antibacterial Potential of Northeastern Portugal Wild Plant Extracts and Respective Phenolic Compounds

    PubMed Central

    Ferreira, Isabel C. F. R.; Barros, Lillian; Carvalho, Ana Maria; Soares, Graça; Henriques, Mariana

    2014-01-01

    The present work aims to assess the antibacterial potential of phenolic extracts, recovered from plants obtained on the North East of Portugal, and of their phenolic compounds (ellagic, caffeic, and gallic acids, quercetin, kaempferol, and rutin), against bacteria commonly found on skin infections. The disk diffusion and the susceptibility assays were used to identify the most active extracts and phenolic compounds. The effect of selected phenolic compounds on animal cells was assessed by determination of cellular metabolic activity. Gallic acid had a higher activity, against gram-positive (S. epidermidis and S. aureus) and gram-negative bacteria (K. pneumoniae) at lower concentrations, than the other compounds. The caffeic acid, also, showed good antibacterial activity against the 3 bacteria used. The gallic acid was effective against the 3 bacteria without causing harm to the animal cells. Gallic and caffeic acid showed a promising applicability as antibacterial agents for the treatment of infected wounds. PMID:24804249

  10. Principal component analysis of phenolic acid spectra

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phenolic acids are common plant metabolites that exhibit bioactive properties and have applications in functional food and animal feed formulations. The ultraviolet (UV) and infrared (IR) spectra of four closely related phenolic acid structures were evaluated by principal component analysis (PCA) to...

  11. New phenolic compounds from Kokuto, non-centrifuged cane sugar.

    PubMed

    Takara, Kensaku; Matsui, Daigo; Wada, Koji; Ichiba, Toshio; Chinen, Isao; Nakasone, Yoko

    2003-02-01

    Five new phenolic compounds, 4-(beta-D-glucopyranosyloxy)-3,5-dimethoxyphenyl-propanone (8), 3-[5-[(threo) 2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzofuranyl]-propanoic acid (12), 2-[4-(3-hydroxy-1-propenyl)-2,6-dimethoxyphenoxy]-3-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)propyl-beta-D-glucopyranoside (13), 4-[(erythro) 2,3-dihydro-3(hydroxymethyl)-5-(3-hydropropyl)-7-methoxy-2-benzofuranyl]-2,6-dimethoxyphenyl-beta-D-glucopyranoside (14), 9-O-beta-D-xylopyranoside of icariol A2 (15), and known phenolic compounds were isolated from Kokuto, non-centrifuged cane sugar (Saccharum officinarum L.). Their structures were determined by a spectral investigation.

  12. Phenolic compounds with IL-6 inhibitory activity from Aster yomena.

    PubMed

    Kim, A Ryun; Jin, Qinglong; Jin, Hong-Guang; Ko, Hae Ju; Woo, Eun-Rhan

    2014-07-01

    A new biflavonoid, named asteryomenin (1), as well as six known phenolic compounds, esculetin (2), 4-O-β-D-glucopyranoside-3-hydroxy methyl benzoate (3), caffeic acid (4), isoquercitrin (5), isorhamnetin-3-O-glucoside (6), and apigenin (7) were isolated from the aerial parts of Aster yomena. The structures of compounds (1-7) were identified based on 1D and 2D NMR, including (1)H-(1)H COSY, HSQC, HMBC and NOESY spectroscopic analyses. Compounds 2-7 were isolated from this plant for the first time. For these isolates, the inhibitory activity of IL-6 production in the TNF-α stimulated MG-63 cell was examined. Among these isolates, compounds 4 and 7 appeared to have potent inhibitory activity of IL-6 production in the TNF-α stimulated MG-63 cell, while compounds 1-3 and 5-6 showed moderate activity.

  13. Characterisation of phenolic compounds in wild fruits from Northeastern Portugal.

    PubMed

    Guimarães, Rafaela; Barros, Lillian; Dueñas, Montserrat; Carvalho, Ana Maria; Queiroz, Maria João R P; Santos-Buelga, Celestino; Ferreira, Isabel C F R

    2013-12-15

    This study aimed to analyse the phenolic composition of wild fruits of Arbutus unedo (strawberry-tree), Prunus spinosa (blackthorn), Rosa canina and Rosa micrantha (wild roses). Analyses were performed by HPLC-DAD-ESI/MS. P spinosa fruits presented the highest concentration in phenolic acids (29.78 mg/100 g dry weight), being 3-O-caffeoylquinic acid the most abundant one, and flavone/ols (57.48 mg/100 g), among which quercetin3-O-rutinoside (15.63 mg/100 g) was the majority compound. (+)-Catechin was the most abundant compound in A. unedo (13.51 mg/100 g) and R. canina (3.59 mg/100 g) fruits. A. unedo fruits presented the highest concentration in flavan-3-ols (36.30 mg/100 g). Cyanidin 3-O-glucoside was found in all the studied fruits, being the major anthocyanin in most of them, with the exception of P. spinosa samples, in which cyaniding 3-O-rutinoside and peonidin 3-O-rutinoside predominated; P. spinosa fruit presented the more complex anthocyanin profile among the analysed fruits and also the highest anthocyanin concentrations, which was coherent with its greater pigmentation. All in all, P. spinosa presented the highest levels of phenolic acids and flavonoids, including anthocyanins, flavonols and flavones, although no flavan-3-ols could be identified in its fruits. The present study represents a contribution to the chemical characterisation of phenolic compounds from wild fruits with acknowledged antioxidant activity and traditionally used for several folk medicinal applications.

  14. Characterisation of phenolic compounds in wild fruits from Northeastern Portugal.

    PubMed

    Guimarães, Rafaela; Barros, Lillian; Dueñas, Montserrat; Carvalho, Ana Maria; Queiroz, Maria João R P; Santos-Buelga, Celestino; Ferreira, Isabel C F R

    2013-12-15

    This study aimed to analyse the phenolic composition of wild fruits of Arbutus unedo (strawberry-tree), Prunus spinosa (blackthorn), Rosa canina and Rosa micrantha (wild roses). Analyses were performed by HPLC-DAD-ESI/MS. P spinosa fruits presented the highest concentration in phenolic acids (29.78 mg/100 g dry weight), being 3-O-caffeoylquinic acid the most abundant one, and flavone/ols (57.48 mg/100 g), among which quercetin3-O-rutinoside (15.63 mg/100 g) was the majority compound. (+)-Catechin was the most abundant compound in A. unedo (13.51 mg/100 g) and R. canina (3.59 mg/100 g) fruits. A. unedo fruits presented the highest concentration in flavan-3-ols (36.30 mg/100 g). Cyanidin 3-O-glucoside was found in all the studied fruits, being the major anthocyanin in most of them, with the exception of P. spinosa samples, in which cyaniding 3-O-rutinoside and peonidin 3-O-rutinoside predominated; P. spinosa fruit presented the more complex anthocyanin profile among the analysed fruits and also the highest anthocyanin concentrations, which was coherent with its greater pigmentation. All in all, P. spinosa presented the highest levels of phenolic acids and flavonoids, including anthocyanins, flavonols and flavones, although no flavan-3-ols could be identified in its fruits. The present study represents a contribution to the chemical characterisation of phenolic compounds from wild fruits with acknowledged antioxidant activity and traditionally used for several folk medicinal applications. PMID:23993541

  15. Analysis of phenolic compounds in six Norwegian plum cultivars (Prunus domestica L.).

    PubMed

    Slimestad, Rune; Vangdal, Eivind; Brede, Cato

    2009-12-01

    Six European plum cultivars ( Prunus domestica L.) grown in Norway have been studied with respect to phenolic composition. Neochlorogenic acid was found to be the most important phenolic acid in all cultivars. Together with other phenolic acids, this compound varied significantly in amount among the cultivars. Cyanidin 3-rutinoside was found to account for >60% of the total anthocyanin content. Minor amounts of flavonols (rutin and quercetin 3-glucoside) were detected in all cultivars. Total antioxidant capacity varied from 814 to 290 micromol of Trolox 100 g(-1) of fresh weight. Measurement of total phenolic content in terms of Prussian blue complex formation revealed a method failure of magnitude order compared to results obtained by HPLC. Comparison of the response factors of a range of phenolic compounds obtained upon analysis by the Prussian blue and Folin-Ciocalteu assays revealed that the latter method returned higher yields in terms of gallic acid (GAE).

  16. Green tea yogurt: major phenolic compounds and microbial growth.

    PubMed

    Amirdivani, Shabboo; Baba, Ahmad Salihin Hj

    2015-07-01

    The purpose of this study was to evaluate fermentation of milk in the presence of green tea (Camellia sinensis) with respect to changes in antioxidant activity, phenolic compounds and the growth of lactic acid bacteria. Pasteurized full fat cow's milk and starter culture were incubated at 41 °C in the presence of two different types of green tea extracts. The yogurts formed were refrigerated (4 °C) for further analysis. The total phenolic content was highest (p < 0.05) in air-dried green tea-yogurt (MGT) followed by steam-treated green tea (JGT) and plain yogurts. Four major compounds in MGTY and JGTY were detected. The highest concentration of major phenolic compounds in both samples was related to quercetin-rhamnosylgalactoside and quercetin-3-O-galactosyl-rhamnosyl-glucoside for MGTY and JGTY respectively during first 7 day of storage. Diphenyl picrylhydrazyl and ferric reducing antioxidant power methods showed highest antioxidant capacity in MGTY, JGTY and PY. Streptococcus thermophillus and Lactobacillus spp. were highest in MGTY followed by JGTY and PY. This paper evaluates the implementation of green tea yogurt as a new product with functional properties and valuable component to promote the growth of beneficial yogurt bacteria and prevention of oxidative stress by enhancing the antioxidant activity of yogurt. PMID:26139940

  17. Reducing the allergenic capacity of peanut extracts and liquid peanut butter by phenolic compounds.

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phenolic compounds are known to form soluble and insoluble complexes with proteins. The objective of this study was to determine if phenolics, such as, caffeic, chlorogenic, and ferulic acids form insoluble and irreversible complexes with major peanut allergens. We also tested whether such complexat...

  18. [Allelopathic effects of phenolic compounds of melon root exudates on Fusarium oxysporum f. sp. melonis].

    PubMed

    Yang, Rui-Xiu; Gao, Zeng-Gui; Yao, Yuan; Liu, Xian; Sun, Shu-Qing; Wang, Ying

    2014-08-01

    In this study, the phenolic compounds of melon root exudates were identified by HPLC and seven phenolic compounds including gallic acid, phthalic acid, syringic acid, salicylic acid, ferulic acid, benzoic acid and cinnamic acid were observed. The laboratory experiment showed that ferulic acid, benzoic acid and cinnamic acid of 0.1 and 0.25 mmol x L(-1) could significantly promote the germination of Fusarium oxysporum f. sp. melonis spore while salicylic acid inhibited the spore germination to some degree. Syringic acid and ferulic acid significantly promoted the mycelium growth at the late stage of incubation. The pot experiments demonstrated that cinnamic acid, benzoic acid and ferulic acid enhanced melon infection at concentrations of 0.5, 0.1 and 0.5 mmol x L(-1). PMID:25509089

  19. [Allelopathic effects of phenolic compounds of melon root exudates on Fusarium oxysporum f. sp. melonis].

    PubMed

    Yang, Rui-Xiu; Gao, Zeng-Gui; Yao, Yuan; Liu, Xian; Sun, Shu-Qing; Wang, Ying

    2014-08-01

    In this study, the phenolic compounds of melon root exudates were identified by HPLC and seven phenolic compounds including gallic acid, phthalic acid, syringic acid, salicylic acid, ferulic acid, benzoic acid and cinnamic acid were observed. The laboratory experiment showed that ferulic acid, benzoic acid and cinnamic acid of 0.1 and 0.25 mmol x L(-1) could significantly promote the germination of Fusarium oxysporum f. sp. melonis spore while salicylic acid inhibited the spore germination to some degree. Syringic acid and ferulic acid significantly promoted the mycelium growth at the late stage of incubation. The pot experiments demonstrated that cinnamic acid, benzoic acid and ferulic acid enhanced melon infection at concentrations of 0.5, 0.1 and 0.5 mmol x L(-1).

  20. Riboflavin Phototransformation on the Changes of Antioxidant Capacities in Phenolic Compounds.

    PubMed

    Song, Juhee; Seol, Nam Gyu; Kim, Mi-Ja; Lee, JaeHwan

    2016-08-01

    Eight phenolic compounds including: p-coumaric acid, vanillic acid, caffeic acid, chlorogenic acid, trolox, quercetin, curcumin, and resveratrol were treated with riboflavin (RF) photosensitization and in vitro antioxidant capacities of the mixtures were determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2' azino bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), and ferric reducing antioxidant power (FRAP) assays. Mixtures containing p-coumaric acid and vanillic acid under RF photosensitization showed increases in ferric ion reducing ability and radical scavenging activity of DPPH, whereas mixtures of other compounds had decreases in both radical scavenging ability and ferric reducing antioxidant power. Hydroxycoumaric acid and conjugated hydroxycoumaric and coumaric acids were tentatively identified from RF photosensitized p-coumaric acid, whereas dimmers of vanillic acid were tentatively identified from RF photosensitized vanillic acid. RF photosensitization may be a useful method to enhance antioxidant properties like ferric ion reducing abilities of some selected phenolic compounds.

  1. Riboflavin Phototransformation on the Changes of Antioxidant Capacities in Phenolic Compounds.

    PubMed

    Song, Juhee; Seol, Nam Gyu; Kim, Mi-Ja; Lee, JaeHwan

    2016-08-01

    Eight phenolic compounds including: p-coumaric acid, vanillic acid, caffeic acid, chlorogenic acid, trolox, quercetin, curcumin, and resveratrol were treated with riboflavin (RF) photosensitization and in vitro antioxidant capacities of the mixtures were determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2' azino bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), and ferric reducing antioxidant power (FRAP) assays. Mixtures containing p-coumaric acid and vanillic acid under RF photosensitization showed increases in ferric ion reducing ability and radical scavenging activity of DPPH, whereas mixtures of other compounds had decreases in both radical scavenging ability and ferric reducing antioxidant power. Hydroxycoumaric acid and conjugated hydroxycoumaric and coumaric acids were tentatively identified from RF photosensitized p-coumaric acid, whereas dimmers of vanillic acid were tentatively identified from RF photosensitized vanillic acid. RF photosensitization may be a useful method to enhance antioxidant properties like ferric ion reducing abilities of some selected phenolic compounds. PMID:27387389

  2. The Profile and Bioaccessibility of Phenolic Compounds in Cereals Influenced by Improved Extrusion Cooking Treatment.

    PubMed

    Zeng, Zicong; Liu, Chengmei; Luo, Shunjing; Chen, Jun; Gong, Ersheng

    2016-01-01

    The aim of this study was to investigate the effect of Improved Extrusion Cooking Treatment (IECT) on the phenolics and its bioaccessibility in cereals, represented by brown rice, wheat, and oat. Data showed that total phenolic content and total antioxidant activity in free form were significantly decreased, while the bound form was increased after IECT. After IECT, the total free phenolic acids of brown rice and wheat were significantly decreased by 5.88% and 45.66%, respectively, while the total bound phenolic acids of brown rice, wheat, and oat were significantly increased by 6.45%, 8.78%, and 9.10%, respectively. Brown rice provided the most bioaccessible phenolics and antioxidant compounds, followed by oat and wheat. IECT significantly decreased the bioaccessible phenolics of brown rice and oat by 31.09% and 30.95%, while it had minimal effect on the bioaccessible phenolics of wheat. These results showed that IECT greatly affected the phenolics and its bioaccessibiltiy of cereals, with the effect depending on cereal matrix and the sensitivity of free and bound phenolics. Furthermore, bioaccessible phenolic acids of raw and processed cereals were considerably low, and it slightly contributed to the bioaccessible phenolics. PMID:27513581

  3. The Profile and Bioaccessibility of Phenolic Compounds in Cereals Influenced by Improved Extrusion Cooking Treatment

    PubMed Central

    Zeng, Zicong; Liu, Chengmei; Luo, Shunjing; Chen, Jun; Gong, Ersheng

    2016-01-01

    The aim of this study was to investigate the effect of Improved Extrusion Cooking Treatment (IECT) on the phenolics and its bioaccessibility in cereals, represented by brown rice, wheat, and oat. Data showed that total phenolic content and total antioxidant activity in free form were significantly decreased, while the bound form was increased after IECT. After IECT, the total free phenolic acids of brown rice and wheat were significantly decreased by 5.88% and 45.66%, respectively, while the total bound phenolic acids of brown rice, wheat, and oat were significantly increased by 6.45%, 8.78%, and 9.10%, respectively. Brown rice provided the most bioaccessible phenolics and antioxidant compounds, followed by oat and wheat. IECT significantly decreased the bioaccessible phenolics of brown rice and oat by 31.09% and 30.95%, while it had minimal effect on the bioaccessible phenolics of wheat. These results showed that IECT greatly affected the phenolics and its bioaccessibiltiy of cereals, with the effect depending on cereal matrix and the sensitivity of free and bound phenolics. Furthermore, bioaccessible phenolic acids of raw and processed cereals were considerably low, and it slightly contributed to the bioaccessible phenolics. PMID:27513581

  4. The impact of drying techniques on phenolic compound, total phenolic content and antioxidant capacity of oat flour tarhana.

    PubMed

    Değirmencioğlu, Nurcan; Gürbüz, Ozan; Herken, Emine Nur; Yıldız, Aysun Yurdunuseven

    2016-03-01

    In this study, the changes in phenolic composition, total phenolic content, and antioxidant capacity of tarhanas supplemented with oat flour (OF) at the levels of 20-100% (w/w) after three drying treatments (sun-, oven-, and microwave drying) were investigated. A total of seventeen phenolic standards have been screened in tarhanas, and the most abundant flavonol and phenolic acid compounds were kaempferol (23.62mg/g) and 3-hydroxy-4-metoxy cinnamic acid (9.60mg/g). The total phenolic content amount gradually increased with the addition of OF to tarhana, but decidedly higher total phenolic content was found in samples oven dried at 55°C as compared with other methods. The microwave- and oven dried tarhana samples showed higher TEACDPPH and TEACABTS values than those dried with the other methods, respectively, in higher OF amounts. Consequently, oven- and microwave-drying can be recommended to retain the highest for phenolic compounds as well as maximal antioxidant capacity in OF supplemented tarhana samples. PMID:26471596

  5. Development of a phenol-enriched olive oil with both its own phenolic compounds and complementary phenols from thyme.

    PubMed

    Rubió, Laura; Motilva, Maria-José; Macià, Alba; Ramo, Tomás; Romero, Maria-Paz

    2012-03-28

    Besides affecting the oil's sensorial characteristics, the presence of herbs and spices has an impact on the nutritional value of the flavored oils. The aim of the study was to develop a new product based on the phenol-enrichment of a virgin olive oil with both its own phenolic compounds (secoiridoid derivatives) plus additional complementary phenols from thyme (flavonoids). We studied the effect of the addition of phenolic extracts (olive cake and thyme) on phenolic composition, oxidative stability, antioxidant activity, and bitter sensory attribute of olive oils. Results showed that flavonoids from thyme appeared to have higher transference ratios (average 89.7%) from the phenolic extract to oil, whereas secoiridoids from olive presented lower transference ratios (average 35.3%). The bitter sensory attribute of the phenol-enriched oils diminished with an increase of the concentration of phenols from thyme, which might denote an improvement in the consumer acceptance.

  6. Development of a phenol-enriched olive oil with both its own phenolic compounds and complementary phenols from thyme.

    PubMed

    Rubió, Laura; Motilva, Maria-José; Macià, Alba; Ramo, Tomás; Romero, Maria-Paz

    2012-03-28

    Besides affecting the oil's sensorial characteristics, the presence of herbs and spices has an impact on the nutritional value of the flavored oils. The aim of the study was to develop a new product based on the phenol-enrichment of a virgin olive oil with both its own phenolic compounds (secoiridoid derivatives) plus additional complementary phenols from thyme (flavonoids). We studied the effect of the addition of phenolic extracts (olive cake and thyme) on phenolic composition, oxidative stability, antioxidant activity, and bitter sensory attribute of olive oils. Results showed that flavonoids from thyme appeared to have higher transference ratios (average 89.7%) from the phenolic extract to oil, whereas secoiridoids from olive presented lower transference ratios (average 35.3%). The bitter sensory attribute of the phenol-enriched oils diminished with an increase of the concentration of phenols from thyme, which might denote an improvement in the consumer acceptance. PMID:22380740

  7. Phenolic acids as bioindicators of fly ash deposit revegetation.

    PubMed

    Djurdjević, L; Mitrović, M; Pavlović, P; Gajić, G; Kostić, O

    2006-05-01

    The floristic composition, the abundance, and the cover of pioneer plant species of spontaneously formed plant communities and the content of total phenolics and phenolic acids, as humus constituents, of an ash deposit after 7 years of recultivation were studied. The restoration of both the soil and the vegetation on the ash deposits of the "Nikola Tesla-A" thermoelectric power plant in Obrenovac (Serbia) is an extremely slow process. Unfavorable physical and chemical characteristics, the toxicity of fly ash, and extreme microclimatic conditions prevented the development of compact plant cover. The abundance and cover of plants increased from the central part of the deposit towards its edges (ranging from 1-80%). Festuca rubra L., Crepis setosa Hall., Erigeron canadensis L., Cirsium arvense (L.) Scop., Calamagrostis epigeios (L.) Roth., and Tamarix gallica L. were the most abundant species, thus giving the highest cover. Humus generated during the decomposition process of plant remains represents a completely new product absent in the ash as the starting material. The amount of total phenolics and phenolic acids (38.07-185.16 microg/g of total phenolics and 4.12-27.28 microg/g of phenolic acids) in fly ash increased from the center of the deposit towards its edges in correlation with the increase in plant abundance and cover. Ash samples contained high amounts of ferulic, vanillic, and p-coumaric acid, while the content of both p-hydroxybenzoic and syringic acid was relatively low. The presence of phenolic acids indicates the ongoing process of humus formation in the ash, in which the most abundant pioneer plants of spontaneously formed plant communities play the main role. Phenolic compounds can serve as reliable bioindicators in an assessment of the success of the recultivation process of thermoelectric power plants' ash deposits.

  8. Phenolic acids as bioindicators of fly ash deposit revegetation.

    PubMed

    Djurdjević, L; Mitrović, M; Pavlović, P; Gajić, G; Kostić, O

    2006-05-01

    The floristic composition, the abundance, and the cover of pioneer plant species of spontaneously formed plant communities and the content of total phenolics and phenolic acids, as humus constituents, of an ash deposit after 7 years of recultivation were studied. The restoration of both the soil and the vegetation on the ash deposits of the "Nikola Tesla-A" thermoelectric power plant in Obrenovac (Serbia) is an extremely slow process. Unfavorable physical and chemical characteristics, the toxicity of fly ash, and extreme microclimatic conditions prevented the development of compact plant cover. The abundance and cover of plants increased from the central part of the deposit towards its edges (ranging from 1-80%). Festuca rubra L., Crepis setosa Hall., Erigeron canadensis L., Cirsium arvense (L.) Scop., Calamagrostis epigeios (L.) Roth., and Tamarix gallica L. were the most abundant species, thus giving the highest cover. Humus generated during the decomposition process of plant remains represents a completely new product absent in the ash as the starting material. The amount of total phenolics and phenolic acids (38.07-185.16 microg/g of total phenolics and 4.12-27.28 microg/g of phenolic acids) in fly ash increased from the center of the deposit towards its edges in correlation with the increase in plant abundance and cover. Ash samples contained high amounts of ferulic, vanillic, and p-coumaric acid, while the content of both p-hydroxybenzoic and syringic acid was relatively low. The presence of phenolic acids indicates the ongoing process of humus formation in the ash, in which the most abundant pioneer plants of spontaneously formed plant communities play the main role. Phenolic compounds can serve as reliable bioindicators in an assessment of the success of the recultivation process of thermoelectric power plants' ash deposits. PMID:16418890

  9. Spectroscopic analysis of phenolic compounds for food and feed formulations

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phenolic compounds exhibit several bioactive properties including anti-oxidant, anti-microbial, and anti-fungal characteristics with potential applications as additives in functional food and feed formulations. Phenolic compounds occur in plants as secondary metabolites and may be recovered as a co-...

  10. Comparative evaluation of volatiles, phenolics, sugars, organic acids and antioxidant properties of Sel-42 and Tainung papaya varieties.

    PubMed

    Kelebek, Hasim; Selli, Serkan; Gubbuk, Hamide; Gunes, Esma

    2015-04-15

    The present study was designed to determine the phenolic compounds, organic acids, sugars, aroma profiles and antioxidant properties of Sel-42 and Tainung papayas grown in Turkey. High-performance liquid chromatography/electrospray ionisation tandem mass spectrometry (HPLC-ESI-MS/MS) method was used for the phenolic compounds analysis. Twelve phenolic compounds were identified and quantified in the samples. The total phenolic content of Sel-42 was clearly higher than that of Tainung. Protocatechuic acid-hexoside, gallic acid-deoxyhexoside, ferulic acid and chlorogenic acids were the most abundant phenolics in both cultivars. Aroma composition of papaya was analysed by gas chromatography-mass spectrometry (GC-MS). A total of 46 and 42 aroma compounds, including esters, alcohols, terpenes, lactones, acids, carbonyl compounds, and volatile phenols were identified in the Sel-42 and Tainung, respectively. The significant linear correlation was confirmed between the values for the total phenolic content and antioxidant activity of papaya extracts.

  11. Influence of various phenolic compounds on phenol hydroxylase activity of a Trichosporon cutaneum strain.

    PubMed

    Gerginova, Maria; Manasiev, Jordan; Shivarova, Nedka; Alexieva, Zlatka

    2007-01-01

    The phenol-degrading strain Trichosporon cutaneum R57 utilizes various aromatic and aliphatic compounds as a sole carbon and energy source. The intracellular activities of phenol hydroxylase [EC 1.14.13.7] of a Trichosporon cutaneum R57 strain grown on phenol (0.5 g/l) were measured. Different toxic phenol derivatives (cresols, nitrophenols and hydroxyphenols) were used as substrates in the reaction mixture for determination of the enzyme activity. The data obtained showed that the investigated enzyme was capable to hydroxylate all applied aromatic substrates. The measured activities of phenol hydroxylase varied significantly depending on the aromatic compounds used as substrates. The rate of phenol hydroxylase activity with phenol as a substrate (1.0 U/mg total cell protein) was accepted as 100%.

  12. Olive oil phenolic compounds affect the release of aroma compounds.

    PubMed

    Genovese, Alessandro; Caporaso, Nicola; Villani, Veronica; Paduano, Antonello; Sacchi, Raffaele

    2015-08-15

    Twelve aroma compounds were monitored and quantified by dynamic headspace analysis after their addition in refined olive oil model systems with extra virgin olive oil (EVOO) biophenols to simulate EVOO aroma. The influence of polyphenols on aroma release was studied under simulated mouth conditions by using human saliva, and SPME-GC/MS analysis. While few differences were observed in orthonasal assay (without saliva), interesting results were obtained for retronasal aroma. Biophenols caused generally the lowest headspace release of almost all volatile compounds. However, only ethyl esters and linalool concentrations were significantly lower in retronasal than orthonasal assay. Saliva also caused higher concentration of hexanal, probably due to hydroperoxide lyase (HPL) action on linoleyl hydroperoxides. Epicatechin was compared to EVOO phenolics and the behaviour was dramatically different, likely to be due to salivary protein-tannin binding interactions, which influenced aroma headspace release. These results were also confirmed using two extra virgin olive oils. PMID:25794752

  13. Metabolism of phenolic compounds by Lactobacillus spp. during fermentation of cherry juice and broccoli puree.

    PubMed

    Filannino, Pasquale; Bai, Yunpeng; Di Cagno, Raffaela; Gobbetti, Marco; Gänzle, Michael G

    2015-04-01

    This study aimed to investigate the metabolism of phenolic acids and flavonoids during lactic acid fermentation of cherry juice and broccoli puree for potential food and pharmaceutical purposes. When fermenting cherry juice and broccoli puree, Lactobacillus spp. exhibited strain-specific metabolism of phenolic acid derivatives. The metabolism of protocatechuic, caffeic and p-coumaric acids through phenolic acid decarboxylases and reductases differed between mMRS and cherry juice and broccoli puree. The synthesis of reduced compounds was the highest during food fermentations and the substrate seemed to modulate the metabolism of phenolic compounds. The reduction of phenolic acids involves a hydrogen donor and the re-oxidation of the reduced co-factor NADH, which may provide a metabolic advantage through NAD(+) regeneration. Quinic acid reduction may replace fructose and pyruvate as hydrogen acceptors, and it may provide an energetic advantage to heterofermentative bacteria when growing in broccoli puree lacking of fructose. This study demonstrated that phenolics metabolism may confer a selective advantage for lactobacilli in vegetable and fruit fermentation, and the metabolic routes are strongly dependent on the intrinsic factors of substrate. Fermented cherry juice and broccoli puree, due to the selected bacterial bioconversion pathways, are enriched in phenolic derivative with high human bioavailability and biological activity.

  14. Inhibition of enzymatic cellulolysis by phenolic compounds.

    PubMed

    Tejirian, Ani; Xu, Feng

    2011-03-01

    Phenolics derived from lignin and other plant components can pose significant inhibition on enzymatic conversion of cellulosic biomass materials to useful chemicals. Understanding the mechanism of such inhibition is of importance for the development of viable biomass conversion technologies. In native plant cell wall, most of the phenolics and derivatives are found in polymeric lignin. When biomass feedstocks are pretreated (prior to enzymatic hydrolysis), simple or oligomeric phenolics and derivatives are often generated from lignin modification/degradation, which can inhibit biomass-converting enzymes. To further understand how such phenolic substances may affect cellulase reaction, we carried out a comparative study on a series of simple and oligomeric phenolics representing or mimicking the composition of lignin or its degradation products. Consistent to previous studies, we observed that oligomeric phenolics could exert more inhibition on enzymatic cellulolysis than simple phenolics. Oligomeric phenolics could inactivate cellulases by reversibly complexing them. Simple and oligomeric phenolics could also inhibit enzymatic cellulolysis by adsorbing onto cellulose. Individual cellulases showed different susceptibility toward these inhibitions. Polyethylene glycol and tannase could respectively bind and degrade the studied oligomeric phenolics, and by doing so mitigate the oligomeric phenolic's inhibition on cellulolysis. PMID:22112906

  15. Therapeutic Potential of Dietary Phenolic Acids

    PubMed Central

    Saibabu, Venkata; Fatima, Zeeshan; Khan, Luqman Ahmad; Hameed, Saif

    2015-01-01

    Although modern lifestyle has eased the quality of human life, this lifestyle's related patterns have imparted negative effects on health to acquire multiple diseases. Many synthetic drugs are invented during the last millennium but most if not all of them possess several side effects and proved to be costly. Convincing evidences have established the premise that the phytotherapeutic potential of natural compounds and need of search for novel drugs from natural sources are of high priority. Phenolic acids (PAs) are a class of secondary metabolites spread throughout the plant kingdom and generally involved in plethora of cellular processes involved in plant growth and reproduction and also produced as defense mechanism to sustain various environmental stresses. Extensive research on PAs strongly suggests that consumption of these compounds hold promise to offer protection against various ailments in humans. This paper focuses on the naturally derived PAs and summarizes the action mechanisms of these compounds during disease conditions. Based on the available information in the literature, it is suggested that use of PAs as drugs is very promising; however more research and clinical trials are necessary before these bioactive molecules can be made for treatment. Finally this review provides greater awareness of the promise that natural PAs hold for use in the disease prevention and therapy. PMID:26442119

  16. Effects of location within the tree canopy on carbohydrates, organic acids, amino acids and phenolic compounds in the fruit peel and flesh from three apple (Malus × domestica) cultivars

    PubMed Central

    Feng, Fengjuan; Li, Mingjun; Ma, Fengwang; Cheng, Lailiang

    2014-01-01

    Fruits from three cultivars of apple (Malus × domestica Borkh.)—‘McIntosh’, ‘Gala’ and ‘Mutsu’—were harvested from the exterior and interior of the tree canopy. Peel and flesh tissues were sampled separately to determine how the position of the fruit on the tree might affect the levels of the primary and secondary metabolites in the fruit. Fruit from the outer-canopy had a higher fresh weight and a higher soluble solids content compared with inner-canopy fruit. Both the flesh and peel of the outer-canopy fruit had higher concentrations of soluble sugars and sugar alcohols, but lower starch concentrations than the inner-canopy fruit. Canopy position did not significantly affect malic acid concentrations, except in the peel of ‘McIntosh’ and the flesh of ‘Mutsu’. Although levels of ascorbic and succinic acids were higher in the peel of the outer-canopy fruit, the responses of other organic acids to canopy position depended on tissue type and cultivar. Except for histidine, lysine, threonine and glycine, most amino acids accumulated at higher concentrations in the inner-canopy fruit. By contrast, levels of phenolic compounds from both the peel and flesh were significantly higher in the outer-canopy fruit. The significant effects of location within the canopy on both primary metabolites and secondary metabolites demonstrate the importance of light exposure on apple fruit quality. PMID:26504536

  17. European marketable grain legume seeds: Further insight into phenolic compounds profiles.

    PubMed

    Magalhães, Sara C Q; Taveira, Marcos; Cabrita, Ana R J; Fonseca, António J M; Valentão, Patrícia; Andrade, Paula B

    2017-01-15

    Twenty-nine mature raw varieties of grain legume seeds (chickpeas, field peas, faba beans, common vetch and lupins) produced in Europe were investigated for their phenolic profile by means of high performance liquid chromatography coupled to diode array detection (HPLC-DAD). To the best of our knowledge, this study reported for the first time the phenolic composition of mature raw seeds of chickpea type Desi, field pea and common vetch. Phenolic acids were predominant compounds in chickpeas, field peas and common vetch compared to flavonoids, whereas the opposite was observed for lupin seeds. Yellow lupins presented the highest levels of total phenolic compounds followed by narrow-leafed lupins (in average 960 and 679mg/kg, dry basis, respectively), whereas Kabuli chickpeas got the lowest ones (in average 47mg/kg, dry basis). Principal component analysis revealed that flavones and total levels of phenolic compounds were responsible for nearly 51% of total data variability. PMID:27542465

  18. European marketable grain legume seeds: Further insight into phenolic compounds profiles.

    PubMed

    Magalhães, Sara C Q; Taveira, Marcos; Cabrita, Ana R J; Fonseca, António J M; Valentão, Patrícia; Andrade, Paula B

    2017-01-15

    Twenty-nine mature raw varieties of grain legume seeds (chickpeas, field peas, faba beans, common vetch and lupins) produced in Europe were investigated for their phenolic profile by means of high performance liquid chromatography coupled to diode array detection (HPLC-DAD). To the best of our knowledge, this study reported for the first time the phenolic composition of mature raw seeds of chickpea type Desi, field pea and common vetch. Phenolic acids were predominant compounds in chickpeas, field peas and common vetch compared to flavonoids, whereas the opposite was observed for lupin seeds. Yellow lupins presented the highest levels of total phenolic compounds followed by narrow-leafed lupins (in average 960 and 679mg/kg, dry basis, respectively), whereas Kabuli chickpeas got the lowest ones (in average 47mg/kg, dry basis). Principal component analysis revealed that flavones and total levels of phenolic compounds were responsible for nearly 51% of total data variability.

  19. Phenolic compounds and flavonoids as plant growth regulators from fruit and leaf of Vitex rotundifolia.

    PubMed

    Yoshioka, Takeo; Inokuchi, Tomohisa; Fujioka, Shozo; Kimura, Yasuo

    2004-01-01

    Five phenolic compounds, 4-hydroxybenzoic acid methyl ester (1), vanillic acid methyl ester (2), 4-hydroxy benzaldehyde (3), 4-hydroxybenzoic acid (4) and ferulic acid (5), and four flavonoids, 5,5'-dihydroxy-4',6,7-trimethoxyflavanone (6), luteolin (7), vitexicarpin (8) and artemetin (9), were isolated from fruits and leaves of Vitex rotundifolia L. The biological activities of these nine compounds have been examined using a bioassay with lettuce seedlings.

  20. Phenolic acids as bioindicators of fly ash deposit revegetation

    SciTech Connect

    L. Djurdjevic; M. Mitrovic; P. Pavlovic; G. Gajic; O. Kostic

    2006-05-15

    The floristic composition, the abundance, and the cover of pioneer plant species of spontaneously formed plant communities and the content of total phenolics and phenolic acids, as humus constituents, of an ash deposit after 7 years of recultivation were studied. The restoration of both the soil and the vegetation on the ash deposits of the 'Nikola Tesla-A' thermoelectric power plant in Obrenovac (Serbia) is an extremely slow process. Unfavorable physical and chemical characteristics, the toxicity of fly ash, and extreme microclimatic conditions prevented the development of compact plant cover. The abundance and cover of plants increased from the central part of the deposit towards its edges. Festuca rubra L., Crepis setosa Hall., Erigeron canadensis L., Cirsium arvense (L.) Scop., Calamagrostis epigeios (L.) Roth., and Tamarix gallica L. were the most abundant species, thus giving the highest cover. Humus generated during the decomposition process of plant remains represents a completely new product absent in the ash as the starting material. The amount of total phenolics and phenolic acids in fly ash increased from the center of the deposit towards its edges in correlation with the increase in plant abundance and cover. The presence of phenolic acids indicates the ongoing process of humus formation in the ash, in which the most abundant pioneer plants of spontaneously formed plant communities play the main role. Phenolic compounds can serve as reliable bioindicators in an assessment of the success of the recultivation process of thermoelectric power plants' ash deposits.

  1. Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water.

    PubMed

    Xu, G H; Chen, J C; Liu, D H; Zhang, Y H; Jiang, P; Ye, X Q

    2008-01-01

    Some dried citrus peels, more familiar as chenpi in China, have been widely used in traditional Chinese medicines from ancient times. This paper reports the efficiency of infusion cooking on extracting minerals and phenolic compounds (flavanone glycosides [FGs], polymethoxylated flavones [PMFs], and phenolic acids), and also antioxidant activity of hot water extract of citrus peels. Peels of 2 citrus varieties, namely, Satsuma mandarin (C. unshiu Marc.) and Ponkan (C. poonensis Hort. ex Tanaka), which belong to C. reticulata, were selected. As a result, hot water extraction was efficient in extracting phenolic acids and some minerals. As for citrus flavonoids, narirutin, nobiletin, and tangeretin were easier to extract than hesperidin. The result of antioxidant capacity assays indicated that for citrus peels, hot water extract had almost the same capacity as the methanol extract. We suggested that Ponkan was more suitable as the source of chenpi, since its hot water extract had much higher content of phenolic acids, FGs and PMFs, and higher antioxidant capacity than those of Satsuma mandarin. Generally, to raise the extraction temperature or to prolong the time could not yield higher content of phenolic compounds and stronger antioxidant capacity, though the content of minerals increased to some extent. Furthermore, a 2nd-time extraction seemed necessary since considerable minerals and phenolic compounds could be obtained by doing so. Finally, we suggested that 2 times extraction at 100 degrees C for 30 min was proper to extract the minerals and phenolic compounds in chenpi. PMID:18211343

  2. Influence of microwaves treatment of rapeseed on phenolic compounds and canolol content.

    PubMed

    Yang, Mei; Zheng, Chang; Zhou, Qi; Liu, Changsheng; Li, Wenlin; Huang, Fenghong

    2014-02-26

    Rapeseeds were treated with microwaves under 800 W for 0, 1, 2, 3, 4, 5, 6, 7, and 8 min at a frequency of 2450 MHz, and oil was extracted with a press to investigate the influence on phenolic compounds, including sinapine, the main free phenolic acids, and canolol content in the rapeseeds and oil from them. The results indicated that sinapine and sinapic acid was the main phenolic compound and free phenolic acid in the rapeseed, respectively, and canolol was the main phenolic compound in the oil from rapeseed by cold press. Microwave treatment significantly influenced phenolic compounds content in the rapeseeds and oil from them. The sinapine, sinapic acid, and canolol content in rapeseed first increased and then decreased depending on the period of microwave radiation (p < 0.05). The canolol content of 7 min microwave pretreatment rapeseed increased to the maximum and was approximately six times greater than that of the unroasted rapeseed. The amount of canolol formed was significantly correlated with the content of sinapic acid and sinapine (for sinapic acid, r = -0.950, p < 0.001, for sinapine, r = -0.828, p < 0.05) and also the loss of sinapic acid and sinapine (for sinapic acid, r = 0.997, p < 0.001, for sinapine, r = 0.952, p < 0.05) during roasting. There were differences in the transfer rate of difference phenolic compounds to the oil extracted by press. Almost all of the sinapine remained in the cold-pressed cake and only 1.4-2.7% of the sinapic acid, whereas approximately 56-83% of the canolol was transferred to the oil. The transfer ratio of canolol significantly increased with microwave radiation time (p < 0.001). Microwave pretreatment of rapeseed benefited improving the oxidative stability of oil.

  3. Phenolic compounds: their journey after intake.

    PubMed

    Velderrain-Rodríguez, G R; Palafox-Carlos, H; Wall-Medrano, A; Ayala-Zavala, J F; Chen, C-Y O; Robles-Sánchez, M; Astiazaran-García, H; Alvarez-Parrilla, E; González-Aguilar, G A

    2014-02-01

    Plant foods are rich in phenolic compounds (PCs) that display multifaceted bioactions in health promotion and disease prevention. To exert their bioactivity, they must be delivered to and absorbed in the gastrointestinal (GI) tract, transported in circulation, and reach the target tissues. During the journey from ingestion to target tissues and final excretion, PCs are subjected to modifications by many factors during their absorption, deposition, metabolism and excretion (ADME) and consequently their bioefficacy may be modified. Consistent with all nutrients in foods, PCs must first be released from the food matrix through mechanical, chemical, and enzymatic forces to facilitate absorption along the GI tract, particularly in the upper small intestine section. Further, glycosylation of PCs directs the route of their absorption with glycones being transported through active transportation and aglycones through passive diffusion. After enteral absorption, the majority of PCs are extensively transformed by the detoxification system in enterocytes and liver for excretion in bile, feces, and urine. The journey of PCs from consumption to excretion appears to be comparable to many synthetic medications, but with some dissimilarities in their fate and bioactivity after phase I and II metabolism. The overall bioavailability of PCs is determined mainly by chemical characteristics, bioaccessibility, and ADME. In this review, factors accounting for variation in PCs bioavailability are discussed because this information is crucial for validation of the health benefits of PCs and their mechanism of action.

  4. Phenolic Compounds and Their Fates In Tropical Lepidopteran Larvae: Modifications In Alkaline Conditions.

    PubMed

    Vihakas, Matti; Gómez, Isrrael; Karonen, Maarit; Tähtinen, Petri; Sääksjärvi, Ilari; Salminen, Juha-Pekka

    2015-09-01

    Lepidopteran larvae encounter a variety of phenolic compounds while consuming their host plants. Some phenolics may oxidize under alkaline conditions prevailing in the larval guts, and the oxidation products may cause oxidative stress to the larvae. In this study, we aimed to find new ways to predict how phenolic compounds may be modified in the guts of herbivorous larvae. To do so, we studied the ease of oxidation of phenolic compounds from 12 tropical tree species. The leaf extracts were incubated in vitro in alkaline conditions, and the loss of total phenolics during incubation was used to estimate the oxidizability of extracts. The phenolic profiles of the leaf extracts before and after incubation were compared, revealing that some phenolic compounds were depleted during incubation. The leaves of the 12 tree species were each fed to 12 species of lepidopteran larvae that naturally feed on these trees. The phenolic profiles of larval frass were compared to those of in vitro incubated leaf extracts. These comparisons showed that the phenolic profiles of alkali-treated samples and frass samples were similar in many cases. This suggested that certain phenolics, such as ellagitannins, proanthocyanidins, and galloylquinic acid derivatives were modified by the alkaline pH of the larval gut. In other cases, the chromatographic profiles of frass and in vitro incubated leaf extracts were not similar, and new modifications of phenolics were detected in the frass. We conclude that the actual fates of phenolics in vivo are often more complicated than can be predicted by a simple in vitro method. PMID:26364295

  5. Phenolic Compounds and Their Fates In Tropical Lepidopteran Larvae: Modifications In Alkaline Conditions.

    PubMed

    Vihakas, Matti; Gómez, Isrrael; Karonen, Maarit; Tähtinen, Petri; Sääksjärvi, Ilari; Salminen, Juha-Pekka

    2015-09-01

    Lepidopteran larvae encounter a variety of phenolic compounds while consuming their host plants. Some phenolics may oxidize under alkaline conditions prevailing in the larval guts, and the oxidation products may cause oxidative stress to the larvae. In this study, we aimed to find new ways to predict how phenolic compounds may be modified in the guts of herbivorous larvae. To do so, we studied the ease of oxidation of phenolic compounds from 12 tropical tree species. The leaf extracts were incubated in vitro in alkaline conditions, and the loss of total phenolics during incubation was used to estimate the oxidizability of extracts. The phenolic profiles of the leaf extracts before and after incubation were compared, revealing that some phenolic compounds were depleted during incubation. The leaves of the 12 tree species were each fed to 12 species of lepidopteran larvae that naturally feed on these trees. The phenolic profiles of larval frass were compared to those of in vitro incubated leaf extracts. These comparisons showed that the phenolic profiles of alkali-treated samples and frass samples were similar in many cases. This suggested that certain phenolics, such as ellagitannins, proanthocyanidins, and galloylquinic acid derivatives were modified by the alkaline pH of the larval gut. In other cases, the chromatographic profiles of frass and in vitro incubated leaf extracts were not similar, and new modifications of phenolics were detected in the frass. We conclude that the actual fates of phenolics in vivo are often more complicated than can be predicted by a simple in vitro method.

  6. Phenolic acid esterases, coding sequences and methods

    DOEpatents

    Blum, David L.; Kataeva, Irina; Li, Xin-Liang; Ljungdahl, Lars G.

    2002-01-01

    Described herein are four phenolic acid esterases, three of which correspond to domains of previously unknown function within bacterial xylanases, from XynY and XynZ of Clostridium thermocellum and from a xylanase of Ruminococcus. The fourth specifically exemplified xylanase is a protein encoded within the genome of Orpinomyces PC-2. The amino acids of these polypeptides and nucleotide sequences encoding them are provided. Recombinant host cells, expression vectors and methods for the recombinant production of phenolic acid esterases are also provided.

  7. Two new phenolic compounds from the leaves of Alnus sibirica Fisch. ex Turcz.

    PubMed

    Kim, Manh Heun; Park, Kwan Hee; Kim, So Ra; Park, Kwang Jun; Oh, Myeong Hwan; Heo, Jun Hyeok; Yoon, Ki Hoon; Yin, Jun; Yoon, Kyu Hyung; Lee, Min Won

    2016-01-01

    Two new phenolic compounds, 4-O-glucopyranosyl-5-O-caffeoylshikimic acid (1) and 2,3-digalloyl oregonin (2), were isolated along with eight known phenolic compounds (3-10) from an 80% acetone extract of Alnus sibirica leaves. The chemical structures of these compounds were elucidated using 1D/2D nuclear magnetic resonance and high resolution-MS. The anti-oxidative activities of these compounds were determined by assaying their 1,1-diphenyl-2-picrylhydrazyl radical and nitroblue tetrazolium superoxide anion scavenging activity. All of the isolated phenolic compounds (1-10) exhibited potent anti-oxidative activities. In particular, 2 and 4, which are diarylheptanoids, and 10 which is ellagitannin exhibited excellent anti-oxidative activities with almost the same potency as that of the positive controls L-ascorbic acid and allopurinol.

  8. Influence of heat treatment on antioxidant capacity and (poly)phenolic compounds of selected vegetables.

    PubMed

    Juániz, Isabel; Ludwig, Iziar A; Huarte, Estibaliz; Pereira-Caro, Gema; Moreno-Rojas, Jose Manuel; Cid, Concepción; De Peña, María-Paz

    2016-04-15

    The impact of cooking heat treatments (frying in olive oil, frying in sunflower oil and griddled) on the antioxidant capacity and (poly)phenolic compounds of onion, green pepper and cardoon, was evaluated. The main compounds were quercetin and isorhamnetin derivates in onion, quercetin and luteolin derivates in green pepper samples, and chlorogenic acids in cardoon. All heat treatments tended to increase the concentration of phenolic compounds in vegetables suggesting a thermal destruction of cell walls and sub cellular compartments during the cooking process that favor the release of these compounds. This increase, specially that observed for chlorogenic acids, was significantly correlated with an increase in the antioxidant capacity measured by DPPH (r=0.70). Griddled vegetables, because of the higher temperature applied during treatment in comparison with frying processes, showed the highest amounts of phenolic compounds with increments of 57.35%, 25.55% and 203.06% compared to raw onion, pepper and cardoon, respectively.

  9. Two new phenolic compounds from the leaves of Alnus sibirica Fisch. ex Turcz.

    PubMed Central

    Kim, Manh Heun; Park, Kwan Hee; Kim, So Ra; Park, Kwang Jun; Oh, Myeong Hwan; Heo, Jun Hyeok; Yoon, Ki Hoon; Yin, Jun; Yoon, Kyu Hyung; Lee, Min Won

    2016-01-01

    Two new phenolic compounds, 4-O-glucopyranosyl-5-O-caffeoylshikimic acid (1) and 2,3-digalloyl oregonin (2), were isolated along with eight known phenolic compounds (3–10) from an 80% acetone extract of Alnus sibirica leaves. The chemical structures of these compounds were elucidated using 1D/2D nuclear magnetic resonance and high resolution-MS. The anti-oxidative activities of these compounds were determined by assaying their 1,1-diphenyl-2-picrylhydrazyl radical and nitroblue tetrazolium superoxide anion scavenging activity. All of the isolated phenolic compounds (1–10) exhibited potent anti-oxidative activities. In particular, 2 and 4, which are diarylheptanoids, and 10 which is ellagitannin exhibited excellent anti-oxidative activities with almost the same potency as that of the positive controls L-ascorbic acid and allopurinol. PMID:26211877

  10. Influence of heat treatment on antioxidant capacity and (poly)phenolic compounds of selected vegetables.

    PubMed

    Juániz, Isabel; Ludwig, Iziar A; Huarte, Estibaliz; Pereira-Caro, Gema; Moreno-Rojas, Jose Manuel; Cid, Concepción; De Peña, María-Paz

    2016-04-15

    The impact of cooking heat treatments (frying in olive oil, frying in sunflower oil and griddled) on the antioxidant capacity and (poly)phenolic compounds of onion, green pepper and cardoon, was evaluated. The main compounds were quercetin and isorhamnetin derivates in onion, quercetin and luteolin derivates in green pepper samples, and chlorogenic acids in cardoon. All heat treatments tended to increase the concentration of phenolic compounds in vegetables suggesting a thermal destruction of cell walls and sub cellular compartments during the cooking process that favor the release of these compounds. This increase, specially that observed for chlorogenic acids, was significantly correlated with an increase in the antioxidant capacity measured by DPPH (r=0.70). Griddled vegetables, because of the higher temperature applied during treatment in comparison with frying processes, showed the highest amounts of phenolic compounds with increments of 57.35%, 25.55% and 203.06% compared to raw onion, pepper and cardoon, respectively. PMID:26616976

  11. Targeted analysis of bioactive phenolic compounds and antioxidant activity of Macedonian red wines.

    PubMed

    Ivanova-Petropulos, Violeta; Ricci, Arianna; Nedelkovski, Dusko; Dimovska, Violeta; Parpinello, Giuseppina P; Versari, Andrea

    2015-03-15

    Phenolic composition of twenty-two Macedonian red wines, including ten autochthonous monovarietal Vranec wines produced with different yeasts for fermentation, and twelve wines from international varieties (Syrah, Merlot and Cabernet Sauvignon) from different wine regions was studied. All wines presented relatively high value of total phenols and antioxidant activity. A total of 19 phenolic compounds were identified and quantified using HPLC-DAD and among them, malvidin-3-glucoside and its derivatives were the major compounds, followed by the petunidin derivatives, while caftaric acid was the predominant cinnamic acid derivative in all wines. The anthocyanin content was mainly affected by the grape variety and to a less extent by the yeast used in fermentation. In particular, the use of locally isolated yeasts affected higher amount of anthocyanins and phenolic acids compared to the wines fermented with commercial yeasts. Principal Component Analysis showed a satisfactory grouping of red wines according to the grape variety.

  12. Antioxidant capacity and phenolic acids of virgin coconut oil.

    PubMed

    Marina, A M; Man, Y B Che; Nazimah, S A H; Amin, I

    2009-01-01

    The antioxidant properties of virgin coconut oil produced through chilling and fermentation were investigated and compared with refined, bleached and deodorized coconut oil. Virgin coconut oil showed better antioxidant capacity than refined, bleached and deodorized coconut oil. The virgin coconut oil produced through the fermentation method had the strongest scavenging effect on 1,1-diphenyl-2-picrylhydrazyl and the highest antioxidant activity based on the beta-carotene-linoleate bleaching method. However, virgin coconut oil obtained through the chilling method had the highest reducing power. The major phenolic acids detected were ferulic acid and p-coumaric acid. Very high correlations were found between the total phenolic content and scavenging activity (r=0.91), and between the total phenolic content and reducing power (r=0.96). There was also a high correlation between total phenolic acids and beta-carotene bleaching activity. The study indicated that the contribution of antioxidant capacity in virgin coconut oil could be due to phenolic compounds.

  13. Plant growth and phenolic compounds in the rhizosphere soil of wild oat (Avena fatua L.)

    PubMed Central

    Iannucci, Anna; Fragasso, Mariagiovanna; Platani, Cristiano; Papa, Roberto

    2013-01-01

    The objectives of this study were to determine the pattern of dry matter (DM) accumulation and the evolution of phenolic compounds in the rhizosphere soil from tillering to the ripe seed stages of wild oat (Avena fatua L.), a widespread annual grassy weed. Plants were grown under controlled conditions and harvested 13 times during the growing season. At each harvest, shoot and root DM and phenolic compounds in the rhizosphere soil were determined. The maximum DM production (12.6 g/plant) was recorded at 122 days after sowing (DAS; kernel hard stage). The increase in total aerial DM with age coincided with reductions in the leaf/stem and source/sink ratios, and an increase in the shoot/root ratio. HPLC analysis shows production of seven phenolic compounds in the rhizosphere soil of wild oat, in order of their decreasing levels: syringic acid, vanillin, 4-hydroxybenzoic acid, syringaldehyde, ferulic acid, p-cumaric acid and vanillic acid. The seasonal distribution for the total phenolic compounds showed two peaks of maximum concentrations, at the stem elongation stage (0.71 μg/kg; 82 DAS) and at the heading stage (0.70 μg/kg; 98 DAS). Thus, wild oat roots exude allelopathic compounds, and the levels of these phenolics in the rhizosphere soil vary according to plant maturity. PMID:24381576

  14. Composition of phenolic compounds and glycoalkaloids alpha-solanine and alpha-chaconine during commercial potato processing.

    PubMed

    Mäder, Jens; Rawel, Harshadrai; Kroh, Lothar W

    2009-07-22

    The influence of a commercial production process for dehydrated potato flakes on the content of free phenolic compounds, total phenolics, and glycoalkaloids in potatoes during the subsequent processing steps was determined. Processing byproducts, such as potato peel (steam peeling), mashed potato residues, and side streams (blanching and cooking waters), have also been investigated. A high-performance liquid chromatography (HPLC) method was developed to separate and quantify caffeic acid, gallic acid, ferulic acid, p-coumaric acid, p-hydoxybenzoic acid, protocatechuic acid, vanillic acid, catechin, and three isomers of caffeoylquinic acid: chlorogenic, neochlorogenic and cryptochlorogenic acid. Determination of the glycoalkaloids alpha-solanine and alpha-chaconine was performed by using a high-performance thin-layer chromatography (HPTLC) method. The deliverables reveal that processing potatoes to potato flakes remarkably diminishes the content of the analyzed compounds, mainly due to peeling and leaching. The influence of thermal exposure is less significant. About 43% of the initial phenolic acids and 10% of the glycoalkaloids remain after processing. The results of the total phenolic content assay by Folin-Ciocalteu reagent are proportional to the content of phenolic compounds determined by HPLC. Steam peeling has a higher influence on glycoalkaloid losses compared to that on phenolics. The highest amounts of phenolic compounds and glycoalkaloids were found in peeling byproduct. During processing, the amount of chlorogenic acid decreased, whereas the concentration of neochlorogenic acid increased due to isomerization. The impact of the results on potato processing technology is discussed.

  15. Simultaneous identification of glucosinolates and phenolic compounds in a representative collection of vegetable Brassica rapa.

    PubMed

    Francisco, Marta; Moreno, Diego A; Cartea, María Elena; Ferreres, Federico; García-Viguera, Cristina; Velasco, Pablo

    2009-09-18

    Brassica raparapa group is widely distributed and consumed in northwestern Spain. The consumption of Brassica vegetables has been related to human health due to their phytochemicals, such as glucosinolates and phenolic compounds that induce a variety of physiological functions including antioxidant activity, enzymes regulation and apoptosis control and the cell cycle. For first time in Brassica crops, intact glucosinolates and phenolic compounds were simultaneously identified and characterized. Twelve intact glucosinolates, belonging to the three chemical classes, and more than 30 phenolic compounds were found in B. rapa leaves and young shoots (turnip greens and turnip tops) by LC-UV photodiode array detection (PAD)-electrospray ionization (ESI). The main naturally occurring phenolic compounds identified were flavonoids and derivatives of hydroxycinnamic acids. The majority of the flavonoids were kaempferol, quercetin and isorhamnetin glycosylated and acylated with different hydroxycinnamic acids. Quantification of the main compounds by HPLC-PAD showed significant differences for most of compounds between plant organs. Total glucosinolate content value was 26.84 micromol g(-1) dw for turnip greens and 29.11 micromol g(-1) dw for turnip tops; gluconapin being the predominant glucosinolate (23.2 micromol g(-1) dw). Phenolic compounds were higher in turnip greens 51.71 micromol g(-1) dw than in turnip tops 38.99 micromol g(-1) dw, in which flavonols were always the major compounds.

  16. Effects of furan derivatives and phenolic compounds on electricity generation in microbial fuel cells

    NASA Astrophysics Data System (ADS)

    Catal, Tunc; Fan, Yanzhen; Li, Kaichang; Bermek, Hakan; Liu, Hong

    Lignocellulosic biomass is an attractive fuel source for MFCs due to its renewable nature and ready availability. Furan derivatives and phenolic compounds could be potentially formed during the pre-treatment process of lignocellulosic biomass. In this study, voltage generation from these compounds and the effects of these compounds on voltage generation from glucose in air-cathode microbial fuel cells (MFCs) were examined. Except for 5-hydroxymethyl furfural (5-HMF), all the other compounds tested were unable to be utilized directly for electricity production in MFCs in the absence of other electron donors. One furan derivate, 5-HMF and two phenolic compounds, trans-cinnamic acid and 3,5-dimethoxy-4-hydroxy-cinnamic acid did not affect electricity generation from glucose at a concentration up to 10 mM. Four phenolic compounds, including syringaldeyhde, vanillin, trans-4-hydroxy-3-methoxy, and 4-hydroxy cinnamic acids inhibited electricity generation at concentrations above 5 mM. Other compounds, including 2-furaldehyde, benzyl alcohol and acetophenone, inhibited the electricity generation even at concentrations less than 0.2 mM. This study suggests that effective electricity generation from the hydrolysates of lignocellulosic biomass in MFCs may require the employment of the hydrolysis methods with low furan derivatives and phenolic compounds production, or the removal of some strong inhibitors prior to the MFC operation, or the improvement of bacterial tolerance against these compounds through the enrichment of new bacterial cultures or genetic modification of the bacterial strains.

  17. Extraction of phenolic compounds from a Spodosol profile: an evaluation of three extractants

    SciTech Connect

    Vance, G.F.; Boyd, S.A.; Mokma, D.L.

    1985-12-01

    The authors extracted phenolic compounds from each horizon of a Spodosol profile using three extractants: 0.1 M sodium pyrophosphate at pH 7.0 and 10.2, and 0.5 N sodium hydroxide at pH 13.4. Of 28 standard compounds evaluated seven phenolic compounds were identified: three carboxylic acids - protocatechuic, p-hydroxybenzoic, and vanillic acids; two aldehydes - vanillin and p-hydroxybenzaldehyde; and two cinnamic acids - trans p-coumaric and ferulic acids. The three most abundant compounds evaluated were protocatechuic acid, p-hydroxybenzoic acid, and vanillic acid. The amounts of each phenolic compound extracted increased with increasing pH of the extractant except for protocatechuic acid. Protocatechuic acid was extracted in the highest amounts by sodium pyrophosphate pH 10. The pyrophosphate (pH .10) extracts revealed that protocatechuic acid tended to accumulate in the B horizons, suggesting that it may play a role in the translocation of metal ions during podzolization. The two cinnamic acids, trans p-coumaric and ferulic, were extracted primarily by NaOH. The identification of these cinnamic derivatives in an NaOH extraction of roots separated from the B horizon suggested that their presence may be due to degradation of plant residues by NaOH. Pyrophosphate (pH 7) extracted only small amounts of phenolic compounds. The specificity of pyrophosphate (pH 10) in removing organic complexes of a possible pedogenic nature suggest that it was the better extractant. Sodium pyrophosphate (pH 10) is recommended for use in future pedological studies of phenolic substances.

  18. Joint action of benzoxazinone derivatives and phenolic acids.

    PubMed

    Jia, Chunhong; Jia, Chunghong; Kudsk, Per; Mathiassen, Solvejg K

    2006-02-22

    The joint action of binary and ternary mixtures of benzoxazinone derivatives and phenolic acids was studied using the additive dose model (ADM) as reference model. The activity of fixed-ratio mixtures of phenolic acids [ferulic acid (FA), p-coumaric acid (CA), vanillic acid (VA), and p-hydroxybenzoic acid (HBA)] and benzoxazinone derivatives [2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), 6-methoxybenzoxazolin-2-one (MBOA), benzoxazolin-2-one (BOA), 2-aminophenol (AP), and N-(2-hydroxyphenyl)acetamide (HPAA)] on Lolium perenne and Myosotis arvensis root growth was assessed in Petri dishes. Root length was recorded 6 days after seeding, and EC(50) and EC(90) values were estimated using nonlinear regression analyses. The benzoxazinone derivatives were found to be more phytotoxic than the phenolic acids, particularly on M. arvensis. Binary mixtures of phenolic acids responded predominantly additively on both plant species. Deviations from additivity were species-specific with antagonistic responses on L. perenne and synergistic responses on M. arvensis. Similarly, binary mixtures of benzoxazinone derivatives also followed the ADM, although synergistic responses were observed for BOA + AP and BOA + HPAA. Binary and ternary mixtures of benzoxazinone derivatives and phenolic acids responded primarily antagonistically; however, a significant synergistic performance was observed with DIMBOA + FA and DIMBOA + VA on L. perenne. These results do not support the assumption that allelopathic effects of wheat can be attributed to synergistic effects of otherwise weakly active allelopathic compounds, and it is suggested that future research be directed toward identifying and studying the effects of other potential allelochemicals including the degradation products of the most abundant wheat allelochemicals.

  19. Determination of phenolic compounds in honey using dispersive liquid-liquid microextraction.

    PubMed

    Campone, Luca; Piccinelli, Anna Lisa; Pagano, Imma; Carabetta, Sonia; Di Sanzo, Rosa; Russo, Mariateresa; Rastrelli, Luca

    2014-03-21

    Honey is a valuable functional food rich in phenolic compounds with a broad spectrum of biological activities. Analysis of the phenolic compounds in honey is a very promising tool for the quality control, the authentication and characterization of botanical origin, and the nutraceutical research. This work describes a novel approach for the rapid analysis of five phenolic acids and 10 flavonoids in honey. Phenolic compounds were rapidly extracted and concentrated from diluted honey by dispersive liquid-liquid microextraction (DLLME) and then analyzed using high performance liquid chromatography with UV absorbance detection (HPLC-UV). Some important parameters, such as the nature and volume of extraction and dispersive solvents, pH and salt effect were carefully investigated and optimized to achieve the best extraction efficiency. Under the optimal conditions, an exhaustive extraction for twelve of the investigated analytes (recoveries >70%), with a precision (RSD<10%) highly acceptable for complex matrices, and detection and quantification limits at ppb levels (1.4-12 and 4.7-40ngg(-1), respectively) were attained. The proposed method, compared with the most widely used method in the analysis of phenolic compounds in honey, provided similar or higher extraction efficiency, except in the case of the most hydrophilic phenolic acids. The capability of DLLME to the extraction of other honey phytochemicals, such as abscisic acid, was also demonstrated. The main advantages of developed method are the simplicity of operation, the rapidity to achieve a very high sample throughput and low cost.

  20. Phenolic Compounds in Particles of Mainstream Waterpipe Smoke

    PubMed Central

    2013-01-01

    Introduction: Waterpipe tobacco smoking has in recent years become a popular international phenomenon, particularly among youth. While it has been shown to deliver significant quantities of several carcinogenic and toxic substances, phenols, an important class of chemical compounds thought to promote DNA mutation and cardiovascular diseases, however, has not been studied. Due to the relatively low temperature characteristic of waterpipe tobacco during smoking (i.e., <450 °C), it was hypothesized that phenolic compounds, which form at approximately 300 °C, will be found in abundance in waterpipe smoke. Methods: In this study, phenolic compounds in the particle phase of waterpipe mainstream smoke were quantified. Waterpipe and cigarette mainstream smoke generated using standard methods were collected on glass fiber pads and analyzed using gas chromatography/mass spectroscopy selected ion current profile chromatogram method for quantification. Results: We found that relative to a single cigarette, a waterpipe delivers at least 3 times greater quantities of the 7 analyzed phenols (phenol, o-cresol, m-cresol, p-cresol, catechol, resorcinol, and hydroquinone). Moreover, phenol derivatives such as methylcatechol, and flavorings such as vanillin, ethyl vanillin, and benzyl alcohol were found in quantities up to 1,000 times greater than the amount measured in the smoke of a single cigarette. Conclusion: The large quantities of phenols and phenol derivatives in waterpipe smoke add to the growing evidence that habitual waterpipe use may increase the risk of cancer and cardiovascular diseases. PMID:23178319

  1. Effects of microbial utilization of phenolic acids and their phenolic acid breakdown products on allelopathic interactions

    SciTech Connect

    Blum, U.

    1998-04-01

    Reversible sorption of phenolic acids by soils may provide some protection to phenolic acids from microbial degradation. In the absence of microbes, reversible sorption 35 days after addition of 0.5--3 {micro}mol/g of ferulic acid or p-coumaric acid was 8--14% in Cecil A{sub p} horizon and 31--38% in Cecil B{sub t} horizon soil materials. The reversibly sorbed/solution ratios (r/s) for ferulic acid or p-coumaric acid ranged from 0.12 to 0.25 in A{sub p} and 0.65 to 0.85 in B{sub t} horizon soil materials. When microbes were introduced, the r/s ratio for both the A{sub p} and B{sub t} horizon soil materials increased over time up to 5 and 2, respectively, thereby indicating a more rapid utilization of solution phenolic acids over reversibly sorbed phenolic acids. The increase in r/s ratio and the overall microbial utilization of ferulic acid and/or p-coumaric acid were much more rapid in A{sub p} than in B{sub t} horizon soil materials. Reversible sorption, however, provided protection of phenolic acids from microbial utilization for only very short periods of time. Differential soil fixation, microbial production of benzoic acids (e.g., vanillic acid and p-hydroxybenzoic acid) from cinnamic acids (e.g., ferulic acid and p-coumaric acid, respectively), and the subsequent differential utilization of cinnamic and benzoic acids by soil microbes indicated that these processes can substantially influence the magnitude and duration of the phytotoxicity of individual phenolic acids.

  2. Florets of sunflower (Helianthus annuus L.): potential new sources of dietary fiber and phenolic acids.

    PubMed

    Liang, Qiang; Cui, Jun; Li, Hang; Liu, Jia; Zhao, Guohua

    2013-04-10

    Ray florets (Rf) and disc florets (Df) are agricultural byproducts of sunflower seeds. Their nutrition-related compounds were determined. The dietary fiber contents in Rf and Df were 42.90 mg/100 g and 58.97 mg/100 g. In both florets, palmitic, linoleic, and linolenic acids were identified as the three most abundant fatty acids, and the saturated ones constitute approximately two-thirds (w/w) of the total fatty acids. Lysine was the limiting amino acid in both florets by World Health Organization standards. Sixteen phenolic compounds, nine free and eight bound, mainly depsides, were identified in florets by RP-HPLC-DAD/ESI-TOF-MS. The free and bound phenolic compounds in Df were higher than in Rf. 1,5-di-O-caffeoylquinic acid was the predominant free phenolic compound in both florets. The present study revealed that the florets of sunflower are rich sources of dietary fiber, Fe, and phenols.

  3. Soluble and bound phenolic compounds in different Bolivian purple corn ( Zea mays L.) cultivars.

    PubMed

    Cuevas Montilla, Elyana; Hillebrand, Silke; Antezana, Amalia; Winterhalter, Peter

    2011-07-13

    In nine Bolivian purple corn ( Zea mays L.) varieties the content of phenolic compounds as well as the anthocyanin composition has been determined. The phenotypes under investigation included four red and five blue varieties (Kulli, Ayzuma, Paru, Tuimuru, Oke, Huaca Songo, Colorado, Huillcaparu, and Checchi). In purple corn, phenolic compounds were highly concentrated in cell walls. Thus, simultaneous determination of soluble and bound-form phenolics is essential for analysis, extraction, and quantification. The present study reports the determination of soluble and insoluble-bound fraction of phenolic compounds by HPLC-DAD and HPLC-ESI-MS(n) in Bolivian purple corn varieties. Enzymatic, thermal, and alkaline hydrolyses were used to obtain the cell wall-linked phenolic compounds. Ferulic acid values ranged from 132.9 to 298.4 mg/100 g, and p-coumaric acid contents varied between 251.8 and 607.5 mg/100 g dry weight (DW), respectively, and were identified as the main nonanthocyanin phenolics. The total content of phenolic compounds ranged from 311.0 to 817.6 mg gallic acid equivalents (GAE)/100 g DW, and the percentage contribution of bound to total phenolics varied from 62.1 to 86.6%. The total monomeric anthocyanin content ranged from 1.9 to 71.7 mg cyanidin-3-glucoside equivalents/100 g DW. Anthocyanin profiles are almost the same among the different samples. Differences are observed only in the relative percentage of each anthocyanin. Cyanidin-3-glucoside and its malonated derivative were detected as major anthocyanins. Several dimalonylated monoglucosides of cyanidin, peonidin, and pelargonidin were present as minor constituents.

  4. Soluble and bound phenolic compounds in different Bolivian purple corn ( Zea mays L.) cultivars.

    PubMed

    Cuevas Montilla, Elyana; Hillebrand, Silke; Antezana, Amalia; Winterhalter, Peter

    2011-07-13

    In nine Bolivian purple corn ( Zea mays L.) varieties the content of phenolic compounds as well as the anthocyanin composition has been determined. The phenotypes under investigation included four red and five blue varieties (Kulli, Ayzuma, Paru, Tuimuru, Oke, Huaca Songo, Colorado, Huillcaparu, and Checchi). In purple corn, phenolic compounds were highly concentrated in cell walls. Thus, simultaneous determination of soluble and bound-form phenolics is essential for analysis, extraction, and quantification. The present study reports the determination of soluble and insoluble-bound fraction of phenolic compounds by HPLC-DAD and HPLC-ESI-MS(n) in Bolivian purple corn varieties. Enzymatic, thermal, and alkaline hydrolyses were used to obtain the cell wall-linked phenolic compounds. Ferulic acid values ranged from 132.9 to 298.4 mg/100 g, and p-coumaric acid contents varied between 251.8 and 607.5 mg/100 g dry weight (DW), respectively, and were identified as the main nonanthocyanin phenolics. The total content of phenolic compounds ranged from 311.0 to 817.6 mg gallic acid equivalents (GAE)/100 g DW, and the percentage contribution of bound to total phenolics varied from 62.1 to 86.6%. The total monomeric anthocyanin content ranged from 1.9 to 71.7 mg cyanidin-3-glucoside equivalents/100 g DW. Anthocyanin profiles are almost the same among the different samples. Differences are observed only in the relative percentage of each anthocyanin. Cyanidin-3-glucoside and its malonated derivative were detected as major anthocyanins. Several dimalonylated monoglucosides of cyanidin, peonidin, and pelargonidin were present as minor constituents. PMID:21639140

  5. Degradation of phenolic compounds by the lignocellulose deconstructing thermoacidophilic bacterium Alicyclobacillus Acidocaldarius

    SciTech Connect

    Aston, John E.; Apel, William A.; Lee, Brady D.; Thompson, David N.; Lacey, Jeffrey A.; Newby, Deborah T.; Reed, David. W.; Thompson, Vicki S.

    2015-11-05

    Alicyclobacillus acidocaldarius, a thermoacidophilic bacterium, has a repertoire of thermo- and acid-stable enzymes that deconstruct lignocellulosic compounds. The work presented here describes the ability of A. acidocaldarius to reduce the concentration of the phenolic compounds: phenol, ferulic acid, ρ-coumaric acid and sinapinic acid during growth conditions. The extent and rate of the removal of these compounds were significantly increased by the presence of micro-molar copper concentrations, suggesting activity by copper oxidases that have been identified in the genome of A. acidocaldarius. Substrate removal kinetics was first order for phenol, ferulic acid, ρ-coumaric acid and sinapinic acid in the presence of 50 μM copper sulfate. In addition, laccase enzyme assays of cellular protein fractions suggested significant activity on a lignin analog between the temperatures of 45 and 90 °C. As a result, this work shows the potential for A. acidocaldarius to degrade phenolic compounds, demonstrating potential relevance to biofuel production and other industrial processes.

  6. Degradation of phenolic compounds by the lignocellulose deconstructing thermoacidophilic bacterium Alicyclobacillus Acidocaldarius

    DOE PAGES

    Aston, John E.; Apel, William A.; Lee, Brady D.; Thompson, David N.; Lacey, Jeffrey A.; Newby, Deborah T.; Reed, David. W.; Thompson, Vicki S.

    2015-11-05

    Alicyclobacillus acidocaldarius, a thermoacidophilic bacterium, has a repertoire of thermo- and acid-stable enzymes that deconstruct lignocellulosic compounds. The work presented here describes the ability of A. acidocaldarius to reduce the concentration of the phenolic compounds: phenol, ferulic acid, ρ-coumaric acid and sinapinic acid during growth conditions. The extent and rate of the removal of these compounds were significantly increased by the presence of micro-molar copper concentrations, suggesting activity by copper oxidases that have been identified in the genome of A. acidocaldarius. Substrate removal kinetics was first order for phenol, ferulic acid, ρ-coumaric acid and sinapinic acid in the presence ofmore » 50 μM copper sulfate. In addition, laccase enzyme assays of cellular protein fractions suggested significant activity on a lignin analog between the temperatures of 45 and 90 °C. As a result, this work shows the potential for A. acidocaldarius to degrade phenolic compounds, demonstrating potential relevance to biofuel production and other industrial processes.« less

  7. Flavonoids and free phenolic acids from Phytolacca americana L. leaves.

    PubMed

    Bylka, W; Matławska, I

    2001-01-01

    In the leaves of Phytolacca americana L. flavonoid compounds: kaempferol 3-O-beta-D-glucopyranoside, kaempferol 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranoside, kaempferol 3-O-alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranoside, kaempferol 3-O-diglucoside and quercetin 3-O-glucoside were identified by chemical and spectroscopic methods and using co-chromatography, phenolic acids: p-hydroxybenzoic, vanillic, synapic, p-coumaric ferulic and caffeic were also confirmed.

  8. Phenolic acids in the flowers of Althaea rosea var. nigra.

    PubMed

    Dudek, Marlena; Matławska, Irena; Szkudlarek, Maurycy

    2006-01-01

    Distribution of phenolic acids in the flowers of Althaea rosea var. nigra has been studied by 2D-TLC and HPLC methods. The phenolic acids occurring in these fractions have been identified as ferulic, vanillic, syringic, p-coumaric, p-hydroxybenzoic, p-hydroxyphenylacetic and caffeic acids. By means of the HPLC methods the contents of major phenolic acids were estimated. From among the phenolic acids analyzed the syringic, p-hydroxybenzoic and p-coumaric acids are dominant. Total content of phenolic acids was determined by the Arnov's method.

  9. Pressurized liquid extraction of phenolic compounds from rice (Oryza sativa) grains.

    PubMed

    Setyaningsih, W; Saputro, I E; Palma, M; Barroso, C G

    2016-02-01

    An analytical pressurized liquid extraction (PLE) process has been studied for the extraction of phenolic compounds from rice grains. A fractional factorial design (2(7-2)) with a centre point was used to optimize PLE parameters such as solvent composition (EtOAc in MeOH), extraction temperature, pressure, flushing, static extraction time, solvent-purge and sample weight. Extraction temperature, solvent and static extraction time were found to have a significant effect on the response value. The optimized method was validated for selectivity, linearity, limits of detection and quantification, recovery and precision. The validated method was successfully applied for the analysis of a wide variety of rice grains. Seventeen phenolic compounds were detected in the sample and guaiacol, ellagic acid, vanillic acid and protocatechuic acid were identified as the most abundant compounds. Nonetheless, different species of rice show very varied compound diversity and levels of compounds in their grain compositions.

  10. Identification and Phytotoxicity Assessment of Phenolic Compounds in Chrysanthemoides monilifera subsp. monilifera (Boneseed).

    PubMed

    Al Harun, Md Abdullah Yousuf; Johnson, Joshua; Uddin, Md Nazim; Robinson, Randall W

    2015-01-01

    Chrysanthemoides monilifera subsp. monilifera (boneseed), a weed of national significance in Australia, threatens indigenous species and crop production through allelopathy. We aimed to identify phenolic compounds produced by boneseed and to assess their phytotoxicity on native species. Phenolic compounds in water and methanol extracts, and in decomposed litter-mediated soil leachate were identified using HPLC, and phytotoxicity of identified phenolics was assessed (repeatedly) through a standard germination bioassay on native Isotoma axillaris. The impact of boneseed litter on native Xerochrysum bracteatum was evaluated using field soil in a greenhouse. Collectively, we found the highest quantity of phenolic compounds in boneseed litter followed by leaf, root and stem. Quantity varied with extraction media. The rank of phenolics concentration in boneseed was in the order of ferulic acid > phloridzin > catechin > p-coumaric acid and they inhibited germination of I. axillaris with the rank of ferulic acid > catechin > phloridzin > p-coumaric acid. Synergistic effects were more severe compared to individual phenolics. The litter-mediated soil leachate (collected after15 days) exhibited strong phytotoxicity to I. axillaris despite the level of phenolic compounds in the decomposed leachate being decreased significantly compared with their initial level. This suggests the presence of other unidentified allelochemicals that individually or synergistically contributed to the phytotoxicity. Further, the dose response phytotoxic impacts exhibited by the boneseed litter-mediated soil to native X. bracteatum in a more naturalistic greenhouse experiment might ensure the potential allelopathy of other chemical compounds in the boneseed invasion. The reduction of leaf relative water content and chlorophyll level in X. bracteatum suggest possible mechanisms underpinning plant growth inhibition caused by boneseed litter allelopathy. The presence of a substantial quantity of free

  11. Identification and Phytotoxicity Assessment of Phenolic Compounds in Chrysanthemoides monilifera subsp. monilifera (Boneseed)

    PubMed Central

    Al Harun, Md Abdullah Yousuf; Johnson, Joshua; Uddin, Md Nazim; Robinson, Randall W.

    2015-01-01

    Chrysanthemoides monilifera subsp. monilifera (boneseed), a weed of national significance in Australia, threatens indigenous species and crop production through allelopathy. We aimed to identify phenolic compounds produced by boneseed and to assess their phytotoxicity on native species. Phenolic compounds in water and methanol extracts, and in decomposed litter-mediated soil leachate were identified using HPLC, and phytotoxicity of identified phenolics was assessed (repeatedly) through a standard germination bioassay on native Isotoma axillaris. The impact of boneseed litter on native Xerochrysum bracteatum was evaluated using field soil in a greenhouse. Collectively, we found the highest quantity of phenolic compounds in boneseed litter followed by leaf, root and stem. Quantity varied with extraction media. The rank of phenolics concentration in boneseed was in the order of ferulic acid > phloridzin > catechin > p-coumaric acid and they inhibited germination of I. axillaris with the rank of ferulic acid > catechin > phloridzin > p-coumaric acid. Synergistic effects were more severe compared to individual phenolics. The litter-mediated soil leachate (collected after15 days) exhibited strong phytotoxicity to I. axillaris despite the level of phenolic compounds in the decomposed leachate being decreased significantly compared with their initial level. This suggests the presence of other unidentified allelochemicals that individually or synergistically contributed to the phytotoxicity. Further, the dose response phytotoxic impacts exhibited by the boneseed litter-mediated soil to native X. bracteatum in a more naturalistic greenhouse experiment might ensure the potential allelopathy of other chemical compounds in the boneseed invasion. The reduction of leaf relative water content and chlorophyll level in X. bracteatum suggest possible mechanisms underpinning plant growth inhibition caused by boneseed litter allelopathy. The presence of a substantial quantity of free

  12. Gas phase plasma impact on phenolic compounds in pomegranate juice.

    PubMed

    Herceg, Zoran; Kovačević, Danijela Bursać; Kljusurić, Jasenka Gajdoš; Jambrak, Anet Režek; Zorić, Zoran; Dragović-Uzelac, Verica

    2016-01-01

    The aim of the study was to evaluate the effect of gas phase plasma on phenolic compounds in pomegranate juice. The potential of near infrared reflectance spectroscopy combined with partial least squares for monitoring the stability of phenolic compounds during plasma treatment was explored, too. Experiments are designed to investigate the effect of plasma operating conditions (treatment time 3, 5, 7 min; sample volume 3, 4, 5 cm(3); gas flow 0.75, 1, 1.25 dm(3) min(-1)) on phenolic compounds and compared to pasteurized and untreated pomegranate juice. Pasteurization and plasma treatment resulted in total phenolic content increasing by 29.55% and 33.03%, respectively. Principal component analysis and sensitivity analysis outputted the optimal treatment design with plasma that could match the pasteurized sample concerning the phenolic stability (5 min/4 cm(3)/0.75 dm(3) min(-1)). Obtained results demonstrate the potential of near infrared reflectance spectroscopy that can be successfully used to evaluate the quality of pomegranate juice upon plasma treatment considering the phenolic compounds.

  13. Dynamic changes in phenolic compounds and antioxidant activity in oats (Avena nuda L.) during steeping and germination.

    PubMed

    Xu, Jian Guo; Tian, Cheng Rui; Hu, Qing Ping; Luo, Ji Yang; Wang, Xiang Dong; Tian, Xiang Dong

    2009-11-11

    Samples from naked oat were steeped and germinated under controlled conditions in an incubator. Changes of phenolic compounds and antioxidant activity were investigated in oats during steeping and germination. Results revealed that phenolic compounds and antioxidant activity of oats varied with the difference in steeping and germination stages. Compared with raw grains, short-term steeping treatment did not show significant effects (p > 0.05) on phenolic content. Germination can significantly result in the decrease in bound phenolic and the increase in free and total phenolics. Main phenolic acids and avenanthramides were isolated and quantified by HPLC analysis. During steeping, phenolic acids decreased (p < 0.05); avenanthramide N-(3',4'-dihydroxy)-(E)-cinnamoyl-5-hydroxyanthranilic acid first decreased and then increased (p < 0.05), while avenanthramides N-(4'-hydroxy)-(E)-cinnamoyl-5-hydroxyanthranilic acid and N-(4'-hydroxy-3'-methoxy)-(E)-cinnamoyl-5-hydroxyanthranilic acid did not change significantly (p > 0.05). During germination, gallic and caffeic acids first increased (p < 0.05) and then decreased, whereas p-coumaric and ferulic acids and avenanthramides increased (p < 0.05). Nevertheless, avenanthramides did not change significantly (p > 0.05) during the last stage of germination. Oat extracts exhibited increasing high antioxidant activity with the steeping and germination going on, which may explain that antioxidant activity correlated (p < 0.01) significantly with the content of phenolic compounds.

  14. Identification of Phenolic Compounds and Evaluation of Antioxidant and Antimicrobial Properties of Euphorbia Tirucalli L.

    PubMed Central

    de Araújo, Keline Medeiros; de Lima, Alessandro; Silva, Jurandy do N.; Rodrigues, Larissa L.; Amorim, Adriany G. N.; Quelemes, Patrick V.; dos Santos, Raimunda C.; Rocha, Jefferson A.; de Andrades, Éryka O.; Leite, José Roberto S. A.; Mancini-Filho, Jorge; da Trindade, Reginaldo Almeida

    2014-01-01

    Bioactive compounds extracted from natural sources can benefit human health. The aim of this work was to determine total phenolic content and antioxidant activity in extracts of Euphorbia tirucalli L. followed by identification and quantification of the phenolic compounds, as well as their antibacterial activities. Antioxidant activities were determined by DPPH and ABTS•+ assay. Identification of phenolic compounds was performed using high-performance liquid chromatography (HPLC), and antimicrobial activities were verified by agar dilution methods and MIC values. Total phenolic content ranged from 7.73 to 30.54 mg/100 g gallic acid equivalent. Extracts from dry plants showed higher antioxidant activities than those from fresh ones. The DPPH EC50 values were approximately 12.15 μg/mL and 16.59 μg/mL, respectively. Antioxidant activity measured by the ABTS method yielded values higher than 718.99 μM trolox/g for dry plants, while by the Rancimat® system yielded protection factors exceeding 1 for all extracts, comparable to synthetic BHT. Ferulic acid was the principal phenolic compound identified and quantified through HPLC-UV in all extracts. The extracts proved effective inhibitory potential for Staphylococcus epidermidis and Staphylococcus aureus. These results showed that extracts of Euphorbia tirucalli L. have excellent antioxidant capacity and moderate antimicrobial activity. These can be attributed to the high concentration of ferulic acid. PMID:26784670

  15. Determination of the major phenolic compounds in pomegranate juices by HPLC−DAD−ESI-MS.

    PubMed

    Gómez-Caravaca, Ana María; Verardo, Vito; Toselli, Moreno; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto; Caboni, Maria Fiorenza

    2013-06-01

    Traditionally, pomegranate (Punica granatum L.) has been consumed as fresh fruit or as pomegranate juice. In this study, the main phenolic compounds of 12 pomegranate varieties and 5 pomegranate clones were determined by HPLC−DAD−ESI-MS. Two chromatographic methods with a fused-core C18 column and a classical HPLC system were developed. Thirteen anthocyanins and fourteen other phenolic compounds were determined in the pomegranate juices. As far as we are concerned, a new flavonol-glycoside, phellatin or its isomer amurensin, has been tentatively identified for the first time in pomegranate juices. Total phenolic content ranged from 580.8 to 2551.3 mg/L of pomegranate juice. Anthocyanins varied between 20 to 82% of total phenolic content. Flavonoids were 1.6-23.6% of total phenolic compounds, while phenolic acids and ellagitannins were in the range 16.4-65.8%. The five clones reported a phenolic content comparable with that of the other pomegranate samples.

  16. Componential profile and amylase inhibiting activity of phenolic compounds from Calendula officinalis L. leaves.

    PubMed

    Olennikov, Daniil N; Kashchenko, Nina I

    2014-01-01

    An ethanolic extract and its ethyl acetate-soluble fraction from leaves of Calendula officinalis L. (Asteraceae) were found to show an inhibitory effect on amylase. From the crude extract fractions, one new phenolic acid glucoside, 6'-O-vanilloyl-β-D-glucopyranose, was isolated, together with twenty-four known compounds including five phenolic acid glucosides, five phenylpropanoids, five coumarins, and nine flavonoids. Their structures were elucidated based on chemical and spectral data. The main components, isoquercitrin, isorhamnetin-3-O-β-D-glucopyranoside, 3,5-di-O-caffeoylquinic acid, and quercetin-3-O-(6''-acetyl)-β-D-glucopyranoside, exhibited potent inhibitory effects on amylase.

  17. Determination of antioxidant capacity, phenolic acids, and fatty acid composition of rapeseed varieties.

    PubMed

    Szydłowska-Czerniak, Aleksandra; Trokowski, Konrad; Karlovits, György; Szłyk, Edward

    2010-07-14

    Three different analytical methods: ferric-reducing antioxidant power (FRAP), 2,2'-diphenyl-1-picrylhydrazyl (DPPH), and oxygen radical absorbance capacity (ORAC) were used for determination of antioxidant capacity of seven rapeseed varieties. Antioxidant capacity and levels of the total phenolic content, individual phenolic acids, fatty acid composition, and the selected physicochemical properties of the studied rapeseed cultivars were determined. Mean ORAC values for methanolic extracts of rapeseeds (4092-12989 mmol of Trolox/100 g) were significantly higher than FRAP and DPPH values (6218-7641 and 6238-7645 mumol of Trolox/100 g, respectively). Although FRAP and DPPH results were lower than ORAC values for all studied rapeseed varieties, there are linear and significant correlations between these three analytical methods (correlation coefficients ranged between 0.9124 and 0.9930, p < 0.005). Also, total phenolic compounds in rapeseeds correlated with antioxidant capacity (correlation coefficients ranged between 0.8708 and 0.9516, p < 0.01). Total phenolic acids determined by HPLC varied from 20.3 mg to 40.7 mg per 100 g of rapeseed flour, and the main phenolic acid is sinapic acid (17.4-36.4 mg/100 g). Fatty acid composition (SAFA = 7.2-8.6%, MUFA = 58.5-68.0%, PUFA = 24.7-33.9%) and the absence of trans-fatty acids indicate that the studied rapeseed varieties can be a source of unsaturated fatty acids and have a positive impact on human health.

  18. Phenolic Compounds in Extra Virgin Olive Oil Stimulate Human Osteoblastic Cell Proliferation.

    PubMed

    García-Martínez, Olga; De Luna-Bertos, Elvira; Ramos-Torrecillas, Javier; Ruiz, Concepción; Milia, Egle; Lorenzo, María Luisa; Jimenez, Brigida; Sánchez-Ortiz, Araceli; Rivas, Ana

    2016-01-01

    In this study, we aimed to clarify the effects of phenolic compounds and extracts from different extra virgin olive oil (EVOO) varieties obtained from fruits of different ripening stages on osteoblast cells (MG-63) proliferation. Cell proliferation was increased by hydroxytyrosol, luteolin, apigenin, p-coumaric, caffeic, and ferulic acids by approximately 11-16%, as compared with controls that were treated with one vehicle alone, while (+)-pinoresinol, oleuropein, sinapic, vanillic acid and derivative (vanillin) did not affect cell proliferation. All phenolic extracts stimulated MG-63 cell growth, and they induced higher cell proliferation rates than individual compounds. The most effective EVOO phenolic extracts were those obtained from the Picual variety, as they significantly increased cell proliferation by 18-22%. Conversely, Arbequina phenolic extracts increased cell proliferation by 9-13%. A decline in osteoblast proliferation was observed in oils obtained from olive fruits collected at the end of the harvest period, as their total phenolic content decreases at this late stage. Further research on the signaling pathways of olive oil phenolic compounds involved in the processes and their metabolism should be carried out to develop new interventions and adjuvant therapies using EVOO for bone health (i.e.osteoporosis) in adulthood and the elderly.

  19. Phenolic Compounds in Extra Virgin Olive Oil Stimulate Human Osteoblastic Cell Proliferation.

    PubMed

    García-Martínez, Olga; De Luna-Bertos, Elvira; Ramos-Torrecillas, Javier; Ruiz, Concepción; Milia, Egle; Lorenzo, María Luisa; Jimenez, Brigida; Sánchez-Ortiz, Araceli; Rivas, Ana

    2016-01-01

    In this study, we aimed to clarify the effects of phenolic compounds and extracts from different extra virgin olive oil (EVOO) varieties obtained from fruits of different ripening stages on osteoblast cells (MG-63) proliferation. Cell proliferation was increased by hydroxytyrosol, luteolin, apigenin, p-coumaric, caffeic, and ferulic acids by approximately 11-16%, as compared with controls that were treated with one vehicle alone, while (+)-pinoresinol, oleuropein, sinapic, vanillic acid and derivative (vanillin) did not affect cell proliferation. All phenolic extracts stimulated MG-63 cell growth, and they induced higher cell proliferation rates than individual compounds. The most effective EVOO phenolic extracts were those obtained from the Picual variety, as they significantly increased cell proliferation by 18-22%. Conversely, Arbequina phenolic extracts increased cell proliferation by 9-13%. A decline in osteoblast proliferation was observed in oils obtained from olive fruits collected at the end of the harvest period, as their total phenolic content decreases at this late stage. Further research on the signaling pathways of olive oil phenolic compounds involved in the processes and their metabolism should be carried out to develop new interventions and adjuvant therapies using EVOO for bone health (i.e.osteoporosis) in adulthood and the elderly. PMID:26930190

  20. Phenolic Compounds in Extra Virgin Olive Oil Stimulate Human Osteoblastic Cell Proliferation

    PubMed Central

    García-Martínez, Olga; De Luna-Bertos, Elvira; Ramos-Torrecillas, Javier; Ruiz, Concepción; Milia, Egle; Lorenzo, María Luisa; Jimenez, Brigida; Sánchez-Ortiz, Araceli; Rivas, Ana

    2016-01-01

    In this study, we aimed to clarify the effects of phenolic compounds and extracts from different extra virgin olive oil (EVOO) varieties obtained from fruits of different ripening stages on osteoblast cells (MG-63) proliferation. Cell proliferation was increased by hydroxytyrosol, luteolin, apigenin, p-coumaric, caffeic, and ferulic acids by approximately 11–16%, as compared with controls that were treated with one vehicle alone, while (+)-pinoresinol, oleuropein, sinapic, vanillic acid and derivative (vanillin) did not affect cell proliferation. All phenolic extracts stimulated MG-63 cell growth, and they induced higher cell proliferation rates than individual compounds. The most effective EVOO phenolic extracts were those obtained from the Picual variety, as they significantly increased cell proliferation by 18–22%. Conversely, Arbequina phenolic extracts increased cell proliferation by 9–13%. A decline in osteoblast proliferation was observed in oils obtained from olive fruits collected at the end of the harvest period, as their total phenolic content decreases at this late stage. Further research on the signaling pathways of olive oil phenolic compounds involved in the processes and their metabolism should be carried out to develop new interventions and adjuvant therapies using EVOO for bone health (i.e.osteoporosis) in adulthood and the elderly. PMID:26930190

  1. [On the phenolic acids of vegetables. IV. Hydroxycinnamic acids and hydroxybenzoic acids of vegetables and potatoes (author's transl)].

    PubMed

    Schmidtlein, H; Herrmann, K

    1975-12-16

    Lettuce, endive and chicory exclusively, cornsalad and sweet fennel almost exclusively contain caffeic acid derivatives beside traces of ferulic acid. Parsley exclusively and spinach almost exclusively show p-coumaric acid derivatives. Compared to root, fruit and seed vegetables the contents of phenolic acids in green leaves are considerably high. Rhubarb is the only vegetable, which contains gallic acid (chief phenolic acid) beside hydroxycinnamic, protocatechuic and vanillic acid derivatives. Furthermore hydroxybenzoic acid derivatives (salicylic, gentisic and vanillic acid) occur in cornsalad, sweet fennel, parsley and spinach in small concentrations; cornsalad shows p-hydroxybenzoic acid (ca. 20 mg/kg). Onions (Allium cepa) contain almost only protocatechuic acid beside small amounts of p-hydroxybenzoic and vanillic acid. In the outer dry coloured skins protocatechuic acid reaches concentrations up to 2% of plant material; the internal pulpy tissues show lower concentrations (ca. 20 mg/kg). On the contrary to the bulbs the green leaves of onions like chive and leek contain almost exclusively compounds of ferulic and p-coumaric acid. Garlic even shows a different phenolic acid pattern of skins and internal tissues. The caffeic acid derivatives of potatoes are mainly localized to a 1--2 mm thick outer layer. The different localization of phenolic acids in the different parts of vegetable plants is discussed.

  2. Phenolic compound profiles and their corresponding antioxidant Capacity of purple pitaya (Hylocereus sp.) genotypes.

    PubMed

    Esquivel, Patricia; Stintzing, Florian C; Carle, Reinhold

    2007-01-01

    Folin-Ciocalteu and TEAC (Trolox equivalent antioxidant capacity) assay together with the spectrophotometric determination of betalains were applied to investigate the correlation between phenolics and their contribution to the antioxidant capacity of five different Costa Rican genotypes of purple pitaya (Hylocereus sp.) and of H. polyrhizus fruits. Maximum antioxidant capacity, total phenolic and betalain contents were observed in the genotype 'Lisa'. While non-betalainic phenolic compounds contributed only to a minor extent, betalains were responsible for the major antioxidant capacity of purple pitaya juices evaluated. The phenolic pattern of each genotype was also thoroughly investigated using liquid chromatography coupled to positive electrospray ionization (ESI) tandem mass spectrometry. In addition to the well known betalains previously reported in Hylocereus fruits, several biosynthetic precursors were detected. Notably, decarboxylated and dehydrogenated betalains were identified as genuine compounds of the juices. Some of these compounds were previously described as artifacts upon heat exposure. Moreover, gallic acid was identified for the first time in pitaya fruits. While the phenolic profiles generally differed between genotypes, phenolic compound composition of 'Rosa' resembled that of H. polyrhizus with respect to total contents of betacyanins, betalainic precursors, phyllocactin and cyclo-Dopa malonyl-glucosides.

  3. Olive phenolic compounds: metabolic and transcriptional profiling during fruit development

    PubMed Central

    2012-01-01

    Background Olive (Olea europaea L.) fruits contain numerous secondary metabolites, primarily phenolics, terpenes and sterols, some of which are particularly interesting for their nutraceutical properties. This study will attempt to provide further insight into the profile of olive phenolic compounds during fruit development and to identify the major genetic determinants of phenolic metabolism. Results The concentration of the major phenolic compounds, such as oleuropein, demethyloleuropein, 3–4 DHPEA-EDA, ligstroside, tyrosol, hydroxytyrosol, verbascoside and lignans, were measured in the developing fruits of 12 olive cultivars. The content of these compounds varied significantly among the cultivars and decreased during fruit development and maturation, with some compounds showing specificity for certain cultivars. Thirty-five olive transcripts homologous to genes involved in the pathways of the main secondary metabolites were identified from the massive sequencing data of the olive fruit transcriptome or from cDNA-AFLP analysis. Their mRNA levels were determined using RT-qPCR analysis on fruits of high- and low-phenolic varieties (Coratina and Dolce d’Andria, respectively) during three different fruit developmental stages. A strong correlation was observed between phenolic compound concentrations and transcripts putatively involved in their biosynthesis, suggesting a transcriptional regulation of the corresponding pathways. OeDXS, OeGES, OeGE10H and OeADH, encoding putative 1-deoxy-D-xylulose-5-P synthase, geraniol synthase, geraniol 10-hydroxylase and arogenate dehydrogenase, respectively, were almost exclusively present at 45 days after flowering (DAF), suggesting that these compounds might play a key role in regulating secoiridoid accumulation during fruit development. Conclusions Metabolic and transcriptional profiling led to the identification of some major players putatively involved in biosynthesis of secondary compounds in the olive tree. Our data

  4. Extraction and quantification of phenolic acids and flavonols from Eugenia pyriformis using different solvents.

    PubMed

    Haminiuk, Charles Windson Isidoro; Plata-Oviedo, Manuel Salvador Vicente; de Mattos, Gisely; Carpes, Solange Teresinha; Branco, Ivanise Guilherme

    2014-10-01

    The recovery of phenolic compounds of Eugenia pyriformis using different solvents was investigated in this study. The compounds were identified and quantified by reverse-phase high-performance liquid chromatography coupled with ultraviolet-visible diode-array detector (RP-HPLC-DAD/UV-vis). Absolute methanol was the most effective extraction agent of phenolic acids and flavonols (588.31 mg/Kg) from Eugenia pyriformis, although similar results (p ≤ 0.05) were observed using methanol/water (1:1 ratio). Our results clearly showed that higher contents of phenolic compounds were not obtained either with the most or the least polar solvents used. Several phenolic compounds were identified in the samples whereas gallic acid and quercetin were the major compounds recovered. PMID:25328239

  5. Apples: content of phenolic compounds vs. variety, part of apple and cultivation model, extraction of phenolic compounds, biological properties.

    PubMed

    Kalinowska, Monika; Bielawska, Aleksandra; Lewandowska-Siwkiewicz, Hanna; Priebe, Waldemar; Lewandowski, Włodzimierz

    2014-11-01

    Apples are among the most popular fruits in the world. They are rich in phenolic compounds, pectin, sugar, macro- and microelements. Applying different extraction techniques it is possible to isolate a particular group of compounds or individual chemicals and then test their biological properties. Many reports point to the antioxidant, antimicrobial, anticancer and many other beneficial effects of apple components that may have potential applications in food, pharmaceutical and cosmetic industries. This paper summarizes and compiles information about apple phenolic compounds, their biological properties with particular emphasis on health-related aspects. The data are reviewed with regard to different apple varieties, part of apple, cultivation model and methods of extraction. PMID:25282014

  6. Apples: content of phenolic compounds vs. variety, part of apple and cultivation model, extraction of phenolic compounds, biological properties.

    PubMed

    Kalinowska, Monika; Bielawska, Aleksandra; Lewandowska-Siwkiewicz, Hanna; Priebe, Waldemar; Lewandowski, Włodzimierz

    2014-11-01

    Apples are among the most popular fruits in the world. They are rich in phenolic compounds, pectin, sugar, macro- and microelements. Applying different extraction techniques it is possible to isolate a particular group of compounds or individual chemicals and then test their biological properties. Many reports point to the antioxidant, antimicrobial, anticancer and many other beneficial effects of apple components that may have potential applications in food, pharmaceutical and cosmetic industries. This paper summarizes and compiles information about apple phenolic compounds, their biological properties with particular emphasis on health-related aspects. The data are reviewed with regard to different apple varieties, part of apple, cultivation model and methods of extraction.

  7. Comparison of phenolic compounds of orange juice processed by pulsed electric fields (PEF) and conventional thermal pasteurisation.

    PubMed

    Agcam, E; Akyıldız, A; Akdemir Evrendilek, G

    2014-01-15

    Processing of orange juice by pulsed electric fields (PEF) and thermal pasteurisation was carried out to compare changes in total phenolic concentration, hydroxybenzoic acid, hydroxycinnamic acids, flavonols, flavones and flavonones before and after being stored at 4°C for 180days. Changes in the initial total phenolic concentration of the samples varied depending on the applied electric field intensity and thermal pasteurisation. Hesperidin and chlorogenic acids were detected as the most abounded flavonoid and phenolic acids in the orange juice, respectively. Except for syringic acid and neoeriocitrin, the concentration of the phenolic compounds indentified in the orange juice samples enhanced after the PEF or thermal pasteurisation. The samples treated with PEF had more stable flavonoids and phenolic acids than those treated with the thermal pasteurisation. The PEF-treated samples had higher sensory scores than the heat-treated samples.

  8. Influence of the stage of ripeness on the composition of iridoids and phenolic compounds in genipap (Genipa americana L.).

    PubMed

    Bentes, Adria de Sousa; Mercadante, Adriana Zerlotti

    2014-11-01

    Genipap fruits, native to the Amazon region, were classified in relation to their stage of ripeness according to firmness and peel color. The influence of the part of the genipap fruit and ripeness stage on the iridoid and phenolic compound profiles was evaluated by HPLC-DAD-MS(n), and a total of 17 compounds were identified. Geniposide was the major compound in both parts of the unripe genipap fruits, representing >70% of the total iridoids, whereas 5-caffeoylquinic acid was the major phenolic compound. In ripe fruits, genipin gentiobioside was the major compound in the endocarp (38%) and no phenolic compounds were detected. During ripening, the total iridoid content decreased by >90%, which could explain the absence of blue pigment formation in the ripe fruits after their injury. This is the first time that the phenolic compound composition and iridoid contents of genipap fruits have been reported in the literature.

  9. Biological Activities of Phenolic Compounds Present in Virgin Olive Oil

    PubMed Central

    Cicerale, Sara; Lucas, Lisa; Keast, Russell

    2010-01-01

    The Mediterranean diet is associated with a lower incidence of atherosclerosis, cardiovascular disease, neurodegenerative diseases and certain types of cancer. The apparent health benefits have been partially ascribed to the dietary consumption of virgin olive oil by Mediterranean populations. Much research has focused on the biologically active phenolic compounds naturally present in virgin olive oils to aid in explaining reduced mortality and morbidity experienced by people consuming a traditional Mediterranean diet. Studies (human, animal, in vivo and in vitro) have demonstrated that olive oil phenolic compounds have positive effects on certain physiological parameters, such as plasma lipoproteins, oxidative damage, inflammatory markers, platelet and cellular function, antimicrobial activity and bone health. This paper summarizes current knowledge on the bioavailability and biological activities of olive oil phenolic compounds. PMID:20386648

  10. Rapid methods for extracting and quantifying phenolic compounds in citrus rinds.

    PubMed

    Magwaza, Lembe Samukelo; Opara, Umezuruike Linus; Cronje, Paul J R; Landahl, Sandra; Ortiz, Jose Ordaz; Terry, Leon A

    2016-01-01

    Conventional methods for extracting and quantifying phenolic compounds in citrus rinds are time consuming. Rapid methods for extracting and quantifying phenolic compounds were developed by comparing three extraction solvent combinations (80:20 v/v ethanol:H2O; 70:29.5:0.5 v/v/v methanol:H2O:HCl; and 50:50 v/v dimethyl sulfoxide (DMSO):methanol) for effectiveness. Freeze-dried, rind powder was extracted in an ultrasonic water bath at 35°C for 10, 20, and 30 min. Phenolic compound quantification was done with a high-performance liquid chromatography (HPLC) equipped with diode array detector. Extracting with methanol:H2O:HCl for 30 min resulted in the optimum yield of targeted phenolic acids. Seven phenolic acids and three flavanone glycosides (FGs) were quantified. The dominant phenolic compound was hesperidin, with concentrations ranging from 7500 to 32,000 μg/g DW. The highest yield of FGs was observed in samples extracted, using DMSO:methanol for 10 min. Compared to other extraction methods, methanol:H2O:HCl was efficient in optimum extraction of phenolic acids. The limit of detection and quantification for all analytes were small, ranging from 1.35 to 5.02 and 4.51 to 16.72 μg/g DW, respectively, demonstrating HPLC quantification method sensitivity. The extraction and quantification methods developed in this study are faster and more efficient. Where speed and effectiveness are required, these methods are recommended. PMID:26788305

  11. Phenolic Profiles and Contribution of Individual Compounds to Antioxidant Activity of Apple Powders.

    PubMed

    Raudone, Lina; Raudonis, Raimondas; Liaudanskas, Mindaugas; Viskelis, Jonas; Pukalskas, Audrius; Janulis, Valdimaras

    2016-05-01

    Apples (Malus domestica L.) are the most common source of phenolic compounds in northern European diet. Besides pectins, dietary fibers, vitamins, and oligosaccharides they contain phenolic compounds of different classes. Apple powders are convenient functional forms retaining significant amounts of phenolic antioxidants. In this study reducing and radical scavenging profiles of freeze-dried powders of "Aldas,ˮ "Auksis,ˮ "Connel Red,ˮ "Ligol,ˮ "Lodel,ˮ and "Rajkaˮ were determined and phenolic constituents were identified using ultra high-performance liquid chromatography coupled to quadrupole and time-of-flight mass spectrometers. A negative ionization mode was applied and seventeen compounds: phenolic acids (coumaroylquinic, chlorogenic), flavonoids (quercetin derivatives), and procyanidin derivatives (B1, B2, and C1) were identified in all tested apple samples. Total values of Trolox equivalents varied from 7.72 ± 0.32 up to 20.02 ± 0.52 and from 11.10 ± 0.57 up to 21.42 ± 0.75 μmol/g of dry weight of apple powder in FRAP (ferric reducing antioxidant power) and ABTS (2,2-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) postcolumn assays, respectively. The greatest Trolox equivalent values were determined for apples of "Aldasˮ cultivar. Chlorogenic acid and procyanidin C1 were the most significant contributors to total reducing and radical scavenging activity in all apple cultivars tested, therefore they could be considered as markers of antioxidant activity. PMID:27002313

  12. Effects of cooking methods on phenolic compounds in xoconostle (Opuntia joconostle).

    PubMed

    Cortez-García, Rosa María; Ortiz-Moreno, Alicia; Zepeda-Vallejo, Luis Gerardo; Necoechea-Mondragón, Hugo

    2015-03-01

    Xoconostle, the acidic cactus pear fruit of Opuntia joconostle of the Cactaceae family, is the source of several phytochemicals, such as betalain pigments and numerous phenolic compounds. The aim of the present study was to analyze the effect of four cooking procedures (i.e., boiling, grilling, steaming and microwaving) on the total phenolic content (TPC) and antioxidant activity (measured by ABTS, DPPH, reducing power, and BCBA) of xoconostle. In addition, HPLC-DAD analyses were performed to identify and quantify individual phenolic compounds. After microwaving and steaming xoconostle, the TPC remained the same that in fresh samples, whereas both grilling and boiling produced a significant, 20% reduction (p ≤ 0.05). Total flavonoids remained unchanged in boiled and grilled xoconostle, but steaming and microwaving increased the flavonoid content by 13 and 20%, respectively. Steaming and microwaving did not produce significant changes in the antioxidant activity of xoconostle, whereas boiling and grilling result in significant decreases. The phenolic acids identified in xoconostle fruits were gallic, vanillic, 4-hydroxybenzoic, syringic, ferulic and protocatechuic acids; the flavonoids identified were epicatechin, catechin, rutin, quercitrin, quercetin and kaempferol. Based on the results, steaming and microwaving are the most suitable methods for retaining the highest level of phenolic compounds and flavonoids in xoconostle.

  13. Optimization of ultrasound-assisted extraction of phenolic compounds from Cimicifugae rhizoma with response surface methodology

    PubMed Central

    Liu, Lin; Shen, Bao-Jia; Xie, Dong-Hao; Cai, Bao-Chang; Qin, Kun-Ming; Cai, Hao

    2015-01-01

    Background: Cimicifugae rhizoma was a Ranunculaceae herb belonging to the composite family, and the roots of C. rhizoma have been widely used in tradition Chinese medicine. Materials and Methods: Ultrasound-assisted extraction (UAE) of phenolic compounds from C. rhizoma. Caffeic acid (CA), isoferulic acid (IA), ferulic acid (FA), and total phenols were quantified by high-performance liquid chromatography-diode array detection and ultraviolet-visible spectrophotometer. Effects of several experimental parameters, such as ultrasonic power (W), extraction temperature (°C), and ethanol concentration (%) on extraction efficiencies of phenolic compounds from C. rhizoma were evaluated. Results: The results showed that the optimal UAE condition was obtained with ultrasonic power of 377.35 W, extraction temperature of 70°C, and ethanol concentration of 58.37% for total phenols, and ultrasonic power of 318.28 W, extraction temperature of 59.65°C, and ethanol concentration of 64.43% for combination of CA, IA, FA. Conclusions: The experimental values under optimal conditions were in good consistent with the predicted values, which suggested UAE is more efficient for the extraction of phenolic compounds from plant materials. PMID:26600711

  14. [Phenolic acid derivatives from Bauhinia glauca subsp. pernervosa].

    PubMed

    Zhao, Qiao-Li; Wu, Zeng-Bao; Zheng, Zhi-Hui; Lu, Xin-Hua; Liang, Hong; Cheng, Wei; Zhang, Qing-Ying; Zhao, Yu-Ying

    2011-08-01

    To study the chemical constituents of Bauhinia glauca subsp. pernervosa, eleven phenolic acids were isolated from a 95% ethanol extract by using a combination of various chromatographic techniques including column chromatography over silica gel, ODS, MCI, Sephadex LH-20, and semi-preparative HPLC. By spectroscopic techniques including 1H NMR, 13C NMR, 2D NMR, and HR-ESI-MS, these compounds were identified as isopropyl O-beta-(6'-O-galloyl)-glucopyranoside (1), ethyl O-beta-(6'-O-galloyl)-glucopyranoside (2), 3, 4, 5-trimethoxyphenyl-(6'-O-galloyl)-O-beta-D-glucopyranoside (3), 3, 4, 5-trimethoxyphenyl-beta-D-glucopyranoside (4), gallic acid (5), methyl gallate (6), ethyl gallate (7), protocatechuic acid (8), 3, 5-dimethoxy-4-hydroxybenzoic acid (9), erigeside C (10) and glucosyringic acid (11). Among them, compound 1 is a new polyhydroxyl compound; compounds 2, 10, and 11 were isolated from the genus Bauhinia for the first time, and the other compounds were isolated from the plant for the first time. Compounds 6 and 8 showed significant protein tyrosine phosphatase1B (PTP1B) inhibitory activity in vitro with the IC50 values of 72.3 and 54.1 micromol x L(-1), respectively.

  15. Brassica napus hairy roots and rhizobacteria for phenolic compounds removal.

    PubMed

    González, Paola S; Ontañon, Ornella M; Armendariz, Ana L; Talano, Melina A; Paisio, Cintia E; Agostini, Elizabeth

    2013-03-01

    Phenolic compounds are contaminants frequently found in water and soils. In the last years, some technologies such as phytoremediation have emerged to remediate contaminated sites. Plants alone are unable to completely degrade some pollutants; therefore, their association with rhizospheric bacteria has been proposed to increase phytoremediation potential, an approach called rhizoremediation. In this work, the ability of two rhizobacteria, Burkholderia kururiensis KP 23 and Agrobacterium rhizogenes LBA 9402, to tolerate and degrade phenolic compounds was evaluated. Both microorganisms were capable of tolerating high concentrations of phenol, 2,4-dichlorophenol (2,4-DCP), guaiacol, or pentachlorophenol (PCP), and degrading different concentrations of phenol and 2,4-DCP. Association of these bacterial strains with B. napus hairy roots, as model plant system, showed that the presence of both rhizospheric microorganisms, along with B. napus hairy roots, enhanced phenol degradation compared to B. napus hairy roots alone. These findings are interesting for future applications of these strains in phenol rhizoremediation processes, with whole plants, providing an efficient, economic, and sustainable remediation technology. PMID:22961561

  16. Removal of phenolic compounds from wastewaters using soybean peroxidase

    SciTech Connect

    Wright, H.; Nicell, J.A.

    1996-11-01

    Toxic and odiferous phenolic compounds are present in wastewaters generated by a variety of industries including petroleum refining, plastics, resins, textiles, and iron and steel manufacturing among others. Due to its commercial availability in purified form, its useful presence in raw plant material, and its proven ability to remove a variety of phenolic contaminants from wastewaters over a wide range of pH and temperature, horseradish peroxidase (HRP) appears to be the peroxidase enzyme of choice in enzymatic wastewater treatment studies. Problems with HRP catalyzed phenol removal, however, include the formation of toxic soluble reaction by-products, the cost of the enzyme, and costs associated with disposal of the phenolic precipitate generated. Enzyme costs are incurred because the enzyme is inactivated during the phenol removal process by various side reactions. While recent work has shown that enzyme inactivation can be reduced using chemical additives, the problem of enzyme cost could be circumvented by using a less expensive source of enzyme. In 1991, the seed coat of the soybean was identified as a very rich source of peroxidase enzyme. Since the seed coat of the soybean is a waste product of the soybean food industry, soybean peroxidase (SBP) has the potential of being a cost effective alternative to HRP in wastewater treatment. In this study, SBP is characterized in terms of its catalytic activity, its stability, and its ability to promote removal of phenolic compounds from synthetic wastewaters. Results obtained are discussed and compared to similar investigations using HRP.

  17. Identification of major phenolic compounds of Chinese water chestnut and their antioxidant activity.

    PubMed

    You, Yanli; Duan, Xuewu; Wei, Xiaoyi; Su, Xinguo; Zhao, Mouming; Sun, Jian; Ruenroengklin, Neungnapa; Jiang, Yueming

    2007-01-01

    Chinese water chestnut (CWC) is one of the most popular foods among Asian people due to its special taste and medical function. Experiments were conducted to test the antioxidant activity and then determine the major phenolic compound components present in CWC. CWC phenolic extract strongly inhibited linoleic acid oxidation and exhibited a dose-dependent free-radical scavenging activity against alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radicals, superoxide anions and hydroxyl radicals, which was superior to ascorbic acid and butylated hydroxytoluene (BHT), two commercial used antioxidants. Furthermore, the CWC extract was found to have a relatively higher reducing power, compared with BHT. The major phenolic compounds present in CWC tissues were extracted, purified and identified by high-performance liquid chromatograph (HPLC) as (-)-gallocatechin gallate, (-)-epicatechin gallate and (+)-catechin gallate. This study suggests that CWC tissues exhibit great potential for antioxidant activity and may be useful for their nutritional and medicinal functions.

  18. Ultrasound-assisted extraction of phenolic compounds from Laurus nobilis L. and their antioxidant activity.

    PubMed

    Muñiz-Márquez, Diana B; Martínez-Ávila, Guillermo C; Wong-Paz, Jorge E; Belmares-Cerda, Ruth; Rodríguez-Herrera, Raúl; Aguilar, Cristóbal N

    2013-09-01

    Bay leaves (BL) (Laurus nobilis L., Family: Laureceae) are traditionally used to treat some symptoms of gastrointestinal problems, such as epigastric bloating, impaired digestion, eructing and flatulence. These biological properties are mainly attributed to its phenolic compounds. In this paper, ultrasound-assisted extraction of phenolic compounds from Laurus nobilis L. (Laureceae) was studied. Effects of several experimental factors, such as sonication time, solid/liquid ratio and concentration of solvent on extraction of phenolic compounds were evaluated through a randomized complete block design with factorial treatment arrangement (3(3)). The best extraction conditions were: 1g plant sample with 12 mL of 35% ethanol, for 40 min, obtaining a yield of phenolic compounds of 17.32±1.52 mg g(-1) of plant. In addition, free radical-scavenging potential of DPPH and lipid oxidation inhibition, by linoleic acid peroxidation of the selected extract was measured in order to evidence their antioxidant properties. Results indicated that high amounts of phenolic compounds can be extracted from L. nobilis by ultrasound-assisted extraction technology. PMID:23523026

  19. Evaluation of total phenolic compounds and insecticidal and antioxidant activities of tomato hairy root extract.

    PubMed

    Singh, Harpal; Dixit, Sameer; Verma, Praveen Chandra; Singh, Pradhyumna Kumar

    2014-03-26

    Tomatoes are one of the most consumed crops in the whole world because of their versatile importance in dietary food as well as many industrial applications. They are also a rich source of secondary metabolites, such as phenolics and flavonoids. In the present study, we described a method to produce these compounds from hairy roots of tomato (THRs). Agrobacterium rhizogenes strain A4 was used to induce hairy roots in the tomato explants. The Ri T-DNA was confirmed by polymerase chain reaction amplification of the rolC gene. Biomass accumulation of hairy root lines was 1.7-3.7-fold higher compared to in vitro grown roots. Moreover, THRs efficiently produced several phenolic compounds, such as rutin, quercetin, kaempferol, gallic acid, protocatechuic acid, ferulic acid, colorogenic acid, and caffeic acid. Gallic acid [34.02 μg/g of dry weight (DW)] and rutin (20.26 μg/g of DW) were the major phenolic acid and flavonoid produced by THRs, respectively. The activities of reactive oxygen species enzymes (catalase, ascorbate peroxidase, and superoxide dismutase) were quantified. The activity of catalase in THRs was 0.97 ± 0.03 mM H2O2 min(-1) g(-1), which was 1.22-fold (0.79 ± 0.09 mM H2O2 min(-1) g(-1)) and 1.59-fold (0.61 ± 0.06 mM H2O2 min(-1) g(-1)) higher than field grown and in vitro grown roots, respectively. At 100 μL/g concentration, the phenolic compound extract caused 53.34 and 40.00% mortality against Helicoverpa armigera and Spodoptera litura, respectively, after 6 days. Surviving larvae of H. armigera and S. litura on the phenolic compound extract after 6 days showed 85.43 and 86.90% growth retardation, respectively. PMID:24635720

  20. The effects of plant growth regulators and L-phenylalanine on phenolic compounds of sweet basil.

    PubMed

    Koca, Nülüfer; Karaman, Şengül

    2015-01-01

    The effects of methyl jasmonate (MeJA), spermine (Spm), epibrassinolide (EBL) and l-phenylalanine on sweet basil (Ocimum basilicum L.) were studied to determine the amount of phenolic compounds and enzymatic activity of phenylalanine ammonia-lyase (PAL). Total phenolic and total flavonoid contents of sweet basils were determined by a spectrophotometer, and individual phenolic compounds and activity of PAL were analysed by HPLC/UV. The highest total phenolic (6.72 mg GAE/g) and total flavonoid contents (0.92 mg QE/g) obtained from 1.0 mM Spm+MeJA application. Rosmarinic acid (RA) and caffeic acid contents significantly enhanced after the applications but no such differences observed in chicoric acid content or PAL activity. RA was the main phenolic acid in all samples and its concentration varied from 1.04 to 2.70 mg/gFW. As a result the combinations of Spm+MeJA and EBL+MeJA can induce secondary metabolites effectively and those interactions play important role in the production of phytochemicals in plants.

  1. The effects of plant growth regulators and L-phenylalanine on phenolic compounds of sweet basil.

    PubMed

    Koca, Nülüfer; Karaman, Şengül

    2015-01-01

    The effects of methyl jasmonate (MeJA), spermine (Spm), epibrassinolide (EBL) and l-phenylalanine on sweet basil (Ocimum basilicum L.) were studied to determine the amount of phenolic compounds and enzymatic activity of phenylalanine ammonia-lyase (PAL). Total phenolic and total flavonoid contents of sweet basils were determined by a spectrophotometer, and individual phenolic compounds and activity of PAL were analysed by HPLC/UV. The highest total phenolic (6.72 mg GAE/g) and total flavonoid contents (0.92 mg QE/g) obtained from 1.0 mM Spm+MeJA application. Rosmarinic acid (RA) and caffeic acid contents significantly enhanced after the applications but no such differences observed in chicoric acid content or PAL activity. RA was the main phenolic acid in all samples and its concentration varied from 1.04 to 2.70 mg/gFW. As a result the combinations of Spm+MeJA and EBL+MeJA can induce secondary metabolites effectively and those interactions play important role in the production of phytochemicals in plants. PMID:25053088

  2. Antioxidant capacities, phenolic compounds and polysaccharide contents of 49 edible macro-fungi.

    PubMed

    Guo, Ya-Jun; Deng, Gui-Fang; Xu, Xiang-Rong; Wu, Shan; Li, Sha; Xia, En-Qin; Li, Fang; Chen, Feng; Ling, Wen-Hua; Li, Hua-Bin

    2012-11-01

    Edible macro-fungi are widely consumed as food sources for their flavors and culinary features. In order to explore the potential of macro-fungi as a natural resource of bioactive compounds, the antioxidant properties and polysaccharide contents of 49 edible macro-fungi from China were evaluated systematically. A positive correlation between antioxidant capacity and total phenolic content indicated that phenolic compounds could be main contributors of antioxidant capacities of these macro-fungi. Furthermore, many bioactive compounds such as gallic, homogentisic, protocatechuic, and p-hydroxybenzoic acid were identified and quantified. The macro-fungi species Thelephora ganbajun Zang, Boletus edulis Bull., Volvariella volvacea Sing, Boletus regius Krombh, and Suillus bovinus Kuntze displayed the highest antioxidant capacities and total phenolic contents, indicating their potential as important dietary sources of natural antioxidants.

  3. Removal of phenolic compounds in water by ultrafiltration membrane treatments.

    PubMed

    Acero, Juan L; Benítez, F Javier; Leal, Ana I; Real, Francisco J

    2005-01-01

    The ultrafiltration (UF) of aqueous solutions containing mixtures of three phenolic compounds (gallic acid, acetovanillone, and esculetin) was studied in a tangential UF laboratory system. These substances were selected as model pollutants present in the tannic fraction of the cork processing wastewaters. The two membranes used were a polyethersulfone membrane (Biomax5K) and a regenerated cellulose membrane (Ultracel5K), both with a molecular weight cut-off (MWCO) of 5000 Da. Previous experiments for the characterization of the membranes led to values for the water hydraulic permeability of 70.3 and 18.1 L/h x m2 x bar for the Biomax5K and Ultracel5K membranes, respectively. During the UF experiments, the permeate flow rate remained almost constant with processing time and the evolution of the pollutants concentrations varied depending on the nature of the membranes and the substances. The influence of the main operating variables (tansmembrane pressure and feed flow rate) on the permeate flux was established, and values for the apparent and intrinsic rejection coefficients were evaluated. Cork processing wastewater UF experiments were also conducted under similar operating conditions to those applied to the ultrapure water solutions. Removals of chemical oxygen demand, aromatic and tannic contents, and color were determined in these experiments, and the elimination of the three model compounds in the wastewater was also followed, with the evaluation of their apparent rejection coefficients.

  4. The influence of beverage composition on delivery of phenolic compounds from coffee and tea.

    PubMed

    Ferruzzi, Mario G

    2010-04-26

    Epidemiological data suggest that consumption of coffee and tea is associated with a reduced risk of several chronic and degenerative diseases including cardiovascular disorders, diabetes, obesity and neurodegenerative disorders. Both coffee and tea are a rich source of phenolic compounds including chlorogenic acids in coffee; and flavan-3-ols as well as complex theaflavins and thearubigens in tea. Coffee and tea are two of the most commonly consumed beverages in the world and thus represent a significant opportunity to positively affect disease risk and outcomes globally. Central to this opportunity is a need to better understand factors that may affect the bioavailability of specific phenolic components from coffee and tea based beverages. An overview of the phenolic composition of coffee and tea is discussed in the context of how processing and composition might influence phenolic profiles and bioavailability of individual phenolic components. Specifically, the impact of beverage formulation, the extent and type of processing and the influence of digestion on stability, bioavailability and metabolism of bioactive phenolics from tea and coffee are discussed. The impact of co-formulation with ascorbic acid and other phytochemicals are discussed as strategies to improve absorption of these health promoting phytochemicals. A better understanding of how the beverage composition impacts phenolic profiles and their bioavailability is critical to development of beverage products designed to deliver specific health benefits.

  5. Antioxidant activities and phenolic compounds of date plum persimmon ( Diospyros lotus L.) fruits.

    PubMed

    Gao, Hui; Cheng, Ni; Zhou, Juan; Wang, Bini; Deng, Jianjun; Cao, Wei

    2014-05-01

    In the present study, phenolic compounds are extracted from the date plum persimmon fruits using water, methanol and acetone as solvents. Antioxidant activities of the phenolic extracts are measured using four different tests, namely, DPPH, hydroxyl radical scavenging activities, chelating and reducing power assays. All the extracts show dose dependent DPPH radical scavenging activity, reducing and chelating powers and moreover, they are well correlated with the total phenolic and total flavonoid substances, suggesting direct contribution of phenolic compounds to these activities. In further, the extracts are identified and quantified by HPLC-ECD. Results show that gallic acid is the most abundant phenolic compound, with amounts ranging between 45.49and 287.47 μg/g dry sample. Myricetin is the dominant flavonoid in all extracts. Its level varied from 2.75 μg/g dry sample in acetone extract to 5.28 μg/g dry sample in water extract. On the basis of the results obtained, the date plum persimmon fruits phenolic extract is a potential source of natural antioxidants owing to its significant antioxidant activities. PMID:24803703

  6. Antioxidant activities and phenolic compounds of date plum persimmon ( Diospyros lotus L.) fruits.

    PubMed

    Gao, Hui; Cheng, Ni; Zhou, Juan; Wang, Bini; Deng, Jianjun; Cao, Wei

    2014-05-01

    In the present study, phenolic compounds are extracted from the date plum persimmon fruits using water, methanol and acetone as solvents. Antioxidant activities of the phenolic extracts are measured using four different tests, namely, DPPH, hydroxyl radical scavenging activities, chelating and reducing power assays. All the extracts show dose dependent DPPH radical scavenging activity, reducing and chelating powers and moreover, they are well correlated with the total phenolic and total flavonoid substances, suggesting direct contribution of phenolic compounds to these activities. In further, the extracts are identified and quantified by HPLC-ECD. Results show that gallic acid is the most abundant phenolic compound, with amounts ranging between 45.49and 287.47 μg/g dry sample. Myricetin is the dominant flavonoid in all extracts. Its level varied from 2.75 μg/g dry sample in acetone extract to 5.28 μg/g dry sample in water extract. On the basis of the results obtained, the date plum persimmon fruits phenolic extract is a potential source of natural antioxidants owing to its significant antioxidant activities.

  7. Photocatalytic degradation of phenol and phenolic compounds Part I. Adsorption and FTIR study.

    PubMed

    Araña, J; Pulido Melián, E; Rodríguez López, V M; Peña Alonso, A; Doña Rodríguez, J M; González Díaz, O; Pérez Peña, J

    2007-07-31

    With the goal of predicting the photocatalytic behaviour of different phenolic compounds (catechol, resorcinol, phenol, m-cresol and o-cresol), their adsorption and interaction types with the TiO(2) Degussa P-25 surface were studied. Langmuir and Freundlich isotherms were applied in the adsorption studies. The obtained results indicated that catechol adsorption is much higher than those of the other phenolics and its interaction occurs preferentially through the formation of a catecholate monodentate. Resorcinol and the cresols interact by means of hydrogen bonds through the hydroxyl group, and their adsorption is much lower than that of catechol. Finally, phenol showed an intermediate behaviour, with a Langmuir adsorption constant, K(L), much lower than that of catechol, but a similar interaction. The interaction of the selected molecules with the catalyst surface was evaluated by means of FTIR experiments, which allowed us to determine the probability of OH radical attack to the aromatic ring.

  8. HPLC Quantification of Phenolic Acids from Vetiveria zizanioides (L.) Nash and Its Antioxidant and Antimicrobial Activity

    PubMed Central

    Prajna, Jha; Richa, Jindal; Dipjyoti, Chakraborty

    2013-01-01

    Extraction procedure was standardized and for the soluble, glycoside, and wall-bound fractions of phenolic acids from Vetiveria zizanioides. The water soluble alkaline extract which represents the cell wall-bound fraction contained the highest amount of phenolic acids (2.62 ± 1.2 μM/g fwt GA equivalents). Increased phenolic content in the cell wall indicates more lignin deposition which has an important role in plant defense and stress mitigation. Antioxidant property expressed as percentage TEAC value obtained by ABTS assay was correlated with the amount of phenolic acids and showed a Pearson's coefficient 0.988 (significant at 0.01 level). The compounds p-coumaric acid, p-dihydroxybenzoic acid, and ferulic acid were detected in the acidic extracts by HPLC analysis. The plant extracts exhibited considerable antimicrobial activity against tested bacterial and fungal strains. PMID:26555971

  9. Content of phenolic compounds and antioxidant capacity in fruits of apricot genotypes.

    PubMed

    Sochor, Jiri; Zitka, Ondrej; Skutkova, Helena; Pavlik, Dusan; Babula, Petr; Krska, Boris; Horna, Ales; Adam, Vojtech; Provaznik, Ivo; Kizek, Rene

    2010-09-07

    Research on natural compounds is increasingly focused on their effects on human health. In this study, we were interested in the evaluation of nutritional value expressed as content of total phenolic compounds and antioxidant capacity of new apricot (Prunus armeniaca L.) genotypes resistant against Plum pox virus (PPV) cultivated on Department of Fruit Growing of Mendel University in Brno. Fruits of twenty one apricot genotypes were collected at the onset of consumption ripeness. Antioxidant capacities of the genotypes were determined spectrometrically using DPPH• (1,1-diphenyl-2-picryl-hydrazyl free radicals) scavenging test, TEAC (Trolox Equivalent Antioxidant Capacity), and FRAP (Ferric Reducing Antioxidant Power)methods. The highest antioxidant capacities were determined in the genotypes LE-3228 and LE-2527, the lowest ones in the LE-985 and LE-994 genotypes. Moreover, close correlation (r = 0.964) was determined between the TEAC and DPPH assays. Based on the antioxidant capacity and total polyphenols content, a clump analysis dendrogram of the monitored apricot genotypes was constructed. In addition, we optimized high performance liquid chromatography coupled with tandem electrochemical and spectrometric detection and determined phenolic profile consisting of the following fifteen phenolic compounds: gallic acid, 4-aminobenzoic acid, chlorogenic acid, ferulic acid, caffeic acid, procatechin, salicylic acid, p-coumaric acid, the flavonols quercetin and quercitrin, the flavonol glycoside rutin, resveratrol, vanillin, and the isomers epicatechin, (-)- and (+)- catechin.

  10. Retardation of myoglobin and haemoglobin-mediated lipid oxidation in washed bighead carp by phenolic compounds.

    PubMed

    Thiansilakul, Yaowapa; Benjakul, Soottawat; Grunwald, Eric W; Richards, Mark P

    2012-09-15

    Antioxidative activities of phenolic compounds (caffeic acid, gallic acid and tannic acid; 200 ppm) in washed mince (pH 6), with added myoglobin (Mb) and haemoglobin (Hb), from bighead carp (Hypophthalmichthys nobilis), during 9 days of iced storage, were studied. Tannic acid exhibited the preventive effect on discolouration of washed mince containing Mb or Hb during storage (P<0.05). High peroxide value (PV) was found and large amount of, thiobarbituric acid-reactive substances (TBARS) and hexanal were formed in washed mince containing haem proteins, especially Hb. As determined by apo Streptococcal haem-associated protein, Hb had the lower haem affinity than Mb. Phenolic compounds, especially caffeic acid and gallic acid, could lower lipid oxidation induced by Mb or Hb throughout storage (P<0.05). Prevention of haem release, as well as inhibition of lipid oxidation induced by haem proteins with selected phenolic compounds, should be an alternative means in lowering discolouration and lipid oxidation in fish muscle. PMID:23107692

  11. Alkaline extraction of phenolic compounds from intact sorghum kernels

    Technology Transfer Automated Retrieval System (TEKTRAN)

    An aqueous sodium hydroxide solution was employed to extract phenolic compounds from whole grain sorghum without decortication or grinding as determined by Oxygen Radical Absorbance Capacity (ORAC). The alkaline extract ORAC values were more stable over 32 days compared to neutralized and freeze dri...

  12. Breeding Vegetables with Increased Content in Bioactive Phenolic Acids.

    PubMed

    Kaushik, Prashant; Andújar, Isabel; Vilanova, Santiago; Plazas, Mariola; Gramazio, Pietro; Herraiz, Francisco Javier; Brar, Navjot Singh; Prohens, Jaime

    2015-01-01

    Vegetables represent a major source of phenolic acids, powerful antioxidants characterized by an organic carboxylic acid function and which present multiple properties beneficial for human health. In consequence, developing new varieties with enhanced content in phenolic acids is an increasingly important breeding objective. Major phenolic acids present in vegetables are derivatives of cinnamic acid and to a lesser extent of benzoic acid. A large diversity in phenolic acids content has been found among cultivars and wild relatives of many vegetable crops. Identification of sources of variation for phenolic acids content can be accomplished by screening germplasm collections, but also through morphological characteristics and origin, as well as by evaluating mutations in key genes. Gene action estimates together with relatively high values for heritability indicate that selection for enhanced phenolic acids content will be efficient. Modern genomics and biotechnological strategies, such as QTL detection, candidate genes approaches and genetic transformation, are powerful tools for identification of genomic regions and genes with a key role in accumulation of phenolic acids in vegetables. However, genetically increasing the content in phenolic acids may also affect other traits important for the success of a variety. We anticipate that the combination of conventional and modern strategies will facilitate the development of a new generation of vegetable varieties with enhanced content in phenolic acids.

  13. Evaluation of the protective effect of chemical additives in the oxidation of phenolic compounds catalysed by peroxidase.

    PubMed

    Torres, Juliana Arriel; Chagas, Pricila Maria Batista; Silva, Maria Cristina; Dos Santos, Custódio Donizete; Corrêa, Angelita Duarte

    2016-01-01

    The use of oxidoredutive enzymes in removing organic pollutants has been the subject of much research. The oxidation of phenolic compounds in the presence of chemical additives has been the focus of this study. In this investigation, the influence of the additives polyethylene glycol and Triton X-100 was evaluated in the phenol oxidation, caffeic acid, chlorogenic acid and total phenolic compounds present in coffee processing wastewater (CPW) at different pH values, performed by turnip peroxidase and peroxidase extracted from soybean seed hulls. The influence of these additives was observed only in the oxidation of phenol and caffeic acid. In the oxidation of other studied phenolic compounds, the percentage of oxidation remained unchanged in the presence of these chemical additives. In the oxidation of CPW in the presence of additives, no change in the oxidation of phenolic compounds was observed. Although several studies show the importance of evaluating the influence of additives on the behaviour of enzymes, this study found a positive response from the economic point of view for the treatment of real wastewater, since the addition of these substances showed no influence on the oxidation of phenolic compounds, which makes the process less costly.

  14. Evaluation of the protective effect of chemical additives in the oxidation of phenolic compounds catalysed by peroxidase.

    PubMed

    Torres, Juliana Arriel; Chagas, Pricila Maria Batista; Silva, Maria Cristina; Dos Santos, Custódio Donizete; Corrêa, Angelita Duarte

    2016-01-01

    The use of oxidoredutive enzymes in removing organic pollutants has been the subject of much research. The oxidation of phenolic compounds in the presence of chemical additives has been the focus of this study. In this investigation, the influence of the additives polyethylene glycol and Triton X-100 was evaluated in the phenol oxidation, caffeic acid, chlorogenic acid and total phenolic compounds present in coffee processing wastewater (CPW) at different pH values, performed by turnip peroxidase and peroxidase extracted from soybean seed hulls. The influence of these additives was observed only in the oxidation of phenol and caffeic acid. In the oxidation of other studied phenolic compounds, the percentage of oxidation remained unchanged in the presence of these chemical additives. In the oxidation of CPW in the presence of additives, no change in the oxidation of phenolic compounds was observed. Although several studies show the importance of evaluating the influence of additives on the behaviour of enzymes, this study found a positive response from the economic point of view for the treatment of real wastewater, since the addition of these substances showed no influence on the oxidation of phenolic compounds, which makes the process less costly. PMID:26502790

  15. Antibacterial activity of phenolic compounds and aromatic alcohols.

    PubMed

    Lucchini, J J; Corre, J; Cremieux, A

    1990-05-01

    The antibacterial properties of phenolic compounds and aromatic alcohols (growth inhibition, lethal effect and cytological damage) were investigated. The role of protein and RNA synthesis in the bactericidal action was also determined. All compounds tested demonstrated lethal properties and the ability to alter membranes, especially in Gram-negative bacteria. Efficacious concentrations, however, varied greatly among the compounds. These data corroborate previous findings which suggest that the mechanism of action of these compounds is related to their lipophilia. Moreover, since it was demonstrated that the lethal effect of two aromatic alcohols (phenethyl alcohol and benzyl alcohol) stops when protein synthesis is inhibited, it is likely that both possess specific mechanisms of action.

  16. Biological Activities of Phenolic Compounds of Extra Virgin Olive Oil

    PubMed Central

    Servili, Maurizio; Sordini, Beatrice; Esposto, Sonia; Urbani, Stefania; Veneziani, Gianluca; Maio, Ilona Di; Selvaggini, Roberto; Taticchi, Agnese

    2013-01-01

    Over the last few decades, multiple biological properties, providing antioxidant, anti-inflammatory, chemopreventive and anti-cancer benefits, as well as the characteristic pungent and bitter taste, have been attributed to Extra Virgin Olive Oil (EVOO) phenols. In particular, growing efforts have been devoted to the study of the antioxidants of EVOO, due to their importance from health, biological and sensory points of view. Hydrophilic and lipophilic phenols represent the main antioxidants of EVOO, and they include a large variety of compounds. Among them, the most concentrated phenols are lignans and secoiridoids, with the latter found exclusively in the Oleaceae family, of which the drupe is the only edible fruit. In recent years, therefore, we have tackled the study of the main properties of phenols, including the relationships between their biological activity and the related chemical structure. This review, in fact, focuses on the phenolic compounds of EVOO, and, in particular, on their biological properties, sensory aspects and antioxidant capacity, with a particular emphasis on the extension of the product shelf-life. PMID:26784660

  17. Simultaneous ozonation kinetics of phenolic acids present in wastewaters

    SciTech Connect

    Benitez, F.J.; Beltran-Heredia, J.; Acero, J.L.; Pinilla, M.L.

    1996-12-31

    Among the several chemical processes conducted for the removal of organic matter present in wastewaters coming from some agro-industrial plants (wine distilleries, olive oil mills, etc), the oxidation by ozone has shown a great effectiveness in the destruction of specially refractory pollutants: it is demonstrated that the biodegradability of those wastewaters increases aflcer an ozonation pretreatment. Their great pollutant character is imputed to the presence of some organic compounds, like phenols and polyphenols, which are toxic and inhibit the latter biological treatments. In this research, a competitive kinetic procedure reported by Clurol and Nekouinaini is applied to determine the degradation rate constants by ozone of several phenolic acids which are present in the wastewaters from the olive oil obtaining process. The resulting kinetic expressions for the ozonation reactions are useful for the successful design and operation of ozone reactors in water and wastewaters treatment plants.

  18. Enhanced Production of Phenolic Compounds from Pumpkin Leaves by Subcritical Water Hydrolysis

    PubMed Central

    Ko, Jeong-Yeon; Ko, Mi-Ok; Kim, Dong-Shin; Lim, Sang-Bin

    2016-01-01

    Enhanced production of individual phenolic compounds by subcritical water hydrolysis (SWH) of pumpkin leaves was investigated at various temperatures ranging from 100 to 220°C at 20 min and at various reaction times ranging from 10 to 50 min at 160°C. Caffeic acid, p-coumaric acid, ferulic acid, and gentisic acid were the major phenolic compounds in the hydrolysate of pumpkin leaves. All phenolic compounds except gentisic acid showed the highest yield at 160°C, but gentisic acid showed the highest yield at 180°C. The cumulative amount of individual phenolic compounds gradually increased by 48.1, 52.2, and 78.4 μg/g dry matter at 100°C, 120°C, and 140°C, respectively, and then greatly increased by 1,477.1 μg/g dry matter at 160°C. The yields of caffeic acid and ferulic acid showed peaks at 20 min, while those of cinnamic acid, p-coumaric acid, p-hydroxybenzoic acid, and procatechuic acid showed peaks at 30 min. Antioxidant activities such as 2,2-diphenyl-1-picrylhydrazyl and ferric reducing antioxidant power values gradually increased with hydrolysis temperature and ranged from 6.77 to 12.42 mg ascorbic acid equivalents/g dry matter and from 4.25 to 8.92 mmol Fe2+/100 g dry matter, respectively. Color L* and b* values gradually decreased as hydrolysis temperature increased from 100°C to 140°C. At high temperatures (160°C to 220°C), L* and b* values decreased suddenly. The a* value peaked at 160°C and then decreased as temperature increased from 160°C to 220°C. These results suggest that SWH of pumpkin leaves was strongly influenced by hydrolysis temperature and may enhanced the production of phenolic compounds and antioxidant activities. PMID:27390730

  19. Enhanced Production of Phenolic Compounds from Pumpkin Leaves by Subcritical Water Hydrolysis.

    PubMed

    Ko, Jeong-Yeon; Ko, Mi-Ok; Kim, Dong-Shin; Lim, Sang-Bin

    2016-06-01

    Enhanced production of individual phenolic compounds by subcritical water hydrolysis (SWH) of pumpkin leaves was investigated at various temperatures ranging from 100 to 220°C at 20 min and at various reaction times ranging from 10 to 50 min at 160°C. Caffeic acid, p-coumaric acid, ferulic acid, and gentisic acid were the major phenolic compounds in the hydrolysate of pumpkin leaves. All phenolic compounds except gentisic acid showed the highest yield at 160°C, but gentisic acid showed the highest yield at 180°C. The cumulative amount of individual phenolic compounds gradually increased by 48.1, 52.2, and 78.4 μg/g dry matter at 100°C, 120°C, and 140°C, respectively, and then greatly increased by 1,477.1 μg/g dry matter at 160°C. The yields of caffeic acid and ferulic acid showed peaks at 20 min, while those of cinnamic acid, p-coumaric acid, p-hydroxybenzoic acid, and procatechuic acid showed peaks at 30 min. Antioxidant activities such as 2,2-diphenyl-1-picrylhydrazyl and ferric reducing antioxidant power values gradually increased with hydrolysis temperature and ranged from 6.77 to 12.42 mg ascorbic acid equivalents/g dry matter and from 4.25 to 8.92 mmol Fe(2+)/100 g dry matter, respectively. Color L* and b* values gradually decreased as hydrolysis temperature increased from 100°C to 140°C. At high temperatures (160°C to 220°C), L* and b* values decreased suddenly. The a* value peaked at 160°C and then decreased as temperature increased from 160°C to 220°C. These results suggest that SWH of pumpkin leaves was strongly influenced by hydrolysis temperature and may enhanced the production of phenolic compounds and antioxidant activities. PMID:27390730

  20. Structure elucidation and antioxidant activity of the phenolic compounds from Rhynchosia suaveolens.

    PubMed

    Rammohan, Aluru; Gunasekar, Duvvuru; Reddy, Netala Vasudeva; Vijaya, Tartte; Devillee, Alexandre; Bodo, Bernard

    2015-04-01

    A new benzophenone, 2-hydroxy-3,4-dimethoxybenzophenone (1), together with a known C-glycosylxanthone, mangiferin (2) and two known C-glycosylflavones, isovitexin (3) and isoorientin (4), were isolated from the flowers of Rhynchosia suaveolens DC. (Fabaceae). The structure of the new compound (1) and the known compounds (2-4) were elucidated by extensive 1D and 2D NMR spectral studies. The plant extracts, as well as the isolated compounds, were evaluated for their total phenolic content (TPC), total flavonoid content (TFC) and DPPH radical scavenging activity. Among the isolated compounds, mangiferin (2) and isoorientin (4) showed significant radical scavenging activity comparable with that of ascorbic acid.

  1. Phenolic compounds in chestnut (Castanea sativa Mill.) heartwood. Effect of toasting at cooperage.

    PubMed

    Sanz, Miriam; Cadahía, Estrella; Esteruelas, Enrique; Muñoz, Angel Ma; Fernández de Simón, Brígida; Hernández, Teresa; Estrella, Isabel

    2010-09-01

    The phenolic and tannic composition of heartwood extracts from Castanea sativa Mill., before and after toasting in cooperage, were studied using HPLC-DAD and HPLC-DAD/ESI-MS, and some low molecular weight phenolic compounds and hydrolyzable tannins were found. The low molecular weight phenolic compounds were lignin constituents as the acids gallic, protocatechuic, vanillic, syringic, ferulic, and ellagic, the aldehydes protocatechuic, vanillic, syringic, coniferylic, and sinapic, and the coumarin scopoletin. Their patterns were somewhat different those of oak because oak does not contain compounds such protocatechuic acid and aldehyde and is composed of much lower amounts of gallic acid than chestnut. Vescalagin and castalagin were the main ellagitannins, and acutissimin was tentatively identified for the first time in this wood. Moreover, some gallotannins were tentatively identified, including different isomers of di, tri, tetra, and pentagalloyl glucopyranose, and di and trigalloyl-hexahydroxydiphenoyl glucopyranose, comprising 20 different compounds, as well as some ellagic derivatives such as ellagic acid deoxyhexose, ellagic acid dimer dehydrated, and valoneic acid dilactone. These ellagic derivatives as well as some galloyl and hexahydroxydiphenoyl derivatives were tentatively identified for the first time in this wood. The profile of tannins was therefore different from that of oak wood because oak only contains tannins of the ellagitannins type. Seasoned and toasted chestnut wood showed a very different balance between lignin derivatives and tannins because toasting resulted in the degradation of tannins and the formation of low molecular weight phenolic compounds from lignin degradation. Moreover, the different toasting levels provoked different balances between tannins and lignin constituents because the intensity of lignin and tannin degradation was in relation to the intensity of toasting.

  2. Phenolic Compounds of Pomegranate Byproducts (Outer Skin, Mesocarp, Divider Membrane) and Their Antioxidant Activities.

    PubMed

    Ambigaipalan, Priyatharini; de Camargo, Adriano Costa; Shahidi, Fereidoon

    2016-08-31

    Pomegranate peel was separated into outer leathery skin (PS), mesocarp (PM), and divider membrane (PD), and its phenolic compounds were extracted as free (F), esterified (E), and insoluble-bound (B) forms for the first time. The total phenolic content followed the order PD > PM > PS. ABTS(•+), DPPH, and hydroxyl radical scavenging activities and metal chelation were evaluated. In addition, pomegranate peel extracts showed inhibitory effects against α-glucosidase activity, lipase activity, and cupric ion-induced LDL-cholesterol oxidation as well as peroxyl and hydroxyl radical-induced DNA scission. Seventy-nine phenolic compounds were identified using HPLC-DAD-ESI-MS(n) mainly in the form of insoluble-bound. Thirty compounds were identified for the first time. Gallic acid was the major phenolic compound in pomegranate peel, whereas kaempferol 3-O-glucoside was the major flavonoid. Moreover, ellagic acid and monogalloyl-hexoside were the major hydrolyzable tannins, whereas the dominant proanthocyanidin was procyanidin dimers. Proanthocyanidins were detected for the first time. PMID:27509218

  3. Some phenolic compounds of extracts obtained from Origanum species growing in Turkey.

    PubMed

    Ozkan, Gülcan; Ozcan, Mehmet Musa

    2014-08-01

    Caffeic acid, rosmarinic acid, rutin, apigenin 7-O-glucoside, apigenin, and acesetin were the main phenolic compounds of Origanum onites extracts in all applications. While acesetin contents ranged from 133.59 mg/100 g (U1) to 437.25 mg/100 g (S3), rosmarinic acid changed between 215.94 mg/100 g (U4) and 1120.56 mg/100 g (S2) in Origanum vulgare L. subsp. hirtum (Link) Ietsw. Both rosmarinic acid and acesetin were not found in U5 application. Only caffeic acid (19.39 mg/100 g) was found in U5 application. Rosmarinic acid contents of O. onites extract changed between 158.62 mg/100 g (U5) and 799.87 mg/100 g (S2). Generally, dominant phenolic compound of Origanum extracts was rosmarinic acid compared with other extracts. In addition, methanol:water:acetic acid mixture (S2) (95:4.5:0.5) was found as the best application. Phenolic contents of extracts obtained with U series mixtures were found low.

  4. Phenols

    NASA Astrophysics Data System (ADS)

    Weber, Manfred; Weber, Markus

    Up to the end of the nineteenth century, phenol was recovered primarily from coal tar. With the commercialization of the phenolic resins, the demand for phenol grew significantly. Currently, the cumene-to-phenol process is the predominant synthetic route for the production of phenol. It is accompanied by acetone as a co-product. Cumene is oxidized with oxygen to form cumene hydroperoxide. The peroxide is subsequently decomposed to phenol and acetone, using a strong mineral acid as catalyst. The products are purified in a series of distillation columns. The cumene-to-phenol process is described in more detail in this chapter. An overview is given about synthetic routes via direct oxidation of benzene. None of these alternative routes has been commercialized. The chapter also gives an overview of global supply and use of phenol in 2008. Finally, the main natural sources and synthetic routes for cresols, xylenols, resorcinol, and bisphenol-A are described. These components are used as comonomers for special phenolic resins.

  5. Free phenolic acids in Ruta graveolens L. in vitro culture.

    PubMed

    Ekiert, H; Szewczyk, A; Kuś, A

    2009-10-01

    Eight phenolic acids were determined using HPLC method in methanolic extracts of Ruta graveolens L. (Rutaceae) shoots cultured in vitro on four variants of Linsmaier and Skoog (LS) medium differing in contents of growth regulators, NAA and BAP (ranging between 0.1-3.0 mg/l). Four compounds: protocatechuic, vanillic, syringic and p-coumaric acid were detected and quantified. The total content of metabolites was dependent on LS medium variants. The contents of protocatechuic acid, quantitatively dominating on all tested LS medium variants, were considerable (from 67.15 to 93.24 mg/100 g d.w.) in comparison with its contents in the plant material under analysis (46.36 to 218.27 mg/ 100 g d.w.). This is the first report of the isolation of protocatechuic acid from an in vitro plant culture.

  6. Characterization of free and conjugated phenolic compounds in fruits of selected wild plants.

    PubMed

    Ahmad, Naveed; Zuo, Yuegang; Lu, Xiaofei; Anwar, Farooq; Hameed, Sohail

    2016-01-01

    A gas chromatography-mass spectrometric (GC-MS) method was utilized for the separation, and systematic characterization of phenolic compounds as trimethylsilyl derivatives in fruits of wild plants including Olive, Jujube and Common Fig. Both the free and conjugate phenolic acids (rarely determined before and several are reported first time here) were characterized. A baseline separation of the 20 phenolics was achieved in 25 min with standard calibration curves linear over the concentration range from the detection limits to 20 μg/mL. Total of fourteen phenolic acids were identified in wild Olive fruit, eight in wild Jujube fruit and ten in wild Common Fig fruit, out of which 2,4-dihydroxybenzoic acid and trans-cinnamic acid were dominant in these fruits with concentration of 87.02, 5.25 and 14.16 mg/kg and 32.43, 5.77 and 11.70 mg/kg (dry weight), respectively. The results of this study support the utilization of the tested wild fruits as a potential source of valuable phenolics for functional food and nutraceutical applications.

  7. Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats.

    PubMed

    Yeh, Chi-Tai; Yen, Gow-Chin

    2006-08-01

    Phenolic acids have significant biological and pharmacological properties and some have demonstrated remarkable ability to alter sulfate conjugation. However, the modulatory effects of phenolic acids on phenol sulfotransferases (PSTs) in vivo have not been described. The present investigation evaluates the role of phenolic acid on the expression of PSTs in male Sprague-Dawley rat liver. According to the results, gentisic acid, gallic acid and p-coumaric acid in a dosage of 100 mg/kg of body weight for 14 consecutive days significantly increased P-form PST (PST-P) activity as compared with that of the control rats (P<.05), whereas the activity of M-form PST (PST-M) in rats that received gallic acid and p-coumaric acid were also significantly (P<.05) higher than in the control rats. Reverse transcriptase-polymerase chain reaction results indicated that the changes in both PST-P and PST-M mRNA levels by phenolic acids were similar to those noted in the enzyme activity levels. The plasma obtained from phenolic acid-administered rats had significantly (P<.05) increased oxygen radical absorbance capacity (ORAC(ROO*) values than that from control rats. In a bioavailability study, following oral administration of gallic acid and p-coumaric acid, the phenolic acids were detected in the plasma, and the Cmax values after 2.0-h administration were 665+/-23 and 550+/-33 nmol/L, respectively. There was a significant correlation between the activity of both forms of PSTs and the antioxidant capacity of ORAC(ROO*) value by phenolic acids (r=.74, P<.05 and r=.77, P<.05). These data suggest that phenolic acids might alter sulfate conjugation and antioxidant capacity in living systems. PMID:16443358

  8. Phenolic compounds of 'Galega Vulgar' and 'Cobrançosa' olive oils along early ripening stages.

    PubMed

    Peres, Fátima; Martins, Luisa L; Mourato, Miguel; Vitorino, Conceição; Antunes, Paulo; Ferreira-Dias, Suzana

    2016-11-15

    In this study, the lipophilic and hydrophilic phenol composition of virgin olive oils (VOO) obtained from olives from two of the most important Portuguese cultivars ('Galega Vulgar' and 'Cobrançosa'), harvested at different ripening stages and under two irrigation schemes (rain fed and irrigated), was evaluated. Phenolic alcohols (hydroxytyrosol and tyrosol), phenolic acids and derivatives and flavonoids (luteolin and apigenin), as well as tocopherols were quantified. Lipophilic (>300mgkg(-1)) and hydrophilic phenols (>600mgkg(-1)) were present in high contents in both VOO, for early ripening stages. Gamma-tocopherol content is higher in 'Galega Vulgar' VOO. Total phenols showed a decrease between ripening index 2.5 and 3.5. The dialdehydic form of elenolic acid linked to hydroxytyrosol (3,4-DHPEA-EDA), also known as oleacein, was the major phenolic compound identified in both oils. The concentration of free hydroxytyrosol and tyrosol in both VOO is very low while their esterified derivatives, like 3,4-DHPEA-EDA and p-HPEA-EDA, are much more abundant. PMID:27283606

  9. Phenolic compounds of 'Galega Vulgar' and 'Cobrançosa' olive oils along early ripening stages.

    PubMed

    Peres, Fátima; Martins, Luisa L; Mourato, Miguel; Vitorino, Conceição; Antunes, Paulo; Ferreira-Dias, Suzana

    2016-11-15

    In this study, the lipophilic and hydrophilic phenol composition of virgin olive oils (VOO) obtained from olives from two of the most important Portuguese cultivars ('Galega Vulgar' and 'Cobrançosa'), harvested at different ripening stages and under two irrigation schemes (rain fed and irrigated), was evaluated. Phenolic alcohols (hydroxytyrosol and tyrosol), phenolic acids and derivatives and flavonoids (luteolin and apigenin), as well as tocopherols were quantified. Lipophilic (>300mgkg(-1)) and hydrophilic phenols (>600mgkg(-1)) were present in high contents in both VOO, for early ripening stages. Gamma-tocopherol content is higher in 'Galega Vulgar' VOO. Total phenols showed a decrease between ripening index 2.5 and 3.5. The dialdehydic form of elenolic acid linked to hydroxytyrosol (3,4-DHPEA-EDA), also known as oleacein, was the major phenolic compound identified in both oils. The concentration of free hydroxytyrosol and tyrosol in both VOO is very low while their esterified derivatives, like 3,4-DHPEA-EDA and p-HPEA-EDA, are much more abundant.

  10. Phenolic compound profiles and antioxidant capacity of Persea americana Mill. peels and seeds of two varieties.

    PubMed

    Kosińska, Agnieszka; Karamać, Magdalena; Estrella, Isabel; Hernández, Teresa; Bartolomé, Begoña; Dykes, Gary A

    2012-05-01

    Avocado processing by the food and cosmetic industries yields a considerable amount of phenolic-rich byproduct such as peels and seeds. Utilization of these byproducts would be favorable from an economic point of view. Methanolic (80%) extracts obtained from lyophilized ground peels and seeds of avocado (Persea americana Mill.) of the Hass and Shepard varieties were characterized for their phenolic compound profiles using the HPLC-PAD technique. The structures of the identified compounds were subsequently unambiguously confirmed by ESI-MS. Compositional analysis revealed that the extracts contained four polyphenolic classes: flavanol monomers, proanthocyanidins, hydroxycinnamic acids, and flavonol glycosides. The presence of 3-O-caffeoylquinic acid, 3-O-p-coumaroylquinic acid, and procyanidin A trimers was identified in seeds of both varieties. Intervarietal differences were apparent in the phenolic compound profiles of peels. Peels of the Shepard variety were devoid of (+)-catechin and procyanidin dimers, which were present in the peels of the Hass variety. Peels of both varieties contained 5-O-caffeoylquinic acid and quercetin derivatives. The differences in the phenolic profiles between varietals were also apparent in the different antioxidant activity of the extracts. The peel extracts had a higher total phenolic compound content and antioxidant activity when compared to the seed extracts. The highest TEAC and ORAC values were apparent in peels of the Haas variety in which they amounted to 0.16 and 0.47 mmol Trolox/g DW, respectively. No significant (p > 0.05) differences were apparent between the TEAC values of seeds of the two varieties but the ORAC values differed significantly (p < 0.05). Overall these findings indicate that both the seeds and peel of avocado can be utilized as a functional food ingredient or as an antioxidant additive.

  11. Irreversible adsorption of phenolic compounds by activated carbons

    SciTech Connect

    Grant, T.M.; King, C.J.

    1988-12-01

    Studies were undertaken to determine the reasons why phenolic sorbates can be difficult to remove and recover from activated carbons. The chemical properties of the sorbate and the adsorbent surface, and the influences of changes in the adsorption and desorption conditions were investigated. Comparison of isotherms established after different contact times or at different temperatures indicated that phenolic compounds react on carbon surfaces. The reaction rate is a strong function of temperature. Regeneration of carbons by leaching with acetone recovered at least as much phenol as did regeneration with other solvents or with displacers. The physiochemical properties of adsorbents influences irreversible uptakes. Sorbates differed markedly in their tendencies to undergo irreversible adsorption. 64 refs., 47 figs., 32 tabs.

  12. High pressure extraction of phenolic compounds from citrus peels†

    NASA Astrophysics Data System (ADS)

    Casquete, R.; Castro, S. M.; Villalobos, M. C.; Serradilla, M. J.; Queirós, R. P.; Saraiva, J. A.; Córdoba, M. G.; Teixeira, P.

    2014-10-01

    This study evaluated the effect of high pressure processing on the recovery of high added value compounds from citrus peels. Overall, the total phenolic content in orange peel was significantly (P < .05) higher than that in lemon peel, except when pressure treated at 500 MPa. However, lemon peel demonstrated more antioxidant activity than orange peel. Pressure-treated samples (300 MPa, 10 min; 500 MPa, 3 min) demonstrated higher phenolic content and antioxidant activity comparatively to the control samples. For more severe treatments (500 MPa, 10 min), the phenolic content and antioxidant activity decreased in both lemon and orange peels. This paper was presented at the 8th International Conference on High Pressure Bioscience & Biotechnology (HPBB 2014), in Nantes (France), 15-18 July 2014.

  13. Perlite filtration of phenolic compounds from cigarette smoke.

    PubMed

    Rostami-Charati, Faramarz; Robati, Gholamreza Moradi; Naghizadeh, Farhad; Hosseini, Shahnaz; Chaichi, Mohammad Javad

    2013-01-01

    Adsorption of phenolic compounds and chemical analysis of them from a local production cigarette (named by Farvardin cigarette) smoke have been investigated by using perlite filtration. In this research, the mainstream smoke was tested by three filtration methods: Perlite filter, Cambridge filter and general cigarette filter. Then the used filter was extracted by pure methanol as solvent. After that, the extracted solution was analysed by GC-MS. By this consideration, the phenolic derivatives such as phenol, hydroquinone, resorcinol, pyrocatechol, m-cresol, p-cresol and o-cresol were detected. The structure of the perlite filtration after absorption was studied by SEM. In addition, its chemical structure was investigated by XRD and XRF.

  14. Phenolic compounds from the leaf extract of artichoke (Cynara scolymus L.) and their antimicrobial activities.

    PubMed

    Zhu, Xianfeng; Zhang, Hongxun; Lo, Raymond

    2004-12-01

    A preliminary antimicrobial disk assay of chloroform, ethyl acetate, and n-butanol extracts of artichoke (Cynara scolymus L.) leaf extracts showed that the n-butanol fraction exhibited the most significant antimicrobial activities against seven bacteria species, four yeasts, and four molds. Eight phenolic compounds were isolated from the n-butanol soluble fraction of artichoke leaf extracts. On the basis of high-performance liquid chromatography/electrospray ionization mass spectrometry, tandem mass spectrometry, and nuclear magnetic resonance techniques, the structures of the isolated compounds were determined as the four caffeoylquinic acid derivatives, chlorogenic acid (1), cynarin (2), 3,5-di-O-caffeoylquinic acid (3), and 4,5-di-O-caffeoylquinic acid (4), and the four flavonoids, luteolin-7-rutinoside (5), cynaroside (6), apigenin-7-rutinoside (7), and apigenin-7-O-beta-D-glucopyranoside (8), respectively. The isolated compounds were examined for their antimicrobial activities on the above microorganisms, indicating that all eight phenolic compounds showed activity against most of the tested organisms. Among them, chlorogenic acid, cynarin, luteolin-7-rutinoside, and cynaroside exhibited a relatively higher activity than other compounds; in addition, they were more effective against fungi than bacteria. The minimum inhibitory concentrations of these compounds were between 50 and 200 microg/mL.

  15. Aquatic pathways model to predict the fate of phenolic compounds

    SciTech Connect

    Aaberg, R.L.; Peloquin, R.A.; Strenge, D.L.; Mellinger, P.J.

    1983-04-01

    Organic materials released from energy-related activities could affect human health and the environment. To better assess possible impacts, we developed a model to predict the fate of spills or discharges of pollutants into flowing or static bodies of fresh water. A computer code, Aquatic Pathways Model (APM), was written to implement the model. The computer programs use compartmental analysis to simulate aquatic ecosystems. The APM estimates the concentrations of chemicals in fish tissue, water and sediment, and is therefore useful for assessing exposure to humans through aquatic pathways. The APM will consider any aquatic pathway for which the user has transport data. Additionally, APM will estimate transport rates from physical and chemical properties of chemicals between several key compartments. The major pathways considered are biodegradation, fish and sediment uptake, photolysis, and evaporation. The model has been implemented with parameters for distribution of phenols, an important class of compounds found in the water-soluble fractions of coal liquids. Current modeling efforts show that, in comparison with many pesticides and polyaromatic hydrocarbons (PAH), the lighter phenolics (the cresols) are not persistent in the environment. The properties of heavier molecular weight phenolics (indanols, naphthols) are not well enough understood at this time to make similar judgements. For the twelve phenolics studied, biodegradation appears to be the major pathway for elimination from aquatic environments. A pond system simulation (using APM) of a spill of solvent refined coal (SRC-II) materials indicates that phenol, cresols, and other single cyclic phenolics are degraded to 16 to 25 percent of their original concentrations within 30 hours. Adsorption of these compounds into sediments and accumulation by fish was minor.

  16. Isolation of phenolic compounds from iceberg lettuce and impact on enzymatic browning.

    PubMed

    Mai, Franziska; Glomb, Marcus A

    2013-03-20

    Enzymatic browning is generally reported as the reaction between phenolic substances and enzymes. The quality of iceberg lettuce is directly linked to this discoloration. In particular, the color change of lettuce stems considerably reduces consumer acceptance and thus decreases sales revenue of iceberg lettuce. Ten phenolic compounds (caffeic acid, chlorogenic acid, phaseolic acid, chicoric acid, isochlorogenic acid, luteolin-7-O-glucuronide, quercetin-3-O-glucuronide, quercetin-3-O-galactoside, quercetin-3-O-glucoside, and quercetin-3-O-(6″-malonyl)-glucoside) were isolated from Lactuca sativa var. capitata by multilayer countercurrent chromatography (MLCCC) and preparative high-performance liquid chromatography (HPLC). In addition, syringin was identified for the first time in iceberg lettuce. This polyphenolic ingredient was previously not mentioned for the family of Cichorieae in general. The purity and identity of isolated compounds were confirmed by different NMR experiments, HPLC-DAD-MS, and HR-MS techniques. Furthermore, the relationship between discoloration of iceberg lettuce and enzymatic browning was thoroughly investigated. Unexpectedly, the total concentration of phenolic compounds and the activity of polyphenol oxidase were not directly related to the browning processes. Results of model incubation experiments of plant extract solutions led to the conclusion that in addition to the typical enzymatic browning induced by polyphenol oxidases, further mechanisms must be involved to explain total browning of lettuce.

  17. Isolation of phenolic compounds from iceberg lettuce and impact on enzymatic browning.

    PubMed

    Mai, Franziska; Glomb, Marcus A

    2013-03-20

    Enzymatic browning is generally reported as the reaction between phenolic substances and enzymes. The quality of iceberg lettuce is directly linked to this discoloration. In particular, the color change of lettuce stems considerably reduces consumer acceptance and thus decreases sales revenue of iceberg lettuce. Ten phenolic compounds (caffeic acid, chlorogenic acid, phaseolic acid, chicoric acid, isochlorogenic acid, luteolin-7-O-glucuronide, quercetin-3-O-glucuronide, quercetin-3-O-galactoside, quercetin-3-O-glucoside, and quercetin-3-O-(6″-malonyl)-glucoside) were isolated from Lactuca sativa var. capitata by multilayer countercurrent chromatography (MLCCC) and preparative high-performance liquid chromatography (HPLC). In addition, syringin was identified for the first time in iceberg lettuce. This polyphenolic ingredient was previously not mentioned for the family of Cichorieae in general. The purity and identity of isolated compounds were confirmed by different NMR experiments, HPLC-DAD-MS, and HR-MS techniques. Furthermore, the relationship between discoloration of iceberg lettuce and enzymatic browning was thoroughly investigated. Unexpectedly, the total concentration of phenolic compounds and the activity of polyphenol oxidase were not directly related to the browning processes. Results of model incubation experiments of plant extract solutions led to the conclusion that in addition to the typical enzymatic browning induced by polyphenol oxidases, further mechanisms must be involved to explain total browning of lettuce. PMID:23473017

  18. Phenolic compounds and antioxidant capacities of 10 common edible flowers from China.

    PubMed

    Xiong, Lina; Yang, Jiajia; Jiang, Yirong; Lu, Baiyi; Hu, Yinzhou; Zhou, Fei; Mao, Shuqin; Shen, Canxi

    2014-04-01

    The free and bound phenolic compounds in 10 common Chinese edible flowers were investigated using reversed phase high-performance liquid chromatography. Their antioxidant capacities were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical-scavenging activity, oxygen radical absorption capacity (ORAC), ferric reducing antioxidant power (FRAP), and cellular antioxidant activity (CAA). Free factions were more prominent in phenolic content and antioxidant capacity than bound fractions. Paeonia suffruticosa and Flos lonicerae showed the highest total phenolic content (TPC) 235.5 mg chlorogenic acid equivalents/g of dry weight and total flavonoid content 89.38 mg rutin equivalents/g of dry weight. The major phenolic compounds identified were gallic acid, chlorogenic acid, and rutin. P. suffruticosa had the highest antioxidant capacity in the DPPH, ABTS, and ORAC assays, which were 1028, 2065, 990 μmol Trolox equivalents/g of dry weight, respectively, whereas Rosa chinensis had the highest FRAP value (2645 μmol Fe(2+) equivalents /g of dry weight). The P. suffruticosa soluble phenolics had the highest CAA, with the median effective dose (EC50 ) 26.7 and 153 μmol quercetin equivalents/100 g of dry weight in the phosphate buffered saline (PBS) and no PBS wash protocol, respectively. TPC was strongly correlated with antioxidant capacity (R = 0.8443 to 0.9978, P < 0.01), which indicated that phenolics were the major contributors to the antioxidant activity of the selected edible flowers.

  19. Flavonoids and Phenolic Acids in Methanolic Extracts, Infusions and Tinctures from Commercial Samples of Lemon Balm.

    PubMed

    Arceusz, Agnieszka; Wesolowski, Marek; Ulewicz-Magulska, Beata

    2015-06-01

    The aim of this study was to quantify the levels of flavonoids (rutin, myricetin, quercetin, kaempferol) and phenolic acids (gallic, p-coumaric, rosmarinic, syringic, caffeic, chlorogenic, ellagic, ferulic) in lemon balm (Melissa officinalis L.) commonly used as a culinary, aromatic and medicinal herb. A rapid and reliable HPLC procedure was developed to determine the phenolic compounds in methanolic extracts, infusions and tinctures prepared from lemon balm. Except for myricetin and quercetin, as well as ellagic, gallic and rosmarinic acids, higher levels of the analytes under study were determined in the methanolic extracts (up to 22 mg/g of dry weight, DW), than in infusions (up to 5 mg/g DW). Tinctures were the poorest in flavonoids and phenolic acids (below 550 μg/g DW), except for ellagic and rosmarinic acids, which were quantified in tinctures at higher levels (mg/g DW). To sum up, the flavonoids were extracted more effectively in the infusions and tinctures than the phenolic acids. Statistically significant correlations were found between phenolic acids, possibly owing to similar biochemical pathways of the compounds. The hierarchical cluster and principal component analyses have also shown that the samples of lemon balm could be differentiated based on the levels of flavonoids and phenolic acids. PMID:26197530

  20. Flavonoids and Phenolic Acids in Methanolic Extracts, Infusions and Tinctures from Commercial Samples of Lemon Balm.

    PubMed

    Arceusz, Agnieszka; Wesolowski, Marek; Ulewicz-Magulska, Beata

    2015-06-01

    The aim of this study was to quantify the levels of flavonoids (rutin, myricetin, quercetin, kaempferol) and phenolic acids (gallic, p-coumaric, rosmarinic, syringic, caffeic, chlorogenic, ellagic, ferulic) in lemon balm (Melissa officinalis L.) commonly used as a culinary, aromatic and medicinal herb. A rapid and reliable HPLC procedure was developed to determine the phenolic compounds in methanolic extracts, infusions and tinctures prepared from lemon balm. Except for myricetin and quercetin, as well as ellagic, gallic and rosmarinic acids, higher levels of the analytes under study were determined in the methanolic extracts (up to 22 mg/g of dry weight, DW), than in infusions (up to 5 mg/g DW). Tinctures were the poorest in flavonoids and phenolic acids (below 550 μg/g DW), except for ellagic and rosmarinic acids, which were quantified in tinctures at higher levels (mg/g DW). To sum up, the flavonoids were extracted more effectively in the infusions and tinctures than the phenolic acids. Statistically significant correlations were found between phenolic acids, possibly owing to similar biochemical pathways of the compounds. The hierarchical cluster and principal component analyses have also shown that the samples of lemon balm could be differentiated based on the levels of flavonoids and phenolic acids.

  1. Phenolics and betacyanins in red beetroot (Beta vulgaris) root: distribution and effect of cold storage on the content of total phenolics and three individual compounds.

    PubMed

    Kujala, T S; Loponen, J M; Klika, K D; Pihlaja, K

    2000-11-01

    The distribution of total phenolics and main betacyanins in red beetroot (Beta vulgaris) root was determined. Also, the subsequent effects of cold storage on the content of total phenolics, main betacyanins (betanin and isobetanin), and the main known ferulic acid ester (beta-D-fructofuranosyl-alpha-D-(6-O-(E)-feruloylglucopyranoside) were determined in the peel, which is the root part containing the largest amount of total phenolics. The content of total phenolics in the red beetroot water extracts was determined according to a modification of the Folin-Ciocalteu method and expressed as gallic acid equivalents (GAE). The compounds of interest were identified by HPLC-ESI-MS and NMR techniques, and the contents of compounds were determined by HLPC analyses. The total phenolic contents in various root parts were found to decrease in the order peel, crown, flesh. Significant differences in the contents of total phenolics and individual compounds were found when the effect of cold storage (5 degrees C, 0-196 days) on the constituents of the peel from intact roots was examined. In addition to the betacyanins of red beetroot peel found in our earlier study, tentative identifications of betanidin and feruloylamaranthin were made.

  2. Phenolic acid degradation potential and growth behavior of lactic acid bacteria in sunflower substrates.

    PubMed

    Fritsch, Caroline; Heinrich, Veronika; Vogel, Rudi F; Toelstede, Simone

    2016-08-01

    Sunflower flour provides a high content of protein with a well-balanced amino acid composition and is therefore regarded as an attractive source for protein. The use for human nutrition is hindered by phenolic compounds, mainly chlorogenic acid, which can lead under specific circumstances to undesirable discolorations. In this study, growth behavior and degradation ability of chlorogenic acid of four lactic acid bacteria were explored. Data suggested that significant higher fermentation performances on sunflower flour as compared to sunflower protein concentrate were reached by Lactobacillus plantarum, Pediococcus pentosaceus, Lactobacillus gasseri and Bifidobacterium animalis subsp. lactis. In fermentation with the latter two strains reduced amounts of chlorogenic acid were observed in sunflower flour (-11.4% and -19.8%, respectively), which were more pronounced in the protein concentrate (-50.7% and -95.6%, respectively). High tolerances against chlorogenic acid and the cleavage product quinic acid with a minimum inhibitory concentration (MIC) of ≥20.48 mg/ml after 48 h were recorded for all strains except Bifidobacterium animalis subsp. lactis, which was more sensitive. The second cleavage compound, caffeic acid revealed a higher antimicrobial potential with MIC values of 0.64-5.12 mg/ml. In this proof of concept study, degradation versus inhibitory effect suggest the existence of basic mechanisms of interaction between phenolic acids in sunflower and lactic acid bacteria and a feasible way to reduce the chlorogenic acid content, which may help to avoid undesired color changes.

  3. Colorimetric paper bioassay for the detection of phenolic compounds.

    PubMed

    Alkasir, Ramiz S J; Ornatska, Maryna; Andreescu, Silvana

    2012-11-20

    A new type of paper based bioassay for the colorimetric detection of phenolic compounds including phenol, bisphenol A, catechol and cresols is reported. The sensor is based on a layer-by-layer (LbL) assembly approach formed by alternatively depositing layers of chitosan and alginate polyelectrolytes onto filter paper and physically entrapping the tyrosinase enzyme in between these layers. The sensor response is quantified as a color change resulting from the specific binding of the enzymatically generated quinone to the multilayers of immobilized chitosan on the paper. The color change can be quantified with the naked eye but a digitalized picture can also be used to provide more sensitive comparison to a calibrated color scheme. The sensor was optimized with respect to the number of layers, pH, enzyme, chitosan and alginate amounts. The colorimetric response was concentration dependent, with a detection limit of 0.86 (±0.1) μg/L for each of the phenolic compounds tested. The response time required for the sensor to reach steady-state color varied between 6 and 17 min depending on the phenolic substrate. The sensor showed excellent storage stability at room temperature for several months (92% residual activity after 260 days storage) and demonstrated good functionality in real environmental samples. A procedure to mass-produce the bioactive sensors by inkjet printing the LbL layers of polyelectrolyte and enzyme on paper is demonstrated. PMID:23113670

  4. Potential of LC Coupled to Fluorescence Detection in Food Metabolomics: Determination of Phenolic Compounds in Virgin Olive Oil

    PubMed Central

    Monasterio, Romina P.; Olmo-García, Lucía; Bajoub, Aadil; Fernández-Gutiérrez, Alberto; Carrasco-Pancorbo, Alegría

    2016-01-01

    A powerful chromatographic method coupled to a fluorescence detector was developed to determine the phenolic compounds present in virgin olive oil (VOO), with the aim to propose an appropriate alternative to liquid chromatography-mass spectrometry. An excitation wavelength of 285 nm was selected and four different emission wavelengths (316, 328, 350 and 450 nm) were simultaneously recorded, working therefore on “multi-emission” detection mode. With the use of commercially available standards and other standards obtained by semipreparative high performance liquid chromatography, it was possible to identify simple phenols, lignans, several complex phenols, and other phenolic compounds present in the matrix under study. A total of 26 phenolic compounds belonging to different chemical families were identified (23 of them were susceptible of being quantified). The proposed methodology provided detection and quantification limits within the ranges of 0.004–7.143 μg·mL−1 and 0.013–23.810 μg·mL−1, respectively. As far as the repeatability is concerned, the relative standard deviation values were below 0.43% for retention time, and 9.05% for peak area. The developed methodology was applied for the determination of phenolic compounds in ten VOOs, both monovarietals and blends. Secoiridoids were the most abundant fraction in all the samples, followed by simple phenolic alcohols, lignans, flavonoids, and phenolic acids (being the abundance order of the latter chemical classes logically depending on the variety and origin of the VOOs). PMID:27669238

  5. Potential of LC Coupled to Fluorescence Detection in Food Metabolomics: Determination of Phenolic Compounds in Virgin Olive Oil.

    PubMed

    Monasterio, Romina P; Olmo-García, Lucía; Bajoub, Aadil; Fernández-Gutiérrez, Alberto; Carrasco-Pancorbo, Alegría

    2016-01-01

    A powerful chromatographic method coupled to a fluorescence detector was developed to determine the phenolic compounds present in virgin olive oil (VOO), with the aim to propose an appropriate alternative to liquid chromatography-mass spectrometry. An excitation wavelength of 285 nm was selected and four different emission wavelengths (316, 328, 350 and 450 nm) were simultaneously recorded, working therefore on "multi-emission" detection mode. With the use of commercially available standards and other standards obtained by semipreparative high performance liquid chromatography, it was possible to identify simple phenols, lignans, several complex phenols, and other phenolic compounds present in the matrix under study. A total of 26 phenolic compounds belonging to different chemical families were identified (23 of them were susceptible of being quantified). The proposed methodology provided detection and quantification limits within the ranges of 0.004-7.143 μg·mL(-1) and 0.013-23.810 μg·mL(-1), respectively. As far as the repeatability is concerned, the relative standard deviation values were below 0.43% for retention time, and 9.05% for peak area. The developed methodology was applied for the determination of phenolic compounds in ten VOOs, both monovarietals and blends. Secoiridoids were the most abundant fraction in all the samples, followed by simple phenolic alcohols, lignans, flavonoids, and phenolic acids (being the abundance order of the latter chemical classes logically depending on the variety and origin of the VOOs). PMID:27669238

  6. Development and Validation of an HPLC-UV Method for Determination of Eight Phenolic Compounds in Date Palms.

    PubMed

    Al-Rimawi, Fuad; Odeh, Imad

    2015-01-01

    A simple, precise, accurate, and selective method was developed and validated for determination of eight phenolic compounds (gallic acid, p-hydroxybenzoic acid, vanilic acid, caffeic acid, syringic acid, p-coumaric acid, ferulic acid, and sinapic acid) in date palms. Separation was achieved on an RP C18 column using the mobile phase methanol-water with 2% acetic acid (18+82, v/v). This method was validated according to the requirements for new methods, which include accuracy, precision, selectivity, robustness, LOD, LOQ, linearity, and range. The method demonstrated good linearity over the range 1-1000 ppm of gallic acid, p-hydroxybenzoic acid, vanilic acid, caffeic acid, and syringic acid with r2 greater than 0.99, and in the range of 3-1000 ppm for p-coumaric acid, ferulic acid, and sinapic acid with r2 greater than 0.99. The recovery of the eight phenolic compounds ranged from 97.1 to 102.2%. The method is selective because adjacent peaks of phenolic compounds were well separated with good resolution. The degree of reproducibility of the results obtained as a result of small deliberate variations in the method parameters and by changing analytical operators proved that the method is robust and rugged.

  7. Effects of plant antimicrobial phenolic compounds on virulence of the genus Pectobacterium.

    PubMed

    Joshi, Janak Raj; Burdman, Saul; Lipsky, Alexander; Yedidia, Iris

    2015-01-01

    Pectobacterium spp. are among the most devastating necrotrophs, attacking more than 50% of angiosperm plant orders. Their virulence strategy is based mainly on the secretion of exoenzymes that degrade the cell walls of their hosts, providing nutrients to the bacteria, but conversely, exposing the bacteria to plant defense compounds. In the present study, we screened plant-derived antimicrobial compounds, mainly phenolic acids and polyphenols, for their ability to affect virulence determinants including motility, biofilm formation and extracellular enzyme activities of different Pectobacteria: Pectobacterium carotovorum, P. brasiliensis, P. atrosepticum and P. aroidearum. In addition, virulence assays were performed on three different plant hosts following exposure of the bacteria to selected phenolic compounds. These experiments showed that cinnamic, coumaric, syringic and salicylic acids and catechol can considerably reduce disease severity, ranging from 20 to 100%. The reduced disease severity was not only the result of reduced bacterial growth, but also of a direct effect of the compounds on important bacterial virulence determinants, including pectolytic and proteolytic exoenzyme activities, that were reduced by 50-100%. This is the first report revealing a direct effect of phenolic compounds on virulence factors in a wide range of Pectobacterium strains.

  8. Evolution of colour and phenolic compounds during Garnacha Tintorera grape raisining.

    PubMed

    Figueiredo-González, M; Cancho-Grande, B; Simal-Gándara, J

    2013-12-01

    The off-vine drying is one of the most important steps in the production of a high quality naturally sweet wine. However, only few studies have analyzed the changes in colour and phenolic compounds of the grapes throughout the process. In this work, UV/Vis spectrophotometry and HPLC/DAD-ESI/MS were applied to determine, respectively, the evolution of colour and phenolic compounds in the red grapes of Garnacha Tintorera during the raisining process. The total water loss in 83 days was about 62% and the sugar concentration rose from 225 to 464 g L(-1). Browning and low-medium molecular weight compounds increase during the dehydration process. In CIELab coordinates, raisining decreases a(*) (red/green) and lightness and increases b(∗) (yellow/blue), colour saturation and hue angle. In general, most of the phenolic compounds determined (anthocyanins, flavonols, esters of hydroxycinnamic acids, flavan-3-ol monomers and proanthocyanidins) increase but to a lesser extent than expected because of the water loss of the grapes during drying. The lower increase was observed for esters of hydroxicinnamic acids suggesting these compounds could undergo strong enzymatic degradation. Despite this, both the terminal and the extension subunit compositions show little changes, while the mean degree of polymerization of proanthocyanidins decreases as raisining progresses.

  9. Evolution of colour and phenolic compounds during Garnacha Tintorera grape raisining.

    PubMed

    Figueiredo-González, M; Cancho-Grande, B; Simal-Gándara, J

    2013-12-01

    The off-vine drying is one of the most important steps in the production of a high quality naturally sweet wine. However, only few studies have analyzed the changes in colour and phenolic compounds of the grapes throughout the process. In this work, UV/Vis spectrophotometry and HPLC/DAD-ESI/MS were applied to determine, respectively, the evolution of colour and phenolic compounds in the red grapes of Garnacha Tintorera during the raisining process. The total water loss in 83 days was about 62% and the sugar concentration rose from 225 to 464 g L(-1). Browning and low-medium molecular weight compounds increase during the dehydration process. In CIELab coordinates, raisining decreases a(*) (red/green) and lightness and increases b(∗) (yellow/blue), colour saturation and hue angle. In general, most of the phenolic compounds determined (anthocyanins, flavonols, esters of hydroxycinnamic acids, flavan-3-ol monomers and proanthocyanidins) increase but to a lesser extent than expected because of the water loss of the grapes during drying. The lower increase was observed for esters of hydroxicinnamic acids suggesting these compounds could undergo strong enzymatic degradation. Despite this, both the terminal and the extension subunit compositions show little changes, while the mean degree of polymerization of proanthocyanidins decreases as raisining progresses. PMID:23871082

  10. Inhibitory Effect of Furanic and Phenolic Compounds on Exoelectrogenesis in a Microbial Electrolysis Cell Bioanode

    DOE PAGES

    Zeng, Xiaofei; Borole, Abhijeet P.; Pavlostathis, Spyros G.

    2016-09-09

    Furanic and phenolic compounds are 20 lignocellulose-derived compounds known to inhibit to H2- and ethanol- producing microorganisms in dark fermentation. Bioelectrochemical conversion of furanic and phenolic compounds to electricity or H2 has recently been demonstrated as a productive method to use these compounds. However, potential inhibitory effect of furanic and phenolic compounds on exoelectrogenesis in bioelectrochemical systems is not well understood. This study systematically investigated the inhibitory effect of furfural (FF), 5-hydroxymethylfurfural (HMF), syringic acid (SA), vanillic acid (VA), and 4-hydroxybenzoic acid (HBA) on exoelectrogenesis in the bioanode of a microbial electrolysis cell. A mixture of these five compounds atmore » an increasing initial total concentration from 0.8 to 8.0 g/L resulted in current decrease up to 91%. The observed inhibition primarily affected exoelectrogenesis, instead of non-exoelectrogenic biotransformation pathways (e.g., fermentation) of the five compounds. Furthermore, the parent compounds at a high concentration, as opposed to their biotransformation products, were responsible for the observed inhibition. Tests with individual compounds show that all five parent compounds contributed to the observed inhibition by the mixture. The IC50 (concentration resulting in 50% current decrease) was estimated as 2.7 g/L for FF, 3.0 g/L for HMF, 1.9 g/L for SA, 2.1 g/L for VA and 2.0 g/L for HBA. Nevertheless, these compounds below their non-inhibitory concentrations jointly resulted in significant inhibition as a mixture. Catechol and phenol, which were persistent biotransformation products of the mixture, inhibited exoelectrogens at high concentrations, but to a lesser extent than the parent compounds. Recovery of exoelectrogenesis from inhibition by all compounds was observed, except for catechol, which resulted in irreversible inhibition. The reversibility of inhibition, as well as the observed difference in recovery

  11. Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity

    PubMed Central

    Ihssen, Julian; Schubert, Mark; Thöny-Meyer, Linda; Richter, Michael

    2014-01-01

    Iodine is a well known antimicrobial compound. Laccase, an oxidoreductase which couples the one electron oxidation of diverse phenolic and non-phenolic substrates to the reduction of oxygen to water, is capable of oxidizing unreactive iodide to reactive iodine. We have shown previously that laccase-iodide treatment of spruce wood results in a wash-out resistant antimicrobial surface. In this study, we investigated whether phenolic compounds such as vanillin, which resembles sub-structures of softwood lignin, can be directly iodinated by reacting with laccase and iodide, resulting in compounds with antifungal activity. HPLC-MS analysis showed that vanillin was converted to iodovanillin by laccase catalysis at an excess of potassium iodide. No conversion of vanillin occurred in the absence of enzyme. The addition of redox mediators in catalytic concentrations increased the rate of iodide oxidation ten-fold and the yield of iodovanillin by 50%. Iodinated phenolic products were also detected when o-vanillin, ethyl vanillin, acetovanillone and methyl vanillate were incubated with laccase and iodide. At an increased educt concentration of 0.1 M an almost one to one molar ratio of iodide to vanillin could be used without compromising conversion rate, and the insoluble iodovanillin product could be recovered by simple centrifugation. The novel enzymatic synthesis procedure fulfills key criteria of green chemistry. Biocatalytically produced iodovanillin and iodo-ethyl vanillin had significant growth inhibitory effects on several wood degrading fungal species. For Trametes versicolor, a species causing white rot of wood, almost complete growth inhibition and a partial biocidal effect was observed on agar plates. Enzymatic tests indicated that the iodinated compounds acted as enzyme responsive, antimicrobial materials. PMID:24594755

  12. Immobilized soybean hull peroxidase for the oxidation of phenolic compounds in coffee processing wastewater.

    PubMed

    Chagas, Pricila Maria Batista; Torres, Juliana Arriel; Silva, Maria Cristina; Corrêa, Angelita Duarte

    2015-11-01

    Chitosan beads were prepared, using glutaraldehyde as a crosslinking agent for the immobilization of soybean hull peroxidase (SBP). The activity of free and immobilized SBP was studied. The optimum pH was 6.0 for both the free and immobilized enzyme; however, enzyme activity became more dependent on the temperature after immobilization. This study evaluated the potential use of immobilized and free enzyme in the oxidation of caffeic acid, of synthetic phenolic solution (SPS) and of total phenolic compounds in coffee processing wastewater (CPW). Some factors, such as reaction time, amount of H2O2 and caffeic acid were evaluated, in order to determine the optimum conditions for enzyme performance. Both enzymes showed a potential in the removal of caffeic acid, SPS and CPW, and immobilized SBP had the highest oxidation performance. The immobilized enzyme showed a potential of 50% in the oxidation of caffeic acid after 4 consecutive cycles.

  13. Phenolic Compounds from the Flowers of Bombax malabaricum and Their Antioxidant and Antiviral Activities.

    PubMed

    Zhang, Yu-Bo; Wu, Peng; Zhang, Xiao-Li; Xia, Chao; Li, Guo-Qiang; Ye, Wen-Cai; Wang, Guo-Cai; Li, Yao-Lan

    2015-11-05

    Three new phenolic compounds 1-3 and twenty known ones 4-23 were isolated from the flowers of Bombax malabaricum. Their chemical structures were elucidated by spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D- and 2D-NMR) and chemical reactions. The antioxidant capacities of the isolated compounds were tested using FRAP and DPPH radical-scavenging assays, and compounds 4, 6, 8, 12, as well as the new compound 2, exhibited stronger antioxidant activities than ascorbic acid. Furthermore, all of compounds were tested for their antiviral activities against RSV by the CPE reduction assay and plaque reduction assay. Compounds 4, 10, 12 possess in vitro antiviral activities, and compound 10 exhibits potent anti-RSV effects, comparable to the positive control ribavirin.

  14. Competitive adsorption of phenolic compounds from aqueous solution using sludge-based activated carbon.

    PubMed

    Mohamed, E F; Andriantsiferana, C; Wilhelm, A M; Delmas, H

    2011-01-01

    Preparation of activated carbon from sewage sludge is a promising approach to produce cheap and efficient adsorbent for pollutants removal as well as to dispose of sewage sludge. The first objective of this study was to investigate the physical and chemical properties (BET surface area, ash and elemental content, surface functional groups by Boehm titration and weight loss by thermogravimetric analysis) of the sludge-based activated carbon (SBAC) so as to give a basic understanding of its structure and to compare to those of two commercial activated carbons, PICA S23 and F22. The second and main objective was to evaluate the performance of SBAC for single and competitive adsorption of four substituted phenols (p-nitrophenol, p-chlorophenol, p-hydroxy benzoic acid and phenol) from their aqueous solutions. The results indicated that, despite moderate micropore and mesopore surface areas, SBAC had remarkable adsorption capacity for phenols, though less than PICA carbons. Uptake of the phenolic compound was found to be dependent on both the porosity and surface chemistry of the carbons. Furthermore, the electronegativity and the hydrophobicity of the adsorbate have significant influence on the adsorption capacity. The Langmuir and Freundlich models were used for the mathematical description of the adsorption equilibrium for single-solute isotherms. Moreover, the Langmuir-Freundlich model gave satisfactory results for describing multicomponent system isotherms. The capacity of the studied activated carbons to adsorb phenols from a multi-solute system was in the following order: p-nitrophenol > p-chlorophenol > PHBA > phenol.

  15. Cold water fish gelatin modification by a natural phenolic cross-linker (ferulic acid and caffeic acid)

    PubMed Central

    Araghi, Maryam; Moslehi, Zeinab; Mohammadi Nafchi, Abdorreza; Mostahsan, Amir; Salamat, Nima; Daraei Garmakhany, Amir

    2015-01-01

    Nowadays use of edible films and coatings is increasing due to their biodegradability and environment friendly properties. Fish gelatin obtained from fish skin wastage can be used as an appropriate protein compound for replacing pork gelatin to produce edible film. In this study films were prepared by combination of fish gelatin and different concentration (0%, 1%, 3%, and 5%) of two phenolic compounds (caffeic acid and ferulic acid). The film was prepared at pH > 10 and temperature of 60˚c under continuous injection of O2 and addition of the plasticizer sorbitol/glycerol. Results showed that solubility, oxygen permeability, and water vapor permeability were decreased for caffeic acid and the highest effect was observed at concentration of 5%. Solubility had a linear relationship with concentration of phenolic compound in film containing ferulic acid, however, no significant change was observed in vapor and O2 permeability. A comparison between two phenolic compounds showed that caffeic acid had the highest effect in decreasing solubility, water vapor permeability, and oxygen permeability. Caffeic acid is more effective phenolic compound compared with Ferulic acid that can increase safety of biodegradable packaging by improving their barrier and physicochemical properties. PMID:26405523

  16. Flavonoids, Phenolic Acids and Coumarins from the Roots of Althaea officinalis.

    PubMed

    Gudej, J

    1991-06-01

    From the roots of ALTHAEA OFFICINALIS two flavonoid glycosides were separated. Phenolic acids and coumarins were investigated chromatographically. The structures of the compounds were established on the basis of acid hydrolysis and spectroscopic methods (UV, (1)H-NMR, (13)C-NMR) as hypolaetin 8-glucoside and the new flavonoid sulphate - isoscutellarein 4'-methyl ether 8-glucoside-2''-SO (3)K.

  17. Effect of steam explosion treatment on barley bran phenolic compounds and antioxidant capacity.

    PubMed

    Gong, Lingxiao; Huang, Luolian; Zhang, Ying

    2012-07-25

    A steam explosion pretreatment process followed by methanol extraction has been applied for releasing and extracting phenolic compounds, as well as other effective components, from barley bran. The steam explosion treatment was performed at different temperatures ranging from 210 to 250 °C, with a residence time of 30 s. The effect of residence time was also studied in the range 10 s to 120 s at 220 °C. The extracts were evaluated for their total soluble phenolic content (TSPC) including total free phenolic acids (TFPC) and total soluble conjugates (TSC), identified phenolic acids, total antioxidant capacity (TAC), water-soluble carbohydrates (WSC) and total methanol extracts (TME). High-performance liquid chromatography (HPLC) coupled with a photodiode array detector (PDA) was used in this study for the analysis of p-coumaric acid and ferulic acid in barley bran before and after steam explosion. Our results indicate that TSPC and TAC increased with residence time. They also increased dramatically with temperature up to 220 °C. After steam explosion at 220 °C for 120 s, the TSPC reached 1686.4 gallic acid equivalents mg/100 g dry weight, which was about 9-fold higher than that of the untreated sample. The TSPC and TAC obtained were highly positively correlated (r = 0.918-0.993), which meant that the increase of TAC for the steam explosion pretreated barley bran extracts was due, at least in part, to the increase of TSPC in the methanol soluble fraction. Also, under optimum conditions, the WSC in aqueous solution was 5 times as much as that of the untreated sample, which demonstrated that steam explosion also hydrolyzes carbohydrates into water-soluble sugars. It can be concluded that a proper and reasonable steam explosion pretreatment could be applied to release the bound phenolic compounds and enhance the antioxidant capacity of barley bran extracts.

  18. Enzyme-Enhanced Extraction of Phenolic Compounds and Proteins from Flaxseed Meal

    PubMed Central

    Ribeiro, Bernardo Dias; Barreto, Daniel Weingart; Coelho, Maria Alice Zarur

    2013-01-01

    Flaxseed (Linum usitatissimum) meal, the main byproduct of the flaxseed oil extraction process, is composed mainly of proteins, mucilage, and phenolic compounds. The extraction methods of phenolics either commonly employed the use of mixed solvents (dioxane/ethanol, water/acetone, water/methanol, and water/ethanol) or are done with the aid of alkaline, acid, or enzymatic hydrolysis. This work aimed at the study of optimal conditions for a clean process, using renewable solvents and enzymes, for the extraction of phenolics and proteins from flaxseed meal. After a screening of the most promising commercial preparations based on different carbohydrases and proteases, a central composite rotatable design and a mixture design were applied, achieving as optimal results a solution containing 6.6 and 152 g kg−1 meal of phenolics and proteins, respectively. The statistical approach used in the present study for the enzyme-enhanced extraction of phenolics and proteins from the major flaxseed byproduct was effective. By means of the sequential experimental design methodology, the extraction of such compounds was increased 10-fold and 14-fold, when compared to a conventional nonenzymatic extraction. PMID:25969774

  19. Chemoselective esterification of phenolic acids and alcohols.

    PubMed

    Appendino, Giovanni; Minassi, Alberto; Daddario, Nives; Bianchi, Federica; Tron, Gian Cesare

    2002-10-31

    [formula: see text] The Mitsunobu reaction can distinguish between alcohol and phenol hydroxyls in esterification reactions, providing an expeditious and broadly applicable entry into various phenolics and polyphenolics of biomedical and nutritional relevance.

  20. Rice antioxidants: phenolic acids, flavonoids, anthocyanins, proanthocyanidins, tocopherols, tocotrienols, γ-oryzanol, and phytic acid

    PubMed Central

    Goufo, Piebiep; Trindade, Henrique

    2014-01-01

    Epidemiological studies suggested that the low incidence of certain chronic diseases in rice-consuming regions of the world might be associated with the antioxidant compound contents of rice. The molecules with antioxidant activity contained in rice include phenolic acids, flavonoids, anthocyanins, proanthocyanidins, tocopherols, tocotrienols, γ-oryzanol, and phytic acid. This review provides information on the contents of these compounds in rice using a food composition database built from compiling data from 316 papers. The database provides access to information that would have otherwise remained hidden in the literature. For example, among the four types of rice ranked by color, black rice varieties emerged as those exhibiting the highest antioxidant activities, followed by purple, red, and brown rice varieties. Furthermore, insoluble compounds appear to constitute the major fraction of phenolic acids and proanthocyanidins in rice, but not of flavonoids and anthocyanins. It is clear that to maximize the intake of antioxidant compounds, rice should be preferentially consumed in the form of bran or as whole grain. With respect to breeding, japonica rice varieties were found to be richer in antioxidant compounds compared with indica rice varieties. Overall, rice grain fractions appear to be rich sources of antioxidant compounds. However, on a whole grain basis and with the exception of γ-oryzanol and anthocyanins, the contents of antioxidants in other cereals appear to be higher than those in rice. PMID:24804068

  1. Phenolic acids, hydrolyzable tannins, and antioxidant activity of geopropolis from the stingless bee Melipona fasciculata Smith.

    PubMed

    Dutra, Richard Pereira; Abreu, Bruno Vinicius de Barros; Cunha, Mayara Soares; Batista, Marisa Cristina Aranha; Torres, Luce Maria Brandão; Nascimento, Flavia Raquel Fernandes; Ribeiro, Maria Nilce Sousa; Guerra, Rosane Nassar Meireles

    2014-03-26

    Geopropolis is a mixture of plant resins, waxes, and soil produced by the stingless bee Melipona fasciculata Smith. This paper describes the antioxidant activity and chemical composition of geopropolis produced by M. fasciculata. The total phenolic content determined with the Folin-Ciocalteu reagent was highest in the ethyl acetate fraction and hydroalcoholic extract. Antioxidant activity was assayed by the in vitro DPPH, ABTS, and FRAP assays. The hydroalcoholic extract and fractions of geopropolis, except for the hexane fraction, exhibited antioxidant activity against DPPH, ABTS, and FRAP. The phenolic compounds were identified by HPLC-DAD-MS on the basis of the evaluation of their UV-vis absorption maxima (λmax) and mass spectral analysis. Eleven compounds belonging to the classes of phenolic acids and hydrolyzable tannins (gallotannins and ellagitannins) were tentatively identified. These compounds are responsible for the antioxidant activity and high phenolic content of geopropolis produced by M. fasciculata.

  2. Two-dimensional liquid chromatography (LC) of phenolic compounds from the shoots of Rubus idaeus 'Glen Ample' cultivar variety.

    PubMed

    Kula, Marta; Głód, Daniel; Krauze-Baranowska, Mirosława

    2016-03-20

    In this study the application of two-dimensional LC (2D LC) for qualitative analysis of polyphenols and simple phenols in the shoots of Rubus idaeus 'Glen Ample' variety is presented. In the preliminary analysis, the methanol extract of the shoots was analyzed by one-dimensional LC. One-dimensional LC separation profiles of phenolics from R. idaeus 'Glen Ample' shoots were dependent on column type, mobile phase composition and gradient program used. Two-dimensional LC system was built from connecting an octadecyl C-18 silica column in the first dimension and pentafluorophenyl column in the second dimension, coupled with DAD and MS (ESI, APCI, DUIS ionization) detectors. A total of 34 phenolic compounds belonging to the groups of phenolic acids, ellagitannins, flavan-3-ols, flavonols and ellagic acid conjugates were identified in the shoots of R. idaeus 'Glen Ample'. The established 2D LC method offers an effective tool for analysis of phenolics present in Rubus species. PMID:26799975

  3. Characterization of phenols biodegradation by compound specific stable isotope analysis

    NASA Astrophysics Data System (ADS)

    Wei, Xi; Gilevska, Tetyana; Wenzig, Felix; Hans, Richnow; Vogt, Carsten

    2015-04-01

    Biodegradation of phenol and alkylphenols has been described under both oxic and anoxic conditions. In the absence of molecular oxygen, the degradation of phenolic compounds is initiated by microorganisms through carboxylation, fumarate addition to the methyl moiety or anoxic hydroxylation of the methyl moiety. Comparatively, under aerobic condition, the initiation mechanisms are revealed to be monoxygenation or dihydroxylation for phenol and ring hydroxylation or methyl group oxidation for cresols. While several studies biochemically characterized the enzymes and reaction mechanisms in the relevant degradation pathways, isotope fractionation patterns were rarely reported possibly due to constraints in current analytical methods. In this study, the carbon isotope fractionation patterns upon the degradation of phenol and cresols by several strains were analyzed by using isotope ratio mass spectrometry connected with liquid chromatography (LC-IRMS). The corresponding enrichment factors for carbon (ƐC) have been obtained. Cresols degradation by various strains showed generally moderate carbon isotope fractionation patterns with notable differences. For p-cresol degradation, five strains were examined. The aerobic strain Acinetobacter calcoaceticus NCIMB8250 exploits ring hydroxylation by molecular oxygen as initial reaction, and a ƐC value of -1.4±0.2‰ was obtained. Pseudomonas pseudoalcaligenes NCIMB 9867, an aerobic strain initiating cresols degradation via oxygen-dependent side chain hydroxylation, yielded a ƐC value of -2.3±0.2‰. Under nitrate-reducing conditions, Geobacter metallireducens DSM 7210 and Azoarcus buckelii DSM 14744 attacks p-cresol at the side chain by monohydroxylation using water as oxygen source; the two strains produced ƐC values of -3.6±0.4‰ and -2±0.1‰, accordingly. The sulfate-reducing Desulfosarcina cetonica DSM 7267 activating cresols by fumarate addition to the methyl moiety yielded ƐC values of -1.9±0.2‰ for p

  4. Phenolic compounds protect HepG2 cells from oxidative damage: relevance of glutathione levels.

    PubMed

    Lima, Cristovao F; Fernandes-Ferreira, Manuel; Pereira-Wilson, Cristina

    2006-10-19

    In the present work, the potential hepatoprotective effects of five phenolic compounds against oxidative damages induced by tert-butyl hydroperoxide (t-BHP) were evaluated in HepG2 cells in order to relate in vitro antioxidant activity with cytoprotective effects. t-BHP induced considerable cell damage in HepG2 cells as shown by significant LDH leakage, increased lipid peroxidation, DNA damage as well as decreased levels of reduced glutathione (GSH). All tested phenolic compounds significantly decreased cell death induced by t-BHP (when in co-incubation). If the effects of quercetin are given the reference value 1, the compounds rank in the following order according to inhibition of cell death: luteolin (4.0) > quercetin (1.0) > rosmarinic acid (0.34) > luteolin-7-glucoside (0.30) > caffeic acid (0.21). The results underscore the importance of the compound's lipophilicity in addition to its antioxidant potential for its biological activity. All tested phenolic compounds were found to significantly decrease lipid peroxidation and prevent GSH depletion induced by t-BHP, but only luteolin and quercetin significantly decreased DNA damage. Therefore, the lipophilicity of the natural antioxidants tested appeared to be of even greater importance for DNA protection than for cell survival. The protective potential against cell death was probably achieved mainly by preventing intracellular GSH depletion. The phenolic compounds studied here showed protective potential against oxidative damage induced in HepG2 cells. This could be beneficial against liver diseases where it is known that oxidative stress plays a crucial role. PMID:16857214

  5. Human fecal water inhibits COX-2 in colonic HT-29 cells: role of phenolic compounds.

    PubMed

    Karlsson, Pernilla C; Huss, Ulrika; Jenner, Andrew; Halliwell, Barry; Bohlin, Lars; Rafter, Joseph J

    2005-10-01

    The inducible enzyme cyclooxygenase-2 (COX-2) plays a major role in the regulation of inflammation and possibly in the development of colon cancer. The aim of the present study was to screen for COX-2 inhibitors in samples of fecal water (the aqueous phase of feces) and investigate whether phenolic compounds are responsible for any observed effects on COX-2. Volunteers (n = 20) were recruited and asked to supply a 24-h stool sample. Fecal water samples were prepared and analyzed by GC-MS for their content of phenolic compounds. These samples were also evaluated for their effects on COX-2 protein levels (Western blot) and prostaglandin (PG)E2 production in tumor necrosis-alpha-stimulated HT-29 cells and pure enzymatic activity in a COX-2-catalyzed prostaglandin biosynthesis in vitro assay. The major phenolic compounds identified were phenylpropionic acid, phenylacetic acid, cinnamic acid, and benzoic acid derivatives. Of 13 fecal water samples analyzed, 12 significantly decreased PGE2 production (range 5.4-39.7% inhibition, P-value < 0.05) compared with control cells and 13 of 14 samples analyzed decreased COX-2 protein levels in HT-29 cells (19-63% inhibition). Of the 20 fecal water samples, 2 also weakly inhibited enzymatic activity of purified COX-2 (22-24% inhibition). Three compounds identified in fecal water, 3-phenylpropionic acid, 3-hydroxyphenylacetic acid, and 3-(4-hydroxyphenyl)-propionic acid, decreased the protein level at 250 micromol/L (15-62% inhibition). This study shows for the first time that human fecal water contains components that can affect both the COX-2 protein level and enzymatic activity. PMID:16177193

  6. Nutritional composition and antioxidant capacity in edible flowers: characterisation of phenolic compounds by HPLC-DAD-ESI/MSn.

    PubMed

    Navarro-González, Inmaculada; González-Barrio, Rocío; García-Valverde, Verónica; Bautista-Ortín, Ana Belén; Periago, María Jesús

    2015-01-01

    Edible flowers are commonly used in human nutrition and their consumption has increased in recent years. The aim of this study was to ascertain the nutritional composition and the content and profile of phenolic compounds of three edible flowers, monks cress (Tropaeolum majus), marigold (Tagetes erecta) and paracress (Spilanthes oleracea), and to determine the relationship between the presence of phenolic compounds and the antioxidant capacity. Proximate composition, total dietary fibre (TDF) and minerals were analysed according to official methods: total phenolic compounds (TPC) were determined with Folin-Ciocalteu's reagent, whereas antioxidant capacity was evaluated using Trolox Equivalent Antioxidant Capacity (TEAC) and Oxygen Radical Absorbance Capacity (ORAC) assays. In addition, phenolic compounds were characterised by HPLC-DAD-MSn. In relation to the nutritional value, the edible flowers had a composition similar to that of other plant foods, with a high water and TDF content, low protein content and very low proportion of total fat-showing significant differences among samples. The levels of TPC compounds and the antioxidant capacity were significantly higher in T. erecta, followed by S. oleracea and T. majus. Thirty-nine different phenolic compounds were tentatively identified, with flavonols being the major compounds detected in all samples, followed by anthocyanins and hydroxycynnamic acid derivatives. In T. erecta small proportions of gallotannin and ellagic acid were also identified. PMID:25561232

  7. Nutritional Composition and Antioxidant Capacity in Edible Flowers: Characterisation of Phenolic Compounds by HPLC-DAD-ESI/MSn

    PubMed Central

    Navarro-González, Inmaculada; González-Barrio, Rocío; García-Valverde, Verónica; Bautista-Ortín, Ana Belén; Periago, María Jesús

    2014-01-01

    Edible flowers are commonly used in human nutrition and their consumption has increased in recent years. The aim of this study was to ascertain the nutritional composition and the content and profile of phenolic compounds of three edible flowers, monks cress (Tropaeolum majus), marigold (Tagetes erecta) and paracress (Spilanthes oleracea), and to determine the relationship between the presence of phenolic compounds and the antioxidant capacity. Proximate composition, total dietary fibre (TDF) and minerals were analysed according to official methods: total phenolic compounds (TPC) were determined with Folin-Ciocalteu’s reagent, whereas antioxidant capacity was evaluated using Trolox Equivalent Antioxidant Capacity (TEAC) and Oxygen Radical Absorbance Capacity (ORAC) assays. In addition, phenolic compounds were characterised by HPLC-DAD-MSn. In relation to the nutritional value, the edible flowers had a composition similar to that of other plant foods, with a high water and TDF content, low protein content and very low proportion of total fat—showing significant differences among samples. The levels of TPC compounds and the antioxidant capacity were significantly higher in T. erecta, followed by S. oleracea and T. majus. Thirty-nine different phenolic compounds were tentatively identified, with flavonols being the major compounds detected in all samples, followed by anthocyanins and hydroxycynnamic acid derivatives. In T. erecta small proportions of gallotannin and ellagic acid were also identified. PMID:25561232

  8. Nutritional composition and antioxidant capacity in edible flowers: characterisation of phenolic compounds by HPLC-DAD-ESI/MSn.

    PubMed

    Navarro-González, Inmaculada; González-Barrio, Rocío; García-Valverde, Verónica; Bautista-Ortín, Ana Belén; Periago, María Jesús

    2015-01-01

    Edible flowers are commonly used in human nutrition and their consumption has increased in recent years. The aim of this study was to ascertain the nutritional composition and the content and profile of phenolic compounds of three edible flowers, monks cress (Tropaeolum majus), marigold (Tagetes erecta) and paracress (Spilanthes oleracea), and to determine the relationship between the presence of phenolic compounds and the antioxidant capacity. Proximate composition, total dietary fibre (TDF) and minerals were analysed according to official methods: total phenolic compounds (TPC) were determined with Folin-Ciocalteu's reagent, whereas antioxidant capacity was evaluated using Trolox Equivalent Antioxidant Capacity (TEAC) and Oxygen Radical Absorbance Capacity (ORAC) assays. In addition, phenolic compounds were characterised by HPLC-DAD-MSn. In relation to the nutritional value, the edible flowers had a composition similar to that of other plant foods, with a high water and TDF content, low protein content and very low proportion of total fat-showing significant differences among samples. The levels of TPC compounds and the antioxidant capacity were significantly higher in T. erecta, followed by S. oleracea and T. majus. Thirty-nine different phenolic compounds were tentatively identified, with flavonols being the major compounds detected in all samples, followed by anthocyanins and hydroxycynnamic acid derivatives. In T. erecta small proportions of gallotannin and ellagic acid were also identified.

  9. Phenolic compounds from Byrsonima crassifolia L. bark: phytochemical investigation and quantitative analysis by LC-ESI MS/MS.

    PubMed

    Maldini, Mariateresa; Montoro, Paola; Pizza, Cosimo

    2011-08-25

    Phytochemical investigation of the methanolic extract of Byrsonima crassifolia's bark led to the isolation of 8 known phenolic compounds 5-O-galloylquinic acid, 3-O-galloylquinic acid, 3,4-di-O-galloylquinic acid, 3,5-di-O-galloylquinic acid, 3,4,5-tri-O-galloylquinic acid, (+)-epicatechin-3-gallate along with (+)-catechin and (+)-epicatechin. Due to their biological value, in the present study, a high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) method, working in multiple reaction monitoring (MRM) mode, has been developed to quantify these compounds. B. crassifolia bark resulted in a rich source of phenolic compounds and particularly of galloyl derivates. The proposed analytical method is promising to be applied to other galloyl derivatives to quantify these bioactive compounds in raw material and final products.

  10. Transport of phenolic compounds from leaf surface of creosotebush and tarbush to soil surface by precipitation.

    PubMed

    Hyder, P W; Fredrickson, E L; Estell, R E; Lucero, M E

    2002-12-01

    During the last 100 years, many desert grasslands have been replaced by shrublands. One possible mechanism by which shrubs outcompete grasses is through the release of compounds that interfere with neighboring plants. Our objective was to examine the movement of secondary compounds from the leaf surface of creosotebush and tarbush to surrounding soil surfaces via precipitation. Units consisting of a funnel and bottle were used to collect stemflow, throughfall, and interspace precipitation samples from 20 creosotebush (two morphotypes) and 10 tarbush plants during three summer rainfall events in 1998. Precipitation samples were analyzed for total phenolics (both species) and nordihydroguaiaretic acid (creosotebush only). Phenolics were detected in throughfall and stemflow of both species with stemflow containing greater concentrations than throughfall (0.088 and 0.086 mg/ml for stemflow and 0.022 and 0.014 mg/ml for throughfall in creosotebush morphotypes U and V, respectively: 0.044 and 0.006 mg/ml for tarbush stemflow and throughfall, respectively). Nordihydroguaiaretic acid was not found in any precipitation collections. The results show that phenolic compounds produced by creosotebush and tarbush can be transported to the soil surface by precipitation, but whether concentrations are ecologically significant is uncertain. Nordihydroguaiaretic acid was not present in the runoff from creosotebush.

  11. Microwave-assisted autohydrolysis of Prunus mume stone for extraction of polysaccharides and phenolic compounds.

    PubMed

    Tsubaki, S; Ozaki, Y; Azuma, J

    2010-03-01

    Stone of Prunus mume (P. mume) is a by-product of pickled P. mume industry. Stones of native and pickled P. mume, mainly composed of holocellulose (83.8 +/- 1.8% and 65.1 +/- 0.3%, respectively) and acid-insoluble lignin (25.3 +/- 2.2% and 30.6 +/- 0.9%, respectively), were autohydrolyzed by microwave heating to extract polysaccharides and phenolic compounds. By heating at 200 to 230 degrees C, 48.0% to 60.8% of polysaccharide and 84.1% to 97.9% of phenolic compound were extracted in water along with partial degradation of hemicelluloses and lignin. The extracted liquors showed antioxidant activity against hydroxyl radical and DPPH radical originated from phenolic compounds. The pickled P. mume stone showed higher autohydrolyzability and microwave absorption capacity than the native stone due to absorbed salts and acids during pickling in fruit juice of P. mume with external addition of sodium chloride. Pickling process in salty and weak acidic juice seemed to be a kind of pretreatment for softening the stones prior to autohydrolysis induced by microwave heating. PMID:20492219

  12. Oil composition and characterisation of phenolic compounds of Opuntia ficus-indica seeds.

    PubMed

    Chougui, Nadia; Tamendjari, Abderezak; Hamidj, Wahiba; Hallal, Salima; Barras, Alexandre; Richard, Tristan; Larbat, Romain

    2013-08-15

    The seed composition of four varieties of Opuntia ficus-indica growing in Algeria was investigated. Seeds ground into a fine powder were first, subjected to oil extraction and fatty acids analysis. The phenolic compounds were then extracted from the defatted powder of seeds in order to be quantified and characterised by liquid chromatography coupled to mass spectrometry (LC-MS(n)) and to nuclear magnetic resonance (LC-NMR) approaches. In addition, an evaluation of the antioxidant activity of the phenolic extracts was investigated. Gas chromatography analysis of the seed oil showed high percentages of linoleic acid in the four varieties ranging from 58% to 63%. The phenolic profile of the Opuntia ficus-indica seeds displayed a high complexity, with more than 20 compounds detected at 330 nm after the LC separation. Among them, three isomers of feruloyl-sucrose were firmly identified and another was strongly supposed to be a sinapoyl-diglycoside. High correlations were found between phenolic content in the defatted seed extracts and their antioxidant activity. The data indicate that the defatted cactus seed wastes still contain various components that constitute a source for natural foods.

  13. Antibacterial Activity and Membrane-Disruptive Mechanism of 3-p-trans-Coumaroyl-2-hydroxyquinic Acid, a Novel Phenolic Compound from Pine Needles of Cedrus deodara, against Staphylococcus aureus.

    PubMed

    Wu, Yanping; Bai, Jinrong; Zhong, Kai; Huang, Yina; Qi, Huayi; Jiang, Yan; Gao, Hong

    2016-01-01

    Recently, we reported that a novel phenolic compound isolated from Cedrus deodara, 3-p-trans-coumaroyl-2-hydroxyquinic acid (CHQA), exhibits a potent antioxidant activity. The present study aimed to evaluate the antibacterial activity of CHQA against eleven food-borne pathogens and to elucidate its mechanism of action against Staphylococcus aureus. The results from minimum inhibitory concentration (MIC) determinations showed that CHQA exhibited moderate inhibitory effects on all of the tested pathogens with MIC values ranging from 2.5-10 mg/mL. Membrane potential measurements and flow cytometric analysis demonstrated that CHQA damaged the cytoplasmic membrane of S. aureus, causing a significant membrane hyperpolarization with a loss of membrane integrity. Moreover, CHQA induced an increase in membrane fluidity and conformational changes in membrane protein of S. aureus, suggesting that CHQA probably acts on the cell membrane by interactions with membrane lipid and protein. Transmission electron microscopic observations further confirmed that CHQA disrupted the cell membrane of S. aureus and caused severe morphological changes, which even led to leakage of intracellular constituents. These findings indicated that CHQA could have the potential to serve as a natural antibacterial agent to control and prevent the growth of pathogens in food and in food-processing environments. PMID:27548123

  14. Inhibition of cellulose enzymatic hydrolysis by laccase-derived compounds from phenols.

    PubMed

    Oliva-Taravilla, Alfredo; Tomás-Pejó, Elia; Demuez, Marie; González-Fernández, Cristina; Ballesteros, Mercedes

    2015-01-01

    The presence of inhibitors compounds after pretreatment of lignocellulosic materials affects the saccharification and fermentation steps in bioethanol production processes. Even though, external addition of laccases selectively removes the phenolic compounds from lignocellulosic prehydrolysates, when it is coupled to saccharification step, lower hydrolysis yields are attained. Vanillin, syringaldehyde and ferulic acid are phenolic compounds commonly found in wheat-straw prehydrolysate after steam-explosion pretreatment. These three phenolic compounds were used in this study to elucidate the inhibitory mechanisms of laccase-derived compounds after laccase treatment. Reaction products derived from laccase oxidation of vanillin and syringaldehyde showed to be the strongest inhibitors. The presence of these products causes a decrement on enzymatic hydrolysis yield of a model cellulosic substrate (Sigmacell) of 46.6 and 32.6%, respectively at 24 h. Moreover, a decrease in more than 50% of cellulase and β-glucosidase activities was observed in presence of laccase and vanillin. This effect was attributed to coupling reactions between phenoxyl radicals and enzymes. On the other hand, when the hydrolysis of Sigmacell was performed in presence of prehydrolysate from steam-exploded wheat straw a significant inhibition on enzymatic hydrolysis was observed independently of laccase treatment. This result pointed out that the other components of wheat-straw prehydrolysate are affecting the enzymatic hydrolysis to a higher extent than the possible laccase-derived products.

  15. Antioxidant Activity of Phenolic Compounds from Fava Bean Sprouts.

    PubMed

    Okumura, Koharu; Hosoya, Takahiro; Kawarazaki, Kai; Izawa, Norihiko; Kumazawa, Shigenori

    2016-06-01

    Fava beans are eaten all over the world and recently, marketing for their sprouts began in Japan. Fava bean sprouts contain more polyphenols and l-3,4-dihydroxyphenylalanine (l-DOPA) than the bean itself. Our antioxidant screening program has shown that fava bean sprouts also possess a higher antioxidant activity than other commercially available sprouts and mature beans. However, the individual constituents of fava bean sprouts are not entirely known. In the present study, we investigated the phenolic compounds of fava bean sprouts and their antioxidant activity. Air-dried fava bean sprouts were treated with 80% methanol and the extract was partitioned in water with chloroform and ethyl acetate. HPLC analysis had shown that the ethyl acetate-soluble parts contained phenolic compounds, separated by preparative HPLC to yield 5 compounds (1-5). Structural analysis using NMR and MS revealed that the compounds isolated were kaempferol glycosides. All isolated compounds had an α-rhamnose at the C-7 position with different sugars attached at the C-3 position. Compounds 1-5 had β-galactose, β-glucose, α-rhamnose, 6-acetyl-β-galactose and 6-acetyl-β-glucose, respectively, at the C-3 position. The amount of l-DOPA in fava bean sprouts was determined by the quantitative (1) H NMR technique. The l-DOPA content was 550.45 mg ± 11.34 /100 g of the raw sprouts. The antioxidant activities of compounds 2-5 and l-DOPA were evaluated using the 2,2-diphenyl-1-picrylhydrazyl scavenging assay. l-DOPA showed high antioxidant activity, but the isolated kaempferol glycosides showed weak activity. Therefore, it can be suggested that l-DOPA contributed to the antioxidant activity of fava bean sprouts.

  16. Antioxidant Activity of Phenolic Compounds from Fava Bean Sprouts.

    PubMed

    Okumura, Koharu; Hosoya, Takahiro; Kawarazaki, Kai; Izawa, Norihiko; Kumazawa, Shigenori

    2016-06-01

    Fava beans are eaten all over the world and recently, marketing for their sprouts began in Japan. Fava bean sprouts contain more polyphenols and l-3,4-dihydroxyphenylalanine (l-DOPA) than the bean itself. Our antioxidant screening program has shown that fava bean sprouts also possess a higher antioxidant activity than other commercially available sprouts and mature beans. However, the individual constituents of fava bean sprouts are not entirely known. In the present study, we investigated the phenolic compounds of fava bean sprouts and their antioxidant activity. Air-dried fava bean sprouts were treated with 80% methanol and the extract was partitioned in water with chloroform and ethyl acetate. HPLC analysis had shown that the ethyl acetate-soluble parts contained phenolic compounds, separated by preparative HPLC to yield 5 compounds (1-5). Structural analysis using NMR and MS revealed that the compounds isolated were kaempferol glycosides. All isolated compounds had an α-rhamnose at the C-7 position with different sugars attached at the C-3 position. Compounds 1-5 had β-galactose, β-glucose, α-rhamnose, 6-acetyl-β-galactose and 6-acetyl-β-glucose, respectively, at the C-3 position. The amount of l-DOPA in fava bean sprouts was determined by the quantitative (1) H NMR technique. The l-DOPA content was 550.45 mg ± 11.34 /100 g of the raw sprouts. The antioxidant activities of compounds 2-5 and l-DOPA were evaluated using the 2,2-diphenyl-1-picrylhydrazyl scavenging assay. l-DOPA showed high antioxidant activity, but the isolated kaempferol glycosides showed weak activity. Therefore, it can be suggested that l-DOPA contributed to the antioxidant activity of fava bean sprouts. PMID:27155370

  17. Reaction of bromine and chlorine with phenolic compounds and natural organic matter extracts--Electrophilic aromatic substitution and oxidation.

    PubMed

    Criquet, Justine; Rodriguez, Eva M; Allard, Sebastien; Wellauer, Sven; Salhi, Elisabeth; Joll, Cynthia A; von Gunten, Urs

    2015-11-15

    Phenolic compounds are known structural moieties of natural organic matter (NOM), and their reactivity is a key parameter for understanding the reactivity of NOM and the disinfection by-product formation during oxidative water treatment. In this study, species-specific and/or apparent second order rate constants and mechanisms for the reactions of bromine and chlorine have been determined for various phenolic compounds (phenol, resorcinol, catechol, hydroquinone, phloroglucinol, bisphenol A, p-hydroxybenzoic acid, gallic acid, hesperetin and tannic acid) and flavone. The reactivity of bromine with phenolic compounds is very high, with apparent second order rate constants at pH 7 in the range of 10(4) to 10(7) M(-1) s(-1). The highest value was recorded for the reaction between HOBr and the fully deprotonated resorcinol (k = 2.1 × 10(9) M(-1) s(-1)). The reactivity of phenolic compounds is enhanced by the activating character of the phenolic substituents, e.g. further hydroxyl groups. With the data set from this study, the ratio between the species-specific rate constants for the reactions of chlorine versus bromine with phenolic compounds was confirmed to be about 3000. Phenolic compounds react with bromine or chlorine either by oxidation (electron transfer, ET) or electrophilic aromatic substitution (EAS) processes. The dominant process mainly depends on the relative position of the hydroxyl substituents and the possibility of quinone formation. While phenol, p-hydroxybenzoic acid and bisphenol A undergo EAS, hydroquinone, catechol, gallic acid and tannic acid, with hydroxyl substituents in ortho or para positions, react with bromine by ET leading to quantitative formation of the corresponding quinones. Some compounds (e.g. phloroglucinol) show both partial oxidation and partial electrophilic aromatic substitution and the ratio observed for the pathways depends on the pH. For the reaction of six NOM extracts with bromine, electrophilic aromatic substitution

  18. Reaction of bromine and chlorine with phenolic compounds and natural organic matter extracts--Electrophilic aromatic substitution and oxidation.

    PubMed

    Criquet, Justine; Rodriguez, Eva M; Allard, Sebastien; Wellauer, Sven; Salhi, Elisabeth; Joll, Cynthia A; von Gunten, Urs

    2015-11-15

    Phenolic compounds are known structural moieties of natural organic matter (NOM), and their reactivity is a key parameter for understanding the reactivity of NOM and the disinfection by-product formation during oxidative water treatment. In this study, species-specific and/or apparent second order rate constants and mechanisms for the reactions of bromine and chlorine have been determined for various phenolic compounds (phenol, resorcinol, catechol, hydroquinone, phloroglucinol, bisphenol A, p-hydroxybenzoic acid, gallic acid, hesperetin and tannic acid) and flavone. The reactivity of bromine with phenolic compounds is very high, with apparent second order rate constants at pH 7 in the range of 10(4) to 10(7) M(-1) s(-1). The highest value was recorded for the reaction between HOBr and the fully deprotonated resorcinol (k = 2.1 × 10(9) M(-1) s(-1)). The reactivity of phenolic compounds is enhanced by the activating character of the phenolic substituents, e.g. further hydroxyl groups. With the data set from this study, the ratio between the species-specific rate constants for the reactions of chlorine versus bromine with phenolic compounds was confirmed to be about 3000. Phenolic compounds react with bromine or chlorine either by oxidation (electron transfer, ET) or electrophilic aromatic substitution (EAS) processes. The dominant process mainly depends on the relative position of the hydroxyl substituents and the possibility of quinone formation. While phenol, p-hydroxybenzoic acid and bisphenol A undergo EAS, hydroquinone, catechol, gallic acid and tannic acid, with hydroxyl substituents in ortho or para positions, react with bromine by ET leading to quantitative formation of the corresponding quinones. Some compounds (e.g. phloroglucinol) show both partial oxidation and partial electrophilic aromatic substitution and the ratio observed for the pathways depends on the pH. For the reaction of six NOM extracts with bromine, electrophilic aromatic substitution

  19. The Combined Effects of Ethylene and MeJA on Metabolic Profiling of Phenolic Compounds in Catharanthus roseus Revealed by Metabolomics Analysis.

    PubMed

    Liu, Jia; Liu, Yang; Wang, Yu; Zhang, Zhong-Hua; Zu, Yuan-Gang; Efferth, Thomas; Tang, Zhong-Hua

    2016-01-01

    Phenolic compounds belong to a class of secondary metabolites and are implicated in a wide range of responsive mechanisms in plants triggered by both biotic and abiotic elicitors. In this study, we approached the combinational effects of ethylene and MeJA (methyl jasmonate) on phenolic compounds profiles and gene expressions in the medicinal plant Catharanthus roseus. In virtue of a widely non-targeted metabolomics method, we identified a total of 34 kinds of phenolic compounds in the leaves, composed by 7 C6C1-, 11 C6C3-, and 16 C6C3C6 compounds. In addition, 7 kinds of intermediates critical for the biosynthesis of phenolic compounds and alkaloids were identified and discussed with phenolic metabolism. The combinational actions of ethylene and MeJA effectively promoted the total phenolic compounds, especially the C6C1 compounds (such as salicylic acid, benzoic acid) and C6C3 ones (such as cinnamic acid, sinapic acid). In contrast, the C6C3C6 compounds displayed a notably inhibitory trend in this case. Subsequently, the gene-to-metabolite networks were drawn up by searching for correlations between the expression profiles of 5 gene tags and the accumulation profiles of 41 metabolite peaks. Generally, we provide an insight into the controlling mode of ethylene-MeJA combination on phenolic metabolism in C. roseus leaves. PMID:27375495

  20. The Combined Effects of Ethylene and MeJA on Metabolic Profiling of Phenolic Compounds in Catharanthus roseus Revealed by Metabolomics Analysis

    PubMed Central

    Liu, Jia; Liu, Yang; Wang, Yu; Zhang, Zhong-Hua; Zu, Yuan-Gang; Efferth, Thomas; Tang, Zhong-Hua

    2016-01-01

    Phenolic compounds belong to a class of secondary metabolites and are implicated in a wide range of responsive mechanisms in plants triggered by both biotic and abiotic elicitors. In this study, we approached the combinational effects of ethylene and MeJA (methyl jasmonate) on phenolic compounds profiles and gene expressions in the medicinal plant Catharanthus roseus. In virtue of a widely non-targeted metabolomics method, we identified a total of 34 kinds of phenolic compounds in the leaves, composed by 7 C6C1-, 11 C6C3-, and 16 C6C3C6 compounds. In addition, 7 kinds of intermediates critical for the biosynthesis of phenolic compounds and alkaloids were identified and discussed with phenolic metabolism. The combinational actions of ethylene and MeJA effectively promoted the total phenolic compounds, especially the C6C1 compounds (such as salicylic acid, benzoic acid) and C6C3 ones (such as cinnamic acid, sinapic acid). In contrast, the C6C3C6 compounds displayed a notably inhibitory trend in this case. Subsequently, the gene-to-metabolite networks were drawn up by searching for correlations between the expression profiles of 5 gene tags and the accumulation profiles of 41 metabolite peaks. Generally, we provide an insight into the controlling mode of ethylene-MeJA combination on phenolic metabolism in C. roseus leaves. PMID:27375495

  1. Modulation of chlorogenic acid biosynthesis in Solanum lycopersicum; consequences for phenolic accumulation and UV-tolerance.

    PubMed

    Clé, Carla; Hill, Lionel M; Niggeweg, Ricarda; Martin, Cathie R; Guisez, Yves; Prinsen, Els; Jansen, Marcel A K

    2008-08-01

    Chlorogenic acid (CGA) is one of the most abundant phenolic compounds in tomato (Solanum lycopersicum). Hydroxycinnamoyl CoA quinate transferase (HQT) is the key enzyme catalysing CGA biosynthesis in tomato. We have studied the relationship between phenolic accumulation and UV-susceptibility in transgenic tomato plants with altered HQT expression. Overall, increased CGA accumulation was associated with increased UV-protection. However, the genetic manipulation of HQT expression also resulted in more complex alterations in the profiles of phenolics. Levels of rutin were relatively high in both HQT gene-silenced and HQT-overexpressing plants raised in plant growth tunnels. This suggests plasticity in the flux along different branches of phenylpropanoid metabolism and the existence of regulatory mechanisms that direct the flow of phenolic precursors in response to both metabolic parameters and environmental conditions. These changes in composition of the phenolic pool affected the relative levels of UV-tolerance. We conclude that the capability of the phenolic compounds to protect against potentially harmful UV radiation is determined both by the total levels of phenolics that accumulate in leaves as well as by the specific composition of the phenolic profile.

  2. Analysis of antioxidative phenolic compounds in artichoke (Cynara scolymus L.).

    PubMed

    Wang, Mingfu; Simon, James E; Aviles, Irma Fabiola; He, Kan; Zheng, Qun-Yi; Tadmor, Yaakov

    2003-01-29

    Artichoke leaf is an herbal medicine known for a long time. A systematic antioxidant activity-directed fractionation procedure was used to purify antioxidative components from the aqueous methanol extractions of artichoke heads and leaves in this study. Seven active polyphenolic compounds were purified from artichoke, and structural elucidation of each was achieved using MS and NMR. Two of these compounds, apigenin-7-rutinoside and narirutin, were found to be unique to artichoke heads, this represents the first report of these compounds in the edible portion of this plant. The contents of these antioxidants and total phenols in dried artichoke samples from leaves and immature and mature heads of three varieties, Imperial Star, Green Globe, and Violet, were then analyzed and compared by colorimetric and validated HPLC methods. Significant differences by variety and plant organ were observed.

  3. Contents of vitamins, mineral elements, and some phenolic compounds in cultivated mushrooms.

    PubMed

    Mattila, P; Könkö, K; Eurola, M; Pihlava, J M; Astola, J; Vahteristo, L; Hietaniemi, V; Kumpulainen, J; Valtonen, M; Piironen, V

    2001-05-01

    The aim of the study was to determine the contents of mineral elements (Ca, K, Mg, Na, P, Cu, Fe, Mn, Cd, Pb, and Se), vitamins (B(1), B(2), B(12), C, D, folates, and niacin), and certain phenolic compounds (flavonoids, lignans, and phenolic acids) in the cultivated mushrooms Agaricus bisporus/white, Agaricus bisporus/brown, Lentinus edodes, and Pleurotus ostreatus. Selenium, toxic heavy metals (Cd, Pb), and other mineral elements were analyzed by ETAAS, ICP-MS, and ICP methods, respectively; vitamins were detected by microbiological methods (folates, niacin, and vitamin B(12)) or HPLC methods (other vitamins), and phenolic compounds were analyzed by HPLC (flavonoids) or GC--MS methods (lignans and phenolic acids). Cultivated mushrooms were found to be good sources of vitamin B(2), niacin, and folates, with contents varying in the ranges 1.8--5.1, 31--65, and 0.30--0.64 mg/100 g dry weight (dw), respectively. Compared with vegetables, mushrooms proved to be a good source of many mineral elements, e.g., the contents of K, P, Zn, and Cu varied in the ranges 26.7--47.3 g/kg, 8.7--13.9 g/kg, 47--92 mg/kg, and 5.2--35 mg/kg dw, respectively. A. bisporus/brown contained large amounts of Se (3.2 mg/kg dw) and the levels of Cd were quite high in L. edodes (1.2 mg/kg dw). No flavonoids or lignans were found in the mushrooms analyzed. In addition, the phenolic acid contents were very low.

  4. Poly(N-vinylimidazole/ethylene glycol dimethacrylate) for the purification and isolation of phenolic acids.

    PubMed

    Schemeth, Dieter; Noël, Jean-Christophe; Jakschitz, Thomas; Rainer, Matthias; Tessadri, Richard; Huck, Christian W; Bonn, Günther K

    2015-07-23

    In this study we report the novel polymeric resin poly(N-vinyl imidazole/ethylene glycol dimethacrylate) for the purification and isolation of phenolic acids. The monomer to crosslinker ratio and the porogen composition were optimized for isolating phenolic acids diluted in acetonitrile at normal phase chromatography conditions, first. Acetonitrile serves as polar, aprotic solvent, dissolving phenolic acids but not interrupting interactions with the stationary phase due to the approved Hansen solubility parameters. The optimized resin demonstrated high loading capacities and adsorption abilities particularly for phenolic acids in both, acetonitrile and aqueous solutions. The adsorption behavior of aqueous standards can be attributed to ion exchange effects due to electrostatic interactions between protonated imidazole residues and deprotonated phenolic acids. Furthermore, adsorption experiments and subsequent curve fittings provide information of maximum loading capacities of single standards according to the Langmuir adsorption model. Recovery studies of the optimized polymer in the normal-phase and ion-exchange mode illustrate the powerful isolation properties for phenolic acids and are comparable or even better than typical, commercially available solid phase extraction materials. In order to prove the applicability, a highly complex extract of rosemary leaves was purified by poly(N-vinyl imidazole/ethylene glycol dimethacrylate) and the isolated compounds were identified using UHPLC-qTOF-MS.

  5. Bound Phenolics of Quinoa Seeds Released by Acid, Alkaline, and Enzymatic Treatments and Their Antioxidant and α-Glucosidase and Pancreatic Lipase Inhibitory Effects.

    PubMed

    Tang, Yao; Zhang, Bing; Li, Xihong; Chen, Peter X; Zhang, Hua; Liu, Ronghua; Tsao, Rong

    2016-03-01

    Unextractable phenolics from plant foods and their role in health benefits have become increasingly important. Meal residues of three quinoa seeds free of fat and extractable phenolics were subjected to acid, alkaline, and enzymatic hydrolyses. The total and individual phenolic compounds released were analyzed, and 19 phenolics, predominantly phenolic acids and several flavonoids, were identified. The concentration of bound phenolics was highest in black quinoa followed by red and white, regardless of the hydrolysis method. Higher phenolic contents also showed stronger antioxidant activities and inhibition of α-glucosidase and pancreatic lipase activities. Carbohydrases, that is, pectinase, xylanase and feruloyl esterase, which effectively liberated bound phenolics are known to be secreted by colonic bacteria, suggesting potential antioxidant and anti-inflammatory effects by these compounds in the large intestine during colonic fermentation. These results can also be applied to treat foods high in bound phenolics to enhance bioaccessibility.

  6. Bound Phenolics of Quinoa Seeds Released by Acid, Alkaline, and Enzymatic Treatments and Their Antioxidant and α-Glucosidase and Pancreatic Lipase Inhibitory Effects.

    PubMed

    Tang, Yao; Zhang, Bing; Li, Xihong; Chen, Peter X; Zhang, Hua; Liu, Ronghua; Tsao, Rong

    2016-03-01

    Unextractable phenolics from plant foods and their role in health benefits have become increasingly important. Meal residues of three quinoa seeds free of fat and extractable phenolics were subjected to acid, alkaline, and enzymatic hydrolyses. The total and individual phenolic compounds released were analyzed, and 19 phenolics, predominantly phenolic acids and several flavonoids, were identified. The concentration of bound phenolics was highest in black quinoa followed by red and white, regardless of the hydrolysis method. Higher phenolic contents also showed stronger antioxidant activities and inhibition of α-glucosidase and pancreatic lipase activities. Carbohydrases, that is, pectinase, xylanase and feruloyl esterase, which effectively liberated bound phenolics are known to be secreted by colonic bacteria, suggesting potential antioxidant and anti-inflammatory effects by these compounds in the large intestine during colonic fermentation. These results can also be applied to treat foods high in bound phenolics to enhance bioaccessibility. PMID:26853559

  7. Development of novel antibiofouling materials from natural phenol compounds

    NASA Astrophysics Data System (ADS)

    Chelikani, Rahul; Kim, Dong Shik

    2007-03-01

    Biofilms consist of a gelatinous matrix formed on a solid surface by microbial organisms.Biofilm is caused due to the adhesion of microbes to solid surfaces with production of extracellular polymers and the process of the biofilm formation is reffered to as biofouling.Biofouling causes serious problems in chemical, medical and pharmaceutical industries.Although there have been some antibiofouling materials developed over the years,no plausible results have been found yet.Natural polyphenolic compounds like flavanoids,cathechins have strong antioxidant and antimicrobial properties.Recently,apocynin,a phenol derivative,was polymerized to form oligomers,which can regulate intracellular pathways in cancer cells preventing cell proliferation and migration.These natural phenolic compounds have never been applied to solid surfaces to prevent biofouling.It is thought that probably because of the difficulty to crosslink them to form a stable coating.In this study,some novel polyphenolic compounds synthesized using enzymatic technique from cashew nut shell liquid,a cheap and renewable byproduct of the cashew industry are used as coating materials to prevent biofouling.The interaction of these materials with microbes preventing fouling on surfaces and the chemico-physical properties of the materials causing the antibiofouling effect will be discussed.It is critical to understand the antibiofouling mechanism of these materials for better design and application in various fields.

  8. Phenylalanine and LED lights enhance phenolic compound production in Tartary buckwheat sprouts.

    PubMed

    Seo, Jeong-Min; Arasu, Mariadhas Valan; Kim, Yeon-Bok; Park, Sang Un; Kim, Sun-Ju

    2015-06-15

    The present study aimed to investigate the effects of different l-phenylalanine (l-Phe) concentrations and various light-emitting diodes (LEDs) on the accumulation of phenolic compounds (chlorogenic acid, vitexin, rutin, quercetin, cyanidin 3-O-glucoside, and cyanidin 3-O-rutinoside) in Tartary buckwheat sprouts. We found that 5mM was the optimum l-Phe concentration for the synthesis of total and individual phenolic compounds. The highest rutin (53.09 mg/g DW) and chlorogenic acid (5.62 mg/g DW) content was observed with Red+Blue and white lights. Comprehensive differences in total and individual anthocyanin content were observed between different lights; however, the total anthocyanin content (9.12 mg/g DW) was 1.5-fold higher in blue light. The expression levels of regulatory genes, such as FtDFR and FtANS, were 7.1-fold higher with l-Phe treatment. Gene expression results showed that the phenolic compounds in Tartary buckwheat sprouts increased with the use of l-Phe and LED lights.

  9. Adsorption behaviors of some phenolic compounds onto high specific area activated carbon cloth.

    PubMed

    Ayranci, Erol; Duman, Osman

    2005-09-30

    Adsorption of phenol, hydroquinone, m-cresol, p-cresol and p-nitrophenol from aqueous solutions onto high specific area activated carbon cloth has been studied. The effect of ionization on adsorption of these ionizable phenolic compounds was examined by studying the adsorption from acidic, basic and natural pH solutions. Kinetics of adsorption was followed by in situ UV spectroscopy over a period of 90 min. First-order rate law was found to be valid for the kinetics of adsorption processes and the rate constants were determined. The highest rate constants were obtained for the adsorption from solutions at the natural pH. The lowest rate constants were observed in basic solutions. The rate constants decreased in the order p-nitrophenol approximately m-cresol>p-cresol>hydroquinone approximately phenol. Adsorption isotherms were derived at 30 degrees C and the isotherm data were treated according to Langmuir, Freundlich and Tempkin isotherm equations. The goodness of fit of experimental data to these isotherm equations was tested and the parameters of equations were determined. The possible interactions of compounds with the carbon surface were discussed considering the charge of the surface and the possible ionization of compounds at acidic, basic and natural pH conditions. PMID:15941619

  10. Total Phenolic, Phenolic Acid, Anthocyanin, Flavan-3-ol, and Flavonol Profiles and Antioxidant Properties of Pinto and Black Beans ( Phaseolus vulgaris L.) as Affected by Thermal Processing.

    PubMed

    Xu, Baojun; Chang, Sam K C

    2009-06-10

    The effects of boiling and steaming processes at atmospheric and high pressures on the phenolic components and antioxidant properties of pinto and black beans were investigated. In comparison to the original raw beans, all processing methods caused significant (p < 0.05) decreases in total phenolic content (TPC), total flavonoid content (TFC), condensed tannin content (CTC), monomeric anthocyanin content (MAC), DPPH free-radical scavenging activity (DPPH), ferric-reducing antioxidant power (FRAP), and oxygen radical absorbing capacity (ORAC) values in both pinto and black beans. Steaming processing resulted in a greater retention of TPC, DPPH, FRAP, and ORAC values than the boiling processes in both pinto and black beans. To further investigate how thermal processing affected phenolic compositions and to elucidate the contribution of individual phenolic compounds to antioxidant properties, phenolic acids, anthocyanins, flavan-3-ols, and flavonols were quantitatively analyzed by high-performance liquid chromatography (HPLC). All thermal processing significantly (p < 0.05) affected individual phenolic acids, anthocyanins, flavan-3-ols, and flavonols, significantly (p < 0.05) reduced total phenolic acid contents in both pinto and black beans and total flavonol contents in pinto beans, and dramatically reduced anthocyanin contents in black beans. Phenolic acids and flavonols may play important roles on the overall antioxidant activities of pinto beans, while anthocyanins, flavan-3-ols, and flavonols may play important roles on the overall antioxidant activities of black beans.

  11. Growth inhibitory effect of grape phenolics against wine spoilage yeasts and acetic acid bacteria.

    PubMed

    Pastorkova, E; Zakova, T; Landa, P; Novakova, J; Vadlejch, J; Kokoska, L

    2013-02-15

    This paper investigates the in vitro antimicrobial potential of 15 grape phenolic compounds of various chemical classes (phenolic acids, stilbenes and flavonoids) using the broth microdilution method against yeasts and acetic acid bacteria frequently occurring in deteriorated wine. Pterostilbene (MICs=32-128 μg/mL), resveratrol (MICs=256-512 μg/mL) and luteolin (MICs=256-512 μg/mL) are among six active compounds that possessed the strongest inhibitory effects against all microorganisms tested. In the case of phenolic acids, myricetin, p-coumaric and ferulic acids exhibited selective antimicrobial activity (MICs=256-512 μg/mL), depending upon yeasts and bacteria tested. In comparison with potassium metabisulphite, all microorganisms tested were more susceptible to the phenolics. The results revealed the antibacterial and antiyeast effects against wine spoilage microorganisms of several highly potent phenolics naturally occurring in grapes. These findings also provide arguments for further investigation of stilbenes as prospective compounds reducing the need for the use of sulphites in winemaking.

  12. Subcritical water extraction of flavoring and phenolic compounds from cinnamon bark (Cinnamomum zeylanicum).

    PubMed

    Khuwijitjaru, Pramote; Sayputikasikorn, Nucha; Samuhasaneetoo, Suched; Penroj, Parinda; Siriwongwilaichat, Prasong; Adachi, Shuji

    2012-01-01

    Cinnamon bark (Cinnamomum zeylanicum) powder was treated with subcritical water at 150 and 200°C in a semi-continuous system at a constant flow rate (3 mL/min) and pressure (6 MPa). Major flavoring compounds, i.e., cinnamaldehyde, cinnamic acid, cinnamyl alcohol and coumarin, were extracted at lower recoveries than the extraction using methanol, suggesting that degradation of these components might occur during the subcritical water treatment. Caffeic, ferulic, p-coumaric, protocatechuic and vanillic acids were identified from the subcritical water treatment. Extraction using subcritical water was more effective to obtain these acids than methanol (50% v/v) in both number of components and recovery, especially at 200°C. Subcritical water treatment at 200°C also resulted in a higher total phenolic content and DPPH radical scavenging activity than the methanol extraction. The DPPH radical scavenging activity and total phenolic content linearly correlated but the results suggested that the extraction at 200°C might result in other products that possessed a free radical scavenging activity other than the phenolic compounds.

  13. Antioxidant and nitrite-scavenging capacities of phenolic compounds from sugarcane (Saccharum officinarum L.) tops.

    PubMed

    Sun, Jian; He, Xue-Mei; Zhao, Mou-Ming; Li, Li; Li, Chang-Bao; Dong, Yi

    2014-08-26

    Sugarcane tops were extracted with 50% ethanol and fractionated by petroleum ether, ethyl acetate (EtOAc), and n-butyl alcohol successively. Eight phenolic compounds in EtOAc extracts were purified through silica gel and Sephadex LH-20 column chromatographies, and then identified by nuclear magnetic resonance and electrospray ionization mass spectra. The results showed that eight phenolic compounds from EtOAc extracts were identified as caffeic acid, cis-p-hydroxycinnamic acid, quercetin, apigenin, albanin A, australone A, moracin M, and 5'-geranyl-5,7,2',4'-tetrahydroxyflavone. The antioxidant and nitrite-scavenging capacities of different solvent extracts correlated positively with their total phenolic (TP) contents. Amongst various extracts, EtOAc extracts possessed the highest TP content and presented the strongest oxygen radical absorbance capacity (ORAC), 1,1'-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging capacity, 2,2'-azobis-3-ethylbenthiaazoline-6-sulfonic acid (ABTS) radical-scavenging capacity, ferric reducing antioxidant power (FRAP) and nitrite-scavenging capacity. Thus, sugarcane tops could be promoted as a source of natural antioxidant.

  14. Effect of phenolic compounds against Aβ aggregation and Aβ-induced toxicity in transgenic C. elegans.

    PubMed

    Jagota, Seema; Rajadas, Jayakumar

    2012-01-01

    Substantial evidence suggests that the aggregation of amyloid-β (Aβ) peptide into fibrillar structures that is rich in β-sheets is implicated as the cause of Alzheimer's disease. Therefore, an attractive therapeutic strategy is to prevent or alter Aβ aggregation. Phenolic compounds are natural substances that are composed of one or more aromatic phenolic rings and present in wine, tea, fruits, vegetables and a wide variety of plants. In this work, we investigated the effects of ferulic acid, morin, quercetin and gossypol against Aβ aggregation. From the ThT and turbidity assays, it is observed that in addition to the fibril aggregate, another type of aggregate is formed in the presence of morin, quercetin, and gossypol. On the other hand, ferulic acid did not prevent fibril formation, but it did appear to reduce the average length of fibrils compared to Aβ alone. To study the protective effects of phenolic compounds on Aβ-induced toxicity, we utilized the nematode Caenorhabditis elegans (C. elegans) as an in vivo model organism, human Aβ is expressed intracellularly in the body wall muscle. We found that exposure of Caenorhabditis elegans to ferulic acid give more protection against Aβ toxicity than morin, quercetin and gossypol. PMID:21858698

  15. Extraction of phenolic compounds from virgin olive oil by deep eutectic solvents (DESs).

    PubMed

    García, Aránzazu; Rodríguez-Juan, Elisa; Rodríguez-Gutiérrez, Guillermo; Rios, José Julian; Fernández-Bolaños, Juan

    2016-04-15

    Deep eutectic solvents (DESs) are "green" solvents, applied in this study for the extraction of phenolic compounds from virgin olive oil (VOO). Different combinations of DES consisting of choline chloride (ChCl) in various mixing ratios with sugars, alcohols, organic acids, and urea, as well as a mixture of three sugars were used. The yields of the DES extractions were compared with those from conventional 80% (v/v) methanol/water. DES showed a good solubility of phenolic compounds with different polarities. The two most abundant secoiridoid derivatives in olive oil, oleacein and oleocanthal, extracted with ChCl/xylitol and ChCl/1,2-propanediol showed an increase of 20-33% and 67.9-68.3% with respect to conventional extraction, respectively. To our knowledge, this is the first time that phenolic compounds have been extracted from VOO oil using DES. Our results suggest that DES offers an efficient, safe, sustainable, and cost effective alternative to methanol for extraction of bioactive compounds from VOO. PMID:26616988

  16. Phenolic compounds from red wine and coffee are associated with specific intestinal microorganisms in allergic subjects.

    PubMed

    Cuervo, Adriana; Hevia, Arancha; López, Patricia; Suárez, Ana; Diaz, Carmen; Sánchez, Borja; Margolles, Abelardo; González, Sonia

    2016-01-01

    The dietary modulation of gut microbiota, suggested to be involved in allergy processes, has recently attracted much interest. While several studies have addressed the use of fibres to modify intestinal microbial populations, information about other components, such as phenolic compounds, is scarce. The aim of this work was to identify the dietary components able to influence the microbiota in 23 subjects suffering from rhinitis and allergic asthma, and 22 age- and sex-matched controls. The food intake was recorded by means of an annual food frequency questionnaire. Dietary fibre tables were obtained from Marlett et al., and the Phenol-Explorer database was used to assess the phenolic compound intake. The quantification of microbial groups was performed using an Ion Torrent 16S rRNA gene-based analysis. The results showed a direct association between the intake of red wine, a source of stilbenes, and the relative abundance of Bacteroides, and between the intake of coffee, rich in phenolic acids, and the abundance of Clostridium, Lactococcus and Lactobacillus genera. Despite epidemiological analyses not establishing causality, these results support the association between polyphenol-rich beverages and faecal microbiota in allergic patients.

  17. Comparative study of phenolic compounds and antioxidant activity in different species of cherries.

    PubMed

    Liu, Yun; Liu, Xinyan; Zhong, Fei; Tian, Rongrong; Zhang, Kaichun; Zhang, Xiaoming; Li, Tianhong

    2011-05-01

    A new spectrometric method ultra performance liquid chromatography-tandem mass spectrometric with high precision and rapid analysis was developed to separate 17 phenolic compounds. Different species of cherries, including 10 sweet cherry (Prunus avium L.) cultivars, a tart cherry (P. cerasus L.) rootstock (CAB), and a hybrid rootstock 'Colt' (P. avium × P. pseudocerasus), were analyzed for phenolics contents by this method. The results showed that significant differences were observed among the phenolic compound contents in different cherry species. In 10 sweet cherry cultivars, the contents of neochlorogenic acid and cyanidin-3O-rutinoside were much higher in red-colored fruits (for example, 64.60 and 44.50 mg/100 g fresh weight in Burlat, respectively) than those in bicolored ones. Principal component analysis revealed that cyanidin-3O-rutinoside was an effective index for grouping the cultivars with similar species and fruit colors. Moreover, there were strong positive correlations between phenolics content and antioxidant activity, which was higher in red-colored cherries. PMID:22417346

  18. Antioxidant Properties of Phenolic Compounds in Renewable Parts of Crataegus pinnatifida inferred from Seasonal Variations.

    PubMed

    Luo, Meng; Yang, Xuan; Hu, Jiao-Yang; Jiao, Jiao; Mu, Fan-Song; Song, Zhuo-Yue; Gai, Qing-Yan; Qiao, Qi; Ruan, Xin; Fu, Yu-Jie

    2016-05-01

    In this study, the effect of seasonal variations on Crataegus pinnatifida, changes in antioxidant activity and active components in C. pinnatifida leaves, roots, twigs, and fruits from May to October were investigated. Through correlation analysis of climatic factors and 7 phenolic compounds yield, the phenolic compounds content was positively correlated with temperatures and daytime. The correlation coefficient of temperatures and daytime were 0.912 and 0.829, respectively. 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, 2,2'-azino-bis 3-ethylbenzothiazoline-6-sulphonic acid (ABTS) radical scavenging and reducing power tests were employed to evaluate the antioxidant activity of the C. pinnatifida. C. pinnatifida leaves exhibited significant advantages in terms of higher phenolic contents and excellent antioxidant activities. Principal component analysis (PCA) revealed that 2 main PC characterize the C. pinnatifida phenolic composition (82.1% of all variance). C. pinnatifida leaves in September possessed remarkable antioxidant activity. The results elucidate that C. pinnatifida leaves, as renewable parts, are suitable for application as antioxidant ingredients.

  19. Antioxidant Properties of Phenolic Compounds in Renewable Parts of Crataegus pinnatifida inferred from Seasonal Variations.

    PubMed

    Luo, Meng; Yang, Xuan; Hu, Jiao-Yang; Jiao, Jiao; Mu, Fan-Song; Song, Zhuo-Yue; Gai, Qing-Yan; Qiao, Qi; Ruan, Xin; Fu, Yu-Jie

    2016-05-01

    In this study, the effect of seasonal variations on Crataegus pinnatifida, changes in antioxidant activity and active components in C. pinnatifida leaves, roots, twigs, and fruits from May to October were investigated. Through correlation analysis of climatic factors and 7 phenolic compounds yield, the phenolic compounds content was positively correlated with temperatures and daytime. The correlation coefficient of temperatures and daytime were 0.912 and 0.829, respectively. 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, 2,2'-azino-bis 3-ethylbenzothiazoline-6-sulphonic acid (ABTS) radical scavenging and reducing power tests were employed to evaluate the antioxidant activity of the C. pinnatifida. C. pinnatifida leaves exhibited significant advantages in terms of higher phenolic contents and excellent antioxidant activities. Principal component analysis (PCA) revealed that 2 main PC characterize the C. pinnatifida phenolic composition (82.1% of all variance). C. pinnatifida leaves in September possessed remarkable antioxidant activity. The results elucidate that C. pinnatifida leaves, as renewable parts, are suitable for application as antioxidant ingredients. PMID:27074499

  20. RP-HPTLC densitometric determination and validation of vanillin and related phenolic compounds in accelerated solvent extract of Vanilla planifolia*.

    PubMed

    Sharma, Upendra Kumar; Sharma, Nandini; Gupta, Ajai Prakash; Kumar, Vinod; Sinha, Arun Kumar

    2007-12-01

    A simple, fast and sensitive RP-HPTLC method is developed for simultaneous quantitative determination of vanillin and related phenolic compounds in ethanolic extracts of Vanilla planifolia pods. In addition to this, the applicability of accelerated solvent extraction (ASE) as an alternative to microwave-assisted extraction (MAE), ultrasound-assisted extraction (UAE) and Soxhlet extraction was also explored for the rapid extraction of phenolic compounds in vanilla pods. Good separation was achieved on aluminium plates precoated with silica gel RP-18 F(254S) in the mobile phase of methanol/water/isopropanol/acetic acid (30:65:2:3, by volume). The method showed good linearity, high precision and good recovery of compounds of interest. ASE showed good extraction efficiency in less time as compared to other techniques for all the phenolic compounds. The present method would be useful for analytical research and for routine analysis of vanilla extracts for their quality control.

  1. Anti-inflammatory effects of phenolic compounds isolated from the flowers of Nymphaea mexicana Zucc.

    PubMed

    Hsu, Chin-Lin; Fang, Song-Chwan; Yen, Gow-Chin

    2013-08-01

    Nymphaea mexicana Zucc. is an aquatic plant species which belongs to the family Nymphaea and is commonly known as the yellow water lily. The aim of this work was to study the in vitro antiinflammatory effects of phenolic compounds isolated from the flowers of Nymphaea mexicana Zucc. Seven phenolic compounds including vanillic acid, 4-methoxy-3,5-dihydroxybenzoic acid, (2R,3R)-3,7-dihydroxyflavanone, naringenin (4), kaempferol 3-O-(3-O-acetyl-a-L-rhamnopyranoside), kaempferol 3-O-(2-O-acetyl-a-L-rhamnopyranoside), and quercetin 3-(30 0-acetylrhamnoside) (7) were isolated from the flowers of Nymphaea mexicana Zucc. These results revealed that compound 4 has the most prominent inhibitory effect on the LPS-stimulated nitric oxide (NO), monocyte chemotactic protein-1 (MCP-1), and tumor necrosis factor-alpha (TNF-a) production in RAW 264.7 macrophages. In addition, compound 4 also inhibited LPS-mediated induction of protein expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase 2 (COX-2), and phospho-ERK in RAW 264.7 macrophages. Thus, compound 4 from the flowers of Nymphaea mexicana Zucc. may provide a potential therapeutic approach for inflammation-associated disorders.

  2. Anti-inflammatory effects of phenolic compounds isolated from the flowers of Nymphaea mexicana Zucc.

    PubMed

    Hsu, Chin-Lin; Fang, Song-Chwan; Yen, Gow-Chin

    2013-08-01

    Nymphaea mexicana Zucc. is an aquatic plant species which belongs to the family Nymphaea and is commonly known as the yellow water lily. The aim of this work was to study the in vitro antiinflammatory effects of phenolic compounds isolated from the flowers of Nymphaea mexicana Zucc. Seven phenolic compounds including vanillic acid, 4-methoxy-3,5-dihydroxybenzoic acid, (2R,3R)-3,7-dihydroxyflavanone, naringenin (4), kaempferol 3-O-(3-O-acetyl-a-L-rhamnopyranoside), kaempferol 3-O-(2-O-acetyl-a-L-rhamnopyranoside), and quercetin 3-(30 0-acetylrhamnoside) (7) were isolated from the flowers of Nymphaea mexicana Zucc. These results revealed that compound 4 has the most prominent inhibitory effect on the LPS-stimulated nitric oxide (NO), monocyte chemotactic protein-1 (MCP-1), and tumor necrosis factor-alpha (TNF-a) production in RAW 264.7 macrophages. In addition, compound 4 also inhibited LPS-mediated induction of protein expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase 2 (COX-2), and phospho-ERK in RAW 264.7 macrophages. Thus, compound 4 from the flowers of Nymphaea mexicana Zucc. may provide a potential therapeutic approach for inflammation-associated disorders. PMID:23727892

  3. Phenolic compounds and antioxidant activity of Italian extra virgin olive oil Monti Iblei.

    PubMed

    Galvano, Fabio; La Fauci, Luca; Graziani, Giulia; Ferracane, Rosalia; Masella, Roberta; Di Giacomo, Claudia; Scacco, Antonio; D'Archivio, Massimo; Vanella, Luca; Galvano, Giacomo

    2007-12-01

    The profile of phenolic compounds, antioxidant capacity, oxidative stability, and chemical characteristics (free acidity, peroxide value, specific extinction K232 and K270 values, and DeltaK) of 22 commercial extra virgin olive oil (EVOO) samples coming from the denomination of protected origin (DPO) Monti Iblei and obtained from olives harvested in the period September-December 2005 in the production area of the province of Siracusa (Sicily, Italy) were evaluated. The content of total phenols, expressed as gallic acid equivalents, ranged from 14.80 to 121.20 mg/100 g, with a mean value of 53.72 mg/100 g, mainly attributable to deacetoxyligstroside aglycone, deacetoxyoleuropein aglycone, oleuropein aglycone, and ligstroside aglycone. The mean values of Trolox equivalent antioxidant capacity (TEAC) and of oxidative stability were 54.76 and 11.99 hours, respectively. Both TEAC and oxidative stability were positively correlated to the phenol content and to the percentage of inclusion of the olive cultivar "Tonda Iblea." The high mean content of phenols, besides conferring prolonged oxidative stability, likely confers to the DPO Monti Iblei EVOO marked potential beneficial effects for human health. PMID:18158836

  4. Comparison of the evolution of low molecular weight phenolic compounds in typical Sherry wines: Fino, Amontillado, and Oloroso.

    PubMed

    García Moreno, M Valme; Barroso, Carmelo García

    2002-12-18

    Changes in the content of low molecular weight phenolic compounds (hydroxybenzoic and hydroxycinnamic acids, aldehydes, and their esterified derivatives, tyrosol and 5-(hydroxymethyl)-2-furaldehyde) during the aging of three different classes of Sherry wine, Fino, Oloroso, and Amontillado, have been studied. The samples studied were taken from each of the scales of the particular aging system applied to the three classes of wine. Clear differences were observed in the behavior of the low molecular weight phenolic in the three classes of wine. The wines subjected to oxidative aging presented a higher phenolic content overall, with the exception of the esterified derivatives of phenolic compounds that are mainly found in the samples that have not undergone any process of oxidation. MANOVA results confirmed that there are significant differences between all of the samples of the three types of wines. Using LDA, a classification of 100% of the samples has been made. PMID:12475270

  5. Effectiveness of phenolic compounds against citrus green mould.

    PubMed

    Sanzani, Simona M; Schena, Leonardo; Ippolito, Antonio

    2014-08-18

    Stored citrus fruit suffer huge losses because of the development of green mould caused by Penicillium digitatum. Usually synthetic fungicides are employed to control this disease, but their use is facing some obstacles, such public concern about possible adverse effects on human and environmental health and the development of resistant pathogen populations. In the present study quercetin, scopoletin and scoparone--phenolic compounds present in several agricultural commodities and associated with response to stresses--were firstly tested in vitro against P. digitatum and then applied in vivo on oranges cv. Navelina. Fruits were wound-treated (100 µg), pathogen-inoculated, stored and surveyed for disease incidence and severity. Although only a minor (≤13%) control effect on P. digitatum growth was recorded in vitro, the in vivo trial results were encouraging. In fact, on phenolic-treated oranges, symptoms appeared at 6 days post-inoculation (DPI), i.e., with a 2 day-delay as compared to the untreated control. Moreover, at 8 DPI, quercetin, scopoletin, and scoparone significantly reduced disease incidence and severity by 69%-40% and 85%-70%, respectively, as compared to the control. At 14 DPI, scoparone was the most active molecule. Based on the results, these compounds might represent an interesting alternative to synthetic fungicides.

  6. Effectiveness of phenolic compounds against citrus green mould.

    PubMed

    Sanzani, Simona M; Schena, Leonardo; Ippolito, Antonio

    2014-01-01

    Stored citrus fruit suffer huge losses because of the development of green mould caused by Penicillium digitatum. Usually synthetic fungicides are employed to control this disease, but their use is facing some obstacles, such public concern about possible adverse effects on human and environmental health and the development of resistant pathogen populations. In the present study quercetin, scopoletin and scoparone--phenolic compounds present in several agricultural commodities and associated with response to stresses--were firstly tested in vitro against P. digitatum and then applied in vivo on oranges cv. Navelina. Fruits were wound-treated (100 µg), pathogen-inoculated, stored and surveyed for disease incidence and severity. Although only a minor (≤13%) control effect on P. digitatum growth was recorded in vitro, the in vivo trial results were encouraging. In fact, on phenolic-treated oranges, symptoms appeared at 6 days post-inoculation (DPI), i.e., with a 2 day-delay as compared to the untreated control. Moreover, at 8 DPI, quercetin, scopoletin, and scoparone significantly reduced disease incidence and severity by 69%-40% and 85%-70%, respectively, as compared to the control. At 14 DPI, scoparone was the most active molecule. Based on the results, these compounds might represent an interesting alternative to synthetic fungicides. PMID:25153867

  7. Analysis of phenolic compounds and radical scavenging activity of Echinacea spp.

    PubMed

    Pellati, Federica; Benvenuti, Stefania; Magro, Lara; Melegari, Michele; Soragni, Fabrizia

    2004-04-16

    The aim of this study was to set up and validate an RP-LC method with DAD-detection to quantify caffeic acid derivatives in various Echinacea spp. Samples were extracted with 80% methanol. The analyses were carried out on a Lichrospher RP-18 column (125 mm x 4 mm i.d., 5 microm), with a mobile phase gradient, which increases the acetonitrile level in a phosphoric acid solution (0.1%). The flow rate was 1.5 ml/min. Detection was set at 330 nm. This method allowed the identification and quantification of caftaric acid, chlorogenic acid, caffeic acid, cynarin, echinacoside and cichoric acid in Echinacea roots and derivatives. The total phenolic content was 10.49 mg/g for E. angustifolia, 17.83 mg/g for E. pallida and 23.23 mg/g for E. purpurea. Among Echinacea commercial herbal medicines, a certain variability in the concentrations of phenolic compounds was observed. The radical scavenging activity of Echinacea methanolic extracts was evaluated in vitro with a spectrophotometric method based on the reduction of an alcoholic 2,2-diphenyl-1-picrylhydrazyl (DPPH*) radical solution at 517 nm in the presence of a hydrogen donating antioxidant. As for pure compounds, echinacoside had the highest capacity to quench DPPH* radicals (EC50 = 6.6 microM), while caftaric acid had the lowest (EC50 = 20.5 microM). The average EC50 values for E. purpurea, E. pallida and E. angustifolia were 134, 167 and 231 microg/ml, respectively. The radical scavenging activity of Echinacea root extracts reflected their phenolic composition. The results indicate that Echinacea roots and derivatives are a good source of natural antioxidants and could be used to prevent free-radical-induced deleterious effects.

  8. Bioactive compounds, RP-HPLC analysis of phenolics, and antioxidant activity of some Portuguese shrub species extracts.

    PubMed

    Luís, Angelo; Domingues, Fernanda; Duarte, Ana Paula

    2011-12-01

    In the ecosystem of Serra Da Estrela, some plant species have the potential to be used as raw material for extraction of bioactive products. The goal of this work was to determine the phenolic, flavonoid, tannin and alkaloid contents of the methanolic extracts of some shrubs (Echinospartum ibericum, Pterospartum tridentatum, Juniperus communis, Ruscus aculeatus, Rubus ulmifolius, Hakea sericea, Cytisus multiflorus, Crataegus monogyna, Erica arborea and Ipomoea acuminata), and then to correlate the phenolic compounds and flavonoids with the antioxidant activity of each extract. The Folin-Ciocalteu's method was used for the determination of total phenols, and tannins were then precipitated with polyvinylpolypyrrolidone (PVPP); a colorimetric method with aluminum chloride was used for the determination of flavonoids, and a Dragendorff's reagent method was used for total alkaloid estimation. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) and beta-carotene bleaching tests were used to assess the antioxidant activity of extracts. The identification of phenolic compounds present in extracts was performed using RP-HPLC. A positive linear correlation between antioxidant activity index and total phenolic content of methanolic extracts was observed. The RP-HPLC procedure showed that the most common compounds were ferulic and ellagic acids and quercetin. Most of the studied shrubs have significant antioxidant properties that are probably due to the existence of phenolic compounds in the extracts. It is noteworthy to emphasize that for Echinospartum ibericum, Hakea sericea and Ipomoea acuminata, to the best of our knowledge, no phytochemical studies have been undertaken nor their use in traditional medicine been described.

  9. Phenolic Compounds from Halimodendron halodendron (Pall.) Voss and Their Antimicrobial and Antioxidant Activities

    PubMed Central

    Wang, Jihua; Lou, Jingfeng; Luo, Chao; Zhou, Ligang; Wang, Mingan; Wang, Lan

    2012-01-01

    Halimodendron halodendron has been used as forage in northwestern China for a long time. Its young leaves and flowers are edible and favored by indigenous people. In this study, eleven phenolic compounds were bioassay-guided and isolated from the aerial parts of H. halodendron for the first time. They were identified by means of physicochemical and spectrometric analysis as quercetin (1), 3,5,7,8,4′-pentahydroxy-3′-methoxy flavone (2), 3-O-methylquercetin (3), 3,3′-di-O-methylquercetin (4), 3,3′-di-O-methylquercetin-7-O-β-d-glucopyranoside (5), isorhamentin-3-O-β-d-rutinoside (6), 8-O-methylretusin (7), 8-O-methylretusin-7-O-β-d-glucopyranoside (8), salicylic acid (9), p-hydroxybenzoic acid (ferulic acid) (10), and 4-hydroxy-3-methoxy cinnamic acid (11). They were sorted as flavonols (1–6), soflavones (7 and 8), and phenolic acids (9–11). Among the compounds, flanools 1–4 revealed a strong antibacterial activity with minimum inhibitory concentration (MIC) values of 50–150 μg/mL, and median inhibitory concentration (IC50) values of 26.8–125.1 μg/mL. The two isoflavones (7 and 8) showed moderate inhibitory activity on the test bacteria. Three phenolic acids (9, 10 and 11) showed strong antibacterial activity with IC50 values of 28.1–149.7 μg/mL. Antifungal activities of the compounds were similar to their antibacterial activities. All these phenolic compounds showed significant antimicrobial activity with a broad spectrum as well as antioxidant activity based on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and β-carotene-linoleic acid bleaching assays. In general, the flavonol aglycones with relatively low polarity exhibited stronger activities than the glycosides. The results suggest the potential of this plant as a source of functional food ingredients and provide support data for its utilization as forage as well. PMID:23109858

  10. Phenolic acid degradation potential and growth behavior of lactic acid bacteria in sunflower substrates.

    PubMed

    Fritsch, Caroline; Heinrich, Veronika; Vogel, Rudi F; Toelstede, Simone

    2016-08-01

    Sunflower flour provides a high content of protein with a well-balanced amino acid composition and is therefore regarded as an attractive source for protein. The use for human nutrition is hindered by phenolic compounds, mainly chlorogenic acid, which can lead under specific circumstances to undesirable discolorations. In this study, growth behavior and degradation ability of chlorogenic acid of four lactic acid bacteria were explored. Data suggested that significant higher fermentation performances on sunflower flour as compared to sunflower protein concentrate were reached by Lactobacillus plantarum, Pediococcus pentosaceus, Lactobacillus gasseri and Bifidobacterium animalis subsp. lactis. In fermentation with the latter two strains reduced amounts of chlorogenic acid were observed in sunflower flour (-11.4% and -19.8%, respectively), which were more pronounced in the protein concentrate (-50.7% and -95.6%, respectively). High tolerances against chlorogenic acid and the cleavage product quinic acid with a minimum inhibitory concentration (MIC) of ≥20.48 mg/ml after 48 h were recorded for all strains except Bifidobacterium animalis subsp. lactis, which was more sensitive. The second cleavage compound, caffeic acid revealed a higher antimicrobial potential with MIC values of 0.64-5.12 mg/ml. In this proof of concept study, degradation versus inhibitory effect suggest the existence of basic mechanisms of interaction between phenolic acids in sunflower and lactic acid bacteria and a feasible way to reduce the chlorogenic acid content, which may help to avoid undesired color changes. PMID:27052717

  11. EFFECT OF PHENOLIC ACIDS AND ESTERS ON RESPIRATION AND REPRODUCTION OF BACTERIA IN URINE.

    PubMed

    KEITH, E S; POWERS, J J

    1965-05-01

    Vanillic, syringic, gallic, and protocatechuic acids, methyl-p-hydroxybenzoate, and propyl-p-hydroxybenzoate generally inhibited respiration in vitro of Escherichia coli, Proteus vulgaris, Pseudomonas aeruginosa, and Aerobacter aerogenes in human urine. In the absence of any other available carbon source, certain of the phenolic compounds were utilized. Reproduction was generally suppressed in urine buffered to pH 7, 5.6, 4.5, and 4.0. The phenolic compounds were used in the range of 0.11 to 0.99 mumole/ml.

  12. Characterisation of calamansi (Citrus microcarpa). Part I: volatiles, aromatic profiles and phenolic acids in the peel.

    PubMed

    Cheong, Mun Wai; Chong, Zhi Soon; Liu, Shao Quan; Zhou, Weibiao; Curran, Philip; Bin Yu

    2012-09-15

    Volatile compounds in the peel of calamansi (Citrus microcarpa) from Malaysia, the Philippines and Vietnam were extracted with dichloromethane and hexane, and then analysed by gas chromatography-mass spectroscopy/flame ionisation detector. Seventy-nine compounds representing >98% of the volatiles were identified. Across the three geographical sources, a relatively small proportion of potent oxygenated compounds was significantly different, exemplified by the highest amount of methyl N-methylanthranilate in Malaysian calamansi peel. Principal component analysis and canonical discriminant analysis were applied to interpret the complex volatile compounds in the calamansi peel extracts, and to verify the discrimination among the different origins. In addition, four common hydroxycinnamic acids (caffeic, p-coumaric, ferulic and sinapic acids) were determined in the methanolic extracts of calamansi peel using ultra-fast liquid chromatography coupled to photodiode array detector. The Philippines calamansi peel contained the highest amount of total phenolic acids. In addition, p-Coumaric acid was the dominant free phenolic acids, whereas ferulic acid was the main bound phenolic acid.

  13. Phenolic Acid Composition, Antiatherogenic and Anticancer Potential of Honeys Derived from Various Regions in Greece

    PubMed Central

    Spilioti, Eliana; Jaakkola, Mari; Tolonen, Tiina; Lipponen, Maija; Virtanen, Vesa; Chinou, Ioanna; Kassi, Eva; Karabournioti, Sofia; Moutsatsou, Paraskevi

    2014-01-01

    The phenolic acid profile of honey depends greatly on its botanical and geographical origin. In this study, we carried out a quantitative analysis of phenolic acids in the ethyl acetate extract of 12 honeys collected from various regions in Greece. Our findings indicate that protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid and p-coumaric acid are the major phenolic acids of the honeys examined. Conifer tree honey (from pine and fir) contained significantly higher concentrations of protocatechuic and caffeic acid (mean: 6640 and 397 µg/kg honey respectively) than thyme and citrus honey (mean of protocatechuic and caffeic acid: 437.6 and 116 µg/kg honey respectively). p-Hydroxybenzoic acid was the dominant compound in thyme honeys (mean: 1252.5 µg/kg honey). We further examined the antioxidant potential (ORAC assay) of the extracts, their ability to influence viability of prostate cancer (PC-3) and breast cancer (MCF-7) cells as well as their lowering effect on TNF- α-induced adhesion molecule expression in endothelial cells (HAEC). ORAC values of Greek honeys ranged from 415 to 2129 µmol Trolox equivalent/kg honey and correlated significantly with their content in protocatechuic acid (p<0.001), p-hydroxybenzoic acid (p<0.01), vanillic acid (p<0.05), caffeic acid (p<0.01), p-coumaric acid (p<0.001) and their total phenolic content (p<0.001). Honey extracts reduced significantly the viability of PC-3 and MCF-7 cells as well as the expression of adhesion molecules in HAEC. Importantly, vanillic acid content correlated significantly with anticancer activity in PC-3 and MCF-7 cells (p<0.01, p<0.05 respectively). Protocatechuic acid, vanillic acid and total phenolic content correlated significantly with the inhibition of VCAM-1 expression (p<0.05, p<0.05 and p<0.01 respectively). In conclusion, Greek honeys are rich in phenolic acids, in particular protocatechuic and p-hydroxybenzoic acid and exhibit significant antioxidant, anticancer and

  14. Phenolic acid composition, antiatherogenic and anticancer potential of honeys derived from various regions in Greece.

    PubMed

    Spilioti, Eliana; Jaakkola, Mari; Tolonen, Tiina; Lipponen, Maija; Virtanen, Vesa; Chinou, Ioanna; Kassi, Eva; Karabournioti, Sofia; Moutsatsou, Paraskevi

    2014-01-01

    The phenolic acid profile of honey depends greatly on its botanical and geographical origin. In this study, we carried out a quantitative analysis of phenolic acids in the ethyl acetate extract of 12 honeys collected from various regions in Greece. Our findings indicate that protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid and p-coumaric acid are the major phenolic acids of the honeys examined. Conifer tree honey (from pine and fir) contained significantly higher concentrations of protocatechuic and caffeic acid (mean: 6640 and 397 µg/kg honey respectively) than thyme and citrus honey (mean of protocatechuic and caffeic acid: 437.6 and 116 µg/kg honey respectively). p-Hydroxybenzoic acid was the dominant compound in thyme honeys (mean: 1252.5 µg/kg honey). We further examined the antioxidant potential (ORAC assay) of the extracts, their ability to influence viability of prostate cancer (PC-3) and breast cancer (MCF-7) cells as well as their lowering effect on TNF- α-induced adhesion molecule expression in endothelial cells (HAEC). ORAC values of Greek honeys ranged from 415 to 2129 µmol Trolox equivalent/kg honey and correlated significantly with their content in protocatechuic acid (p<0.001), p-hydroxybenzoic acid (p<0.01), vanillic acid (p<0.05), caffeic acid (p<0.01), p-coumaric acid (p<0.001) and their total phenolic content (p<0.001). Honey extracts reduced significantly the viability of PC-3 and MCF-7 cells as well as the expression of adhesion molecules in HAEC. Importantly, vanillic acid content correlated significantly with anticancer activity in PC-3 and MCF-7 cells (p<0.01, p<0.05 respectively). Protocatechuic acid, vanillic acid and total phenolic content correlated significantly with the inhibition of VCAM-1 expression (p<0.05, p<0.05 and p<0.01 respectively). In conclusion, Greek honeys are rich in phenolic acids, in particular protocatechuic and p-hydroxybenzoic acid and exhibit significant antioxidant, anticancer and

  15. Phenolic and short-chained aliphatic organic acid constituents of wild oat (Avena fatua L.) seeds.

    PubMed

    Gallagher, R S; Ananth, R; Granger, K; Bradley, B; Anderson, J V; Fuerst, E P

    2010-01-13

    The objective of this research was to identify and quantify the phenolic and short-chained aliphatic organic acids present in the seeds of three wild-type populations of wild oat and compare these results to the chemical composition of seeds from two commonly utilized wild oat isolines (M73 and SH430). Phenolic acids have been shown to serve as germination inhibitors, as well as protection for seeds from biotic and abiotic stress factors in other species, whereas aliphatic organic acids have been linked to germination traits and protection against pathogens. Wild oat populations were grown under a "common garden" environment to remove maternal variation, and the resulting seeds were extracted to remove the readily soluble and chemically bound phenolic and aliphatic organic acid components. Compounds were identified and quantified using gas chromatography-mass spectrometry. Ferulic and p-coumaric acid comprised 99% of the total phenolic acids present in the seeds, of which 91% were contained in the hulls and 98% were in the chemically bound forms. Smaller quantities of OH benzoic and vanillic acid were also detected. Soluble organic acids concentrations were higher in the M73 isoline compared to SH430, suggesting that these chemical constituents could be related to seed dormancy. Malic, succinic, fumaric and azelaic acid were the dominant aliphatic organic acids detected in all seed and chemical fractions.

  16. Phenolic compounds from Andean mashua (Tropaeolum tuberosum) tubers display protection against soybean oil oxidation.

    PubMed

    Betalleluz-Pallardel, I; Chirinos, R; Rogez, H; Pedreschi, R; Campos, D

    2012-06-01

    Phenolic compounds from mashua tuber were evaluated as potential antioxidants to retard the oxidation of crude soybean oil submitted to accelerated storage and frying. During the accelerated storage, an ethanolic crude extract, a purified extract, an aqueous fraction and an ethyl acetate fraction from mashua containing different gallic acid equivalent concentrations (100, 300 and 600 ppm) in oil were evaluated at 55 °C. After 15 days of storage, better effects were evidenced against soybean oil oxidation at 300 and 600 ppm of ethyl acetate fraction in comparison to 200 ppm butylated hydroxytoluene and the control (no antioxidant added). During the frying process at ∼180 °C, principal component analysis revealed that the content of trienes and dienes were strongly correlated with the frying batch. Ethyl acetate fraction at 200 ppm showed the highest efficacy against oil oxidation in terms of polar compound values, free fatty acids and conjugated dienes and trienes in comparison to the oil containing 200 ppm tert-butylhydroquinone and control. Differential scanning calorimetry corroborated the efficacy of ethyl acetate fraction phenolic and it is strongly recommended as method for validation of results. This study provides strong evidence related to the excellent protective effects against soybean oil oxidation of mashua phenolics. This crop could be utilized as an alternative source of natural antioxidants by the oil industry.

  17. Characterization and quantitation of phenolic compounds in new apricot (Prunus armeniaca L.) varieties.

    PubMed

    Ruiz, David; Egea, José; Gil, María I; Tomás-Barberán, Francisco A

    2005-11-30

    Thirty-seven apricot varieties, including four new releases (Rojo Pasión, Murciana, Selene, and Dorada) obtained from different crosses between apricot varieties and three traditional Spanish cultivars (Currot, Mauricio, and Búlida), were separated according to flesh color into four groups: white, yellow, light orange, and orange (mean hue angles in flesh were 88.1, 85.0, 77.6, and 72.4, respectively). Four phenolic compound groups, procyanidins, hydroxycinnamic acid derivatives, flavonols, and anthocyanins, were identified by HPLC-MS/MS and individually quantified using HPLC-DAD. Chlorogenic and neochlorogenic acids, procyanidins B1, B2, and B4, and some procyanidin trimers, quercetin 3-rutinoside, kaempferol 3-rhamnosyl-hexoside and quercetin 3-acetyl-hexoside, cyanidin 3-rutinoside, and 3-glucoside, were detected and quantified in the skin and flesh of the different cultivars. The total phenolics content, quantified as the addition of the individual compounds quantified by HPLC, ranged between 32.6 and 160.0 mg 100 g(-1) of edible tissue. No correlation between the flesh color and the phenolic content of the different cultivars was observed.

  18. Mimicking the hierarchical functions of dentin collagen cross-links with plant derived phenols and phenolic acids.

    PubMed

    Vidal, Cristina M P; Leme, Ariene A; Aguiar, Thaiane R; Phansalkar, Rasika; Nam, Joo-Won; Bisson, Jonathan; McAlpine, James B; Chen, Shao-Nong; Pauli, Guido F; Bedran-Russo, Ana

    2014-12-16

    Proanthocyanidins (PACs) are secondary plant metabolites that mediate nonenzymatic collagen cross-linking and enhance the properties of collagen based tissue, such as dentin. The extent and nature of cross-linking is influenced by the composition and specific chemical structure of the bioactive compounds present in certain PAC-rich extracts. This study investigated the effect of the molecular weight and stereochemistry of polyphenol compounds on two important properties of dentin, biomechanics, and biostability. For that, purified phenols, a phenolic acid, and some of its derivatives were selected: PAC dimers (A1, A2, B1, and B2) and a trimer (C1), gallic acid (Ga), its esters methyl-gallate (MGa) and propyl-gallate (PGa), and a pentagalloyl ester of glucose (PGG). Synergism was assessed by combining the most active PAC and gallic acid derivative. Mechanical properties of dentin organic matrix were determined by the modulus of elasticity obtained in a flexural test. Biostability was evaluated by the resistance to collagenase degradation. PACs significantly enhanced dentin mechanical properties and decreased collagen digestion. Among the gallic acid derivatives, only PGG had a significant enhancing effect. The lack of observed C1:PGG synergy indicates that both compounds have similar mechanisms of interaction with the dentin matrix. These findings reveal that the molecular weight of polyphenols have a determinant effect on their interaction with type I collagen and modulates the mechanism of cross-linking at the molecular, intermolecular, and inter-microfibrillar levels. PMID:25379878

  19. Theoretical investigation on antioxidant activity of vitamins and phenolic acids for designing a novel antioxidant

    NASA Astrophysics Data System (ADS)

    Mohajeri, Afshan; Asemani, S. Somayeh

    2009-07-01

    Theoretical calculations have been performed to predict antioxidant property for two interesting classes of compounds including phenolic acids and vitamins. Important characteristics of antioxidants such as O-H bond dissociation enthalpy (BDE) and ionization potential (IP) were calculated in the gas-phase to analyze the effect of heterocyclic ring, intramolecular hydrogen bonding and presence of electron donating group near the O-H on the antioxidant activity. The results reveal that the presence of intramolecular hydrogen bonding through ortho-hydroxy group lowers BDE, IP and spin density. In general, phenolic acids were found to be more effective antioxidant than vitamins. The H-atom transfer (HAT) mechanism was selected to study the hydrogen abstraction from phenolic compounds by hydroperoxyl radical. It is found that the antioxidant with lower BDE undergoes hydrogen abstraction with low barrier and considerable exothermicity. On the basis of these results we were able to design a novel antioxidant with enhanced activity.

  20. Antioxidant capacity and phenolic compounds of Lonicerae macranthoides by HPLC-DAD-QTOF-MS/MS.

    PubMed

    Hu, Xin; Chen, Lin; Shi, Shuyun; Cai, Ping; Liang, Xuejuan; Zhang, Shuihan

    2016-05-30

    Lonicerae macranthoides with strong antioxidant activity is commonly used in traditional Chinese medicine and folk tea/beverage. However, detailed information about its antioxidant activity and bioactive compounds is limited. Then at first, we comparatively evaluated total phenolic content (TPC), total flavonoid content (TFC) and antioxidant activities of water extract, petroleum ether, ethyl acetate and n-butanol fractions of L. macranthoides. Ethyl acetate fraction exhibited the highest level of TPC (207.38 mg GAE/g DW), TFC (53.06 mg RE/g DW) and the best DPPH scavenge activity and reducing power. n-Butanol fraction showed the best ABTS(+) and O2(-) scavenging activities. Interestingly, water extract, ethyl acetate and n-butanol fractions showed stronger antioxidant activities than positive control, butylated hydroxytoluene (BHT). After that, thirty-one antioxidant phenolic compounds, including twenty-two phenolic acids and nine flavonoids, were screened by DPPH-HPLC experiment and then identified using HPLC-DAD-QTOF-MS/MS. It is noted that twenty-one compounds (1, 3-4, 6-17, 19, 23, 26, 28-29, and 31), as far as was known, were discovered from L. macranthoide for the first time, and eleven of them (3-4, 10-17, and 23) were reported in Lonicera species for the first time. Results indicated that L. macranthoides could serve as promising source of rich antioxidants in foods, beverages and medicines for health promotion. PMID:26970594

  1. Rapid and comprehensive evaluation of (poly)phenolic compounds in pomegranate (Punica granatum L.) juice by UHPLC-MSn.

    PubMed

    Mena, Pedro; Calani, Luca; Dall'Asta, Chiara; Galaverna, Gianni; García-Viguera, Cristina; Bruni, Renato; Crozier, Alan; Del Rio, Daniele

    2012-12-13

    The comprehensive identification of phenolic compounds in food and beverages is a crucial starting point for assessing their biological, nutritional, and technological properties. Pomegranate (Punica granatum L.) has been described as a rich source of (poly)phenolic components, with a broad array of different structures (phenolic acids, flavonoids, and hydrolyzable tannins) and a quick, high throughput, and accurate screening of its complete profile is still lacking. In the present work, a method for UHPLC separation and linear ion trap mass spectrometric (MSn) characterization of pomegranate juice phenolic fraction was optimized by comparing several different analytical conditions. The best solutions for phenolic acids, anthocyanins, flavonoids, and ellagitannins have been delineated and more than 70 compounds have been identified and fully characterized in less than one hour total analysis time. Twenty-one compounds were tentatively detected for the first time in pomegranate juice. The proposed fingerprinting approach could be easily translated to other plant derived food extracts and beverages containing a wide array of phytochemical compounds.

  2. Phenolic compounds from Allium schoenoprasum, Tragopogon pratensis and Rumex acetosa and their antiproliferative effects.

    PubMed

    Kucekova, Zdenka; Mlcek, Jiri; Humpolicek, Petr; Rop, Otakar; Valasek, Pavel; Saha, Petr

    2011-11-03

    Experimental studies have shown that phenolic compounds have antiproliferative and tumour arresting effects. The aim of this original study was to investigate the content of phenolic compounds (PhC) in flowers of Allium schoenoprasum (chive), Tragopogon pratensis (meadow salsify) and Rumex acetosa (common sorrel) and their effect on proliferation of HaCaT cells. Antiproliferative effects were evaluated in vitro using the following concentrations of phenolic compounds in cultivation medium: 100, 75, 50 and 25 µg/mL. Phenolic composition was also determined by HPLC. The results indicate that even low concentrations of these flowers' phenolic compounds inhibited cell proliferation significantly and the possible use of the studied herb's flowers as sources of active phenolic compounds for human nutrition.

  3. Phenolic Compounds in Apple (Malus x domestica Borkh.): Compounds Characterization and Stability during Postharvest and after Processing.

    PubMed

    Francini, Alessandra; Sebastiani, Luca

    2013-01-01

    This paper summarizes the information on the occurrence of phenolic compounds in apple (Malus x domestica Borkh.) fruit and juice, with special reference to their health related properties. As phytochemical molecules belonging to polyphenols are numerous, we will focus on the main apples phenolic compounds with special reference to changes induced by apple cultivar, breeding approaches, fruit postharvest and transformation into juice.

  4. Interaction of milk whey protein with common phenolic acids

    NASA Astrophysics Data System (ADS)

    Zhang, Hao; Yu, Dandan; Sun, Jing; Guo, Huiyuan; Ding, Qingbo; Liu, Ruihai; Ren, Fazheng

    2014-01-01

    Phenolics-rich foods such as fruit juices and coffee are often consumed with milk. In this study, the interactions of α-lactalbumin and β-lactoglobulin with the phenolic acids (chlorogenic acid, caffeic acid, ferulic acid, and coumalic acid) were examined. Fluorescence, CD, and FTIR spectroscopies were used to analyze the binding modes, binding constants, and the effects of complexation on the conformation of whey protein. The results showed that binding constants of each whey protein-phenolic acid interaction ranged from 4 × 105 to 7 × 106 M-n and the number of binding sites n ranged from 1.28 ± 0.13 to 1.54 ± 0.34. Because of these interactions, the conformation of whey protein was altered, with a significant reduction in the amount of α-helix and an increase in the amounts of β-sheet and turn structures.

  5. Soluble Phenolic Compounds in Different Cultivars of Red Clover and Alfalfa, and their Implication for Protection against Proteolysis and Ammonia Production in Ruminants.

    PubMed

    Kagan, Isabelle A; Goff, Ben M; Flythe, Michael D

    2015-07-01

    Red clover (Trifolium pratense) contains soluble phenolic compounds with roles in inhibiting proteolysis and ammonia production. Alfalfa (Medicago sativa) has been found to have a low phenolic content, but few alfalfa and red clover cultivars have been compared for phenolic content. Total soluble phenolics were quantified by a Folin-Ciocalteu colorimetric assay in nine red clover and 27 alfalfa cultivars. Mean total phenolic contents of red clover and alfalfa were 36.5 ± 4.3 mg/gdw and 15.8 ± 1.4 mg/gdw, respectively, with the greater standard deviation of red clover possibly indicating more diversity in phenolic content. Because different phenolic standards had different response factors in the colorimetric assay, the red clover and 11 alfalfa cultivars were analyzed by HPLC to determine if the differences in total soluble phenolics between genera reflected differences in the amounts of phenolics or in the classes of phenolics responding to the colorimetric assay. Two red clover cultivars differed in total phenolics and phaselic acid. Alfalfa produced different phenolic compounds from red clover, at lower concentrations. Extracts of two red clover cultivars were separated by thin-layer chromatography (TLC), and the bands were assayed for activity against Clostridium sticklandii, a bovine ruminal hyper ammonia-producing bacterium (HAB). Only biochanin A had anti-HAB activity. Inhibitory amounts indicated that five red clover cultivars could be suitable sources of anti-HAB activity. PMID:26411026

  6. Separation and characterization of phenolic compounds in fennel (Foeniculum vulgare) using liquid chromatography-negative electrospray ionization tandem mass spectrometry.

    PubMed

    Parejo, Irene; Jauregui, Olga; Sánchez-Rabaneda, Ferran; Viladomat, Francesc; Bastida, Jaume; Codina, Carles

    2004-06-16

    Liquid chromatography (LC) diode array detection (DAD) coupled to negative electrospray ionization (ESI) tandem mass spectrometry (MS/MS) was used for the rapid and sensitive identification of water-soluble phenolic compounds in fennel waste. The plant material was first extracted and then chromatographed on Sephadex LH-20 to afford seven fractions, each of them being subjected to LC-MS analysis. Identification of the compounds was carried out by interpretation of UV, MS, and MS/MS spectra. Forty-two phenolic substances were identified, 27 of which had not previously been reported in fennel, including hydroxycinnamic acid derivatives, flavonoid glycosides, and flavonoid aglycons.

  7. Ultrasound Assisted Extraction of Phenolic Compounds from Peaches and Pumpkins

    PubMed Central

    Altemimi, Ammar; Watson, Dennis G.; Choudhary, Ruplal; Dasari, Mallika R.; Lightfoot, David A.

    2016-01-01

    The ultrasound-assisted extraction (UAE) method was used to optimize the extraction of phenolic compounds from pumpkins and peaches. The response surface methodology (RSM) was used to study the effects of three independent variables each with three treatments. They included extraction temperatures (30, 40 and 50°C), ultrasonic power levels (30, 50 and 70%) and extraction times (10, 20 and 30 min). The optimal conditions for extractions of total phenolics from pumpkins were inferred to be a temperature of 41.45°C, a power of 44.60% and a time of 25.67 min. However, an extraction temperature of 40.99°C, power of 56.01% and time of 25.71 min was optimal for recovery of free radical scavenging activity (measured by 1, 1-diphenyl-2-picrylhydrazyl (DPPH) reduction). The optimal conditions for peach extracts were an extraction temperature of 41.53°C, power of 43.99% and time of 27.86 min for total phenolics. However, an extraction temperature of 41.60°C, power of 44.88% and time of 27.49 min was optimal for free radical scavenging activity (judged by from DPPH reduction). Further, the UAE processes were significantly better than solvent extractions without ultrasound. By electron microscopy it was concluded that ultrasonic processing caused damage in cells for all treated samples (pumpkin, peach). However, the FTIR spectra did not show any significant changes in chemical structures caused by either ultrasonic processing or solvent extraction. PMID:26885655

  8. Ultrasound Assisted Extraction of Phenolic Compounds from Peaches and Pumpkins.

    PubMed

    Altemimi, Ammar; Watson, Dennis G; Choudhary, Ruplal; Dasari, Mallika R; Lightfoot, David A

    2016-01-01

    The ultrasound-assisted extraction (UAE) method was used to optimize the extraction of phenolic compounds from pumpkins and peaches. The response surface methodology (RSM) was used to study the effects of three independent variables each with three treatments. They included extraction temperatures (30, 40 and 50°C), ultrasonic power levels (30, 50 and 70%) and extraction times (10, 20 and 30 min). The optimal conditions for extractions of total phenolics from pumpkins were inferred to be a temperature of 41.45°C, a power of 44.60% and a time of 25.67 min. However, an extraction temperature of 40.99°C, power of 56.01% and time of 25.71 min was optimal for recovery of free radical scavenging activity (measured by 1, 1-diphenyl-2-picrylhydrazyl (DPPH) reduction). The optimal conditions for peach extracts were an extraction temperature of 41.53°C, power of 43.99% and time of 27.86 min for total phenolics. However, an extraction temperature of 41.60°C, power of 44.88% and time of 27.49 min was optimal for free radical scavenging activity (judged by from DPPH reduction). Further, the UAE processes were significantly better than solvent extractions without ultrasound. By electron microscopy it was concluded that ultrasonic processing caused damage in cells for all treated samples (pumpkin, peach). However, the FTIR spectra did not show any significant changes in chemical structures caused by either ultrasonic processing or solvent extraction. PMID:26885655

  9. Superparamagnetic Fe3O4 nanoparticles as catalysts for the catalytic oxidation of phenolic and aniline compounds.

    PubMed

    Zhang, Shengxiao; Zhao, Xiaoli; Niu, Hongyun; Shi, Yali; Cai, Yaqi; Jiang, Guibin

    2009-08-15

    Fe(3)O(4) magnetic nanoparticles (MNPs) with diameters about 10nm were synthesized successfully and used to remove phenol and aniline from aqueous solution. The results showed that phenol and aniline could be eliminated easily from solution under acidic and neutral conditions in the presence of MNPs and H(2)O(2). When the concentrations of Fe(3)O(4) MNPs and H(2)O(2) were 5gL(-1) and 1.2M, respectively, phenol and aniline could be removed completely after 6h of reaction at 308K, and the total organic carbon (TOC) abatement efficiency for phenol and aniline were 42.79% and 40.38%. Some intermediates such as formic acid, acetic acid, fumaric acid and hydroquinone were detected during reaction. Fe(3)O(4) MNPs exhibited good stability and reusability, also showed excellent catalysis ability to eliminate some substituted phenolic and aniline compounds from solution. Fe(3)O(4) MNPs had good superparamagnetism and was readily separated from solution by applying an external magnetic field. Finally we proposed that phenol and aniline might be degraded by the hydroxyl free radicals (.OH) released from H(2)O(2) in the presence of Fe(3)O(4) MNPs as catalysts.

  10. Quaternary ammonium salts intercalated α-ZrP compounds for adsorption of phenolic compounds

    NASA Astrophysics Data System (ADS)

    Wang, Hongning; Liu, Wenjin; Yao, Wei; Zhang, Ke; Zhong, Jing; Chen, Ruoyu

    2013-03-01

    By using methylamine as the colloidization agent to weaken the interactions of α-ZrP laminate, the quaternary ammonium salts of DTAB, TTAB, CTAB and STAB were successfully intercalated into the methylamine pre-pillared α-ZrP, denoted as DTAB-ZrP, TTAB-ZrP, CTAB-ZrP and STAB-ZrP, respectively. XRD, FTIR, TEM and N2 sorption were used to characterize the intercalated compounds, and the arrangements of intercalated quaternary ammonium salts within ZrP were supposed according to the results. It was shown that the interlayer distances were increased from 0.76 nm to 2.10-3.50 nm and the intercalated quaternary amine salt cationic bonded with Psbnd O- anion through electrostatic interaction. The phenolic compounds adsorption results have demonstrated that all the four intercalated compounds have good adsorption performance, and CTAB-ZrP show the highest maximum adsorption amounts of 0.90, 1.25 and 1.34 mmol g-1, for phenol, 2-chlorophenol and 2,4-dichlorophenolare, respectively. The adsorption isotherms of phenolic compounds are linear with the C0 of 2.0-6.0 mmol L-1 and fit well to both the Linear and the Freundlich models, which indicated that the adsorption mechanism is mainly partition effects of organic phase within ZrP interlayer.

  11. Immobilization of tyrosinase on modified diatom biosilica: enzymatic removal of phenolic compounds from aqueous solution.

    PubMed

    Bayramoglu, Gulay; Akbulut, Aydin; Arica, M Yakup

    2013-01-15

    Acid and plasma treated diatom-biosilica particles, were modified with 3-aminopropyl triethoxysilane (APTES), and activated with glutaraldehyde. Then, tyrosinase was immobilized onto the pre-activated biosilica by covalent bonding. The biosilica properties were determined using SEM, and FTIR. The enzyme system has been characterized as a function of pH, temperature and substrate concentration. Optimum pH of the free and immobilized enzyme was found to be pH 7.0. Optimum temperatures of the free and immobilized enzymes were determined as 35 and 45 °C respectively. The biodegradation of phenolic compounds (i.e., phenol, para-cresol and phenyl acetate) has been studied by means of immobilized tyrosinase in a batch system. The immobilized tyrosinase retained about 74% of its original activity after 10 times repeated use in the batch system. Moreover, the storage stability of the tyrosinase-biosilica system resulted excellent, since they maintained more than 67% of the initial activity after eighth week storage. Highly porous structure of biosilica can provide large surface area for immobilization of high quantity enzyme. The porous structure of the biosilica can decrease diffusion limitation both substrate phenols and their products. Finally, the immobilized tyrosinase was used in a batch system for degradation of three different phenols.

  12. The Biosynthetic Pathways of Tanshinones and Phenolic Acids in Salvia miltiorrhiza.

    PubMed

    Ma, Xiao-Hui; Ma, Ying; Tang, Jin-Fu; He, Ya-Li; Liu, Yu-Chen; Ma, Xiao-Jing; Shen, Ye; Cui, Guang-Hong; Lin, Hui-Xin; Rong, Qi-Xian; Guo, Juan; Huang, Lu-Qi

    2015-01-01

    Secondary metabolites from plants play key roles in human medicine and chemical industries. Due to limited accumulation of secondary metabolites in plants and their important roles, characterization of key enzymes involved in biosynthetic pathway will enable metabolic engineering or synthetic biology to improve or produce the compounds in plants or microorganisms, which provides an alternative for production of these valuable compounds. Salvia miltiorrhiza, containing tanshinones and phenolic acids as its active compounds, has been widely used for the treatment of cardiovascular and cerebrovascular diseases. The biosynthetic analysis of secondary metabolites in S. miltiorrhiza has made great progress due to the successful genetic transformation system, simplified hairy roots system, and high-throughput sequencing. The cloned genes in S. miltiorrhiza had provided references for functional characterization of the post-modification steps involved in biosynthesis of tanshinones and phenolic acids, and further utilization of these steps in metabolic engineering. The strategies used in these studies could provide solid foundation for elucidation of biosynthetic pathways of diterpenoids and phenolic acids in other species. The present review systematically summarizes recent advances in biosynthetic pathway analysis of tanshinones and phenolic acids as well as synthetic biology and metabolic engineering applications of the rate-limiting genes involved in the secondary metabolism in S. miltiorrhiza. PMID:26370949

  13. Determination of total phenolic compounds in compost by infrared spectroscopy.

    PubMed

    Cascant, M M; Sisouane, M; Tahiri, S; Krati, M El; Cervera, M L; Garrigues, S; de la Guardia, M

    2016-06-01

    Middle and near infrared (MIR and NIR) were applied to determine the total phenolic compounds (TPC) content in compost samples based on models built by using partial least squares (PLS) regression. The multiplicative scatter correction, standard normal variate and first derivative were employed as spectra pretreatment, and the number of latent variable were optimized by leave-one-out cross-validation. The performance of PLS-ATR-MIR and PLS-DR-NIR models was evaluated according to root mean square error of cross validation and prediction (RMSECV and RMSEP), the coefficient of determination for prediction (Rpred(2)) and residual predictive deviation (RPD) being obtained for this latter values of 5.83 and 8.26 for MIR and NIR, respectively. PMID:27130128

  14. Electron transfer reactions of osmium(II) complexes with phenols and phenolic acids

    NASA Astrophysics Data System (ADS)

    Rajeswari, Angusamy; Ramdass, Arumugam; Muthu Mareeswaran, Paulpandian; Velayudham, Murugesan; Rajagopal, Seenivasan

    2016-07-01

    Three [Os(NN)3]2+ complexes (NN = polypyridine) with ligands of varying hydrophobicity were synthesized and characterized by NMR spectral techniques. The geometry of the molecules are optimized by DFT calculations. The interaction between [Os(NN)3]2+ complexes and phenolate ion in ground state is confirmed by absorption spectral study and the binding constant values are in the range of 3-740 M-1. The photoinduced electron transfer reaction of these [Os(NN)3]2+ complexes with phenols and phenolic acids at pH 12.5 leads to the formation of phenoxyl radical confirmed through transient absorption spectral study. Binding constants and electron transfer rate constants within the [Os(NN)3]2+-phenolate ion adduct account for the change for the overall quenching constant with the change of structure of reactants.

  15. Olive Tree (Olea europeae L.) Leaves: Importance and Advances in the Analysis of Phenolic Compounds

    PubMed Central

    Abaza, Leila; Taamalli, Amani; Nsir, Houda; Zarrouk, Mokhtar

    2015-01-01

    Phenolic compounds are becoming increasingly popular because of their potential role in contributing to human health. Experimental evidence obtained from human and animal studies demonstrate that phenolic compounds from Olea europaea leaves have biological activities which may be important in the reduction in risk and severity of certain chronic diseases. Therefore, an accurate profiling of phenolics is a crucial issue. In this article, we present a review work on current treatment and analytical methods used to extract, identify, and/or quantify phenolic compounds in olive leaves. PMID:26783953

  16. Comparison of microwave and ultrasound-assisted extraction techniques for leaching of phenolic compounds from nettle.

    PubMed

    Ince, Alev Emine; Sahin, Serpil; Sumnu, Gulum

    2014-10-01

    In this study, extraction of phenolic compounds from nettle by microwave and ultrasound was studied. In both microwave and ultrasound-assisted extractions, effects of extraction time (5-20 min for microwave; 5-30 min for ultrasound) and solid to solvent ratio (1:10, 1:20, and 1:30 g/mL) on total phenolic content (TPC) were investigated. Effects of different powers (50 % and 80 %) were also studied for ultrasound-assisted extraction. In microwave-assisted extraction, the optimum TPC of the extracts (24.64 ± 2.36 mg GAE/g dry material) was obtained in 10 min and at 1:30 solid to solvent ratio. For ultrasound-assisted extraction, the condition that gave the highest TPC (23.86 ± 1.92 mg GAE/g dry material) was 30 min, 1:30 solid to solvent ratio, and 80 % power. Extracts obtained at the optimum conditions of microwave and ultrasound were compared in terms of TPC, antioxidant activity (AA) and concentration of phenolic acids with conventional extraction and maceration, respectively. Microwave reduced extraction time by 67 %. AA of extracts varied between 2.95 ± 0.01 and 4.48 ± 0.03 mg DPPH/g dry material among four methods. Major phenolic compounds were determined as naringenin and chlorogenic acid in nettle. PMID:25328225

  17. Stability and metabolism of Arbutus unedo bioactive compounds (phenolics and antioxidants) under in vitro digestion and colonic fermentation.

    PubMed

    Mosele, Juana I; Macià, Alba; Romero, Mari-Paz; Motilva, María-José

    2016-06-15

    The natural antioxidants of Arbutus unedo highlight the importance of this fruit as natural source of bioactive compounds. In the present study, to evaluate the stability of phenolic compounds, ascorbic acid and fat-soluble antioxidants (α-tocopherol, β-carotene and lutein), in vitro gastrointestinal digestion was applied to A. unedo fruit. After that, the non-absorbable fraction was anaerobically incubated with human faeces and the metabolic pathway for gallotannins, ellagitannins, flavan-3-ols and anthocyanins from A. unedo fruit was proposed. The results showed that the presence of pectin from the fruit hampered the solubilization of the phenolic compounds (with exception of gallic and ellagic acids) and fat-soluble vitamins during gastric digestion. Degradation of pectin-gel during the duodenal digestion favored the release of the phenolic compounds and fat-soluble antioxidants to the media. The catabolic activity of human microbiota led to the generation of a wide range of simple phenols, such as p-hydroxybenzoic acid and catechol, derived from the catabolism of gallotannins, ellagitannins, flavan-3-ols and anthocyanins.

  18. Stability and metabolism of Arbutus unedo bioactive compounds (phenolics and antioxidants) under in vitro digestion and colonic fermentation.

    PubMed

    Mosele, Juana I; Macià, Alba; Romero, Mari-Paz; Motilva, María-José

    2016-06-15

    The natural antioxidants of Arbutus unedo highlight the importance of this fruit as natural source of bioactive compounds. In the present study, to evaluate the stability of phenolic compounds, ascorbic acid and fat-soluble antioxidants (α-tocopherol, β-carotene and lutein), in vitro gastrointestinal digestion was applied to A. unedo fruit. After that, the non-absorbable fraction was anaerobically incubated with human faeces and the metabolic pathway for gallotannins, ellagitannins, flavan-3-ols and anthocyanins from A. unedo fruit was proposed. The results showed that the presence of pectin from the fruit hampered the solubilization of the phenolic compounds (with exception of gallic and ellagic acids) and fat-soluble vitamins during gastric digestion. Degradation of pectin-gel during the duodenal digestion favored the release of the phenolic compounds and fat-soluble antioxidants to the media. The catabolic activity of human microbiota led to the generation of a wide range of simple phenols, such as p-hydroxybenzoic acid and catechol, derived from the catabolism of gallotannins, ellagitannins, flavan-3-ols and anthocyanins. PMID:26868556

  19. Biodegradation of phenol, salicylic acid, benzenesulfonic acid, and iomeprol by Pseudomonas fluorescens in the capillary fringe.

    PubMed

    Hack, Norman; Reinwand, Christian; Abbt-Braun, Gudrun; Horn, Harald; Frimmel, Fritz H

    2015-12-01

    Mass transfer and biological transformation phenomena in the capillary fringe were studied using phenol, salicylic acid, benzenesulfonic acid, and the iodinated X-ray contrast agent iomeprol as model organic compounds and the microorganism strain Pseudomonas fluorescens. Three experimental approaches were used: Batch experiments (uniform water saturation and transport by diffusion), in static columns (with a gradient of water saturation and advective transport in the capillaries) and in a flow-through cell (with a gradient of water saturation and transport by horizontal and vertical flow: 2-dimension flow-through microcosm). The reactors employed for the experiments were filled with quartz sand of defined particle size distribution (dp=200...600 μm, porosity ε=0.42). Batch experiments showed that phenol and salicylic acid have a high, whereas benzenesulfonic acid and iomeprol have a quite low potential for biodegradation under aerobic conditions and in a matrix nearly close to water saturation. Batch experiments under anoxic conditions with nitrate as electron acceptor revealed that the biodegradation of the model compounds was lower than under aerobic conditions. Nevertheless, the experiments showed that the moisture content was also responsible for an optimized transport in the liquid phase of a porous medium. Biodegradation in the capillary fringe was found to be influenced by both the moisture content and availability of the dissolved substrate, as seen in static column experiments. The gas-liquid mass transfer of oxygen also played an important role for the biological activity. In static column experiments under aerobic conditions, the highest biodegradation was found in the capillary fringe (e.g. βt/β0 (phenol)=0 after t=6 d) relative to the zone below the water table and unsaturated zone. The highest biodegradation occurred in the flow-through cell experiment where the height of the capillary fringe was largest. PMID:26529301

  20. Biodegradation of phenol, salicylic acid, benzenesulfonic acid, and iomeprol by Pseudomonas fluorescens in the capillary fringe.

    PubMed

    Hack, Norman; Reinwand, Christian; Abbt-Braun, Gudrun; Horn, Harald; Frimmel, Fritz H

    2015-12-01

    Mass transfer and biological transformation phenomena in the capillary fringe were studied using phenol, salicylic acid, benzenesulfonic acid, and the iodinated X-ray contrast agent iomeprol as model organic compounds and the microorganism strain Pseudomonas fluorescens. Three experimental approaches were used: Batch experiments (uniform water saturation and transport by diffusion), in static columns (with a gradient of water saturation and advective transport in the capillaries) and in a flow-through cell (with a gradient of water saturation and transport by horizontal and vertical flow: 2-dimension flow-through microcosm). The reactors employed for the experiments were filled with quartz sand of defined particle size distribution (dp=200...600 μm, porosity ε=0.42). Batch experiments showed that phenol and salicylic acid have a high, whereas benzenesulfonic acid and iomeprol have a quite low potential for biodegradation under aerobic conditions and in a matrix nearly close to water saturation. Batch experiments under anoxic conditions with nitrate as electron acceptor revealed that the biodegradation of the model compounds was lower than under aerobic conditions. Nevertheless, the experiments showed that the moisture content was also responsible for an optimized transport in the liquid phase of a porous medium. Biodegradation in the capillary fringe was found to be influenced by both the moisture content and availability of the dissolved substrate, as seen in static column experiments. The gas-liquid mass transfer of oxygen also played an important role for the biological activity. In static column experiments under aerobic conditions, the highest biodegradation was found in the capillary fringe (e.g. βt/β0 (phenol)=0 after t=6 d) relative to the zone below the water table and unsaturated zone. The highest biodegradation occurred in the flow-through cell experiment where the height of the capillary fringe was largest.

  1. Biodegradation of phenol, salicylic acid, benzenesulfonic acid, and iomeprol by Pseudomonas fluorescens in the capillary fringe

    NASA Astrophysics Data System (ADS)

    Hack, Norman; Reinwand, Christian; Abbt-Braun, Gudrun; Horn, Harald; Frimmel, Fritz H.

    2015-12-01

    Mass transfer and biological transformation phenomena in the capillary fringe were studied using phenol, salicylic acid, benzenesulfonic acid, and the iodinated X-ray contrast agent iomeprol as model organic compounds and the microorganism strain Pseudomonas fluorescens. Three experimental approaches were used: Batch experiments (uniform water saturation and transport by diffusion), in static columns (with a gradient of water saturation and advective transport in the capillaries) and in a flow-through cell (with a gradient of water saturation and transport by horizontal and vertical flow: 2-dimension flow-through microcosm). The reactors employed for the experiments were filled with quartz sand of defined particle size distribution (dp = 200…600 μm, porosity ε = 0.42). Batch experiments showed that phenol and salicylic acid have a high, whereas benzenesulfonic acid and iomeprol have a quite low potential for biodegradation under aerobic conditions and in a matrix nearly close to water saturation. Batch experiments under anoxic conditions with nitrate as electron acceptor revealed that the biodegradation of the model compounds was lower than under aerobic conditions. Nevertheless, the experiments showed that the moisture content was also responsible for an optimized transport in the liquid phase of a porous medium. Biodegradation in the capillary fringe was found to be influenced by both the moisture content and availability of the dissolved substrate, as seen in static column experiments. The gas-liquid mass transfer of oxygen also played an important role for the biological activity. In static column experiments under aerobic conditions, the highest biodegradation was found in the capillary fringe (e.g. βt/β0 (phenol) = 0 after t = 6 d) relative to the zone below the water table and unsaturated zone. The highest biodegradation occurred in the flow-through cell experiment where the height of the capillary fringe was largest.

  2. Analysis of phenolic compounds in Matricaria chamomilla and its extracts by UPLC-UV.

    PubMed

    Haghi, G; Hatami, A; Safaei, A; Mehran, M

    2014-01-01

    Chamomile (Matricaria chamomilla L.) is a widely used medicinal plant possessing several pharmacological effects due to presence of active compounds. This study describes a method of using ultra performance liquid chromatography (UPLC) coupled with photodiode array (PDA) detector for the separation of phenolic compounds in M. chamomilla and its crude extracts. Separation was conducted on C18 column (150 mm × 2 mm, 1.8 μm) using a gradient elution with a mobile phase consisting of acetonitrile and 4% aqueous acetic acid at 25°C. The method proposed was validated for determination of free and total apigenin and apigenin 7-glucoside contents as bioactive compounds in the extracts by testing sensitivity, linearity, precision and recovery. In general, UPLC produced significant improvements in method sensitivity, speed and resolution. Extraction was performed with methanol, 70% aqueous ethanol and water solvents. Total phenolic and total flavonoid contents ranged from 1.77 to 50.75 gram (g) of gallic acid equivalent (GAE)/100 g and 0.82 to 36.75 g quercetin equivalent (QE)/100 g in dry material, respectively. There was a considerable difference from 40 to 740 mg/100 g for apigenin and 210 to 1110 mg/100 g for apigenin 7-glucoside in dry material. PMID:25598797

  3. Tissue-specific, development-dependent phenolic compounds accumulation profile and gene expression pattern in tea plant [Camellia sinensis].

    PubMed

    Jiang, Xiaolan; Liu, Yajun; Li, Weiwei; Zhao, Lei; Meng, Fei; Wang, Yunsheng; Tan, Huarong; Yang, Hua; Wei, Chaoling; Wan, Xiaochun; Gao, Liping; Xia, Tao

    2013-01-01

    Phenolic compounds in tea plant [Camellia sinensis (L.)] play a crucial role in dominating tea flavor and possess a number of key pharmacological benefits on human health. The present research aimed to study the profile of tissue-specific, development-dependent accumulation pattern of phenolic compounds in tea plant. A total of 50 phenolic compounds were identified qualitatively using liquid chromatography in tandem mass spectrometry technology. Of which 29 phenolic compounds were quantified based on their fragmentation behaviors. Most of the phenolic compounds were higher in the younger leaves than that in the stem and root, whereas the total amount of proanthocyanidins were unexpectedly higher in the root. The expression patterns of 63 structural and regulator genes involved in the shikimic acid, phenylpropanoid, and flavonoid pathways were analyzed by quantitative real-time polymerase chain reaction and cluster analysis. Based on the similarity of their expression patterns, the genes were classified into two main groups: C1 and C2; and the genes in group C1 had high relative expression level in the root or low in the bud and leaves. The expression patterns of genes in C2-2-1 and C2-2-2-1 groups were probably responsible for the development-dependent accumulation of phenolic compounds in the leaves. Enzymatic analysis suggested that the accumulation of catechins was influenced simultaneously by catabolism and anabolism. Further research is recommended to know the expression patterns of various genes and the reason for the variation in contents of different compounds in different growth stages and also in different organs.

  4. Tissue-Specific, Development-Dependent Phenolic Compounds Accumulation Profile and Gene Expression Pattern in Tea Plant [Camellia sinensis

    PubMed Central

    Li, Weiwei; Zhao, Lei; Meng, Fei; Wang, Yunsheng; Tan, Huarong; Yang, Hua; Wei, Chaoling; Wan, Xiaochun; Gao, Liping; Xia, Tao

    2013-01-01

    Phenolic compounds in tea plant [Camellia sinensis (L.)] play a crucial role in dominating tea flavor and possess a number of key pharmacological benefits on human health. The present research aimed to study the profile of tissue-specific, development-dependent accumulation pattern of phenolic compounds in tea plant. A total of 50 phenolic compounds were identified qualitatively using liquid chromatography in tandem mass spectrometry technology. Of which 29 phenolic compounds were quantified based on their fragmentation behaviors. Most of the phenolic compounds were higher in the younger leaves than that in the stem and root, whereas the total amount of proanthocyanidins were unexpectedly higher in the root. The expression patterns of 63 structural and regulator genes involved in the shikimic acid, phenylpropanoid, and flavonoid pathways were analyzed by quantitative real-time polymerase chain reaction and cluster analysis. Based on the similarity of their expression patterns, the genes were classified into two main groups: C1 and C2; and the genes in group C1 had high relative expression level in the root or low in the bud and leaves. The expression patterns of genes in C2-2-1 and C2-2-2-1 groups were probably responsible for the development-dependent accumulation of phenolic compounds in the leaves. Enzymatic analysis suggested that the accumulation of catechins was influenced simultaneously by catabolism and anabolism. Further research is recommended to know the expression patterns of various genes and the reason for the variation in contents of different compounds in different growth stages and also in different organs. PMID:23646127

  5. Influence of growing season on phenolic compounds and antioxidant properties of grape berries from vines grown in subtropical climate.

    PubMed

    Xu, Changmou; Zhang, Yali; Zhu, Lei; Huang, Yu; Lu, Jiang

    2011-02-23

    The influence of growing season (winter vs summer) on the synthesis and accumulation of phenolic compounds and antioxidant properties was studied in five grape cultivars for three consecutive years. Four phenolic compound parameters (total phenols, flavonoids, flavan-3-ols, and anthocyanins) and three antioxidant property parameters [2,2-diphenyl-1-picrylhydrazyl radical scavenging, 2,2-azinobis(3-ethylbenzothiazolinesulfonic acid) radical scavenging, and ferric reducing antioxidant power] were investigated. Results showed that both phenolic compounds and antioxidant properties in the seed and skin of winter berries were significantly (p < 0.05) higher than those of summer berries for all of the cultivars investigated. The anthocyanin profiles of berry skins appeared to be extremely consistent in different years for the same crop, whereas they varied greatly between the two crops within the same year (winter vs summer). Winter berries contained richer glucosides of delphinidin, cyanidin, peonidin, and malvidin than summer berries. These seasonal variations of phenolic compounds and antioxidant properties on grape berries were largely contributed by climatic factors such as temperature, solar radiation, rainfall, and hydrothermic coefficient between different growing seasons.

  6. Removal of furan and phenolic compounds from simulated biomass hydrolysates by batch adsorption and continuous fixed-bed column adsorption methods.

    PubMed

    Lee, Sang Cheol; Park, Sunkyu

    2016-09-01

    It has been proposed to remove all potential inhibitors and sulfuric acid in biomass hydrolysates generated from dilute-acid pretreatment of biomass, based on three steps of sugar purification process. This study focused on its first step in which furan and phenolic compounds were selectively removed from the simulated hydrolysates using activated charcoal. Batch adsorption experiments demonstrated that the affinity of activated charcoal for each component was highest in the order of vanillic acid, 4-hydroxybenzoic acid, furfural, acetic acid, sulfuric acid, and xylose. The affinity of activated charcoal for furan and phenolic compounds proved to be significantly higher than that of the other three components. Four separation strategies were conducted with a combination of batch adsorption and continuous fixed-bed column adsorption methods. It was observed that xylose loss was negligible with near complete removal of furan and phenolic compounds, when at least one fixed-bed column adsorption was implemented in the strategy. PMID:27289057

  7. Effect of processing, fermentation, and aging treatment to content and profile of phenolic compounds in soybean seed, soy curd and soy paste.

    PubMed

    Chung, Ill-Min; Seo, Su-Hyun; Ahn, Joung-Kuk; Kim, Seung-Hyun

    2011-08-01

    This study reports the effect of processing, fermentation, and aging treatment on the content and profile of 43 phenolic compounds in soybean seeds, soy curd (tofu), and soy paste (ChungGukJang, CGJ). Mean content of phenolic compounds was ranked as soybean seed=CGJ aged for 3days (CGJ-3D)=CGJ aged for 6days (CGJ-6D)>tofu (P<0.0001). Low percent recovery (47.1%) of phenolic compounds in tofu was due to heating (boiling), leaching in water, filtering, coagulation, and whey exclusion during tofu making. Aging period did not affect the mean contents of 43 phenolic compounds in the CGJ, whereas it affected the phenolic acids contents in the CGJ (P<0.01). Benzoic, ferulic, chlorogenic, gentisic, protocatechuic, or β-Resorculic acid was major phenolic compounds in soybean seeds, tofu, CGJ-3D, or CGJ-6D. Especially, the CGJ-3D contained large amounts of isoflavone aglucons and phenolic acids compared to soybean seeds or tofu.

  8. Walnut (Juglans regia L.) leaves: phenolic compounds, antibacterial activity and antioxidant potential of different cultivars.

    PubMed

    Pereira, José Alberto; Oliveira, Ivo; Sousa, Anabela; Valentão, Patrícia; Andrade, Paula B; Ferreira, Isabel C F R; Ferreres, Federico; Bento, Albino; Seabra, Rosa; Estevinho, Letícia

    2007-11-01

    Different cultivars of walnut (Juglans regia L.) leaves (Cv. Lara, Franquette, Mayette, Marbot, Mellanaise and Parisienne) grown in Portugal, were investigated in what concerns phenolic compounds and antimicrobial and antioxidant properties. Phenolics analysis was performed by reversed-phase HPLC/DAD and 10 compounds were identified and quantified: 3- and 5-caffeoylquinic acids, 3- and 4-p-coumaroylquinic acids, p-coumaric acid, quercetin 3-galactoside, quercetin 3-pentoside derivative, quercetin 3-arabinoside, quercetin 3-xyloside and quercetin 3-rhamnoside. The antimicrobial capacity was screened against Gram positive (Bacillus cereus, B. subtilis, Staphylococcus aureus) and Gram negative bacteria (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae) and fungi (Candida albicans, Cryptococcus neoformans). Walnut leaves selectively inhibited the growth of Gram positive bacteria, being B. cereus the most susceptible one (MIC 0.1mg/mL). Gram negative bacteria and fungi were resistant to the extracts at 100mg/mL. Lara walnut leaves were also submitted to antibacterial assays using 18 clinical isolates of Staphylococcus sp. Antioxidant activity was accessed by the reducing power assay, the scavenging effect on DPPH (2,2-diphenyl-1-picrylhydrazyl) radicals and beta-carotene linoleate model system. In a general way, all of the studied walnut leaves cultivars presented high antioxidant activity (EC(50) values lower than 1mg/mL), being Cv. Lara the most effective one.

  9. Walnut (Juglans regia L.) leaves: phenolic compounds, antibacterial activity and antioxidant potential of different cultivars.

    PubMed

    Pereira, José Alberto; Oliveira, Ivo; Sousa, Anabela; Valentão, Patrícia; Andrade, Paula B; Ferreira, Isabel C F R; Ferreres, Federico; Bento, Albino; Seabra, Rosa; Estevinho, Letícia

    2007-11-01

    Different cultivars of walnut (Juglans regia L.) leaves (Cv. Lara, Franquette, Mayette, Marbot, Mellanaise and Parisienne) grown in Portugal, were investigated in what concerns phenolic compounds and antimicrobial and antioxidant properties. Phenolics analysis was performed by reversed-phase HPLC/DAD and 10 compounds were identified and quantified: 3- and 5-caffeoylquinic acids, 3- and 4-p-coumaroylquinic acids, p-coumaric acid, quercetin 3-galactoside, quercetin 3-pentoside derivative, quercetin 3-arabinoside, quercetin 3-xyloside and quercetin 3-rhamnoside. The antimicrobial capacity was screened against Gram positive (Bacillus cereus, B. subtilis, Staphylococcus aureus) and Gram negative bacteria (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae) and fungi (Candida albicans, Cryptococcus neoformans). Walnut leaves selectively inhibited the growth of Gram positive bacteria, being B. cereus the most susceptible one (MIC 0.1mg/mL). Gram negative bacteria and fungi were resistant to the extracts at 100mg/mL. Lara walnut leaves were also submitted to antibacterial assays using 18 clinical isolates of Staphylococcus sp. Antioxidant activity was accessed by the reducing power assay, the scavenging effect on DPPH (2,2-diphenyl-1-picrylhydrazyl) radicals and beta-carotene linoleate model system. In a general way, all of the studied walnut leaves cultivars presented high antioxidant activity (EC(50) values lower than 1mg/mL), being Cv. Lara the most effective one. PMID:17637491

  10. Degradation of Phenolic Compounds and Ring Cleavage of Catechol by Phanerochaete chrysosporium

    PubMed Central

    Leatham, Gary F.; Crawford, R. L.; Kirk, T. Kent

    1983-01-01

    POL-88, a mutant of the white-rot fungus Phanerochaete chrysosporium, was selected for diminished phenol-oxidizing enzyme activity. A wide variety of phenolic compounds were degraded by ligninolytic cultures of this mutant. With several o-diphenolic substrates, degradation intermediates were produced that had UV spectra consistent with muconic acids. Extensive spectrophotometric and polarographic assays failed to detect classical ring-cleaving dioxygenases in cell homogenates or in extracts from ligninolytic cultures. Even so, a sensitive carrier-trapping assay showed that intact cultures degraded [U-14C]catechol to [14C]muconic acid, establishing the presence of a system capable of 1,2-intradiol fission. Significant accumulation of [14C]muconic acid into carrier occurred only when evolution of 14CO2 from [14C]catechol was inhibited by treating cultures with excess nutrient nitrogen (e.g., l-glutamic acid) or with cycloheximide. l-Glutamic acid is known from past work to repress the ligninolytic system in P. chrysosporium and to mimic the effect of cycloheximide. The results here indicate, therefore, that the enzyme system responsible for degrading ring-cleavage products to CO2 turns over faster than does the system responsible for ring cleavage. PMID:16346340

  11. Antibacterial, Antiradical Potential and Phenolic Compounds of Thirty-One Polish Mushrooms

    PubMed Central

    Los, Renata; Malm, Anna

    2015-01-01

    Background Among many sources of natural bioactive substances, mushrooms constitute a huge and almost unexplored group. Fungal compounds have been repeatedly reported to exert biological effects which have prompted their use in pharmaceutical and cosmetic industry. Therefore, the aim of this study was analysis of chemical composition and biological activity of 31 wild growing mushroom species (including saprophytic and parasitic) from Poland. Methods Qualitative and quantitative LC-ESI-MS/MS analysis of fourteen phenolic acids in the mushrooms analysed was performed. Moreover, total phenolic content was determined by the modified Folin-Ciocalteau method. Antioxidative activity of ethanolic extracts towards DPPH• free radical was examined. Antibacterial activity against Gram-positive (S. epidermidis, S. aureus, B. subtilis, M. luteus) and Gram-negative (E. coli, K. pneumoniae, P. aeruginosa, P. mirabilis) microbial strains was analyzed. Results As a result, the first such broad report on polyphenolic composition, antiradical and antimicrobial potential of wild growing Polish mushrooms was developed. Mushroom extracts were found to contain both benzoic (protocatechuic, 4-OH-benzoic, vanillic, syringic) and cinnamic acid derivatives (caffeic, p-coumaric, ferulic). Total phenolic content in mushrooms ranged between 2.79 and 53.13 mg gallic acid equivalent /g of dried extract in Trichaptum fuscoviolaceum and Fomes fomentarius, respectively. Fungi showed much differentiated antiradical activity, from highly active F. fomentarius to poorly effective Russula fragilis (IC50 1.39 to 120.54 mg per mg DPPH•, respectively). A quite considerable relationship between phenolic content and antiradical activity has been demonstrated. Mushrooms varied widely in antimicrobial potential (MIC from 0.156 to 5 mg/ml). Generally, a slightly higher activity against Gram-positive than Gram-negative strains was observed. This is the first study concerning the chemical composition and

  12. Rapid screening of ascorbic acid, glycoalkaloids, and phenolics in potato using high-performance liquid chromatography.

    PubMed

    Shakya, Roshani; Navarre, Duroy A

    2006-07-26

    Evaluation of phenolic metabolism in potato tubers (Solanum tuberosum) would be facilitated by faster analytical methods. A high-throughput HPLC method was developed for the qualitative and quantitative determination in potato of numerous phenolic compounds, the sum of the glycoalkaloids chaconine and solanine, plus ascorbic acid. Following a fast extraction, HPLC run times of 12 min were achieved with the use of a monolithic RP C18 column. UV and MS analyses were used to characterize the phenolic complement in extracts from two white-fleshed varieties. Over 30 compounds were identified, some of which are thought to possess either nutritional value or are involved in plant disease resistance. This method is expected to be useful for germplasm mining and for varietal development programs in which large numbers of lines are generated.

  13. Biotransformation of furanic and phenolic compounds with hydrogen gas production in a microbial electrolysis cell

    DOE PAGES

    Zeng, Xiaofei; Borole, Abhijeet P.; Pavlostathis, Spyros G.

    2015-10-27

    In this study, furanic and phenolic compounds are problematic byproducts resulting from the decomposition of lignocellulosic biomass during biofuel production. This study assessed the capacity of a microbial electrolysis cell (MEC) to produce hydrogen gas (H2) using a mixture of two furanic (furfural, FF; 5-hydroxymethyl furfural, HMF) and three phenolic (syringic acid, SA; vanillic acid, VA; and 4-hydroxybenzoic acid, HBA) compounds as the sole carbon and energy source in the bioanode. The rate and extent of biotransformation of the five compounds, efficiency of H2 production, as well as the anode microbial community structure were investigated. The five compounds were completelymore » transformed within 7-day batch runs and their biotransformation rate increased with increasing initial concentration. At an initial concentration of 1,200 mg/L (8.7 mM) of the mixture of the five compounds, their biotransformation rate ranged from 0.85 to 2.34 mM/d. The anode coulombic efficiency was 44-69%, which is comparable to wastewater-fed MECs. The H2 yield varied from 0.26 to 0.42 g H2-COD/g COD removed in the anode, and the bioanode volume-normalized H2 production rate was 0.07-0.1 L/L-d. The major identified fermentation products that did not transform further were catechol and phenol. Acetate was the direct substrate for exoelectrogenesis. Current and H2 production were inhibited at an initial substrate concentration of 1,200 mg/L, resulting in acetate accumulation at a much higher level than that measured in other batch runs conducted with a lower initial concentration of the five compounds. The anode microbial community consisted of exoelectrogens, putative degraders of the five compounds, and syntrophic partners of exoelectrogens. The H2 production route demonstrated in this study has proven to be an alternative to the currently used process of reforming natural gas to supply H2 needed to upgrade bio-oils to stable hydrocarbon fuels.« less

  14. Biotransformation of furanic and phenolic compounds with hydrogen gas production in a microbial electrolysis cell

    SciTech Connect

    Zeng, Xiaofei; Borole, Abhijeet P.; Pavlostathis, Spyros G.

    2015-10-27

    In this study, furanic and phenolic compounds are problematic byproducts resulting from the decomposition of lignocellulosic biomass during biofuel production. This study assessed the capacity of a microbial electrolysis cell (MEC) to produce hydrogen gas (H2) using a mixture of two furanic (furfural, FF; 5-hydroxymethyl furfural, HMF) and three phenolic (syringic acid, SA; vanillic acid, VA; and 4-hydroxybenzoic acid, HBA) compounds as the sole carbon and energy source in the bioanode. The rate and extent of biotransformation of the five compounds, efficiency of H2 production, as well as the anode microbial community structure were investigated. The five compounds were completely transformed within 7-day batch runs and their biotransformation rate increased with increasing initial concentration. At an initial concentration of 1,200 mg/L (8.7 mM) of the mixture of the five compounds, their biotransformation rate ranged from 0.85 to 2.34 mM/d. The anode coulombic efficiency was 44-69%, which is comparable to wastewater-fed MECs. The H2 yield varied from 0.26 to 0.42 g H2-COD/g COD removed in the anode, and the bioanode volume-normalized H2 production rate was 0.07-0.1 L/L-d. The major identified fermentation products that did not transform further were catechol and phenol. Acetate was the direct substrate for exoelectrogenesis. Current and H2 production were inhibited at an initial substrate concentration of 1,200 mg/L, resulting in acetate accumulation at a much higher level than that measured in other batch runs conducted with a lower initial concentration of the five compounds. The anode microbial community consisted of exoelectrogens, putative degraders of the five compounds, and syntrophic partners of exoelectrogens. The H2 production route demonstrated in this study has proven to be an alternative to the currently used process of reforming natural gas to supply H2 needed to

  15. High-performance liquid chromatography analysis of phenolic acid, flavonoid, and phenol contents in various natural Yemeni honeys using multi-walled carbon nanotubes as a solid-phase extraction adsorbent.

    PubMed

    Badjah Hadj Ahmed, A Y; Obbed, Munir S; Wabaidur, Saikh M; AlOthman, Zeid A; Al-Shaalan, Nora H

    2014-06-18

    A simple method has been described for simultaneous determination of phenolic acid, flavonoid, and other phenol contents in various natural honey samples collected from various regions of Yemen. Multi-walled carbon nanotubes were used as a solid-phase adsorbent for extraction of the polyphenols from honey samples. The total contents of phenolic acids, flavonoids, and phenolic components of the 12 different samples were found in the range of 363-2658, 261-1646, and 224-1355 μg/100 g of honey samples, respectively. The major phenolic acid, flavonoid, and phenolic compound in these samples were found to be 4-hydroxybenzoic acid (1410 μg/100 g), chrysin (850 μg/100 g), and cinnamic acid (1336 μg/100 g), respectively. A total of 25 compounds (10 phenolic acids, 9 flavonoids, and 6 phenols) were analyzed, and a total of 24 were detected, while only 23 compounds were determined quantitatively in the honey samples. The developed method showed potential usefulness for the analysis of honey and was used for the determination of polyphenols in honey extracts.

  16. Kinetics of phenolic and phthalic acid esters biodegradation in membrane bioreactor (MBR) treating municipal landfill leachate.

    PubMed

    Boonnorat, Jarungwit; Chiemchaisri, Chart; Chiemchaisri, Wilai; Yamamoto, Kazuo

    2016-05-01

    The kinetic of phenolic and phthalic acid esters (PAEs) biodegradation in membrane bioreactor (MBR) treating municipal landfill leachate was investigated. Laboratory-scale MBR was fed with mixture of fresh and stabilized landfill leachate containing carbon to nitrogen (C/N) ratio of 10, 6, 3 and operated under different solid retention time (SRT) of 90, 15 and 5 d. Batch experiments using MBR sludge obtained from each steady-state operating condition revealed highest biodegradation rate constant (k) of 0.059-0.092 h(-1) of the phenolic and PAEs compounds at C/N of 6. Heterotrophic bacteria were the major group responsible for biodegradation of compounds whereas the presence of ammonia-oxidizing bacteria (AOB) helped accelerating their removals. Heterotrophic nitrifying bacteria found under high ammonia condition had an important role in enhancing the biodegradation of phenols and PAEs by releasing phenol hydroxylase (PH), esterase (EST) and phthalate dioxygenase (PDO) enzymes and the presence of AOB helped improving biodegradation of phenolic and PAEs compounds through their co-metabolism. PMID:26908045

  17. Potential Use of Phenolic Acids as Anti-Candida Agents: A Review

    PubMed Central

    Teodoro, Guilherme R.; Ellepola, Kassapa; Seneviratne, Chaminda J.; Koga-Ito, Cristiane Y.

    2015-01-01

    There has been a sharp rise in the occurrence of Candida infections and associated mortality over the last few years, due to the growing body of immunocompromised population. Limited number of currently available antifungal agents, undesirable side effects and toxicity, as well as emergence of resistant strains pose a considerable clinical challenge for the treatment of candidiasis. Therefore, molecules that derived from natural sources exhibiting considerable antifungal properties are a promising source for the development of novel anti-candidal therapy. Phenolic compounds isolated from natural sources possess antifungal properties of interest. Particularly, phenolic acids have shown promising in vitro and in vivo activity against Candida species. However, studies on their mechanism of action alone or in synergism with known antifungals are still scarce. This review attempts to discuss the potential use, proposed mechanisms of action and limitations of the phenolic acids in anti-candidal therapy. PMID:26733965

  18. Flavonol glycosides and other phenolic compounds in buds and leaves of different varieties of black currant (Ribes nigrum L.) and changes during growing season.

    PubMed

    Liu, Pengzhan; Kallio, Heikki; Yang, Baoru

    2014-10-01

    Phenolic compounds in buds and leaves of three varieties of black currant in Finland were identified by HPLC-DAD-ESI-MS/MS. Forty-three phenolic compounds of flavonol glycosides, proanthocyanidins and phenolic acids were found in variety "Mikael" whereas only thirty-five in "Mortti" and "Jaloste n:o 15". Glycosides of quercetin and kaempferol were the major phenolics. Rutin, hyperoside, isoquercitrin, kaempferol-3-O-rutinoise, kaempferol-3-O-glucoside, quercetin-3-O-(6″-malonyl)-glucoside and a kaempferol-malonylhexoside were the most abundant flavonol glycosides. The contents of flavonol glycosides ranged from 1 to 7 mg/g fresh weight in leaves showing typically an increasing trend from July to August, reaching the highest values in early October in "Mikael" and the end of August in "Mortti" and "Jaloste n:o 15". This is the first systematic report of the composition and content of phenolic compounds in buds and leaves of black currant.

  19. Compositional differences of phenolic compounds between black currant (Ribes nigrum L.) cultivars and their response to latitude and weather conditions.

    PubMed

    Zheng, Jie; Yang, Baoru; Ruusunen, Ville; Laaksonen, Oskar; Tahvonen, Risto; Hellsten, Jorma; Kallio, Heikki

    2012-07-01

    Phenolic compounds in black currants of three Finnish cultivars and their response to growth latitude and weather conditions were analyzed over a six-year period. 'Melalahti' had lower contents of total phenolic compounds (31.4% and 29.2% lower than 'Mortti' and 'Ola', respectively), total anthocyanins (32.6% and 30.5%), and total hydroxycinnamic acid derivatives (23.1% and 23.8%) (p < 0.05) and was less affected by growth latitude and weather conditions than 'Mortti' and 'Ola'. However, all the cultivars grown at higher latitude (66°34' N) had lower contents of total flavonols, total anthocyanins, and total phenolic compounds than those grown at lower latitude (60°23' N) (p < 0.05). The content of total hydroxycinnamic acid conjugates did not vary in 'Melalahti' (p > 0.05) but increased as the latitude increased in 'Mortti' and 'Ola' (p < 0.05). Temperature and radiation were the major weather variables influencing the composition of phenolic compounds. Delphinidin-3-O-glucoside, delphinidin-3-O-rutinoside, and myricetin-3-O-glucoside content showed positive correlations with temperature and radiation in all three cultivars. The study gives important guidelines for the selection of raw materials and growth sites as well as for the berry cultivation for commercial exploitation of black currant berries.

  20. Antidiabetic Effects of Simple Phenolic Acids: A Comprehensive Review.

    PubMed

    Vinayagam, Ramachandran; Jayachandran, Muthukumaran; Xu, Baojun

    2016-02-01

    Diabetes mellitus (DM) has become a major public health threat across the globe. Current antidiabetic therapies are based on synthetic drugs that very often have side effects. It has been widely acknowledged that diet plays an important role in the management of diabetes. Phenolic acids are widely found in daily foods such as fruits, vegetables, cereals, legumes, and wine and they provide biological, medicinal, and health properties. Simple phenolic acids have been shown to increase glucose uptake and glycogen synthesis, improve glucose and lipid profiles of certain diseases (obesity, cardiovascular diseases, DM, and its complication). The current review is an attempt to list out the antidiabetic effects of simple phenolic acids from medicinal plants and botanical foods. PMID:26634804

  1. Addition of Phenols Compounds to Meat Dough Intended for Salami Manufacture and its Antioxidant Effect

    PubMed Central

    Fasolato, Luca; Cardazzo, Barbara; Carraro, Lisa; Taticchi, Agnese; Balzan, Stefania

    2014-01-01

    A purified extract of phenols compounds (65% of phenolic content of which decarboxymethyl oleuropein aglycone represented 45% of the wet mass) obtained from vegetation water (a by-product of oil mill) was added to a ground meat dough intended for salami manufacture in two concentration levels: 75 and 150 mg/100 g of dough (F1 and F2, respectively). The control batch was composed of lean and fat cuts of pork in 70:30 ratio, 2.7% salt and a mixed starter culture of staphylococci and pediococci. After stuffing into natural casings, salamis were aged until they reached a total weight loss of 30%. The product was then sliced and packaged in a protective atmosphere (nitrogen:carbon dioxide 80:20) and placed in a refrigerator thermostat (2-4°C) with alternating 12 h of artificial light and darkness. The samples were analysed for the measurement of pH, water activity, organic acidity, peroxide number and secondary products of lipid peroxidation at the time of slicing and after 10, 20 and 30 days of storage into the refrigerated thermostat. The pH and water activity were not substantially different between the control and the two enriched batches. The peroxide number and secondary products of lipid peroxidation values in the two batches with phenols were at least substantially lower than the control sample. In conclusion, the phenol compounds obtained from vegetation water have shown no interference with the ripening process while protecting the dough from oxidation. PMID:27800353

  2. Effects of pectinase clarification treatment on phenolic compounds of pummelo (Citrus grandis l. Osbeck) fruit juice.

    PubMed

    Shah, Nor Nadiah Abdul Karim; Rahman, Russly Abdul; Shamsuddin, Rosnah; Adzahan, Noranizan Mohd

    2015-08-01

    The purpose of this study is to investigate the changes occured on phenolic compounds between two Malaysian varieties of pummelo fruit juice: Ledang (PO55) and Tambun (PO52) post-enzymatic clarification. The changes in polyphenols composition were monitored using High Performance Liquid Chromatography Diode Array Detection and Folin Ciocalteu's method. Clarification treatment of pummelo fruit juice with a commercial pectinase was optimized based on incubation temperature, time and enzyme concentration. Both varieties of pummelo fruit juice were treated with different optimized variables which produced the highest clarities with the least effect to the juice physical quality. Tambun variety was found to have significantly more total phenolic compounds (p <0.05) in comparison to Ledang variety, possibly due to the amount of naringin. Three types of hydroxycinnamic acids (chlorogenic, caffeic and coumaric acid) and three compounds of flavanones (naringin, hesperidin and narirutin) were found in both fruit juices, where naringin and chlorogenic acid were the major contributor to the total phenolic content. Naringin, which gave out bitter aftertaste to the juice, was found to decrease, 1.6 and 0.59 % reduction in Ledang and Tambun respectively, post-enzymatic treatment. The decrease in naringin, albeit nominal, could be a potential benefit to the juice production in reducing the bitterness of the juice. Post-enzymatic analysis furthermore resulted in no significance differences (p <0.05) on the total phenolic compounds of both varieties. This study in summary provides a compositional database for Malaysian pummelo fruit juice of various phenolic compounds, which can provide useful information for evaluating the authenticity and the health benefits from the juice. PMID:26243926

  3. Effects of pectinase clarification treatment on phenolic compounds of pummelo (Citrus grandis l. Osbeck) fruit juice.

    PubMed

    Shah, Nor Nadiah Abdul Karim; Rahman, Russly Abdul; Shamsuddin, Rosnah; Adzahan, Noranizan Mohd

    2015-08-01

    The purpose of this study is to investigate the changes occured on phenolic compounds between two Malaysian varieties of pummelo fruit juice: Ledang (PO55) and Tambun (PO52) post-enzymatic clarification. The changes in polyphenols composition were monitored using High Performance Liquid Chromatography Diode Array Detection and Folin Ciocalteu's method. Clarification treatment of pummelo fruit juice with a commercial pectinase was optimized based on incubation temperature, time and enzyme concentration. Both varieties of pummelo fruit juice were treated with different optimized variables which produced the highest clarities with the least effect to the juice physical quality. Tambun variety was found to have significantly more total phenolic compounds (p <0.05) in comparison to Ledang variety, possibly due to the amount of naringin. Three types of hydroxycinnamic acids (chlorogenic, caffeic and coumaric acid) and three compounds of flavanones (naringin, hesperidin and narirutin) were found in both fruit juices, where naringin and chlorogenic acid were the major contributor to the total phenolic content. Naringin, which gave out bitter aftertaste to the juice, was found to decrease, 1.6 and 0.59 % reduction in Ledang and Tambun respectively, post-enzymatic treatment. The decrease in naringin, albeit nominal, could be a potential benefit to the juice production in reducing the bitterness of the juice. Post-enzymatic analysis furthermore resulted in no significance differences (p <0.05) on the total phenolic compounds of both varieties. This study in summary provides a compositional database for Malaysian pummelo fruit juice of various phenolic compounds, which can provide useful information for evaluating the authenticity and the health benefits from the juice.

  4. Sulfonic acid resin-catalyzed addition of phenols, carboxylic acids, and water to olefins: Model reactions for catalytic upgrading of bio-oil.

    PubMed

    Zhang, Zhi-Jun; Wang, Qing-Wen; Yang, Xu-Lai; Chatterjee, Sabornie; Pittman, Charles U

    2010-05-01

    Acid-catalyzed 1-octene reactions with phenol and mixtures of phenol with water, acetic acid and 1-butanol were studied as partial bio-oil upgrading models. Bio-oil from fast biomass pyrolysis has poor fuel properties due to the presence of substantial amounts of water, carboxylic acid, phenolic derivatives and other hydroxyl-containing compounds. Additions across olefins offer a route to simultaneously lower water content and acidity while increasing hydrophobicity, stability and heating value. Amberlyst15, Dowex50WX2 and Dowex50WX4 effectively catalyzed phenol O- and C-alkylation from 65 to 120 degrees C, giving high O-alkylation selectivities in the presence of water, acetic acid and 1-butanol. Octanols and dioctyl ethers were formed from water and octyl acetates and phenol acetates from acetic acid. Phenol alkylation slowed in the presence of water. Dowex50WX2 and Dowex50WX4 were more stable in the presence of water than Amberlyst15 and were successfully recycled. Adding 1-butanol to phenol/water/1-octene, gave emulsion-like mixtures which improved phenol conversion and olefin hydration.

  5. Wastes generated during the storage of extra virgin olive oil as a natural source of phenolic compounds.

    PubMed

    Lozano-Sánchez, Jesus; Giambanelli, Elisa; Quirantes-Piné, Rosa; Cerretani, Lorenzo; Bendini, Alessandra; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto

    2011-11-01

    Phenolic compounds in extra virgin olive oil (EVOO) have been associated with beneficial effects for health. Indeed, these compounds exert strong antiproliferative effects on many pathological processes, which has stimulated chemical characterization of the large quantities of wastes generated during olive oil production. In this investigation, the potential of byproducts generated during storage of EVOO as a natural source of antioxidant compounds has been evaluated using solid-liquid and liquid-liquid extraction processes followed by rapid resolution liquid chromatography (RRLC) coupled to electrospray time-of-flight and ion trap mass spectrometry (TOF/IT-MS). These wastes contain polyphenols belonging to different classes such as phenolic acids and alcohols, secoiridoids, lignans, and flavones. The relationship between phenolic and derived compounds has been tentatively established on the basis of proposed degradation pathways. Finally, qualitative and quantitative characterizations of solid and aqueous wastes suggest that these byproducts can be considered an important natural source of phenolic compounds, mainly hydroxytyrosol, tyrosol, decarboxymethyl oleuropein aglycone, and luteolin, which, after suitable purification, could be used as food antioxidants or as ingredients in nutraceutical products due to their interesting technological and pharmaceutical properties.

  6. Artichoke and milk thistle pills and syrups as sources of phenolic compounds with antimicrobial activity.

    PubMed

    Pereira, Carla; Barros, Lillian; José Alves, Maria; Santos-Buelga, Celestino; Ferreira, Isabel C F R

    2016-07-13

    Dietary supplements based on hepatoprotective plants have been increasingly used in the prevention of liver injuries. In the present work, the aim was to study the phenolic profile and possibly relate it to the in vitro antimicrobial activity of two different formulations (pills and syrups) of artichoke and milk thistle, the antioxidant and anti-hepatocellular carcinoma activities of which were previously reported by our research group. The phenolic profiles were obtained by HPLC-DAD-ESI/MS, and the antimicrobial activity evaluation was performed with the clinical isolates of multiresistant bacteria (Escherichia coli, extended spectrum β-lactamases (ESBL) producing Escherichia coli, Proteus mirabilis, methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa). Artichoke syrup revealed the presence of vanillic acid and luteolin-7-O-glucoside while the pills possessed higher concentrations of 4-O-caffeoylquinic, 5-O-caffeoylquinic and 1,3-O-dicaffeoylquinic acids, this latest being able to inhibit the growth of MRSA. Regarding milk thistle formulations, the syrup presented isorhamnetin-O-deoxyhexoside-O-dihexoside, isorhamnetin-O-deoxyhexoside-O-hexoside and isorhamnetin-3-O-rutinoside as the major phenolic constituents whereas the pills were richer in taxifolin, silymarin derivatives and hydroxylated silibinin; the syrup revealed antimicrobial activity against all the studied bacteria with the exception of Proteus mirabilis whereas the pills revealed activity against ESBL producing Escherichia coli. Overall, all of the studied formulations revealed to be a good source of phenolic compounds, among which milk thistle syrup presented the highest variety and concentration of flavonoids, which is possibly related to its strongest antimicrobial activity.

  7. Artichoke and milk thistle pills and syrups as sources of phenolic compounds with antimicrobial activity.

    PubMed

    Pereira, Carla; Barros, Lillian; José Alves, Maria; Santos-Buelga, Celestino; Ferreira, Isabel C F R

    2016-07-13

    Dietary supplements based on hepatoprotective plants have been increasingly used in the prevention of liver injuries. In the present work, the aim was to study the phenolic profile and possibly relate it to the in vitro antimicrobial activity of two different formulations (pills and syrups) of artichoke and milk thistle, the antioxidant and anti-hepatocellular carcinoma activities of which were previously reported by our research group. The phenolic profiles were obtained by HPLC-DAD-ESI/MS, and the antimicrobial activity evaluation was performed with the clinical isolates of multiresistant bacteria (Escherichia coli, extended spectrum β-lactamases (ESBL) producing Escherichia coli, Proteus mirabilis, methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa). Artichoke syrup revealed the presence of vanillic acid and luteolin-7-O-glucoside while the pills possessed higher concentrations of 4-O-caffeoylquinic, 5-O-caffeoylquinic and 1,3-O-dicaffeoylquinic acids, this latest being able to inhibit the growth of MRSA. Regarding milk thistle formulations, the syrup presented isorhamnetin-O-deoxyhexoside-O-dihexoside, isorhamnetin-O-deoxyhexoside-O-hexoside and isorhamnetin-3-O-rutinoside as the major phenolic constituents whereas the pills were richer in taxifolin, silymarin derivatives and hydroxylated silibinin; the syrup revealed antimicrobial activity against all the studied bacteria with the exception of Proteus mirabilis whereas the pills revealed activity against ESBL producing Escherichia coli. Overall, all of the studied formulations revealed to be a good source of phenolic compounds, among which milk thistle syrup presented the highest variety and concentration of flavonoids, which is possibly related to its strongest antimicrobial activity. PMID:27273551

  8. Influence of hot water dip on fruit quality, phenolic compounds and antioxidant capacity of Satsuma mandarin during storage.

    PubMed

    Shen, Yan; Zhong, Liezhou; Sun, Yujing; Chen, Jianchu; Liu, Donghong; Ye, Xingqian

    2013-12-01

    The influence of hot water dips (50, 52 and 54  for 3 min) on fruit quality, phenolic compounds and antioxidant capacity of Satsuma mandarin during 60 days' storage at 10  was investigated. Hot water dips did not affect fruit quality attributes as well as ascorbic acid content, and 50  treatment significantly reduced fruit weight loss. Significant increases of flavonoids were found in all hot water treated fruit from after treatments till 15 days of storage, whereas phenolic acids were not greatly affected. Hot water dipping at 50  significantly increased total phenolics and antioxidant capacity of Satsuma mandarin immediately after treatment and maintained similar levels with control during storage, while 52 and 54  treatments showed relatively lower levels. The results suggested that hot water dipping at 50  for 3 min can be a promising way to retain functional quality of storing Satsuma mandarin.

  9. Phenolic compounds in five Epilobium species collected from Estonia.

    PubMed

    Remmel, Indrek; Vares, Lauri; Toom, Lauri; Matto, Vallo; Raal, Ain

    2012-10-01

    Epilobium species have been traditionally used as medicinal plants to treat benign prostate hyperplasia. The present study investigated the content of polyphenols, tannins, and flavonoids in Epilobium parviflorum Schreb., E. hirsutum L., E. adenocaulon Hausskn., E. montanum L., and E. palustre L. growing in Estonia. The total contents of polyphenols, tannins, and flavonoids were studied using UV spectroscopy with subsequent HPLC quantification of gallic acid, ellagic acid, and quercetin as marker compounds. All roots, stems, leaves, and flowers of the plants investigated contained comparable amounts of polyphenols, tannins, and flavonoids. There was a clear positive correlation between the contents of tannins and flavonoids in various plant parts. The content of these biologically active compounds suggests the use of E. parviflorum, E. hirsutum, E. adenocaulon, E. montanum, and E. palustre collected from Estonia as herbs both individually or as a blend. PMID:23156999

  10. Effects of lactone, ketone, and phenolic compounds on methane production and metabolic intermediates during anaerobic digestion.

    PubMed

    Wikandari, Rachma; Sari, Noor Kartika; A'yun, Qurrotul; Millati, Ria; Cahyanto, Muhammad Nur; Niklasson, Claes; Taherzadeh, Mohammad J

    2015-02-01

    Fruit waste is a potential feedstock for biogas production. However, the presence of fruit flavors that have antimicrobial activity is a challenge for biogas production. Lactones, ketones, and phenolic compounds are among the several groups of fruit flavors that are present in many fruits. This work aimed to investigate the effects of two lactones, i.e., γ-hexalactone and γ-decalactone; two ketones, i.e., furaneol and mesifurane; and two phenolic compounds, i.e., quercetin and epicatechin on anaerobic digestion with a focus on methane production, biogas composition, and metabolic intermediates. Anaerobic digestion was performed in a batch glass digester incubated at 55 °C for 30 days. The flavor compounds were added at concentrations of 0.05, 0.5, and 5 g/L. The results show that the addition of γ-decalactone, quercetin, and epicathechin in the range of 0.5-5 g/L reduced the methane production by 50 % (MIC50). Methane content was reduced by 90 % with the addition of 5 g/L of γ-decalactone, quercetin, and epicathechin. Accumulation of acetic acid, together with an increase in carbon dioxide production, was observed. On the contrary, γ-hexalactone, furaneol, and mesifurane increased the methane production by 83-132 % at a concentration of 5 g/L.

  11. Antioxidant activities, distribution of phenolics and free amino acids of Erica australis L. leaves and flowers collected in Algarve, Portugal.

    PubMed

    Nunes, Ricardo; Carvalho, Isabel S

    2013-01-01

    Leaves and flowers from Erica plant possess nutritional and medicinal properties. We determined the antioxidant activity, phenolic, flavonoid and amino acid profiles of the leaves and flowers of this plant. Total amino acid content varied from 28 to 49 and essential amino acids from 8 to 20 mg/g for flowers and leaves, respectively, with different distributions within the plant. From 16 phenolic compounds identified, delphinidin-3-glucoside, caffeic acid and cyanidin-3,5-glucoside in leaves and pelargonidin-3,5-glucoside in flowers were the compounds in highest amount, all with over 500 μg/g. Although flowers had higher contents of phenolic compounds (4000 μg/g) than leaves (3400 μg/g), they showed lower antioxidant activity, indicating that the antioxidant activity depends not only on the content of phenolics, but also on their type. This study shows that this plant has the potential to be used as an extra dietary source of amino acids and phenolic compounds and its consumption may provide health benefits.

  12. Changes of phenolic acids and antioxidant activities during potherb mustard (Brassica juncea, Coss.) pickling.

    PubMed

    Fang, Zhongxiang; Hu, Yuxia; Liu, Donghong; Chen, Jianchu; Ye, Xingqian

    2008-06-01

    Phenolic acids in potherb mustard (Brassica juncea, Coss.) were determined and the effects of pickling methods on the contents of total free phenolic acids, total phenolic acids, total phenolics, and antioxidant activities were investigated. Gallic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, p-coumaric acid, ferulic acid, and sinapic acid were identified in the present study. The contents of total free phenolic acids, total phenolic acids and total phenolics in fresh potherb mustard were 84.8±0.58μg/g dry weight (DW), 539±1.36μg/g DW, and 7.95±0.28mg/g DW, respectively. The total free phenolic acids increased during the pickling processes, but the total phenolic acids, total phenolics, and antioxidant activities decreased. However, after 5 weeks of fermentation, all the pickling methods retained over 70% of total phenolic contents and above 65% of antioxidant capacities. The results indicated that pickling processes were relatively good methods for the preservation of phenolic acids and antioxidants for potherb mustard. PMID:26065739

  13. Cytotoxicity of phenolic compounds on dicentrarchus labrax erythocytes

    SciTech Connect

    Boge, G.; Roche, H.

    1996-10-01

    The use of in vitro model for toxicological studies is specially appropriate to analyze the impact of molecules on well defined targets, or to study the mechanisms involved in cell toxicology. In this purpose, we previously demonstrated that marine fish erythocytes can be suitably developed as a good cell model to investigate the effects of metallic salts on membrane integrity or on detoxification enzyme activities. In contrast to mammalian red blood cells, fish erythrocytes are nucleated and well provided with subcellular organelles. In fish, these cells are directly exposed to plasma xenobiotics absorbed through gills or via the digestive tract, and/or biotransformed in liver. We applied this cell model to phenolic compounds with a special interest in the characterization of the relationship between their structure and membrane or metabolic integrity. These structure-effects relationships offer the possibility to predict the toxicity of xeonobiotics on the basis of some physico-chemical properties taken as reference. 21 refs., 1 fig., 2 tabs.

  14. Inhibition of ochratoxin A production and growth of Aspergillus species by phenolic antioxidant compounds

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The phenolic antioxidants, gallic acid, vanillic acid, protocatechuic acid, 4-hydroxybenzoic acid, catechin, caffeic acid, and chlorogenic acid were studied for their effects on ochratoxin A (OTA) production and fungal growth of ochratoxigenic Aspergilli. Of the 12 strains tested, which included A....

  15. Direct automatic determination of bitterness and total phenolic compounds in virgin olive oil using a pH-based flow-injection analysis system.

    PubMed

    Garcia-Mesa, José A; Mateos, Raquel

    2007-05-16

    Flavor and taste are sensorial attributes of virgin olive oil (VOO) highly appreciated by consumers. Among the organoleptic properties of VOO, bitterness is related to the natural phenolic compounds present in the oil. Sensorial analysis is the official method to evaluate VOO flavor and bitterness, which requires highly specialized experts. Alternatively, methods based on physicochemical determinations could be useful for the industry. The present work presents a flow-injection analysis system for the direct automatic determination of bitterness and total phenolic compounds in VOO without prior isolation, based on the spectral shift undergone by phenolic compounds upon pH variation. This system enables a complete automation of the process, including dilution of the sample and its sequential injection into buffer solutions of acidic and alkaline pH. The variation of the absorbance at 274 nm showed a high correlation with bitterness and the total phenolic content of VOO, due to the close relationship between these two parameters. Thus, the proposed method determines the bitterness and phenolic compounds, with results similar to those from reference methods (relative errors ranging from 1% to 8% for bitterness and from 2% and 7% for phenolic compounds). The precision evaluated at two levels of both parameters ranged between 0.6% and 1.5% for bitterness and between 0.7% and 2.6% for phenolic compounds.

  16. RP-HPLC analysis of phenolic acids of selected Central European Carex L. (Cyperaceae) species and its implication for taxonomy.

    PubMed

    Bogucka-Kocka, Anna; Szewczyk, Katarzyna; Janyszek, Magdalena; Janyszek, Sławomir; Cieśla, Łukasz

    2011-01-01

    Eighteen species belonging to the Carex genus were checked for the presence and the amount of eight phenolic acids (p-hydroxybenzoic, vanillic, caffeic, syringic, protocatechuic, p-coumaric, sinapic, and ferulic) by means of HPLC. Both the free and bonded phenolic acids were analyzed. The majority of the analyzed acids occurred in the studied species in relatively high amounts. The highest concentrations found were caffeic acid and p-coumaric acid, for which the detected levels were negatively correlated. A very interesting feature was the occurrence of sinapic acid, a compound very rarely detected in plant tissues. Its distribution across the analyzed set of species can be hypothetically connected with the humidity of plants' habitats. Several attempted tests of aggregative cluster analysis showed no similarity to the real taxonomical structure of the genus Carex. Thus, the phenolic acids' composition cannot be considered as the major taxonomical feature for the genus Carex.

  17. Apple juice composition: sugar, nonvolatile acid, and phenolic profiles.

    PubMed

    Lee, H S; Wrolstad, R E

    1988-01-01

    Apples from Michigan, Washington, Argentina, Mexico, and New Zealand were processed into juice; the 8 samples included Golden Delicious, Jonathan, Granny Smith, and McIntosh varieties. Liquid chromatography was used for quantitation of sugars (glucose, fructose, sucrose, and sorbitol), nonvolatile acids (malic, quinic, citric, shikimic, and fumaric), and phenolics (chlorogenic acid and hydroxymethylfurfural [HMF]). Other determinations included pH, 0Brix, and L-malic acid. A number of compositional indices for these authentic juices, e.g., chlorogenic acid content, total malic - L-malic difference, and the HMF:chlorogenic ratio, were at variance with recommended standards. The phenolic profile was shown to be particularly influenced by gelatin fining, with peak areas decreasing by as much as 50%. The L-malic:total malic ratio serves as a better index for presence of synthetic malic acid than does the difference between the 2 determinations. No apparent differences in chemical composition could be attributed to geographic origin.

  18. Cytotoxic evaluation of phenolic compounds from lichens against melanoma cells.

    PubMed

    Brandão, Luiz Fabrício Gardini; Alcantara, Glaucia Braz; Matos, Maria de Fátima Cepa; Bogo, Danielle; Freitas, Deisy dos Santos; Oyama, Nathália Mitsuko; Honda, Neli Kika

    2013-01-01

    Atranorin, lichexanthone, and the (+)-usnic, diffractaic, divaricatic, perlatolic, psoromic, protocetraric, and norstictic acids isolated from the lichens Parmotrema dilatatum (VAIN.) HALE, Usnea subcavata MOTYKA, Usnea sp., Ramalina sp., Cladina confusa (SANT.) FOLMM. & AHTI, Dirinaria aspera HÄSÄNEN, and Parmotrema lichexanthonicum ELIASARO & ADLER were evaluated against UACC-62 and B16-F10 melanoma cells and 3T3 normal cells. Sulforhodamine B assay revealed significant cytotoxic activity in protocetraric, divaricatic, and perlatolic acids on UACC-62 cells (50% growth inhibitory concentration (GI(50)) 0.52, 2.7, and 3.3 µg/mL, respectively). Divaricatic and perlatolic acids proved the most active on B16-F10 cells (GI(50) 4.4, 18.0 µg/mL, respectively) and the most cytotoxic to 3T3 normal cells. Diffractaic, usnic, norstictic, and psoromic acids were cytotoxic to UACC-62 cells in the 24.7 to 36.6 µg/mL range, as were protocetraric and diffractaic acids to B16-F10 cells (GI(50) 24.0, 25.4 µg/mL, respectively). Protocetraric acid was highly selective (selectivity index (SI*) 93.3) against UACC-62 cells, followed by norstictic, perlatolic, psoromic, and divaricatic acids, while norstictic and divaricatic acids were more selective against B16-F10 cells. The high SI* value obtained for protocetraric acid on UACC-62 cells makes it a potential candidate for the study of melanomas in experimental models. Chemometric analysis was performed to evaluate the general behavior of the compounds against the cell lines tested. PMID:23207680

  19. Composition of phenolic compounds in a Portuguese pear (Pyrus communis L. var. S. Bartolomeu) and changes after sun-drying.

    PubMed

    Ferreira, Dulcineia; Guyot, Sylvain; Marnet, Nathalie; Delgadillo, Ivonne; Renard, Catherine M G C; Coimbra, Manuel A

    2002-07-31

    The composition of phenolic compounds of a Portuguese pear cultivar (Pyrus communis L. var. S. Bartolomeu) was determined by HPLC after thioacidolysis. The average concentration of phenolic compounds in pear harvested at commercial maturity stage was 3.7 g per kg of fresh pulp. Procyanidins were the predominant phenolics (96%), with a mean degree of polymerization (mDP) of 13-44; hydroxycinnamic acids (2%), arbutin (0.8%), and catechins (0.7%) were also present. The most abundant monomer in the procyanidin structures was (-)-epicatechin (99%), which was found as extension and terminal units; (+)-catechin (1%) was found only as a terminal unit. Sun-drying of these pears caused a decrease of 64% (on a dry pulp basis) in the total amount of native phenolic compounds. Hydroxycinnamic acids and procyanidins showed the largest decrease; the B2 procyanidin was not found at all in the sun-dried pear. Less affected were arbutin and catechins. In the sun-dried pear, the procyanidins with high mDP became unextractable in the solvents used.

  20. Infusions of artichoke and milk thistle represent a good source of phenolic acids and flavonoids.

    PubMed

    Pereira, Carla; Barros, Lillian; Carvalho, Ana Maria; Santos-Buelga, Celestino; Ferreira, Isabel C F R

    2015-01-01

    Cynara scolymus L. (artichoke) and Silybum marianum (L.) Gaertn (milk thistle) are two herbs well-known for their efficiency in the prevention/treatment of liver injuries, among other chronic diseases. Therefore, the aim of this work was to characterize specific bioactive components, phenolic compounds, in hydromethanolic extracts but also in infusions (the most commonly used preparations) obtained from the whole plant of milk thistle and artichoke. The phenolic profiles were accessed using HPLC-DAD-MS/ESI. Infusions of both species presented higher phenolic contents than the hydromethanolic extracts. Milk thistle presented a similar phenolic composition between the two preparations, revealing only differences in the quantities obtained. Nevertheless, artichoke revealed a slightly different profile considering infusion and hydromethanolic extracts. Apigenin-7-O-glucuronide was the major flavonoid found in milk thistle, while luteolin-7-O-glucuronide was the most abundant in artichoke. Therefore, infusions of both artichoke and milk thistle represent a good source of bioactive compounds, especially phenolic acids and flavonoids. PMID:25367590

  1. Infusions of artichoke and milk thistle represent a good source of phenolic acids and flavonoids.

    PubMed

    Pereira, Carla; Barros, Lillian; Carvalho, Ana Maria; Santos-Buelga, Celestino; Ferreira, Isabel C F R

    2015-01-01

    Cynara scolymus L. (artichoke) and Silybum marianum (L.) Gaertn (milk thistle) are two herbs well-known for their efficiency in the prevention/treatment of liver injuries, among other chronic diseases. Therefore, the aim of this work was to characterize specific bioactive components, phenolic compounds, in hydromethanolic extracts but also in infusions (the most commonly used preparations) obtained from the whole plant of milk thistle and artichoke. The phenolic profiles were accessed using HPLC-DAD-MS/ESI. Infusions of both species presented higher phenolic contents than the hydromethanolic extracts. Milk thistle presented a similar phenolic composition between the two preparations, revealing only differences in the quantities obtained. Nevertheless, artichoke revealed a slightly different profile considering infusion and hydromethanolic extracts. Apigenin-7-O-glucuronide was the major flavonoid found in milk thistle, while luteolin-7-O-glucuronide was the most abundant in artichoke. Therefore, infusions of both artichoke and milk thistle represent a good source of bioactive compounds, especially phenolic acids and flavonoids.

  2. Simultaneous determination of phenolic compounds in Cynthiana grape (Vitis aestivalis) by high performance liquid chromatography-electrospray ionisation-mass spectrometry.

    PubMed

    Ramirez-Lopez, L M; McGlynn, W; Goad, C L; Mireles Dewitt, C A

    2014-04-15

    Phenolic acids, flavanols, flavonols and stilbenes (PAFFS) were isolated from whole grapes, juice, or pomace and purified using enzymatic hydrolysis. Only anthocyanin mono-glucosides and a few of the oligomers from Cynthiana grape (Vitis aestivalis) were analysed. Flavonoid-anthocyanin mono-glucosides (FA) were isolated using methanol/0.1% hydrochloric acid extraction. In addition, crude extractions of phenolic compounds from Cynthiana grape using 50% methanol, 70% methanol, 50% acetone, 0.01% pectinase, or petroleum ether were also evaluated. Reverse phase high performance liquid chromatography (RP-HPLC) with photodiode array (PDA) detector was used to identify phenolic compounds. A method was developed for simultaneous separation, identification and quantification of both PAFFS and FA. Quantification was performed by the internal standard method using a five points regression graph of the UV-visible absorption data collected at the wavelength of maximum absorbance for each analyte. From whole grape samples nine phenolic compounds were tentatively identified and quantified. The individual phenolic compounds content varied from 3 to 875 mg kg⁻¹ dry weight. For juice, twelve phenolic compounds were identified and quantified. The content varied from 0.07 to 910 mg kg⁻¹ dry weight. For pomace, a total of fifteen phenolic compounds were tentatively identified and quantified. The content varied from 2 mg kg⁻¹ to 198 mg kg⁻¹ dry matter. Results from HPLC analysis of the samples showed that gallic acid and (+)-catechin hydrate were the major phenolic compounds in both whole grapes and pomace. Cyanidin and petunidin 3-O-glucoside were the major anthocyanin glucosides in the juice.

  3. Optimization of extraction parameters on the isolation of phenolic compounds from sour cherry (Prunus cerasus L.) pomace.

    PubMed

    Yılmaz, Fatih Mehmet; Karaaslan, Mehmet; Vardin, Hasan

    2015-05-01

    There is an increasing interest to bio-components obtained from fruit & vegetable wastes. Anthocyanin is one of the components regained from fruits especially from red ones. Sour cherry is considered as industrial fruit since most of the grown fruit is processed into juice and hence considerable amount of pomace is removed from process. The influences of process parameters on the extraction of phenolic compounds from sour cherry pomace were investigated. Fifty-one percent ethanol concentration, 75 °C temperature and 12 mL/g solvent to solid ratio were selected as optimum process parameters. Time effect on the process efficiency was monitored at three different temperatures (25, 50 and 75 °C) and total phenolic and total anthocyanin contents were found to reach equilibrium concentrations between 80 and 100 min time intervals. Ethanol concentrations affected differently extraction yield of anthocyanins and non-anthocyanin phenolics. Various individual phenolic compounds present in sour cherry pomace were identified and quantified by HPLC equipped with UV/Vis PDA. Of the phenolic compounds, cyanidin-3-glucosylrutinoside, neochlorogenic acid and catechin were the most abundant ones found in the pomace. 14.23 ± 0.38 mg/g total phenolic, 0.41 ± 0.02 mg/g total anthocyanin, 0.19 ± 0.02 mg/g cyanidin-3-glucosylrutinoside, 0.22 ± 0.01 mg/g neochlorogenic acid and 0.22 ± 0.02 mg/g catechin contents (dry weight) were determined in the pomace at optimum extraction conditions. PMID:25892783

  4. Development and validation of an efficient ultrasound assisted extraction of phenolic compounds from flax (Linum usitatissimum L.) seeds.

    PubMed

    Corbin, Cyrielle; Fidel, Thibaud; Leclerc, Emilie A; Barakzoy, Esmatullah; Sagot, Nadine; Falguiéres, Annie; Renouard, Sullivan; Blondeau, Jean-Philippe; Ferroud, Clotilde; Doussot, Joël; Lainé, Eric; Hano, Christophe

    2015-09-01

    Flaxseed accumulates in its seedcoat a macromolecular complex composed of lignan (secoisolariciresinol diglucoside, SDG), flavonol (herbacetin diglucoside, HDG) and hydroxycinnamic acids (p-couramic, caffeic and ferulic acid glucosides). Their antioxidant and/or cancer chemopreventive properties support their interest in human health and therefore, the demand for their extraction. In the present study, ultrasound-assisted extraction (UAE) of flaxseed phenolic compounds was investigated. Scanning Electron Microscopy imaging and histochemical analysis revealed the deep alteration of the seedcoat ultrastructure and the release of the mucilage following ultrasound treatment. Therefore, this method was found to be very efficient for the reduction of mucilage entrapment of flaxseed phenolics. The optimal conditions for UAE phenolic compounds extraction from flaxseeds were found to be: water as solvent supplemented with 0.2N of sodium hydroxide for alkaline hydrolysis of the SDG-HMG complex, an extraction time of 60 min at a temperature of 25°C and an ultrasound frequency of 30 kHz. Under these optimized and validated conditions, highest yields of SDG, HDG and hydroxycinnamic acid glucosides were detected in comparison to other published methods. Therefore, the procedure presented herein is a valuable method for efficient extraction and quantification of the main flaxseed phenolics. Moreover, this UAE is of particular interest within the context of green chemistry in terms of reducing energy consumption and valuation of flaxseed cakes as by-products resulting from the production of flax oil.

  5. Development and validation of an efficient ultrasound assisted extraction of phenolic compounds from flax (Linum usitatissimum L.) seeds.

    PubMed

    Corbin, Cyrielle; Fidel, Thibaud; Leclerc, Emilie A; Barakzoy, Esmatullah; Sagot, Nadine; Falguiéres, Annie; Renouard, Sullivan; Blondeau, Jean-Philippe; Ferroud, Clotilde; Doussot, Joël; Lainé, Eric; Hano, Christophe

    2015-09-01

    Flaxseed accumulates in its seedcoat a macromolecular complex composed of lignan (secoisolariciresinol diglucoside, SDG), flavonol (herbacetin diglucoside, HDG) and hydroxycinnamic acids (p-couramic, caffeic and ferulic acid glucosides). Their antioxidant and/or cancer chemopreventive properties support their interest in human health and therefore, the demand for their extraction. In the present study, ultrasound-assisted extraction (UAE) of flaxseed phenolic compounds was investigated. Scanning Electron Microscopy imaging and histochemical analysis revealed the deep alteration of the seedcoat ultrastructure and the release of the mucilage following ultrasound treatment. Therefore, this method was found to be very efficient for the reduction of mucilage entrapment of flaxseed phenolics. The optimal conditions for UAE phenolic compounds extraction from flaxseeds were found to be: water as solvent supplemented with 0.2N of sodium hydroxide for alkaline hydrolysis of the SDG-HMG complex, an extraction time of 60 min at a temperature of 25°C and an ultrasound frequency of 30 kHz. Under these optimized and validated conditions, highest yields of SDG, HDG and hydroxycinnamic acid glucosides were detected in comparison to other published methods. Therefore, the procedure presented herein is a valuable method for efficient extraction and quantification of the main flaxseed phenolics. Moreover, this UAE is of particular interest within the context of green chemistry in terms of reducing energy consumption and valuation of flaxseed cakes as by-products resulting from the production of flax oil. PMID:25753491

  6. Isolation and characterization of phenolic compounds and anthocyanins from Murta (Ugni molinae Turcz.) fruits. Assessment of antioxidant and antibacterial activity.

    PubMed

    Junqueira-Gonçalves, Maria Paula; Yáñez, Lina; Morales, Carolina; Navarro, Muriel; A Contreras, Rodrigo; Zúñiga, Gustavo E

    2015-01-01

    Berry fruit consumption has become important in the promotion of human health, mainly due to their phenolic compounds, which have been associated with protection against different pathologies, as well as antimicrobial and other biological activities. Consequently, there has been a growing interest in identifying natural antioxidants and antimicrobials from these plants. This study aimed to characterize the phenolic chemical composition and anthocyanin profile of murta (Ugni molinae Turcz.) fruit, and to evaluate the antioxidant and antimicrobial activity of its extracts (ethanolic and methanolic). LC/MS of the ethanolic extracts showed the presence of three major compounds: caffeic acid 3-glu, quercetin-3-glu and quercetin, while in the methanolic acid extract they were cyanidin-3-glucoside, pelargonidin-3-arabinose and delphinidin-3-glucoside. The antioxidant activity of ethanolic extracts (DPPH· and ORAC assays) was higher than that of methanol acid extracts or purified anthocynins. Furthermore, the methanol acid extract showed an inhibitory activity against the bacteria E. coli and S. typhi similar to that of standard antibiotics. The results suggest that the antioxidant activity of the ethanolic extract is regulated by the high content of phenolic compounds and the fruit's characteristic color is due to the content of pelargonidin-3-arabinose and delphinidin-3-glucoside. The obtained results demonstrated the appreciable antioxidant and antibacterial activities, providing opportunities to explore murta extracts as biopreservatives. PMID:25838172

  7. Isolation and characterization of phenolic compounds and anthocyanins from Murta (Ugni molinae Turcz.) fruits. Assessment of antioxidant and antibacterial activity.

    PubMed

    Junqueira-Gonçalves, Maria Paula; Yáñez, Lina; Morales, Carolina; Navarro, Muriel; A Contreras, Rodrigo; Zúñiga, Gustavo E

    2015-03-31

    Berry fruit consumption has become important in the promotion of human health, mainly due to their phenolic compounds, which have been associated with protection against different pathologies, as well as antimicrobial and other biological activities. Consequently, there has been a growing interest in identifying natural antioxidants and antimicrobials from these plants. This study aimed to characterize the phenolic chemical composition and anthocyanin profile of murta (Ugni molinae Turcz.) fruit, and to evaluate the antioxidant and antimicrobial activity of its extracts (ethanolic and methanolic). LC/MS of the ethanolic extracts showed the presence of three major compounds: caffeic acid 3-glu, quercetin-3-glu and quercetin, while in the methanolic acid extract they were cyanidin-3-glucoside, pelargonidin-3-arabinose and delphinidin-3-glucoside. The antioxidant activity of ethanolic extracts (DPPH· and ORAC assays) was higher than that of methanol acid extracts or purified anthocynins. Furthermore, the methanol acid extract showed an inhibitory activity against the bacteria E. coli and S. typhi similar to that of standard antibiotics. The results suggest that the antioxidant activity of the ethanolic extract is regulated by the high content of phenolic compounds and the fruit's characteristic color is due to the content of pelargonidin-3-arabinose and delphinidin-3-glucoside. The obtained results demonstrated the appreciable antioxidant and antibacterial activities, providing opportunities to explore murta extracts as biopreservatives.

  8. Phenolic compounds: Strong inhibitors derived from lignocellulosic hydrolysate for 2,3-butanediol production by Enterobacter aerogenes.

    PubMed

    Lee, Sang Jun; Lee, Ju Hun; Yang, Xiaoguang; Kim, Sung Bong; Lee, Ja Hyun; Yoo, Hah Young; Park, Chulhwan; Kim, Seung Wook

    2015-12-01

    Lignocellulosic biomass are attractive feedstocks for 2,3-butanediol production due to their abundant supply and low price. During the hydrolysis of lignocellulosic biomass, various byproducts are formed and their effects on 2,3-butanediol production were not sufficiently studied compared to ethanol production. Therefore, the effects of compounds derived from lignocellulosic biomass (weak acids, furan derivatives and phenolics) on the cell growth, the 2,3-butanediol production and the enzymes activity involved in 2,3-butanediol production were evaluated using Enterobacter aerogenes ATCC 29007. The phenolic compounds showed the most toxic effects on cell growth, 2,3-butanediol production and enzyme activity, followed by furan derivatives and weak acids. The significant effects were not observed in the presence of acetic acid and formic acid. Also, feasibility of 2,3-butanediol production from lignocellulosic biomass was evaluated using Miscanthus as a feedstock. In the fermentation of Miscanthus hydrolysate, 11.00 g/L of 2,3-butanediol was obtained from 34.62 g/L of reducing sugar. However, 2,3-butanediol was not produced when the concentration of total phenolic compounds in the hydrolysate increased to more than 1.5 g/L. The present study provides useful information to develop strategies for biological production of 2,3-butanediol and to establish biorefinery for biochemicals from lignocellulosic biomass. PMID:26479290

  9. Phenolic compounds: Strong inhibitors derived from lignocellulosic hydrolysate for 2,3-butanediol production by Enterobacter aerogenes.

    PubMed

    Lee, Sang Jun; Lee, Ju Hun; Yang, Xiaoguang; Kim, Sung Bong; Lee, Ja Hyun; Yoo, Hah Young; Park, Chulhwan; Kim, Seung Wook

    2015-12-01

    Lignocellulosic biomass are attractive feedstocks for 2,3-butanediol production due to their abundant supply and low price. During the hydrolysis of lignocellulosic biomass, various byproducts are formed and their effects on 2,3-butanediol production were not sufficiently studied compared to ethanol production. Therefore, the effects of compounds derived from lignocellulosic biomass (weak acids, furan derivatives and phenolics) on the cell growth, the 2,3-butanediol production and the enzymes activity involved in 2,3-butanediol production were evaluated using Enterobacter aerogenes ATCC 29007. The phenolic compounds showed the most toxic effects on cell growth, 2,3-butanediol production and enzyme activity, followed by furan derivatives and weak acids. The significant effects were not observed in the presence of acetic acid and formic acid. Also, feasibility of 2,3-butanediol production from lignocellulosic biomass was evaluated using Miscanthus as a feedstock. In the fermentation of Miscanthus hydrolysate, 11.00 g/L of 2,3-butanediol was obtained from 34.62 g/L of reducing sugar. However, 2,3-butanediol was not produced when the concentration of total phenolic compounds in the hydrolysate increased to more than 1.5 g/L. The present study provides useful information to develop strategies for biological production of 2,3-butanediol and to establish biorefinery for biochemicals from lignocellulosic biomass.

  10. Effect of ultra-high pressure homogenisation processing on phenolic compounds, antioxidant capacity and anti-glucosidase of mulberry juice.

    PubMed

    Yu, Yuanshan; Xu, Yujuan; Wu, Jijun; Xiao, Gengsheng; Fu, Mangqin; Zhang, Yousheng

    2014-06-15

    In this study, the effects of ultra-high pressure homogenisation (UHPH) processing at 200 MPa for 1-3 successive passes (inlet temperatures at 4°C) were compared with pasteurisation (95°C, 1 min) processing on phenolic compounds, antioxidant capacity (ORAC value) and anti-glucosidase of mulberry juice. Compared with thermal pasteurisation processing, the more reductions in the anthocyanins, phenolic acids (gallic, protocatechuic, caffeic and p-coumaric acids, and a unknown hydroxycinnamic acid) and quercetin aglycone contents, as well as ORAC value were observed during UHPH processing of mulberry juice, whereas all reductions above during UHPH processing could be inhibited by adding ascorbic acid to mulberry juice. Besides, no significant change (p>0.05) in the α-glucosidase inhibitory activity was observed during UHPH processing of mulberry juice, but showed a 14% reduction in mulberry juice processed by thermal pasteurisation.

  11. Analysis of the phenolic compounds in longan (Dimocarpus longan lour.) peel

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Longan fruit are susceptible to chilling injury, where the injured peel exhibits discoloration due to water-soaking and enzymatic browning. This peel discoloration is dependent to a large degree on the composition of the phenolic compounds. Yet, the main classes of phenols in longan peel remain la...

  12. Antioxidant and DNA damage protection potentials of selected phenolic acids.

    PubMed

    Sevgi, Kemal; Tepe, Bektas; Sarikurkcu, Cengiz

    2015-03-01

    In this study, ten different phenolic acids (caffeic, chlorogenic, cinnamic, ferulic, gallic, p-hydroxybenzoic, protocatechuic, rosmarinic, syringic, and vanillic acids) were evaluated for their antioxidant and DNA damage protection potentials. Antioxidant activity was evaluated by using four different test systems named as β-carotene bleaching, DPPH free radical scavenging, reducing power and chelating effect. In all test systems, rosmarinic acid showed the maximum activity potential, while protocatechuic acid was determined as the weakest antioxidant in β-carotene bleaching, DPPH free radical scavenging, and chelating effect assays. Phenolic acids were also screened for their protective effects on pBR322 plasmid DNA against the mutagenic and toxic effects of UV and H2O2. Ferulic acid was found as the most active phytochemical among the others. Even at the lowest concentration value (0.002 mg/ml), ferulic acid protected all of the bands in the presence of H2O2 and UV. It is followed by caffeic, rosmarinic, and vanillic acids. On the other hand, cinnamic acid (at 0.002 mg/ml), gallic acid (at 0.002 mg/ml), p-hydroxybenzoic acid (at 0.002 and 0.004 mg/ml), and protocatechuic acid (at 0.002 and 0.004 mg/ml) could not protect plasmid DNA. PMID:25542528

  13. Influence of alternative electron acceptors on the anaerobic biodegradability of chlorinated phenols and benzoic acids

    SciTech Connect

    Haeggblom, M.M.; Rivera, M.D.; Young, L.Y.

    1993-01-01

    Nitrate, sulfate, and carbonate were used as electron acceptors to examine the anaerobic biodegradability of chlorinated aromatic compounds in estuarine and freshwater sediments. The respective denitrifying, sulfidogenic, and methanogenic enrichment cultures were established on each of the monochlorinated phenol and monochlorinated benzoic acid isomers, using sediment from the upper (freshwater) and lower (estuarine) Hudson River and the East River (estuarine) as source materials. (Copyright (c) 1993 American Society for Microbiology.)

  14. Phenolic compounds of Pinus laricio needles: a bioindicator of the effects of prescribed burning in function of season.

    PubMed

    Cannac, Magali; Pasqualini, Vanina; Barboni, Toussaint; Morandini, Frederic; Ferrat, Lila

    2009-07-15

    Fire is a dominant ecological factor in Mediterranean-type ecosystems. Forest management includes many preventive tools, in particular for fire prevention, such as mechanical treatments and prescribed burning. Prescribed burning is a commonly used method for treating fuel loads, but fuel reduction targets for reducing wildfire hazards must be balanced against fuel retention targets in order to maintain habitat and other forest functions. This approach was used on Pinus nigra ssp laricio var. Corsicana, a pine endemic to Corsica of great ecological and economic importance. Many studies of plant phenolic compounds have been carried out concerning responses to various stresses. The aim of this study was to understand i) the effects of prescribed burning 1 to 16 months later and ii) the effects of the seasonality of burning, spring or fall, on the production of phenolic compounds in Pinus laricio. After prescribed burning conducted in spring, Pinus laricio increases the synthesis of total phenolic compounds for a period of 7 months. The increase is greater after spring-burning than fall-burning. With regard to simple phenols, only dihydroferulic acid responds about 1 year after both types of prescribed burning. The causes of these increases are discussed in this paper. Total phenolic compounds could be used as a bioindicator for the short-term response of Pinus laricio needles to prescribed burning. Simple phenols may be useful for revealing the medium-term effects of prescribed burning. The results of this study include recommending forest managers to use prescribed burning in the fall rather than spring to reduce fuel loads and have less impact on the trees.

  15. Phenolic compounds from Achillea millefolium L. and their bioactivity.

    PubMed

    Vitalini, Sara; Beretta, Giangiacomo; Iriti, Marcello; Orsenigo, Simone; Basilico, Nicoletta; Dall'Acqua, Stefano; Iorizzi, Maria; Fico, Gelsomina

    2011-01-01

    Since antiquity, Achillea millefolium L. (Asteraceae) has been used in traditional medicine of several cultures, from Europe to Asia. Its richness in bioactive compounds contributes to a wide range of medicinal properties. In this study, we assessed A. millefolium methanolic extract and its isolated components for free radical scavenging activity against 2,2-diphenyl-pycrilhydrazyl, total antioxidant capacity (based on the reduction of Cu(++) to Cu(+)), and ability to inhibit lipid peroxidation. The activity against chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum was also tested. Chlorogenic acid, its derivatives and some flavonoids isolated by semipreparative HPLC and identified by NMR and spectrometric techniques were the major bioactive constituents of the methanolic extract. The latter exhibited significant antioxidant properties, as well as its flavonol glycosides and chlorogenic acids. With regard to the antiplasmodial activity, apigenin 7-glucoside was the most effective compound, followed by luteolin 7-glucoside, whereas chlorogenic acids were completely inactive. On the whole, our results confirmed A. millefolium as an important source of bioactive metabolites, justifying its pharmaceutical and ethnobotanical use.

  16. Phenolic compounds from Achillea millefolium L. and their bioactivity.

    PubMed

    Vitalini, Sara; Beretta, Giangiacomo; Iriti, Marcello; Orsenigo, Simone; Basilico, Nicoletta; Dall'Acqua, Stefano; Iorizzi, Maria; Fico, Gelsomina

    2011-01-01

    Since antiquity, Achillea millefolium L. (Asteraceae) has been used in traditional medicine of several cultures, from Europe to Asia. Its richness in bioactive compounds contributes to a wide range of medicinal properties. In this study, we assessed A. millefolium methanolic extract and its isolated components for free radical scavenging activity against 2,2-diphenyl-pycrilhydrazyl, total antioxidant capacity (based on the reduction of Cu(++) to Cu(+)), and ability to inhibit lipid peroxidation. The activity against chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum was also tested. Chlorogenic acid, its derivatives and some flavonoids isolated by semipreparative HPLC and identified by NMR and spectrometric techniques were the major bioactive constituents of the methanolic extract. The latter exhibited significant antioxidant properties, as well as its flavonol glycosides and chlorogenic acids. With regard to the antiplasmodial activity, apigenin 7-glucoside was the most effective compound, followed by luteolin 7-glucoside, whereas chlorogenic acids were completely inactive. On the whole, our results confirmed A. millefolium as an important source of bioactive metabolites, justifying its pharmaceutical and ethnobotanical use. PMID:21503279

  17. Differential Effects of Thidiazuron on Production of Anticancer Phenolic Compounds in Callus Cultures of Fagonia indica.

    PubMed

    Khan, Tariq; Abbasi, Bilal Haider; Khan, Mubarak Ali; Shinwari, Zabta Khan

    2016-04-01

    Fagonia indica, a very important anticancer plant, has been less explored for its in vitro potential. This is the first report on thidiazuron (TDZ)-mediated callogenesis and elicitation of commercially important phenolic compounds. Among the five different plant growth regulators tested, TDZ induced comparatively higher fresh biomass, 51.0 g/100 mL and 40.50 g/100 mL for stem and leaf explants, respectively, after 6 weeks of culture time. Maximum total phenolic content (202.8 μg gallic acid equivalent [GAE]/mL for stem-derived callus and 161.3 μg GAE/mL for leaf-derived callus) and total flavonoid content (191.03 μg quercetin equivalent [QE]/mL for stem-derived callus and 164.83 μg QE/mL for leaf-derived callus) were observed in the optimized callus cultures. The high-performance liquid chromatography (HPLC) data indicated higher amounts of commercially important anticancer secondary metabolites such as gallic acid (125.10 ± 5.01 μg/mL), myricetin (32.5 ± 2.05 μg/mL), caffeic acid (12.5 ± 0.52 μg/mL), catechin (9.4 ± 1.2 μg/mL), and apigenin (3.8 ± 0.45 μg/mL). Owing to the greater phenolic content, a better 2-2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity (69.45 % for stem explant and 63.68 % for leaf explant) was observed in optimized calluses. The unusually higher biomass and the enhanced amount of phenolic compounds as a result of lower amounts of TDZ highlight the importance of this multipotent hormone as elicitor in callus cultures of F. indica. PMID:26758711

  18. Hydroxylation activity of P450 BM-3 mutant F87V towards aromatic compounds and its application to the synthesis of hydroquinone derivatives from phenolic compounds.

    PubMed

    Sulistyaningdyah, Woro Triarsi; Ogawa, Jun; Li, Qing-Shan; Maeda, Chiharu; Yano, Yuki; Schmid, Rolf D; Shimizu, Sakayu

    2005-06-01

    Cytochrome P450 BM-3 from Bacillus megaterium is a fatty acid hydroxylase exhibiting selectivity for long-chain substrates (12-20 carbons). Replacement of Phe87 in P450 BM-3 by Val (F87V) greatly increased its activity towards a variety of aromatic and phenolic compounds. The apparent initial reaction rates of F87V as to benzothiophene, indan, 2,6-dichlorophenol, and 2-(benzyloxy)phenol were 227, 204, 129, and 385 nmol min(-1) nmol(-1) P450, which are 220-, 66-, 99-, and 963-fold those of the wild type, respectively. These results indicate that Phe87 plays a critical role in the control of the substrate specificity of P450 BM-3. Furthermore, F87V catalyzed regioselective hydroxylation at the para position of various phenolic compounds. In particular, F87V showed high activity as to the hydroxylation of 2-(benzyloxy)phenol to 2-(benzyloxy)hydroquinone. With F87V as the catalyst, 0.71 mg ml(-1) 2-(benzyloxy)hydroquinone was produced from 1.0 mg ml(-1) 2-(benzyloxy)phenol in 4 h, with a molar yield of 66%.

  19. Kinetics of the incorporation of the main phenolic compounds into the lignan macromolecule during flaxseed development.

    PubMed

    Ramsay, Aina; Fliniaux, Ophélie; Quéro, Anthony; Molinié, Roland; Demailly, Hervé; Hano, Christophe; Paetz, Christian; Roscher, Albrecht; Grand, Eric; Kovensky, José; Schneider, Bernd; Mesnard, François

    2017-02-15

    The main flax lignan, secoisolariciresinol diglucoside, is stored in a macromolecule containing other ester-bound phenolic compounds. In this study, NMR and HPLC-UV analyses were performed on flaxseeds harvested at different developmental stages to identify and quantify the main phenolic compounds produced during seed development. Extraction was carried out with or without alkaline hydrolysis to determine if these molecules accumulate in the lignan macromolecule and/or in a free form. Monolignol glucosides accumulate in a free form up to 9.85mg/g dry matter at the early developmental stages. Hydroxycinnamic acid glucosides and flavonoid accumulate (up to 3.18 and 4.07mg/g dry matter, respectively) in the later developmental stages and are ester-bound in the lignan macromolecule. Secosiolariciresinol diglucoside accumulates (up to 28.65mg/g dry matter) in the later developmental stages in both forms, mainly ester-bound in the lignan macromolecule and slightly in a free form. PMID:27664601

  20. Antioxidant and cytotoxic activities of naturally occurring phenolic and related compounds: a comparative study.

    PubMed

    Rao, Yerra Koteswara; Geethangili, Madamanchi; Fang, Shih-Hua; Tzeng, Yew-Min

    2007-09-01

    The antioxidant (DPPH radical and superoxide anion scavenging activities), and cytotoxic (in tumor, Jurkat, PC-3, Colon 205, HepG2, and normal PBMCs cells) activities of 16 plant phenolic or related compounds were evaluated in vitro. Different categories compounds corresponding to 10 flavonoids, three lignans, two phenolic acids, and a catechin showed significant mean differences in antioxidant and cytotoxic activities. Particularly, the flavonols, quercetin (3) and tiliroside (11) possess significant antioxidant activity, as well as cytotoxic activity against Jurkat; and Jurkat and HepG2 cells, respectively. In contrast, the flavanone, 5,7-dimethoxy-3',4'-methylenedioxyflavanone (7), and homoisoflavonoid, isobonducellin (10) shown to have no significant antioxidant activity, but exhibited potent cytotoxic activity in Jurkat and HepG2 cells, while moderate growth inhibition against Colon205 cells. Interestingly, none of these derivatives shown to have toxicity toward normal peripheral blood mononuclear cells, over the concentration range tested (5-200 microM). Cytotoxic activities of some natural flavonoids identified in the medicinal plants were evaluated for the first time.

  1. The impact of milling and thermal processing on phenolic compounds in cereal grains.

    PubMed

    Ragaee, Sanaa; Seetharaman, Koushik; Abdel-Aal, El-Sayed M

    2014-01-01

    Consumption of wholegrain foods has been recommended for healthy diets. The beneficial health properties of wholegrain products have been associated with the presence of higher amounts of dietary fiber and antioxidants and lower calories as compared to their respective refined ones. Phenolic compounds are mainly attributed to antioxidant properties of wholegrain foods. This review article provides a single comprehensive source that describes effects of milling and thermal processing on phenolic compounds and antioxidant properties in cereals. In general, milling and pearling processes affect the distribution of phenolic, compounds and thus antioxidant properties vary among the milling fractions. Thermal processes such as baking and extrusion could cause negative or positive effects on phenolic compounds and antioxidant properties of the end product subject to grain type and processing conditions. Thus factors that enhance health benefits of wholegrain cereal products have been discussed.

  2. Phenolic compounds and antioxidant activity of red wine made from grapes treated with different fungicides.

    PubMed

    Mulero, J; Martínez, G; Oliva, J; Cermeño, S; Cayuela, J M; Zafrilla, P; Martínez-Cachá, A; Barba, A

    2015-08-01

    The effect of treating grapes with six fungicides, applied under critical agricultural practices (CAP) on levels of phenolic compounds and antioxidant activity of red wines of Monastrell variety was studied. Vinifications were performed through addition of active dry yeast (ADY). Measurement of phenolic compounds was made with HPLC-DAD. Determination of antioxidant activity was through reaction of the wine sample with the DPPH radical. The wine prepared from grapes treated with quinoxyfen shows a greater increase of phenolic compounds than the control wine. In contrast, the wine obtained from grapes treated with trifloxystrobin showed lower total concentration of phenolic compounds, including stilbenes, whilst treatments with kresoxim-methyl, fluquinconazole, and famoxadone slightly reduced their content. Hence, the use of these last four fungicides could cause a decrease in possible health benefits to consumers. Antioxidant activity hardly varied in the assays with quinoxyfen, fluquinconazole and famoxadone, and decreased in the other wines.

  3. Toxicological aspects of the use of phenolic compounds in disease prevention

    PubMed Central

    Kyselova, Zuzana

    2011-01-01

    The consumption of a diet low in fat and enhanced by fruits and vegetables, especially rich in phenolic compounds, may reduce risks of many civilization diseases. The use of traditional medicines, mainly derived from plant sources, has become an attractive segment in the management of many lifestyle diseases. Concerning the application of dietary supplements (based on phenolic compounds) in common practice, the ongoing debate over possible adverse effects of certain nutrients and dosage levels is of great importance. Since dietary supplements are not classified as drugs, their potential toxicities and interactions have not been thoroughly evaluated. First, this review will introduce phenolic compounds as natural substances beneficial for human health. Second, the potential dual mode of action of flavonoids will be outlined. Third, potential deleterious impacts of phenolic compounds utilization will be discussed: pro-oxidant and estrogenic activities, cancerogenic potential, cytotoxic effects, apoptosis induction and flavonoid-drug interaction. Finally, future trends within the research field will be indicated. PMID:22319251

  4. Enzymatic electrochemical detection coupled to multivariate calibration for the determination of phenolic compounds in environmental samples.

    PubMed

    Hernandez, Silvia R; Kergaravat, Silvina V; Pividori, Maria Isabel

    2013-03-15

    An approach based on the electrochemical detection of the horseradish peroxidase enzymatic reaction by means of square wave voltammetry was developed for the determination of phenolic compounds in environmental samples. First, a systematic optimization procedure of three factors involved in the enzymatic reaction was carried out using response surface methodology through a central composite design. Second, the enzymatic electrochemical detection coupled with a multivariate calibration method based in the partial least-squares technique was optimized for the determination of a mixture of five phenolic compounds, i.e. phenol, p-aminophenol, p-chlorophenol, hydroquinone and pyrocatechol. The calibration and validation sets were built and assessed. In the calibration model, the LODs for phenolic compounds oscillated from 0.6 to 1.4 × 10(-6) mol L(-1). Recoveries for prediction samples were higher than 85%. These compounds were analyzed simultaneously in spiked samples and in water samples collected close to tanneries and landfills. PMID:23598144

  5. Enzymatic electrochemical detection coupled to multivariate calibration for the determination of phenolic compounds in environmental samples.

    PubMed

    Hernandez, Silvia R; Kergaravat, Silvina V; Pividori, Maria Isabel

    2013-03-15

    An approach based on the electrochemical detection of the horseradish peroxidase enzymatic reaction by means of square wave voltammetry was developed for the determination of phenolic compounds in environmental samples. First, a systematic optimization procedure of three factors involved in the enzymatic reaction was carried out using response surface methodology through a central composite design. Second, the enzymatic electrochemical detection coupled with a multivariate calibration method based in the partial least-squares technique was optimized for the determination of a mixture of five phenolic compounds, i.e. phenol, p-aminophenol, p-chlorophenol, hydroquinone and pyrocatechol. The calibration and validation sets were built and assessed. In the calibration model, the LODs for phenolic compounds oscillated from 0.6 to 1.4 × 10(-6) mol L(-1). Recoveries for prediction samples were higher than 85%. These compounds were analyzed simultaneously in spiked samples and in water samples collected close to tanneries and landfills.

  6. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. 721.3800 Section 721.3800... Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. (a... generically as formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol,...

  7. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. 721.3800 Section 721.3800... Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. (a... generically as formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol,...

  8. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. 721.3800 Section 721.3800... Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. (a... generically as formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol,...

  9. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. 721.3800 Section 721.3800... Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. (a... generically as formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol,...

  10. 40 CFR 721.3800 - Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. 721.3800 Section 721.3800... Formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol, ethylene oxide adduct. (a... generically as formaldehyde, condensated polyoxyethylene fatty acid, ester with styrenated phenol,...

  11. Analysis of Phenolic Acids of Jerusalem Artichoke (Helianthus tuberosus L.) Responding to Salt-Stress by Liquid Chromatography/Tandem Mass Spectrometry

    PubMed Central

    Chen, Fujia; Long, Xiaohua; Liu, Zhaopu; Shao, Hongbo; Liu, Ling

    2014-01-01

    Plant phenolics can have applications in pharmaceutical and other industries. To identify and quantify the phenolic compounds in Helianthus tuberosus leaves, qualitative analysis was performed by a reversed phase high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS) and quantitative analysis by HPLC. Ten chlorogenic acids (CGAs) were identified (3-o-caffeoylquinic acid, two isomers of caffeoylquinic acid, caffeic acid, p-coumaroyl-quinic acid, feruloylquinic acid, 3,4-dicaffeoyquinic acid, 3,5-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid) by comparing their retention times, UV-Vis absorption spectra, and MS/MS spectra with standards. In addition, four other phenolic compounds, including caffeoyl glucopyranose, isorhamnetin glucoside, kaempferol glucuronide, and kaempferol-3-o-glucoside, were tentatively identified in Helianthus tuberosus leaves for the first time. The 3-o-caffeoylquinic acid (7.752 mg/g DW), 4,5-dicaffeoylquinic acid (5.633 mg/g DW), and 3,5-dicaffeoylquinic acid (4.900 mg/g DW) were the major phenolic compounds in leaves of Helianthus tuberosus cultivar NanYu in maturity. The variations in phenolic concentrations and proportions in Helianthus tuberosus leaves were influenced by genotype and plant growth stage. Cultivar NanYu had the highest concentration of phenolic compounds, in particular 3-o-caffeoylquinic acid and 4,5-dicaffeoylquinic acid compared with the other genotypes (wild accession and QingYu). Considering various growth stages, the concentration of total phenolics in cultivar NanYu was higher at flowering stage (5.270 mg/g DW) than at budding and tuber swelling stages. Cultivar NanYu of Helianthus tuberosus is a potential source of natural phenolics that may play an important role in the development of pharmaceuticals. PMID:25302328

  12. Analysis of phenolic acids of Jerusalem artichoke (Helianthus tuberosus L.) responding to salt-stress by liquid chromatography/tandem mass spectrometry.

    PubMed

    Chen, Fujia; Long, Xiaohua; Liu, Zhaopu; Shao, Hongbo; Liu, Ling

    2014-01-01

    Plant phenolics can have applications in pharmaceutical and other industries. To identify and quantify the phenolic compounds in Helianthus tuberosus leaves, qualitative analysis was performed by a reversed phase high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS) and quantitative analysis by HPLC. Ten chlorogenic acids (CGAs) were identified (3-o-caffeoylquinic acid, two isomers of caffeoylquinic acid, caffeic acid, p-coumaroyl-quinic acid, feruloylquinic acid, 3,4-dicaffeoyquinic acid, 3,5-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid) by comparing their retention times, UV-Vis absorption spectra, and MS/MS spectra with standards. In addition, four other phenolic compounds, including caffeoyl glucopyranose, isorhamnetin glucoside, kaempferol glucuronide, and kaempferol-3-o-glucoside, were tentatively identified in Helianthus tuberosus leaves for the first time. The 3-o-caffeoylquinic acid (7.752 mg/g DW), 4,5-dicaffeoylquinic acid (5.633 mg/g DW), and 3,5-dicaffeoylquinic acid (4.900 mg/g DW) were the major phenolic compounds in leaves of Helianthus tuberosus cultivar NanYu in maturity. The variations in phenolic concentrations and proportions in Helianthus tuberosus leaves were influenced by genotype and plant growth stage. Cultivar NanYu had the highest concentration of phenolic compounds, in particular 3-o-caffeoylquinic acid and 4,5-dicaffeoylquinic acid compared with the other genotypes (wild accession and QingYu). Considering various growth stages, the concentration of total phenolics in cultivar NanYu was higher at flowering stage (5.270 mg/g DW) than at budding and tuber swelling stages. Cultivar NanYu of Helianthus tuberosus is a potential source of natural phenolics that may play an important role in the development of pharmaceuticals.

  13. Analysis of phenolic acids of Jerusalem artichoke (Helianthus tuberosus L.) responding to salt-stress by liquid chromatography/tandem mass spectrometry.

    PubMed

    Chen, Fujia; Long, Xiaohua; Liu, Zhaopu; Shao, Hongbo; Liu, Ling

    2014-01-01

    Plant phenolics can have applications in pharmaceutical and other industries. To identify and quantify the phenolic compounds in Helianthus tuberosus leaves, qualitative analysis was performed by a reversed phase high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS) and quantitative analysis by HPLC. Ten chlorogenic acids (CGAs) were identified (3-o-caffeoylquinic acid, two isomers of caffeoylquinic acid, caffeic acid, p-coumaroyl-quinic acid, feruloylquinic acid, 3,4-dicaffeoyquinic acid, 3,5-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid) by comparing their retention times, UV-Vis absorption spectra, and MS/MS spectra with standards. In addition, four other phenolic compounds, including caffeoyl glucopyranose, isorhamnetin glucoside, kaempferol glucuronide, and kaempferol-3-o-glucoside, were tentatively identified in Helianthus tuberosus leaves for the first time. The 3-o-caffeoylquinic acid (7.752 mg/g DW), 4,5-dicaffeoylquinic acid (5.633 mg/g DW), and 3,5-dicaffeoylquinic acid (4.900 mg/g DW) were the major phenolic compounds in leaves of Helianthus tuberosus cultivar NanYu in maturity. The variations in phenolic concentrations and proportions in Helianthus tuberosus leaves were influenced by genotype and plant growth stage. Cultivar NanYu had the highest concentration of phenolic compounds, in particular 3-o-caffeoylquinic acid and 4,5-dicaffeoylquinic acid compared with the other genotypes (wild accession and QingYu). Considering various growth stages, the concentration of total phenolics in cultivar NanYu was higher at flowering stage (5.270 mg/g DW) than at budding and tuber swelling stages. Cultivar NanYu of Helianthus tuberosus is a potential source of natural phenolics that may play an important role in the development of pharmaceuticals. PMID:25302328

  14. Inhibitory effect of rice bran extracts and its phenolic compounds on polyphenol oxidase activity and browning in potato and apple puree.

    PubMed

    Sukhonthara, Sukhontha; Kaewka, Kunwadee; Theerakulkait, Chockchai

    2016-01-01

    Full-fatted and commercially defatted rice bran extracts (RBE and CDRBE) were evaluated for their ability to inhibit enzymatic browning in potato and apple. RBE showed more effective inhibition of polyphenol oxidase (PPO) activity and browning in potato and apple as compared to CDRBE. Five phenolic compounds in RBE and CDRBE (protocatechuic acid, vanillic acid, p-coumaric acid, ferulic acid and sinapic acid) were identified by HPLC. They were then evaluated for their important role in the inhibition using a model system which found that ferulic acid in RBE and p-coumaric acid in CDRBE were active in enzymatic browning inhibition of potato and apple. p-Coumaric acid exhibited the highest inhibitory effect on potato and apple PPO (p ⩽ 0.05). Almost all phenolic compounds showed higher inhibitory effect on potato and apple PPO than 100 ppm citric acid.

  15. Inhibitory effect of rice bran extracts and its phenolic compounds on polyphenol oxidase activity and browning in potato and apple puree.

    PubMed

    Sukhonthara, Sukhontha; Kaewka, Kunwadee; Theerakulkait, Chockchai

    2016-01-01

    Full-fatted and commercially defatted rice bran extracts (RBE and CDRBE) were evaluated for their ability to inhibit enzymatic browning in potato and apple. RBE showed more effective inhibition of polyphenol oxidase (PPO) activity and browning in potato and apple as compared to CDRBE. Five phenolic compounds in RBE and CDRBE (protocatechuic acid, vanillic acid, p-coumaric acid, ferulic acid and sinapic acid) were identified by HPLC. They were then evaluated for their important role in the inhibition using a model system which found that ferulic acid in RBE and p-coumaric acid in CDRBE were active in enzymatic browning inhibition of potato and apple. p-Coumaric acid exhibited the highest inhibitory effect on potato and apple PPO (p ⩽ 0.05). Almost all phenolic compounds showed higher inhibitory effect on potato and apple PPO than 100 ppm citric acid. PMID:26213057

  16. Effects of Glyphosate on Metabolism of Phenolic Compounds

    PubMed Central

    Duke, Stephen O.; Hoagland, Robert E.; Elmore, C. Dennis

    1980-01-01

    The phenylalanine ammonia-lyase (PAL) inhibitor l-α-aminooxy-β-phenylpropionic acid (AOPP) was root-fed to light-exposed soybean seedlings alone or with glyphosate [N-(phosphonomethyl)glycine] to test further the hypothesis that PAL activity is involved in the mode of action of glyphosate. Extractable PAL activity was increased by 0.01 and 0.1 millimolar AOPP. AOPP reduced total soluble hydroxyphenolic compound levels and increased phenylalanine and tyrosine levels, indicating that in vivo PAL activity was inhibited by AOPP. The increase in extractable PAL caused by AOPP may be a result of decreased feedback inhibition of PAL synthesis by cinnamic acid and/or its derivatives. AOPP alone had no effect on growth (fresh weight and elongation) at either concentration, but at 0.1 millimolar it slightly alleviated growth (fresh weight) inhibition caused by 0.5 millimolar glyphosate after 4 days. Reduction of the free pool of phenylalanine by glyphosate was reversed by AOPP. These results indicate that glyphosate exerts some of its effects through reduction of aromatic amino acid pools through increases in PAL activity and that not all growth effects of glyphosate are due to reductions of aromatic amino acids. PMID:16661135

  17. Adsorption of phenolic compound by aged-refuse.

    PubMed

    Xiaoli, Chai; Youcai, Zhao

    2006-09-01

    The adsorption of phenol, 2-chlorophenol, 4-chlorophenol and 2,4-dichlorophenol by aged-refuse has been studied. Adsorption isotherms have been determined for phenol, 2-chlorophenol, 4-chlorophenol and 2,4-dichlorophenol and the data fits well to the Freundlich equation. The chlorinated phenols are absorbed more strongly than the phenol and the adsorption capacity has an oblivious relationship with the numbers and the position of chlorine subsistent. The experiment data suggests that both the partition function and the chemical adsorption involve in the adsorption process. Pseudo-first-order and pseudo-second-order model were applied to investigate the kinetics of the adsorption and the results show that it fit the pseudo-second-order model. More than one step involves in the adsorption process and the overall rate of the adsorption process appears to be controlled by the chemical reaction. The thermodynamic analysis indicates that the adsorption is spontaneous and endothermic.

  18. Antiproliferative activity of New Zealand propolis and phenolic compounds vs human colorectal adenocarcinoma cells.

    PubMed

    Catchpole, Owen; Mitchell, Kevin; Bloor, Stephen; Davis, Paul; Suddes, Amanda

    2015-10-01

    New Zealand propolis is a "European" type propolis obtained by honey bees mainly from exudates of poplar. European type propolis is known to have anti-inflammatory and anti-cancer properties and this activity has been attributed to some of the main constituents such as chrysin and CAPE (caffeic acid phenethyl ester). As part of our studies on how New Zealand propolis might benefit gastro-intestinal health, we carried out in vitro bioactivity-guided fractionation of "Bio30™" propolis using both anti-inflammatory (TNF-α, COX-1, COX-2) and anti-colon cancer (DLD-1 colon cancer cell viability) assays; and determined the phenolic compounds responsible for the activity. The New Zealand wax-free Bio30™ propolis tincture solids had very high levels of the dihydroflavonoids pinocembrin and pinobanksin-3-O-acetate, and high levels of the dimethylallyl, benzyl and 3-methyl-3-butenyl caffeates relative to CAPE. The DLD-1 assays identified strong anti-proliferative activity associated with these components as well as chrysin, galangin and CAPE and a number of lesser known or lower concentration compounds including benzyl ferulate, benzyl isoferulate, pinostrobin, 5-phenylpenta-2,4-dienoic acid and tectochrysin. The phenolic compounds pinocembrin, pinobanksin-3-O-acetate, tectochrysin, dimethylallyl caffeate, 3-methyl-3-butenyl caffeate, benzyl ferulate and benzyl isoferulate also showed good broad spectrum activity in anti-proliferative assays against three other gastro-intestinal cancer cell lines; HCT-116 colon carcinoma, KYSE-30 oesophageal squamous cancer, and NCI-N87 gastric carcinoma. Activity is also observed in anti-inflammatory assays although it appears to be limited to one of the first cytokines in the inflammatory cascade, TNF-α. PMID:26347954

  19. Antiproliferative activity of New Zealand propolis and phenolic compounds vs human colorectal adenocarcinoma cells.

    PubMed

    Catchpole, Owen; Mitchell, Kevin; Bloor, Stephen; Davis, Paul; Suddes, Amanda

    2015-10-01

    New Zealand propolis is a "European" type propolis obtained by honey bees mainly from exudates of poplar. European type propolis is known to have anti-inflammatory and anti-cancer properties and this activity has been attributed to some of the main constituents such as chrysin and CAPE (caffeic acid phenethyl ester). As part of our studies on how New Zealand propolis might benefit gastro-intestinal health, we carried out in vitro bioactivity-guided fractionation of "Bio30™" propolis using both anti-inflammatory (TNF-α, COX-1, COX-2) and anti-colon cancer (DLD-1 colon cancer cell viability) assays; and determined the phenolic compounds responsible for the activity. The New Zealand wax-free Bio30™ propolis tincture solids had very high levels of the dihydroflavonoids pinocembrin and pinobanksin-3-O-acetate, and high levels of the dimethylallyl, benzyl and 3-methyl-3-butenyl caffeates relative to CAPE. The DLD-1 assays identified strong anti-proliferative activity associated with these components as well as chrysin, galangin and CAPE and a number of lesser known or lower concentration compounds including benzyl ferulate, benzyl isoferulate, pinostrobin, 5-phenylpenta-2,4-dienoic acid and tectochrysin. The phenolic compounds pinocembrin, pinobanksin-3-O-acetate, tectochrysin, dimethylallyl caffeate, 3-methyl-3-butenyl caffeate, benzyl ferulate and benzyl isoferulate also showed good broad spectrum activity in anti-proliferative assays against three other gastro-intestinal cancer cell lines; HCT-116 colon carcinoma, KYSE-30 oesophageal squamous cancer, and NCI-N87 gastric carcinoma. Activity is also observed in anti-inflammatory assays although it appears to be limited to one of the first cytokines in the inflammatory cascade, TNF-α.

  20. Potentiation of the bioavailability of blueberry phenolic compounds by co-ingested grape phenolic compounds in mice, revealed by targeted metabolomic profiling in plasma and feces.

    PubMed

    Dudonné, Stéphanie; Dal-Pan, Alexandre; Dubé, Pascal; Varin, Thibault V; Calon, Frédéric; Desjardins, Yves

    2016-08-10

    The low bioavailability of dietary phenolic compounds, resulting from poor absorption and high rates of metabolism and excretion, is a concern as it can limit their potential beneficial effects on health. Targeted metabolomic profiling in plasma and feces of mice supplemented for 15 days with a blueberry extract, a grape extract or their combination revealed significantly increased plasma concentrations (3-5 fold) of blueberry phenolic metabolites in the presence of a co-ingested grape extract, associated with an equivalent decrease in their appearance in feces. Additionally, the repeated daily administration of the blueberry-grape combination significantly increased plasma phenolic concentrations (2-3-fold) compared to animals receiving only a single acute dose, with no such increase being observed with individual extracts. These findings highlight a positive interaction between blueberry and grape constituents, in which the grape extract enhanced the absorption of blueberry phenolic compounds. This study provides for the first time in vivo evidence of such an interaction occurring between co-ingested phenolic compounds from fruit extracts leading to their improved bioavailability. PMID:27443888

  1. Influence of phenolic compounds on the sensorial perception and volatility of red wine esters in model solution: an insight at the molecular level.

    PubMed

    Lorrain, Bénédicte; Tempere, Sophie; Iturmendi, Nerea; Moine, Virginie; de Revel, Gilles; Teissedre, Pierre-Louis

    2013-09-01

    Impact of (+)-catechin and gallic acid on sensory perception and volatility of isoamyl acetate, ethyl isobutyrate, ethyl butyrate and ethyl octanoate was investigated in model solutions, by means of triangle tests, detection threshold determination and HS-GC-MS analyses. Catechin significantly altered the sensory perception of most esters (ethyl isobutyrate, ethyl butyrate and ethyl octanoate) while gallic acid displayed no impact. Ethyl butyrate and ethyl octanoate odour thresholds doubled or tripled in the presence of catechin, underlining a retention impact of phenolic compounds in liquid matrix. The headspace analyses displayed a decrease only in ethyl octanoate volatility in presence of catechin, whereas no significant difference in other esters concentrations was observed. This study indicated that phenolic compounds have a variable impact on aroma compounds' volatility and their sensory perception. The polarity of phenolic and volatile compounds as well as their spatial conformation also appeared to influence the interaction strength. PMID:23578617

  2. High-temperature operating biosensor for the determination of phenol and related compounds

    SciTech Connect

    Rella, R.; Ferrara, D.; Barison, G.; Doretti, L.

    1996-08-01

    Living phenol-oxidizing Bacillus stearothermophilus cells were immobilized in a hydroxyethyl methacrylate membrane. A thermostable biosensor was developed by coupling the bacterially activated membrane with a dissolved oxygen electrode and was utilized for the amperometric determination of phenols. Linear relationships were obtained for phenol, catechol and some related compounds. The steady-state response was very fast (max. 2 min), faster than other analogous biosensors. Its response was stable, reproducible for months and quite specific. The biosensor may be utilized over a wide temperature (35-55{degrees}C), pH (4.5-8.0) range and in matrices containing compounds toxic for most microorganisms and enzymes used. The best performance was observed at 55{degrees}C and pH 7.2. Owing to its sensitivity, stability and operational simplicity, the phenol biosensor can potentially be applied for the on-line monitoring of phenols in industrial waste effluents. 29 refs., 7 figs., 1 tab.

  3. Performance of structured lipids incorporating selected phenolic and ascorbic acids.

    PubMed

    Gruczynska, Eliza; Przybylski, Roman; Aladedunye, Felix

    2015-04-15

    Conditions applied during frying require antioxidant which is stable at these conditions and provides protection for frying oil and fried food. Novel structured lipids containing nutraceuticals and antioxidants were formed by enzymatic transesterification, exploring canola oil and naturally occurring antioxidants such as ascorbic and selected phenolic acids as substrates. Lipozyme RM IM lipase from Rhizomucor miehei was used as biocatalyst. Frying performance and oxidative stability of the final transesterification products were evaluated. The novel lipids showed significantly improved frying performance compared to canola oil. Oxidative stability assessment of the structured lipids showed significant improvement in resistance to oxidative deterioration compared to original canola oil. Interestingly, the presence of ascorbic acid in an acylglycerol structure protected α-tocopherol against thermal degradation, which was not observed for the phenolic acids. Developed structured lipids containing nutraceuticals and antioxidants may directly affect nutritional properties of lipids also offering nutraceutical ingredients for food formulation.

  4. Simultaneous determination of 14 phenolic compounds in grape canes by HPLC-DAD-UV using wavelength switching detection.

    PubMed

    Zhang, Ang; Wan, Li; Wu, Cuiyun; Fang, Yulin; Han, Guomin; Li, Hua; Zhang, Zhenwen; Wang, Hua

    2013-11-18

    The paper described a novel chromatographic method for the simultaneous determination of phenolic compounds such as gallic, protocatechuic, vanillic, caffeic, syringic, p-coumaric and salicylic acid, (+)-catechin, (‒)-epicatechin, rutin, morin, quercetin, coumarin and trans-resveratrol at their maximum absorbance wavelengths (MAW) employing reverse-phase high performance liquid chromatography combined with DAD and UV detection via detection wavelength switching. The method was based on MAW acquisition by DAD and quantification by UV. The separation process was performed on a Shim-Pack VP-ODS C18 column (250 mm × 4.6 mm, 5 μm) held at 30 °C, utilizing 3.0% acetic acid and acetonitrile as mobile phase at a flow rate of 0.8 mL/min in the gradient elution mode. The method was fully validated in terms of linearity (r2 > 0.9990, 10‒350 mg/L), precision (both intra-day and inter-day RSD < 4.22%), accuracy (97.31%‒104.66%), specificity, robustness (0.59% < RSD < 2.86%), limit of detection and quantification. The switching method significantly improved the sensitivities of most phenolics studied in comparison with the standard constant wavelength detection (280 nm). The proposed method has been successfully applied to the determination of 14 phenolic compounds in 89 varieties of one-year-old Chinese grape one-year-canes. Grape canes contain many phenolics, especially trans-resveratrol, (‒)-epicatechin, and (+)-catechin.

  5. Quantitative analysis of flavonoids and phenolic acids in Arnica montana L. by micellar electrokinetic capillary chromatography.

    PubMed

    Ganzera, Markus; Egger, Christoph; Zidorn, Christian; Stuppner, Hermann

    2008-05-01

    Arnica montana preparations have been used in Europe for centuries to treat skin disorders. Among the biologically active ingredients in the flower heads of the plant are sequiterpenes, flavonoids and phenolic acids. For the simultaneous determination of compounds belonging to the latter two groups a micellar electrokinetic capillary chromatography (MEKC) method was developed and validated. By using an electrolyte solution containing 50 mM borax, 25 mM sodium dodecyl sulfate and 30% of acetonitrile the separation of seven flavonoids and four caffeic acid derivatives was feasible in less than 20 min. The optimized system was validated for repeatability (sigma(rel) < or = 4.4%), precision (inter-day sigma(rel) < or = 8.13%, intra-day sigma(rel) < or = 4.32%), accuracy (recovery rates from 96.8 to 102.4%), sensitivity (limit of detection (LOD) < or = 4.5 microg mL(-1)) and linearity (R(2) > or = 0.9996), and then successfully applied to assay several plant samples. In all of them the most dominant flavonoid was found to be quercetin 3-O-glucuronic acid, whereas 3,5-dicaffeoylquinic acid was the major phenolic acid; the total content of flavonoids and phenolic acids varied in the samples from 0.60 to 1.70%, and 1.03 to 2.24%, respectively.

  6. Identification of phenolic compounds in plum fruits (Prunus salicina L. and Prunus domestica L.) by high-performance liquid chromatography/tandem mass spectrometry and characterization of varieties by quantitative phenolic fingerprints.

    PubMed

    Jaiswal, Rakesh; Karaköse, Hande; Rühmann, Susanne; Goldner, Katharina; Neumüller, Michael; Treutter, Dieter; Kuhnert, Nikolai

    2013-12-11

    Plums (Prunus domestica L. and Prunus salicina L.) are edible fruits mostly consumed in America, China, and Europe. We have used LC-MS(n) to detect and characterize the phenolic compounds in plum varieties. Forty-one phenolics were detected comprising caffeoylquinic acids, feruloylquinic acid, p-coumaroylquinic acids, methyl caffeoylquinates, methyl p-coumaroylquinate, caffeoylshikimic acids, catechin, epicatechin, rutin, esculin, quercetin, quercetin-3-O-hexosides, dimeric proanthocyanidins, trimeric proanthocyanidins, caffeoyl-glucoside, feruloyl-glucoside, p-coumaroyl-glucoside, vanillic acid-glucosides, 3,4-dihydroxybenzoyl-glucoside, quercetin-3-O-pentosides, quercetin-3-O-rhamnoside, quercetin-pentoside-rhamnosides, and 3-p-methoxycinnamoylquinic acid. This is the first time when 3-p-methoxycinnamoylquinic acid is reported in nature. Chlorogenic acids and proanthocyanidins were the major phenolics present in plums. Furthermore, HPLC with DAD and chemical reaction detection was used to generate quantitative phenolic fingerprints from the fruit flesh of 33 plum varieties. The predominant compound was 3-caffeoylquinic acid in nearly all varieties studied; generally, however, the qualitative and quantitative profiles showed high diversity even among closely related progenies.

  7. Physical features, phenolic compounds, betalains and total antioxidant capacity of coloured quinoa seeds (Chenopodium quinoa Willd.) from Peruvian Altiplano.

    PubMed

    Abderrahim, Fatima; Huanatico, Elizabeth; Segura, Roger; Arribas, Silvia; Gonzalez, M Carmen; Condezo-Hoyos, Luis

    2015-09-15

    Physical features, bioactive compounds and total antioxidant capacity (TAC) of coloured quinoa varieties (Chenopodium quinoa Willd.) from Peruvian Altiplano were studied. Quinoa seeds did not show a pure red colour, but a mixture which corresponded to different fractal colour values (51.0-71.8), and they varied from small to large size. Regarding bioactive compounds, total phenolic (1.23-3.24mg gallic acid equivalents/g) and flavonol contents (0.47-2.55mg quercetin equivalents/g) were highly correlated (r=0.910). Betalains content (0.15-6.10mg/100g) was correlated with L colour parameter (r=-0.569), total phenolics (r=0.703) and flavonols content (r=0.718). Ratio of betaxanthins to betacyanins (0.0-1.41) was negatively correlated with L value (r=-0.744). Whereas, high TAC values (119.8-335.9mmol Trolox equivalents/kg) were negatively correlated with L value (r=-0.779), but positively with betalains (r=0.730), as well as with free (r=0.639), bound (r=0.558) and total phenolic compounds (r=0.676). Unexploited coloured quinoa seeds are proposed as a valuable natural source of phenolics and betalains with high antioxidant capacity.

  8. Physical features, phenolic compounds, betalains and total antioxidant capacity of coloured quinoa seeds (Chenopodium quinoa Willd.) from Peruvian Altiplano.

    PubMed

    Abderrahim, Fatima; Huanatico, Elizabeth; Segura, Roger; Arribas, Silvia; Gonzalez, M Carmen; Condezo-Hoyos, Luis

    2015-09-15

    Physical features, bioactive compounds and total antioxidant capacity (TAC) of coloured quinoa varieties (Chenopodium quinoa Willd.) from Peruvian Altiplano were studied. Quinoa seeds did not show a pure red colour, but a mixture which corresponded to different fractal colour values (51.0-71.8), and they varied from small to large size. Regarding bioactive compounds, total phenolic (1.23-3.24mg gallic acid equivalents/g) and flavonol contents (0.47-2.55mg quercetin equivalents/g) were highly correlated (r=0.910). Betalains content (0.15-6.10mg/100g) was correlated with L colour parameter (r=-0.569), total phenolics (r=0.703) and flavonols content (r=0.718). Ratio of betaxanthins to betacyanins (0.0-1.41) was negatively correlated with L value (r=-0.744). Whereas, high TAC values (119.8-335.9mmol Trolox equivalents/kg) were negatively correlated with L value (r=-0.779), but positively with betalains (r=0.730), as well as with free (r=0.639), bound (r=0.558) and total phenolic compounds (r=0.676). Unexploited coloured quinoa seeds are proposed as a valuable natural source of phenolics and betalains with high antioxidant capacity. PMID:25863614

  9. Extraction of phenolic compounds from extra virgin olive oil by a natural deep eutectic solvent: Data on UV absorption of the extracts.

    PubMed

    Paradiso, Vito Michele; Clemente, Antonia; Summo, Carmine; Pasqualone, Antonella; Caponio, Francesco

    2016-09-01

    This data article refers to the paper "Towards green analysis of virgin olive oil phenolic compounds: extraction by a natural deep eutectic solvent and direct spectrophotometric detection" [1]. A deep eutectic solvent (DES) based on lactic acid and glucose was used as green solvent for phenolic compounds. Eight standard phenolic compounds were solubilized in the DES. Then, a set of extra virgin olive oil (EVOO) samples (n=65) were submitted to liquid-liquid extraction by the DES. The standard solutions and the extracts were analyzed by UV spectrophotometry. This article reports the spectral data of both the standard solutions and the 65 extracts, as well as the total phenolic content of the corresponding oils, assessed by the Folin-Ciocalteu assay. PMID:27504478

  10. Phenolic Compounds and Bioactivity of Healthy and Infected Grapevine Leaf Extracts from Red Varieties Merlot and Vranac (Vitis vinifera L.).

    PubMed

    Anđelković, Marko; Radovanović, Blaga; Anđelković, Ana Milenkovic; Radovanović, Vladimir

    2015-09-01

    We investigated the phenolic composition, radical scavenging activity, and antimicrobial activity of grapevine leaf extracts from two red grape varieties, Vranac and Merlot (Vitis vinifera L.). The extracts were prepared from healthy grapevine leaves and those infected by Plasmopara viticola (downy mildew). The phenolic composition of the grapevine leaf extracts was determined using spectrophotometric assays and reverse-phase high performance liquid chromatography (RP-HPLC). The radical scavenging activity of grapevine leaf extracts was determined by the 2,2-diphenyl-1-picrylhydrazyl assay, and their antimicrobial activity was determined by microwell dilution tests. The total phenolic content was higher in healthy grapevine leaf extracts than in infected grapevine leaf extracts. The RP-HPLC analysis detected significant amounts of flavonols, phenolic acids, and flavan-3-ols, and small amounts of stilbenes in the grapevine leaf extracts. Compared with the infected grapevine leaf extracts, the healthy grapevine leaf extracts were richer in flavonols, phenolic acids, and flavan-3-ols, but had lower stilbenes contents. All extracts showed strong free radical scavenging activity, which was strongly correlated with the total phenolic content (R(2) = 0.978). The extracts showed a stronger antimicrobial activity towards Gram-positive bacterial strains than towards Gram-negative bacterial strains and yeast. The phenolic compounds in grapevine leaves were responsible for their strong radical scavenging and antimicrobial activities. Together, these results demonstrate that grapevine leaves have high nutritional value and can be used as a fresh food and to prepare extracts that can be used as additives in food and medicines. PMID:26174183

  11. Highly Efficient Extraction of Phenolic Compounds by Use of Magnetic Room Temperature Ionic Liquids for Environmental Remediation

    PubMed Central

    Deng, Ning; Li, Min; Zhao, Lijie; Lu, Chengfei; de Rooy, Sergio L.; Warner, Isiah M.

    2011-01-01

    A hydrophobic magnetic room temperature ionic liquid (MRTIL), trihexyltetradecylphosphonium tetrachloroferrate(III) ([3C6PC14][FeCl4]), was synthesized from trihexyltetradecylphosphonium chloride and FeCl3·6H2O. This MRTIL was investigated as a possible separation agent for solvent extraction of phenolic compounds from aqueous solution. Due to its strong paramagnetism, [3C6PC14][FeCl4] responds to an external neodymium magnet, which was employed in the design of a novel magnetic extraction technique. The conditions for extraction, including extraction time, volume ratio between MRTIL and aqueous phase, pH of aqueous solution, and structures of phenolic compounds were investigated and optimized. The magnetic extraction of phenols achieved equilibrium in 20 min and the phenolic compounds were found to have higher distribution ratios under acidic conditions. In addition, it was observed that phenols containing a greater number of chlorine or nitro substitutents exhibited higher distribution ratios. For example, the distribution ratio of phenol (DPh) was 107. In contrast, 3,5-dichlorophenol distribution ratio (D3,5-DCP) had a much higher value of 6372 under identical extraction conditions. When compared with four selected traditional non-magnetic room temperature ionic liquids, our [3C6PC14][FeCl4] exhibited significantly higher extraction efficiency under the same experimental conditions used in this work. Pentachlorophenol, a major component in the contaminated soil sample obtained from a superfund site, was successfully extracted and removed by use of [3C6PC14][FeCl4] with high extraction efficiency. Pentachlorophenol concentration was dramatically reduced from 7.8 μg.mL−1 to 0.2 μg.mL−1 after the magnetic extraction by use of [3C6PC14][FeCl4]. PMID:21783320

  12. Cross-reactivity of antibodies with phenolic compounds in pistachios during quantification of ochratoxin A by commercial enzyme-linked immunosorbent assay kits.

    PubMed

    Lee, Hyun Jung; Meldrum, Alexander D; Rivera, Nicholas; Ryu, Dojin

    2014-10-01

    Ochratoxin A (OTA), a nephrotoxic mycotoxin, naturally occurs in wide range of agricultural commodities. Typical screening of OTA involves various enzyme-linked immunosorbent assay (ELISA) methods. Pistachio (Pistacia vera L.) is a rich source of phenolic compounds that may result in a false positive due to structural similarities to OTA. The present study investigated the cross-reactivity profiles of phenolic compounds using two commercial ELISA test kits. High-performance liquid chromatography was used to confirm the concentration of OTA in the pistachio samples and compared with the results obtained from ELISA. When the degree of interaction and 50 % inhibitory concentration of phenolic compounds were determined, the cross-reactivity showed a pattern similar to that observed with the commercial ELSIA kits, although quantitatively different. In addition, the degree of interaction increased with the increasing concentration of phenolic compounds. The ELISA value had stronger correlations with the content of total phenolic compound, gallic acid, and catechin (R(2) = 0.757, 0.732, and 0.729, respectively) compared with epicatechin (R(2) = 0.590). These results suggest that phenolic compounds in pistachio skins may cross-react with the OTA antibody and lead to a false positive or to an overestimation of OTA concentration in ELISA-based tests.

  13. Effect of cadmium on phenolic compounds, antioxidant enzyme activity and oxidative stress in blueberry (Vaccinium corymbosum L.) plantlets grown in vitro.

    PubMed

    Manquián-Cerda, K; Escudey, M; Zúñiga, G; Arancibia-Miranda, N; Molina, M; Cruces, E

    2016-11-01

    Cadmium (Cd(2+)) can affect plant growth due to its mobility and toxicity. We evaluated the effects of Cd(2+) on the production of phenolic compounds and antioxidant response of Vaccinium corymbosum L. Plantlets were exposed to Cd(2+) at 50 and 100µM for 7, 14 and 21 days. Accumulation of malondialdehyde (MDA), hydrogen peroxide (H2O2) and the antioxidant enzyme SOD was determined. The profile of phenolic compounds was evaluated using LC-MS. The antioxidant activity was measured using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and the ferric reducing antioxidant power test (FRAP). Cd(2+) increased the content of MDA, with the highest increase at 14 days. The presence of Cd(2+) resulted in changes in phenolic compounds. The main phenolic compound found in blueberry plantlets was chlorogenic acid, whose abundance increased with the addition of Cd(2+) to the medium. The changes in the composition of phenolic compounds showed a positive correlation with the antioxidant activity measured using FRAP. Our results suggest that blueberry plantlets produced phenolic compounds with reducing capacity as a selective mechanism triggered by the highest activity of Cd(2+). PMID:27485373

  14. Dietary Phenolic Compounds Interfere with the Fate of Hydrogen Peroxide in Human Adipose Tissue but Do Not Directly Inhibit Primary Amine Oxidase Activity

    PubMed Central

    Carpéné, Christian; Hasnaoui, Mounia; Balogh, Balázs; Matyus, Peter; Fernández-Quintela, Alfredo; Rodríguez, Víctor; Mercader, Josep; Portillo, Maria P.

    2016-01-01

    Resveratrol has been reported to inhibit monoamine oxidases (MAO). Many substrates or inhibitors of neuronal MAO interact also with other amine oxidases (AO) in peripheral organs, such as semicarbazide-sensitive AO (SSAO), known as primary amine oxidase, absent in neurones, but abundant in adipocytes. We asked whether phenolic compounds (resveratrol, pterostilbene, quercetin, and caffeic acid) behave as MAO and SSAO inhibitors. AO activity was determined in human adipose tissue. Computational docking and glucose uptake assays were performed in 3D models of human AO proteins and in adipocytes, respectively. Phenolic compounds fully inhibited the fluorescent detection of H2O2 generated during MAO and SSAO activation by tyramine and benzylamine. They also quenched H2O2-induced fluorescence in absence of biological material and were unable to abolish the oxidation of radiolabelled tyramine and benzylamine. Thus, phenolic compounds hampered H2O2 detection but did not block AO activity. Only resveratrol and quercetin partially impaired MAO-dependent [14C]-tyramine oxidation and behaved as MAO inhibitors. Phenolic compounds counteracted the H2O2-dependent benzylamine-stimulated glucose transport. This indicates that various phenolic compounds block downstream effects of H2O2 produced by biogenic or exogenous amine oxidation without directly inhibiting AO. Phenolic compounds remain of interest regarding their capacity to limit oxidative stress rather than inhibiting AO. PMID:26881018

  15. Determination of free and bound phenolic compounds in buckwheat spaghetti by RP-HPLC-ESI-TOF-MS: effect of thermal processing from farm to fork.

    PubMed

    Verardo, Vito; Arraez-Roman, David; Segura-Carretero, Antonio; Marconi, Emanuele; Fernandez-Gutierrez, Alberto; Caboni, Maria Fiorenza

    2011-07-27

    Nowadays there is considerable interest in the consumption of alternative crops as potential recipes for gluten-free products production. Therefore, the use of buckwheat for the production of gluten-free pasta has been investigated in the present study. RP-HPLC-ESI-TOF-MS has been applied for the separation and characterization of free and bound phenolic compounds in buckwheat flour and buckwheat spaghetti. Thus, 32 free and 24 bound phenolic compounds in buckwheat flour and spaghetti have been characterized and quantified. To the authors' knowledge, protochatechuic-4-O-glucoside acid and procyanidin A have been detected in buckwheat for the first time. The results have demonstrated a decrease of total free phenolic compounds from farm to fork (from flour to cooked spaghetti) of about 74.5%, with a range between 55.3 and 100%, for individual compounds. The decrease in bound phenols was 80.9%, with a range between 46.2 and 100%. The spaghetti-making process and the cooking caused losses of 46.1 and 49.4% of total phenolic compounds, respectively. Of the total phenolic compounds present in dried spaghetti, 11.6% were dissolved in water after cooking.

  16. Dietary fiber and phenolic compounds as functional ingredients: interaction and possible effect after ingestion.

    PubMed

    Quirós-Sauceda, A E; Palafox-Carlos, H; Sáyago-Ayerdi, S G; Ayala-Zavala, J F; Bello-Perez, L A; Alvarez-Parrilla, E; de la Rosa, L A; González-Córdova, A F; González-Aguilar, G A

    2014-06-01

    Dietary fiber and phenolic compounds are two recognized dietary factors responsible for potential effects on human health; therefore, they have been widely used to increase functionality of some foods. This paper focuses on showing the use of both substances as functional ingredients for enriching foods, and at the same time, describes the use of a single material that combines the properties of the two types of substances. The last part of the work describes some facts related to the interaction between dietary fiber and phenolic compounds, which could affect the bioaccessibility and absorption of phenolics in the gut. In this sense, the purpose of the present review is to compile and analyze evidence relating to the use of dietary fiber and phenolic compounds to enhance technological and nutritional properties of foods and hypothesize some of the possible effects in the gut after their ingestion.

  17. The occurrence and fate of phenolic compounds in a coking wastewater treatment plant.

    PubMed

    Zhang, Wanhui; Wei, Chaohai; Feng, Chunhua; Ren, Yuan; Hu, Yun; Yan, Bo; Wu, Chaofei

    2013-01-01

    The occurrence of 14 phenolic compounds (PCs) was assessed in the raw, treated wastewater, dewatered sludge and gas samples from a coking wastewater treatment plant (WWTP) in China. It was found that 3-cresol was the dominant compound in the raw coking wastewater with a concentration of 183 mg L(-1), and that chlorophenols and nitrophenols were in the level of μg L(-1). Phenol was the dominant compound in the gas samples, while 2,4,6-trichlorophenol predominated in the dewatered sludge sample. The anaerobic and aerobic tanks played key roles in the elimination of chlorophenols and phenols, respectively. Analysis of daily mass flows of PCs in WWTP showed that 89-98% of phenols and 83-89% of nitrophenols were biodegraded, and that 44-69% of chlorophenols were adsorbed to sludge, indicating that the fate of PCs was highly influenced by their biodegradability and physical-chemical property. PMID:23863439

  18. Antioxidant properties of ferulic acid and its related compounds.

    PubMed

    Kikuzaki, Hiroe; Hisamoto, Masashi; Hirose, Kanae; Akiyama, Kayo; Taniguchi, Hisaji

    2002-03-27

    Antioxidant activity of 24 ferulic acid related compounds together with 6 gallic acid related compounds was evaluated using several different physical systems as well as their radical scavenging activity. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) decreased in the order caffeic acid > sinapic acid > ferulic acid > ferulic acid esters > p-coumaric acid. In bulk methyl linoleate, test hydroxycinnamic acids and ferulic acid esters showed antioxidant activity in parallel with their radical scavenging activity. In an ethanol-buffer solution of linoleic acid, the activity of test compounds was not always associated with their radical scavenging activity. Ferulic acid was most effective among the tested phenolic acids. Esterification of ferulic acid resulted in increasing activity. The activity of alkyl ferulates was somewhat influenced by the chain length of alcohol moiety. When the inhibitory effects of alkyl ferulates against oxidation of liposome induced by AAPH were tested, hexyl, octyl, and 2-ethyl-1-hexyl ferulates were more active than the other alkyl ferulates. Furthermore, lauryl gallate is most effective among the tested alkyl gallates. These results indicated that not only the radical scavenging activity of antioxidants, but also their affinity with lipid substrates, might be important factors in their activity.

  19. Bioactive Phenylpropanoids, Phenolic Acid and Phytosterol from Landolphia owariensis P. Beauv Stringy Seed Pulp.

    PubMed

    Okonkwo, Tochukwu J N; Osadebe, Patience O; Proksch, Peter

    2016-01-01

    Landolphia owariensis P. Beauv is economically important for latex/rubber and folklore medicine. Its stringy seed pulp is freely eaten by humans and animals. Thus, L. owariensis stringy seed pulp was extracted serially with hexane and acetone to isolate and characterize its active pharmaceutical ingredients. Solvent/solvent partition and chromatographic separations afforded four bioactive compounds, (E)-3-(3,4-Dihydroxylcinnamoyl)quinic acid [(E)-Chlorogenic acid], I; (E)-3-(3,4-Dihydroxylcinnamoyl)quinic acid methyl ester [(E)-Chlorogenic acid methyl ester], II; 3,4-Dihydroxylbenzoic acid, (Protocatechuic acid), III; and 22,23-Dihydrostigmaster-3β-ol (3β-Sitosterol) (IV). Structures of I, II and III were assigned by combinations of high-performance liquid chromatography-ultraviolet-visible spectroscopy, 1D and 2D nuclear magnetic resonance spectroscopy, high-performance liquid chromatography-mass spectrometry and reference to published literatures, while compound IV was identified by chemical methods and gas chromatography-mass spectrometry. The phenylpropanoids and phenolic acid (compounds I, II and III) are notable standard antioxidants with confirmed hepatic-protective activity and other exciting biological activities. Compound IV has been reported to possess anti-inflammatory activity, anti-colon cancer action and a cholesterol-lowering effect. The described compounds are important medicinal constituents of L. owariensis stringy seed pulp, and this is the first major report on the phytochemistry of L. owariensis P. Beauv.

  20. Bioactive Phenylpropanoids, Phenolic Acid and Phytosterol from Landolphia owariensis P. Beauv Stringy Seed Pulp.

    PubMed

    Okonkwo, Tochukwu J N; Osadebe, Patience O; Proksch, Peter

    2016-01-01

    Landolphia owariensis P. Beauv is economically important for latex/rubber and folklore medicine. Its stringy seed pulp is freely eaten by humans and animals. Thus, L. owariensis stringy seed pulp was extracted serially with hexane and acetone to isolate and characterize its active pharmaceutical ingredients. Solvent/solvent partition and chromatographic separations afforded four bioactive compounds, (E)-3-(3,4-Dihydroxylcinnamoyl)quinic acid [(E)-Chlorogenic acid], I; (E)-3-(3,4-Dihydroxylcinnamoyl)quinic acid methyl ester [(E)-Chlorogenic acid methyl ester], II; 3,4-Dihydroxylbenzoic acid, (Protocatechuic acid), III; and 22,23-Dihydrostigmaster-3β-ol (3β-Sitosterol) (IV). Structures of I, II and III were assigned by combinations of high-performance liquid chromatography-ultraviolet-visible spectroscopy, 1D and 2D nuclear magnetic resonance spectroscopy, high-performance liquid chromatography-mass spectrometry and reference to published literatures, while compound IV was identified by chemical methods and gas chromatography-mass spectrometry. The phenylpropanoids and phenolic acid (compounds I, II and III) are notable standard antioxidants with confirmed hepatic-protective activity and other exciting biological activities. Compound IV has been reported to possess anti-inflammatory activity, anti-colon cancer action and a cholesterol-lowering effect. The described compounds are important medicinal constituents of L. owariensis stringy seed pulp, and this is the first major report on the phytochemistry of L. owariensis P. Beauv. PMID:26537109

  1. Bioremediation of phenolic compounds from water with plant root surface peroxidases

    SciTech Connect

    Adler, P.R.; Arora, R.; El Ghaouth, A.

    1994-09-01

    Peroxidases have been shown to polymerize phenolic compounds, thereby removing them from solution by precipitation. Others have studied the role of root surface associated peroxidases as a defense against fungal root pathogens; however, their use in detoxification of organic pollutants in vivo at the root surface has not been studied. Two plant species, waterhyacinth [Eichhornia crassipes (C. Mart) Solms-Laub.] and tomato (Lycopersicon esculentum L.), were tested for both in vitro and in vivo peroxidase activity on the root surface. In vitro studies indicated that root surface peroxidase activities were 181 and 78 nmol tetraguaiacol formed min{sup -1} g{sup -1} root fresh wt., for tomato and waterhyacinth, respectively. Light microscope studies revealed that guaiacol was polymerized in vivo at the root surface. Although peroxidase was evenly distributed on tomato roots, it was distributed patchily on waterhyacinth roots. In vitro studies using gas chromatography-mass spectrometry (GC-MS) showed that the efficiency of peroxidase to polymerize phenols vary with phenolic compound. We suggest that plants may be utilized as a source of peroxidases for removal of phenolic compounds that are on the EPA priority pollutant list and that root surface peroxidases may minimize the absorption of phenolic compounds into plants by precipitating them at the root surface. In this study we have identified a new use for root-associated proteins in ecologically engineering plant systems for bioremediation of phenolic compounds in the soil and water environment. 25 refs., 2 figs., 2 tabs.

  2. Suitability of antioxidant capacity, flavonoids and phenolic acids for floral authentication of honey. Impact of industrial thermal treatment.

    PubMed

    Escriche, Isabel; Kadar, Melinda; Juan-Borrás, Marisol; Domenech, Eva

    2014-01-01

    Total antioxidant activity, physicochemical parameters, and the profile of flavonoids and phenolic acid compounds were evaluated for: their ability to distinguish between the botanical origins of four types of Spanish honey, the impact of industrial thermal treatment, and the effect of the year of collection. Citrus honey had the lowest levels of all the analysed variables, then rosemary and polyfloral, and honeydew the highest ones. Botanical origin affects the profile of flavonoids and phenolic compounds sufficiently to permit discrimination thanks to the predominance of particular compounds such as: hesperetin (in citrus honey); kaempferol, chrysin, pinocembrin, caffeic acid and naringenin (in rosemary honey) and myricetin, quercetin, galangin and particularly p-coumaric acid (in honeydew honey). The impact of industrial thermal treatments is lower than the expected variability as a consequence of the year of collection, though neither factor has enough influence to alter these constituent compounds to the point of affecting the discrimination of honey by botanical origin.

  3. Analysis of Phenolic Compounds in Some Medicinal Herbs by LC-MS.

    PubMed

    Matei, Alina O; Gatea, Florentina; Radu, Gabriel L

    2015-08-01

    In this paper, a liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry in negative mode method was developed for the identification and quantitative determination of 13 individual phenolics (chlorogenic acid, caffeic acid, coumaric acid, ferulic acid, (+)-catechin, (-)-epicatechin, rutin, quercitrin, isoquercitrin, fisetin, isorhamnetin, hesperidin and chrysin) from ethanolic extracts [30, 50 and 70% (w/v)] of Calendula officinalis, Hypericum perforatum, Galium verum and Origanum vulgare and some commercial extracts of these medicinal herbs. Correlation coefficients (r(2)) from calibration curves for all the compounds were between 0.9971 and 0.9996. Limit of detection was in the range of 0.070-0.280 µg/mL and limit of quantification was from 0.233 to 0.932 µg/mL. The method was partially validated and the results obtained are: the intra- and interday relative standard deviation values were within 0.086 and 2.821% and recovery values vary from 95.84% (coumaric acid) to 103.20% (rutin). PMID:25583972

  4. Analysis of Phenolic Compounds in Some Medicinal Herbs by LC-MS.

    PubMed

    Matei, Alina O; Gatea, Florentina; Radu, Gabriel L

    2015-08-01

    In this paper, a liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry in negative mode method was developed for the identification and quantitative determination of 13 individual phenolics (chlorogenic acid, caffeic acid, coumaric acid, ferulic acid, (+)-catechin, (-)-epicatechin, rutin, quercitrin, isoquercitrin, fisetin, isorhamnetin, hesperidin and chrysin) from ethanolic extracts [30, 50 and 70% (w/v)] of Calendula officinalis, Hypericum perforatum, Galium verum and Origanum vulgare and some commercial extracts of these medicinal herbs. Correlation coefficients (r(2)) from calibration curves for all the compounds were between 0.9971 and 0.9996. Limit of detection was in the range of 0.070-0.280 µg/mL and limit of quantification was from 0.233 to 0.932 µg/mL. The method was partially validated and the results obtained are: the intra- and interday relative standard deviation values were within 0.086 and 2.821% and recovery values vary from 95.84% (coumaric acid) to 103.20% (rutin).

  5. Identification and quantification of phenolic compounds in berries of Fragaria and Rubus species (family Rosaceae).

    PubMed

    Määttä-Riihinen, Kaisu R; Kamal-Eldin, Afaf; Törrönen, A Riitta

    2004-10-01

    High-performance liquid chromatography combined with diode array and electrospray ionization mass spectrometric detection was used to study soluble and insoluble forms of phenolic compounds in strawberries, raspberries (red and yellow cultivated and red wild), arctic bramble, and cloudberries. Hydroxycinnamic acids were present as free forms in cloudberries and mainly as sugar esters in the other berries. Quercetin 3-glucuronide was the typical flavonol glycoside in all of the berries studied. The composition of the predominant anthocyanins can be used to distinguish the studied red Rubus species from each other since cyanidin was glycosylated typically with 3-sophorose (56%) in cultivated red raspberry, with 3-sophorose (30%) and 3-glucose (27%) in wild red raspberry, and with 3-rutinose (80%) in arctic bramble. Ellagic acid was present as free and glycosylated forms and as ellagitannins of varying degrees of polymerization. Comparable levels of ellagitannins were obtained by the analysis of soluble ellagitannins as gallic acid equivalents and by the analysis of ellagic acid equivalents released by acid hydrolysis of the extracts. PMID:15453684

  6. Phenolic acids isolated from the fungus Schizophyllum commune exert analgesic activity by inhibiting voltage-gated sodium channels.

    PubMed

    Yao, Hui-Min; Wang, Gan; Liu, Ya-Ping; Rong, Ming-Qiang; Shen, Chuan-Bin; Yan, Xiu-Wen; Luo, Xiao-Dong; Lai, Ren

    2016-09-01

    The present study was designed to search for compounds with analgesic activity from the Schizophyllum commune (SC), which is widely consumed as edible and medicinal mushroom world. Thin layer chromatography (TLC), tosilica gel column chromatography, sephadex LH 20, and reverse-phase high performance liquid chromatography (RP-HPLC) were used to isolate and purify compounds from SC. Structural analysis of the isolated compounds was based on nuclear magnetic resonance (NMR). The effects of these compounds on voltage-gated sodium (NaV) channels were evaluated using patch clamp. The analgesic activity of these compounds was tested in two types of mouse pain models induced by noxious chemicals. Five phenolic acids identified from SC extracts in the present study included vanillic acid, m-hydroxybenzoic acid, o-hydroxybenzeneacetic acid, 3-hydroxy-5-methybenzoic acid, and p-hydroxybenzoic acid. They inhibited the activity of both tetrodotoxin-resistant (TTX-r) and tetrodotoxin-sensitive (TTX-s) NaV channels. All the compounds showed low selectivity on NaV channel subtypes. After intraperitoneal injection, three compounds of these compounds exerted analgesic activity in mice. In conclusion, phenolic acids identified in SC demonstrated analgesic activity, facilitating the mechanistic studies of SC in the treatment of neurasthenia. PMID:27667511

  7. Evolution of aroma and phenolic compounds during ripening of 'superior seedless' grapes.

    PubMed

    Hellín, Pilar; Manso, Angela; Flores, Pilar; Fenoll, José

    2010-05-26

    The evolution of aroma and phenolic compounds was studied during ripening of Vitis vinifera cv. 'Superior Seedless' grapes in two consecutive years. The major free detected compounds were citral, geraniol, and benzyl alcohol whereas geraniol, citral, nerol, citronellol, dienediol I, linalol oxide I, linalol oxide II, benzyl alcohol, and 2-phenylethanol were identified in the glycosidically bound fraction. Concentrations of the main free terpene alcohols responsible for 'Superior Seedless' aroma decreased during grape development, and bound compounds became predominant at grape maturity. Calculation of odor activity values showed that geraniol was the most active odorant followed to a lesser extent by citral and nerol. With regard to phenolic compound evolution, flavan-3-ols and flavonols were maximal at veraison and decreased throughout the ripening, stilbenes content decreased from the first stage, and total phenolics increased to show a maximum in the ripe grapes. At ripening, quercetin 3-O-glucoside and catechin were the main compounds detected in 'Superior Seedless'. PMID:20438135

  8. Flavonoids and phenolic acids of Nepeta cataria L. var. citriodora (Becker) Balb. (Lamiaceae).

    PubMed

    Modnicki, Daniel; Tokar, Magdalena; Klimek, Barbara

    2007-01-01

    Luteolin 7-O-glucuronide, luteolin 7-O-glucurono-(1-->6)-glucoside, apigenin 7-O-glucuronide as well as free aglycones luteolin and apigenin have been isolated from lemon catnip herb (Nepeta cataria L. var citriodora). Luteolin 7-O-glucurono-(1-->6)-glucoside is probably a new compound, for the first time described. Two minor constituents of flavonoid fraction have been identified as apigenin 7-O-glucoside and luteolin 7-O-glucoside by means of HPLC method. The percentage of total flavonoids determined by use of spectrophotometric method was in the range from 0.30 to 0.46% of dry mass. In phenolic acid fraction, caffeic, rosmarinic and p-coumaric acids have been identified. Total amount of phenolic acids determined by spectrophotometric method was in the range of 0.75% to 1.4 % and the content of rosmarinic acid quantified by HPLC method fluctuated in the wide range from 0.06% to 0.15% depending on the sample. The results of the investigations showed that the composition of flavonoid compounds and phenolic acids in lemon catnip are similar to those in lemon balm (Melissa officinalis L.). The amount of flavonoids are similar in both plants, and the percentage of rosmarinic acid is about ten times lower in lemon catnip than in lemon balm. The presence of luteolin, apigenin and their glycosides, caffeic acid as well as the previously described terpenoids (ursolic acid, citral, nerol. geraniol) suggests the possibility of the use of lemon catnip herb as a constituent of phytopharmaceutical preparations with mild sedative, antispasmodic, antioxidative and antiinflammatory action.

  9. Flavonoids and phenolic acids of Nepeta cataria L. var. citriodora (Becker) Balb. (Lamiaceae).

    PubMed

    Modnicki, Daniel; Tokar, Magdalena; Klimek, Barbara

    2007-01-01

    Luteolin 7-O-glucuronide, luteolin 7-O-glucurono-(1-->6)-glucoside, apigenin 7-O-glucuronide as well as free aglycones luteolin and apigenin have been isolated from lemon catnip herb (Nepeta cataria L. var citriodora). Luteolin 7-O-glucurono-(1-->6)-glucoside is probably a new compound, for the first time described. Two minor constituents of flavonoid fraction have been identified as apigenin 7-O-glucoside and luteolin 7-O-glucoside by means of HPLC method. The percentage of total flavonoids determined by use of spectrophotometric method was in the range from 0.30 to 0.46% of dry mass. In phenolic acid fraction, caffeic, rosmarinic and p-coumaric acids have been identified. Total amount of phenolic acids determined by spectrophotometric method was in the range of 0.75% to 1.4 % and the content of rosmarinic acid quantified by HPLC method fluctuated in the wide range from 0.06% to 0.15% depending on the sample. The results of the investigations showed that the composition of flavonoid compounds and phenolic acids in lemon catnip are similar to those in lemon balm (Melissa officinalis L.). The amount of flavonoids are similar in both plants, and the percentage of rosmarinic acid is about ten times lower in lemon catnip than in lemon balm. The presence of luteolin, apigenin and their glycosides, caffeic acid as well as the previously described terpenoids (ursolic acid, citral, nerol. geraniol) suggests the possibility of the use of lemon catnip herb as a constituent of phytopharmaceutical preparations with mild sedative, antispasmodic, antioxidative and antiinflammatory action. PMID:17695148

  10. Flavonoids and phenolic acids from cranberry juice are bioavailable and bioactive in healthy older adults.

    PubMed

    McKay, Diane L; Chen, C-Y Oliver; Zampariello, Carly A; Blumberg, Jeffrey B

    2015-02-01

    Cranberries (Vaccinium macrocarpon) are a rich source of phenolic phytochemicals, which likely contribute to their putative health benefits. A single-dose pharmacokinetic trial was conducted in 10 healthy adults ⩾50y to evaluate the acute (24-h) absorption and excretion of flavonoids, phenolic acids and proanthocyanidins (PACs) from a low-calorie cranberry juice cocktail (54% juice). Inter-individual variability was observed in the Cmax and Tmax of many of these compounds in both plasma and urine. The sum total concentration of phenolics detected in plasma reached a peak of 34.2μg/ml between 8 and 10h, while in urine this peak was 269.8μg/mg creatinine, and appeared 2-4h earlier. The presence of PAC-A2 dimers in human urine has not previously been reported. After cranberry juice consumption, plasma total antioxidant capacity assessed using ORAC and TAP assays correlated with individual metabolites. Our results show phenolic compounds in cranberry juice are bioavailable and exert antioxidant actions in healthy older adults.

  11. Photocatalysis of phenol and salicyclic acid by nanostructured titania powders

    SciTech Connect

    Fotou, G.P.; Pratsinis, S.E.

    1995-12-31

    The photocatalytic destruction of phenol and salicylic acid was studied in aqueous suspensions of titania powders made in flame reactors. These powders were made in six hydrocarbon diffusion flames by hydrolysis and oxidation of TiCl{sub 4} that resulted in powders of high specific surface area and high anatase content. The photoactivity of the flame-made titania powders was compared with that of commercially available powders. Doping the titania with SiO{sub 2} was detrimental to the photoactivity of the powders in aerated solutions in contrast to non-aerated solutions. Titania powders in the range of 20-40 nm containing small amounts of rutile were more active than pure anatase powders. The phenol degradation reaction followed a first-order law while the Langmuir-Hinshelwood model was found to most accurately represent the photodegradation of salicylic acid.

  12. Influence of alternative electron acceptors on the anaerobic biodegradability of chlorinated phenols and benzoic acids

    SciTech Connect

    Haeggblom, M.M.; Rivera, M.D.; Young, L.Y. )

    1993-04-01

    Methanogeneic conditions can promote the biodegradation of a number of halogenated aromatic compounds. This study, using sediments from freshwater and estuarine sites, is an evaluation of the anaerobic biodegradability of monochlorinated phenols and benzoic acids coupled to denitrification, sulfidogenesis, and methanogenesis. The results indicate that chlorinated phenols and benzoic acids are biodegradable under at least one set of anaerobic conditions. Metabolism depends both on the electron acceptor available and on the position of the chlorine substituent. Presence of alternative electron acceptors, nitrate, sulfate, and carbonate, can affect degradation rates and substrate specificities. Since contaminated sites usually have mixtures of wastes, bioremediation efforts may need to consider the activities of diverse anaerobic communities to carry out effective treatment of all components. 37 refs., 4 figs., 4 tabs.

  13. Elevated carbon dioxide increases contents of flavonoids and phenolic compounds, and antioxidant activities in Malaysian young ginger (Zingiber officinale Roscoe.) varieties.

    PubMed

    Ghasemzadeh, Ali; Jaafar, Hawa Z E; Rahmat, Asmah

    2010-11-01

    Zingiber officinale Roscoe. (Family Zingiberaceae) is well known in Asia. The plant is widely cultivated in village gardens in the tropics for its medicinal properties and as a marketable spice in Malaysia. Ginger varieties are rich in physiologically active phenolics and flavonoids with a range of pharmacological activities. Experiments were conducted to determine the feasibility of increasing levels of flavonoids (quercetin, rutin, catechin, epicatechin, kaempferol, naringenin, fisetin and morin) and phenolic acid (gallic acid, vanillic acid, ferulic acid, tannic acid, cinnamic acid and salicylic acid), and antioxidant activities in different parts of Malaysian young ginger varieties (Halia Bentong and Halia Bara) with CO(2) enrichment in a controlled environment system. Both varieties showed an increase in phenolic compounds and flavonoids in response to CO(2) enrichment from 400 to 800 µmol mol-1 CO(2). These increases were greater in rhizomes compared to leaves. High performance liquid chromatography (HPLC) results showed that quercetin and gallic acid were the most abundant flavonoid and phenolic acid in Malaysian young ginger varieties. Under elevated CO(2) conditions, kaempferol and fisetin were among the flavonoid compounds, and gallic acid and vanillic acid were among the phenolic compounds whose levels increased in both varieties. As CO(2) concentration was increased from 400 to 800 µmol mol-1, free radical scavenging power (DPPH) increased about 30% in Halia Bentong and 21.4% in Halia Bara; and the rhizomes exhibited more enhanced free radical scavenging power, with 44.9% in Halia Bentong and 46.2% in Halia Bara. Leaves of both varieties also displayed good levels of flavonoid compounds and antioxidant activities. These results indicate that the yield and pharmaceutical quality of Malaysian young ginger varieties can be enhanced by controlled environment production and CO(2) enrichment. PMID:21060298

  14. 40 CFR 721.3700 - Fatty acid, ester with styrenated phenol, ethylene oxide adduct.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... phenol, ethylene oxide adduct. 721.3700 Section 721.3700 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.3700 Fatty acid, ester with styrenated phenol... chemical substance identified generically as fatty acid, ester with styrenated phenol, ethylene...

  15. 40 CFR 721.3700 - Fatty acid, ester with styrenated phenol, ethylene oxide adduct.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... phenol, ethylene oxide adduct. 721.3700 Section 721.3700 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.3700 Fatty acid, ester with styrenated phenol... chemical substance identified generically as fatty acid, ester with styrenated phenol, ethylene...

  16. Extraction and HPLC analysis of phenolic compounds in leaves, stalks, and textile fibers of Urtica dioica L.

    PubMed

    Pinelli, Patrizia; Ieri, Francesca; Vignolini, Pamela; Bacci, Laura; Baronti, Silvia; Romani, Annalisa

    2008-10-01

    In the present study the phenolic composition of leaves, stalks, and textile fiber extracts from Urtica dioica L. is described. Taking into account the increasing demand for textile products made from natural fibers and the necessity to create sustainable "local" processing chains, an Italian project was funded to evaluate the cultivation of nettle fibers in the region of Tuscany. The leaves of two nettle samples, cultivated and wild (C and W), contain large amounts of chlorogenic and 2- O-caffeoylmalic acid, which represent 71.5 and 76.5% of total phenolics, respectively. Flavonoids are the main class in the stalks: 54.4% of total phenolics in C and 31.2% in W samples. Anthocyanins are second in quantitative importance and are present only in nettle stalks: 28.6% of total phenolics in C and 24.4% in W extracts. Characterization of phenolic compounds in nettle extracts is an important result with regard to the biological properties (antioxidant and antiradical) of these metabolites for their possible applications in various industrial activities, such as food/feed, cosmetics, phytomedicine, and textiles. PMID:18778029

  17. Elucidating the role of phenolic compounds in the effectiveness of DOM adsorption on novel tailored activated carbon.

    PubMed

    Yan, Liang; Fitzgerald, Martha; Khov, Cindy; Schafermeyer, Amy; Kupferle, Margaret J; Sorial, George A

    2013-11-15

    Two novel tailored activated carbons (BC-41-OG and BC-41-MnN) with favorable physicochemical characteristics were successfully prepared for adsorption of dissolved natural organic matter (DOM) by applying systematically chemical and thermal treatment. This research was conducted to investigate the impact of the presence of phenolics on the adsorption capacity of DOM. Isotherm tests were performed for both humic acid (HA) and phenolics on both novel tailored activated carbons and commercial activated carbon F400. The presence of phenolics display a significant effect on hindering the adsorption of HA, however; the physicochemical characteristics of novel activated carbons (surface metal oxides and mesoporosity) can play an important role in alleviating this effect. In contrast, F400, with a relatively lower mesoporosity and surface basicity as compared to the developed adsorbents, was severely impacted by the oligomerization of phenolic compounds. The adsorption capacity of DOM in presence of phenolics was further studied in a continuous flow microcolumn system. The column results showed that both BC-41-OG and BC-41-MnN have not only higher HA adsorption capacity but also better selective adsorption ability than F400.

  18. Variability of virgin olive oil phenolic compounds in a segregating progeny from a single cross in Olea europaea L. and sensory and nutritional quality implications.

    PubMed

    Pérez, Ana G; León, Lorenzo; Pascual, Mar; Romero-Segura, Carmen; Sánchez-Ortiz, Araceli; de la Rosa, Raúl; Sanz, Carlos

    2014-01-01

    Virgin olive oil phenolic compounds are responsible for its nutritional and sensory quality. The synthesis of phenolic compounds occurs when enzymes and substrates meet as olive fruit is crushed during the industrial process to obtain the oil. The genetic variability of the major phenolic compounds of virgin olive oil was studied in a progeny of the cross of Picual x Arbequina olive cultivars (Olea europaea L.). They belong to four different groups: compounds that included tyrosol or hydroxytyrosol in their molecules, lignans, flavonoids, and phenolic acids. Data of phenolics in the oils showed that the progeny displayed a large degree of variability, widely transgressing the genitor levels. This high variability can be of interest on breeding programs. Thus, multivariate analysis allowed to identify genotypes within the progeny particularly interesting in terms of phenolic composition and deduced organoleptic and nutritional quality. The present study has demonstrated that it is possible to obtain enough degree of variability with a single cross of olive cultivars for compounds related to the nutritional and organoleptic properties of virgin olive oil.

  19. Variability of Virgin Olive Oil Phenolic Compounds in a Segregating Progeny from a Single Cross in Olea europaea L. and Sensory and Nutritional Quality Implications

    PubMed Central

    Pérez, Ana G.; León, Lorenzo; Pascual, Mar; Romero-Segura, Carmen; Sánchez-Ortiz, Araceli; de la Rosa, Raúl; Sanz, Carlos

    2014-01-01

    Virgin olive oil phenolic compounds are responsible for its nutritional and sensory quality. The synthesis of phenolic compounds occurs when enzymes and substrates meet as olive fruit is crushed during the industrial process to obtain the oil. The genetic variability of the major phenolic compounds of virgin olive oil was studied in a progeny of the cross of Picual x Arbequina olive cultivars (Olea europaea L.). They belong to four different groups: compounds that included tyrosol or hydroxytyrosol in their molecules, lignans, flavonoids, and phenolic acids. Data of phenolics in the oils showed that the progeny displayed a large degree of variability, widely transgressing the genitor levels. This high variability can be of interest on breeding programs. Thus, multivariate analysis allowed to identify genotypes within the progeny particularly interesting in terms of phenolic composition and deduced organoleptic and nutritional quality. The present study has demonstrated that it is possible to obtain enough degree of variability with a single cross of olive cultivars for compounds related to the nutritional and organoleptic properties of virgin olive oil. PMID:24651694

  20. Synergetic effect between photocatalytic degradation and adsorption processes on the removal of phenolic compounds from olive mill wastewater.

    PubMed

    Baransi, Katie; Dubowski, Yael; Sabbah, Isam

    2012-03-01

    The photocatalytic degradation of two phenolic compounds, p-coumaric acid and caffeic acid, was performed with a suspended mixture of TiO(2) and powdered activated carbon (PAC) (at pH=3.4 and 8). Adsorption, direct photolysis and photocatalytic degradation were studied under different pH and UV light sources (sunlight vs. 365nm UV lamps). The potential for reusing this catalyst mixture in sequential photocatalytic runs was examined as well. Quantum yields for the direct photolysis of caffeic acid under solar and artificial 365nm light were calculated (for the first time) as 0.005 and 0.011, respectively. A higher removal rate of contaminants by either adsorption or photocatalysis was obtained at a low pH (pH 4). Furthermore, the addition of PAC increased the removal efficiency of the phenolic compounds. Fast removal of the pollutants from the solution over three sequential runs was achieved only when both TiO(2) and PAC were present. This suggests that at medium phenolic concentrations, the presence of PAC as a co-sorbent reduces surface poisoning of the TiO(2) catalyst and hence improves photocatalysis degradation of phenolic pollutants. The adsorption equilibrium of caffeic acid or p-coumaric acid on TiO(2), PAC and the combined mixture of TiO(2) and PAC follows the Langmuir isotherm model. Experiments with PAC TiO(2) mixture and olive mill wastewater (anaerobically treated and diluted by a factor of 10) showed higher removal of polyphenols than of chemical oxygen demand (COD). 87% removal of total polyphenols, compared to 58% of COD, was achieved after 24h of exposure to 365nm irradiation (7.6W/m(2)) in the presence of a suspended mixture of TiO(2) and PAC, indicating "self-selectivity" of polyphenols. PMID:22153960

  1. Synergetic effect between photocatalytic degradation and adsorption processes on the removal of phenolic compounds from olive mill wastewater.

    PubMed

    Baransi, Katie; Dubowski, Yael; Sabbah, Isam

    2012-03-01

    The photocatalytic degradation of two phenolic compounds, p-coumaric acid and caffeic acid, was performed with a suspended mixture of TiO(2) and powdered activated carbon (PAC) (at pH=3.4 and 8). Adsorption, direct photolysis and photocatalytic degradation were studied under different pH and UV light sources (sunlight vs. 365nm UV lamps). The potential for reusing this catalyst mixture in sequential photocatalytic runs was examined as well. Quantum yields for the direct photolysis of caffeic acid under solar and artificial 365nm light were calculated (for the first time) as 0.005 and 0.011, respectively. A higher removal rate of contaminants by either adsorption or photocatalysis was obtained at a low pH (pH 4). Furthermore, the addition of PAC increased the removal efficiency of the phenolic compounds. Fast removal of the pollutants from the solution over three sequential runs was achieved only when both TiO(2) and PAC were present. This suggests that at medium phenolic concentrations, the presence of PAC as a co-sorbent reduces surface poisoning of the TiO(2) catalyst and hence improves photocatalysis degradation of phenolic pollutants. The adsorption equilibrium of caffeic acid or p-coumaric acid on TiO(2), PAC and the combined mixture of TiO(2) and PAC follows the Langmuir isotherm model. Experiments with PAC TiO(2) mixture and olive mill wastewater (anaerobically treated and diluted by a factor of 10) showed higher removal of polyphenols than of chemical oxygen demand (COD). 87% removal of total polyphenols, compared to 58% of COD, was achieved after 24h of exposure to 365nm irradiation (7.6W/m(2)) in the presence of a suspended mixture of TiO(2) and PAC, indicating "self-selectivity" of polyphenols.

  2. The interaction of phenolic acids with Fe(III) in the presence of citrate as studied by isothermal titration calorimetry.

    PubMed

    Yang, Senpei; Bai, Guangling; Chen, Lingli; Shen, Qun; Diao, Xianmin; Zhao, Guanghua

    2014-08-15

    Under physiological conditions, exogenous chelators such as polyphenols might interact with non-protein bound ferric complexes, such as Fe(III)-citrate. Additionally, Fe(III) and citrate are widely distributed in various fruits and vegetables which are also rich in phenolic acids. In this study, we focus on the interaction between phenolic acids (gallic acid, methyl gallate and protocatechuic acid) and Fe(III) in the presence of excessive citrate by isothermal titration calorimetry (ITC) for thermodynamic studies, and stopped-flow absorption spectrometry for fast kinetic studies. Results reveal that all of these three phenolic acids can bind to the Fe(III) with the same stoichiometry (3:1). Moreover, the binding constants of these three compounds with Fe(III) are greatly dependent on ligand structure, and are much higher than that of Fe(III)-citrate. Based on their stoichiometry and superhigh binding constants, it is most likely that these three phenolic acids can displace the citrate to bind with one iron(III) ion to form a stable octahedral geometric structure, albeit at different rates. These findings shed light on the interaction between phenolic acids and Fe(III) in the presence of citrate under either physiological conditions or in a food system.

  3. Effect of Steam Blanching and Drying on Phenolic Compounds of Litchi Pericarp.

    PubMed

    Kessy, Honest N E; Hu, Zhuoyan; Zhao, Lei; Zhou, Molin

    2016-01-01

    The effects of different treatment methods on the stability and antioxidant capacity of the bioactive phenolic compounds of litchi pericarps were investigated. Fresh litchi pericarps were open air-dried, steam-blanched for 3 min in combination with hot air oven drying at 60 and 80 °C, and unblanched pericarps were dried in a hot air oven at 40, 60, 70 and 80 °C until equilibrium weight was reached. The total phenolic compounds, flavonoids, anthocyanins, proanthocyanidins and individual procyanidins, and antioxidant activity were analyzed. The combination of blanching and drying at 60 °C significantly (p < 0.05) improved the release of phenolic compounds, individual procyanidins, and the extracts' antioxidant capacity compared with the unblanched hot air oven-dried and open air-dried pericarps. Drying of fresh unblanched litchi pericarps in either open air or a hot air oven caused significant losses (p < 0.05) in phenolic compounds and individual procyanidins, leading to a reduction in the antioxidant activity. A similar increase, retention or reduction was reflected in flavonoids, proanthocyanidins and anthocyanins because they are sub-groups of phenolic compounds. Ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picryldydrazyl (DPPH) radical-scavenging capacity of the treated pericarps were significantly correlated (r ≥ 0.927, p < 0.01) with the total phenolic compounds. Thus, the combination of steam blanching and drying treatments of fresh litchi pericarps could produce a stable and dry litchi pericarp that maintains phenolic compounds and antioxidant capacity as a raw material for further recovery of the phytochemicals.

  4. Effect of Steam Blanching and Drying on Phenolic Compounds of Litchi Pericarp.

    PubMed

    Kessy, Honest N E; Hu, Zhuoyan; Zhao, Lei; Zhou, Molin

    2016-01-01

    The effects of different treatment methods on the stability and antioxidant capacity of the bioactive phenolic compounds of litchi pericarps were investigated. Fresh litchi pericarps were open air-dried, steam-blanched for 3 min in combination with hot air oven drying at 60 and 80 °C, and unblanched pericarps were dried in a hot air oven at 40, 60, 70 and 80 °C until equilibrium weight was reached. The total phenolic compounds, flavonoids, anthocyanins, proanthocyanidins and individual procyanidins, and antioxidant activity were analyzed. The combination of blanching and drying at 60 °C significantly (p < 0.05) improved the release of phenolic compounds, individual procyanidins, and the extracts' antioxidant capacity compared with the unblanched hot air oven-dried and open air-dried pericarps. Drying of fresh unblanched litchi pericarps in either open air or a hot air oven caused significant losses (p < 0.05) in phenolic compounds and individual procyanidins, leading to a reduction in the antioxidant activity. A similar increase, retention or reduction was reflected in flavonoids, proanthocyanidins and anthocyanins because they are sub-groups of phenolic compounds. Ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picryldydrazyl (DPPH) radical-scavenging capacity of the treated pericarps were significantly correlated (r ≥ 0.927, p < 0.01) with the total phenolic compounds. Thus, the combination of steam blanching and drying treatments of fresh litchi pericarps could produce a stable and dry litchi pericarp that maintains phenolic compounds and antioxidant capacity as a raw material for further recovery of the phytochemicals. PMID:27271581

  5. Nickel-catalyzed cross-coupling of phenols and arylboronic acids through an in situ phenol activation mediated by PyBroP.

    PubMed

    Chen, Guo-Jun; Huang, Jie; Gao, Lian-Xun; Han, Fu-She

    2011-03-28

    A new method for the Suzuki-Miyaura cross-coupling of phenols and arylboronic acids through in situ phenol activation mediated by PyBroP is presented. The reaction proceeds efficiently by using cost-effective, markedly stable [NiCl(2)(dppp)] (dppp=1,3-bis(diphenylphosphino)propane) as the catalyst in only 5 mol % loading, as well as in the absence of extra ligands. The method exhibits broad applicability and high efficiency towards a wide range of both phenols and boronic acids, including activated, nonactivated, deactivated, and heteroaromatic coupling partners. In addition, various functional groups, such as ether, amino, cyano, ester, and ketone groups, are compatible with this transformation. Notably, arylboronic acids containing an unprotected NH(2) group and 2-heterocyclic boronic acids, which are generally problematic for coupling under conventional conditions, are also viable substrates, although moderate yields were obtained for sterically hindered substrates. Consequently, the in situ cross-coupling methodology coupled with the use of an inexpensive and stable nickel catalyst provides a rapid and efficient pathway for the assembly of biaryls and heterobiaryls with structural diversity from readily available phenol compounds.

  6. Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia.

    PubMed

    Sinha, Arun Kumar; Verma, Subash Chandra; Sharma, Upendra Kumar

    2007-01-01

    A simple and fast method was developed using RP-HPLC for separation and quantitative determination of vanillin and related phenolic compounds in ethanolic extract of pods of Vanilla planifolia. Ten phenolic compounds, namely 4-hydroxybenzyl alcohol, vanillyl alcohol, 3,4-dihydroxybenzaldehyde, 4-hydroxybenzoic acid, vanillic acid, 4-hydroxybenzaldehyde, vanillin, p-coumaric acid, ferulic acid, and piperonal were quantitatively determined using ACN, methanol, and 0.2% acetic acid in water as a mobile phase with a gradient elution mode. The method showed good linearity, high precision, and good recovery of compounds of interest. The present method would be useful for analytical research and for routine analysis of vanilla extracts for their quality control.

  7. Simultaneous determination of phenolic acids and flavonoids in Lycium barbarum Linnaeus by HPLC-DAD-ESI-MS.

    PubMed

    Inbaraj, B Stephen; Lu, H; Kao, T H; Chen, B H

    2010-02-01

    A high-performance liquid chromatography-diode array detection-mass spectrometry method with electrospray ionization mode (HPLC-DAD-ESI-MS) was developed for simultaneous determination of phenolic acids and flavonoids in fruits of Lycium barbarum Linnaeus, a widely used traditional Chinese herb possessing vital biological activity. Both phenolic acids and flavonoids were extracted with 50% ethanol and purified using a polymeric solid phase extraction cartridge followed by HPLC-DAD-ESI-MS analysis. By employing a Vydac C18 column, a total of 52 phenolic acids and flavonoids were separated within 70min using a gradient mobile phase of 0.5% (v/v) formic acid in water and acetonitrile-water (94:6, v/v) with flow rate at 1mL/min, column temperature at 30 degrees C and detection wavelength at 280nm. Of 52 compounds, 15 phenolic acids and flavonoids were positively identified based on both absorption and mass spectra, with the remaining 37 tentatively identified by comparison of absorption spectra with reported values in the literature. Internal standards 3-hydroxybenzoic acid and hesperidin were used for quantitation of phenolic acids and flavonoids, respectively. Among the 15 positively identified compounds, quercetin-rhamno-di-hexoside was present in largest mass fraction (438.6microg/g), followed by quercetin-3-O-rutinoside (281.3microg/g), dicaffeoylquinic acid isomers (250.1microg/g), chlorogenic acid (237.0microg/g), quercetin-di-(rhamnohexoside) (117.5microg/g), quercetin-di-(rhamno)-hexoside (116.8mug/g), kaempferol-3-O-rutinoside (97.7microg/g), isorhamnetin-3-O-rutinoside (72.1microg/g), p-coumaric acid (64.0microg/g), caffeic acid (23.7microg/g) and vanillic acid (22.8microg/g). PMID:19819093

  8. The Bark-Beetle-Associated Fungus, Endoconidiophora polonica, Utilizes the Phenolic Defense Compounds of Its Host as a Carbon Source.

    PubMed

    Wadke, Namita; Kandasamy, Dineshkumar; Vogel, Heiko; Lah, Ljerka; Wingfield, Brenda D; Paetz, Christian; Wright, Louwrance P; Gershenzon, Jonathan; Hammerbacher, Almuth

    2016-06-01

    Norway spruce (Picea abies) is periodically attacked by the bark beetle Ips typographus and its fungal associate, Endoconidiophora polonica, whose infection is thought to be required for successful beetle attack. Norway spruce produces terpenoid resins and phenolics in response to fungal and bark beetle invasion. However, how the fungal associate copes with these chemical defenses is still unclear. In this study, we investigated changes in the phenolic content of Norway spruce bark upon E. polonica infection and the biochemical factors mediating these changes. Although genes encoding the rate-limiting enzymes in Norway spruce stilbene and flavonoid biosynthesis were actively transcribed during fungal infection, there was a significant time-dependent decline of the corresponding metabolites in fungal lesions. In vitro feeding experiments with pure phenolics revealed that E. polonica transforms both stilbenes and flavonoids to muconoid-type ring-cleavage products, which are likely the first steps in the degradation of spruce defenses to substrates that can enter the tricarboxylic acid cycle. Four genes were identified in E. polonica that encode catechol dioxygenases carrying out these reactions. These enzymes catalyze the cleavage of phenolic rings with a vicinal dihydroxyl group to muconoid products accepting a wide range of Norway spruce-produced phenolics as substrates. The expression of these genes and E. polonica utilization of the most abundant spruce phenolics as carbon sources both correlated positively with fungal virulence in several strains. Thus, the pathways for the degradation of phenolic compounds in E. polonica, initiated by catechol dioxygenase action, are important to the infection, growth, and survival of this bark beetle-vectored fungus and may play a major role in the ability of I. typographus to colonize spruce trees. PMID:27208235

  9. Gamma irradiation of air-dried olive leaves: Effective decontamination and impact on the antioxidative properties and on phenolic compounds.

    PubMed

    Aouidi, Fathia; Ayari, Samia; Ferhi, Hana; Roussos, Sevastianos; Hamdi, Moktar

    2011-08-01

    Olive leaves are commercialized for their antioxidative value due to their valuable phenolic compounds. The present study aimed to evaluate the effect of gamma irradiation on microbial load, on antioxidative properties and on phenolic compounds of air-dried olive leaves. Irradiation was applied up to 25kGy (5kGy intervals) to powdered and intact samples. Total aerobic bacteria, yeast and mold, and lactic acid bacteria were counted after gamma irradiation. Decontamination was obtained at 20kGy. The radioresistance of microbial population was high with D10 values between 9.74 and 25.12kGy. Besides, gamma irradiation up to 25kGy was found to maintain the antioxidant capacity, molecular mass distribution of polyphenolics, total phenolics, ortho-diphenols, flavonoids, oleuropein, verbascoside and rutin contents. To conclude, the improvement of the microbial quality of air-dried olive leaves, without affecting phenolic composition and antioxidative properties, can be successively achieved by the application of gamma irradiation treatment. PMID:25214102

  10. Structure activity relationship of phenolic acid inhibitors of α-synuclein fibril formation and toxicity

    PubMed Central

    Ardah, Mustafa T.; Paleologou, Katerina E.; Lv, Guohua; Abul Khair, Salema B.; Kazim, Abdulla S.; Minhas, Saeed T.; Al-Tel, Taleb H.; Al-Hayani, Abdulmonem A.; Haque, Mohammed E.; Eliezer, David; El-Agnaf, Omar M. A.

    2014-01-01

    The aggregation of α-synuclein (α-syn) is considered the key pathogenic event in many neurological disorders such as Parkinson's disease (PD), dementia with Lewy bodies and multiple system atrophy, giving rise to a whole category of neurodegenerative diseases known as synucleinopathies. Although the molecular basis of α-syn toxicity has not been precisely elucidated, a great deal of effort has been put into identifying compounds that could inhibit or even reverse the aggregation process. Previous reports indicated that many phenolic compounds are potent inhibitors of α-syn aggregation. The aim of the present study was to assess the anti-aggregating effect of gallic acid (GA) (3,4,5-trihydroxybenzoic acid), a benzoic acid derivative that belongs to a group of phenolic compounds known as phenolic acids. By employing an array of biophysical and biochemical techniques and a cell-viability assay, GA was shown not only to inhibit α-syn fibrillation and toxicity but also to disaggregate preformed α-syn amyloid fibrils. Interestingly, GA was found to bind to soluble, non-toxic oligomers with no β-sheet content, and to stabilize their structure. The binding of GA to the oligomers may represent a potential mechanism of action. Additionally, by using structure activity relationship data obtained from fourteen structurally similar benzoic acid derivatives, it was determined that the inhibition of α-syn fibrillation by GA is related to the number of hydroxyl moieties and their position on the phenyl ring. GA may represent the starting point for designing new molecules that could be used for the treatment of PD and related disorders. PMID:25140150

  11. Cloud-point extraction and reversed-phase high performance liquid chromatography for analysis of phenolic compounds and their antioxidant activity in Thai local wines.

    PubMed

    Vichapong, Jitlada; Santaladchaiyakit, Yanawath; Burakham, Rodjana; Srijaranai, Supalax

    2014-04-01

    A cloud-point extraction (CPE) was developed for the determination of 12 phenolic compounds (i.e. gallic acid, procatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, syringic acid, p-coumaric acid, ferulic acid, guaiacol, p-cresol, o-cresol and 3,5-xylenol) using reversed-phase high performance liquid chromatography (RP-HPLC) with photodiode array (PDA) detection. The optimum CPE conditions were 2.0% (w/v) Triton X-114, 3.0% (w/v) Na2SO4 and 20-min equilibrated at 45 °C. The surfactant-rich phase was then analyzed by HPLC using a Symmetry C18 column, gradient mobile phase of acetonitrile and 1% (v/v) acetic acid, and PDA detection at 280 nm. Under the optimum condition, the target phenolic compounds were separated within 25 min. CPE gave higher enrichment factor up to 15-fold compared to that of direct analysis. The proposed method showed good analytical performances with limits of detection in the range 0.01-0.1 mg L(-1) and precisions with relative standard deviation (RSD) lower than 5% for retention time and 10% for peak area. The method was successfully applied to the analysis of phenolic compounds in Thai local wine samples. Gallic acid, procatechuic acid, and vanillic acid were the highest phenolics found in the studied wines with the contents up to 172.4, 99.1, and 26.6 mg L(-1), respectively. The recovery of the spiked wine samples (0.5, 1.0, and 2.0 mg L(-1)) were obtained in the range of 90.4-110%. High total phenolic content, total flavonoids, and antioxidant activity (DPPH method) in the studied wines were also observed.

  12. Deep eutectic solvents as novel extraction media for phenolic compounds from model oil.

    PubMed

    Gu, Tongnian; Zhang, Mingliang; Tan, Ting; Chen, Jia; Li, Zhan; Zhang, Qinghua; Qiu, Hongdeng

    2014-10-11

    Deep eutectic solvents (DES) as a new kind of green solvent were used for the first time to excellently extract phenolic compounds from model oil. It was also proved that DES could be used to extract other polar compounds from non-polar or weakly-polar solvents by liquid-phase microextraction.

  13. Deep eutectic solvents as novel extraction media for phenolic compounds from model oil.

    PubMed

    Gu, Tongnian; Zhang, Mingliang; Tan, Ting; Chen, Jia; Li, Zhan; Zhang, Qinghua; Qiu, Hongdeng

    2014-10-11

    Deep eutectic solvents (DES) as a new kind of green solvent were used for the first time to excellently extract phenolic compounds from model oil. It was also proved that DES could be used to extract other polar compounds from non-polar or weakly-polar solvents by liquid-phase microextraction. PMID:25144155

  14. Inhibitory Activities of Phenolic Compounds Isolated from Adina rubella Leaves Against 5α-Reductase Associated with Benign Prostatic Hypertrophy.

    PubMed

    Yin, Jun; Heo, Jun Hyeok; Hwang, Yoon Jeong; Le, Thi Tam; Lee, Min Won

    2016-01-01

    Adina rubella Hance (AR), a plant native to Korea, has been used as traditional medicine for dysentery, eczema, intoxication, and external hemorrhages. Previous phytochemical studies of AR have reported several components, including terpenoids, phenolics, and alkaloids. The current study evaluated the anti-oxidative and anti-inflammatory activities and 5α-reductase inhibition of isolated compounds of AR leaves to find a potential therapeutic agent for benign prostatic hypertrophy (BPH). Repeated chromatographic isolation of an 80% acetone extract of AR leaves yielded seven phenolic compounds: caffeic acid (1), chlorogenic acid (2), methyl chlorogenate (3), quercetin-3-rutinoside (4), kaempferol-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (5), hyperoside (6), and grandifloroside (7). Compound 7 is a novel compound in AR. Caffeoyl derivatives 1-3 and 7 showed good anti-oxidative activities. In particular, caffeic acid (1) and grandifloroside (7) showed potent anti-inflammatory activities, and 7 also exhibited potent inhibitory activity against TNF-α and 5α-reductase. Our results show that the extract and grandifloroside (7) from leaves of AR might be developed as a source of potent anti-oxidative and anti-inflammatory agents and therapeutic agent for BPH. PMID:27399661

  15. Evaluation of antioxidant activities of the edible and medicinal Acacia albida organs related to phenolic compounds.

    PubMed

    Karoune, Samira; Falleh, Hanen; Kechebar, Mohamed Seif Allah; Halis, Youcef; Mkadmini, Khaoula; Belhamra, Mohamed; Rahmoune, Chaabane; Ksouri, Riadh

    2015-01-01

    This study compared phenolic contents and antioxidant activity in different organs of Acacia albida (leaves and bark) and focuses on identification of phenolic compounds of leaves by HPLC-DAD. The analysed organs exhibited differences in total polyphenol contents (100 and 59.5 mg GAE g(-1) DW). Phenolic contents of leaves were two times higher than those in bark. Ethanolic extracts exhibited good antioxidant activities with IC50 = 26 μg mL(-1) for DPPH and EC50 = 50 μg mL(-1) for FRAP. Identification by HPLC-DAD revealed the presence of nine phenolic compounds known for their high antioxidant activity. The results suggested that this species can be used as source of natural antioxidants.

  16. In vitro permeation studies of phenolics from horse chestnut seed gels prepared with different polyacrylic acid polymer derivatives.

    PubMed

    Zelbienė, Eglė; Draksiene, Gailute; Savickas, Arunas; Kopustinskiene, Dalia; Masteikova, Ruta; Bernatoniene, Jurga

    2015-06-01

    The aim of this study was to investigate the effects of polyacrylic acid polymers (Ultrez 10, Ultrez 20, Carbopol 980, and Carbopol 940) on the viscosity and the in vitro permeation of phenolic compounds from the gel prepared from natural horse chestnut seed extract. Experiments were performed in the presence and in the absence of peppermint oil (Mentha piperita). Our results showed that peppermint oil decreased the viscosity of the gels and permeation of phenolic compounds from all gel samples. Results show that the highest content of phenolic compounds (1.758 μg cm(-2)) permeated in vitro from gel based on Carbopol Ultrez 20 without peppermint oil added (p<0.05 vs. other tested polymers). PMID:26011934

  17. Investigation of the effects of some drugs and phenolic compounds on human dihydrofolate reductase activity.

    PubMed

    Aslan, Erdem; Adem, Sevki

    2015-03-01

    Dihydrofolate reductase (DHFR) plays a fundamental role in cellular metabolism and cell growth. Inhibition of this enzyme will cause a decrease in the amount of folate that occurs in many metabolic processes, and the deficiency of which may cause various diseases. This study investigated the effects of some drugs and phenolic compounds on DHFR activity in vitro. To determine the inhibitory effect of compounds, enzyme activity was measured with a final concentration of an inhibitor ranging from 10 μM to 51 mM. DHFR was inhibited effectively by naringin, ferulic acid, and levofloxacin with IC50 values under 660 μM. Syringic acid, cefepime, ceftizoxime, cefazolin, ceftriaxone, and ceftazidime exhibited inhibitory effects on the enzyme activity with IC50 values in the range of 3.840-30.224 mM. K(i) constants were calculated using the Cheng-Prusoff equation. K(i) constants calculated in the range of 0.009-2.024 mM with respect to nicotinamide adenine dinucleotide phosphate oxidase (NADPH) and in the range of 0.060-5.830 mM about FH2.

  18. Bioactive compounds and phenolic-linked functionality of powdered tropical fruit residues.

    PubMed

    Correia, Roberta T P; Borges, Kátia C; Medeiros, Maria F; Genovese, Maria I

    2012-12-01

    Tropical fruit residues consisting of seeds, peels and residual pulp generated as by-products of fruit processing industry were investigated for bioactive compounds, the in vitro antioxidant capacity as well as alpha-glucosidase and alpha-amylase inhibitory activities. Cyanidin, quercetin, ellagic acid (EA) and proanthocyanidins were found in acerola, jambolan, pitanga and cajá-umbu residue powders. Acerola powder had the highest phenolic content (8839.33 mg catechin equivalents (CE)/100 g) and also high-ascorbic acid (AA) concentration (2748.03 mg/100 g), followed by jambolan and pitanga. The greatest 1,1-Diphenyl-2-picrylhydrazyl (DPPH) inhibition was observed for jambolan (436.76 mmol Trolox eq/g) followed by pitanga (206.68 mmol Trolox eq/g) and acerola (192.60 mmol Trolox eq/g), while acerola had the highest ferric reducing antioxidant power (FRAP) assay result (7.87 mmol Trolox eq/g). All fruit powders exhibited enzymatic inhibition against alpha-amylase (IC50 ranging from 3.40 to 49.5 mg CE/mL) and alpha-glucosidase (IC50 ranging from 1.15 to 2.37 mg CE/mL). Therefore, acerola, jambolan and pitanga dried residues are promising natural ingredients for food and nutraceutical manufacturers, due to their rich bioactive compound content.

  19. HPLC analysis of phenolics compounds and antioxidant capacity of leaves of Vitex megapotamica (Sprengel) Moldenke.

    PubMed

    de Brum, Thiele Faccim; Zadra, Marina; Piana, Mariana; Boligon, Aline Augusti; Fröhlich, Janaina Kieling; de Freitas, Robson Borba; Stefanello, Sílvio Terra; Froeder, Amanda Luana Forbrig; Belke, Bianca Vargas; Nunes, Letícia Teixeira; da Silva Jesus, Roberta; Machado, Michel Mansur; da Rocha, João Batista Teixeira; Soares, Félix Alexandre Antunes; Athayde, Margareth Linde

    2013-07-16

    Vitex megapotamica (Sprengel) Moldenke belongs to the Verbenaceae family and is popularly known as "tarumã". The antioxidant capacity of fractions and crude extract from the leaves of V. megapotamica were determined in this study through the capacity to remove reactive species and phenolic compounds were quantified in the various fractions. The IC50 (DPPH) ranged from 14.17 ± 0.76 to 37.63 ± 0.98 µg/mL. The ethyl acetate fraction might contain the strongest lipid peroxidation inhibitory compounds with an IC50 of 16.36 ± 5.09 µg/mL, being also the one with the highest content of polyphenols (522.4 ± 1.12 mg/g), flavonoids (220.48 ± 0.30 mg/g) and condensed tannins (3.86 ± 0.53 mg/g). Compounds quantified by HPLC/DAD in the crude extract and fractions were chlorogenic and rosmarinic acids. Higher dosages of the extracts were more effective in reducing levels of plasma protein carbonyls and were also shown to be able to remove reactive species by a 2',7'-dichlorofluorescein diacetate assay, reducing oxidative stress in all tested fractions. Results obtained indicated that V. megapotamica exhibits good potential to prevent diseases caused by the overproduction of free radicals and it might also be used as a potential source of natural antioxidant agents.

  20. Localization and Identification of Phenolic Compounds in Theobroma cacao L. Somatic Embryogenesis

    PubMed Central

    ALEMANNO, L.; RAMOS, T.; GARGADENEC, A.; ANDARY, C.; FERRIERE, N.

    2003-01-01

    Cocoa breeders and growers continue to face the problem of high heterogeneity between individuals derived from one progeny. Vegetative propagation by somatic embryogenesis could be a way to increase genetic gains in the field. Somatic embryogenesis in cocoa is difficult and this species is considered as recalcitrant. This study was conducted to investigate the phenolic composition of cocoa flowers (the explants used to achieve somatic embryogenesis) and how it changes during the process, by means of histochemistry and conventional chemical techniques. In flowers, all parts contained polyphenolics but their locations were specific to the organ considered. After placing floral explants in vitro, the polyphenolic content was qualitatively modified and maintained in the calli throughout the culture process. Among the new polyphenolics, the three most abundant were isolated and characterized by 1H‐ and 13C‐NMR. They were hydroxycinnamic acid amides: N‐trans‐caffeoyl‐l‐DOPA or clovamide, N‐trans‐p‐coumaroyl‐l‐tyrosine or deoxiclovamide, and N‐trans‐caffeoyl‐l‐tyrosine. The same compounds were found also in fresh, unfermented cocoa beans. The synthesis kinetics for these compounds in calli, under different somatic embryogenesis conditions, revealed a higher concentration under non‐embryogenic conditions. Given the antioxidant nature of these compounds, they could reflect the stress status of the tissues. PMID:12933367

  1. Monitoring of environmental phenolic endocrine disrupting compounds in treatment effluents and river waters, Korea.

    PubMed

    Ko, Eun-Joung; Kim, Kyoung-Woong; Kang, Seo-Young; Kim, Sang-Don; Bang, Sun-Baek; Hamm, Se-Yeong; Kim, Dong-Wook

    2007-10-15

    The last two decades have witnessed growing scientific and public concerns over endocrine disrupting compounds (EDCs) that have the potential to alter the normal structure or functions of the endocrine system in wildlife and humans. In this study, the phenolic EDCs such as alkylphenol, chlorinated phenol and bisphenol A were considered. They are commonly found in wastewater discharges and in sewage treatment plant. In order to monitor the levels and seasonal variations of phenolic EDCs in various aquatic environments, a total of 15 water samples from the discharged effluent from sewage and wastewater treatment plants and river water were collected for 3 years. Ten environmental phenolic EDCs were determined by GC-MS and laser-induced fluorescence (LIF). GC-MS analysis revealed that most abundant phenolic EDCs were 4-n-heptylphenol, followed by nonlyphenol and bisphenol A during 2002-2003, while 4-t-butylphenol and 4-t-octylphenol were newly detected in aquatic environments in 2004. The category of phenolic EDCs showed similar fluorescence spectra and nearly equal fluorescence decay time. This makes it hard to distinguish each phenolic EDC from the EDCs mixture by LIF. Therefore, the results obtained from LIF analysis were expressed in terms of the fluorescence intensity of the total phenolic EDCs rather than that of the individual EDC. However, LIF monitoring and GC-MS analysis showed consistent result in that the river water samples had lower phenolic EDCs concentration compared to the effluent sample. This revealed a lower fluorescence intensity and the phenolic EDCs concentration in summer was lower than that in winter. For the validation of LIF monitoring for the phenolic EDCs, the correlation between EDCs concentration acquired from GC-MS and fluorescence intensity from LIF was obtained (R=0.7379). This study supports the feasibility of the application of LIF into EDCs monitoring in aquatic systems. PMID:19073088

  2. Optimization of the Aqueous Extraction of Phenolic Compounds from Olive Leaves

    PubMed Central

    Goldsmith, Chloe D.; Vuong, Quan V.; Stathopoulos, Costas E.; Roach, Paul D.; Scarlett, Christopher J.

    2014-01-01

    Olive leaves are an agricultural waste of the olive-oil industry representing up to 10% of the dry weight arriving at olive mills. Disposal of this waste adds additional expense to farmers. Olive leaves have been shown to have a high concentration of phenolic compounds. In an attempt to utilize this waste product for phenolic compounds, we optimized their extraction using water—a “green” extraction solvent that has not yet been investigated for this purpose. Experiments were carried out according to a Box Behnken design, and the best possible combination of temperature, extraction time and sample-to-solvent ratio for the extraction of phenolic compounds with a high antioxidant activity was obtained using RSM; the optimal conditions for the highest yield of phenolic compounds was 90 °C for 70 min at a sample-to-solvent ratio of 1:100 g/mL; however, at 1:60 g/mL, we retained 80% of the total phenolic compounds and maximized antioxidant capacity. Therefore the sample-to-solvent ratio of 1:60 was chosen as optimal and used for further validation. The validation test fell inside the confidence range indicated by the RSM output; hence, the statistical model was trusted. The proposed method is inexpensive, easily up-scaled to industry and shows potential as an additional source of income for olive growers. PMID:26785235

  3. Effect of salinity stress on phenolic compounds and carotenoids in buckwheat (Fagopyrum esculentum M.) sprout.

    PubMed

    Lim, Jeong-Ho; Park, Kee-Jai; Kim, Bum-Keun; Jeong, Jin-Woong; Kim, Hyun-Jin

    2012-12-01

    The effect of salinity stress on the nutritional quality of buckwheat sprouts cultivated for 1, 3, 5, and 7d was investigated by analysis of the antioxidant activity and levels of phenolic compounds and carotenoids. Treatment with various concentrations of NaCl (10, 50, 100, and 200mM) resulted in an increase in the amount of phenolic compounds and carotenoids in the sprouts compared with the control (0mM). The phenolic contents of sprouts treated with 10, 50, and 100mM after 7d of cultivation were 57%, 121%, and 153%, respectively, higher than that of the control (0mM NaCl). Moreover, the accumulation of phenolic compounds was primarily caused by an increase in the levels of 4 compounds: isoorientin, orientin, rutin, and vitexin. The carotenoid content of sprouts treated with 50 and 100mM NaCl was twice higher than that of the control. In addition, the antioxidant activity of ethanol extracts of the sprouts was increased by NaCl treatment. Although the growth rate of sprouts decreased with >50mM NaCl, these results suggest that treatment of an appropriate concentration of NaCl improves the nutritional quality of sprouts, including the level of phenolic compounds, carotenoids, and antioxidant activity.

  4. An update on dietary phenolic compounds in the prevention and management of rheumatoid arthritis.

    PubMed

    Rosillo, María Angeles; Alarcón-de-la-Lastra, Catalina; Sánchez-Hidalgo, Marina

    2016-07-13

    Certain nutritional components influence the cellular metabolism and interfere in the pathological inflammatory process, so that they may act as a coadjuvant in the treatment of many chronic inflammatory diseases, including rheumatoid arthritis (RA). Particularly, a wide range of evidence has demonstrated the beneficial roles of dietary phenolic compounds in RA because of their ability to modulate pro-oxidant and pro-inflammatory pathways reducing the onset of arthritic disease progression. These natural phenolic compounds can modulate both the action and the production of inflammatory mediators either directly or indirectly by modulating the action of other molecules involved in RA pathology. Subsequently, the purpose of this article is to review the main in vitro and in vivo studies in RA, which have documented interesting insights into the antioxidant, anti-inflammatory, and immunomodulatory properties of dietary phenolic compounds focusing on their molecular action mechanisms involved in RA. The observations reported above are promising and suggest that the dietary phenolic compounds may influence the course of RA, ameliorating the RA symptoms and downregulating the inflammation at the molecular level; however, most of the studies conducted to date have been preclinical. Thus, future studies should therefore focus more on understanding the efficacy of these phenolic compounds in humans and bringing them to the forefront of the treatment of chronic human diseases. PMID:27295367

  5. Phenolics of Arbutus unedo L. (Ericaceae) fruits: identification of anthocyanins and gallic acid derivatives.

    PubMed

    Pawlowska, Agata Maria; De Leo, Marinella; Braca, Alessandra

    2006-12-27

    Arbutus unedo L., the strawberry tree (Ericaceae family), is an evergreen shrub or small tree, typical of the Mediterranean fringe and climate. The aim of the present study was to evaluate the profile of the phenolic constituents of A. unedo fruits. Seven compounds were purified by Sephadex LH-20 column chromatography of the MeOH extract followed by HPLC and were characterized as arbutin, beta-D-glucogalline, gallic acid 4-O-beta-D-glucopyranoside, 3-O-galloylquinic acid, 5-O-galloylquinic acid, 3-O-galloylshikimic acid, and 5-O-galloylshikimic acid, by means of NMR and ESI-MS analyses. Moreover, LC-PDA-MS analysis of the red pigment of A. unedo fruits revealed the presence of three anthocyanins recognized as cyanidin 3-O-beta-D-galactopyranoside, delphinidin 3-O-beta-D-glucopyranoside, and cyanidin 3-O-beta-D-arabinopyranoside. These pigments were also quantified. PMID:17177565

  6. Chemical profile and seasonal variation of phenolic acid content in bastard balm (Melittis melissophyllum L., Lamiaceae).

    PubMed

    Skrzypczak-Pietraszek, Ewa; Pietraszek, Jacek

    2012-07-01

    Melittis melissophyllum L. is an old medicinal plant. Nowadays it is only used in the folk medicine but formerly it has been applied in the official medicine as a natural product described in French Pharmacopoeia. M. melissophyllum herbs used in our studies were collected from two localities in Poland in May and September. Methanolic plant extracts were purified by means of solid-phase extraction and then analysed by HPLC-DAD for their phenolic acid profile. Eleven compounds were identified in all plant samples and quantitatively analysed as: protocatechuic, chlorogenic, p-hydroxybenzoic, vanillic, caffeic, syringic, p-coumaric, ferulic, sinapic, o-coumaric and cinnamic acid. Plant materials contained free and bound phenolic acids. The main compounds were: p-hydroxybenzoic acid (30.21-54.16 mg/100 g dw and 37.04-56.75 mg/100 g dw, free and bound, respectively) and p-coumaric acid (40.48-80.55 mg/100 g dw and 28.09-40.85 mg/100 g dw, free and bound, respectively). The highest amounts of the investigated compounds were found in all samples collected in September, e.g. p-hydroxybenzoic acid (September 51.72-54.16 mg/100 g dw vs. May 30.21-34.07 mg/100 g dw), p-coumaric acid (September 77.14-80.55 mg/100 g dw vs. May 40.48-43.2 5mg/100 g dw). Multivariate statistical and data mining techniques, such as cluster analysis (CA) and principal component analysis (PCA), were used to characterize the sample populations according to the geographical localities, vegetation period and compound form (free or bound). To the best of our knowledge we report for the first time the results of quantitative analysis of M. melissophyllum phenolic acids and seasonal variation of their content. Plant herbs are usually collected at flowering for plant derived medical preparations. Our results show that it is not always the optimal time for the highest contents of active compounds. PMID:22513117

  7. Biodegradation of phenolic compounds by Basidiomycota and its phenol oxidases: A review.

    PubMed

    Martínková, L; Kotik, M; Marková, E; Homolka, L

    2016-04-01

    The phylum Basidiomycota include organisms with enormous bioremediation potential. A variety of processes were proposed at the lab scale for using these fungi and their phenol oxidases in the degradation of phenolics. Here we present a survey of this topic using literature published mostly over the last 10 years. First, the sources of the enzymes are summarized. The laccase and tyrosinase were mainly from Trametes versicolor and Agaricus bisporus, respectively. Recently, however, new promising wild-type producers of the enzymes have emerged and a number of recombinant strains were also constructed, based mainly on yeasts or Aspergillus strains as hosts. The next part of the study summarizes the enzyme and whole-cell applications for the degradation of phenols, polyphenols, cresols, alkylphenols, naphthols, bisphenols and halogenated (bis)phenols in model mixtures or real wastewaters from the food, paper and coal industries, or municipal and hospital sewage. The enzymes were applied as free (crude or purified) enzymes or as enzymes immobilized in various supports or CLEAs, and optionally recycled or used in continuous mode. Alternatively, growing cultures or harvested mycelia were used instead. The products, which were characterized as quinones and their polymers in some cases, could be eliminated by filtration, flocculation or adsorption onto chitosan. The purity of a treated wastewater was monitored using a sensitive aquatic organism. It is concluded that low-cost sources of these enzymes should be searched for and the benefits of enzymatic, biological and physico-chemical methods could be combined to make the processes fit for industrial use. PMID:26874626

  8. Simultaneous extraction and biotransformation process to obtain high bioactivity phenolic compounds from Brazilian citrus residues.

    PubMed

    Madeira, Jose Valdo; Macedo, Gabriela Alves

    2015-01-01

    Recent studies have pointed to a reduction in the incidence of some cancers, diabetes, and neuro-degenerative diseases as a result of human health benefits from flavanones. Currently, flavanones are obtained by chemical synthesis or extraction from plants, and these processes are only produced in the glycosylated form. An interesting environmentally friendly alternative that deserves attention regarding phenolic compound production is the simultaneous extraction and biotransformation of these molecules. Orange juice consumption has become a worldwide dietary habit and Brazil is the largest producer of orange juice in the world. Approximately half of the citrus fruit is discarded after the juice is processed, thus generating large amounts of residues (peel and pectinolytic material). Hence, finding an environmentally clean technique to extract natural products and bioactive compounds from different plant materials has presented a challenging task over the last decades. The aim of this study was to obtain phenolics from Brazilian citrus residues with high bioactivity, using simultaneous extraction (cellulase and pectinase) and biotransformation (tannase) by enzymatic process. The highest hesperetin, naringenin and ellagic acid production in the experiment were 120, 80, and 11,250 µg g(-1), respectively, at 5.0 U mL(-1) of cellulase and 7.0 U mL(-1) of tannase at 40°C and 200 rpm. Also, the development of this process generated an increase of 77% in the total antioxidant capacity. These results suggest that the bioprocess obtained innovative results where the simultaneous enzymatic and biotransformatic extracted flavanones from agro-industrial residues was achieved without the use of organic solvents. The methodology can therefore be considered a green technology.

  9. [Role of NO signal in ABA-induced phenolic acids accumulation in Salvia miltiorrhiza hairy roots].

    PubMed

    Shen, Lihong; Ren, Jiahui; Jin, Wenfang; Wang, Ruijie; Ni, Chunhong; Tong, Mengjiao; Liang, Zongsuo; Yang, Dongfeng

    2016-02-01

    To investigate roles of nitric oxide (NO) signal in accumulations of phenolic acids in abscisic.acid (ABA)-induced Salvia miltiorrhiza hairy roots, S. miltiorrhiza hairy roots were treated with different concentrations of sodium nitroprusside (SNP)-an exogenous NO donor, for 6 days, and contents of phenolic acids in the hairy roots are determined. Then with treatment of ABA and NO scavenger (2-(4-carboxy-2-phenyl)-4,4,5,5-tetramethylimidazoline-1- oxyl-3-oxide, c-PTIO) or NO synthase inhibitor (NG-nitro-L-arginine methyl ester, L-NAME), contents of phenolic acids and expression levels of three key genes involved in phenolic acids biosynthesis were detected. Phenolic acids production in S. miltiorrhiza hairy roots was most significantly improved by 100 µmoL/L SNP. Contents of RA and salvianolic acid B increased by 3 and 4 folds. ABA significantly improved transcript levels of PAL (phenylalanine ammonia lyase), TAT (tyrosine aminotransferase) and RAS (rosmarinic acid synthase), and increased phenolic acids accumulations. However, with treatments of ABA+c-PTIO or ABA+L-NAME, accumulations of phenolic acids and expression levels of the three key genes were significantly inhibited. Both NO and ABA can increase accumulations of phenolic acids in S. miltiorrhiza hairy roots. NO signal probably mediates the ABA-induced phenolic acids production. PMID:27382772

  10. Extraction optimization for antioxidant phenolic compounds in red grape jam using ultrasound with a response surface methodology.

    PubMed

    Morelli, Lucíula Lemos Lima; Prado, Marcelo Alexandre

    2012-11-01

    Optimization of the extraction methodology for antioxidant phenolic compounds in red grape jam was performed with an ultrasound-assisted system. The antioxidant phenolic compounds were extracted and analyzed by determining the total phenolic content (Folin Ciocalteu), as well as by employing free radical DPPH() and the beta-carotene/linoleic acid system. To optimize the parameters of solvent concentration, time and extraction temperature, the experiments were carried out using the central composite rotatable design (CCRD) method. Using response surface methodology (RSM), the best combinations achieved were with 60% ethanol and water for 20min at 50°C. The optimized parameters for this method were compared to an extraction method that has been commonly noted in the literature, which used to be the standard method, and the results were expressed in the milligram equivalent of quercetin per gram of jam (mg E.Q/g Jam). With the new method, the antioxidant potential measured by DPPH(ⁱ) was 70% higher than that obtained with the standard extraction method, and the antioxidant potential measured using the beta-carotene/linoleic acid system was 65% higher. In addition, a significant decrease in the total analysis time was achieved (from 10h to 30min), when compared to the standard method. PMID:22512996

  11. Bioprocess design for the microbial production of natural phenolic compounds by Debaryomyces hansenii.

    PubMed

    Max, Belén; Tugores, Francisco; Cortés-Diéguez, Sandra; Domínguez, José M

    2012-12-01

    Debaryomyces hansenii NRRL Y-7426 metabolised ferulic acid into different phenolic compounds using a factorial design where glucose concentration (in the range of 1-20 g/L), peptone concentration (2-20 g/L) and yeast extract concentration (0.2-10 g/L) were the independent variables. The interrelationship between dependent and operational variables was well fitted (R (2) > 0.95) to models including linear, interaction and quadratic terms. Depending on the glucose and nitrogen concentrations, which redirected the metabolism, the major degradation products were 1,226.2 mg 4-vinyl guaiacol/L after 72 h (molar yield of 86.0 %), 1,077.8 mg vanillic acid/L after 360 h (molar yield of 91.1 %) or 1,682.6 mg acetovanillone/L after 408 h (molar yield of 98.8 %) in fermentations carried out with 2,000 mg ferulic acid/L. Other metabolites such as vanillin, vanillyl alcohol or 4-ethylguaiacol were present in lower amounts. PMID:23076573

  12. Radical scavenging activity and phenolic compounds in persimmon (Diospyros kaki L. cv. Mopan).

    PubMed

    Chen, X N; Fan, J F; Yue, X; Wu, X R; Li, L T

    2008-01-01

    The Mopan persimmon (Diospyros kaki L. cv. Mopan) is the major cultivar of astringent persimmon in northern China. This study investigates the radical scavenging activity against ABTS and DPPH radical, and the content of total and individual phenolics (catechin, epicatechin, epigallocatechin, chlorogenic acid, caffeic acid, and gallic acid) with apple, grape, and tomato as controls. The radical scavenging activities against ABTS and DPPH radicals of the Mopan persimmon are 23.575 and 22.597 microm trolox eq/g f.w., respectively. These findings suggest that the Mopan persimmon's antioxidant activity is significantly (P < 0.05) stronger than that of reference materials. The Mopan persimmon showed the highest content of total phenolics among the 4 materials tested. Significant correlations (R(2)= 0.993, P < 0.05, ABTS radical; R(2)= 0.980, P < 0.05, DPPH radical) are found between the total phenolics and the radical scavenging activities. The total content of these 6 kinds of phenolics (catechin, epicatechin, epigallocatechin, chlorogenic acid, caffeic acid, and gallic acid) is significantly correlated (R(2)= 0.831, P < 0.05, ABTS radical; R(2)= 0.745, P < 0.05, DPPH radical) with the individual radical scavenging activity of the 4 materials, although the total content of the 6 phenolics accounts for no more than 20% of the total phenolics in the Mopan persimmon. Gallic acid exhibits the strongest antioxidant activity in all 6 kinds of phenolics and its content is the largest in the Mopan persimmon, presumably being responsible for its much higher antioxidant activity as compared to apple, grape, and tomato.

  13. Changes in phenolic compounds and their antioxidant capacities in jujube (Ziziphus jujuba Miller) during three edible maturity stages

    Technology Transfer Automated Retrieval System (TEKTRAN)

    This study investigated the changes in total phenolic content (TPC), total flavonoid content (TFC), individual phenolic compound content, DPPH radical scavenging activity and antioxidant capacity measured by FRAP assay of four phenolic fractions (free, esterified, glycosided and insoluble-bound) fro...

  14. Decoction, infusion and hydroalcoholic extract of Origanum vulgare L.: different performances regarding bioactivity and phenolic compounds.

    PubMed

    Martins, Natália; Barros, Lillian; Santos-Buelga, Celestino; Henriques, Mariana; Silva, Sónia; Ferreira, Isabel C F R

    2014-09-01

    Bioactivity of oregano methanolic extracts and essential oils is well known. Nonetheless, reports using aqueous extracts are scarce, mainly decoction or infusion preparations used for therapeutic applications. Herein, the antioxidant and antibacterial activities, and phenolic compounds of the infusion, decoction and hydroalcoholic extract of oregano were evaluated and compared. The antioxidant activity is related with phenolic compounds, mostly flavonoids, since decoction presented the highest concentration of flavonoids and total phenolic compounds, followed by infusion and hydroalcoholic extract. The samples were effective against gram-negative and gram-positive bacteria. It is important to address that the hydroalcoholic extract showed the highest efficacy against Escherichia coli. This study demonstrates that the decoction could be used for antioxidant purposes, while the hydroalcoholic extract could be incorporated in formulations for antimicrobial features. Moreover, the use of infusion/decoction can avoid the toxic effects showed by oregano essential oil, widely reported for its antioxidant and antimicrobial properties. PMID:24731316

  15. [Study of antioxidant activity of phenolic compounds from some species of Georgian flora].

    PubMed

    Alaniia, M; Shalashvili, K; Sagareishvili, T; Kavtaradze, N; Sutiashvili, M

    2013-09-01

    The antioxidant activity of extracts obtained from different parts of Georgian flora species Hamamelis virginiana L., Astragalus caucasicus Pall., Astragalus microcephalus Willd., Vitis vinifera L., Rhododendron ponticum L., Rhododendron Ungernii Trautv., Ginkgo biloba L., Salvia officinalis L., Querqus iberica Stev., Maclura aurantiaca Nutt., Cotinus coggygria Ledeb., Fraxinus ornus L., Urtica dioica L., Rhododendron caucasicum Pall., Pueraria hirsuta Matsum., Geranium pusillum L., Astragalus Tanae Sosn., Pinus silvestris L. has been studied. Comparison with ethylentetraacetate and α-tocopherole revealed high efficacy of all extracts studied. 45 individual phenolic compounds were isolated and described by chemical examination of biologically active objects. Common sage (Salvia officinalis) extract turned out as the most active (200 %). The chemical study revealed the dominant content of condensed tannins and low molecular phenolic compounds, which may be attributed to the high antioxidant activity. Biologically active antiatherosclerotic food additive "Salbin" was developed on the basis of Common sage - Salvia officinalis L. phenolic compounds. PMID:24099817

  16. Ocean acidification increases the accumulation of toxic phenolic compounds across trophic levels

    PubMed Central

    Jin, Peng; Wang, Tifeng; Liu, Nana; Dupont, Sam; Beardall, John; Boyd, Philip W.; Riebesell, Ulf; Gao, Kunshan

    2015-01-01

    Increasing atmospheric CO2 concentrations are causing ocean acidification (OA), altering carbonate chemistry with consequences for marine organisms. Here we show that OA increases by 46–212% the production of phenolic compounds in phytoplankton grown under the elevated CO2 concentrations projected for the end of this century, compared with the ambient CO2 level. At the same time, mitochondrial respiration rate is enhanced under elevated CO2 concentrations by 130–160% in a single species or mixed phytoplankton assemblage. When fed with phytoplankton cells grown under OA, zooplankton assemblages have significantly higher phenolic compound content, by about 28–48%. The functional consequences of the increased accumulation of toxic phenolic compounds in primary and secondary producers have the potential to have profound consequences for marine ecosystem and seafood quality, with the possibility that fishery industries could be influenced as a result of progressive ocean changes. PMID:26503801

  17. Sorghum flour fractions: correlations among polysaccharides, phenolic compounds, antioxidant activity and glycemic index.

    PubMed

    Moraes, Érica Aguiar; Marineli, Rafaela da Silva; Lenquiste, Sabrina Alves; Steel, Caroline Joy; de Menezes, Cícero Beserra; Queiroz, Valéria Aparecida Vieira; Maróstica Júnior, Mário Roberto

    2015-08-01

    Nutrients composition, phenolic compounds, antioxidant activity and estimated glycemic index (EGI) were evaluated in sorghum bran (SB) and decorticated sorghum flour (DSF), obtained by a rice-polisher, as well as whole sorghum flour (WSF). Correlation between EGI and the studied parameters were determined. SB presented the highest protein, lipid, ash, β-glucan, total and insoluble dietary fiber contents; and the lowest non-resistant and total starch contents. The highest carbohydrate and resistant starch contents were in DSF and WSF, respectively. Phenolic compounds and antioxidant activities were concentrated in SB. The EGI values were: DSF 84.5 ± 0.41; WSF 77.2 ± 0.33; and SB 60.3 ± 0.78. Phenolic compounds, specific flavonoids and antioxidant activities, as well as total, insoluble and soluble dietary fiber and β-glucans of sorghum flour samples were all negatively correlated to EGI. RS content was not correlated to EGI.

  18. Ocean acidification increases the accumulation of toxic phenolic compounds across trophic levels.

    PubMed

    Jin, Peng; Wang, Tifeng; Liu, Nana; Dupont, Sam; Beardall, John; Boyd, Philip W; Riebesell, Ulf; Gao, Kunshan

    2015-10-27

    Increasing atmospheric CO2 concentrations are causing ocean acidification (OA), altering carbonate chemistry with consequences for marine organisms. Here we show that OA increases by 46-212% the production of phenolic compounds in phytoplankton grown under the elevated CO2 concentrations projected for the end of this century, compared with the ambient CO2 level. At the same time, mitochondrial respiration rate is enhanced under elevated CO2 concentrations by 130-160% in a single species or mixed phytoplankton assemblage. When fed with phytoplankton cells grown under OA, zooplankton assemblages have significantly higher phenolic compound content, by about 28-48%. The functional consequences of the increased accumulation of toxic phenolic compounds in primary and secondary producers have the potential to have profound consequences for marine ecosystem and seafood quality, with the possibility that fishery industries could be influenced as a result of progressive ocean changes.

  19. Decoction, infusion and hydroalcoholic extract of Origanum vulgare L.: different performances regarding bioactivity and phenolic compounds.

    PubMed

    Martins, Natália; Barros, Lillian; Santos-Buelga, Celestino; Henriques, Mariana; Silva, Sónia; Ferreira, Isabel C F R

    2014-09-01

    Bioactivity of oregano methanolic extracts and essential oils is well known. Nonetheless, reports using aqueous extracts are scarce, mainly decoction or infusion preparations used for therapeutic applications. Herein, the antioxidant and antibacterial activities, and phenolic compounds of the infusion, decoction and hydroalcoholic extract of oregano were evaluated and compared. The antioxidant activity is related with phenolic compounds, mostly flavonoids, since decoction presented the highest concentration of flavonoids and total phenolic compounds, followed by infusion and hydroalcoholic extract. The samples were effective against gram-negative and gram-positive bacteria. It is important to address that the hydroalcoholic extract showed the highest efficacy against Escherichia coli. This study demonstrates that the decoction could be used for antioxidant purposes, while the hydroalcoholic extract could be incorporated in formulations for antimicrobial features. Moreover, the use of infusion/decoction can avoid the toxic effects showed by oregano essential oil, widely reported for its antioxidant and antimicrobial properties.

  20. Ocean acidification increases the accumulation of toxic phenolic compounds across trophic levels

    NASA Astrophysics Data System (ADS)

    Jin, Peng; Wang, Tifeng; Liu, Nana; Dupont, Sam; Beardall, John; Boyd, Philip W.; Riebesell, Ulf; Gao, Kunshan

    2015-10-01

    Increasing atmospheric CO2 concentrations are causing ocean acidification (OA), altering carbonate chemistry with consequences for marine organisms. Here we show that OA increases by 46-212% the production of phenolic compounds in phytoplankton grown under the elevated CO2 concentrations projected for the end of this century, compared with the ambient CO2 level. At the same time, mitochondrial respiration rate is enhanced under elevated CO2 concentrations by 130-160% in a single species or mixed phytoplankton assemblage. When fed with phytoplankton cells grown under OA, zooplankton assemblages have significantly higher phenolic compound content, by about 28-48%. The functional consequences of the increased accumulation of toxic phenolic compounds in primary and secondary producers have the potential to have profound consequences for marine ecosystem and seafood quality, with the possibility that fishery industries could be influenced as a result of progressive ocean changes.

  1. Aquatic Pathways Model to predict the fate of phenolic compounds. Appendixes A through D

    SciTech Connect

    Aaberg, R.L.; Peloquin, R.A.; Strenge, D.L.; Mellinger, P.L.

    1983-04-01

    Organic materials released from energy-related activities could affect human health and the environment. We have developed a model to predict the fate of spills or discharges of pollutants into flowing or static bodies of fresh water. A computer code, Aquatic Pathways Model (APM), was written to implement the model. The APM estimates the concentrations of chemicals in fish tissue, water and sediment, and is therefore useful for assessing exposure to humans through aquatic pathways. The major pathways considered are biodegradation, fish and sediment uptake, photolysis, and evaporation. The model has been implemented with parameters for the distribution of phenols, an important class of compounds found in the water-soluble fractions of coal liquids. The model was developed to estimate the fate of liquids derived from coal. Current modeling efforts show that, in comparison with many pesticides and polyaromatic hydrocarbons (PAH), the lighter phenolics (the cresols) are not persistent in the environment. For the twelve phenolics studied, biodegradation appears to be the major pathway for elimination from aquatic environments. A pond system simulation of a spill of solvent-refined coal (SRC-II) materials indicates that phenol, cresols, and other single cyclic phenolics are degraded to 16 to 25 percent of their original concentrations within 30 hours. Adsorption of these compounds into sediments and accumulation by fish was minor. Results of a simulated spill of a coal liquid (SRC-II) into a pond show that APM predicted the allocation of 12 phenolic components among six compartments at 30 hours after a small spill. The simulation indicated that most of the introduced phenolic compounds were biodegraded. The phenolics remaining in the aquatic system partitioned according to their molecular weight and structure. A substantial amount was predicted to remain in the water, with less than 0.01% distributed in sediment or fish.

  2. Phenolic compo