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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. Quenching of fluorescence of phenolic compounds and modified humic acids by cadmium ions.

    PubMed

    Tchaikovskaya, O N; Nechaev, L V; Yudina, N V; Mal'tseva, E V

    2016-08-01

    The interaction of a number of phenolic compounds, being 'model fragments' of humic acids, with cadmium ions was investigated. The fluorescence quenching method was used to determine the complexation constants of these compounds with cadmium ions. It was established that bonding of phenolic compounds by cadmium ions at рН 7 is weak and reaches a maximum value of 15% for interaction with resorcinol. It was demonstrated that modification of humic acids by the mechanoactivation method increases by three times bonding of cadmium ions, which is caused by strengthening the acid properties of carboxyl and hydroxyl groups at the aromatic ring. Copyright © 2016 John Wiley & Sons, Ltd.

  3. Phenolic compounds extracted by acidic aqueous ethanol from berries and leaves of different berry plants.

    PubMed

    Tian, Ye; Liimatainen, Jaana; Alanne, Aino-Liisa; Lindstedt, Anni; Liu, Pengzhan; Sinkkonen, Jari; Kallio, Heikki; Yang, Baoru

    2017-04-01

    Phenolic compounds of berries and leaves of thirteen various plant species were extracted with aqueous ethanol and analyzed with UPLC-DAD-ESI-MS, HPLC-DAD, and NMR. The total content of phenolics was consistently higher in leaves than in berries (25-7856 vs. 28-711mg/100g fresh weight). Sea buckthorn leaves were richest in phenolic compounds (7856mg/100g f.w.) with ellagitannins as the dominant compound class. Sea buckthorn berries contained mostly isorhamnetin glycosides, whereas quercetin glycosides were typically abundant in most samples investigated. Anthocyanins formed the dominating group of phenolics in most dark-colored berries but phenolic acid derivatives were equally abundant in saskatoon and chokeberry berries. Caffeoylquinic acids constituted 80% of the total phenolic content (1664mg/100g f.w.) in bilberry leaves. B-type procyanidins and caffeoylquinic acids were the major phenolic compounds in hawthorn and rowanberry, respectively. Use of leaves of some species with prunasin, tyramine and β-p-arbutin, may be limited in food applications.

  4. Phenolic compounds in Brassica vegetables.

    PubMed

    Cartea, María Elena; Francisco, Marta; Soengas, Pilar; Velasco, Pablo

    2010-12-30

    Phenolic compounds are a large group of phytochemicals widespread in the plant kingdom. Depending on their structure they can be classified into simple phenols, phenolic acids, hydroxycinnamic acid derivatives and flavonoids. Phenolic compounds have received considerable attention for being potentially protective factors against cancer and heart diseases, in part because of their potent antioxidative properties and their ubiquity in a wide range of commonly consumed foods of plant origin. The Brassicaceae family includes a wide range of horticultural crops, some of them with economic significance and extensively used in the diet throughout the world. The phenolic composition of Brassica vegetables has been recently investigated and, nowadays, the profile of different Brassica species is well established. Here, we review the significance of phenolic compounds as a source of beneficial compounds for human health and the influence of environmental conditions and processing mechanisms on the phenolic composition of Brassica vegetables.

  5. Phenolic acids are in vivo atheroprotective compounds appearing in serum of rats after blueberry consumption

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Blueberries (BB) have recently been shown to have cardio-protective effects and prevention of atherosclerosis in rodent models. However, the bioactive compounds in BB responsible for these effects have not yet been characterized. Seven phenolic acids were identified as metabolites in serum of rats ...

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

    PubMed

    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.

  7. 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

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

    SciTech Connect

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

    2016-07-04

    Lignin is the largest source of renewable material with an aromatic skeleton. However, due to the recalcitrant and heterogeneous nature of the lignin polymer as well as its complex side chain structures, 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) inclduing 4-hydroxy-2-methoxyphenol, p-hydroxybenzoic acid, vanillic acid, syringic acid, and 3,4-dihydroxybenzoic acid. The maximized MPCs 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.

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

    SciTech Connect

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

    2016-07-04

    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.

  10. 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.

  11. 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...

  12. 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.

  13. Weakening of salmonella with selected microbial metabolites of berry-derived phenolic compounds and organic acids.

    PubMed

    Alakomi, Hanna-Leena; Puupponen-Pimiä, Riitta; Aura, Anna-Marja; Helander, Ilkka M; Nohynek, Liisa; Oksman-Caldentey, Kirsi-Marja; Saarela, Maria

    2007-05-16

    Gram-negative bacteria are important food spoilage and pathogenic bacteria. Their unique outer membrane (OM) provides them with a hydrophilic surface structure, which makes them inherently resistant to many antimicrobial agents, thus hindering their control. However, with permeabilizers, compounds that disintegrate and weaken the OM, Gram-negative cells can be sensitized to several external agents. Although antimicrobial activity of plant-derived phenolic compounds has been widely reported, their mechanisms of action have not yet been well demonstrated. The aim of our study was to elucidate the role of selected colonic microbial metabolites of berry-derived phenolic compounds in the weakening of the Gram-negative OM. The effect of the agents on the OM permeability of Salmonella was studied utilizing a fluorescence probe uptake assay, sensitization to hydrophobic antibiotics, and lipopolysaccharide (LPS) release. Our results show that 3,4-dihydroxyphenylacetic acid, 3-hydroxyphenylacetic acid, 3-(3,4-dihydroxyphenyl)propionic acid (3,4-diHPP), 3-(4-hydroxyphenyl)propionic acid, 3-phenylpropionic acid, and 3-(3-hydroxyphenyl)propionic acid efficiently destabilized the OM of Salmonella enterica subsp. enterica serovar Typhimurium and S. enterica subsp. enterica serovar Infantis as indicated by an increase in the uptake of the fluorescent probe 1-N-phenylnaphthylamine (NPN). The OM-destabilizing activity of the compounds was partially abolished by MgCl2 addition, indicating that part of their activity is based on removal of OM-stabilizing divalent cations. Furthermore, 3,4-dihydroxyphenylacetic acid, 3-hydroxyphenylacetic acid, and 3,4-diHPP increased the susceptibility of S. enterica subsp. enterica serovar Typhimurium strains for novobiocin. In addition, organic acids present in berries, such as malic acid, sorbic acid, and benzoic acid, were shown to be efficient permeabilizers of Salmonella as shown by an increase in the NPN uptake assay and by LPS release.

  14. Phenolic Molding Compounds

    NASA Astrophysics Data System (ADS)

    Koizumi, Koji; Charles, Ted; de Keyser, Hendrik

    Phenolic Molding Compounds continue to exhibit well balanced properties such as heat resistance, chemical resistance, dimensional stability, and creep resistance. They are widely applied in electrical, appliance, small engine, commutator, and automotive applications. As the focus of the automotive industry is weight reduction for greater fuel efficiency, phenolic molding compounds become appealing alternatives to metals. Current market volumes and trends, formulation components and its impact on properties, and a review of common manufacturing methods are presented. Molding processes as well as unique advanced techniques such as high temperature molding, live sprue, and injection/compression technique provide additional benefits in improving the performance characterisitics of phenolic molding compounds. Of special interest are descriptions of some of the latest innovations in automotive components, such as the phenolic intake manifold and valve block for dual clutch transmissions. The chapter also characterizes the most recent developments in new materials, including long glass phenolic molding compounds and carbon fiber reinforced phenolic molding compounds exhibiting a 10-20-fold increase in Charpy impact strength when compared to short fiber filled materials. The role of fatigue testing and fatigue fracture behavior presents some insight into long-term reliability and durability of glass-filled phenolic molding compounds. A section on new technology outlines the important factors to consider in modeling phenolic parts by finite element analysis and flow simulation.

  15. Pharmacokinetics of wood creosote: glucuronic acid and sulfate conjugation of phenolic compounds.

    PubMed

    Ogata, N; Matsushima, N; Shibata, T

    1995-09-01

    Wood creosote, principally a mixture of non-, alkyl- and/or alkoxy-substituted phenolic compounds, was orally administered to adult male volunteers to determine its metabolites and pharmacokinetic parameters. After a 133-mg single dose, its major constituents (i.e. phenol 15 mg, guaiacol 32 mg, p-cresol 18 mg and creosol 24 mg) were found in peripheral venous blood and urine, mostly as glucuronic acid and, except for creosol, as sulfate conjugates. Low concentrations of unconjugated phenols were also detected. The metabolites in the serum started to increase 15 min after the dose, and they reached their maximum concentrations 30 min after administration. The maximum concentrations of glucuronides were 0.18 +/- 0.07, 0.91 +/- 0.38, 0.33 +/- 0.18 and 0.47 +/- 0.23 mg/l; those of sulfates were 0.16 +/- 0.06, 0.22 +/- 0.09, 0.17 +/- 0.07 and < 0.04 mg/l for phenol, guaiacol, p-cresol and creosol, respectively. The 24-hour urinary recoveries of the sum of each compound and its metabolites were 75 +/- 35, 45 +/- 36, 103 +/- 51 and 74 +/- 36%, in the above order. The presence of guaiacol glucuronide in blood and urine was directly verified by its isolation and structure analyses.

  16. Separation and determination of organic acids and phenolic compounds in fruit juices and drinks by high-performance liquid chromatography.

    PubMed

    Shui, Guanghou; Leong, Lai Peng

    2002-11-15

    A high-performance liquid chromatographic (HPLC) separation method with photo-diode array detection has been developed for the simultaneous determination of organic acids and phenolic compounds in juices and drinks. The chromatographic analysis of organic acids and phenolic compounds was carried out after their elution with sulphuric acid solution (pH 2.5) and methanol from C18 stationary phase. The mobile phase employed was sulphuric acid solution working at a flow-rate of 0.35 ml min(-1) for the whole run, while methanol was linearly increased to 0.45 ml min(-1) from 15 to 75 min followed by a 5-min isocratic elution. Ten organic acid acids were eluted in 30 min and 21 phenolic compounds, which include phenolic acids and flavonoids, were eluted in the following 50 min. Target compounds were detected at 215 nm. The repeatability (n=3) and between day precision of peak area (n=3) were all within 5.0% RSD. The within-day repeatability (n=3) and between-day precision (n=10) of retention times were within 0.3 and 1.6% relative standard deviation (RSD), respectively. The accuracy of the method was confirmed with an average recovery ranging between 85 and 106%. The method was successfully used to measure a variety of organic acids and phenolic compounds in juices and beverages. This method could also be used to evaluate the authenticity, spoilage or micronutrient contents of juices.

  17. Influence of phenolic compounds on the growth and arginine deiminase system in a wine lactic acid bacterium

    PubMed Central

    Alberto, María R.; de Nadra, María C. Manca; Arena, Mario E.

    2012-01-01

    The influence of seven phenolic compounds, normally present in wine, on the growth and arginine deiminase system (ADI) of Lactobacillus hilgardii X1B, a wine lactic acid bacterium, was established. This system provides energy for bacterial growth and produces citrulline that reacts with ethanol forming the carcinogen ethyl carbamate (EC), found in some wines. The influence of phenolic compounds on bacterial growth was compound dependent. Growth and final pH values increased in presence of arginine. Arginine consumption decreased in presence of protocatechuic and gallic acids (31 and 17%, respectively) and increased in presence of quercetin, rutin, catechin and the caffeic and vanillic phenolic acids (between 10 and 13%, respectively). ADI enzyme activities varied in presence of phenolic compounds. Rutin, quercetin and caffeic and vanillic acids stimulated the enzyme arginine deiminase about 37–40%. Amounts of 200 mg/L gallic and protocatechuic acids inhibited the arginine deiminase enzyme between 53 and 100%, respectively. Ornithine transcarbamylase activity was not modified at all concentrations of phenolic compounds. As gallic and protocatechuic acids inhibited the arginine deiminase enzyme that produces citrulline, precursor of EC, these results are important considering the formation of toxic compounds. PMID:24031815

  18. Influence of phenolic compounds on the growth and arginine deiminase system in a wine lactic acid bacterium.

    PubMed

    Alberto, María R; de Nadra, María C Manca; Arena, Mario E

    2012-01-01

    The influence of seven phenolic compounds, normally present in wine, on the growth and arginine deiminase system (ADI) of Lactobacillus hilgardii X1B, a wine lactic acid bacterium, was established. This system provides energy for bacterial growth and produces citrulline that reacts with ethanol forming the carcinogen ethyl carbamate (EC), found in some wines. The influence of phenolic compounds on bacterial growth was compound dependent. Growth and final pH values increased in presence of arginine. Arginine consumption decreased in presence of protocatechuic and gallic acids (31 and 17%, respectively) and increased in presence of quercetin, rutin, catechin and the caffeic and vanillic phenolic acids (between 10 and 13%, respectively). ADI enzyme activities varied in presence of phenolic compounds. Rutin, quercetin and caffeic and vanillic acids stimulated the enzyme arginine deiminase about 37-40%. Amounts of 200 mg/L gallic and protocatechuic acids inhibited the arginine deiminase enzyme between 53 and 100%, respectively. Ornithine transcarbamylase activity was not modified at all concentrations of phenolic compounds. As gallic and protocatechuic acids inhibited the arginine deiminase enzyme that produces citrulline, precursor of EC, these results are important considering the formation of toxic compounds.

  19. Factors Affecting the Extraction of Intact Ribonucleic Acid from Plant Tissues Containing Interfering Phenolic Compounds

    PubMed Central

    Newbury, H. John; Possingham, John V.

    1977-01-01

    Using conventional methods it is impossible to extract RNA as uncomplexed intact molecules from the leaves of grapevines (Vitis vinifera L.) and from a number of woody perennial species that contain high levels of reactive phenolic compounds. A procedure involving the use of high concentrations of the chaotropic agent sodium perchlorate prevents the binding of phenolic compounds to RNA during extraction. Analyses of the phenolics present in plant tissues used in these experiments indicate that there is a poor correlation between the total phenolic content and the complexing of RNA. However, qualitative analyses suggest that proanthocyanidins are involved in the tanning of RNA during conventional extractions. PMID:16660134

  20. 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.

  1. 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.

  2. Seasonal variations in the concentrations of lipophilic compounds and phenolic acids in the roots of Echinacea purpurea and Echinacea pallida.

    PubMed

    Thomsen, Maria O; Fretté, Xavier C; Christensen, Kathrine B; Christensen, Lars P; Grevsen, Kai

    2012-12-12

    Roots of Echinacea purpurea and Echinacea pallida cultivated for 4 years in a North European climate were analyzed for seasonal variations in the concentrations of lipophilic constituents (alkamides, ketoalkenes, and ketoalkynes) and phenolic acids by harvesting five times during 1 year to establish the optimal time for harvest. A total of 16 alkamides, three ketoalkenes, two ketoalkynes, and four phenolic acids (echinacoside, cichoric acid, caftaric acid, and chlorogenic acid) were identified in aqueous ethanolic (70%) extracts by liquid chromatography-mass spectrometry and quantified by reverse-phase high-performance liquid chromatography. The major alkamides in the roots of E. purpurea were at their lowest concentration in the middle of autumn and early winter, and the total concentration of lipophilic compounds in E. pallida showed the same pattern. Moreover, all of the major phenolic acids in E. purpurea were at their highest concentrations in spring. The optimal harvest time in spring is in contrast to normal growing guidelines; hence, this specific information of seasonal variations in the concentrations of lipophilic and phenolic compounds in E. purpurea and E. pallida is valuable for research, farmers, and producers of medicinal preparations.

  3. Simultaneous determination of phenolic compounds and triterpenic acids in oregano growing wild in Greece by 31P NMR spectroscopy.

    PubMed

    Agiomyrgianaki, Alexia; Dais, Photis

    2012-11-01

    (31)P nuclear magnetic resonance (NMR) spectroscopy was used to detect and quantify simultaneously a large number of phenolic compounds and the two triterpenic acids, ursolic acid and oleanolic acid, extracted from two oregano species Origanum onites and Origanum vulgare ssp. Hirtum using two different organic solvents ethanol and ethyl acetate. This analytical method is based on the derivatization of the hydroxyl and carboxyl groups of these compounds with the phosphorous reagent 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxa phospholane and the identification of the phosphitylated compounds on the basis of the (31)P chemical shifts. Unambiguous assignment of the (31)P NMR chemical shifts of the dihydroxy- and polyhydroxy-phenols in oregano species as well as those of the triterpenic acids was achieved upon comparison with the chemical shifts of model compounds assigned by using two-dimensional NMR techniques. Furthermore, the integration of the appropriate signals of the hydroxyl derivatives in the corresponding (31)P NMR spectra and the use of the phosphitylated cyclohexanol as an internal standard allowed the quantification of these compounds. The validity of this technique for quantitative measurements was thoroughly examined.

  4. Phenolic compounds and fatty acids from acorns (Quercus spp.), the main dietary constituent of free-ranged Iberian pigs.

    PubMed

    Cantos, Emma; Espín, Juan Carlos; López-Bote, Clemente; de la Hoz, Lorenzo; Ordóñez, Juan A; Tomás-Barberán, Francisco A

    2003-10-08

    The aim of the present work was to identify and quantify the phenolic compounds and fatty acids in acorns from Quercus ilex, Quercus rotundifolia, and Quercus suber. The concentration of oleic acid was >63% of total fatty acids in all cases, followed by palmitic and linoleic acids at similar concentrations (12-20%). The concentrations of alpha-tocopherol in Q. rotundifolia, Q. ilex, and Q. suber were 19, 31, and 38 mg/kg of dry matter (DM), respectively, whereas the concentrations of gamma-tocopherol were 113, 66, and 74 mg/kg of DM, respectively. Thirty-two different phenolic compounds were distinguished. All of them were gallic acid derivatives, in the form of either galloyl esters of glucose, combinations of galloyl and hexahydroxydiphenoyl esters of glucose, tergallic O- or C-glucosides, or ellagic acid derivatives. Several tergallic acid C-glucosides were also present in the extracts obtained from Q. suber. Acorns from Q. ilex and Q. rotundifolia showed similar polyphenol patterns mainly with gallic acid-like spectra. Chromatograms of Q. suber showed mainly polyphenols with ellagic acid-like spectra. Valoneic acid dilactone was especially abundant in Q. suber skin. The contribution of skin to the total phenolics of the acorn was relatively small in Q. rotundifolia and Q. ilex but relatively high in Q. suber. Skin extracts from Q. suber, Q. rotundifolia, and Q. ilex showed 1.3, 1.4, and 1.0 antioxidant efficiencies, respectively (compared to that of butylhydroxyanisole). Endosperm extracts showed lower capacity to prevent lipid peroxidation than skin extracts.

  5. 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.

  6. 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.

  7. Myrtus communis berry color morphs: a comparative analysis of essential oils, fatty acids, phenolic compounds, and antioxidant activities.

    PubMed

    Messaoud, Chokri; Boussaid, Mohamed

    2011-02-01

    Extracts of mature dark blue and white berries from two Tunisian Myrtus communis morphs growing at the same site were assessed for their essential-oil and fatty-acid compositions, phenolic contents, and antioxidant activities. The GC and GC/MS analyses of the essential oils allowed the identification of 33 constituents. The oils from the dark blue fruits showed high percentages of α-pinene (11.1%), linalool (11.6%), α-terpineol (15.7%), methyl eugenol (6.2%), and geraniol (3.7%). Myrtenyl acetate (20.3%) was found to be the major compound in the oils from white berries. GC Analysis of the pericarp and seed fatty acids showed that the polyunsaturated fatty acids constituted the major fraction (54.3-78.1%). The highest percentages of linoleic acid (78.0%) and oleic acid (20.0%) were observed in the seeds and the pericarps of the white fruits, respectively. The total phenol, flavonoid, and flavonol contents and the concentration of the eight anthocyanins, identified by HPLC analysis, were significantly higher in the dark blue fruits. All extracts showed a substantial antioxidant activity, assessed by the free radical-scavenging activity and the ferric reducing power, with the dark blue fruit extracts being more effective.

  8. Effect of maceration duration on physicochemical characteristics, organic acid, phenolic compounds and antioxidant activity of red wine from Vitis vinifera L. Karaoglan.

    PubMed

    Kocabey, N; Yilmaztekin, M; Hayaloglu, A A

    2016-09-01

    Effects of different maceration times (5, 10 and 15 days) on composition, phenolic compounds and antioxidant activities of red wines made from the Vitis vinifera L. Karaoglan grown in Malatya were investigated. Maceration duration changed some chemical constituents and color of Karaoglan red wines. A linear relationship was observed between antioxidant activity of wine and maceration duration. Major organic acid was tartaric acid which was at the highest concentration in wine macerated for 10 days. A total of 25 phenolic compounds was determined in wine samples. Within these phenolics; procyanidin B2, trans-caftaric acid, gallic acid, trans-caffeic acid, (+) catechin, (-) epicatechin and quercetin-3-O-glucoside were the most abundant phenolics regardless of maceration duration. In general, extended maceration duration resulted in increase in the concentration of phenolic compounds, reflecting the antioxidant activities of wine. In conclusion, the highest concentrations of total and individual phenolic compounds as well as antioxidant activities were found in wines macerated for 15 days.

  9. 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.

  10. [Phenolic compounds in branches of Tamarix rasissima].

    PubMed

    Li, Juan; Li, Wei-Qi; Zheng, Ping; Wang, Rui; Yu, Jian-Qiang; Yang, Jian-Hong; Yao, Yao

    2014-06-01

    To study the chemical constituents of the branches of Tamarix rasissima, repeated silica gel column chromatography, Sephadex LH-20 chromatography and recrystallization were applied for chemical constituents isolation and purification. Ten phenolic compounds were isolated from the n-BuOH fraction and their structures were elucidated by physical properties and spectra analysis such as UV, ESI-MS and NMR as monodecarboxyellagic acid (1), ellagic acid (2), 3, 3'-di-O-methylellagic acid (3), 3, 3'-di-O-methylellagic acid-4-O-beta-D-glucopyranoside (4), 3, 3'-di-O-methylellagic acid-4'-O-alpha-D-arabinfuranoside (5), ferulic acid (6), isoferulic acid (7), caffeic acid (8), 4-O-acetyl-caffeic acid (9), and 4-methyl-1, 2-benzenediol (10). All compounds except for isoferulic acid were isolated firstly from this plant except for isoferulic acid, and compounds 5, 9 and 10 were obtained from Tamarix genus for the first time.

  11. 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.

  12. Fatty Acids Profile, Phenolic Compounds and Antioxidant Capacity in Elicited Callus of Thevetia peruviana (Pers.) K. Schum.

    PubMed

    Rincón-Pérez, Jack; Rodríguez-Hernández, Ludwi; Ruíz-Valdiviezo, Víctor Manuel; Abud-Archila, Miguel; Luján-Hidalgo, María Celina; Ruiz-Lau, Nancy; González-Mendoza, Daniel; Gutiérrez-Miceli, Federico Antonio

    2016-01-01

    The aim of this study was analyze the effect of jasmonic acid (JA) and abscisic acid (ABA) as elicitors on fatty acids profile (FAP), phenolic compounds (PC) and antioxidant capacity (AC) in callus of Thevetia peruviana. Schenk & Hildebrandt (SH) medium, supplemented with 2 mg/L 2, 4-dichlorophenoxyacetic (2, 4-D) and 0.5 mg/L kinetin (KIN) was used for callus induction. The effect of JA (50, 75 and 100 μM) and ABA (10, 55 and 100 μM) on FAP, PC and AC were analyzed using a response surface design. A maximum of 2.8 mg/g of TPC was obtained with 100 plus 10 µM JA and ABA, respectively, whereas AC maximum (2.17 μg/mL) was obtained with 75 plus 100 µM JA and ABA, respectively. The FAP was affected for JA but not for ABA. JA increased cis-9, cis-12-octadecadienoic acid and decreased dodecanoic acid. Eight fatty acids were identified by GC-MS analysis and cis-9-octadecenoic acid (18:1) was the principal fatty acid reaching 76 % in treatment with 50 μM JA plus 55 μM ABA. In conclusion, JA may be used in T. peruviana callus culture for obtain oil with different fatty acids profile.

  13. Enumeration of human colonic bacteria producing phenolic and indolic compounds: effects of pH, carbohydrate availability and retention time on dissimilatory aromatic amino acid metabolism.

    PubMed

    Smith, E A; Macfarlane, G T

    1996-09-01

    Concentrations of phenolic compounds in human gut contents were more than fourfold higher in the distal colon (6.2 mmol kg-1) compared to the proximal bowel (1.4 mmol kg-1). Tryptophan metabolites were never found in more than trace amounts in large intestinal contents and phenol substituted fatty acids were the major products of aromatic amino acid fermentation that accumulated in the proximal colon, whereas phenol and p-cresol were more important in the distal gut, accounting for 70% of all products of dissimilatory aromatic amino acid metabolism. In vitro incubations of colonic material showed that phenol was produced most rapidly (1.0 mumol g-1 h-1), whereas indole was formed comparatively slowly (0.06 mumol g-1 h-1). Most probable number (MPN) estimations demonstrated that large populations of phenol and indole producing bacteria occur in the large intestine (range log10 9.8-11.5 (g dry wt faeces)-1, mean 10.6, N = 7). With respect to phenolic compounds, phenylacetate and phenylpropionate producers predominated, while indoleacetate-forming bacteria were the major tryptophan-utilizing organisms. Quantitation of products of dissimilatory aromatic amino acid metabolism in MPN tubes showed that phenol and phenylpropionate mainly accumulated at low sample dilutions, whereas phenylacetate, p-cresol, indoleacetate and indolepropionate were formed in greatest amounts at high sample dilutions. The significance of pH and carbohydrate availability with respect to aromatic amino acid metabolism was shown in batch culture fermentation studies, where net production of phenolic compounds by mixed populations of intestinal bacteria was reduced by approximately 33% during growth at pH 5.5 compared to pH 6.8, and by 60% in the presence of a fermentable carbohydrate. Experiments with 16 species of intestinal bacteria belonging to six different genera showed that environmental factors such as low pH and high carbohydrate availability markedly reduced dissimilatory aromatic amino

  14. Food phenolics and lactic acid bacteria.

    PubMed

    Rodríguez, Héctor; Curiel, José Antonio; Landete, José María; de las Rivas, Blanca; López de Felipe, Félix; Gómez-Cordovés, Carmen; Mancheño, José Miguel; Muñoz, Rosario

    2009-06-30

    Phenolic compounds are important constituents of food products of plant origin. These compounds are directly related to sensory characteristics of foods such as flavour, astringency, and colour. In addition, the presence of phenolic compounds on the diet is beneficial to health due to their chemopreventive activities against carcinogenesis and mutagenesis, mainly due to their antioxidant activities. Lactic acid bacteria (LAB) are autochthonous microbiota of raw vegetables. To get desirable properties on fermented plant-derived food products, LAB has to be adapted to the characteristics of the plant raw materials where phenolic compounds are abundant. Lactobacillus plantarum is the commercial starter most frequently used in the fermentation of food products of plant origin. However, scarce information is still available on the influence of phenolic compounds on the growth and viability of L. plantarum and other LAB species. Moreover, metabolic pathways of biosynthesis or degradation of phenolic compounds in LAB have not been completely described. Results obtained in L. plantarum showed that L. plantarum was able to degrade some food phenolic compounds giving compounds influencing food aroma as well as compounds presenting increased antioxidant activity. Recently, several L. plantarum proteins involved in the metabolism of phenolic compounds have been genetically and biochemically characterized. The aim of this review is to give a complete and updated overview of the current knowledge among LAB and food phenolics interaction, which could facilitate the possible application of selected bacteria or their enzymes in the elaboration of food products with improved characteristics.

  15. 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...

  16. Phenolic compounds in Rosaceae fruits from Ecuador.

    PubMed

    Vasco, Catalina; Riihinen, Kaisu; Ruales, Jenny; Kamal-Eldin, Afaf

    2009-02-25

    RP-HPLC-DAD was used to study the content of phenolic compounds in four Ecuadorian fruits (strawberry, Andean blackberry, plum, and capuli cherry). Compounds were identified using spectral characteristics of representative standards and reference samples. Further, LC-MS with MS/MS was used to confirm molecular assignments in previously unstudied capuli cherry. Gallic acid was detected in Andean blackberry, and galloyl esters were detected in strawberries. Both these berries contained ellagic acid derivatives as major compounds, followed by anthocyanins, cyanidin, and pelargonidin glycosides. Plums and capuli cherry showed similar profiles of phenolic compounds, with chlorogenic and neochlorogenic acids being the most important hydroxycinnamates. (-)-Epicatechin was found in high amounts in Andean blackberry, plums, and capuli cherry, while (+)-catechin was only found in capuli cherry. Proanthocyanidins were major compounds in all fruits, and all contained considerable amounts of quercetin derivatives and smaller amounts of kaempferol derivatives. LC-MS analysis of capuli cherry revealed dimeric and trimeric procyanidins, quercetin and kaempferol hexosides and pentosides, and a kaempferol-O,C-dipentoside.

  17. 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.

  18. Stimulation of Cellulases by Small Phenolic Compounds in Pretreated Stover.

    PubMed

    Zhao, Junying; Chen, Hongzhang

    2014-03-27

    The effect of small phenolic compounds in pretreated stover on celluase activity is crucial but has not yet been fully elucidated. This work investigated the effects of both phenolic acid and phenolic aldehyde on cellulase activity. The model substances of small phenolic compounds identified in steam exploded corn stover were used to examine their individual effects on cellulase activity. It was found that phenolic aldehyde significantly inhibited cellulase activity at 0.05-8 g/L. However, phenolic acids might have a concentration-dependent effect on cellulase activity: significant inhibition at 0.05 g/L and slight stimulation at 2-4 g/L. Small phenolic compounds mixture might also have a concentration-dependent effect on cellulase activity: significant stimulation at 2-8 g/L and slight inhibition at 0.05-1 g/L. The small phenolic compounds in pretreated stover were proven to be able to significantly stimulate enzymatic hydrolysis of stover. On the basis of these results, it is proposed that the concentration-dependent effects of small phenolic compounds on cellulase activity should be considered while removing them after pretreatment.

  19. The influence of interactions among phenolic compounds on the antiradical activity of chokeberries (Aronia melanocarpa).

    PubMed

    Jakobek, Lidija; Seruga, Marijan; Krivak, Petra

    2011-06-01

    In the present work, interactions between phenolic compounds from chokeberries and their influence on the antiradical activity was studied. Three fractions were isolated from chokeberries containing different classes of phenolic compounds. The first fraction contained a major part of phenolic acids and flavonols, the second anthocyanins, and the third insoluble phenols and proanthocyanidins. The phenolic compound content was determined using high-performance liquid chromatography, and the antiradical activity using the DPPH test. In order to evaluate the effects of interactions between phenolic compounds on the antiradical activity, the antiradical activity of individual phenolic fractions was compared with that obtained by mixing phenolic fractions. Phenolic mixtures showed the decrease in the antiradical activity in comparison with the individual phenolic fractions. These results suggest the existence of complex interactions among phenolic compounds that caused the decrease of the antiradical activity. Interactions among chokeberry phenols promoted a negative synergism.

  20. 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

    2016-07-22

    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.

  1. Distribution, antioxidant and characterisation of phenolic compounds in soybeans, flaxseed and olives.

    PubMed

    Alu'datt, Muhammad H; Rababah, Taha; Ereifej, Khalil; Alli, Inteaz

    2013-08-15

    The distribution of free and bound phenolic compounds present in soybean, flaxseed and olive were investigated. The phenolic compounds were fractionated on the basis on their solubility characteristics in water, alcohol, dilute base and dilute acid. Reversed phase high pressure liquid chromatography (RP-HPLC) and mass spectrometry (MS) were used for identification of individual components of phenolic compounds. Antioxidant activity (AA%) of free and bound phenolic compounds was measured using the linoleic acid/β-carotene assay. The water-soluble phenolic compound fractions represented 68-81%, 50-72% and 46-56% of the total phenolic compounds measured in full-fat soybean, olive and flaxseed, respectively. Methanolic extraction of free phenolic compounds without heat, solubilised 21-56%, 42-62% and 34-51% of the total phenolic compounds measured in soybean, olive and flaxseed, respectively; methanol extraction of free phenolic compounds with heat solubilised a further 24-34%, 31-37% and 36-37% of phenolic compounds from soybean, olive and flaxseed, respectively. Further dilute alkali and dilute acid solubilised the remaining 10-40%, 1-21% and 12-29% of the total phenolic compounds from soybean, olive and flaxseed, respectively. Results indicated that the full-fat meals of soybean, flaxseed and olive showed higher antioxidant activity compared to defatted meals. RP-HPLC and LC-MS/MS profil1 for soybean, flaxseed and olive indicate two classes of phenolic compounds designated as free and bound phenolic compounds.

  2. Contribution of phenolic compounds to food flavors: Strecker-type degradation of amines and amino acids produced by o- and p-diphenols.

    PubMed

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

    2015-01-14

    The ability of 20 phenolic derivatives to produce the Strecker-type degradation of phenylalanine and phenylglycine methyl ester was studied to investigate both the direct degradation of amino acids and amines by phenolic compounds in the absence of added oxidants and the effect of the number and positions of hydroxyl groups in the aromatic ring of the phenolic compound in relation to its ability to produce carbonyl derivatives from amino compounds. The obtained results showed that polyphenols can produce the Strecker degradation of amino acids and amines in the absence of added oxidants. The only requisite for producing the reaction is the presence of two hydroxyl groups in ortho or para positions. However, the presence of two hydroxyl groups in meta position in an additional aromatic ring can inhibit the Strecker-degrading ability of the hydroxyl groups in ortho or para positions. A reaction pathway that explains all of these findings is proposed. In addition, the effect of reaction conditions on the obtained reaction yields was studied. Activation energies (Ea) for phenylacetaldehyde formation from phenylalanine in the presence of hydroquinone, 1,2,4-trihydroxybenzene, and benzoquinone were 32.9, 31.5, and 28.8 kJ/mol, respectively.

  3. Fatty Acid and Phenolic Compound Concentrations in Eight Different Monovarietal Virgin Olive Oils from Extremadura and the Relationship with Oxidative Stability

    PubMed Central

    Montaño, Alfonso; Hernández, Marcos; Garrido, Inmaculada; Llerena, José Luís; Espinosa, Francisco

    2016-01-01

    Olive oils have been shown to be more resistant to oxidation than other vegetable fats, mainly due to their fatty acid (FA) profile which is rich in oleic acid and to their high content of antioxidants, principally phenols and tocopherols. This has situated virgin olive oils (VOOs) among the fats of high nutritional quality. However, it is important to stress that the oil’s commercial category (olive oil, virgin olive oil, extra-virgin olive oil), the variety of the source plant, and the extraction-conservation systems all decisively influence the concentration of these antioxidants and the oil’s shelf-life. The present work studied the fatty acid (FA) and phenolic composition and the oxidative stability (OS) of eight olive varieties grown in Extremadura (Arbequina, Cornicabra, Manzanilla Cacereña, Manzanilla de Sevilla, Morisca, Pico Limón, Picual, and Verdial de Badajoz), with the olives being harvested at different locations and dates. The Cornicabra, Picual, and Manzanilla Cacereña VOOs were found to have high oleic acid contents (>77.0%), while the VOOs of Morisca and Verdial de Badajoz had high linoleic acid contents (>14.5%). Regarding the phenol content, high values were found in the Cornicabra (633 mg·kg−1) and Morisca (550 mg·kg−1) VOOs, and low values in Arbequina (200 mg·kg−1). The OS was found to depend upon both the variety and the date of harvesting. It was higher in the Cornicabra and Picual oils (>55 h), and lower in those of Verdial de Badajoz (26.3 h), Arbequina (29.8 h), and Morisca (31.5 h). In relating phenols and FAs with the OS, it was observed that, while the latter, particularly the linoleic content (R = −0.710, p < 0.001, n = 135), constitute the most influential factors, the phenolic compounds, especially o-diphenols, are equally influential when the oils’ linoleic content is ≥12.5% (R = 0.674, p < 0.001, n = 47). The results show that VOOs’ resistance to oxidation depends not only on the FA or phenolic profile

  4. Fatty Acid and Phenolic Compound Concentrations in Eight Different Monovarietal Virgin Olive Oils from Extremadura and the Relationship with Oxidative Stability.

    PubMed

    Montaño, Alfonso; Hernández, Marcos; Garrido, Inmaculada; Llerena, José Luís; Espinosa, Francisco

    2016-11-23

    Olive oils have been shown to be more resistant to oxidation than other vegetable fats, mainly due to their fatty acid (FA) profile which is rich in oleic acid and to their high content of antioxidants, principally phenols and tocopherols. This has situated virgin olive oils (VOOs) among the fats of high nutritional quality. However, it is important to stress that the oil's commercial category (olive oil, virgin olive oil, extra-virgin olive oil), the variety of the source plant, and the extraction-conservation systems all decisively influence the concentration of these antioxidants and the oil's shelf-life. The present work studied the fatty acid (FA) and phenolic composition and the oxidative stability (OS) of eight olive varieties grown in Extremadura (Arbequina, Cornicabra, Manzanilla Cacereña, Manzanilla de Sevilla, Morisca, Pico Limón, Picual, and Verdial de Badajoz), with the olives being harvested at different locations and dates. The Cornicabra, Picual, and Manzanilla Cacereña VOOs were found to have high oleic acid contents (>77.0%), while the VOOs of Morisca and Verdial de Badajoz had high linoleic acid contents (>14.5%). Regarding the phenol content, high values were found in the Cornicabra (633 mg·kg(-1)) and Morisca (550 mg·kg(-1)) VOOs, and low values in Arbequina (200 mg·kg(-1)). The OS was found to depend upon both the variety and the date of harvesting. It was higher in the Cornicabra and Picual oils (>55 h), and lower in those of Verdial de Badajoz (26.3 h), Arbequina (29.8 h), and Morisca (31.5 h). In relating phenols and FAs with the OS, it was observed that, while the latter, particularly the linoleic content (R = -0.710, p < 0.001, n = 135), constitute the most influential factors, the phenolic compounds, especially o-diphenols, are equally influential when the oils' linoleic content is ≥12.5% (R = 0.674, p < 0.001, n = 47). The results show that VOOs' resistance to oxidation depends not only on the FA or phenolic profile, but also on

  5. 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.

  6. 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.

  7. 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.

  8. Extraction of phenolic compounds from soils

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Understanding the composition and amount of phenolic inputs from plants is important for studies of soil organic matter formation and nutrient cycling. However, some phenolic compounds, including tannins, can sorb or complex with the soil making them difficult to extract. We extracted soils with a...

  9. Phenolic compounds in Rosaceae fruit and nut crops.

    PubMed

    Ogah, Onwuchekwa; Watkins, Carolyn S; Ubi, Benjamin Ewa; Oraguzie, Nnadozie C

    2014-10-01

    The demand for new fruit cultivars with high levels of phytochemicals, in particular phenolic compounds, has received increasing attention from biochemists, pharmaceutical companies, plant breeders, and the general public due to their health benefits. This review focuses on the economically important Rosaceae, which contains varying proportions and concentrations of these compounds. The paper discusses the common phenolics in the Rosaceae including phenolic acids, flavonols, flavanols, anthocyanins, and dihydrochalcones. The nonextractable phenolics are also presented but not discussed in detail. The metabolism and bioavailability of phenolics, as well as human and environmental factors that affect their concentration and composition, are highlighted. Furthermore, the paper presents different approaches for biofortification and posits that breeding may be the most viable and sustainable option as it improves other fruit quality traits simultaneously and increases confidence in adoption of new cultivars with enhanced consumer appeal.

  10. 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

  11. 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.

  12. 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

  13. Antibacterial activity of phenolic compounds against the phytopathogen Xylella fastidiosa.

    PubMed

    Maddox, Christina E; Laur, Lisa M; Tian, Li

    2010-01-01

    Xylella fastidiosa is a pathogenic bacterium that causes diseases in many crop species, which leads to considerable economic loss. Phenolic compounds (a group of secondary metabolites) are widely distributed in plants and have shown to possess antimicrobial properties. The anti-Xylella activity of 12 phenolic compounds, representing phenolic acid, coumarin, stilbene and flavonoid, was evaluated using an in vitro agar dilution assay. Overall, these phenolic compounds were effective in inhibiting X. fastidiosa growth, as indicated by low minimum inhibitory concentrations (MICs). In addition, phenolic compounds with different structural features exhibited different anti-Xylella capacities. Particularly, catechol, caffeic acid and resveratrol showed strong anti-Xylella activities. Differential response to phenolic compounds was observed among X. fastidiosa strains isolated from grape and almond. Elucidation of secondary metabolite-based host resistance to X. fastidiosa will have broad implication in combating X. fastidiosa-caused plant diseases. It will facilitate future production of plants with improved disease resistance properties through genetic engineering or traditional breeding approaches and will significantly improve crop yield.

  14. Process for producing phenolic compounds from lignins

    SciTech Connect

    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.

  15. 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.

  16. 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.

  17. Analysis of nonextractable phenolic compounds in foods: the current state of the art.

    PubMed

    Pérez-Jiménez, Jara; Torres, Josep Lluís

    2011-12-28

    More than 500 phenolic compounds have been reported as present in foodstuffs, and their intake has been related to the prevention of several chronic diseases. Most of the literature on phenolic compounds focuses on those present in the supernatant of aqueous-organic extractions: extractable phenolics. Nevertheless, significant amounts of phenolic compounds remain in the solid residues after such extractions. These nonextractable phenolics are mostly proanthocyanidins, phenolic acids, and hydrolyzable tannins that are closely associated with the food matrix. Studies of this fraction of dietary phenolic compounds are scarce, and the few there are usually refer to particular types of phenolics rather than to the fraction as a whole. The present review reports the state-of-the-art methods that currently exist for analyzing nonextractable phenolic compounds in foods.

  18. 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.

  19. Extraction and isolation of phenolic compounds.

    PubMed

    Santos-Buelga, Celestino; Gonzalez-Manzano, Susana; Dueñas, Montserrat; Gonzalez-Paramas, Ana M

    2012-01-01

    Phenolic compounds constitute a major class of plant secondary metabolites that are widely distributed in the plant kingdom and show a large structural diversity. These compounds occur as aglycones or glycosides, as monomers or constituting highly polymerized structures, or as free or matrix-bound compounds. Furthermore, they are not uniformly distributed in the plant and their stability varies significantly. This greatly complicates their extraction and isolation processes, which means that a single standardized procedure cannot be recommended for all phenolics and/or plant materials; procedures have to be optimized depending on the nature of the sample and the target analytes, and also on the object of the study. In this chapter, the main techniques for sample preparation, and extraction and isolation of phenolic compounds have been reviewed-from classical solvent extraction procedures to more modern approaches, such as the use of molecularly imprinted polymers or counter-current chromatography.

  20. Toxicity of phenolic compounds to sediment bacteria

    SciTech Connect

    Dean-Ross, D.; Rahimi, M.

    1995-08-01

    Biodegradation of organic compounds plays an important role in remediation of polluted environments. Several factors influence the rate and extent of biodegradation: number of degrading organisms, adequate supply of nutrients, adequate availability of a suitable electron acceptor. One important factor is the toxicity of the organic chemical itself. Very often chemicals may be susceptible to biodegradation at low concentrations, yet may be toxic to the degrading population at higher concentrations, thus inhibiting their own biodegradation. Phenolic compounds are known to exhibit toxicity to bacteria. Under batch conditions, a strain of Pseudomonas could degrade 0.1% phenol in approximately 48 hr, while taking over 130 hr to degrade 0.15% phenol. A concentration of 0.2% phenol was inhibitory to the cells, killing 50% of the inoculum within 10 d. Activated sludge bacteria maintained in pulse fed batch reactors were inhibited by concentrations of phenol in excess of 50 mg/L. Biodegradation of 4-chlorophenol by Alcaligenes sp. A 7-2 showed a similar concentration effect, being inhibited at concentrations above 160 mg/L in fed-batch culture. The present report is part of an investigation on the biodegradation of phenol in contaminated soils and sediments in northwestern Indiana. Phenol has been found in groundwater aquifers which drain into the Grand Calumet watershed, and in groundwater contaminated by a Superfund site. Data on phenol toxicity were needed in order to assess the potential for in situ biodegradation of phenol and related compounds in sediments of the Grand Calumet River. 10 refs., 4 figs.

  1. Analysis of phenolic compounds for poultry feeds

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phenolic compounds have generated significant interest recently as feed additives that can impart bioactive characteristics such as anti-oxidant, anti-microbial, and anti-fungal properties to a feed formulation [1-2]. Such natural compounds may offer some preventive benefit to the routine administra...

  2. Three new phenolic compounds from Dalbergia odorifera.

    PubMed

    Wang, Hao; Dong, Wen-Hua; Zuo, Wen-Jian; Wang, Hui; Zhong, Hui-Min; Mei, Wen-Li; Dai, Hao-Fu

    2014-12-01

    Three new phenolic compounds (1-3) were isolated from the heartwood of Dalbergia odorifera T. Chen. (Leguminosae). Their structures were established based on spectroscopic methods including 1D and 2D NMR (HSQC, COSY, HMBC and ROESY). Compound 2 exhibited cytotoxicity against BEL-7402 tumor cell lines.

  3. Simultaneous Determination of Eight Phenolic Acids, Five Saponins and Four Tanshinones for Quality Control of Compound Preparations Containing Danshen-Sanqi Herb-pair by HPLC-DAD

    PubMed Central

    Yao, Hong; Huang, Xiaomei; Li, Shaoguang; Wu, Youjia; Lin, Xinhua; Shi, Peiying

    2017-01-01

    Background: The herb-pair, Salviaemiltiorrhizae (Danshen, DS) and Panaxnotoginseng (Sanqi,SQ), often occurs in traditional Chinese medicine prescriptions used for the treatment of cardiovascular diseases in clinics in Asian areas. Many commercial preparations containing the DS-SQ herb-pair were produced by various manufactures with the different production process. The raw materials were from different sources, which raised a challenge to control the quality of the herb-pair medicines. Objective: In this paper, a high-performance liquid chromatography (HPLC) method was developed to simultaneously determine seventeen bioactive components, including 8 phenolic acids, 4 tanshinones, and 5 saponins, for quality control of compound preparations containing DS-SQ herb-pair. The chromatographic separation was studied on an Ultimate™ XB-C18 column (150 mm × 4.6 mmi.d., 3.5 μm) with a mobile phase composed of 0.5% aqueous acetic acid and acetonitrile using a gradient elution in 70 min. Results: The optimum detection wavelength was set at 288 nm for phenolic acids and tanshinones, and 203 nm for saponins. The method was validated sufficiently by examining the precision, recoveries, linearity, range, LOD and LOQ, and was successfully applied to quantify the seventeen compounds in five commercial preparations containing DS-SQ herb-pair. Conclusions: It is the first time to report the rapid and simultaneous analysis of the seventeen compounds with the base-line separation of peaks for ginsenoside Rg1 and Re in 70 min by routine HPLC. This HPLC method could be considered as good quality criteria to control the quality of preparations containing DS-SQ herb-pair. SUMMARY An HPLC method was originally developed to simultaneously quantify 8 phenolic acids, 4 tanshinones and 5 saponins in DS-SQ herb-pair preparations.The rapid and simultaneous analysis of the 17 compounds with the base-line separation of peaks for ginsenoside Rg1 and Re within 70 min was achieved for the first

  4. 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.

  5. Natural phenolic compounds from medicinal herbs and dietary plants: potential use for cancer prevention.

    PubMed

    Huang, Wu-Yang; Cai, Yi-Zhong; Zhang, Yanbo

    2010-01-01

    Natural phenolic compounds play an important role in cancer prevention and treatment. Phenolic compounds from medicinal herbs and dietary plants include phenolic acids, flavonoids, tannins, stilbenes, curcuminoids, coumarins, lignans, quinones, and others. Various bioactivities of phenolic compounds are responsible for their chemopreventive properties (e.g., antioxidant, anticarcinogenic, or antimutagenic and anti-inflammatory effects) and also contribute to their inducing apoptosis by arresting cell cycle, regulating carcinogen metabolism and ontogenesis expression, inhibiting DNA binding and cell adhesion, migration, proliferation or differentiation, and blocking signaling pathways. This review covers the most recent literature to summarize structural categories and molecular anticancer mechanisms of phenolic compounds from medicinal herbs and dietary plants.

  6. Role of phenolic compounds in peptic ulcer: An overview.

    PubMed

    Sumbul, Sabiha; Ahmad, Mohd Aftab; Mohd, Asif; Mohd, Akhtar

    2011-07-01

    Peptic ulcer is the most common gastrointestinal tract (GIT) disorder in clinical practice, which affects approximately 5-10% of the people during their life. The use of herbal drugs for the prevention and treatment of various diseases is constantly developing throughout the world. This is particularly true with regard to phenolic compounds that probably constitute the largest group of plants secondary metabolites. Phenolic compounds have attracted special attention due to their health-promoting characteristics. In the past ten years a large number of the studies have been carried out on the effects of phenolic compounds on human health. Many studies have been carried out that strongly support the contribution of polyphenols to the prevention of cardiovascular diseases, cancer, osteoporosis, neurodegenerative diseases, and diabetes mellitus, and suggest a role in the prevention of peptic ulcer. Polyphenols display a number of pharmacological properties in the GIT area, acting as antisecretory, cytoprotective, and antioxidant agents. The antioxidant properties of phenolic compounds have been widely studied, but it has become clear that their mechanisms of action go beyond the modulation of oxidative stress. Various polyphenolic compounds have been reported for their anti-ulcerogenic activity with a good level of gastric protection. Besides their action as gastroprotective, these phenolic compounds can be an alternative for the treatment of gastric ulcers. Therefore, considering the important role of polyphenolic compounds in the prevention or reduction of gastric lesions induced by different ulcerogenic agents, in this review, we have summarized the literature on some potent antiulcer plants, such as, Oroxylum indicum, Zingiber officinale, Olea europaea L., Foeniculum vulgare, Alchornea glandulosa, Tephrosia purpurea, and so on, containing phenolic compounds, namely, baicalein, cinnamic acid, oleuropein, rutin, quercetin, and tephrosin, respectively, as active

  7. Role of phenolic compounds in peptic ulcer: An overview

    PubMed Central

    Sumbul, Sabiha; Ahmad, Mohd. Aftab; Mohd., Asif; Mohd., Akhtar

    2011-01-01

    Peptic ulcer is the most common gastrointestinal tract (GIT) disorder in clinical practice, which affects approximately 5-10% of the people during their life. The use of herbal drugs for the prevention and treatment of various diseases is constantly developing throughout the world. This is particularly true with regard to phenolic compounds that probably constitute the largest group of plants secondary metabolites. Phenolic compounds have attracted special attention due to their health-promoting characteristics. In the past ten years a large number of the studies have been carried out on the effects of phenolic compounds on human health. Many studies have been carried out that strongly support the contribution of polyphenols to the prevention of cardiovascular diseases, cancer, osteoporosis, neurodegenerative diseases, and diabetes mellitus, and suggest a role in the prevention of peptic ulcer. Polyphenols display a number of pharmacological properties in the GIT area, acting as antisecretory, cytoprotective, and antioxidant agents. The antioxidant properties of phenolic compounds have been widely studied, but it has become clear that their mechanisms of action go beyond the modulation of oxidative stress. Various polyphenolic compounds have been reported for their anti-ulcerogenic activity with a good level of gastric protection. Besides their action as gastroprotective, these phenolic compounds can be an alternative for the treatment of gastric ulcers. Therefore, considering the important role of polyphenolic compounds in the prevention or reduction of gastric lesions induced by different ulcerogenic agents, in this review, we have summarized the literature on some potent antiulcer plants, such as, Oroxylum indicum, Zingiber officinale, Olea europaea L., Foeniculum vulgare, Alchornea glandulosa, Tephrosia purpurea, and so on, containing phenolic compounds, namely, baicalein, cinnamic acid, oleuropein, rutin, quercetin, and tephrosin, respectively, as active

  8. Characteristic of phenolic compound and antioxidant activity of fermented broccoli (Brassica oleracea L. ssp.) beverage by lactic acid bacteria (LAB)

    NASA Astrophysics Data System (ADS)

    Maryati, Yati; Susilowati, Agustine; Melanie, Hakiki; Lotulung, Puspa D.

    2017-01-01

    Broccoli (Brassica oleracea L. ssp.) has a relatively high nutrient content, especially as a source of vitamins, minerals and fiber and contain bioactive compounds that act as antioxidants. In order to increase the nutritional value and innovate new products, fermentation process involving rich-antioxidants lactic acid bacteria (LAB) was done. The aim of this study is to determine the content of bioactive components, such as total polyphenols, total acid and antioxidant activity of the mixed culture of LAB (L. bulgaricus, S. thermophulus, L. acidophilus, Bd. bifidum)-fermented broccoli extracts. Ratio of fermented broccoli extract and concentration of starter cultureLAB was varied in the range of 5, 10, 15 and 20% (v/v), and the alterations of characteristics of the fermented broccoli extract, before and after fermentation (0 and 24 hours), were evaluated. The results showed that fermentation functional beverage broccoli with different concentrations of LAB cultures affect the antioxidant activity, total polyphenols, total acid and total cell of LAB generated. The optimum conditions obtained for the highest antioxidant activity of 6.74%, at aculture concentration of 20% during fermentation time of 24 h with a pH value of 4.29, total sugar of 10.89%, total acids of 0.97%, total polyphenols of 0.076%, and total LAB of 13.02 + 0.05 log cfu /ml.

  9. 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.

  10. Phenolic compounds and chromatographic profiles of pear skins (Pyrus spp.).

    PubMed

    Lin, Long-Ze; Harnly, James M

    2008-10-08

    A standardized profiling method based on liquid chromatography with diode array and electrospray ionization/mass spectrometric detection (LC-DAD-ESI/MS) was used to analyze the phenolic compounds in the skins of 16 pears (Pyrus spp.). Thirty-four flavonoids and 19 hydroxycinnamates were identified. The main phenolic compounds (based on peak area) in all of the pear skins were arbutin and chlorogenic acid. The remaining phenolics varied widely in area and allowed the pears to be divided into four groups. Group 1, composed of four Asian pears (Asian, Asian brown, Korean, and Korean Shinko), contained only trace quantities of the remaining phenolics. Yali pear (group 2) contained significant amounts of dicaffeoylquinic acids. Fragrant pear (group 3) contained significant quantities of quercetin glycosides and lesser quantities of isorhamnetin glycosides and the glycosides of luteolin, apigenin, and chrysoeriol. The remaining 10 pears (group 4) (Bartlett, Beurre, Bosc, Comice, D'Anjou, Forelle, Peckham, Red, Red D'Anjou, and Seckel) contained significant quantities of isorhamnetin glycosides and their malonates and lesser quantities of quercetin glycosides. Red D'Anjou, D'Anjou, and Seckel pears also contained cyanidin 3-O-glucoside. Thirty-two phenolic compounds are reported in pear skins for the first time.

  11. 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

  12. A phenolic acid phenethyl urea compound inhibits lipopolysaccharide-induced production of nitric oxide and pro-inflammatory cytokines in cell culture.

    PubMed

    Hwang, Jung-Min; Yu, Ji-Yeon; Jang, Young-Oh; Kim, Beom-Tae; Hwang, Ki-Jun; Jeon, Young-Mi; Lee, Jeong-Chae

    2010-04-01

    We previously used the Curtius rearrangement to synthesize various phenolic acid phenethyl urea compounds from phenolic acids and demonstrated their beneficial anti-oxidant and anti-cancer effects. Here, we investigated the effects of one of these synthetic compounds, (E)-1-(3,4-dihydroxystyryl)-3-(4-hydroxyphenethyl)urea (DSHP-U), on nitric oxide (NO) production, inducible nitric oxide synthase (iNOS) expression, and cytokine secretion in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. DSHP-U suppressed LPS-induced NO production and iNOS expression at a concentration of 50 microM and inhibited LPS-induced phosphorylation of extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK), and p38 kinase. Inhibitors of phosphorylated (p)-ERK and p-p38, but not of p-JNK, reduced LPS-stimulated NO production. DSHP-U also prevented the nuclear translocation of the Rel A (p65) subunit and DNA-NF-kappaB binding by suppressing IkappaBalpha phosphorylation and by the degradation of IkappaBalpha in LPS-stimulated cells. Furthermore, DSHP-U decreased the production of tumor necrosis factor-alpha, interleukin (IL)-1beta, and IL-6 in LPS-treated macrophages. However, the LPS-stimulated expression of LPS receptors, such as Toll-like receptor 4, myeloid differentiation factor-2, and CD14, was unchanged after DSHP-U treatment at significantly high levels. Our data suggest that DSHP-U blocks NO and inflammatory cytokine production in LPS-stimulated macrophages and that these effects are mainly mediated through the inhibition of the ERK/p38- and NF-kappaB signaling pathways.

  13. 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

  14. Tunisian table olive phenolic compounds and their antioxidant capacity.

    PubMed

    Ben Othman, N; Roblain, D; Thonart, P; Hamdi, M

    2008-05-01

    For the 1st time, 4 olive cultivars, the Meski, Chemlali, Besbessi, and Tounsi, from the Tunisian market were investigated to evaluate the phenolic compounds' contribution in nutritional value of table olives. From the Meski cultivar, we have chosen 4 different samples to evaluate differences within the same cultivar. Basic characteristics and total phenolic content were evaluated in flesh and kernel. The highest value of flesh phenolic content was observed in sample M4 of the Meski cultivar; however, the lowest value was observed in the Besbessi cultivar and they were 1801 and 339 mg GA/100 g dry weight, respectively. The main simple phenolic compounds identified in flesh extracts are hydroxytyrosol, tyrosol, and vanillic acid. Oleuropein was not detected in any samples. The antioxidant activity of Tunisian olive flesh varies between 212 and 462 muM TEAC/g of dry weight. Antioxidant activity of olives was related to their phenolic content but we found a low correlation between phenolic content and TEAC.

  15. 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...

  16. [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.

  17. 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

  18. 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.

  19. 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.

  20. Determination of phenolic compounds in Prunella L. by liquid chromatography-diode array detection.

    PubMed

    Sahin, Saliha; Demir, Cevdet; Malyer, Hulusi

    2011-07-15

    Four species of Prunella L. (Prunella vulgaris L., Prunella laciniata L., Prunella grandiflora L. and Prunella orientalis Bornm.) belong to the family of Lamiaceae and representing popular Western and Chinese herbal medicine were examined for the content of phenolic compounds. Phenolic acids (rosmarinic acid, caffeic acid, ferulic acid, chlorogenic acid, protocatechuic acid), flavonoids (rutin, quercetin) in different quantitative proportions depending on extracts were determined by the rapid, selective and accurate method combining solvent/acid hydrolysis extraction and high performance liquid chromatography-diode array detection (HPLC-DAD). Water, methanol, butanol, acetonitrile, ethyl acetate, hexane and their acidic solutions were used to examine the efficiency of different solvent systems for the extraction of phenolic compounds. Acid hydrolysis extraction was established as the most suitable extraction method for phenolic compounds.

  1. Mechanisms of action of phenolic compounds in olive.

    PubMed

    Rafehi, Haloom; Ververis, Katherine; Karagiannis, Tom C

    2012-06-01

    Olive oil, an oil rich in monounsaturated fatty acids (MUFCs) and minor constituents including phenolic compounds, is a major component of the Mediterranean diet. The potential health benefits of the Mediterranean diet were highlighted by the seminal Seven Countries Study, and more contemporary research has identified olive oil as a major element responsible for these effects. It is emerging that the phenolic compounds are the most likely candidates accounting for the cardioprotective and cancer preventative effects of extra virgin olive oil (EVOO). In particular, the phenolic compound, hydroxytyrosol has been identified as one of the most potent antioxidants found in olive oil. This review will briefly consider historical aspects of olive oil research and the biological properties of phenolic compounds in olive oil will be discussed. The focus of the discussion will be related to the mechanisms of action of hydroxytyrosol. Studies have demonstrated that hydroxytyrosol induces apoptosis and cell cycle arrest in cancer cells. Further, research has shown that hydroxytyrosol can prevent cardiovascular disease by reducing the expression of adhesion molecules on endothelial cells and preventing the oxidation of low-density lipoprotein (LDL). The molecular mechanisms accounting for these effects are reviewed.

  2. Phenolic compounds and antioxidant activity of kernels and shells of Mexican pecan (Carya illinoinensis).

    PubMed

    de la Rosa, Laura A; Alvarez-Parrilla, Emilio; Shahidi, Fereidoon

    2011-01-12

    The phenolic composition and antioxidant activity of pecan kernels and shells cultivated in three regions of the state of Chihuahua, Mexico, were analyzed. High concentrations of total extractable phenolics, flavonoids, and proanthocyanidins were found in kernels, and 5-20-fold higher concentrations were found in shells. Their concentrations were significantly affected by the growing region. Antioxidant activity was evaluated by ORAC, DPPH•, HO•, and ABTS•-- scavenging (TAC) methods. Antioxidant activity was strongly correlated with the concentrations of phenolic compounds. A strong correlation existed among the results obtained using these four methods. Five individual phenolic compounds were positively identified and quantified in kernels: ellagic, gallic, protocatechuic, and p-hydroxybenzoic acids and catechin. Only ellagic and gallic acids could be identified in shells. Seven phenolic compounds were tentatively identified in kernels by means of MS and UV spectral comparison, namely, protocatechuic aldehyde, (epi)gallocatechin, one gallic acid-glucose conjugate, three ellagic acid derivatives, and valoneic acid dilactone.

  3. 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

    2015-05-06

    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.

  4. 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.

  5. Content of different groups of phenolic compounds in microshoots of Juglans regia cultivars and studies on antioxidant activity

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phenolic and other compounds were extracted from micropropagated axillary shoots (microshoots) of the walnut (Juglans regia L.) cultivars ‘Chandler’, ‘Howard’, ‘Kerman’, ‘Sunland’, and ‘Z63’. Among cultivars, microshoots showed differences in phenolic compounds, phenolic acids, flavonoids and proant...

  6. Bread formulated with guava powder was enriched in phenolic and aroma compounds, and was highly acceptable by consumers.

    PubMed

    Castelo-Branco, Vanessa N; Lago, Mabel G; Minuzzo, Daniela A; Moura-Nunes, Nathália; Torres, Alexandre G; Nunes, Juliana C; Monteiro, Mariana

    2016-12-01

    Guava powder (GP) was used as source of aroma and phenolic compounds to fortify wheat bread 10% (GB10) and 20% (GB20), substituting for wheat flour. Phenolic compounds, antioxidant capacity, volatile compounds profile, and sensory acceptability of control bread (CB; without GP) and guava breads (GB) were evaluated. Incorporation of GP increased roughly 2-to-3-fold the phenolic compounds contents of bread. Ten phenolic compounds were identified in GB20, and quercetin-3-O-rutinoside was the major compound, while in CB, ferulic acid was the major among the six phenolic compounds in CB. Bread making seemed to promote the release of phenolic compounds from structural components. Breads incorporated with GP presented a richer volatile profile than CB, especially due to the presence of terpenes. GB improved aroma profile of bread. GP added aroma compounds and phenolic antioxidants, and seemed to be an interesting approach to enhance bread bioactivity and acceptability.

  7. 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

  8. Sensitive determination of phenolic compounds using high-performance liquid chromatography with cerium(IV)-rhodamine 6G-phenolic compound chemiluminescence detection.

    PubMed

    Zhang, Qunlin; Cui, Hua; Myint, Aung; Lian, Mei; Liu, Lijuan

    2005-11-18

    A simple, selective and sensitive determination method of 20 phenolic compounds has been developed using high-performance liquid chromatography (HPLC) with chemiluminescence detection. The method is based on the chemiluminescent enhancement by phenolic compound of the cerium(IV)-rhodamine 6G system in sulfuric acid medium. Twenty phenolic compounds were separated on a XDB-C(8) column with a gradient elution using a mixture of methanol and 1.0% acetic acid as a mobile phase. Under the optimized conditions, a linear working range extends 2 orders of magnitude with the relative standard deviations of intra- and inter-day precision below 4.0%, and the detection limits (S/N = 3) were in the range of 1.5-82.1 ng/ml. The chemiluminescence reaction was compatible with the mobile phase of high-performance liquid chromatography. The proposed method has been successfully applied to the assay of phenolic compounds in red wine without any pretreatment.

  9. The anti-inflammatory potential of phenolic compounds in grape juice concentrate (G8000™) on 2,4,6-trinitrobenzene sulphonic acid-induced colitis.

    PubMed

    Paiotti, Ana Paula Ribeiro; Neto, Ricardo Artigiani; Marchi, Patrícia; Silva, Roseane Mendes; Pazine, Vanessa Lima; Noguti, Juliana; Pastrelo, Mauricio Mercaldi; Gollücke, Andréa Pittelli Boiago; Miszputen, Sender Jankiel; Ribeiro, Daniel Araki

    2013-09-28

    Chronic inflammatory bowel disease is characterised by an up-regulation of the synthesis and release of a variety of pro-inflammatory mediators leading to excessive tissue injury. Flavonoids are able to inhibit enzymes and/or due to their antioxidant properties regulate the immune response. The goal of the present study was to evaluate the mechanisms of action of phenolic compounds present in grape juice on 2,4,6-trinitrobenzene sulphonic acid (TNBS)-induced colitis. A total of forty-one male Wistar rats were randomised into seven groups: negative control group; TNBS non-treated induced colitis; 2% grape juice control group; 1% grape juice 24 h after TNBS colitis induction; 1% grape juice on day 7 after colitis induction; 2% grape juice 24 h after colitis induction; 2% grape juice on day 7 after colitis induction. The 1% grape juice-treated induced colitis group showed marked clinical improvement when compared with the TNBS-induced colitis group. Rats that received 1% grape juice, on day 7 after colitis induction, presented reduced intensity of macroscopic and histological scores. Statistically significant differences (P,0·05) of TNF-a and inducible NO synthase mRNA expression were detected in the groups treated with grape juice at the 1% dose after inducing experimental colitis when compared with the TNBS group. Grape juice reduced the noxious effects induced by colitis caused by TNBS, especially at the 1% dose.

  10. Influence of Controlled Postflowering Temperature and Daylength on Individual Phenolic Compounds in Four Black Currant Cultivars.

    PubMed

    Woznicki, Tomasz L; Aaby, Kjersti; Sønsteby, Anita; Heide, Ola M; Wold, Anne-Berit; Remberg, Siv F

    2016-02-03

    The effects of postflowering temperature and daylength on the concentration of individual phenolic compounds were studied in black currant (Ribes nigrum L.) berries under controlled phytotron conditions. The four cultivars studied varied greatly in their concentrations of individual phenolic compounds and temperature stability for accumulation. The concentrations of a wide range of identified phenolic compounds were strongly influenced by temperature over the 12-24 °C range, often with opposite temperature gradient patterns for compounds within the same subclass. Accumulation of anthocyanins and flavonols increased under natural long day conditions, which provided an increased daily light integral, while under identical light energy conditions, photoperiod had little or no effect on the concentration of phenolic compounds. Furthermore, with the exception of members of the hydroxycinnamic acid subclass, the concentration of most phenolic compounds was higher in berries ripened outdoors than in the phytotron, apparently due to screening of UV-B radiation by the glass cover.

  11. Effect of phenolic acids on glucose and organic acid metabolism by lactic acid bacteria from wine.

    PubMed

    Campos, Francisco M; Figueiredo, Ana R; Hogg, Tim A; Couto, José A

    2009-06-01

    The influence of phenolic (p-coumaric, caffeic, ferulic, gallic and protocatechuic) acids on glucose and organic acid metabolism by two strains of wine lactic acid bacteria (Oenococcus oeni VF and Lactobacillus hilgardii 5) was investigated. Cultures were grown in modified MRS medium supplemented with different phenolic acids. Cellular growth was monitored and metabolite concentrations were determined by HPLC-RI. Despite the strong inhibitory effect of most tested phenolic acids on the growth of O. oeni VF, the malolactic activity of this strain was not considerably affected by these compounds. While less affected in its growth, the capacity of L. hilgardii 5 to degrade malic acid was clearly diminished. Except for gallic acid, the addition of phenolic acids delayed the metabolism of glucose and citric acid in both strains tested. It was also found that the presence of hydroxycinnamic acids (p-coumaric, caffeic and ferulic) increased the yield of lactic and acetic acid production from glucose by O. oeni VF and not by L. hilgardii 5. The results show that important oenological characteristics of wine lactic acid bacteria, such as the malolactic activity and the production of volatile organic acids, may be differently affected by the presence of phenolic acids, depending on the bacterial species or strain.

  12. 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...

  13. 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.

  14. Phenolic acids in berries, fruits, and beverages.

    PubMed

    Mattila, Pirjo; Hellström, Jarkko; Törrönen, Riitta

    2006-09-20

    The contents of soluble and total phenolic acids were analyzed in samples of 29 berries and berry products, 24 fruits and fruit peels, and 12 beverages. Variation of phenolic acids in berries was also studied. Soluble phenolic acids were extracted with methanolic acetic acid, and a tentative quantification was performed by high-performance liquid chromatography (HPLC). The total phenolic acid content was determined by HPLC after alkaline and acid hydrolyses. The content of total phenolic acids as aglycones in the above samples varied from 0 (pear cider) to 103 mg/100 g fresh weight (rowanberry). Besides rowanberry, the best phenolic acid sources among berries were chokeberry (96 mg/100 g), blueberry (85 mg/100 g), sweet rowanberry (75 mg/100 g), and saskatoon berry (59 mg/100 g). Among fruits, the highest contents (28 mg/100 g) were determined in dark plum, cherry, and one apple variety (Valkea Kuulas). Coffee (97 mg/100 g) as well as green and black teas (30-36 mg/100 g) were the best sources among beverages. Caffeic acid dominated in all of these samples except in tea brews. Variation in the phenolic acid contents of the berries was either small or moderate.

  15. Unravelling the total antioxidant capacity of pinotage wines: contribution of phenolic compounds.

    PubMed

    de Beer, Dalene; Joubert, Elizabeth; Marais, Johann; Manley, Marena

    2006-04-19

    The total antioxidant capacity (TAC) and phenolic composition of 139 Pinotage wines (2002 and 2003 vintages) were determined using the 2,2'-azino-di(3-ethylbenzo-thialozine-sulfonic acid) scavenging assay and high-performance liquid chromatography, respectively. The contribution of individually quantified phenolic compounds to the wine TAC was calculated using their concentrations and Trolox equivalent antioxidant capacity (TEAC) values. The TEAC values of quercetin-3-galactoside, isorhamnetin, and peonidin-3-glucoside are reported for the first time. Between 11 and 24% of the measured TAC of Pinotage wines was explained by the sum of the calculated contributions of their quantified phenolic compounds comprising monomeric phenolic compounds and procyanidin B1. Ultrafiltration was carried out to attempt separation of monomeric and polymeric phenolic compounds. Analysis of ultrafiltration permeates and retentates enabled estimation of the TAC contribution of large molecular weight (MW) unknown compounds (46%) (>50 kDa), including oligomeric and polymeric phenolic compounds and small MW unknown compounds (34%) (<50 kDa). Three mixtures, containing 12 phenolic compounds in typical concentrations expected in Pinotage wines, exhibited 16-23% synergistic antioxidant activity. This suggests that synergy between phenolic compounds does play a role in the wine TAC but that it does not explain the large discrepancy between measured and calculated TAC values.

  16. A novel phenolic compound from Phyllanthus emblica.

    PubMed

    She, Gaimei; Cheng, Ruiyang; Sha, Lei; Xu, Yixia; Shi, Renbin; Zhang, Lanzhen; Guo, Yajian

    2013-04-01

    A new compound, mucic acid 3-O-gallate (1), was isolated from the fruit of Phyllanthus emblica L, together with 5 known compounds (2-6). Their structures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques, and by comparison with literature data.

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

    PubMed

    Slimestad, Rune; Vangdal, Eivind; Brede, Cato

    2009-12-09

    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).

  18. Two new phenolic compounds and antitumor activities of asparinin A from Asparagus officinalis.

    PubMed

    Li, Xue-Mei; Cai, Jin-Long; Wang, Le; Wang, Wen-Xiang; Ai, Hong-Lian; Mao, Zi-Chao

    2017-02-01

    Two new phenolic acid compounds, asparoffin C (1) and asparoffin D (2), together with four known compounds, asparenyol (3), gobicusin B (4), 1-methoxy-2-hydroxy-4-[5-(4-hydroxyphenoxy)-3-penten-1-ynyl] phenol (5), and asparinin A (6), have been isolated from the stems of Asparagus officinalis. The structures were established by extensive spectroscopic methods (MS and 1D and 2D NMR). Compound 6 has obvious antitumor activities both in vitro and in vivo.

  19. Reactivity of phenolic compounds towards free radicals under in vitro conditions.

    PubMed

    Mathew, Sindhu; Abraham, T Emilia; Zakaria, Zainul Akmar

    2015-09-01

    The free radical scavenging activity and reducing power of 16 phenolic compounds including four hydroxycinnamic acid derivatives namely ferulic acid, caffeic acid, sinapic acid and p-coumaric acid, benzoic acid and its derivatives namely protocatechuic acid, gallic acid and vanillic acid, benzene derivatives namely vanillin, vanillyl alcohol, veratryl alcohol, veratraldehyde, pyrogallol, guaiacol and two synthetic antioxidants, butylated hydroxy anisole (BHA) and propyl gallate were evaluated using 1,1-Diphenyl-2-picrylhydrazyl radical (DPPH(•)), 2,2'-Azinobis-3- ethylbenzothiazoline-6-sulfonic acid radical (ABTS(+•)), Hydroxyl radical ((•)OH) and Superoxide radical (O2 (•-)) scavenging assays and reduction potential assay. By virtue of their hydrogen donating ability, phenolic compounds with multiple hydroxyl groups such as protocatechuic acid, pyrogallol, caffeic acid, gallic acid and propyl gallate exhibited higher free radical scavenging activity especially against DPPH(•) and O2 (•-). The hydroxylated cinnamates such as ferulic acid and caffeic acid were in general better scavengers than their benzoic acid counter parts such as vanillic acid and protocatechuic acid. All the phenolic compounds tested exhibited more than 85 % scavenging due to the high reactivity of the hydroxyl radical. Phenolic compounds with multiple hydroxyl groups also exhibited high redox potential. Exploring the radical scavenging and reducing properties of antioxidants especially those which are found naturally in plant sources are of great interest due to their protective roles in biological systems.

  20. Experimental and theoretical binding affinity between polyvinylpolypyrrolidone and selected phenolic compounds from food matrices.

    PubMed

    Durán-Lara, Esteban F; López-Cortés, Xaviera A; Castro, Ricardo I; Avila-Salas, Fabián; González-Nilo, Fernando D; Laurie, V Felipe; Santos, Leonardo S

    2015-02-01

    Polyvinylpolypyrrolidone (PVPP) is a fining agent, widely used in winemaking and brewing, whose mode of action in removing phenolic compounds has not been fully characterised. The aim of this study was to evaluate the experimental and theoretical binding affinity of PVPP towards six phenolic compounds representing different types of phenolic species. The interaction between PVPP and phenolics was evaluated in model solutions, where hydroxyl groups, hydrophobic bonding and steric hindrance were characterised. The results of the study indicated that PVPP exhibits high affinity for quercetin and catechin, moderate affinity for epicatechin, gallic acid and lower affinity for 4-methylcatechol and caffeic acid. The affinity has a direct correlation with the hydroxylation degree of each compound. The results show that the affinity of PVPP towards phenols is related with frontier orbitals. This work demonstrates a direct correlation between the experimental affinity and the interaction energy calculations obtained through computational chemistry methods.

  1. Soluble phenolic compounds in different cultivars of red clover and alfalfa, and their implication for protection against proteolysis and ammonia production in ruminants

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Red clover contains phenolic compounds with roles in inhibiting proteolysis and loss of amino acids as ammonia. Alfalfa has been found to have lower concentrations of phenolic compounds, but few alfalfa and red clover cultivars have been compared for phenolic content. Total soluble phenolic compou...

  2. Biological activity of acetylated phenolic compounds.

    PubMed

    Fragopoulou, Elizabeth; Nomikos, Tzortzis; Karantonis, Haralabos C; Apostolakis, Constantinos; Pliakis, Emmanuel; Samiotaki, Martina; Panayotou, George; Antonopoulou, Smaragdi

    2007-01-10

    In recent years an effort has been made to isolate and identify biologically active compounds that are included in the Mediterranean diet. The existence of naturally occurring acetylated phenolics, as well as studies with synthetic ones, provide evidence that acetyl groups could be correlated with their biological activity. Platelet activating factor (PAF) is implicated in atherosclerosis, whereas its inhibitors seem to play a protective role against cardiovascular disease. The aim of this study was to examine the biological activity of resveratrol and tyrosol and their acetylated derivatives as inhibitors of PAF-induced washed rabbit platelet aggregation. Acetylation of resveratrol and tyrosol was performed, and separation was achieved by HPLC. Acetylated derivatives were identified by negative mass spectrometry. The data showed that tyrosol and its monoacetylated derivatives act as PAF inhibitors, whereas diacetylated derivatives induce platelet aggregation. Resveratrol and its mono- and triacetylated derivatives exert similar inhibitory activity, whereas the diacetylated ones are more potent inhibitors. In conclusion, acetylated phenolics exert the same or even higher antithrombotic activity compared to the biological activity of the initial one.

  3. Colonic catabolism of dietary phenolic and polyphenolic compounds from Concord grape juice.

    PubMed

    Stalmach, Angelique; Edwards, Christine A; Wightman, Jolynne D; Crozier, Alan

    2013-01-01

    After acute ingestion of 350 ml of Concord grape juice, containing 528 μmol of (poly)phenolic compounds, by healthy volunteers, a wide array of phase I and II metabolites were detected in the circulation and excreted in urine. Ingestion of the juice by ileostomists resulted in 40% of compounds being recovered intact in ileal effluent. The current study investigated the fate of these undigested (poly)phenolic compounds on reaching the colon. This was achieved through incubation of the juice using an in vitro model of colonic fermentation and through quantification of catabolites produced after colonic degradation and their subsequent absorption prior to urinary excretion by healthy subjects and ileostomy volunteers. A total of 16 aromatic and phenolic compounds derived from colonic metabolism of Concord grape juice (poly)phenolic compounds were identified by GC-MS in the faecal incubation samples. Thirteen urinary phenolic acids and aromatic compounds were excreted in significantly increased amounts after intake of the juice by healthy volunteers, whereas only two of these compounds were excreted in elevated amounts by ileostomists. The production of phenolic acids and aromatic compounds by colonic catabolism contributed to the bioavailability of Concord grape (poly)phenolic compounds to a much greater extent than phase I and II metabolites originating from absorption in the upper gastrointestinal tract. Catabolic pathways are proposed, highlighting the impact of colonic microbiota and subsequent phase II metabolism prior to excretion of phenolic compounds derived from (poly)phenolic compounds in Concord grape juice, which pass from the small to the large intestine.

  4. Characterization of nitrated phenolic compounds for their anti-oxidant, pro-oxidant, and nitration activities.

    PubMed

    Iwasaki, Yusuke; Nomoto, Maki; Oda, Momoko; Mochizuki, Keisuke; Nakano, Yuki; Ishii, Yuji; Ito, Rie; Saito, Koichi; Umemura, Takashi; Nishikawa, Akiyoshi; Nakazawa, Hiroyuki

    2011-09-01

    Coffee is one of the most widely consumed beverages worldwide. Evidence of the health benefits and the important contribution of coffee brew to the intake of anti-oxidants in the diet has increased coffee consumption. Chlorogenic acid (ChA) and caffeic acid (CaA) are the major phenolic compounds in coffee. However, phenolic compounds, which are generally effective anti-oxidants, can become pro-oxidants in the presence of Cu(2+) to induce DNA damage under certain conditions. On the other hand, sodium nitrite (NaNO(2)) is widely used as a food additive to preserve and tinge color on cured meat and fish. It is possible that phenolic compounds react with NaNO(2) under acidic conditions, such as gastric juice. In this study, we identified compounds produced by the reaction between ChA or CaA in coffee and NaNO(2) in artificial gastric juice. The identified phenolic compounds and nitrated phenolic compounds were assessed for their anti-oxidant, pro-oxidant, and nitration activities by performing an in vitro assay. The nitrated phenolic compounds seemed to show increased anti-oxidant activity and decreased pro-oxidant activity. However, one nitrated CaA compound that has a furoxan ring showed the ability to release NO(2)(-) in the neutral condition.

  5. 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.

  6. Characterization of phenolic compounds in rooibos tea.

    PubMed

    Krafczyk, Nicole; Glomb, Marcus A

    2008-05-14

    Polyphenols present in rooibos, a popular herbal tea from Aspalathus linearis, were isolated in two steps. First, phenolic ingredients were separated by multilayer countercurrent chromatography (MLCCC). Preparative high-performance liquid chromatography (HPLC) was then applied to obtain pure flavonoids. The purity and identity of isolated compounds was confirmed by different NMR experiments, HPLC-diode array detector (DAD), or gas chromatography-mass spectrometry (GC-MS) analysis. This strategy proved to be valid to isolate material in up to gram quantities and to verify known and previously not published polyphenol structures. In addition the chemistry of dihydrochalcones and related intermediates was studied. The dihydrochalcone aspalathin was oxidized to the corresponding flavanone- C-glycosides (( R)/( S)-eriodictyol-6- C-beta- D-glucopyranoside and ( R)/( S)-eriodictyol-8- C-beta- D-glucopyranoside). Flavanone-6- C-beta- D-glucopyranosides were further degraded to flavones isoorientin and orientin.

  7. Phenolic Biotransformations during Conversion of Ferulic Acid to Vanillin by Lactic Acid Bacteria

    PubMed Central

    Kaur, Baljinder; Kumar, Balvir

    2013-01-01

    Vanillin is widely used as food additive and as a masking agent in various pharmaceutical formulations. Ferulic acid is an important precursor of vanillin that is available in abundance in cell walls of cereals like wheat, corn, and rice. Phenolic biotransformations can occur during growth of lactic acid bacteria (LAB), and their production can be made feasible using specialized LAB strains that have been reported to produce ferulic acid esterases. The present study aimed at screening a panel of LAB isolates for their ability to release phenolics from agrowaste materials like rice bran and their biotransformation to industrially important compounds such as ferulic acid, 4-ethyl phenol, vanillic acid, vanillin, and vanillyl alcohol. Bacterial isolates were evaluated using ferulic acid esterase, ferulic acid decarboxylase, and vanillin dehydrogenase assays. This work highlights the importance of lactic acid bacteria in phenolic biotransformations for the development of food grade flavours and additives. PMID:24066293

  8. The Health Benefiting Mechanisms of Virgin Olive Oil Phenolic Compounds.

    PubMed

    Parkinson, Lisa; Cicerale, Sara

    2016-12-16

    Virgin olive oil (VOO) is credited as being one of the many healthful components associated with the Mediterranean diet. Mediterranean populations experience reduced incidence of chronic inflammatory disease states and VOO is readily consumed as part of an everyday Mediterranean dietary pattern. VOO is rich in phenolic compounds and the health promoting benefits of these phenolics are now established. Recent studies have highlighted the biological properties of VOO phenolic compounds elucidating their anti-inflammatory activities. This paper will review current knowledge on the anti-inflammatory and nutrigenomic, chemoprotective and anti-atherosclerotic activities of VOO phenolics. In addition the concentration, metabolism and bioavailability of specific phenolic compounds will be discussed. The evidence presented in the review concludes that oleurepein, hydroxytyrosol and oleocanthal have potent pharmacological activities in vitro and in vivo; however, intervention studies with biologically relevant concentrations of these phenolic compounds are required.

  9. Effects of Ultrasonic Irradiation on Phenolic Compounds in Wine

    NASA Astrophysics Data System (ADS)

    Masuzawa, Nobuyoshi; Ohdaira, Etsuzo; Ide, Masao

    2000-05-01

    Red wine has been of interest recently because many poly-phenols, that are considered to be good for health, are contained therein. Since ultrasonic irradiation accelerates maturation, its effects on phenolic compounds in wine were investigated in this study. Effects were evaluated using the indices developed by Glories. It was found that weak ultrasonic irradiation promotes an increase in the amount of phenolic compounds in red wine.

  10. 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.

  11. 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-...

  12. Retardation of quality changes in camel meat sausages by phenolic compounds and phenolic extracts.

    PubMed

    Maqsood, Sajid; Manheem, Kusaimah; Abushelaibi, Aisha; Kadim, Isam Tawfik

    2016-11-01

    Impact of tannic acid (TA), date seed extract (DSE), catechin (CT) and green tea extract (GTE) on lipid oxidation, microbial load and textural properties of camel meat sausages during 12 days of refrigerated storage was investigated. TA and CT showed higher activities in all antioxidative assays compared to DSE and GTE. Lipid oxidation and microbial growth was higher for control sausages when compared to other samples. TA and CT at a level of 200 mg/kg were more effective in retarding lipid oxidation and lowering microbial count (P < 0.05). Sausages treated with TA and DSE were found to have higher hardness, gumminess and chewiness values compared to other treatments (P < 0.05). Addition of different phenolic compounds or extract did not influence the sensory color of sausages. Furthermore, sensory quality was also found to be superior in TA and CT treated sausages. Therefore, pure phenolic compounds (TA and CT) proved to be more effective in retaining microbial and sensorial qualities of camel meat sausages compared to phenolic extracts (GTE and DSE) over 12 days of storage at 4°C.

  13. HPLC-DAD-ESI-MS analysis of phenolic compounds during ripening in exocarp and mesocarp of tomato fruit.

    PubMed

    Carrillo-López, Armando; Yahia, Elhadi

    2013-12-01

    Identification of phenolic compounds was done by means of liquid chromatography (HPLC) coupled to mass spectrometry (MS) using the electrospray ionization interface (ESI). Quantification of phenolic compounds was carried out by using HPLC with diode array detector (DAD) in exocarp and mesocarp of tomato fruit at 6 different ripeness stages (mature-green, breakers, turning, pink, light-red, and red). Several phenolic compounds were identified including chlorogenic acid, caffeic acid, p-coumaric acid, ferulic acid, and rutin and some combined phenolic acids were tentatively identified, mainly glycosides, such as caffeoyl hexose I, caffeoyl hexose II, caffeoylquinic acid isomer, dicaffeoylquinic acid, p-coumaroyl hexose I, p-coumaroyl hexose II, feruloyl hexose I, feruloyl hexose II, siringyl hexose, and caffeoyl deoxyhexose hexose. Fruit exocarp had higher quantities of total soluble phenolics (TSP) compared to mesocarp. During ripening, TSP increased in both exocarp and mesocarp, mainly in exocarp. While rutin increased, chlorogenic acid decreased in both tissues: exocarp and mesocarp.

  14. 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.

  15. Characterization of phenolic compounds from lingonberry (Vaccinium vitis-idaea).

    PubMed

    Ek, Sari; Kartimo, Heikki; Mattila, Sampo; Tolonen, Ari

    2006-12-27

    Phenolic compounds from the lingonberry (Vaccinium vitis-idaea) were identified using LC-TOFMS, LC-MS/MS, and NMR experiments. The compounds were extracted from the plant material using methanol in an ultrasonicator and further isolated and purified using solid-phase extraction and preparative liquid chromatographic techniques. A total of 28 phenolic compounds were at least tentatively identified, including flavonols, anthocyanidins, catechins and their glycosides, and different caffeoyl and ferulic acid conjugates. This is apparently the first report of coumaroyl-hexose-hydroxyphenol, caffeoyl-hexose-hydroxyphenol, coumaroyl-hexose-hydroxyphenol, quercetin-3-O-alpha-arabinofuranoside, kaempferol-pentoside, and kaempferol-deoxyhexoside in the plant, and the flavonol acylglycosides quercetin-3-O-[4' '-(3-hydroxy-3-methylglutaroyl)]-alpha-rhamnose and kaempferol-3-O-[4' '-(3-hydroxy-3-methylglutaroyl)]-alpha-rhamnose are presented here for the first time ever. In addition, more detailed structure in comparison to earlier reports is described for some compounds previously known to exist in lingonberry.

  16. 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.

  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.

  18. Phenolic Melatonin-Related Compounds: Their Role as Chemical Protectors against Oxidative Stress.

    PubMed

    Galano, Annia; Castañeda-Arriaga, Romina; Pérez-González, Adriana; Tan, Dun-Xian; Reiter, Russel J

    2016-10-29

    There is currently no doubt about the serious threat that oxidative stress (OS) poses to human health. Therefore, a crucial strategy to maintain a good health status is to identify molecules capable of offering protection against OS through chemical routes. Based on the known efficiency of the phenolic and melatonin (MLT) families of compounds as antioxidants, it is logical to assume that phenolic MLT-related compounds should be (at least) equally efficient. Unfortunately, they have been less investigated than phenols, MLT and its non-phenolic metabolites in this context. The evidence reviewed here strongly suggests that MLT phenolic derivatives can act as both primary and secondary antioxidants, exerting their protection through diverse chemical routes. They all seem to be better free radical scavengers than MLT and Trolox, while some of them also surpass ascorbic acid and resveratrol. However, there are still many aspects that deserve further investigations for this kind of compounds.

  19. 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

  20. Natural Phenolic Compounds as Therapeutic and Preventive Agents for Cerebral Amyloidosis.

    PubMed

    Yamada, Masahito; Ono, Kenjiro; Hamaguchi, Tsuyoshi; Noguchi-Shinohara, Moeko

    2015-01-01

    Epidemiological studies have suggested that diets rich in phenolic compounds may have preventive effects on the development of dementia or Alzheimer's disease (AD). We investigated the effects of natural phenolic compounds, such as myricetin (Myr), rosmarinic acid (RA), ferulic acid (FA), curcumin (Cur) and nordihydroguaiaretic acid (NDGA) on the aggregation of amyloid β-protein (Aβ), using in vitro and in vivo models of cerebral Aβ amyloidosis. The in vitro studies revealed that these phenolic compounds efficiently inhibit oligomerization as well as fibril formation of Aβ through differential binding, whilst reducing Aβ oligomer-induced synaptic and neuronal toxicity. Furthermore, a transgenic mouse model fed orally with such phenolic compounds showed significant reduction of soluble Aβ oligomers as well as of insoluble Aβ deposition in the brain. These data, together with an updated review of the literature, indicate that natural phenolic compounds have anti-amyloidogenic effects on Aβ in addition to well-known anti-oxidative and anti-inflammatory effects, hence suggesting their potential as therapeutic and/or preventive agents for cerebral Aβ amyloidosis, including AD and cerebral amyloid angiopathy (CAA). Well-designed clinical trials or preventive interventions with natural phenolic compounds are necessary to establish their efficacy as disease-modifying agents.

  1. 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

    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.

  2. 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

  3. Chemicals from coal. Utilization of coal-derived phenolic compounds

    SciTech Connect

    Song, C.; Schobert, H.H.

    1999-07-01

    This article provides an overview for possible utilization of coal-derived phenolic compounds. Phenolic compounds are abundant in coal-derived liquids. Coal-derived phenolic compounds include phenol, cresol, catechol, methylcatechol, naphthol, and their derivatives. Liquids from coal liquefaction, pyrolysis, gasification, and carbonization are potential sources of phenolic chemicals, although certain processing and separation are needed. There are opportunities for coal-based phenolic chemicals, because there are existing industrial applications and potential new applications. Currently the petrochemical industry produces phenol in multi-step processes, and new research and development has resulted in a one-step process. Selective methylation of phenol can produce a precursor for aromatic engineering plastics. Catalytic oxidation of phenol has been commercialized recently for catechol production. There are potential new uses of phenol that could replace large-volume multi-step chemical processes that are based on benzene as the starting material. New chemical research on coal and coal-derived liquids can pave the way for their non-fuel uses for making chemicals and materials.

  4. 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.

  5. 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.

  6. Diterpenes and phenolic compounds from Sideritis pullulans.

    PubMed

    Faiella, Laura; Piaz, Fabrizio Dal; Bader, Ammar; Braca, Alessandra

    2014-10-01

    Phytochemical investigation of Sideritis pullulans aerial part and root extracts allowed to isolate six ent-kaurane diterpenes, two phenylpropanoids, and one coumarin, identified as 1α,3α,7β,18-tetrahydroxy-ent-kaur-16-ene (sideripullol A) (1), 3α,11α,18-trihydroxy-ent-kaur-16-ene (sideripullol B) (2), 3α,7β,18-trihydroxy-17-nor-ent-kauran-16-one (sideritone A) (3), 3α,7β-dihydroxy-18-acetyloxy-17-nor-ent-kauran-16-one (sideritone B) (4), 3α,7β,16α,17-tetrahydroxy-18-acetyloxy-ent-kaurane (sideripullol C) (5), 7β,16α,17,18-tetrahydroxy-ent-kaurane (sideripullol D) (6), β-(3-methoxy-4-hydroxyphenyl)-ethyl-O-α-l-arabinopiranosyl-(1→2)-α-l-rhamnopyranosyl-(1→3)-6-O-t-feruloyl-β-d-glucopyranoside (sideritiside A) (7), β-(3,4-dihydroxyphenyl)-ethyl-O-α-l-arabinopiranosyl-(1→2)-α-l-rhamnopyranosyl-(1→3)-6-O-t-feruloyl-β-d-glucopyranoside (sideritiside B) (8), and 7-demethyl-8-methoxycoumarsabin (9), respectively. Twenty known compounds, including phenolics, flavonol glycosides, iridoids, diterpenes, sesquiterpenes, lignans, coumarins, and phenylpropanoids were also isolated and characterized. All diterpenes were evaluated for their cytotoxic activity.

  7. 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.

  8. [Efficient synthesis of multisubstituted aromatic compounds from phenol derivatives].

    PubMed

    Ikawa, Takashi

    2014-01-01

    Phenols are abundant in nature and diverse phenols are readily available commercially at low cost. Thus, phenols can be used as the raw materials for the synthesis of valuable multisubstituted aromatic compounds by the direct activation of phenolic hydroxyl groups (C-O bond activation), followed by substitutions with other substituents. Although the derivatization of phenolic hydroxyl groups to sulfonates, such as triflates, nonaflates, tosylates and mesylates, followed by the transition-metal-catalyzed coupling reactions has been extensively investigated for this purpose, the direct C-O bond activation of phenols for subsequent functional group transformation has been a long-standing challenge in modern organic synthesis. In this review, I have summarized my recent studies on the formal direct C-O bond activation of phenols using nonafluorobutanesulfonyl fluoride (NfF) for the synthesis of multisubstituted aromatics. I have focused on the dual use of NfF, a less expensive commercially available reagent, including the tentative formation of highly reactive nonaflates from phenols and the use of the liberated fluoride ion as a nucleophile to promote the reactions of nonaflates. The following four topics are discussed: 1) palladium-catalyzed coupling reactions of phenols, 2) novel preparation of benzynes from 2-silylphenols, 3) synthesis of fluorinated aromatic compounds via the formation of benzynes, and 4) Hiyama coupling of (tert-butyldimethylsilyl)arenes activated by internal phenolic hydroxyl groups.

  9. Bioactive amines and phenolic compounds in cocoa beans are affected by fermentation.

    PubMed

    do Carmo Brito, Brenda de Nazaré; Campos Chisté, Renan; da Silva Pena, Rosinelson; Abreu Gloria, Maria Beatriz; Santos Lopes, Alessandra

    2017-08-01

    Cocoa is the target of increased scientific research as it is one of the richest source of bioactive compounds. The formation of bioactive amines and their changes in cocoa beans during seven days of traditional fermentation was investigated for the first time. In addition, total phenolic compounds, anthocyanins contents and the scavenging capacity against ABTS radical were determined to monitor the fermentation process. Only two biogenic amines (tryptamine and tyramine) and two polyamines (spermidine and spermine) were detected in cocoa beans during fermentation. Fermentation was characterized by three stages: i) high levels of tryptamine, phenolics, and scavenging capacity; ii) high contents of spermine, total biogenic amines and total polyamines; and iii) the highest spermidine levels and total acidity, but the lowest total phenolic compounds and anthocyanins contents. The scavenging capacity of cocoa beans during fermentation correlated with total phenolic compounds and anthocyanins contents.

  10. 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.

  11. 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.

  12. 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.

  13. Evaluation of the Antiradical Properties of Phenolic Acids

    PubMed Central

    Koroleva, Olga; Torkova, Anna; Nikolaev, Ilya; Khrameeva, Ekaterina; Fedorova, Tatyana; Tsentalovich, Mikhail; Amarowicz, Ryszard

    2014-01-01

    Antioxidant capacity (AOC) against peroxyl radical and 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS) radical cation was measured for a series of p-hydroxybenzoic (HB) and p-hydroxycinnamic (HC) acids at different pH. Quantum-chemical computation was performed using Gaussian 3.0 software package to calculate the geometry and energy parameters of the same compounds. Significant correlations were revealed between AOC and a number of calculated parameters. The most significant AOC descriptors for the studied compounds against peroxyl radical were found to be HOMO energy, rigidity (η) and Mulliken charge on the carbon atom in m-position to the phenolic hydroxyl. The most significant descriptor of the antioxidant properties against the ABTS radical cation at pH 7.40 is electron transfer enthalpy from the phenolate ion. The mechanism of AOC realization has been proposed for HB and HC acids against both radicals. PMID:25229820

  14. Evaluation of the antiradical properties of phenolic acids.

    PubMed

    Koroleva, Olga; Torkova, Anna; Nikolaev, Ilya; Khrameeva, Ekaterina; Fedorova, Tatyana; Tsentalovich, Mikhail; Amarowicz, Ryszard

    2014-09-16

    Antioxidant capacity (AOC) against peroxyl radical and 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS) radical cation was measured for a series of p-hydroxybenzoic (HB) and p-hydroxycinnamic (HC) acids at different pH. Quantum-chemical computation was performed using Gaussian 3.0 software package to calculate the geometry and energy parameters of the same compounds. Significant correlations were revealed between AOC and a number of calculated parameters. The most significant AOC descriptors for the studied compounds against peroxyl radical were found to be HOMO energy, rigidity (η) and Mulliken charge on the carbon atom in m-position to the phenolic hydroxyl. The most significant descriptor of the antioxidant properties against the ABTS radical cation at рН 7.40 is electron transfer enthalpy from the phenolate ion. The mechanism of AOC realization has been proposed for HB and HC acids against both radicals.

  15. Extraction, identification, fractionation and isolation of phenolic compounds in plants with hepatoprotective effects.

    PubMed

    Pereira, Carla; Barros, Lillian; Ferreira, Isabel C F R

    2016-03-15

    The liver is one of the most important organs of human body, being involved in several vital functions and regulation of physiological processes. Given its pivotal role in the excretion of waste metabolites and drugs detoxification, the liver is often subjected to oxidative stress that leads to lipid peroxidation and severe cellular damage. The conventional treatments of liver diseases such as cirrhosis, fatty liver and chronic hepatitis are frequently inadequate due to side effects caused by hepatotoxic chemical drugs. To overcome this problematic paradox, medicinal plants, owing to their natural richness in phenolic compounds, have been intensively exploited concerning their extracts and fraction composition in order to find bioactive compounds that could be isolated and applied in the treatment of liver ailments. The present review aimed to collect the main results of recent studies carried out in this field and systematize the information for a better understanding of the hepatoprotective capacity of medicinal plants in in vitro and in vivo systems. Generally, the assessed plant extracts revealed good hepatoprotective properties, justifying the fractionation and further isolation of phenolic compounds from different parts of the plant. Twenty-five phenolic compounds, including flavonoids, lignan compounds, phenolic acids and other phenolic compounds, have been isolated and identified, and proved to be effective in the prevention and/or treatment of chemically induced liver damage. In this perspective, the use of medicinal plant extracts, fractions and phenolic compounds seems to be a promising strategy to avoid side effects caused by hepatotoxic chemicals.

  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. Subcritical water extraction of antioxidant phenolic compounds from XiLan olive fruit dreg.

    PubMed

    Yu, Xue-Mei; Zhu, Ping; Zhong, Qiu-Ping; Li, Meng-Ying; Ma, Han-Ruo

    2015-08-01

    Olive fruit dreg (OFD), waste from olive softdrink processing, has caused disposal problems. Nevertheless, OFD is a good source of functional ingredients, such as phenolic compounds. This study investigated the extraction conditions of phenolic compounds from OFD by using subcritical water (SCW) extraction method, antioxidant activity of SCW extracts, and components of phenolic compounds by LC-MS. SCW extraction experiments were performed in a batch stainless steel reactor at temperatures ranging from 100 to 180 °C at residence time of 5 to 60 min, and at solid-to-liquid ratio of 1:20 to 1:60. Higher recoveries of phenolic compounds [37.52 ± 0.87 mg gallic acid equivalents (GAE)/g, dry weight (DW)] were obtained at 160 °C, solid-to-liquid ratio of 1:50, and extract time of 30 min than at 2 h extraction with methanol (1.21 ± 0.16 mg GAE/g DW), ethanol (0.24 ± 0.07 mg GAE/g DW), and acetone (0.34 ± 0.01 mg GAE/g DW). The antioxidant activities of the SCW extracts were significantly stronger than those in methanol extracts at the same concentration of total phenolic contents. LC-MS analysis results indicated that SCW extracts contained higher amounts of phenolic compounds, such as chlorogenic acid, homovanillic acid, gallic acid, hydroxytyrosol, quercetin, and syringic acid. SCW at 160 °C, 30 min, and solid-to-liquid ratio of 1:50 may be a good substitute of organic solvents, such as methanol, ethanol, and acetone to recover phenolic compounds from OFD.

  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. Optimisation of the extraction of phenolic compounds from apples using response surface methodology.

    PubMed

    Alberti, Aline; Zielinski, Acácio Antonio Ferreira; Zardo, Danianni Marinho; Demiate, Ivo Mottin; Nogueira, Alessandro; Mafra, Luciana Igarashi

    2014-04-15

    The extraction of phenolic compounds from apples was optimised using response surface methodology (RSM). A Box-Behnken design was conducted to analyse the effects of solvent concentration (methanol or acetone), temperature and time on the extraction of total phenolic content, total flavonoids and antioxidant capacity (FRAP and DPPH). Analysis of the individual phenolics was performed by HPLC in optimal extraction conditions. The optimisation suggested that extraction with 84.5% methanol for 15 min, at 28 °C and extraction with 65% acetone for 20 min, at 10 °C were the best solutions for this combination of variables. RSM was shown to be an adequate approach for modelling the extraction of phenolic compounds from apples. Most of the experiments with acetone solutions extracted more bioactive compounds, and hence they had more antioxidant capacity, however, chlorogenic acid and phloridzin had higher yields (32.4% and 48.4%, respectively) in extraction with methanol.

  2. Inhibition of biogas production and biodegradability by substituted phenolic compounds in anaerobic sludge.

    PubMed

    Hernandez, J E; Edyvean, R G J

    2008-12-15

    Phenolic compounds are abundant in nature and organic wastes. This biomass may be utilised in biogas generation. Phenolics can inhibit the degradation of readily biodegradable organic fractions and their own biodegradation. In this work, assays were carried out under anaerobic conditions to study the inhibition of both gas production and biodegradability due to seven phenolic compounds and to study their adsorption onto sludge and autoxidation in the aqueous medium. Fifty percent inhibition was in the range of 120 to 594 mg of compound/g VSS. An initial enhancement followed by an inhibition of biogas formation was found. The inhibition by the phenolic compounds was found to be influenced by autoxidation, apolarity, type, size and number of substitutions. Biogas production is influenced by concentration rather than any pH change. The concentration of the phenolic compound was partially biomethanized and the degradation of gallic and caffeic acids by this process is reported here for the first time. The maximum total biodegradation of any phenolic compound was 63.85+/-2.73%, and remaining non-biodegradable fraction was autoxidized and adsorbed onto the sludge matrix. Inhibition of methanization and partial inhibition of background gas was found at concentrations between 800 and 1600 mg/L organic carbon.

  3. 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.

  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.

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

    DOE PAGES

    Aston, John E.; Apel, William A.; Lee, Brady D.; ...

    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

  6. 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.

  7. Bioprocessing of wheat bran improves in vitro bioaccessibility and colonic metabolism of phenolic compounds.

    PubMed

    Anson, Nuria Mateo; Selinheimo, Emilia; Havenaar, Rob; Aura, Anna-Marja; Mattila, Ismo; Lehtinen, Pekka; Bast, Aalt; Poutanen, Kaisa; Haenen, Guido R M M

    2009-07-22

    Ferulic acid (FA) is the most abundant phenolic compound in wheat grain, mainly located in the bran. However, its bioaccessibility from the bran matrix is extremely low. Different bioprocessing techniques involving fermentation or enzymatic and fermentation treatments of wheat bran were developed aiming at improving the bioaccessibility of phenolic compounds in bran-containing breads. The bioaccessibility of ferulic acid, p-coumaric acid, and sinapic acid was assessed with an in vitro model of upper gastrointestinal tract (TIM-1). Colonic metabolism of the phenolic compounds in the nonbioaccessible fraction of the breads was studied with an in vitro model of human colon (TIM-2). The most effective treatment was the combination of enzymes and fermentation that increased the bioaccessibility of FA from 1.1% to 5.5%. The major colonic metabolites were 3-(3-hydroxyphenyl)propionic acid and 3-phenylpropionic acid. Bran bioprocessing increases the bioaccessibility of phenolic compounds as well as the colonic end metabolite 3-phenylpropionic acid.

  8. The antiproliferative effect of dietary fiber phenolic compounds ferulic acid and p-coumaric acid on the cell cycle of Caco-2 cells.

    PubMed

    Janicke, Birgit; Hegardt, Cecilia; Krogh, Morten; Onning, Gunilla; Akesson, Björn; Cirenajwis, Helena M; Oredsson, Stina M

    2011-01-01

    Epidemiological and animal studies have shown that dietary fiber is protective against the development of colon cancer. Dietary fiber is a rich source of the hydroxycinnamic acids ferulic acid (FA) and p-coumaric acid (p-CA), which both may contribute to the protective effect. We have investigated the effects of FA and p-CA treatment on global gene expression in Caco-2 colon cancer cells. The Caco-2 cells were treated with 150 μM FA or p-CA for 24 h, and gene expression was analyzed with cDNA microarray technique. A total of 517 genes were significantly affected by FA and 901 by p-CA. As we previously have found that FA or p-CA treatment delayed cell cycle progression, we focused on genes involved in proliferation and cell cycle regulation. The expressions of a number of genes involved in centrosome assembly, such as RABGAP1 and CEP2, were upregulated by FA treatment as well as the gene for the S phase checkpoint protein SMC1L1. p-CA treatment upregulated CDKN1A expression and downregulated CCNA2, CCNB1, MYC, and ODC1. Some proteins corresponding to the affected genes were also studied. Taken together, the changes found can partly explain the effects of FA or p-CA treatment on cell cycle progression, specifically in the S phase by FA and G(2)/M phase by p-CA treatment.

  9. Cleanliness of common air sampling sorbents for application to phenolic compounds measurement using supercritical fluid extraction

    SciTech Connect

    Bowyer, J.R.; Pleil, J.D.

    1994-12-31

    The trace-level measurement of phenolic compounds in the ambient air is complicated by the acidic and polar nature of the compounds especially during recovery from the sampling medium. Recently, supercritical fluid extraction (SFE) has been proposed as an alternative extraction method to Soxhlet extraction or thermal desorption to achieve more efficient recoveries. For such methodology to become practical, the candidate sorbents must first be tested for stability and cleanliness under SFE conditions. This paper describes exploratory research results of background contamination tests and cleanup properties of some common air sampling sorbent media with respect to future application to phenolic compounds monitoring.

  10. Cleanliness of common air sampling sorbents for application to phenolic compounds measurement using supercritical fluid extraction

    SciTech Connect

    Bowyer, J.R.; Pleil, J.D.

    1994-01-01

    The trace-level measurement of phenolic compounds in the ambient air is complicated by the acidic and polar nature of the compounds especially during recovery from the sampling medium. Recently, supercritical fluid extraction (SFE) has been proposed as an alternative extraction method to Soxhlet extraction or thermal desorption to achieve more efficient recoveries. For such methodology to become practical, the candidate sorbents must first be tested for stability and cleanliness under SFE conditions. The paper describes exploratory research results of background contamination tests and cleanup properties of some common air sampling sorbent media with respect to future application to phenolic compounds monitoring.

  11. 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.

  12. Effect of Maturity on Phenolics (Phenolic Acids and Flavonoids) Profile of Strawberry Cultivars and Mulberry Species from Pakistan

    PubMed Central

    Mahmood, Tahir; Anwar, Farooq; Abbas, Mateen; Saari, Nazamid

    2012-01-01

    In this study, we investigated how the extent of ripeness affects the yield of extract, total phenolics, total flavonoids, individual flavonols and phenolic acids in strawberry and mulberry cultivars from Pakistan. In strawberry, the yield of extract (%), total phenolics (TPC) and total flavonoids (TFC) ranged from 8.5–53.3%, 491–1884 mg gallic acid equivalents (GAE)/100 g DW and 83–327 mg catechin equivalents (CE)/100 g DW, respectively. For the different species of mulberry the yield of extract (%), total phenolics and total flavonoids of 6.9–54.0%, 201–2287 mg GAE/100 g DW and 110–1021 mg CE/100 g DW, respectively, varied significantly as fruit maturity progressed. The amounts of individual flavonols and phenolic acid in selected berry fruits were analyzed by RP-HPLC. Among the flavonols, the content of myricetin was found to be high in Morus alba (88 mg/100 g DW), the amount of quercetin as high in Morus laevigata (145 mg/100 g DW) while kaempferol was highest in the Korona strawberry (98 mg/100 g DW) at fully ripened stage. Of the six phenolic acids detected, p-hydroxybenzoic and p-coumaric acid were the major compounds in the strawberry. M. laevigata and M. nigra contained p-coumaric acid and vanillic acid while M. macroura and M. alba contained p-hydroxy-benzoic acid and chlorogenic acid as the major phenolic acids. Overall, a trend to an increase in the percentage of extraction yield, TPC, TFC, flavonols and phenolic acids was observed as maturity progressed from un-ripened to fully-ripened stages. PMID:22605997

  13. Effect of maturity on phenolics (phenolic acids and flavonoids) profile of strawberry cultivars and mulberry species from Pakistan.

    PubMed

    Mahmood, Tahir; Anwar, Farooq; Abbas, Mateen; Saari, Nazamid

    2012-01-01

    In this study, we investigated how the extent of ripeness affects the yield of extract, total phenolics, total flavonoids, individual flavonols and phenolic acids in strawberry and mulberry cultivars from Pakistan. In strawberry, the yield of extract (%), total phenolics (TPC) and total flavonoids (TFC) ranged from 8.5-53.3%, 491-1884 mg gallic acid equivalents (GAE)/100 g DW and 83-327 mg catechin equivalents (CE)/100 g DW, respectively. For the different species of mulberry the yield of extract (%), total phenolics and total flavonoids of 6.9-54.0%, 201-2287 mg GAE/100 g DW and 110-1021 mg CE/100 g DW, respectively, varied significantly as fruit maturity progressed. The amounts of individual flavonols and phenolic acid in selected berry fruits were analyzed by RP-HPLC. Among the flavonols, the content of myricetin was found to be high in Morus alba (88 mg/100 g DW), the amount of quercetin as high in Morus laevigata (145 mg/100 g DW) while kaempferol was highest in the Korona strawberry (98 mg/100 g DW) at fully ripened stage. Of the six phenolic acids detected, p-hydroxybenzoic and p-coumaric acid were the major compounds in the strawberry. M. laevigata and M. nigra contained p-coumaric acid and vanillic acid while M. macroura and M. alba contained p-hydroxy-benzoic acid and chlorogenic acid as the major phenolic acids. Overall, a trend to an increase in the percentage of extraction yield, TPC, TFC, flavonols and phenolic acids was observed as maturity progressed from un-ripened to fully-ripened stages.

  14. 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

  15. 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

  16. Supercritical Extraction from Vinification Residues: Fatty Acids, α-Tocopherol, and Phenolic Compounds in the Oil Seeds from Different Varieties of Grape

    PubMed Central

    Agostini, F.; Bertussi, R. A.; Agostini, G.; Atti dos Santos, A. C.; Rossato, M.; Vanderlinde, R.

    2012-01-01

    Supercritical fluid extraction has been widely employed in the extraction of high purity substances. In this study, we used the technology to obtain oil from seeds from a variety of grapes, from vinification residues generated in the Southern region of the state of Rio Grande do Sul, Brazil. This work encompasses three varieties of Vitis vinifera (Moscato Giallo, Merlot, and Cabernet Sauvignon) and two of Vitis labrusca (Bordô e Isabel), harvested in 2005 and 2006. We obtained the highest oil content from Bordô (15.40%) in 2005 and from Merlot (14.66%), 2006. The biggest concentration of palmitic, stearic, and linoleic acids was observed in Bordô, 2005, and in Bordô, Merlot, and Moscato Giallo, 2006. Bordô showed the highest concentration of oleic acid and α-tocopherol in both seasons too. For the equivalent of procyanidins, we did not notice significant difference among the varieties from the 2005 harvest. In 2006, both varieties Isabel and Cabernet Sauvignon showed a value slightly lower than the other varieties. The concentration of total phenolics was higher in Bordô and Cabernet Sauvignon. The presence of these substances is related to several important pharmacological properties and might be an alternative to conventional processes to obtain these bioactives. PMID:22593706

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

    SciTech Connect

    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 at 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 rates

  18. 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.

  19. 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.

  20. 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

    2013-06-05

    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.

  1. 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

  2. Phenolic compounds and vitamin antioxidants of caper (Capparis spinosa).

    PubMed

    Tlili, Nizar; Khaldi, Abdelhamid; Triki, Saida; Munné-Bosch, Sergi

    2010-09-01

    Capparis spinosa shows strong resistance to the adverse Mediterranean conditions and it has nutritional and medicinal value. The aim of this study was to evaluate the contents of total phenolic compounds, rutin, tocopherols, carotenoids and vitamin C in leaves and flower buds of C. spinosa from different locations in Tunisia. Results showed the richness of caper with these compounds, especially phenolic compounds. Interestingly, it was also found the presence of both α- and γ-tocopherol in buds. Moreover, C. spinosa contained an appreciable level of vitamin C. The significant amounts of these antioxidants confirm the nutritional and medicinal value of caper.

  3. Improved HPLC determination of phenolic compounds in cv. golden delicious apples using a monolithic column.

    PubMed

    Chinnici, Fabio; Gaiani, Anna; Natali, Nadia; Riponi, Claudio; Galassi, Sergio

    2004-01-14

    A rapid HPLC-DAD determination of phenols in apple using an RP monolithic column is reported. Because of the hydrodynamic advantages offered by this kind of column and the use of acidified acetonitrile as eluent, assays of apple extracts can be performed in <21 min. Assays of pulp and peel extracts were carried out without the need for time-consuming sample pretreatment except filtration. Several flavanols, hydroxycinnamic acids, dihydrochalcones, and six quercetin glycosides were identified and quantified. A seventh quercetin derivative, two chalcone-related compounds, and three hydroxycinnamic derivatives were also found. Peels proved to be richer in phenols than pulps, the former being composed mainly of (-)-epicatechin, procyanidin B2, chlorogenic acid, phloridzin, hyperin, and avicularin. In pulps, where the chlorogenic acid was the principal phenolic compound, quercetin glycosides were found in very low amounts.

  4. Phenolic compounds prevent the oligomerization of α-synuclein and reduce synaptic toxicity.

    PubMed

    Takahashi, Ryoichi; Ono, Kenjiro; Takamura, Yusaku; Mizuguchi, Mineyuki; Ikeda, Tokuhei; Nishijo, Hisao; Yamada, Masahito

    2015-09-01

    Lewy bodies, mainly composed of α-synuclein (αS), are pathological hallmarks of Parkinson's disease and dementia with Lewy bodies. Epidemiological studies showed that green tea consumption or habitual intake of phenolic compounds reduced Parkinson's disease risk. We previously reported that phenolic compounds inhibited αS fibrillation and destabilized preformed αS fibrils. Cumulative evidence suggests that low-order αS oligomers are neurotoxic and critical species in the pathogenesis of α-synucleinopathies. To develop disease modifying therapies for α-synucleinopathies, we examined effects of phenolic compounds (myricetin (Myr), curcumin, rosmarinic acid (RA), nordihydroguaiaretic acid, and ferulic acid) on αS oligomerization. Using methods such as photo-induced cross-linking of unmodified proteins, circular dichroism spectroscopy, the electron microscope, and the atomic force microscope, we showed that Myr and RA inhibited αS oligomerization and secondary structure conversion. The nuclear magnetic resonance analysis revealed that Myr directly bound to the N-terminal region of αS, whereas direct binding of RA to monomeric αS was not detected. Electrophysiological assays for long-term potentiation in mouse hippocampal slices revealed that Myr and RA ameliorated αS synaptic toxicity by inhibition of αS oligomerization. These results suggest that Myr and RA prevent the αS aggregation process, reducing the neurotoxicity of αS oligomers. To develop disease modifying therapies for α-synucleinopathies, we examined effects of phenolic compounds on α-synuclein (αS) oligomerization. Phenolic compounds, especially Myricetin (Myr) and Rosmarinic acid (RA), inhibited αS oligomerization and secondary structure conversion. Myr and RA ameliorated αS synaptic toxicity on the experiment of long-term potentiation. Our results suggest that Myr and RA prevent αS aggregation process and reduce the neurotoxicity of αS oligomers. Phenolic compounds are good

  5. 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.

  6. Capillary electrochromatography of selected phenolic compounds of Chamomilla recutita.

    PubMed

    Fonseca, Fabiana N; Tavares, Marina F M; Horváth, Csaba

    2007-06-22

    This article explores the use of capillary electrochromatography for the analysis of chamomile (Chamomilla recutita L.) extracts. After a thorough study of analytical parameters such as mobile and stationary phase composition, applied voltage, and temperature, a methodology to determine 11 bioactive phenolic compounds (coumarins: herniarin, umbelliferone; phenylpropanoids: chlorogenic acid, caffeic acid; flavones: apigenin, apigenin-7-O-glucoside, luteolin, luteolin-7-O-glucoside; flavonols: quercetin, rutin and flavanone: naringenin) in chamomile extracts was proposed. The method was performed in a Hypersil SCX/C18 column with pH 2.8 phosphate buffer at 50 mmol L(-1) containing 50% acetonitrile (pH adjusted before the addition of the organic solvent). All compounds were separated in less than 7.5 min under isocratic conditions. Figures of merit include linearity (peak area versus apigenin concentration) from 50.0-1000 microg/mL (r2=0.995), and intra-day precision of retention time and peak area better than 1.3% CV and 15%, respectively. The limits of detection and quantification for apigenin were 35.0 microg/mL and 150.0 microg/mL, respectively. This article also describes an NMR 1H study, carried out to monitor a new clean-up procedure for extracts containing propyleneglycol, whose components are poorly retained in conventional octadecyl silica cartridges.

  7. Anaerobic biodegradation of phenolic compounds in digested sludge

    SciTech Connect

    Boyd, S.A.; Shelton, D.R.; Berry, D.; Tiedje, J.M.

    1983-07-01

    The authors examined the anaerobic degradation of phenol and the ortho, meta, and para isomers of chlorophenol, methoxyphenol, methylphenol (cresol),and nitrophenol in anaerobic sewage sludge diluted to 10% in a mineral salts medium. Of the 12 monosubstituted phenols studied, only p-chlorophenol and o-cresol were not significantly degraded during an 8-week incubation period. The phenol compounds degraded and the time required for complete substrate disappearance (in weeks) were: phenol (2), o-chlorophenol (3), m-chlorophenol (7), o-methoxyphenol (2), m- and p-methoxyphenol (1), m-cresol (7), p-cresol (3), and o-, m-, and p-nitrophenol (1). Complete mineralization of phenol, o-chlorophenol, m-cresol, p-cresol, o-nitrophenol, p-nitrophenol, and o-, m-, and p-methoxyphenol was observed. In general, the presence of Cl and NO/sub 2/ groups on phenols inhibited methane production. Elimination or transformation of these substituents was accompanied by increased methane production. o-Chlorophenol was metabolized to phenol, which indicated that dechlorination was the initial degradation step. The methoxyphenols were transformed to the corresponding dihydroxybenzene compounds, which were subsequently mineralized. (Refs. 14).

  8. 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.

  9. 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

  10. Recent developments in the HPLC separation of phenolic compounds.

    PubMed

    Kalili, Kathithileni M; de Villiers, André

    2011-04-01

    Phenolic compounds represent a class of highly complex naturally occurring molecules that possess a range of beneficial health properties. As a result, considerable attention has been devoted to the analysis of phenolics in a variety of samples. HPLC is the workhorse method for phenolic separation. However, conventional HPLC methods provide insufficient resolving power when faced with the complexity of real-world phenolic fractions. This limitation has been traditionally circumvented by extensive sample fractionation, multiple analysis methods and/or selective detection strategies. On the other hand, there is an increasing demand for improved throughput and resolving power from the chromatographic methods used for phenolic analyses. Fortunately, during the last decade, a number of important technological advances in LC have demonstrated significant gains in terms of both speed and resolution. These include ultra high-pressure liquid chromatography (UHPLC), high-temperature liquid chromatography (HTLC), multi-dimensional separations as well as various new stationary phase chemistries and morphologies. In recent years, these technologies have also found increasing application for phenolic analysis. This review seeks to provide an updated overview of the application of recent advances in HPLC to phenolic separation, with the emphasis on how these methodologies can contribute to improve performance in HPLC analysis of phenolics.

  11. Antimicrobial activity of phenolic acids against commensal, probiotic and pathogenic bacteria.

    PubMed

    Cueva, Carolina; Moreno-Arribas, M Victoria; Martín-Alvarez, Pedro J; Bills, Gerald; Vicente, M Francisca; Basilio, Angela; Rivas, Concepción López; Requena, Teresa; Rodríguez, Juan M; Bartolomé, Begoña

    2010-06-01

    Phenolic acids (benzoic, phenylacetic and phenylpropionic acids) are the most abundant phenolic structures found in fecal water. As an approach towards the exploration of their action in the gut, this paper reports the antimicrobial activity of thirteen phenolic acids towards Escherichia coli, Lactobacillus spp., Staphylococcus aureus, Pseudomonas aeruginosa and Candida albicans. The growth of E. coli ATCC 25922 was inhibited by only four of the phenolic acids tested at a concentration of 1000 microg/mL, whereas pathogenic E. coli O157:H7 (CECT 5947) was susceptible to ten of them. The genetically manipulated E. coli lpxC/tolC strain was highly susceptible to phenolic acids. The growth of lactobacilli (Lactobacillus paraplantarum LCH7, Lactobacillus plantarum LCH17, Lactobacillus fermentum LPH1, L. fermentum CECT 5716, Lactobacillus brevis LCH23, and Lactobacillus coryniformis CECT 5711) and pathogens (S. aureus EP167 and C. albicans MY1055) was also inhibited by phenolic acids, but to varying extents. Only P. aeruginosa PAO1 was not susceptible to any of the phenolic compounds tested. Structure-activity relationships of phenolic acids and some of their diet precursors [(+)-catechin and (-)-epicatechin] were established, based on multivariate analysis of microbial activities. The antimicrobial properties of phenolic acids reported in this paper might be relevant in vivo.

  12. Wide genetic variation in phenolic compound content of seed coats among black soybean cultivars

    PubMed Central

    Phommalath, Siviengkhek; Teraishi, Masayoshi; Yoshikawa, Takanori; Saito, Hiroki; Tsukiyama, Takuji; Nakazaki, Tetsuya; Tanisaka, Takatoshi; Okumoto, Yutaka

    2014-01-01

    Black soybeans have been used as a food source and also in traditional medicine because their seed coats contain natural phenolic compounds such as proanthocyanidin and anthocyanin. The objective of this research is to reveal the genetic variation in the phenolic compound contents (PCCs) of seed coats in 227 black soybean cultivars, most of which were Japanese landraces and cultivars. Total phenolics were extracted from seed coats using an acidic acetone reagent and the proanthocyanidin content, monomeric anthocyanin content, total flavonoids content, total phenolics content, and radical scavenging activity were measured. The cultivars showed wide genetic variation in PCCs. Each of the contents was highly correlated with one another, and was closely associated with radical scavenging activity. PCCs were also moderately associated by flowering date but not associated by seed weight. Cultivars with purple flowers had a tendency to produce higher PCCs compared with cultivars with white flowers, suggesting that the W1 locus for flower color can affect phenolic compound composition and content. Our results suggest that developing black soybean cultivars with high functional phenolic compounds activity is feasible. PMID:25914597

  13. 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.

  14. Effect of toasting intensity at cooperage on phenolic compounds in acacia (Robinia pseudoacacia) heartwood.

    PubMed

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

    2011-04-13

    The phenolic composition of heartwood from Robinia pseudoacacia, commonly known as false acacia, before and after toasting in cooperage was studied by HPLC-DAD and HPLC-DAD/ESI-MS/MS. A total of 41 flavonoid and nonflavonoid compounds were identified, some tentatively, and quantified. Seasoned acacia wood showed high concentrations of flavonoid and low levels of nonflavonoid compounds, the main compounds being the dihydroflavonols dihydrorobinetin, fustin, tetrahydroxy, and trihydroxymethoxy dihydroflavonol, the flavonol robinetin, the flavanones robtin and butin, and a leucorobinetinidin, none of which are found in oak wood. The low molecular weight (LMW) phenolic compounds present also differed from those found in oak, since compounds with a β-resorcylic structure, gallic related compounds, protocatechuic aldehyde, and some hydroxycinnamic compounds are included, but only a little gallic and ellagic acid. Toasting changed the chromatographic profiles of extracts spectacularly. Thus, the toasted acacia wood contributed flavonoids and condensed tannins (prorobinetin type) in inverse proportion to toasting intensity, while LMW phenolic compounds were directly proportional to toasting intensity, except for gallic and ellagic acid and related compounds. Even though toasting reduced differences between oak and acacia, particular characteristics of this wood must be taken into account when considering its use in cooperage: the presence of flavonoids and compounds with β-resorcylic structure and the absence of hydrolyzable tannins.

  15. 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

  16. Phenolic compounds and biological activity of Kitaibelia vitifolia.

    PubMed

    Mašković, Pavle; Solujić, Slavica; Mihailović, Vladimir; Mladenović, Milan; Cvijović, Milica; Mladenović, Jelena; Aćamović-Đoković, Gordana; Kurćubić, Vladimir

    2011-12-01

    This study was aimed at evaluating the antioxidant activity and efficacy of the ethanolic extract of the endemic plant species Kitaibelia vitifolia in inhibiting the growth of selected fungi and bacteria. Antimicrobial activity was tested using the broth dilution procedure for determination of minimum inhibitory concentration (MIC). MICs were determined for eight selected indicator strains. The highest susceptibility to K. vitifolia ethanolic extract among the bacteria tested was exhibited by Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 25923, and Klebsiella pneumoniae ATCC 13883 (MIC=15.62 μg/mL), followed by Escherichia coli ATCC 25922 and Proteus mirabilis ATCC 14153 (MIC=31.25 μg/mL), and Proteus vulgaris ATCC 13315 (MIC=62.50 μg/mL). Of the fungi, Candida albicans ATCC 10231 (MIC=15.62 μg/mL) showed the highest susceptibility, and Aspergillus niger ATCC 16404 (MIC=31.25 μg/mL) had the lowest. Results showed that K. vitifolia extract possesses antioxidant activity, with total antioxidant capacity of 75.45±0.68 μg of ascorbic acid/g and 50% inhibition concentration values of 47.45±0.55 μg/mL for 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity, 35.35±0.68 μg/mL for inhibitory activity against lipid peroxidation, 95.25±0.52 μg/mL for hydroxyl radical scavenging activity, and 31.50±0.35 μg/mL for metal chelating activity. Total phenolics, flavonoids, condensed tannins, and gallotannins were 85.25±0.69 mg of gallic acid (GA)/g, 45.32±0.55 mg of rutin/g, 54.25±0.75 mg of GA/g, and 41.74±0.55 mg of GA/g, respectively. The phenolic composition of K. vitifolia extract was determined by high-performance liquid chromatography. Rosmarinic acid was found to be the dominant phenolic compound of the extract.

  17. Biological activities of phenolic compounds present in virgin olive oil.

    PubMed

    Cicerale, Sara; Lucas, Lisa; Keast, Russell

    2010-02-02

    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.

  18. 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.

  19. 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.

  20. 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.

  1. A review of phenolic compounds in oil-bearing plants: Distribution, identification and occurrence of phenolic compounds.

    PubMed

    Alu'datt, Muhammad H; Rababah, Taha; Alhamad, Mohammad N; Al-Mahasneh, Majdi A; Almajwal, Ali; Gammoh, Sana; Ereifej, Khalil; Johargy, Ayman; Alli, Inteaz

    2017-03-01

    Over the last two decades, separation, identification and measurement of the total and individual content of phenolic compounds has been widely investigated. Recently, the presence of a wide range of phenolic compounds in oil-bearing plants has been shown to contribute to their therapeutic properties, including anti-cancer, anti-viral, anti-oxidant, hypoglycemic, hypo-lipidemic, and anti-inflammatory activities. Phenolics in oil-bearing plants are now recognized as important minor food components due to several organoleptic and health properties, and they are used as food or sources of food ingredients. Variations in the content of phenolics in oil-bearing plants have largely been attributed to several factors, including the cultivation, time of harvest and soil types. A number of authors have suggested that the presence phenolics in extracted proteins, carbohydrates and oils may contribute to objectionable off flavors The objective of this study was to review the distribution, identification and occurrence of free and bound phenolic compounds in oil-bearing plants.

  2. Total phenolics, phenolic acids, isoflavones, and anthocyanins and antioxidant properties of yellow and black soybeans as affected by thermal processing.

    PubMed

    Xu, Baojun; Chang, Sam K C

    2008-08-27

    The effects of boiling and steaming processes on the phenolic components and antioxidant activities of whole yellow (with yellow seed coat and yellow cotyledon) and black (with black seed coat and green cotyledon) soybeans were investigated. As compared to the raw soybeans, 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) in black soybeans. Pressure steaming caused significant (p < 0.05) increases in TPC, CTC, DPPH, FRAP, and ORAC in yellow soybeans. The steaming resulted in a greater retention of TPC, DPPH, FRAP, and ORAC values in both yellow and black soybeans as compared to the boiling treatments. To further investigate the effect of processing on phenolic compounds and elucidate the contribution of these compounds to changes of antioxidant activities, phenolic acids, isoflavones, and anthocyanins were quantitatively determined by HPLC. The pressure steaming treatments caused significant (p < 0.05) increases in gallic acid and 2,3,4-trihydroxybenzoic acid, whereas all treatments caused significant (p < 0.05) decreases in two predominant phenolic acids (chlorogenic acid and trans-cinnamic acid), and total phenolic acids for both yellow and black soybeans. All thermal processing caused significant (p < 0.05) increases in aglucones and beta-glucosides of isoflavones, but caused significant (p < 0.05) decreases in malonylglucosides of isoflavones for both yellow and black soybeans. All thermal processing caused significant (p < 0.05) decreases of cyanidin-3-glucoside and peonidin-3-glucoside in black soybeans. Significant correlations existed between selected phenolic compositions, isoflavone and anthocyanin contents, and antioxidant properties of cooked soybeans.

  3. 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.

  4. Phenolic acids act as signaling molecules in plant-microbe symbioses

    PubMed Central

    Mandal, Santi M; Chakraborty, Dipjyoti

    2010-01-01

    Phenolic acids are the main polyphenols made by plants. These compounds have diverse functions and are immensely important in plant-microbe interactions/symbiosis. Phenolic compounds act as signaling molecules in the initiation of legumerhizobia symbioses, establishment of arbuscular mycorrhizal symbioses and can act as agents in plant defense. Flavonoids are a diverse class of polyphenolic compounds that have received considerable attention as signaling molecules involved in plant-microbe interactions compared to the more widely distributed, simple phenolic acids; hydroxybenzoic and hydroxycinnamic acids, which are both derived from the general phenylpropanoid pathway. This review describes the well-known roles attributed to phenolic compounds as nod gene inducers of legume-rhizobia symbioses, their roles in induction of the GmGin1 gene in fungus for establishment of arbuscular mycorrhizal symbiosis, their roles in inducing vir gene expression in Agrobacterium, and their roles as defense molecules operating against soil borne pathogens that could have great implications for rhizospheric microbial ecology. Amongst plant phenolics we have a lack of knowledge concerning the roles of phenolic acids as signaling molecules beyond the relatively well-defined roles of flavonoids. This may be addressed through the use of plant mutants defective in phenolic acids biosynthesis or knock down target genes in future investigations. PMID:20400851

  5. 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

    2007-04-25

    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.

  6. Antioxidative activities and phenolic compounds of pumpkin (Cucurbita pepo) seeds and amaranth (Amaranthus caudatus) grain extracts.

    PubMed

    Peiretti, Pier Giorgio; Meineri, Giorgia; Gai, Francesco; Longato, Erica; Amarowicz, Ryszard

    2017-01-23

    Phenolic compounds were extracted from pumpkin (Cucurbita pepo) seed and amaranth (Amaranthus caudatus) grain into 80% (v/v) methanol. The extracts obtained were characterised by the contents of total phenolic compounds (TPC), trolox equivalent antioxidant capacity (TEAC), ferric-reducing antioxidant power (FRAP) and antiradical activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH(·)) radical. The content of individual phenolic compounds was determined by HPLC-DAD method. Pumpkin seeds showed the higher content of TPC than that from amaranth. The TEAC values of both extracts were similar each other. The lower value of FRAP was observed for pumpkin seed. Phenolic compound present in amaranth grain exhibited strongest antiradical properties against DPPH radical. Several peaks were present on the HPLC chromatograms of two extracts. The UV-DAD spectra confirmed the presence of vanillic acid derivatives in the amaranth grain. The three main phenolic compound present in pumpkin seed were characterised by UV-DAD spectra with maximum at 258, 266 and 278 nm.

  7. 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.

  8. 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.

  9. Ultrasound-Assisted Extraction of Total Phenolic Compounds from Inula helenium

    PubMed Central

    Wang, Jin; Zhao, Yong-Ming; Tian, Ya-Ting; Yan, Chun-Lin; Guo, Chun-Yan

    2013-01-01

    Ultrasound-assisted extraction (UAE) of phenolic compounds from Inula helenium was studied. Effects of ethanol concentration, ultrasonic time, solid-liquid ratio, and number of extractions were investigated. An orthogonal array was constructed to optimize UAE process. The optimized extraction conditions were as follows: ethanol concentration, 30%; solid-liquid ratio, 1 : 20; number of extractions, 2 times; extraction time, 30 min. Under the optimal conditions, the yield of total phenolic compounds and chlorogenic acid was 6.13 ± 0.58 and 1.32 ± 0.17 mg/g, respectively. The results showed that high amounts of phenolic compounds can be extracted from I. helenium by ultrasound-assisted extraction technology. PMID:24089600

  10. 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.

  11. Determination of some phenolic compounds in red wine by RP-HPLC: method development and validation.

    PubMed

    Burin, Vívian Maria; Arcari, Stefany Grützmann; Costa, Léa Luzia Freitas; Bordignon-Luiz, Marilde T

    2011-09-01

    A methodology employing reversed-phase high-performance liquid chromatography (RP-HPLC) was developed and validated for simultaneous determination of five phenolic compounds in red wine. The chromatographic separation was carried out in a C(18) column with water acidify with acetic acid (pH 2.6) (solvent A) and 20% solvent A and 80% acetonitrile (solvent B) as the mobile phase. The validation parameters included: selectivity, linearity, range, limits of detection and quantitation, precision and accuracy, using an internal standard. All calibration curves were linear (R(2) > 0.999) within the range, and good precision (RSD < 2.6%) and recovery (80-120%) was obtained for all compounds. This method was applied to quantify phenolics in red wine samples from Santa Catarina State, Brazil, and good separation peaks for phenolic compounds in these wines were observed.

  12. Determination of phenolic compounds using spectral and color transitions of rhodium nanoparticles.

    PubMed

    Gatselou, Vasiliki; Christodouleas, Dionysios C; Kouloumpis, Antonios; Gournis, Dimitrios; Giokas, Dimosthenis L

    2016-08-17

    This work reports a new approach for the determination of phenolic compounds based on their interaction with citrate-capped rhodium nanoparticles. Phenolic compounds (i.e., catechins, gallates, cinnamates, and dihydroxybenzoic acids) were found to cause changes in the size and localized surface plasmon resonance of rhodium nanoparticles, and therefore, give rise to analyte-specific spectral and color transitions in the rhodium nanoparticle suspensions. Upon reaction with phenolic compounds (mainly dithydroxybenzoate derivatives, and trihydroxybenzoate derivatives), new absorbance peaks at 350 nm and 450 nm were observed. Upon reaction with trihydroxybenzoate derivatives, however, an additional absorbance peak at 580 nm was observed facilitating the speciation of phenolic compounds in the sample. Both absorbance peaks at 450 nm and 580 nm increased with increasing concentration of phenolic compounds over a linear range of 0-500 μM. Detection limits at the mid-micromolar levels were achieved, depending on the phenolic compound involved, and with satisfactory reproducibility (<7.3%). On the basis of these findings, two rhodium nanoparticles-based assays for the determination of the total phenolic content and total catechin content were developed and applied in tea samples. The obtained results correlated favorably with commonly used methods (i.e., Folin-Ciocalteu and aluminum complexation assay). Not the least, the finding that rhodium nanoparticles can react with analytes and exhibit unique localized surface plasmon resonance bands in the visible region, can open new opportunities for developing new optical and sensing analytical applications.

  13. 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.

  14. 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.

  15. 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.

  16. 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.

  17. Analysis of twenty phenolic compounds in human urine: hydrochloric acid hydrolysis, solid-phase extraction based on K2CO 3-treated silica, and gas chromatography tandem mass spectrometry.

    PubMed

    Lu, Dasheng; Feng, Chao; Wang, Dongli; Lin, Yuanjie; Ip, Ho Sai Simon; She, Jianwen; Xu, Qian; Wu, Chunhua; Wang, Guoquan; Zhou, Zhijun

    2015-05-01

    This study developed a new method for the analysis of 20 phenolic compounds in human urine. The urine samples were prepared by hydrochloric acid (HCl) hydrolysis, liquid-liquid extraction (LLE), and solid-phase extraction (SPE) cleanup. We found that HCl hydrolysis is of similar effectiveness to, and much cheaper than, the traditional enzymatic method. Vanillic acid was co-eluted with butyl paraben and interfered with the determination of butyl paraben in urine. K2CO3-treated-silica-gel SPE was designed to efficiently eliminate interference from the endogenous organic acids (especially vanillic acid) in urine. After derivatization, the samples were analyzed by large-volume-injection gas chromatography-tandem mass spectrometry (LVI-GC-MS-MS). Good linearity (R (2) ≥ 0.996) was established in the range 0.1-100 ng mL(-1) for all analytes. Method detection limits (MDLs) were 0.7-9.8 pg mL(-1). Intraday (n = 5) and interday (n = 5 days) validation was performed, with satisfactory accuracy (recovery: 70-126 % and 73-107 %, respectively) and precision (RSD ≤ 19 %) at two levels (low: 0.1 and 0.5 ng mL(-1); high: 5 and 10 ng mL(-1)). The method was used in a population study and achieved more than 85 % detection for most analytes; mean analyte concentrations were in the range 0.01-185 ng mL(-1). The method is suitable for the analysis of multiple phenolic metabolites in human urine.

  18. Patterns of phenolic compounds in leafy galls of tobacco.

    PubMed

    Vereecke, D; Messens, E; Klarskov, K; De Bruyn, A; Van Montagu, M; Goethals, K

    1997-03-01

    The chemical composition of ethanolic and aqueous extracts from leafy galls produced after infection of Nicotiana tabacum L. plants with Rhodococcus fascians was drastically changed compared to uninfected controls. Chlorogenic acid was abundant both in uninfected and infected plants, but caffeic acid and another cinnamoyl analogue were new in leafy galls. The most pronounced product induced in leafy galls was identified as 7-O-methyl-6-O-beta-D-glucopyranosyl coumarin (7-methyl esculin). This is the first report of the presence of this coumarin derivative in tobacco. Interestingly, 7-methyl esculin did not accumulate in the presence of avirulent R. fascians strains nor was it found in leafy galls on other plant species. However, it did appear in crown galls induced by Agrobacterium tumefaciens on tobacco plants. Intriguingly, none of the phenolics known to accumulate in Solanaceae under pathogen attack were found in leafy galls. 7-Methyl esculin barely affected growth of R. fascians nor was it catabolized. Microscopical analysis showed that autofluorescent compounds were located mainly in the abundant meristematic regions of the leafy galls. We postulate that 7-methyl esculin might locally influence plant cell division.

  19. 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

  20. 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...

  1. A review of molecular mechanisms of the anti-leukemic effects of phenolic compounds in honey.

    PubMed

    Abubakar, Murtala B; Abdullah, Wan Zaidah; Sulaiman, Siti Amrah; Suen, Ang Boon

    2012-11-15

    Hematologic malignancies constitute about 9% of all new cases of cancers as reported via the GLOBOCAN series by International Agency for Research on Cancer (IARC) in 2008. So far, the conventional therapeutic and surgical approaches to cancer therapy have not been able to curtail the rising incidence of cancers, including hematological malignancies, worldwide. The last decade has witnessed great research interest in biological activities of phenolic compounds that include anticancer, anti-oxidation and anti-inflammation, among other things. A large number of anticancer agents combat cancer through cell cycle arrest, induction of apoptosis and differentiation, as well as through inhibition of cell growth and proliferation, or a combination of two or more of these mechanisms. Various phenolic compounds from different sources have been reported to be promising anticancer agents by acting through one of these mechanisms. Honey, which has a long history of human consumption both for medicinal and nutritional uses, contains a variety of phenolic compounds such as flavonoids, phenolic acids, coumarins and tannins. This paper presents a review on the molecular mechanisms of the anti-leukemic activity of various phenolic compounds on cell cycle, cell growth and proliferation and apoptosis, and it advocates that more studies should be conducted to determine the potential role of honey in both chemoprevention and chemotherapy in leukemia.

  2. Grapevine phenolic compounds in xylem sap and tissues are significantly altered during infection by Xylella fastidiosa.

    PubMed

    Wallis, Christopher M; Chen, Jianchi

    2012-09-01

    Pierce's disease of grapevine (PD), caused by the bacterial pathogen Xylella fastidiosa, remains a serious problem for grape production in California and elsewhere. This research examined induction of phenolic compounds in grapevines ('Thompson Seedless') infected with X. fastidiosa over a 6-month period. Two months postinoculation with X. fastidiosa, catechin, digalloylquinic acid, and astringin were found at greater levels in xylem sap; multiple catechins, procyanidins, and stilbenoids were found at greater levels in xylem tissues; and precursors to lignin and condensed tannins were found at greater levels in xylem cell walls. However, such large-scale inductions of phenolic compounds were not observed 4 months after inoculation. Six months after inoculation, infected plants had significantly reduced phenolic levels in xylem sap and tissues when compared with control plants, including lowered levels of lignin and condensed tannins. At 6 months, PD symptoms were severe in infected plants and most photosynthetic tissue was abscised. These results suggest that, even though grapevine hosts may initially respond to X. fastidiosa infections with increased production of phenolic compounds, ultimately, PD causes grapevines to enter a state of decline whereby diseased hosts no longer have the resources to support secondary metabolite production, including defense-associated phenolic compounds.

  3. 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.

  4. Three new phenolic compounds from the roots of Glycyrrhiza yunnanensis.

    PubMed

    Wang, Qing; Ji, Shuai; Yu, Si-wang; Wang, Hui-xia; Lin, Xiong-hao; Ma, Tao-tao; Qiao, Xue; Xiang, Cheng; Ye, Min; Guo, De-an

    2013-03-01

    Three new phenolic compounds (1-3), together with 16 known compounds (4-19), were isolated from the roots of Glycyrrhiza yunnanensis Cheng f. et L. K. Dai. On the basis of 1D and 2D NMR, HR-ESI-MS, and circular dichroism (CD) spectroscopic analysis, structures of the new compounds were elucidated as 2-(2'-methoxy-4'-hydroxy)-aryl-3-methy-6-hydroxy-benzofuran (1), (2S)-6,7-(2,2-dimethyldihydropyrano)-8-prenyl-4'-hydroxyflavanone (2), and 6-prenyl-7,3',4'-trihydroxyflavone (3). Compounds 1, 3, 5, 12, 14, 15 and 16 showed antioxidant activity by an ABTS-based assay.

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

    PubMed

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

    2013-12-20

    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.

  6. 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

  7. Factors influencing phenolic compounds in table olives (Olea europaea).

    PubMed

    Charoenprasert, Suthawan; Mitchell, Alyson

    2012-07-25

    The Mediterranean diet appears to be associated with a reduced risk of several chronic diseases including cancer and cardiovascular and Alzheimer's diseases. Olive products (mainly olive oil and table olives) are important components of the Mediterranean diet. Olives contain a range of phenolic compounds; these natural antioxidants may contribute to the prevention of these chronic conditions. Consequently, the consumption of table olives and olive oil continues to increase worldwide by health-conscious consumers. There are numerous factors that can affect the phenolics in table olives including the cultivar, degree of ripening, and, importantly, the methods used for curing and processing table olives. The predominant phenolic compound found in fresh olive is the bitter secoiridoid oleuropein. Table olive processing decreases levels of oleuropein with concomitant increases in the hydrolysis products hydroxytyrosol and tyrosol. Many of the health benefits reported for olives are thought to be associated with the levels of hydroxytyrosol. Herein the pre- and post-harvest factors influencing the phenolics in olives, debittering methods, and health benefits of phenolics in table olives are reviewed.

  8. Chemical Characterization of Secondary Organic Aerosol Formed from Atmospheric Aqueous-phase Reactions of Phenolic Compounds

    NASA Astrophysics Data System (ADS)

    Yu, L.; Smith, J.; Anastasio, C.; Zhang, Q.

    2012-12-01

    Phenolic compounds, which are released in significant amounts from biomass burning, may undergo fast aqueous-phase reactions to form secondary organic aerosol (SOA) in the atmosphere. Understanding the aqueous-phase reaction mechanisms of these compounds and the composition of their reaction products is thus important for constraining SOA sources and predicting organic aerosol properties in models. In this study, we investigate the aqueous-phase reactions of three phenols (phenol, guaiacol and syringol) with two oxidants - excited triplet states (3C*) of non-phenolic aromatic carbonyls and hydroxyl radical (OH). By employing four analytical methods including high-resolution aerosol mass spectrometry, total organic carbon analysis, ion chromatography, and liquid chromatography-mass spectrometry, we thoroughly characterize the chemical compositions of the low volatility reaction products of phenols and propose formation mechanisms based on this information. Our results indicate that phenolic SOA is highly oxygenated, with O/C ratios in the range of 0.83-1.03, and that the SOA of phenol is usually more oxidized than those of guaiacol and syringol. Among the three precursors, syringol generates the largest fraction of higher molecular weight (MW) products. For the same precursor, the SOA formed via reaction with 3C* is less oxidized than that formed via reaction with OH. In addition, oxidation by 3C* enhances the formation of higher MW species, including phenolic dimers, higher oligomers and hydroxylated products, compared to reactions initiated by OH, which appear to favor the formation of organic acids. However, our results indicate that the yields of small organic acids (e.g., formate, acetate, oxalate, and malate) are low for both reaction pathways, together accounting for less than 5% of total SOA mass.

  9. Major Phenolic Compounds, Antioxidant Capacity and Antidiabetic Potential of Rice Bean (Vigna umbellata L.) in China

    PubMed Central

    Yao, Yang; Cheng, Xu-Zhen; Wang, Li-Xia; Wang, Su-Hua; Ren, Guixing

    2012-01-01

    Interest in edible beans as nutraceuticals is increasing. In the present study, the individual phenolic acids, the total phenolic content (TPC), the total flavonoid content (TFC), and the antioxidant and antidiabetic potential of 13 varieties of rice beans from China were investigated. Eight phenolic compounds (catechin, epicatechin, p-coumaric acid, ferulic acid, vitexin, isovitexin, sinapic acid, quercetin) were analyzed on an ultra-performance liquid chromatography (UPLC) mass spectrometry (MS) system. The rice bean varieties had significant differences in total phenolic compounds (ranging from 123.09 ± 10.35 to 843.75 ± 30.15 μg/g), in TPC (ranging from 3.27 ± 0.04 to 6.43 ± 0.25 mg gallic acid equivalents (GAE)/g), in TFC (ranging from 55.95 ± 11.16 to 320.39 ± 31.77 mg catechin (CE)/g), in antioxidant activity (ranging from 39.87 ± 1.37 to 46.40 ± 2.18 μM·TE/g), in α-glucosidase inhibition activity (ranging from 44.32 ± 2.12 to 68.71 ± 2.19) and in advanced glycation end products formation inhibition activity (ranging from 34.11 ± 0.59 to 75.75 ± 0.33). This study is the first report on phytochemistry and biological activities in rice beans. PMID:22489119

  10. 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.

  11. 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

  12. 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

    2010-09-08

    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.

  13. 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.

  14. 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.

  15. New Isoprenylated Phenolic Compounds from Morus laevigata.

    PubMed

    Wang, Meng; Yu, Bang-Wei; Yu, Mei-Hua; Gao, Li-Xin; Li, Jing-Ya; Wang, He-Yao; Li, Jia; Hou, Ai-Jun

    2015-06-01

    Two new isoprenylated flavonoids, laevigasins A and B (1 and 2, resp.), and one new isoprenylated 2-arylbenzofuran, leavigasin C (3), together with eight known compounds, 4-11, were isolated from the twigs of Morus laevigata. Their structures were elucidated by spectroscopic methods. Laevigasin A (1) showed significant inhibitory effect on α-glucosidase in vitro. Notabilisin E (5), taxifolin (10), and hultenin (11) inhibited PTP1B phosphatase activity in vitro.

  16. Altitudinal and seasonal changes of phenolic compounds in Buxus sempervirens leaves and cuticles.

    PubMed

    Bernal, M; Llorens, L; Julkunen-Tiitto, R; Badosa, J; Verdaguer, D

    2013-09-01

    The variation in the leaf content of phenolic compounds has been related to the UV-B changes of the environment in which plants grow. In this context, we aimed to investigate: a) whether the seasonal and altitudinal changes in the content of phenolic compounds of Buxus sempervirens L. leaves and cuticles could be related to the natural fluctuations in UV-B levels and b) the possible use of specific phenolic compounds as biomarkers of ambient UV-B levels. To achieve these goals we sampled, every three months during one year, leaves of B. sempervirens along an altitudinal gradient. At the lowest and the highest altitudes, we also conducted a UV-exclusion experiment to discern whether the observed changes could be attributed to the natural variation in UV-B. Results show that total phenolic content of leaves was lower in June than in the other sampling dates, which suggests a leaf ontogenic rather than a UV-B effect on the leaf content of these compounds. Regarding the elevational gradient, the overall amount of phenolic acids and neolignan of entire leaves increased with altitude while the total amount of flavonoids in leaf cuticles decreased. However, the lack of a significant effect of our UV-exclusion treatment on the content of these compounds suggests that the observed variations along the altitudinal gradient would respond to other factors rather than to UV-B. Concomitantly, we did not find any phenolic compound in leaves or cuticles of B. sempervirens that could be considered as a biomarker of ambient UV-B levels.

  17. 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.

  18. Characterization and quantification of phenolic compounds in four tomato (Lycopersicon esculentum L.) farmers' varieties in northeastern Portugal homegardens.

    PubMed

    Barros, Lillian; Dueñas, Montserrat; Pinela, José; Carvalho, Ana Maria; Buelga, Celestino Santos; Ferreira, Isabel C F R

    2012-09-01

    Tomato (Lycopersicon esculentum L.) is one of the most widely consumed fresh and processed vegetables in the world, and contains bioactive key components. Phenolic compounds are one of those components and, according to the present study, farmers' varieties of tomato cultivated in homegardens from the northeastern Portuguese region are a source of phenolic compounds, mainly phenolic acid derivatives. Using HPLC-DAD-ESI/MS, it was concluded that a cis p-coumaric acid derivative was the most abundant compound in yellow (Amarelo) and round (Batateiro) tomato varieties, while 4-O-caffeolyquinic acid was the most abundant in long (Comprido) and heart (Coração) varieties. The most abundant flavonoid was quercetin pentosylrutinoside in the four tomato varieties. Yellow tomato presented the highest levels of phenolic compounds (54.23 μg/g fw), including phenolic acids (43.30 μg/g fw) and flavonoids (10.93 μg/g fw). The phenolic compounds profile obtained for the studied varieties is different from other tomato varieties available in different countries, which is certainly related to genetic features, cultivation conditions, and handling and storage methods associated to each sample.

  19. 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

    2012-05-09

    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.

  20. Analysis of phenolic compounds in commercial dried grape pomace by high-performance liquid chromatography electrospray ionization mass spectrometry.

    PubMed

    Ramirez-Lopez, Lina M; DeWitt, Christina A M

    2014-09-01

    By-products obtained from winemaking processes still contain large amounts of phenolic compounds, especially phenolic acids, flavanols, flavonols, stilbenes, and flavonoids. Enzymatic hydrolysis was used for determination and characterization of phenolic acids, flavanols, flavonols, and stilbenes. Characterization of the flavonoids was achieved using acid hydrolysis with 0.1% hydrochloric acid. In addition, organic solvents as 50% methanol, 70% methanol, 50% acetone, 0.01% pectinase, and 100% petroleum ether were also evaluated. Reversed phase high-performance liquid chromatography (RP-HPLC) with diode array detector was used to identify phenolic compounds. Internal standard quantification was implemented using a five points of the UV-visible absorption data collected at the wavelength of maximum absorbance. A total of 16 phenolic compounds were determined. The content differed from 1.19 to 1124 mg kg(-1). Outcomes from HPLC study showed that gallic acid, (+) catechin hydrate, and (-) epicatechin gallate were the major phenolic compounds presented in the sample. Malvidin and pelargonidin 3-O-glucoside were the major anthocyanins monoglucosides.

  1. 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.

  2. 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.

  3. Biodegradation of dimethylphenols by bacteria with different ring-cleavage pathways of phenolic compounds.

    PubMed

    Viggor, Signe; Heinaru, Eeva; Loponen, Jyrki; Merimaa, Merike; Tenno, Toomas; Heinaru, Ain

    2002-01-01

    The biodegradation of 3,4, 2,4, 2,3, 2,6 and 3,5-dimethylphenol in combination with phenol and p-cresol by axenic and mixed cultures of bacteria was investigated. The strains, which degrade phenol and p-cresol through different catabolic pathways, were isolated from river water continuously polluted with phenolic compounds of leachate of oil shale semicoke ash heaps. The proper research of degradation of 2,4 and 3,4-dimethylphenol in multinutrient environments was performed. The degradation of phenolic compounds from mixtures indicated a flux of substrates into different catabolic pathways. Catechol 2,3-dioxygenase activity was induced by dimethylphenols in Pseudomonas mendocina PC1, where meta cleavage pathway was functional during the degradation of p-cresol. In the case of strains PC18 and PC24 of P. fluorescens, the degradation of p-cresol occurred via the protocatechuate ortho pathway and the key enzyme of this pathway, p-cresol methylhydroxylase, was also induced by dimethylphenols. 2,4 and 3,4-dimethylphenols were converted into the dead-end products 4-hydroxy-3-methylbenzoic acid and 4-hydroxy-2-methylbenzoic acid. In the degradation of 3,4-dimethylphenol, the transient accumulation of 4-hydroxy-2-methylbenzaldehyde repressed the consumption of phenol from substrate mixtures. A mixed culture of strains with different catabolic types made it possible to overcome the incompatibilities at degradation of studied substrate mixtures.

  4. The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health.

    PubMed

    Tripoli, Elisa; Giammanco, Marco; Tabacchi, Garden; Di Majo, Danila; Giammanco, Santo; La Guardia, Maurizio

    2005-06-01

    The Mediterranean diet is rich in vegetables, cereals, fruit, fish, milk, wine and olive oil and has salutary biological functions. Epidemiological studies have shown a lower incidence of atherosclerosis, cardiovascular diseases and certain kinds of cancer in the Mediterranean area. Olive oil is the main source of fat, and the Mediterranean diet's healthy effects can in particular be attributed not only to the high relationship between unsaturated and saturated fatty acids in olive oil but also to the antioxidant property of its phenolic compounds. The main phenolic compounds, hydroxytyrosol and oleuropein, which give extra-virgin olive oil its bitter, pungent taste, have powerful antioxidant activity both in vivo and in vitro. The present review focuses on recent works analysing the relationship between the structure of olive oil polyphenolic compounds and their antioxidant activity. These compounds' possible beneficial effects are due to their antioxidant activity, which is related to the development of atherosclerosis and cancer, and to anti-inflammatory and antimicrobial activity.

  5. 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.

  6. 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.

  7. Analysis of interaction of phenolic compounds with the cholecystokinin signaling pathway to explain effects on reducing food intake.

    PubMed

    Al Shukor, Nadin; Raes, Katleen; Van Camp, John; Smagghe, Guy

    2014-03-01

    Previous animal experiments demonstrated that phenolic compounds can reduce weight and food intake, but the exact mechanism(s) behind these effects remain unknown. For regulation of food intake, the cholecystokinin (CCK) hormone signaling pathway plays an important role as it induces satiety by binding on its specific receptor (CCK1R), hereby reducing food intake. In this study, we investigated the possible interactions of eight phenolic compounds of different classes (tannic acid, gallic acid, benzoic acid, hydroxybenzoic acid, protocatechuic acid, quercetin, kaempferol and resveratrol) with the CCK1R signaling pathway. As major results, the tested phenolic compounds could not activate the CCK1R in a specific cell-based bioassay. In contrast, we observed an anti-CCK1R activity. This antagonistic action might be explained by blocking of the functioning of the CCK1R receptor, although the exact mechanism of interaction remains unknown. For tannic acid, we also measured a sequestration activity of the CCK hormone in vitro. In conclusion, the reported activity of phenolic compounds against food intake and weight is not based on an activation of the CCK1R. Taking into account the complex regulation of food intake, further work is necessary to unravel other essential mechanisms involved to explain the reported effects of phenolic compounds against food intake.

  8. Metabolism of berry anthocyanins to phenolic acids in humans.

    PubMed

    Nurmi, Tarja; Mursu, Jaakko; Heinonen, Marina; Nurmi, Anna; Hiltunen, Raimo; Voutilainen, Sari

    2009-03-25

    We studied the metabolism of berry anthocyanins to phenolic acids in six human subjects by giving them bilberry-lingonberry puree with and without oat cereals. Puree + cereals contained 1435 micromol of anthocyanins and 339 micromol of phenolic acids. The urinary excretion of measured 18 phenolic acids increased 241 micromol during the 48 h follow-up after the puree + cereals supplementation. The excretion peak of dietary phenolic acids was observed at 4-6 h after the puree + cereals supplementation and 2 h earlier after the supplementation of the puree alone. Homovanillic and vanillic acids were the most abundant metabolites, and they were partly produced from anthocyanins. No gallic acid, a fragmentation product of delphinidin glycosides, was detected, and only a very low amount of malvidin glycosides was possibly metabolized to syringic acid. Although anthocyanins were partly fragmented to phenolic acids, still a large part of metabolites remained unknown.

  9. Antioxidant capacities of phenolic compounds and tocopherols from Tunisian pomegranate (Punica granatum) fruits.

    PubMed

    Elfalleh, Walid; Tlili, Nizar; Nasri, Nizar; Yahia, Yassine; Hannachi, Hédia; Chaira, Nizar; Ying, Ma; Ferchichi, Ali

    2011-01-01

    This article aims to determine the phenolic, tocopherol contents, and antioxidant capacities from fruits (juices, peels, and seed oils) of 6 Tunisian pomegranate ecotypes. Total anthocyanins were determined by a differential pH method. Hydrolyzable tannins were determined with potassium iodate. The tocopherol (α-tocopherol, γ-tocopherol, and δ-tocopherol) contents were, respectively, 165.77, 107.38, and 27.29 mg/100 g from dry seed. Four phenolic compounds were identified and quantified in pomegranate peel and pulp using the high-performance liquid chromatography/ultraviolet method: 2 hydroxybenzoic acids (gallic and ellagic acids) and 2 hydroxycinnamic acids (caffeic and p-coumaric acids). Juice, peel, and seed oil antioxidants were confirmed by ferric reducing antioxidant power (FRAP) and oxygen radical absorbance capacity (ORAC) methods. The highest values were recorded in peels with 25.63 mmol trolox equivalent/100 g and 22.08 mmol TE/100 g for FRAP and ORAC assay, respectively. Results showed that the antioxidant potency of pomegranate extracts was correlated with their phenolic compound content. In particular, the highest correlation was reported in peels. High correlations were also found between peel hydroxybenzoic acids and FRAP ORAC antioxidant capacities. Identified tocopherols seem to contribute in major part to the antioxidant activity of seed oil. The results implied that bioactive compounds from the peel might be potential resources for the development of antioxidant function dietary food.

  10. 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.

  11. [Inhibitory effects of Lantana camera and its contained phenolic compounds in Eichhornia crassipes growth].

    PubMed

    Yi, Zhen; Zhang, Maoxin; Ling, Bing; Xu, Di; Ye, Jingzhong

    2006-09-01

    This paper studied the effects of Lantana camera fresh leaves aqueous extract and its contained phenolic compounds on the growth and physiologic-biochemical indexes of Eichhornia crassipes. The results showed that this extract had obvious inhibitory effects on the growth and development of E. crassipes. When the concentration was higher than 30 g FW x L(-1), it could kill E. crassipes after 6 days treatment. A total of seven phenolic compounds in the abstract were identified by HPLC, which were salicylic acid, gentisic acid, beta-resorcylic acid , coumarin, ferulic acid, p-hydroxybenzoic acid and 6-methyl coumarin, with the concentrations being, 50.95, 13.46, 5.28, 3.36, 2.92, 2.19 and 0.34 mg x L(-1), respectively. The mixture of the seven compounds had the strongest inhibitory effect, followed by salicylic acid, 6-methyl coumarin, coumarin, and p-hydroxybenzoic acid, while the effects of beta-resorcylic acid and gentisic acid were not significant.

  12. 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.

  13. 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

    2016-09-24

    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).

  14. 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

  15. 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.

  16. Phenolic-compound-extraction systems for fruit and vegetable samples.

    PubMed

    Garcia-Salas, Patricia; Morales-Soto, Aranzazu; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto

    2010-12-03

    This paper reviews the phenolic-compound-extraction systems used to analyse fruit and vegetable samples over the last 10 years. Phenolic compounds are naturally occurring antioxidants, usually found in fruits and vegetables. Sample preparation for analytical studies is necessary to determine the polyphenolic composition in these matrices. The most widely used extraction system is liquid-liquid extraction (LLE), which is an inexpensive method since it involves the use of organic solvents, but it requires long extraction times, giving rise to possible extract degradation. Likewise, solid-phase extraction (SPE) can be used in liquid samples. Modern techniques, which have been replacing conventional ones, include: supercritical fluid extraction (SFE), pressurized liquid extraction (PLE), microwave-assisted extraction (MAE) and ultrasound-assisted extraction (UAE). These alternative techniques reduce considerably the use of solvents and accelerate the extraction process.

  17. Modulation of Strawberry/Cranberry Phenolic Compounds Glucuronidation by Co-Supplementation with Onion: Characterization of Phenolic Metabolites in Rat Plasma Using an Optimized μSPE-UHPLC-MS/MS Method.

    PubMed

    Dudonné, Stéphanie; Dubé, Pascal; Pilon, Geneviève; Marette, André; Jacques, Hélène; Weisnagel, John; Desjardins, Yves

    2014-03-26

    Plant phenolic compounds are suggested to exert pharmacological activities in regards to obesity and type-2 diabetes, but their mode of action is poorly understood due to a lack of information about their bioavailability. This work aimed to study the bioavailability of GlucoPhenol phenolic compounds, a strawberry-cranberry extracts blend, by characterizing plasma phenolic profile in obese rats. A comparison was performed by co-supplementation with an onion extract. Using an optimized μSPE-UHPLC-MS/MS method, 21 phenolic metabolites were characterized, mostly conjugated metabolites and microbial degradation products of the native phenolic compounds. Their kinetic profiles revealed either an intestinal or hepatic formation. Among identified metabolites, isorhamnetin glucuronide sulfate was found in greater amount in plasma. Three glucuronidated conjugates of strawberry-cranberry phenolic compounds, p-hydroxybenzoic acid glucuronide, catechins glucuronide, and methyl catechins glucuronide were found in higher quantities when GlucoPhenol was ingested together with onion extract (+252%, +279%, and +118% respectively), suggesting a possible induction of glucuronidation processes by quercetin. This work allowed the characterization of actual phenolic metabolites generated in vivo following a phenolic intake, the analysis of their kinetics and suggested a possible synergistic activity of phenolic compounds for improving bioavailability.

  18. 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.

  19. 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.

  20. 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

  1. 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

  2. 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.

  3. Comparative analysis of phenolic acids in mistletoe plants from various hosts.

    PubMed

    Luczkiewicz, M; Cisowski, W; Kaiser, P; Ochocka, R; Piotrowski, A

    2001-01-01

    Phenolic acids present in mistletoe plants collected from various hosts were analysed with the use of HPLC. The following numbers of compounds were found in the mistletoe plant material gathered from respective hosts: Sorbus aucuparia- 12 compounds; Acer plantanoides--14 compounds: Malus domestica, Pyrus communis and Populus nigra--13 compounds each; Quercus robur--15 compounds. Altogether 21 phenolic acids were chromatographically identified in the tested material. The compounds were either free or combined as esters or glycosides. Comparative chromatography revealed qualitative differences in the investigated compounds between the various plant materials. For example o-coumaric acid was only found in mistletoe hosted by Quercus robur. Digallic acid was only found in the plant material hosted by Acer plantanoides. Qualitative and quantitative composition of mistletoes hosted by Malus domestica and Pyrus communis showed considerable similarities as far as phenolic acids were concerned. Moreover. vanillic acid. absent in all other batches of plant material, seemed to be characteristic of the above mistletoes. Quantitative HPLC analysis demonstrated a considerable content of salicylic acid (39.55 mg%) in mistletoe hosted by Sorbus aucuparia. Apart from the above material, this compound was only present in small quantities in plants hosted by Populus nigra (15.63 mg%) and Quercus robur (2.63 mg%).

  4. 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.

  5. Photocatalytic ozonation of phenolic wastewaters: Syringic acid, tyrosol and gallic acid.

    PubMed

    Gimeno, Olga; Fernandez, Lidia A; Carbajo, Maria; Beltran, Fernando; Rivas, Javier

    2008-01-01

    The photocatalytic ozonation of a mixture of 3 phenols (gallic acid, tyrosol and syringic acid) has been conducted under different operating conditions. The individual adsorption of the phenol type compounds onto titanium dioxide (photocatalyst) has been first evaluated. Equilibrium conditions are attained in less than an hour while the isotherm curves reveal that adsorption intensity increases in order: syringic acid < tyrosol < gallic acid. When the photocatalytic ozonation is applied, an optimum in titanium dioxide concentration is experienced (1.5 g L(-1)). Direct comparison of the photocatalytic ozonation to other less sophisticated oxidation systems (i.e., single ozonation, catalytic ozonation, photo-ozonation, etc.) indicates a higher efficiency of the former in terms of ozone uptake.

  6. New multifunctional surfactants from natural phenolic acids.

    PubMed

    Centini, Marisanna; Rossato, Maria Sole; Sega, Alessandro; Buonocore, Anna; Stefanoni, Sara; Anselmi, Cecilia

    2012-01-11

    Several new multifunctional molecules derived from natural sources such as amino acids and hydroxycinnamic acids were synthesized. They exhibit various activities such as emulsifying, UV-protecting, and radical scavenging, thereby conforming to the latest requirements for cosmetic ingredients. The synthesis comprises only a few steps: (i) the amino acid, the acid groups of which are protected by esterification, is coupled with ferulic or caffeic acid; (ii) the p-hydroxyl group of the cinnamic derivative reacts with dodecyl bromide in the presence of potassium carbonate (the resulting compounds are highly lipophilic and tested as water/oil (W/O) emulsifiers); (iii) these molecules, by deprotonating the acid groups of the amino acids, with successive salification, are more hydrophilic, with stronger O/W emulsifying properties. The new multifunctional surfactants might prove useful for the treatment of multiple skin conditions, including loss of cellular antioxidants, damage from free radicals, damage from UV, and others.

  7. 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.

  8. 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

  9. 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

  10. Determination of phenolic compounds and their antioxidant activity in fruits and cereals.

    PubMed

    Stratil, P; Klejdus, B; Kubán, V

    2007-03-15

    Three methods, FCM (with Folin-Ciocalteu reagent), PBM (Price and Butler) and AAPM (with 4-aminoantipyrine) for assessment of phenolic compounds and three commonly used methods, TEAC (Trolox equivalent antioxidant capacity), DPPH (with diphenyl-picrylhydrazyl radical), and FRAP (ferric reducing antioxidant power) for evaluation of antioxidant capacity, were modified to a semimicroscale (total volume 1ml) with minimum consumption (to 100mul) of a sample and thereby applicable for fast screening. Appropriate standards and extracts of 17 kinds of fruit and six kinds of cereal were assessed for total content of phenolic compounds and total antioxidant capacity by each of these methods. The results of analyses of commonly used standards (gallic, caffeic and ferulic acids, (+)-catechin, Trolox, fenol and FeSO(4)) for these methods and identical plant extract showed different reactivity of principal reagent of the methods with individual standards and therefore with phenolic substances of extracts as well. However, the trends of the measured values of extracts could be compared, though their absolute values differ proportionally. At assessments of phenolic compounds it is important to determine content of ascorbic acid at roughly the same time and correct the obtained values according to its contribution to the increase in absorbance calculated on the basis of absorbance equations, especially for samples with a higher content. The same is true for reducing saccharides; they can significantly "elevate" values of contents of phenolic compounds and antioxidant activities (by even more than 50%), especially in samples of sweeter fruits. The saccharides should therefore be removed or a correction applied reflecting their concentration.

  11. 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.

  12. The chemical nature of phenolic compounds determines their toxicity and induces distinct physiological responses in Saccharomyces cerevisiae in lignocellulose hydrolysates

    PubMed Central

    2014-01-01

    We investigated the severity of the inhibitory effects of 13 phenolic compounds usually found in spruce hydrolysates (4-hydroxy-3-methoxycinnamaldehyde, homovanilyl alcohol, vanillin, syringic acid, vanillic acid, gallic acid, dihydroferulic acid, p-coumaric acid, hydroquinone, ferulic acid, homovanillic acid, 4-hydroxybenzoic acid and vanillylidenacetone). The effects of the selected compounds on cell growth, biomass yield and ethanol yield were studied and the toxic concentration threshold was defined for each compound. Using Ethanol Red, the popular industrial strain of Saccharomyces cerevisiae, we found the most toxic compound to be 4-hydroxy-3-methoxycinnamaldehyde which inhibited growth at a concentration of 1.8 mM. We also observed that toxicity did not generally follow a trend based on the aldehyde, acid, ketone or alcohol classification of phenolic compounds, but rather that other structural properties such as additional functional groups attached to the compound may determine its toxicity. Three distinctive growth patterns that effectively clustered all the compounds involved in the screening into three categories. We suggest that the compounds have different cellular targets, and that. We suggest that the compounds have different cellular targets and inhibitory mechanisms in the cells, also compounds who share similar pattern on cell growth may have similar inhibitory effect and mechanisms of inhibition. PMID:24949277

  13. The chemical nature of phenolic compounds determines their toxicity and induces distinct physiological responses in Saccharomyces cerevisiae in lignocellulose hydrolysates.

    PubMed

    Adeboye, Peter Temitope; Bettiga, Maurizio; Olsson, Lisbeth

    2014-01-01

    We investigated the severity of the inhibitory effects of 13 phenolic compounds usually found in spruce hydrolysates (4-hydroxy-3-methoxycinnamaldehyde, homovanilyl alcohol, vanillin, syringic acid, vanillic acid, gallic acid, dihydroferulic acid, p-coumaric acid, hydroquinone, ferulic acid, homovanillic acid, 4-hydroxybenzoic acid and vanillylidenacetone). The effects of the selected compounds on cell growth, biomass yield and ethanol yield were studied and the toxic concentration threshold was defined for each compound. Using Ethanol Red, the popular industrial strain of Saccharomyces cerevisiae, we found the most toxic compound to be 4-hydroxy-3-methoxycinnamaldehyde which inhibited growth at a concentration of 1.8 mM. We also observed that toxicity did not generally follow a trend based on the aldehyde, acid, ketone or alcohol classification of phenolic compounds, but rather that other structural properties such as additional functional groups attached to the compound may determine its toxicity. Three distinctive growth patterns that effectively clustered all the compounds involved in the screening into three categories. We suggest that the compounds have different cellular targets, and that. We suggest that the compounds have different cellular targets and inhibitory mechanisms in the cells, also compounds who share similar pattern on cell growth may have similar inhibitory effect and mechanisms of inhibition.

  14. 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

  15. Partition behavior of virgin olive oil phenolic compounds in oil-brine mixtures during thermal processing for fish canning.

    PubMed

    Sacchi, Raffaele; Paduano, Antonello; Fiore, Francesca; Della Medaglia, Dorotea; Ambrosino, Maria Luisa; Medina, Isabel

    2002-05-08

    The chemical modifications and partitioning toward the brine phase (5% salt) of major phenol compounds of extra virgin olive oil (EVOO) were studied in a model system formed by sealed cans filled with oil-brine mixtures (5:1, v/v) simulating canned-in-oil food systems. Filled cans were processed in an industrial plant using two sterilization conditions commonly used during fish canning. The partitioning of phenolic compounds toward brine induced by thermal processing was studied by reversed-phase high-performance liquid chromatographic analysis of the phenol fraction extracted from oils and brine. Hydroxytyrosol (1), tyrosol (2), and the complex phenolic compounds containing 1 and 2 (i.e., the dialdehydic form of decarboxymethyl oleuropein aglycon 3, the dialdehydic form of decarboxymethyl ligstroside aglycon 4, and the oleuropein aglycon 6) decreased in the oily phase after sterilization with a marked partitioning toward the brine phase. The increase of the total amount of 1 and 2 after processing, as well as the presence of elenolic acid 7 released in brine, revealed the hydrolysis of the ester bond of hydrolyzable phenolic compounds 3, 4, and 6 during thermal processing. Both phenomena (partitioning toward the water phase and hydrolysis) contribute to explain the loss of phenolic compounds exhibited by EVOO used as filling medium in canned foods, as well as the protection of n-3 polyunsaturated fatty acids in canned-in-EVOO fish products.

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

    PubMed

    Goufo, Piebiep; Trindade, Henrique

    2014-03-01

    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.

  17. 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

  18. 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

    2014-12-31

    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.

  19. Effect of meteorological parameters and regions on accumulation pattern of phenolic compounds in different mulberry cultivars grown in China.

    PubMed

    Yang, Jiufang; Zhang, Xiaoxu; Jin, Qing; Gu, Liwei; Liu, Xuanjun; Li, Jingming; Ni, Yuanying

    2017-05-01

    The compositions of phenolic compounds in 10 cultivars of two mulberry species (Morus atropurpurea Roxb. and Morus alba Linn.) grown in four regions of China were analysed using HPLC-TOF-MS. Results showed that a total of 27 phenolic compounds were identified in these mulberry cultivars. The Taiwan cultivar from the Jiangsu region showed the highest concentration of hydroxycinnamic acids, quercetin derivatives, and anthocyanins. Multivariate statistical analysis revealed that six mulberry cultivars grown in the region of Jiangsu, Ningxia, and Guangdong were differentiated regarding their species feature and regional characteristics. Cyanidin rhamnosylglucoside, 4-caffeoylquinic acid, dihydroquercetin, and quercetin were further screened out to be the key compounds for the differentiation of these cultivars. The correlation between the regional climate feature (including rainfall, humidity, and temperature) and the accumulation of phenolic compounds in these mulberry cultivars was established.

  20. 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.

  1. Composition and health effects of phenolic compounds in hawthorn (Crataegus spp.) of different origins.

    PubMed

    Yang, Baoru; Liu, Pengzhan

    2012-06-01

    Epicatechin, aglycons and glycosides of B-type oligomeric procyanidins and flavonols, phenolic acids and C-glycosyl flavones are the major groups of phenolic compounds in hawthorn (Crataegus spp). The total content of phenolic compounds is higher in the leaves and flowers than in the fruits. Procyanidins dominate in the fruits, whereas flavonol glycosides and C-glycosyl flavones are most abundant in the leaves. Genotype and developmental/ripening stage have strong impacts. Procyanidin glycosides and C-glycosyl flavones may be chemotaxonomic markers differentiating species and varieties of hawthorn. Future research shall improve the separation, identification and quantification of procyanidins with degree of polymerisation (DP) ≥ 6, procyanidin glycosides, C-glycosyl flavones and some flavonol glycosides. In vitro and animal studies have shown cardioprotective, hypolipidaemic, hypotensive, antioxidant, radical-scavenging and anti-inflammatory potentials of hawthorn extracts, suggesting different phenolic compounds as the major bioactive components. However, the varying and insufficiently defined composition of the extracts investigated, as a result of different raw materials and extraction methods, makes comparison of the studies very difficult. Clinical evidence indicates that some hawthorn extracts may increase the exercise tolerance of patients with congestive heart failure. More clinical studies are needed to establish the effects of hawthorn, especially in healthy humans.

  2. Towards green analysis of virgin olive oil phenolic compounds: Extraction by a natural deep eutectic solvent and direct spectrophotometric detection.

    PubMed

    Paradiso, Vito Michele; Clemente, Antonia; Summo, Carmine; Pasqualone, Antonella; Caponio, Francesco

    2016-12-01

    The determination of phenolic compounds in extra virgin olive oils (EVOO) by means of rapid, low-cost, environment-free methods would be a desirable achievement. A natural deep eutectic solvent (DES) based on glucose and lactic acid was considered as extraction solvent for phenolic compounds in EVOO. DESs are green solvents characterized by high availability, biodegradability, safety, and low cost. The spectrophotometric characteristics of DES extracts of 65 EVOO samples were related to the total phenolic content of the oils, assessed by methanol-water extraction coupled to the Folin-Ciocalteu assay. A regression model (ncalibration=45, nvalidation=20), including the absorbance at two wavelengths (257, 324nm), was obtained, with an adjusted R(2)=0.762. Therefore the DES could provide a promising and viable approach for a green screening method of phenolic compounds in EVOO, by means of simple spectrophotometric measurements of extracts, even for on-field analysis (for example in olive mills).

  3. Variation of anthocyanins and other major phenolic compounds throughout the ripening of four Portuguese blueberry (Vaccinium corymbosum L) cultivars.

    PubMed

    Silva, Sara; Costa, Eduardo M; Coelho, Marta C; Morais, Rui M; Pintado, Manuela E

    2017-01-01

    Blueberries are widely recognised as one of the richest sources of bioactive compounds, among which are anthocyanins, though the ripeness of berries has been reported as affecting the phytochemical composition of fruits. Therefore, the present work aimed to evaluate the variation of anthocyanins, and other major phenolics, throughout five ripening stages in four blueberry cultivars. The results showed that the antioxidant capacity and anthocyanin content increased during ripening, reaching the highest values when the blueberries are collected from bunches comprised of 75% ripe blueberries. Antagonistically, the amount of phenolic acid decreases, while the quercetin-3-glucoside levels remain stable. Furthermore, Goldtraube blueberries appear to possess, systematically, higher amounts of phenolic compounds than the other cultivars studied. Thus, when seeking the highest yield of anthocyanins, the preferred harvest should occur in bunches that contain ca 75% of ripe blueberries and, considering the cultivars assayed, the Goldtraube cultivar appears to be the richest in phenolic compounds.

  4. Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: characterization by high-performance liquid chromatography-diode array detection-electrospray tandem mass spectrometry.

    PubMed

    Magalhães, Paulo J; Vieira, Joana S; Gonçalves, Luís M; Pacheco, João G; Guido, Luís F; Barros, Aquiles A

    2010-05-07

    The aim of the present work was the development of a suitable methodology for the separation and determination of phenolic compounds in the hop plant. The developed methodology was based on the sample purification by adsorption of phenolic compounds from the matrix to polyvinylpolypyrrolidone (PVPP) and subsequent desorption of the adsorbed polyphenols with acetone/water (70:30, v/v). At last, the extract was analyzed by HPLC-DAD and HPLC-ESI-MS/MS. The first phase of this work consisted of the study of the adsorption behavior of several classes of phenolic compounds (e.g. phenolic acids, flavonols, and flavanols) by PVPP in model solutions. It has been observed that the process of adsorption of the different phenolic compounds to PVPP (at low concentrations) is differentiated, depending on the structure of the compound (number of OH groups, aromatic rings, and stereochemistry hindrance). For example, within the phenolic acids class (benzoic, p-hydroxybenzoic, protocatechuic and gallic acids) the PVPP adsorption increases with the number of OH groups of the phenolic compound. On the other hand, the derivatization of OH groups (methylation and glycosylation) resulted in a greatly diminished binding. The use of PVPP revealed to be very efficient for adsorption of several phenolic compounds such as catechin, epicatechin, xanthohumol and quercetin, since high adsorption and recovery values were obtained. The methodology was further applied for the extraction and isolation of phenolic compounds from hops. With this methodology, it was possible to obtain high adsorption values (>or=80%) and recovery yield values (>or=70%) for the most important phenolic compounds from hops such as xanthohumol, catechin, epicatechin, quercetin and kaempferol glycosides, and in addition it allows the identification of about 30 phenolic compounds by HPLC-DAD and HPLC-ESI-MS/MS.

  5. 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.

  6. Separation and characterization of phenolic compounds from dry-blanched peanut skins by liquid chromatography-electrospray ionization mass spectrometry.

    PubMed

    Ma, Yuanyuan; Kosińska-Cagnazzo, Agnieszka; Kerr, William L; Amarowicz, Ryszard; Swanson, Ruthann B; Pegg, Ronald B

    2014-08-22

    A large variety of phenolic compounds, including phenolic acids (hydroxybenzoic acids, hydroxycinnamic acids, and their esters), stilbenes (trans-resveratrol and trans-piceatannol), flavan-3-ols (e.g., (-)-epicatechin, (+)-catechin, and their polymers {the proanthocyanidins, PACs}), other flavonoids (e.g., isoflavones, flavanols, and flavones, etc.) and biflavonoids (e.g., morelloflavone), were identified in dry-blanched peanut skins (PS) by this study. High-performance liquid chromatography (HPLC) coupled with electrospray ionization mass spectrometry (ESI-MS(n)) was applied to separate and identify the phenolic constituents. Reversed-phase HPLC was employed to separate free phenolic compounds as well as PAC monomers, dimers, and trimers. PACs with a degree of polymerization (DP) of >4 were chromatographed via hydrophilic interaction liquid chromatography (HILIC). Tentative identification of the separated phenolics was based solely on molecular ions and MS(n) fragmentation patterns acquired by ESI-MS in the negative-ion mode. The connection sequence of PAC oligomers (DP <5) could be deduced mainly through characteristic quinone methide (QM) cleavage ions. When the DP reached 6, only a proportion of the flavan-3-ols could be ascertained in the PACs because of the extremely complicated fragmentation patterns involved. The identification of free phenolic acids, stilbenes, and flavonoids was achieved by authentic commercial standards and also by published literature data. Quantification was performed based on peak areas of the UV (free phenolic compounds) or fluorescence (PACs) signals from the HPLC chromatograms and calibration curves of commercial standards. Overall, PS contain significantly more PACs compared to free phenolic compounds.

  7. 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.

  8. An Overview of Plant Phenolic Compounds and Their Importance in Human Nutrition and Management of Type 2 Diabetes.

    PubMed

    Lin, Derong; Xiao, Mengshi; Zhao, Jingjing; Li, Zhuohao; Xing, Baoshan; Li, Xindan; Kong, Maozhu; Li, Liangyu; Zhang, Qing; Liu, Yaowen; Chen, Hong; Qin, Wen; Wu, Hejun; Chen, Saiyan

    2016-10-15

    In this paper, the biosynthesis process of phenolic compounds in plants is summarized, which include the shikimate, pentose phosphate and phenylpropanoid pathways. Plant phenolic compounds can act as antioxidants, structural polymers (lignin), attractants (flavonoids and carotenoids), UV screens (flavonoids), signal compounds (salicylic acid, flavonoids) and defense response chemicals (tannins, phytoalexins). From a human physiological standpoint, phenolic compounds are vital in defense responses, such as anti-aging, anti-inflammatory, antioxidant and anti-proliferative activities. Therefore, it is beneficial to eat such plant foods that have a high antioxidant compound content, which will cut down the incidence of certain chronic diseases, for instance diabetes, cancers and cardiovascular diseases, through the management of oxidative stress. Furthermore, berries and other fruits with low-amylase and high-glucosidase inhibitory activities could be thought of as candidate food items in the control of the early stages of hyperglycemia associated with type 2 diabetes.

  9. 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

  10. 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.

  11. 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

  12. 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.

  13. 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.

  14. Identification of phenolic compounds from lingonberry (Vaccinium vitis-idaea L.), bilberry (Vaccinium myrtillus L.) and hybrid bilberry (Vaccinium x intermedium Ruthe L.) leaves.

    PubMed

    Hokkanen, Juho; Mattila, Sampo; Jaakola, Laura; Pirttilä, Anna Maria; Tolonen, Ari

    2009-10-28

    Phenolic compounds from leaves of lingonberry (Vaccinium vitis-idaea L.), bilberry (Vaccinium myrtillus L.), and the natural hybrid of bilberry and lingonberry (Vaccinium x intermedium Ruthe L., hybrid bilberry) were identified using LC/TOF-MS and LC/MS/MS after extraction from the plant material in methanol in an ultrasonicator. The phenolic profiles in the plants were compared using the LC/TOF-MS responses. This is the first thorough report of phenolic compounds in hybrid bilberry. In total, 51 different phenolic compounds were identified, including flavan-3-ols, proanthocyanidins, flavonols and their glycosides, and various phenolic acid conjugates. Of the identified compounds, 35 were detected in bilberry, 36 in lingonberry, and 46 in the hybrid. To our knowledge, seven compounds were previously unreported in Vaccinium genus and many of the compounds are reported for the first time from bilberry and lingonberry.

  15. Study of low molecular weight phenolic compounds during the aging of sparkling wines manufactured with red and white grape varieties.

    PubMed

    Pozo-Bayón, M Angeles; Hernández, M Teresa; Martín-Alvarez, Pedro J; Polo, M Carmen

    2003-03-26

    Thirty-two phenolic compounds of low molecular weight were identified in 36 white, blanc de noir, and rosé sparkling wines by using HPLC with photodiode array and mass spectrometry detection. Some of the identified compounds, such as cis- and trans-ethylcaftaric, cis- and trans-ethylcaffeic, and cis- or trans-ethyl-p-coumaric acids, 2R,3R-dihydroquercetin, 2R,3R-dihydrokaempferol 3-O-beta-d-glucoside, and a lignan derivative are described for the first time in sparkling wines manufactured with grapes of red varieties. This is also the first time that cis- or trans-diethylfertaric acids have been identified in wines. When cluster analysis was applied to the data of 19 of the 32 identified compounds, the greatest differences found in the low molecular weight phenolic compounds in sparkling wines were due to the grape variety from which they were manufactured, whereas aging time did not significantly influence phenolic composition. Nine phenolic compounds, that is, trans-p-coumaric and trans-caftaric acids, trans-resveratrol glucoside, cis-coutaric, trans-coutaric, cis-p-coumaric, and cis-caftaric acids, tryptophol, and syringic acid, permit the wines to be classified correctly in accordance with the grape variety from which they were manufactured.

  16. 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.

  17. 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.

  18. Phenolic Compounds of Potato Peel Extracts: Their Antioxidant Activity and Protection against Human Enteric Viruses.

    PubMed

    Silva-BeltrÁn, Norma Patricia; Chaidez-Quiroz, Cristóbal; López-Cuevas, Osvaldo; Ruiz-Cruz, Saul; López-Mata, Marco A; Del-Toro-SÁnchez, Carmen Lizette; Marquez-Rios, Enrique; Ornelas-Paz, José de Jesús

    2017-02-28

    Potato peels (PP) contain several bioactive compounds. These compounds are known to provide human health benefits, including antioxidant and antimicrobial properties. In addition, these compounds could have effects on human enteric viruses that have not yet been reported. The objective of the present study was to evaluate the phenolic composition, antioxidant properties in the acidified ethanol extract (AEE) and water extract of PP, and the antiviral effects on the inhibition of Av-05 and MS2 bacteriophages, which were used as human enteric viral surrogates. The AEE showed the highest phenolic content and antioxidant activity. Chlorogenic and caffeic acids were the major phenolic acids. In vitro analysis indicated that PP had a strong antioxidant activity. A 3 h incubation with AEE at a concentration of 5 mg/ml was needed to reduce the PFU/ml (plaque-forming unit per unit volume) of Av-05 and MS2 by 2.8 and 3.9 log₁₀, respectively, in a dose-dependent manner. Our data suggest that PP has potential to be a source of natural antioxidants against enteric viruses.

  19. 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.

  20. Effects of different organic farming methods on the concentration of phenolic compounds in sea buckthorn leaves.

    PubMed

    Heinäaho, Merja; Pusenius, Jyrki; Julkunen-Tiitto, Riitta

    2006-10-04

    The effects of different cultivation methods on the amount of phenolic compounds in leaves of 1-year-old seedlings of two Finnish sea buckthorn (Hippophae rhamnoides L. ssp. rhamnoides) cultivars 'Terhi' and 'Tytti' were studied in a field experiment established at coastal area in Merikarvia, western Finland. The cultivation methods included different fertilizers (suitable for organic cultivation), mulches (organic and plastic), and land contours (flat vs low hill surface). Two experiments were conducted. The first allowed the estimation of the effects of cultivar, fertilizer, surface contour, and all their interactions, while the other allowed the estimation of the effects of mulches, land contours, and their interactions for the cultivar 'Tytti'. Eleven different hydrolyzable tannins, pentagalloylglucose, and 14 other phenolic compounds were detected by chemical analysis with high-performance liquid chromatography (HPLC). The amount of phenolic compounds varied between different land contours and mulches. The concentrations of gallic acid, pentagalloylglucose, quercetin-3-rhamnoside, monocoumaroyl astragalin A, total hydrolyzable tannins, and condensed tannins were significantly higher on the flat surface than on the low hill surface. The plastic mulch decreased the concentration of gallic acid, hydrolyzable tannins, and condensed tannins compared to the other mulches used. These results suggest ways to cultivate sea buckthorn to produce large amounts of valuable chemicals, especially tannins in the leaves.

  1. Phenolic compounds in hawthorn (Crataegus grayana) fruits and leaves and changes during fruit ripening.

    PubMed

    Liu, Pengzhan; Kallio, Heikki; Yang, Baoru

    2011-10-26

    Phenolics in the fruits and leaves of Crataegus grayana were identified by HPLC-UV-ESI-MS. The contents of these compounds and their changes during autumn were also analyzed. Epicatechin [1-7 mg/g dry mass (DM) in fruits and 1-10 mg/g DM in leaves), procyanidins B2 (2-4 and 1-8 mg/g DM) and C1 (2-4 and 1-8 mg/g DM), hyperoside (0.5-1 and 2-11 mg/g DM), and a quercetin-pentoside (0.3-0.5 and 2-6 mg/g DM) were the major phenolics in both fruits and leaves. C-Glycosyl flavones were present in leaves (2-5 mg/g DM), whereas only trace levels were found in fruits. Ideain and 5-O-caffeoylquinic acid were found only in fruits. An additional 11 phenolics were identified/tentatively identified. Total phenolic contents reached highest levels by the end of August in fruits and by the end of September in leaves. The compositional profiles of phenolics in fruits and leaves of C. grayana were different from those of other Crataegus species.

  2. Induction of phenolsulfotransferase expression by phenolic acids in human hepatoma HepG2 cells.

    PubMed

    Yeh, Chi-Tai; Huang, Shang-Ming; Yen, Gow-Chin

    2005-06-15

    Phenolic acids are antioxidant phenolic compounds, widespread in plant foods, which contribute significant biological and pharmacological properties; some have demonstrated a remarkable ability to alter sulfate conjugation. However, the modulation mechanisms of antioxidant phenolic acids on phenolsulfotransferase activity have not yet been described. In the present study, the human hepatoma cell line, HepG2, was used as a model to investigate the effect of antioxidant phenolic acids on enzymatic activity and expression of one of the major phase II sulfate conjugation enzymes, P-form phenolsulfotransferase (PST-P). The results showed that gallic acid, gentisic acid, p-hydroxybenzoic acid, and p-coumaric acid increased PST-P activity, in a dose-dependent manner. A maximum of 4- and 5-fold induction of PST-P activity was observed for both gallic acid and gentisic acid; however, they showed an adverse effect on cell growth at higher concentrations. A 2- or 2.5-fold increase of PST-P activity was found with either p-coumaric or p-hydroxybenzoic acid treatment, whereas no significant effect was found for ferulic acid treatment. PST-P induction, by gallic acid, was further confirmed, using reverse transcription PCR and Western blotting techniques to measure mRNA expression and protein translation. A significant correlation (r = 0.74, p < 0.01) between the expressions of PST-P mRNA and the corresponding PST-P activity was observed. Thus, gallic acid increased PST-P protein expression in HepG2 cells, in a dose- and time-dependent manner. The results demonstrated that certain antioxidant phenolic acids could induce PST-P activity in HepG2 cells, by promoting PST-P mRNA and protein expression, suggesting a novel mechanism by which phenolic acids may be implicated in phase II sulfate conjugation.

  3. Hydrocaffeic and p-coumaric acids, natural phenolic compounds, inhibit UV-B damage in WKD human conjunctival cells in vitro and rabbit eye in vivo.

    PubMed

    Larrosa, Mar; Lodovici, Maura; Morbidelli, Lucia; Dolara, Piero

    2008-10-01

    This paper studied the effect on UV-B ocular damage of 10microM hydrocaffeic acid (HCAF) alone and as a mixture (MIX) (5 microM HCAF+5 microM p-coumaric acid). Since ocular UV-B damage is mediated by reactive oxygen species, the aim was to test if HCAF and MIX could reduce oxidation damage in human conjunctival cells (WKD) in vitro and in cornea and sclera of rabbits in vivo. After UVB irradiation (44 J/m(2)) of WKD cells, 8-oxodG levels in DNA were markedly increased and this effect was attenuated by HCAF and MIX. Rabbit eyes were treated by application of HCAF and MIX drops before UV-B exposure (79 J/m(2)). Corneal and scleral DNA oxidation damage, xanthine-oxidase (XO) activity and malondialdehyde levels (MDA) in corneal tissue and prostaglandin E(2) (PGE(2)) in the aqueous humour were reduced by HCAF alone and in combination with p-coumaric acid, showing their potential as a topical treatment against UV-B damage.

  4. Metabolic and Microbial Modulation of the Large Intestine Ecosystem by Non-Absorbed Diet Phenolic Compounds: A Review.

    PubMed

    Mosele, Juana I; Macià, Alba; Motilva, Maria-José

    2015-09-18

    Phenolic compounds represent a diverse group of phytochemicals whose intake is associated with a wide spectrum of health benefits. As consequence of their low bioavailability, most of them reach the large intestine where, mediated by the action of local microbiota, a series of related microbial metabolites are accumulated. In the present review, gut microbial transformations of non-absorbed phenolic compounds are summarized. Several studies have reached a general consensus that unbalanced diets are associated with undesirable changes in gut metabolism that could be detrimental to intestinal health. In terms of explaining the possible effects of non-absorbed phenolic compounds, we have also gathered information regarded their influence on the local metabolism. For this purpose, a number of issues are discussed. Firstly, we consider the possible implications of phenolic compounds in the metabolism of colonic products, such as short chain fatty acids (SCFA), sterols (cholesterol and bile acids), and microbial products of non-absorbed proteins. Due to their being recognized as affective antioxidant and anti-inflammatory agents, the ability of phenolic compounds to counteract or suppress pro-oxidant and/or pro-inflammatory responses, triggered by bowel diseases, is also presented. The modulation of gut microbiota through dietetic maneuvers including phenolic compounds is also commented on. Although the available data seems to assume positive effects in terms of gut health protection, it is still insufficient for solid conclusions to be extracted, basically due to the lack of human trials to confirm the results obtained by the in vitro and animal studies. We consider that more emphasis should be focused on the study of phenolic compounds, particularly in their microbial metabolites, and their power to influence different aspects of gut health.

  5. 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.

  6. 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.

  7. Anti-platelet effects of different phenolic compounds from Yucca schidigera Roezl. bark.

    PubMed

    Olas, Beata; Wachowicz, Barbara; Stochmal, Anna; Oleszek, Wieslaw

    2002-05-01

    Resveratrol (3,4',5-trihydroxystilbene) has been reported to have a variety of anti-inflammatory, anti-carcinogenic, anti-fungal and anti-platelet effects. It occurs naturally in different medicinal plants. Recently, resveratrol and other related phenolic compounds including trans-3,3',5,5'-tetrahydroxy-4'-methoxystilbene and yuccaols A and C were isolated from the bark of Yucca schidigera. The aim of the present study was to evaluate in vitro the effects of these compounds on platelet aggregation induced by thrombin and ADP. Pretreatment of platelets with resveratrol or other tested phenolics (1-25 microg/ml) slightly reduced platelet aggregation stimulated by 5 microM ADP (P < 0.05) or 10 microM ADP (P < 0.005). The comparison of the inhibitory effects of tested compound in thrombin-induced platelet aggregation revealed that phenolic showed even stronger antiplatelet actions than resveratrol. These compounds also had an inhibitory effect on the thrombin-induced enzymatic platelet lipid peroxidation determined as the level of thiobarbituric acid reactive substances.

  8. 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.

  9. 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.

  10. 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.

  11. Permeability profile estimation of flavonoids and other phenolic compounds by biopartitioning micellar capillary chromatography.

    PubMed

    Diniz, Andréa; Escuder-Gilabert, Laura; Lopes, Norberto P; Gobbo-Neto, Leonardo; Villanueva-Camañas, Rosa María; Sagrado, Salvador; Medina-Hernández, María José

    2007-10-17

    This paper points out the usefulness of biopartitioning micellar chromatography (BMC) using capillary columns as a high-throughput primary screening tool providing key information about the oral absorption, skin permeability, and brain-blood distribution coefficients of 15 polyphenols (6 flavones, 2 flavonols, a flavanone, 2 flavan-3-ols, 3 phenolic acids, and a phloroglucinol) in a simple and economical way. For the compounds studied, except vicenin-2, rutin, chlorogenic acid, p-hydroxycinnamic acid, and 4-hydroxybenzoic acid, maximal oral absorption (>90%) can be expected, if there are not solubility problems or metabolic processes. On the other hand, the most retained compounds in BMC, that is, 5-hydroxyflavone, flavone, and flavanone, show the highest brain-blood distribution coefficients and skin permeability coefficients.

  12. Glycybridins A-K, Bioactive Phenolic Compounds from Glycyrrhiza glabra.

    PubMed

    Li, Kai; Ji, Shuai; Song, Wei; Kuang, Yi; Lin, Yan; Tang, Shunan; Cui, Zexu; Qiao, Xue; Yu, Siwang; Ye, Min

    2017-02-24

    In an attempt to discover bioactive agents from the herbal medicine Glycyrrhiza glabra (widely known as licorice), 11 new phenolic compounds, glycybridins A-K (1-11), along with 47 known phenolics (12-58) were isolated. Their structures were elucidated on the basis of extensive NMR and MS analyses as well as experimental and computed ECD data. According to the clinical therapeutic effects of licorice, enzyme or cell-based bioactivity screenings of 1-58 were conducted. A number of compounds significantly activate Nrf2, inhibit tyrosinase or PTP1B, inhibit LPS-induced NO production and NF-κB transcription, and inhibit the proliferation of human cancer cells (HepG2, SW480, A549, MCF7). Glycybridin D (4) showed moderate cytotoxic activities against the four cancer cell lines, with IC50 values ranging from 4.6 to 6.6 μM. Further studies indicated that 4 (10 mg/kg, ip) decreased tumor mass by 39.7% on an A549 human lung carcinoma xenograft mice model, but showed little toxicity.

  13. 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.

  14. 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

  15. Evaluation of leishmanicidal and trypanocidal activities of phenolic compounds from Calea uniflora Less.

    PubMed

    Lima, Tamires C; Souza, Rafaela J; Santos, Alan D C; Moraes, Milene H; Biondo, Nicole E; Barison, Andersson; Steindel, Mário; Biavatti, Maique W

    2016-01-01

    The phytochemical study of Calea uniflora led to the isolation of nine phenolic compounds identified as noreugenin (1), ethyl caffeate (2), a mixture of butein (3) + orobol (4), α-hydroxy-butein (5), caffeic acid (6), butein 4'-O-glucopyranosyl (7), quercetin 3-O-glucopyranosyl (8) and 3,5-di-O-caffeoylquinic acid (9). The chemical identity of the isolates was established on the basis of NMR and physical data. The chemical shifts of 5 and 7 have been reassigned and all the isolates were tested against Leishmania amazonensis and Trypanosoma cruzi amastigotes. None of the metabolites showed promising leishmanicidal activity. However, 2 and the mixture of 3 and 4 demonstrated interesting trypanocidal effect with IC50 values of 18.27 and 26.53 μM, respectively. Besides, these compounds did not present cytotoxic effect towards THP-1 cells, and compound 2 was 3.5-fold more selective than the mixture of 3+4.

  16. Imperanene, a novel phenolic compound with platelet aggregation inhibitory activity from Imperata cylindrica.

    PubMed

    Matsunaga, K; Shibuya, M; Ohizumi, Y

    1995-01-01

    Imperanene, a novel phenolic compound [1] has been isolated from Imperata cylindrica. Its structure was elucidated by spectroscopic evidence. Imperanene showed platelet aggregation inhibitory activity.

  17. Characterization, phenolic compounds and functional properties of Cucumis melo L. peels.

    PubMed

    Mallek-Ayadi, Sana; Bahloul, Neila; Kechaou, Nabil

    2017-04-15

    The aim of this work is to investigate the phytochemical composition and functional properties of the melon peels, considered as a by-product. Melon peels (maazoun cultivar) are rich in nutritional ingredients such as carbohydrates (69.77%) and ash (3.67%). They contain significant amounts of total dietary fibers (41.69%) and antioxidants as polyphenols and flavonoids (332mg/100g extract and 95.46mg/100g extract, respectively). The identification and the quantification of the phenolic compounds of melon peels were performed by high performance liquid chromatography apparatus. The obtained results indicate that hydroxybenzoic acids and flavones constitute their main phenolic classes. 3-Hydroxybenzoic acid is the major phenolic compound in the melon peels by 33.45mg/100g, followed by apigenin-7-glycoside (29.34mg/100g). Determination of the functional properties (water and oil retention capacities) and color shows that melon peels have properties that may be useful in industrial applications.

  18. 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.

  19. 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.

  20. The Extent of Fermentative Transformation of Phenolic Compounds in the Bioanode Controls Exoelectrogenic Activity in a Microbial Electrolysis Cell

    DOE PAGES

    Zeng, Xiaofei; Collins, Maya; Borole, Abhijeet P.; ...

    2016-11-27

    Phenolic compounds in hydrolysate/pyrolysate and wastewater streams produced during the pretreatment of lignocellulosic biomass for biofuel production present a significant challenge in downstream processes. Bioelectrochemical systems are increasingly recognized as an alternative technology to handle biomass-derived streams and to promote water reuse in biofuel production. Thus, a thorough understanding of the fate of phenolic compounds in bioanodes is urgently needed. The present study investigated the biotransformation of three structurally similar phenolic compounds (syringic acid, SA; vanillic acid, VA; 4-hydroxybenzoic acid, HBA), and their individual contribution to exoelectrogenesis in a microbial electrolysis cell (MEC) bioanode. Fermentation of SA resulted in themore » highest exoelectrogenic activity among the three compounds tested, with 50% of the electron equivalents converted to current, compared to 12 and 9% for VA and HBA, respectively. The biotransformation of SA, VA and HBA was initiated by demethylation and decarboxylation reactions common to all three compounds, resulting in their corresponding hydroxylated analogs. SA was transformed to pyrogallol (1,2,3-trihydroxybenzene), whose aromatic ring was then cleaved via a phloroglucinol pathway, resulting in acetate production, which was then used in exoelectrogenesis. In contrast, more than 80% of VA and HBA was converted to catechol (1,2-dihydroxybenzene) and phenol (hydroxybenzene) as their respective dead-end products. The persistence of catechol and phenol is explained by the fact that the phloroglucinol pathway does not apply to di- or mono-hydroxylated benzenes. Previously reported, alternative ring-cleaving pathways were either absent in the bioanode microbial community or unfavorable due to high energy-demand reactions. With the exception of acetate oxidation, all biotransformation steps in the bioanode occurred via fermentation, independently of exoelectrogenesis. Therefore, the observed

  1. The extent of fermentative transformation of phenolic compounds in the bioanode controls exoelectrogenic activity in a microbial electrolysis cell.

    PubMed

    Zeng, Xiaofei; Collins, Maya A; Borole, Abhijeet P; Pavlostathis, Spyros G

    2017-02-01

    Phenolic compounds in hydrolysate/pyrolysate and wastewater streams produced during the pretreatment of lignocellulosic biomass for biofuel production present a significant challenge in downstream processes. Bioelectrochemical systems are increasingly recognized as an alternative technology to handle biomass-derived streams and to promote water reuse in biofuel production. Thus, a thorough understanding of the fate of phenolic compounds in bioanodes is urgently needed. The present study investigated the biotransformation of three structurally similar phenolic compounds (syringic acid, SA; vanillic acid, VA; 4-hydroxybenzoic acid, HBA), and their individual contribution to exoelectrogenesis in a microbial electrolysis cell (MEC) bioanode. Fermentation of SA resulted in the highest exoelectrogenic activity among the three compounds tested, with 50% of the electron equivalents converted to current, compared to 12 and 9% for VA and HBA, respectively. The biotransformation of SA, VA and HBA was initiated by demethylation and decarboxylation reactions common to all three compounds, resulting in their corresponding hydroxylated analogs. SA was transformed to pyrogallol (1,2,3-trihydroxybenzene), whose aromatic ring was then cleaved via a phloroglucinol pathway, resulting in acetate production, which was then used in exoelectrogenesis. In contrast, more than 80% of VA and HBA was converted to catechol (1,2-dihydroxybenzene) and phenol (hydroxybenzene) as their respective dead-end products. The persistence of catechol and phenol is explained by the fact that the phloroglucinol pathway does not apply to di- or mono-hydroxylated benzenes. Previously reported, alternative ring-cleaving pathways were either absent in the bioanode microbial community or unfavorable due to high energy-demand reactions. With the exception of acetate oxidation, all biotransformation steps in the bioanode occurred via fermentation, independently of exoelectrogenesis. Therefore, the observed

  2. The Extent of Fermentative Transformation of Phenolic Compounds in the Bioanode Controls Exoelectrogenic Activity in a Microbial Electrolysis Cell

    SciTech Connect

    Zeng, Xiaofei; Collins, Maya; Borole, Abhijeet P.; Pavlostathis, Spyros

    2016-11-27

    Phenolic compounds in hydrolysate/pyrolysate and wastewater streams produced during the pretreatment of lignocellulosic biomass for biofuel production present a significant challenge in downstream processes. Bioelectrochemical systems are increasingly recognized as an alternative technology to handle biomass-derived streams and to promote water reuse in biofuel production. Thus, a thorough understanding of the fate of phenolic compounds in bioanodes is urgently needed. The present study investigated the biotransformation of three structurally similar phenolic compounds (syringic acid, SA; vanillic acid, VA; 4-hydroxybenzoic acid, HBA), and their individual contribution to exoelectrogenesis in a microbial electrolysis cell (MEC) bioanode. Fermentation of SA resulted in the highest exoelectrogenic activity among the three compounds tested, with 50% of the electron equivalents converted to current, compared to 12 and 9% for VA and HBA, respectively. The biotransformation of SA, VA and HBA was initiated by demethylation and decarboxylation reactions common to all three compounds, resulting in their corresponding hydroxylated analogs. SA was transformed to pyrogallol (1,2,3-trihydroxybenzene), whose aromatic ring was then cleaved via a phloroglucinol pathway, resulting in acetate production, which was then used in exoelectrogenesis. In contrast, more than 80% of VA and HBA was converted to catechol (1,2-dihydroxybenzene) and phenol (hydroxybenzene) as their respective dead-end products. The persistence of catechol and phenol is explained by the fact that the phloroglucinol pathway does not apply to di- or mono-hydroxylated benzenes. Previously reported, alternative ring-cleaving pathways were either absent in the bioanode microbial community or unfavorable due to high energy-demand reactions. With the exception of acetate oxidation, all biotransformation steps in the bioanode occurred via fermentation, independently of exoelectrogenesis. Therefore, the observed

  3. 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.

  4. 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.

  5. In vitro bioaccessibility, transepithelial transport and antioxidant activity of Urtica dioica L. phenolic compounds in nettle based food products.

    PubMed

    Bonetti, Gianpiero; Tedeschi, Paola; Meca, Giuseppe; Bertelli, Davide; Mañes, Jordi; Brandolini, Vincenzo; Maietti, Annalisa

    2016-10-12

    Nettle (Urtica dioica L.) is a well-known plant with a wide historical background use of stems, roots and leaves. Nettle leaves are an excellent source of phenolic compounds, principally 3-caffeoylquinic acid (3-CQA), caffeoylmalic acid (CMA) and rutin. The aim of this work was to evaluate the bioaccessibility (BAC), the bioavailability (BAV) and the antioxidant activity of nettle phenolic compounds present in foods and supplements. The BAC of nettle phenolics was evaluated with an in vitro dynamic digestion of real food matrices: the type of food matrix and chemical characteristic affected the kinetics of release and solubilization, with the highest BAC after duodenal digestion. A study of duodenal trans epithelial transport evidenced low bioavailability of native forms of 3-CQA, CMA and rutin. Simulation of colonic metabolism confirmed that phenolic compounds are fermented by gut microflora, confirming the need for further investigations on the impact of phenolic compounds at the large intestine level. Photochemiluminescence assay of the simulated digestion fluids demonstrated that ingestion of Urtica based foods contributes to create an antioxidant environment against superoxide anion radicals in the entire gastrointestinal tract (GIT).

  6. Enhanced transformation of malachite green by laccase of Ganoderma lucidum in the presence of natural phenolic compounds.

    PubMed

    Murugesan, Kumarasamy; Yang, In-Hee; Kim, Young-Mo; Jeon, Jong-Rok; Chang, Yoon-Seok

    2009-02-01

    In this study, we investigated the efficacy of phenolic extract of wheat bran and lignin-related phenolic compounds as natural redox mediators on laccase-mediated transformation of malachite green (MG) using purified laccase from the white-rot fungus Ganoderma lucidum. G. lucidum laccase was able to decolorize 40.7% MG dye (at 25 mg l(-1)) after 24 h of incubation. Whereas, the addition of phenolic extract of wheat bran enhanced the decolorization significantly (p<0.001) by two- to threefold than that of purified laccase alone. Among various natural phenolic compounds, acetovanillone, p-coumaric acid, ferulic acid, syringaldehyde, and vanillin were the most efficient mediators, as effective as the synthetic mediator 1-hydroxybenzotriazole. Characterization of MG transformation products by HPLC, UV-Vis, and liquid chromatography-mass spectrometry-electrospray ionization analysis revealed that N-demethylation was the key mechanism of decolorization of MG by laccase. Growth inhibition test based on mycelial growth inhibition of white rot fungus Phanerochaete chrysosporium revealed that treatment with laccase plus natural mediators effectively reduced the growth inhibitory levels of MG than that of untreated one. Among all the tested compounds, syringaldehyde showed the highest enhanced decolorization, as a consequence reduced growth inhibition was observed in syringaldehyde-treated samples. The results of the present study revealed that the natural phenolic compounds could alternatively be used as potential redox mediators for effective laccase-mediated decolorization of MG.

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

    PubMed Central

    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

    2015-01-01

    Proanthocyanidins (PACs) are secondary plant metabolites that mediate non-enzymatic 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: PACs 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 combination of 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 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 modulate the mechanism of cross-linking at the molecular, inter-molecular, and inter-micro-fibrillar levels. PMID:25379878

  8. Protective effect of phenolic compounds on carbonyl-amine reactions produced by lipid-derived reactive carbonyls.

    PubMed

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

    2017-08-15

    The degradation of phenylalanine initiated by 2-pentenal, 2,4-heptadienal, 4-oxo-2-pentenal, 4,5-epoxy-2-heptenal, or 4,5-epoxy-2-decenal in the presence of phenolic compounds was studied to determine the structure-activity relationship of phenolic compounds on the protection of amino compounds against modifications produced by lipid-derived carbonyls. The obtained results showed that flavan-3-ols were the most efficient phenolic compounds followed by single m-diphenols. The effectiveness of these compounds was found to be related to their ability to trap rapidly the carbonyl compound, avoiding in this way the reaction of the carbonyl compound with the amino acid. The ability of flavan-3-ols for this reaction is suggested to be related to the high electronic density existing in some of the aromatic carbons of their ring A. This is the first report showing that carbonyl-phenol reactions involving lipid-derived reactive carbonyls can be produced more rapidly than carbonyl-amine reactions, therefore providing a satisfactory protection of amino compounds.

  9. Cytoprotective effects of phenolic acids on methylglyoxal-induced apoptosis in Neuro-2A cells.

    PubMed

    Huang, Shang-Ming; Chuang, Hong-Chih; Wu, Chi-Hao; Yen, Gow-Chin

    2008-08-01

    In the process of glycation, methylglyoxal is a reactive dicarbonyl compound physiologically generated as an intermediate of glycolysis, and is found in high levels in blood or tissue of diabetic models. Biological glycation has been commonly implicated in the development of diabetic microvascular complications of neuropathy. Increasing evidence suggests that neuronal cell cycle regulatory failure followed by apoptosis is an important mechanism in the development of diabetic neuropathy complication. Naturally occurring antioxidants, especially phenolic acids have been recommended as the major bioactive compounds to prevent chronic diseases and promote health benefits. The objective of this study was to investigate the inhibitory abilities of phenolic acids (chlorogenic acid, syringic acid and vanillic acid) on methylglyoxal-induced mouse Neuro-2A neuroblastoma (Neuro-2A) cell apoptosis in the progression of diabetic neuropathy. The data indicated that methylglyoxal induced mouse Neuro-2A neuroblastoma (Neuro-2A) cell apoptosis via alternation of mitochondria membrane potential and Bax/Bcl-2 ratio, activation of caspase-3, and cleavage of poly (ADP-ribose) polymerase. Furthermore, the results demonstrated that activation of mitogen-activated protein kinase signal pathways (JNK and p38) participated in the methylglyoxal-induced Neuro-2A cell apoptosis process. Treatment of Neuro-2A cells with phenolic acids markedly suppresses cell apoptosis induced by methylglyoxal, suggesting that phenolic acids possess cytoprotective ability in the prevention of diabetic neuropathy complication.

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

    PubMed Central

    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. PMID:26784345

  11. Phenolic compounds in cherry ( Prunus avium ) heartwood with a view to their use in cooperage.

    PubMed

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

    2010-04-28

    The phenolic and tannic composition of heartwood extracts from Prunus avium , commonly known as cherry tree, before and after toasting in cooperage were studied using HPLC-DAD and HPLC-DAD/ESI-MS. Nonflavonoid (16 compounds) and flavonoid (27 compounds) polyphenols were identified, 12 of them in only a tentative way. The nonflavonoids found were lignin constituents, and their pattern is different compared to oak, since they include compounds such as protocatechuic acid and aldehyde, p-coumaric acid, methyl vanillate, methyl syringate, and benzoic acid, but not ellagic acid, and only a small quantity of gallic acid. In seasoned wood we found a great variety of flavonoid compounds which have not been found in oak wood for cooperage, mainly, in addition to the flavan-3-ols (+)-catechin, a B-type procyanidin dimer, and a B-type procyanidin trimer, the flavanones naringenin, isosakuranetin, and eriodictyol and the flavanonols aromadendrin and taxifolin. Seasoned and toasted cherry wood showed different ratios of flavonoid to nonflavonoid compounds, since toasting results in the degradation of flavonoids, and the formation of nonflavonoids from lignin degradation. On the other hand, the absence of hydrolyzable tannins in cherry wood, which are very important in oak wood, is another particular characteristic of this wood that should be taken into account when considering its use in cooperage.

  12. [Phenolic compounds in leaves insertions of Mentha × villosa Huds. cv. Snežná].

    PubMed

    Tekeľová, Daniela; Bittner Fialová, Silvia; Tóth, Jaroslav; Czigle, Szilvia

    2016-01-01

    Lamiaceae plants mostly accumulate active ingredients in their leaves. The subfamily Nepetoideae, including the genus Mentha L., is characterized by the presence of essential oil and antioxidant phenolics, chiefly hydroxycinnamic acids with predominance of rosmarinic acid, and flavonoids. Mentha × piperita and M. spicata are the most broadly used mints in both medicine and industry, while M. x villosa is less known in our country. Herbal drugs in the form of leaves are usually analysed unpartitioned, while single leaves insertions have only been studied occasionally. Therefore, the aim of this work was the quantification of the active compounds content in the leaves pairs of Mentha × villosa Huds. cv. Snežná, using pharmacopoeial methods: total hydroxycinnamic derivatives expressed as rosmarinic acid (THD) and luteolin-type flavonoids. THD content ranged from 6.7% to 9.4% in the leaves pairs water extracts, and from 6.6% to 14.0% in methanol extracts. Flavonoids contents, expressed as luteolin-7-O-glucoside, ranged from 4.0% to 8.8% in water extracts, and from 4.0% to 10.5% in methanol extracts. Antioxidant activity (DPPH) expressed as SC50 ranged from 10.2 to 16.9 μg.ml-1 (drug dry weight) in water extracts, and from 10.7 to 21.6 μg.ml-1 in methanol extracts. The highest content of phenolic compounds as well as the highest antioxidant activity were found to be in the top sheet, while the lowest content of phenolic compounds and lowest antioxidant activity were detected in the leaves of the middle stem part.Key words: Mentha × villosa Huds cv. Snežná hydroxycinnamic derivatives rosmarinic acid luteolin-7-O-glucoside DPPH.

  13. High-performance liquid chromatography-mass spectrometry profiling of phenolic compounds for evaluation of olive oil bitterness and pungency.

    PubMed

    Dierkes, Georg; Krieger, Sonja; Dück, Roman; Bongartz, Annette; Schmitz, Oliver J; Hayen, Heiko

    2012-08-08

    Bitterness and pungency are important parameters for olive oil quality. Therefore, two instrumental methods for evaluation of these taste attributes were developed. The first one is based on the photometric measurement of total phenolic compounds content, whereas the second one is based on the semiquantitative evaluation of hydrophilic compounds by high-performance liquid chromatography-mass spectrometry (HPLC-MS). Evaluation of total phenolic compounds content was performed by a modified method for the determination of the K(225) value using a more specific detection based on the pH value dependency of absorbance coefficients of phenols at λ = 274 nm. The latter method was not suitable for correct prediction, because no significant correlation between bitterness/pungency and total phenolic compounds content could be found. For the second method, areas of 25 peaks detected in 54 olive oil samples by a HPLC-MS profiling method were correlated with the bitterness and pungency by partial least-squares regression. Six compounds (oleuropein aglycon, ligstroside aglycon, decarboxymethyl oleuropein aglycon, decarboxymethyl ligstroside aglycon, elenolic acid, and elenolic acid methyl ester) show high correlations to bitterness and pungency. The computed model using these six compounds was able to predict bitterness and pungency of olive oil in the error margin of the sensory evaluation (±0.5) for most of the samples.

  14. 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.

  15. 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

  16. Phenolic compounds from male castoreum of the North American beaver,Castor canadensis.

    PubMed

    Tang, R; Webster, F X; Müller-Schwarze, D

    1993-07-01

    North American beaver (Castor canadensis) mark their territories with castoreum, the contents of their castor sacs. In their territories, beaver respond with scent marking to experimental scent marks consisting of castoreum, or selected single components. In part, the unique odor of castoreum is due to large amounts of phenolic compounds. Purified phenolic components were analyzed by GC, GC-MS, and NMR; identifications were confirmed by comparing the spectra of synthetic phenols with those of the isolated phenols. Of the 15 phenols reported elsewhere, only five were confirmed in our analysis; the other 10 phenolic compounds are either absent or are not volatile enough to be detected by our methods. In addition, 10 phenolic compounds have been identified in this study that were not reported in the previous papers concerning the constitution of castoreum.

  17. 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.

  18. Production of anthraquinones, phenolic compounds and biological activities from hairy root cultures of Polygonum multiflorum Thunb.

    PubMed

    Thiruvengadam, Muthu; Praveen, Nagella; Kim, Eun-Hye; Kim, Seung-Hyun; Chung, Ill-Min

    2014-05-01

    Polygonum multiflorum Thunb. is a highly important medicinal plant producing anthraquinones (emodin and physcion) and phenolic compounds which has pharmaceutical use. In vitro seedling explants such as roots, internodals, nodals and leaves were inoculated with A. rhizogenes strain KCTC 2703. Transformed roots were induced from internodals and leaf explants. Six transgenic clones of hairy roots were established and confirmed by polymerase chain reaction (PCR) and reverse transcription-PCR (RT-PCR) using rolC specific primers. Hairy roots cultured using MS liquid medium supplemented with 30 g/l sucrose showed highest accumulation of biomass (99.05 g/l FW [fresh weight] and 10.95 g/l DW [dry weight]) and highest production of anthraquinones content (emodin 211.32 μg/g DW and physcion 353.23 μg/g DW) were observed at 20 days. Nearly 9.5-fold increment of biomass was evident in suspension cultures at 20 days of culture and hairy root biomass produced in suspension cultures possessed 3.7- and 3.5-fold higher content of emodin and physcion, respectively, when compared with the untransformed control roots. MS basal liquid medium was superior for the growth of hairy roots and production of anthraquinones compared with other culture media evaluated (SH, B5 and N6), with MS-basal liquid medium supplemented with 30 g/l sucrose was optimal for secondary metabolite production. A total of 23 polyphenolic compounds were identified and quantified from P. multiflorum untransformed and hairy roots, which includes hydroxybenzoic acids, hydroxycinnamic acids, flavonols and other groups of phenolic compounds. The ultra-performance liquid chromatography (UPLC) analysis of the phenolic compounds profile revealed that pyrogallol, hesperidin, naringenin and formononetin were higher in hairy roots compared to untransformed roots. The total phenolics, flavonoids content, antioxidant and antimicrobial activity was high in hairy roots compared to untransformed roots. This is the first

  19. Plant secondary metabolites and gut health: the case for phenolic acids.

    PubMed

    Russell, Wendy; Duthie, Garry

    2011-08-01

    Plant-based diets contain a plethora of secondary metabolites that may impact on health and disease prevention. Much attention has been focused on the potential bioactivity and nutritional relevance of several classes of phytochemicals such as flavonoids, carotenoids, phyto-oestrogens and glucosinolates. Less attention has been paid to simple phenolic acids that are widely found in fruit, vegetables, herbs, spices and beverages. Daily intakes may exceed 100 mg. In addition, bacteria in the gut can perform reactions that transform more complex plant phenolics such as anthocyanins, procyanidins, flavanones, flavonols, tannins and isoflavones into simple phenolic metabolites. The colon is thus a rich source of potentially active phenolic acids that may impact both locally and systemically on gut health. Both the small and large intestine (colon) contain absorption sites for phenolic acids but low post-prandial concentrations in plasma indicate minimal absorption early in the gastrointestinal tract and/or rapid hepatic metabolism and excretion. Therefore, any bioactivity that contributes to gut health may predominantly occur in the colon. Several phenolic acids affect the expression and activity of enzymes involved in the production of inflammatory mediators of pathways thought to be important in the development of gut disorders including colon cancer. However, at present, we remain largely ignorant as to which of these compounds are beneficial to gut health. Until we can elucidate which pro-inflammatory and potentially carcinogenetic changes in gene expression can be moderated by simple phenolic acids, it is not possible to recommend specific plant-based foods rich in particular phenolics to optimise gut health.

  20. Phenolic compounds in strawberry (Fragaria x ananassa Duch.) fruits: Composition in 27 cultivars and changes during ripening.

    PubMed

    Aaby, Kjersti; Mazur, Sebastian; Nes, Arnfinn; Skrede, Grete

    2012-05-01

    Phenolic compounds in fruits of 27 cultivars of strawberry (Fragaria x ananassa Duch.) grown in Norway were characterised and quantified by HPLC-DAD-MS(n). Total phenolic content, calculated as the sum of the individual compounds, varied 2.3-fold among cultivars, i.e., from 57 to 133mg/100g of fw. There were significant differences among cultivars in concentration of all phenolic compounds. The highest variation between cultivars was found for cinnamoyl glucose (0.6-24.9mg/100g of fw). Concentration of anthocyanins, the most abundant class of phenolic compounds in the majority of the cultivars, varied from 8.5 to 65.9mg/100g of fw. Flavan-3-ols (11-45mg/100g of fw) and ellagitannins (7.7-18.2mg/100g of fw) contributed on average 28% and 14% to total phenolic contents in the strawberry cultivars, respectively. In three cultivars harvested at three stages of ripeness, anthocyanins and cinnamic acid conjugates were the compounds most affected by ripening. The anthocyanin profile for the individual cultivars was only slightly affected by ripening and growing conditions.

  1. Antioxidant and cyclooxygenase inhibitory phenolic compounds from Ocimum sanctum Linn.

    PubMed

    Kelm, M A; Nair, M G; Strasburg, G M; DeWitt, D L

    2000-03-01

    Anti-oxidant bioassay-directed extraction of the fresh leaves and stems of Ocimum sanctum and purification of the extract yielded the following compounds; cirsilineol [1], cirsimaritin [2], isothymusin [3], isothymonin [4], apigenin [5], rosmarinic acid [6], and appreciable quantities of eugenol. The structures of compounds 1-6 were established using spectroscopic methods. Compounds 1 and 5 were isolated previously from O. sanctum whereas compounds 2 and 3 are here identified for the first time from O. sanctum. Eugenol, a major component of the volatile oil, and compounds 1, 3, 4, and 6 demonstrated good antioxidant activity at 10-microM concentrations. Anti-inflammatory activity or cyclooxygenase inhibitory activity of these compounds were observed. Eugenol demonstrated 97% cyclooxygenase-1 inhibitory activity when assayed at 1000-microM concentrations. Compounds 1, 2, and 4-6 displayed 37, 50, 37, 65, and 58% cyclooxygenase-1 inhibitory activity, respectively, when assayed at 1000-microM concentrations. Eugenol and compounds 1, 2, 5, and 6 demonstrated cyclooxygenase-2 inhibitory activity at slightly higher levels when assayed at 1000-microM concentrations. The activities of compounds 1-6 were comparable to ibuprofen, naproxen, and aspirin at 10-, 10-, and 1000-microM concentrations, respectively. These results support traditional uses of O. sanctum and identify the compounds responsible.

  2. [The content of phenolic acids in the edible parts of selected varieties of apples].

    PubMed

    Malik, Agnieszka; Kiczorowska, Bozena; Zdyb, Justyna

    2009-01-01

    Fruits and vegetables are essential sources of many nutritive substances which are necessary for normal function of the organism. One of the mostly consumed fruits in many European countries, including Poland is apples. The prohealthy properties of apples are associated with the contents of polyphenolic compounds, thus including in parts phenolic acids which have antioxidant properties. The concentration of these compounds depends on many factors such as variety climate and soil conditions, maturity as well as agro technical operations. The aim of this investigation was to compare the concentrations of phenolic acids and epicatechin in the varieties of apple Champion and Jonica, which were collected from different orchards around Lublin. The phenolic compounds were assayed using a Symmetry column carrier RP-C18 (Waters) integrated with a high pressure liquid chromatography apparatus. The dominant phenolic acids found in the Champion variety was chlorogenic acid, whereas in the Jonica variety, chlorogenic and homovanilic acids were the dominate once. The highest concentrations of chlorogenic acid was detected in the pulp of an apple (Jonica variety) collected from the orchards around the cities of Puławy and Lublin, whereas homovanilic acid was the highest in the other samples collected from the orchards in the vicinity of Stryjno and Góry Markuszowskie. Among the Jonica and Champion varieties of apples collected from various orchards in the vicinity of Lublin, the highest content of epicatechin (13,12 mg/kg) was found in the pulps of Champions variety collected in Puławy. In general, the Champion variety was the best source of phenolic acids and epicatechin compared to the Jonica variety independent of the harvest zone.

  3. 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

  4. 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.

  5. 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.

  6. Methods for extraction and determination of phenolic acids in medicinal plants: a review.

    PubMed

    Arceusz, Agnieszka; Wesolowski, Marek; Konieczynski, Pawel

    2013-12-01

    Phenolic acids constitute a group of potentially immunostimulating compounds. They occur in all medicinal plants and are widely used in phytotherapy and foods of plant origin. In recent years, phenolic acids have attracted much interest owing to their biological functions. This paper reviews the extraction and determination methods of phenolic acids in medicinal plants over the last 10 years. Although Soxhlet extraction and ultrasonic assisted extraction (UAE) are commonly used for the extraction of phenolic acids from plant materials, alternative techniques such as supercritical fluid extraction (SFE), and accelerated solvent extraction (ASE) can also be used. After extraction, phenolic acids are determined usually by liquid chromatography (LC) owing to the recent developments in this technique, especially when it is coupled with mass spectrometry (MS). Also detection systems are discussed, including UV-Vis, diode array, electrochemical and fluorimetric. Other popular techniques for the analysis of this group of secondary metabolites are gas chromatography coupled with mass spectrometry (GC-MS) and capillary electrophoresis (CE).

  7. Biotransformation of Furanic and Phenolic Compounds with Hydrogen Gas Production in a Microbial Electrolysis Cell.

    PubMed

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

    2015-11-17

    Furanic and phenolic compounds are problematic byproducts resulting from the breakdown of lignocellulosic biomass during biofuel production. 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 substrate in the bioanode was assessed. The rate and extent of biotransformation of the five compounds and efficiency of H2 production, as well as the structure of the anode microbial community, 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 1200 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 that of 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 biotransformation of the five compounds took place via fermentation followed by exoelectrogenesis. 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 1200 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 MEC H2 production demonstrated in this study is an alternative to the currently used process of reforming natural gas to supply H2 needed to upgrade bio-oils to stable

  8. Phenolic compounds: The inhibition effect on polyol pathway enzymes.

    PubMed

    Aslan, Hatice Esra; Beydemir, Şükrü

    2017-03-25

    The polyol pathway called as sorbitol way is a small part of glycose metabolism. The pathway is regarded as an important element in the pathogenesis of various diabetic complications in individuals with diabetes mellitus. The pathway plays a crucial role in hyperglycemia. The polyol pathway contains two enzymes as aldose reductase (AR) and sorbitol dehydrogenase (SDH). In the present study, AR and SDH were purified from sheep liver by using simple chromatographic methods. AR was purified with a yield of 2.11% and approximately 162 fold and SDH was purified with a yield of 0.53% and approximately 9.07 purification fold. Sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE) was performed to check the purity and determine the subunit molecular weights of the enzymes. Subunit molecular weights of AR and SDH were 38.82 kDa and 37.74 kDa, respectively. Optimal pH, optimal ionic strength, optimal temperature, activation energy, activation enthalpy, Q10 value and stable pH were determined as 5.5, 10 mM, 50 °C, 2.16 kcal, 1.52 kcal, 1.33 and 8.0 for AR enzyme, respectively. The kinetic parameters Km and Vmax for AR were determined as 0.45 mM and 0.55 EU/mL, respectively. These parameters were studied for only AR in the present study, because it was previously studied for SDH. IC50 values of 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, salicylic acid, p-coumaric acid, ellagic acid, gallic acid, ferrulic acid and caffeic acid on AR and SDH activities were found as 120, 92.0, 49.0, 39.0, 40.0, 690, 7.00, 103, 84.0, 3.00 μM for AR enzyme and 5060, 8350, 6730, 7070, 5780, 24.0, 13.0, 26.0, 17.0, 21.0 μM for SDH enzyme, respectively. According to these results, caffeic acid was the strongest inhibitor for AR activity compared to the other phenolic acids and ellagic acid was also the strongest inhibitor for SDH activity.

  9. Separation and characterization of soluble esterified and glycoside-bound phenolic compounds in dry-blanched peanut skins by liquid chromatography-electrospray ionization mass spectrometry.

    PubMed

    Ma, Yuanyuan; Kosińska-Cagnazzo, Agnieszka; Kerr, William L; Amarowicz, Ryszard; Swanson, Ruthann B; Pegg, Ronald B

    2014-11-26

    A large variety of soluble phenolic compounds, including phenolic acids (hydroxybenzoic acids, ethyl protocatechuate, and hydroxycinnamic acids, as well as phenylacetic acid and phenyllactic acid), stilbenes (trans-piceatannol and trans-3,3',5,5'-tetrahydroxy-4'-methoxystilbene), flavan-3-ols (e.g., (-)-epicatechin, (+)-catechin, (-)-epiafzelechin, and their polymers (the proanthocyanidins, PACs)), other flavonoids (e.g., isoflavones, flavanols, and flavones), and biflavonoids, were released from esters and glycosides by base/acid hydrolysis and identified in acetonic extracts of dry-blanched peanut skins (PS). Reversed-phase high-performance liquid chromatography (RP-HPLC) coupled with electrospray ionization mass spectrometry (ESI-MS(n)) was applied to separate and identify the phenolic constituents. Tentative identification of the separated phenolics was based on molecular ions and MS(n) fragmentation patterns acquired by ESI-MS in the negative-ion mode. Identification of free phenolic acids, stilbenes, and flavonoids was also achieved by commercial standards and by published literature data. Quantification was performed on the basis of peak areas of the UV signals from the HPLC chromatograms and calibration curves of the commercial standards. The flavonoids of PS exist mostly in glycoside-bound forms, but the aglycones can be liberated upon acid hydrolysis. PS contain significantly more PACs compared to free phenolic compounds: PAC monomers to tetramers constituted 92.0% of esterified phenolic compounds. The PAC monomer ((+)-catechin) and dimers are the main phenolics released from glycosides and account for 31.7 and 59.1%, respectively, of the total glycoside-bound phenolic compounds.

  10. Degradation of phenol and toxicity of phenolic compounds: a comparison of cold-tolerant Arthrobacter sp. and mesophilic Pseudomonas putida.

    PubMed

    Margesin, Rosa; Bergauer, Philipp; Gander, Silvia

    2004-06-01

    Phenol degradation efficiency of cold-tolerant Arthrobacter sp. AG31 and mesophilic Pseudomonas putida DSM6414 was compared. The cold-tolerant strain was cultivated at 10 degrees C, while the mesophile was grown at 25 degrees C. Both strains degraded 200 mg and 400 mg phenol/l within 48-72 h of cultivation, but the cold-tolerant strain produced more biomass than the mesophile. Both strains oxidized catechol by the ortho type of ring fission. Catechol 1,2 dioxygenase (C1,2D) activity was found intra- and extracellularly in the absence and in the presence of phenol. In the presence of 200 mg phenol/l, C1,2D activity of the mesophile was about 1.5- to 2-fold higher than that of the cold-tolerant strain. However, an initial phenol concentration of 400 mg/l resulted in a comparable enzyme activity of the cold-tolerant and the mesophilic strain. The two strains differed significantly in their toxicity pattern towards 12 aromatic (mostly phenolic) compounds at different growth temperatures, which was determined via growth inhibition in the presence of nutrients and toxicants. For the cold-tolerant strain, toxicity was significantly lower at 10 degrees C than at 25 degrees C. The mesophile showed a significantly lower susceptibility to high hydrocarbon concentrations when grown at 25 degrees C compared to 10 degrees C.

  11. Identification and quantification of phenolic compounds in bambangan (Mangifera pajang Kort.) peels and their free radical scavenging activity.

    PubMed

    Hassan, Fouad Abdulrahman; Ismail, Amin; Abdulhamid, Azizah; Azlan, Azrina

    2011-09-14

    Phenolic compounds and antioxidant capacity of acidified methanolic extract prepared from fully ripe bambangan (Mangifera pajang K.) peel cultivated in Sarawak, Malaysia, were analyzed. The total phenolic content (98.3 mg GAE/g) of bambangan peel powder (BPP) was determined by the Folin-Ciocalteu method. BPP showed a strong potency of antioxidant activity and was consistent with that of BHT and vitamin C as confirmed by the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity and FRAP (ferric-reducing antioxidant power) assays. Gallic acid, p-coumaric acid, ellagic acid, protocatechuic acid, and mangiferin were the major compounds among the 16 phenolics that have been identified and quantified in M. pajang peels with 20.9, 12.7, 7.3, 5.4, and 4.8 mg/g BPP, respectively. Peak identities were confirmed by comparing their retention times, UV-vis absorption spectra, and mass spectra with authentic standards. The 16 phenolic compounds identified in M. pajang K. using HPLC-DAD and TSQ-ESI-MS are reported here for the first time.

  12. 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.

  13. 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

  14. Oxidative stability, phenolic compounds and antioxidant potential of a virgin olive oil enriched with natural bioactive compounds.

    PubMed

    Delgado-Adámez, Jonathan; Baltasar, M Nieves Franco; Yuste, María Concepción Ayuso; Martín-Vertedor, Daniel

    2014-01-01

    The aim of this research was to evaluate strategies for the development of a virgin olive oil (VOO) enriched with aqueous extracts of olive leaf and cake to increase the necessary dose in the diet of phenolic compounds with a natural product, as phenolic compounds are involved on the healthy properties of olive oil. Different extraction procedures were evaluated with the aim of increasing the phenol content and antioxidant potential of extracts of olive leaf and cake. As leaves extract presented a higher total phenolic content, it was characterized in order to determine its phenolic profile, and was employed to enrich VOO. Diverse procedures were used to prepare enriched VOO with the leaves extract, and finally the effects of phenol enrichment were evaluated based on the antioxidant potential and oxidative stability of the prepared phenol-enriched virgin olive oils. These enriched VOOs increased significantly the content in phenolic compounds, antioxidant potential and oxidative stability 40, 4 and 1.5 fold more, respectively, than the Control oil. Furthermore, the addition of lecithin had a positive effect both on the phenolic compounds content, and on the antioxidant potential of the oils. Besides, the use of the olive leaves extract, with and without lecithin respectively, supposes a strategy potential for reducing the harmful effects that inflicts long-term preservation of VOOs and its possible deterioration.

  15. 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.

  16. 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.

  17. 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.

  18. 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.

  19. Enhanced Production of Anthraquinones and Phenolic Compounds and Biological Activities in the Cell Suspension Cultures of Polygonum multiflorum.

    PubMed

    Thiruvengadam, Muthu; Rekha, Kaliyaperumal; Rajakumar, Govindasamy; Lee, Taek-Jun; Kim, Seung-Hyun; Chung, Ill-Min

    2016-11-16

    Anthraquinones (AQs) and phenolic compounds are important phytochemicals that are biosynthesized in cell suspension cultures of Polygonum multiflorum. We wanted to optimize the effects of plant growth regulators (PGRs), media, sucrose, l-glutamine, jasmonic acid (JA), and salicylic acid (SA) for the production of phytochemicals and biomass accumulation in a cell suspension culture of P. multiflorum. The medium containing Murashige and Skoog (MS) salts and 4% sucrose supplemented with 1 mg/L 2,4-dichlorophenoxyacetic acid, 0.5 mg/L thidiazuron, and 100 µM l-glutamine at 28 days of cell suspension culture was suitable for biomass accumulation and AQ production. Maximum biomass accumulation (12.5 and 12.35 g fresh mass (FM); 3 and 2.93 g dry mass (DM)) and AQ production (emodin 295.20 and 282 mg/g DM; physcion 421.55 and 410.25 mg/g DM) were observed using 100 µM JA and SA, respectively. JA- and SA-elicited cell cultures showed several-fold higher biomass accumulation and AQ production than the control cell cultures. Furthermore, the cell suspension cultures effectively produced 23 phenolic compounds, such as flavonols and hydroxycinnamic and hydroxybenzoic acid derivatives. PGR-, JA-, and SA-elicited cell cultures produced a higher amount of AQs and phenolic compounds. Because of these metabolic changes, the antioxidant, antimicrobial, and anticancer activities were high in the PGR-, JA-, and SA-elicited cell cultures. The results showed that the elicitors (JA and SA) induced the enhancement of biomass accumulation and phytochemical (AQs and phenolic compounds) production as well as biological activities in the cell suspension cultures of P. multiflorum. This optimized protocol can be developed for large-scale biomass accumulation and production of phytochemicals (AQs and phenolic compounds) from cell suspension cultures, and the phytochemicals can be used for various biological activities.

  20. Enhanced Production of Anthraquinones and Phenolic Compounds and Biological Activities in the Cell Suspension Cultures of Polygonum multiflorum

    PubMed Central

    Thiruvengadam, Muthu; Rekha, Kaliyaperumal; Rajakumar, Govindasamy; Lee, Taek-Jun; Kim, Seung-Hyun; Chung, Ill-Min

    2016-01-01

    Anthraquinones (AQs) and phenolic compounds are important phytochemicals that are biosynthesized in cell suspension cultures of Polygonum multiflorum. We wanted to optimize the effects of plant growth regulators (PGRs), media, sucrose, l-glutamine, jasmonic acid (JA), and salicylic acid (SA) for the production of phytochemicals and biomass accumulation in a cell suspension culture of P. multiflorum. The medium containing Murashige and Skoog (MS) salts and 4% sucrose supplemented with 1 mg/L 2,4-dichlorophenoxyacetic acid, 0.5 mg/L thidiazuron, and 100 µM l-glutamine at 28 days of cell suspension culture was suitable for biomass accumulation and AQ production. Maximum biomass accumulation (12.5 and 12.35 g fresh mass (FM); 3 and 2.93 g dry mass (DM)) and AQ production (emodin 295.20 and 282 mg/g DM; physcion 421.55 and 410.25 mg/g DM) were observed using 100 µM JA and SA, respectively. JA- and SA-elicited cell cultures showed several-fold higher biomass accumulation and AQ production than the control cell cultures. Furthermore, the cell suspension cultures effectively produced 23 phenolic compounds, such as flavonols and hydroxycinnamic and hydroxybenzoic acid derivatives. PGR-, JA-, and SA-elicited cell cultures produced a higher amount of AQs and phenolic compounds. Because of these metabolic changes, the antioxidant, antimicrobial, and anticancer activities were high in the PGR-, JA-, and SA-elicited cell cultures. The results showed that the elicitors (JA and SA) induced the enhancement of biomass accumulation and phytochemical (AQs and phenolic compounds) production as well as biological activities in the cell suspension cultures of P. multiflorum. This optimized protocol can be developed for large-scale biomass accumulation and production of phytochemicals (AQs and phenolic compounds) from cell suspension cultures, and the phytochemicals can be used for various biological activities. PMID:27854330

  1. Selectivity and potential interference from phenolic compounds in chemiluminescence methods for the determination of synephrine.

    PubMed

    Francis, Paul S; Brown, Allyson J; Bellomarino, Sara A; Taylor, Amelia M; Slezak, Teo; Barnett, Neil W

    2009-01-01

    Three recently reported chemiluminescence methods (based on reactions with alkaline luminol and hexacyanoferrate(III); acidic cerium(IV) and rhodamine B; and acidic permanganate with polyphosphates) for the determination of synephrine were re-evaluated in terms of their selectivity towards this analyte in comparison to other phenolic compounds. A fourth reagent system, acidic soluble manganese(IV) and formaldehyde, was also examined. Each set of reagents was sensitive towards synephrine (limits of detection were 3 x 10(-9), 5 x 10(-8), 1 x 10(-8) and 1 x 10(-8) mol/L, respectively) but also responded with numerous other phenolic compounds, including some that are present in citrus fruit extracts, dietary supplements and/or biological fluids. It is therefore recommended that the determination of synephrine in these matrices should incorporate physical separation of sample components (e.g. chromatography or electrophoresis). In more general terms, this study illustrates that accurate percentage recoveries for an analyte in spiked samples (without validation against another analytical method) are insufficient to confirm the analytical utility of new flow-injection analysis (FIA) procedures.

  2. 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.

  3. Microchip electrophoresis with amperometric detection for a novel determination of phenolic compounds in olive oil.

    PubMed

    Godoy-Caballero, María del Pilar; Acedo-Valenzuela, María Isabel; Galeano-Díaz, Teresa; Costa-García, Agustín; Fernández-Abedul, María Teresa

    2012-11-07

    The relevance of the development of microchip electrophoresis applications in the field of food analysis is considered in this work. A novel method to determine important phenolic compounds in extra virgin olive oil samples using a miniaturized chemical analysis system is presented in this paper. Three interesting phenolic compounds in olive oil and fruit (tyrosol, hydroxytyrosol and oleuropein glucoside) were studied by end-channel amperometric detection using a 100 μm gold wire as working electrode in glass microchip electrophoresis. The electrochemical behavior of these compounds was studied and the medium to carry out their detection was selected (0.1 M aqueous sulfuric acid). The best conditions for the separation were achieved in sodium tetraborate (10% methanol, pH 9.50) with different concentrations for the sample and the running buffer in order to allow the sample stacking phenomenon. The injection was carried out using 600 V for 3 s and the separation voltage was set at 1000 V. The quality of the method was evaluated through its analytical figures of merit and by its performance on real extra virgin olive oil samples. Determination of these compounds was carried out using the standard addition calibration method with good recoveries.

  4. 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

  5. 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

  6. 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

  7. 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

  8. Identification and quantification of phenolic compounds in grapes by HPLC-PDA-ESI-MS on a semimicro separation scale.

    PubMed

    Nicoletti, Isabella; Bello, Cristiano; De Rossi, Antonella; Corradini, Danilo

    2008-10-08

    Reversed phase high performance liquid chromatography (RP-HPLC) on a semimicro separation scale was employed to develop a straightforward method for the simultaneous separation, identification, and quantification of phenolic compounds occurring in whole berries of Vitis vinifera, which comprise phenolic acids, flavonols, catechins, stilbenes, and anthocyanins. A C-18 narrow bore column of 150 x 2.0 mm I.D. and a semimicro photodiode array detector (PDA) cell of 2.5 microL, in conjunction with a mass spectrometry detector equipped with an electrospray ionization source (ESI-MS) to confirm peak identification, were employed. The C-18 narrow bore column was eluted by a multisegment gradient of increasing concentration of acetonitrile in water-formic acid solution that was optimized on the basis of the results of a study carried out to evaluate the influence of mobile phase composition and gradient shape on separation performance and detection sensitivity by ESI-MS. The identification of individual phenolic compounds was performed on the basis of their retention times and both UV-visible and mass spectra, acquired by a mass spectrometer (MS) equipped with an electrospray ionization (ESI) source, employed in conjunction with the PDA detector. Libraries comprising retention times, UV-visible, and mass spectra for major phenolic compounds expected in grape berries were made by subjecting solutions of each phenolic standard to the optimized RP-HPLC method. Quantification of individual compounds was performed by the external standard method using a six point regression graph of the UV-visible absorption data collected at the wavelength of maximum absorbance of each analyte determined by the PDA spectra. The RP-HPLC method was validated in terms of linearity of calibration graphs, limits of detection, limits of quantification, repeatability, and accuracy, which was evaluated by a recovery study. The developed method was successfully applied to identify the phenolic compounds

  9. Characterization of total antioxidant capacity and (poly)phenolic compounds of differently pigmented rice varieties and their changes during domestic cooking.

    PubMed

    Zaupa, Maria; Calani, Luca; Del Rio, Daniele; Brighenti, Furio; Pellegrini, Nicoletta

    2015-11-15

    In the recent years, the pigmented rice varieties are becoming more popular due to their antioxidant properties and phenolic content. In this study, we characterized the antioxidant capacity (TAC) and the phenolic profile in white, red and black rice varieties, and evaluated the effect of two cooking methods (i.e. "risotto" and boiling) on these compounds. Before the cooking, all the varieties contained several phenolic acids, whereas anthocyanins and flavonols were peculiar of black rice and flavan-3-ols of red rice. Among the rice varieties, the black had the highest TAC value. The content of (poly)phenolic compounds and TAC decreased after cooking in all three varieties, but to a lesser extent after the risotto method. As a consequence, the risotto cooking, which allows a complete absorption of water, would be a good cooking method to retain (poly)phenolic compounds and TAC in pigmented and non-pigmented whole-meal rice.

  10. 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.

  11. 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

    2012-07-04

    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.

  12. 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.

  13. 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

  14. Influence of coffee roasting on the incorporation of phenolic compounds into melanoidins and their relationship with antioxidant activity of the brew.

    PubMed

    Perrone, Daniel; Farah, Adriana; Donangelo, Carmen M

    2012-05-02

    In the present study, the influence of coffee roasting on free and melanoidin-bound phenolic compounds and their relationship with the brews' antioxidant activity (AA), evaluated by TRAP, TEAC, and TRAP, were investigated. Changes in the relative content of free chlorogenic acids (CGA), free lactones, and melanoidin-bound phenolic acids during roasting indicate that phenolic compounds were incorporated into melanoidins mainly at early stages of the process, being thereafter partly oxidized to dihydrocaffeic acid, and degraded. Although less than 1% of CGA in green coffee was incorporated into melanoidins during roasting, the relative content of melanoidin-bound phenolic acids increased significantly during this process, reaching up to 29% of total phenolic compounds in brews from dark roasted coffees. Regardless of the AA assay used and considering all roasting degrees, the overall contribution of CGA to the AA of the whole brews was higher than that of melanoidin-bound phenolic compounds. It was estimated that the latter compounds contributed to 25-47% of the AA, depending on the assay used.

  15. 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.

  16. Monitoring the phenolic compounds of Greek extra-virgin olive oils during storage.

    PubMed

    Kotsiou, Kali; Tasioula-Margari, Maria

    2016-06-01

    Extra virgin olive oil (EVOO) samples, of five Greek olive varieties, were stored in dark glass bottles (headspace 0.5%) in a basement without central heating for 24 months. Quantitative variations of the phenolic compounds and their degradation products were monitored over time. The differences observed in the initial total phenolic compounds concentration (ranging between 250.77 and 925.75 mg/kg) were attributed to extraction system, olive variety, and maturity stage. Even after 24 months, the degree of reduction in total phenolic compounds did not exceed 31%. The reduction was more pronounced in dialdehydic forms of oleuropein and ligstroside aglycones (DAFOA and DAFLA), indicating a more active participation in the hydrolysis and oxidation processes of the more polar secoiridoids. The initial total phenolic content was the main factor correlated to the degradation rate of the phenolic compounds. The decrease in secoiridoid derivatives, gave rise to hydroxytyrosol and tyrosol content and to the formation of four oxidized products.

  17. Optimisation of ultrasonic-assisted extraction of phenolic compounds, antioxidants, and anthocyanins from sugar beet molasses.

    PubMed

    Chen, Mingshun; Zhao, Yi; Yu, Shujuan

    2015-04-01

    Response surface methodology was used to optimise experimental conditions for ultrasonic-assisted extraction (UAE) of functional components from sugar beet molasses. The central composite design (CCD) was used for the optimisation of extraction parameters in terms of total phenolic contents, antioxidant activities and anthocyanins. Result suggested the optimal conditions obtained by RSM for UAE from sugar beet molasses were as follows: HCl concentration 1.55-1.72 mol/L, ethanol concentration 57-63% (v/v), extraction temperature 41-48 °C, and extraction time 66-73 min. In the optimal conditions, the experimental total phenolic contents were 17.36 mg GAE/100mL, antioxidant activity was 16.66 mg TE/g, and total anthocyanins were 31.81 mg/100g of the sugar beet molasses extract, which were well matched the predicted values. Teen compounds, i.e. gallic acid, vanillin, hydroxybenzoic acid, syringic acid, cyanidin-3-O-rutinoside, cyanidin-3-O-glucoside, catechin, delphinidin-3-O-rutinoside, delphinidin-3-O-glucuronide and ferulic acid were determined by HPLC-DAD-MS/MS in sugar beet molasses.

  18. Isolation of free phenolic compounds from arboreal leaves by use of the Florisil/C18 system.

    PubMed

    Jaroszyńska, Jadwiga

    2003-10-01

    In studies of the phenolic compounds present in leaves and needles, GC and GC-MS have so far been applied only sporadically. This is probably because of the greater difficulties encountered in preparing the samples for this method than those used for liquid chromatography. When preparing a sample for gas chromatography the analyst is faced with two difficult stages-separation of the compound from the matrix without losses (stage 1) so that the final sample can be derivatized to make it suitable for analysis on a non-polar capillary column of the gas chromatograph (stage 2). This paper presents a procedure for extraction of phenolic compounds from the matrix by means of a Florisil/C(18) sorbent system and their analysis by GC. After passage through the adsorbents the recovery ranges from 32% for ferulic acid to 88% for gentisic acid. It was found that this extraction method and the GC analysis are very precise (particularly for samples of a mass <1 g) and can be used for quantification. The high-precision quantification of 15 phenolic acids, shikimic acid, and six other compounds present in pine needles has been achieved. The conditions used for GC analysis and construction of calibration curves for quantitative determination are given.

  19. 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.

  20. Antioxidant activity of phenolic and related compounds: a density functional theory study on the O-H bond dissociation enthalpy.

    PubMed

    Giacomelli, Cristiano; Miranda, Fabio da Silva; Gonçalves, Norberto Sanches; Spinelli, Almir

    2004-01-01

    We report here on calculations at the hybrid DFT/HF (B3-LYP/6-31G(d, p)) level of the O-H bond dissociation enthalpy (O-H BDE) of phenylpropenoic acids (caffeic, ferulic, p-coumaric and cinnamic) and phenolic acids and related compounds (gallic, methylgallate, vanillic and gentisic) in order to gain insight into the understanding of structure-antioxidant activity relationships. The results were correlated and discussed mainly on the basis of experimental data in a companion work (Galato D, Giacomelli C, Ckless K, Susin MF, Vale RMR, Spinelli A. Antioxidant capacity of phenolic and related compounds: correlation among electrochemical, visible spectroscopy methods and structure-antioxidant activity. Redox Report 2001; 6: 243-250). The O-H BDE values showed remarkable dependence on the hydroxyl position in the benzene ring and the existence of additional interaction due to hydrogen bonding. For parent molecules, the experimental antioxidant activity (AA) order was properly obeyed only when intramolecular hydrogen bonding was present in the radicalized structures of o-dihydroxyl moieties. In structurally related compounds, excellent correlation with experimental data was in general observed (0.64 < rho < 0.99). However, it is shown that excellent correlation can also be obtained for this series of compounds considering p-radicalized structures which were not stabilized by intramolecular hydrogen bonding, but this had no physical meaning. These findings suggested that the antioxidant activity evaluation of phenolic and related compounds must take into consideration the characteristics of each particular compound.

  1. Two-season study of the influence of regulated deficit irrigation and reflective mulch on individual and total phenolic compounds of nectarines at harvest and during storage.

    PubMed

    Pliakoni, Eleni D; Nanos, George D; Gil, Maria I

    2010-11-24

    The influence of deficit irrigation (Deficit) and reflective mulch (Reflective) of Caldesi 2000 nectarines on the content of individual phenolic compounds was studied at harvest and during storage for 2, 4, and 6 weeks at 2 °C during two consecutive years (2007 and 2008). Individual phenolic groups in the edible fruit part consisted mainly of proanthocyanidins (200 mg/100 g fw), lower content of phenolic acids (17 mg/100 g fw), and minor content of flavonols (5 mg/100 g fw) and anthocyanins (1.2 mg/100 g fw). Deficit irrigation increased the content of total phenolics, including proanthocyanidins and phenolic acids, reaching similar amounts in both years. Sun-exposed fruit (upper part of canopy) showed higher content than shaded fruit (lower part of canopy). However, Reflective significantly increased the content of total phenolics, particularly phenolic acids and proanthocyanidins, of fruit located in the lower part of the canopy. During storage, Deficit and Reflective did not affect the content of phenolic acids, flavonols, and proanthocyanidins when compared to the content at harvest. Optimizing cultural practices can be a way to increase the phenolic content of nectarines.

  2. Phenolic compounds of Brazilian beers from different types and styles and application of chemometrics for modeling antioxidant capacity.

    PubMed

    Moura-Nunes, Nathália; Brito, Thárcila Cazaroti; da Fonseca, Nívea Dias; de Aguiar, Paula Fernandes; Monteiro, Mariana; Perrone, Daniel; Torres, Alexandre Guedes

    2016-05-15

    In the present study we aimed at investigating, for the first time, phenolic compounds in Brazilian beers of different types and styles. We also aimed at applying chemometrics for modeling beer's antioxidant capacity as a function of their physicochemical attributes (density, refractive index, bitterness and ethanol content). Samples (n=29) were analyzed by PCA originating five groups, especially according to ethanol contents and bitterness. In general, Group V (alcoholic beers with very high bitterness) presented higher refractive index, bitterness, ethanol and phenolics contents than Groups I (non-alcoholic beers) and II (alcoholic beers with low bitterness). Brazilian beers phenolics profile was distinct from that of European beers, with high contents of gallic acid (0.5-14.7 mg/L) and low contents of ferulic acid (0.2-1.8 mg/L). Using PLS, beer's antioxidant capacity measured by FRAP assay could be predicted with acceptable precision by data of ethanol content and density, bitterness and refractive index values.

  3. 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.

  4. Adsorption and detection of some phenolic compounds by rice husk ash of Kenyan origin.

    PubMed

    Mbui, Damaris N; Shiundu, Paul M; Ndonye, Rachel M; Kamau, Geoffrey N

    2002-12-01

    Rice husk ash (RHA) obtained from a rice mill in Kenya has been used as an inexpensive and effective adsorbent (and reagent) for the removal (and detection) of some phenolic compounds in water. The abundantly available rice mill waste was used in dual laboratory-scale batch experiments to evaluate its potential in: (i) the removal of phenol, 1,3-dihydroxybenzene (resorcinol) and 2-chlorophenol from water; and (ii) the detection of 1,2-dihydroxybenzene (pyrocatechol) and 1,2,3-trihydroxybenzene (pyrogallol) present in an aqueous medium. The studies were conducted using synthetic water with different initial concentrations of the phenolic compounds. The effects of different operating conditions (such as contact time, concentration of the phenolic compounds, adsorbent quantity, temperature, and pH) were assessed by evaluating the phenolic compound removal efficiency as well as the extent of their color formation reactions (where applicable). RHA exhibits reasonable adsorption capacity for the phenolic compounds and follows both Langmuir and Freundlich isotherm models. Adsorption capacities of 1.53 x 10(-4), 8.07 x 10(-5), and 1.63 x 10(-6) mol g(-1) were determined for phenol, resorcinol and 2-chlorophenol, respectively. Nearly 100% adsorption of the phenolic compounds was possible and this depended on the weight of RHA employed. For the detection experiments, pyrocatechol and pyrogallol present in water formed coloured complexes with RHA, with the rate of colour formation increasing with temperature, weight of RHA, concentration of the phenolic compounds and sonication. This study has proven that RHA is a useful agricultural waste product for the removal and detection of some phenolic compounds.

  5. Determination of phenolic compounds and hydroxymethylfurfural in meads using high performance liquid chromatography with coulometric-array and UV detection.

    PubMed

    Kahoun, David; Rezková, Sona; Veskrnová, Katerina; Královský, Josef; Holcapek, Michal

    2008-08-15

    The objective of this study was the determination of 25 phenolic compounds in different mead samples (honeywines) using high performance liquid chromatography (HPLC) with coulometric-array detection and in case of hydroxymethylfurfural with UV detection. Our method was optimized in respect to both the separation selectivity of individual phenolic compounds and the maximum sensitivity with the electrochemical detection. The method development included the optimization of mobile phase composition, the pH value, conditions of the gradient elution and the flow rate using a window-diagram approach. The developed method was used for the determination of limits of detection and limits of quantitation for individual compounds. The linearity of calibration curves, accuracy and precision (intra- and inter-day) at three concentration levels (low, middle and high concentration range) were verified. Mead samples were diluted with the mobile phase at 1:1 to 1:50 ratio depending on the concentration and filtered through a PTFE filter without any other sample pre-treatment. Phenolic compounds concentration was determined in 50 real samples of meads and correlated with meads composition and hydroxymethylfurfural concentration. The most frequently occurred compounds were protocatechuic acid and vanillic acid (both of them were present in 98% samples), the least occurred compounds were (+)-catechin (10% samples) and sinapic acid (12% samples). Vanillin and ethylvanillin, which are used as artificial additives for the taste improvement, were found in 60% and 42% samples, respectively. Hydroxymethylfurfural concentration, as an indicator of honey quality, was in the range from 2.47 to 158 mg/L. Our method is applicable for the determination of 25 phenolic compounds in mead, honey and related natural samples.

  6. Simultaneous estimation of phenolic acids in sea buckthorn (Hippophaë rhamnoides) using RP-HPLC with DAD.

    PubMed

    Arimboor, Ranjith; Kumar, K Sarin; Arumughan, C

    2008-05-12

    A RP-HPLC-DAD method was developed and validated for the simultaneous analysis of nine phenolic acids including gallic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, salicylic acid, p-coumaric acid, cinnamic acid, caffiec acid and ferulic acid in sea buckthorn (SB) (Hippophaë rhamnoides) berries and leaves. The method was validated in terms of linearity, LOD, precision, accuracy and recovery and found to be satisfactory. Phenolic acid derivatives in anatomical parts of SB berries and leaves were separated into free phenolic acids, phenolic acids bound as esters and phenolic acids bound as glycosides and profiled in HPLC. Berry pulp contained a total of 1068 mg/kg phenolic acids, of which 58.8% was derived from phenolic glycosides. Free phenolic acids and phenolic acid esters constituted 20.0% and 21.2%, respectively, of total phenolic acids in SB berry pulp. The total phenolic acid content in seed kernel (5741 mg/kg) was higher than that in berry pulp and seed coat (Table 2). Phenolic acids liberated from soluble esters constituted the major fraction of phenolic acids (57.3% of total phenolic acids) in seed kernel. 8.4% and 34.3% of total phenolic acids in seed kernel were, respectively contributed by free and phenolic acids liberated from glycosidic bonds. The total soluble phenolic acids content in seed coat (448 mg/kg) was lower than that in seed kernel and pulp (Table 2). Proportion of free phenolic acids in total phenolic acids in seed coat was higher than that in seed kernel and pulp. Phenolic acids bound as esters and glycosides, respectively contributed 49.1% and 20.3% of total phenolic acids in seed coat. The major fraction (approximately 70%) of phenolic acids in SB berries was found to be concentrated in the seeds. Gallic acid was the predominant phenolic acid both in free and bound forms in SB berry parts and leaves.

  7. Effect of dietary phenolic compounds on apoptosis of human cultured endothelial cells induced by oxidized LDL

    PubMed Central

    Vieira, Otilia; Escargueil-Blanc, Isabelle; Meilhac, Olivier; Basile, Jean-Pierre; Laranjinha, Joao; Almeida, Leonor; Salvayre, Robert; Nègre-Salvayre, Anne

    1998-01-01

    Oxidized low density lipoproteins (LDL) are toxic to cultured endothelial cells. Mildly oxidized LDL, characterized by relatively low levels of TBARS and only minor modifications of apoB, were obtained by using 2 experimental model systems of oxidation, namely oxidation by u.v. radiation or ferrylmyoglobin (a two electron oxidation product from the reaction of metmyoglobin with H2O2). Toxic concentrations of mildly oxidized LDL induce apoptosis (programmed cell death) of cultured endothelial cells, as shown by typical morphological features, by the in situ TUNEL procedure and by DNA fragmentation revealed on gel electrophoresis. This apoptosis is calcium-dependent and subsequent to the intense and sustained cytosolic [Ca2+]i peak elicited by oxidized LDL. Five naturally occurring phenolic compounds present in food and beverages were able to prevent, in a concentration-dependent manner, the apoptosis of endothelial cells induced by oxidized LDL. Among the compounds tested, caffeic acid was the most effective. Under the conditions used, the protective effect of caffeic acid (IC50 8.3±2.1 μmol  l−1) in the prevention of apoptosis induced by oxidized LDL was significantly higher than that of the other compounds tested (IC50s were 12.4±3.2, 14.1±4.1, 20.4±4.4 and 72.6±9.2 μmol  l−1 for ferulic, protocatechuic, ellagic and p-coumaric acids, respectively). The anti-apoptotic effect of caffeic acid results from the addition of two effects, (i) the antioxidant effect which prevents LDL oxidation and subsequent toxicity (‘indirect' protective effect); (ii) a ‘direct' cytoprotective effect, acting at the cellular level. Effective concentrations of caffeic acid acted at the cellular level by blocking the intense and sustained cytosolic [Ca2+]i rise elicited by oxidized LDL. In conclusion, phenolic acids (caffeic and ferulic acids being the most potent of the compounds tested under the conditions used) exhibit a potent cytoprotective effect of

  8. 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.

  9. 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....

  10. Phenol biosynthesis in higher plants. Gallic acid

    PubMed Central

    Dewick, P. M.; Haslam, E.

    1969-01-01

    The biosynthesis of gallic acid in a number of higher plants was investigated by using l-[U-14C]phenylalanine, (−)-[G-14C]shikimic acid, d-[1-14C]glucose and d-[6-14C]glucose as tracers. The results are compared with those obtained similarly for caffeic acid and are interpreted in terms of the dehydrogenation of 5-dehydroshikimic acid as a normal route of metabolism for gallic acid. PMID:5807212

  11. Formulation of Propolis Phenolic Acids Containing Microemulsions and Their Biopharmaceutical Characterization

    PubMed Central

    2016-01-01

    Microemulsions (MEs) were formulated using PEG-8 caprylic/capric glycerides and ethanolic propolis extracts. Characterization of MEs was performed by determining mean droplet size, polydispersity index, stability under varying external factors, and formulation effect on delivery of phenolic compounds into the skin ex vivo. Essential oils were included into the formulations of MEs and their influence on physical characteristics of the nanostructured systems as well as penetration into epidermis and dermis were evaluated. The droplet size, their distribution, and stability of the formulated MEs were not affected. Presence of essential oils in the formulation increased penetration of phenolic compounds in general, but only the amount of ferulic acid increased significantly. Mean droplet size increased with increase of oily phase amount, suggesting that phenolic compounds and components of essential oils were not modifying the formation of the interphase film composition and/or structure. Phenolic compounds were predominantly located in the lipid phase of the MEs thus minimizing their availability at the surface of the skin. PMID:27885330

  12. First Approach to the Analytical Characterization of
Barrel-Aged Grape Marc Distillates Using Phenolic Compounds and Colour Parameters

    PubMed Central

    Rodríguez-Solana, Raquel; Salgado, José Manuel; Domínguez, José Manuel

    2014-01-01

    Summary Phenolic compounds (benzoic and cinnamic acid derivatives) were determined by high-performance liquid chromatography with multiple wavelength detector (HPLC- -MWD) in grape marc distillates aged in Quercus petraea, Quercus robur and Quercus alba wooden barrels. In addition to colour indices and evaluable polyphenols, all samples were described by sensorial analysis. There were significant differences in the mean concentrations of the majority of phenolic compounds among the samples. Gallic and benzoic acids were the most abundant and samples aged in Q. robur from Galicia (NW of Spain) had the highest concentration of most of the determined phenols. Grape marc distillates aged in Q. robur obtained the highest values of all sensorial attributes, whereas samples aged in Q. petraea and Q. alba obtained similar scores. Principal component analysis accounted for 88.32% of total variance, showing a good separation of aged distillates in terms of phenolic compounds and colour characteristics, according to the species and origin of the oak wood used in the ageing process. PMID:27904312

  13. Competitive adsorption of furfural and phenolic compounds onto activated carbon in fixed bed column.

    PubMed

    Sulaymon, Abbas H; Ahmed, Kawther W

    2008-01-15

    For a multicomponent competitive adsorption of furfural and phenolic compounds, a mathematical model was builtto describe the mass transfer kinetics in a fixed bed column with activated carbon. The effects of competitive adsorption equilibrium constant, axial dispersion, external mass transfer, and intraparticle diffusion resistance on the breakthrough curve were studied for weakly adsorbed compound (furfural) and strongly adsorbed compounds (parachlorophenol and phenol). Experiments were carried out to remove the furfural and phenolic compound from aqueous solution. The equilibrium data and intraparticle diffusion coefficients obtained from separate experiments in a batch adsorber, by fitting the experimental data with theoretical model. The results show that the mathematical model includes external mass transfer and pore diffusion using nonlinear isotherms and provides a good description of the adsorption process for furfural and phenolic compounds in a fixed bed adsorber.

  14. Synthesis and evaluation of antioxidant and antifungal activities of novel ricinoleate-based lipoconjugates of phenolic acids.

    PubMed

    Reddy, Kunduru Konda; Ravinder, Thumu; Kanjilal, Sanjit

    2012-10-15

    Syntheses of four castor oil fatty acid-based novel lipoconjugates of phenolic acids were carried out following Mitsunobu methodology. The lipid part consists of methyl ricinoleate and its saturated analogue, methyl-12-hydroxystearate and the phenolic moieties are ferulic and vanillic acid. Synthesised compounds are evaluated for antioxidant activity using three in vitro assays (DPPH radical scavenging assay, DSC studies for oxidative induction temperature of linoleic acid and autoxidation of linoleic acid in Tween 20 micellar medium) and compared with three widely used antioxidants in the food industry, BHT, α-tocopherol, and dodecyl gallate. Synthesised compounds are found to exhibit good antiradical activity. These compounds also exhibited very good antifungal activity against studied fungal strains. All these results suggested the applicability of the synthesised compounds as potent lipophilic antioxidants for combating oxidative stress.

  15. Optimisation of ultrasound assisted extraction of phenolic compounds from Sparganii rhizoma with response surface methodology.

    PubMed

    Wang, Xinsheng; Wu, Yanfang; Chen, Guangyun; Yue, Wei; Liang, Qiaoli; Wu, Qinan

    2013-05-01

    The present study reports on the extraction of phenolic compounds from sparganii rhizome. Box-Behnken Design (BBD), a widely used form of response surface methodology (RSM), was used to investigate the effect of process variables on the ultrasound-assisted extraction (UAE). Three independent variables including ethanol concentration (%), extraction time (min) and solvent-to-material ratio (mL/g) were studied. The results showed that the optimal UAE condition was obtained with an ethanol concentration of 75.3%, an extraction time of 40min and a solvent-to-material ratio of 19.21mL/g for total phenols, and an ethanol concentration of 80%, an extraction time of 33.54min and solvent-to-material ratio of 22.72mL/g for combination of ρ-hydroxybenzaldehyde, ρ-coumaric acid, vanillic acid, ferulic acid, rutin and kaempferol. The experimental values under optimal conditions were in good consistent with the predicted values, which suggested UAE is more efficient process as compared to solvent extraction.

  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. Spectroscopic and theoretical investigations of phenolic acids in white wines.

    PubMed

    Martin, Coralie; Bruneel, Jean-Luc; Castet, Frédéric; Fritsch, Alain; Teissedre, Pierre-Louis; Jourdes, Michael; Guillaume, François

    2017-04-15

    Model solutions of white wines containing phenolic acids have been investigated by means of UV-vis, laser induced fluorescence and Raman spectroscopic techniques. In order to interpret the spectra, density functional theory calculations of phenolic acids have been performed. This work demonstrates that only hydroxynamic acids are in resonance with a laser excitation line with 325nm wavelength and are therefore at the origin of the strong enhancement of the Raman light scattering. Real white wines also display such resonance Raman scattering so that their content in hydroxycinnamic acids may be quite precisely determined. The analysis of the Raman spectrum of a real dry white wine reveals qualitatively the preponderance in its composition of p-coumaric and caftaric acids.

  18. 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.

  19. Comparison of the phenolic compounds, carotenoids and tocochromanols content in wheat grain under organic and mineral fertilization regimes.

    PubMed

    Konopka, Iwona; Tańska, Małgorzata; Faron, Alicja; Stępień, Arkadiusz; Wojtkowiak, Katarzyna

    2012-10-19

    A field study was performed to evaluate the effect of mineral (NPK) and organic-based fertilizers such as compost (C), manure (FYM) and meat and bone meal (MBM) on the appearance (dimensions and color) of spring wheat kernels and on the total content in grain of main its phytochemicals (polyphenols, carotenoids and tocochromanols) and phenolic acids composition. Total phenolic compounds were determined using the Folin-Ciocalteu assay after alkaline hydrolysis of grain and carotenoids were analyzed spectrophotometrically. Composition of tocochromanols and phenolic acids was determined using RP-HPLC techniques. Only insignificant differences in the appearance of kernels and small changes in the content and composition of grain phytochemicals were noted between the studied fertilization systems. Among the analyzed phytochemicals the greatest variation was observed in the group of polyphenol compounds, with a stated increase of their total content of 6.7 and 11.2% in grain fertilized with MBM and compost, respectively. Simultaneously the grain from organic fertilization contained significantly less phenolic acids, and the decrease in their content ranged from 10.0% for FYM to 24.8% for MBM+EM-1. Organically and conventionally fertilized grain had similar amounts of tocochromanols and carotenoids. Comparison of MBM and MBM+EM-1 variants showed that application of effective microorganisms decreased carotenoids and tocochromanols content by 8.5 and 9.7%, respectively.

  20. Phenolic compounds responding to zinc and/or cadmium treatments in Gynura pseudochina (L.) DC. extracts and biomass.

    PubMed

    Mongkhonsin, Bodin; Nakbanpote, Woranan; Hokura, Akiko; Nuengchamnong, Nitra; Maneechai, Suthira

    2016-12-01

    Gynura pseudochina (L.) DC. is a Zn/Cd hyperaccumulative plant. In an in vivo system under controlled plant age, this research reveals that phenolic compounds and lignification play beneficial roles in protecting G. pseudochina from exposure to an excess of Zn and/or Cd, and Zn reduces Cd toxicity under the dual treatments. The total phenolic content (TPC), total flavonoid content (TFC), and half-maximal inhibitory concentration (IC50) values correspond to the metal dose-response curves. Liquid chromatography-electrospray ionization-quadrupole time of flight-tandem mass spectrometry (LC-ESI-QTOF-MS/MS) is used to characterize phenolic compounds and their glycosides, which could play roles in antioxidant activities and in the esterification of the cell wall, especially derivatives of p-coumaric and caffeic acid. Confocal laser scanning microscopy (CLSM) and micro X-ray fluorescence (μ-XRF) imaging revealed that the accumulation of Zn and Cd in the cell wall involves flavonoid compounds. Low extractable pools of Cd and Zn in the leaf extracts indicate that these elements are tightly bound to the plant biomass structures. The bulk X-ray absorption near edge structure (XANES) spectra indicate that Zn(2+) and Cd(2+) dominate with O and S ligands, which could be provided by cell walls, phenolic compounds, and sulphur protein. Consequently, the benefit of these results is to support the growth of G. pseudochina for phytoremediation in a Zn- and/or Cd-contaminated site.

  1. RP-HPLC analysis of phenolic compounds and flavonoids in beverages and plant extracts using a CoulArray detector.

    PubMed

    Jandera, Pavel; Skeifíková, Veronika; Rehová, Lucie; Hájek, Tomás; Baldriánová, Lucie; Skopová, Gabriela; Kellner, Vladimír; Horna, Ales

    2005-06-01

    Methods were developed for the analysis of natural antioxidants including phenolic compounds and flavonoids in beverages and plant extracts using gradient HPLC with multi-channel electrochemical coulometric detection. Suitability of various reversed-phase columns for this purpose was compared; pH and mobile phase gradients were optimized with respect to the separation selectivity and sensitivity of detection. Because of different target compounds in various sample types, the overlapping resolution maps and the normalized resolution product approaches described earlier were used to select optimum columns and gradients to suit the analysis of the individual sample types. The methods were applied to the analysis of phenolic compounds and flavonoids in beer, wine, tea, and yacon extracts. 32 phenolic compounds were identified and determined, including derivatives of benzoic and cinnamic acids, flavones, and a few related glycosides. Eight-channel CoulArray detection offers high selectivity and sensitivity with limits of detection in the low microg L(-1) range, at least an order of magnitude lower than single-channel coulometric detection using the Coulochem detector. No special sample pretreatment is necessary and, because of the compatibility of the CoulArray detector with gradient elution, phenolic antioxidants of different polarities can be determined in a single run. In addition to the retention times, the ratios of the areas of the pre-dominant and post-dominant peaks to the area of the dominant peak can be used for improved identification of natural antioxidants.

  2. Quantification of phenolic acids and their methylates, glucuronides, sulfates and lactones metabolites in human plasma by LC-MS/MS after oral ingestion of soluble coffee.

    PubMed

    Marmet, Cynthia; Actis-Goretta, Lucas; Renouf, Mathieu; Giuffrida, Francesca

    2014-01-01

    Chlorogenic acids and derivatives like phenolic acids are potentially bioactive phenolics, which are commonly found in many foods. Once absorbed, chlorogenic and phenolic acids are highly metabolized by the intestine and the liver, producing glucuronidated and/or sulphated compounds. These metabolites were analyzed in human plasma using a validated liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) method. After protein precipitation, phenolic acids and their metabolites were extracted by using ethanol and chromatographic separation was achieved by reversed-phase using an Acquity UPLC BEH C18 column combined with a gradient elution system using 1% acetic acid aqueous solution and 1% acetic acid with 100% acetonitrile. The method was able to quantify 56 different compounds including 24 phenolic acids, 4 lactones, 15 sulfates and 13 glucuronides metabolites between 5 and 1000nM in plasma for most of them, except for m-dihydrocoumaric acid, 5-ferulloylquinic-glucuronide, 4-methoxycinnamic acid, 3-phenylpropionic acid, 3-(4-methoxyphenyl)propionic acid (25 to 1000nM) and p-dihydrocoumaric acid (50-1000nM). Values of repeatability and intermediate reproducibility were below 15% of deviation in general, and maximum 20% for the lowest concentrations. The validated method was successfully applied to quantify phenolic acids and their metabolites in plasma obtained after oral ingestion of soluble coffee. In conclusion, the developed and validated method is proved to be very sensitive, accurate and precise for the quantification of these possible dietary phenols.

  3. 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.

  4. Comparison between sample disruption methods and solid-liquid extraction (SLE) to extract phenolic compounds from Ficus carica leaves.

    PubMed

    Teixeira, D Martins; Patão, R Ferreira; Coelho, A Varela; da Costa, C Teixeira

    2006-01-20

    Sea sand disruption method (SSDM) and matrix solid phase disruption (MSPD) were compared to solid-liquid extraction (SLE) for extraction of phenolic compounds from the Ficus carica leaves. Statistical treatment, ANOVA-single factor, was used to compare the extraction yields obtained by these methods, and for the majority of the extracted compounds, significantly higher yields were obtained by the solid disruption methods. Both solid disruption methods are faster and ecologically friendly, but the sea sand method was more reproducible (RSD < 5% for most compounds), and was also the least expensive method. Recoveries above 85% were obtained for chlorogenic acid, rutin, and psoralen using the sea sand extraction method.

  5. A review and investigation of the effect of nanophotocatalytic ozonation process for phenolic compound removal from real effluent of pulp and paper industry.

    PubMed

    Biglari, Hamed; Afsharnia, Mojtaba; Alipour, Vali; Khosravi, Rasoul; Sharafi, Kiomars; Mahvi, Amir Hossein

    2017-02-01

    Phenol and its derivatives are the major environmental pollutants discharged from paper and pulp industries into water bodies. All these compounds and chlorinated phenolic compounds in particular are very toxic to fauna and flora, even at relatively low concentration. This study aimed to investigate the removal rate of phenolic compounds from the effluent of pulp and paper industries using a combination of ozonation and photocatalytic processes. Firstly, a certain volume from the effluent of paper and pulp industries containing certain phenol concentrations was obtained and fed into a prefabricated reactor at laboratory scale. Then, the combined and separate effects of zinc oxide dosage (ZnO), ozone flow rate (O3), and pH under ultra violet radiation for 30 min were evaluated. The concentration of phenolic compounds and the produced ozone gas flow rate were measured by a spectrophotometry and iodometric method, respectively. The results showed that the phenolic removal rate increased at acidic PHs compared with alkaline PHs; it was also decreased with the increase in ZnO dosages. Furthermore, the highest phenolic compound's removal rate was 99% at the optimal condition (pH 5, ZnO dosage of 0.1 g L(-1) at the 30 min with UV-C illumination of 125 W). Finally, Daphnia toxicity test showed that treated effluent was safe and met the standards to the extent that it can be discharged into the receiving waters. Graphical abstract ᅟ.

  6. Effect of removal of phenolic compounds on structural and thermal properties of sunflower protein isolate.

    PubMed

    Malik, M A; Sharma, H K; Saini, C S

    2016-09-01

    The present study evaluated the effect of removal of polyphenols on the structural properties of protein isolates extracted from sunflower seed and kernel. The structural and thermal changes in protein upon phenolic interaction were studied using circular dichroism, differential scanning calorimetry, thermal gravimetric analysis, X-ray diffraction, sodium dodecyl sulphate-polyacrylamide gel electrophoresis (SDS-PAGE), and Fourier Transform Infrared (FT-IR) spectroscopy. Presence of phenolic compounds in proteins decreased the ordered structure content with parallel increase in unordered structure content. Denaturation temperature was higher for protein isolates with phenolic compounds while, enthalpy decreased upon phenolic interaction. In the presence of phenolic compounds, higher mass loss was observed upon heating. Crystalinity and crystal size got increased after removal of phenolic compounds. Protein isolates from kernels had higher percentage of crystalinity and crystal size as compared to seed protein isolates. Higher molecular weights were observed for protein isolates with phenolic compounds. Presence of polyphenols reduced the hydrophobicity as well the sulfhydryl content and increased the particle size of proteins.

  7. In vitro bioavailability of phenolic compounds from five cultivars of frozen sweet cherries (Prunus avium L.).

    PubMed

    Fazzari, Marco; Fukumoto, Lana; Mazza, Giuseppe; Livrea, Maria A; Tesoriere, Luisa; Marco, Luigi Di

    2008-05-28

    The bioavailability of phenolic compounds from five cultivars of frozen sweet cherries was assessed by a digestion process involving pepsin-HCl digestion (to simulate gastric digestion) and pancreatin digestion with bile salts (to simulate small intestine conditions) and dialyzed to assess serum- and colon-available fractions. After pepsin digestion, the % recovery of total phenolics, relative to the original starting material, increased, whereas the % anthocyanins did not change. Following pancreatic digestion and dialysis, the total phenolics in the IN (serum-available) fraction was about 26-30% and the OUT (colon-available) fraction was about 77-101%. The anthocyanin content in the IN fraction was 15-21%, and in the OUT fraction, it was 52-67%. Skeena, Lapins, and Sweetheart cultivars contained higher levels of total phenolics and anthocyanins, which resulted in higher concentrations of these compounds in the IN and OUT fractions. The potential bioavailability of phenolic compounds was also assessed in Bing and Lapins cultivars at three ripening stages. Immature cherries had higher % total phenolics in the IN fraction than mature or overmature cherries. However, immature cherries had the lowest concentrations of these compounds, making the actual bioavailable amounts of these compounds lower than for mature and overmature fruit. High-performance liquid chromatography analysis of Lapins cherries at three maturity stages confirmed the results obtained using spectrophotometric methods for total phenolics and anthocyanins.

  8. Profiling and elucidation of the phenolic compounds in the aerial parts of Gynura bicolor and G. divaricata collected from different Chinese origins.

    PubMed

    Chen, Jian; Mangelinckx, Sven; Lü, Han; Wang, Zheng-Tao; Li, Wei-Lin; De Kimpe, Norbert

    2015-01-01

    Gynura bicolor and G. divaricata are not only known to be nutritive as cultured vegetables, but also beneficial as folk medicines in East Asia. As demonstrated by the current phytochemical knowledge, the genus Gynura is a promising source of phenolics with multiple medicinal activities. To expand this phytochemical knowledge, the phenolic secondary metabolites of G. bicolor and G. divaricata were studied. From the aerial parts of these two species, collected in five different Chinese locations, two fractions of phenolic compounds with different polarity were obtained by extraction and chromatographic separation. Using UPLC/MS/MS analysis, a total of 53 phenolics were either identified by comparison with respective reference compounds or tentatively characterized by their chromatographic behavior, UV-absorption patterns, and MS fragmentations. Some naturally existing positional isomers of O-caffeoylquinic acid, O-p-coumaroylquinic acid, O-feruloylquinic acid, and dicaffeoylquinic acid as well as their methyl esters were qualitatively characterized by their specific fragmentation patterns in targeted MS/MS. In addition, the aerial parts of the two Gynura species contained kaempferol, quercetin oligoglycosides, and a variety of derivatives of benzoic acid, hydroxycinnamic acid, and caffeic acid. Furthermore, the distribution of phenolic compounds in the two species from different Chinese origins was discussed. Finally, an investigation of the total phenolic content and in vitro antioxidant activity of the various phenolic fractions was completed, to evaluate the potential of the extracts of these species for medicinal development. The free-radical-scavenging activities of the extracts derived from plants originating from Nanjing were proven to be higher than those of the other extracts, which correlated well with their total phenolic content.

  9. Kinetics of the reaction between ozone and phenolic acids present in agro-industrial wastewaters.

    PubMed

    Beltran-Heredia, J; Torregrosa, J; Dominguez, J R; Peres, J A

    2001-03-01

    The kinetics of the ozonation of three phenolic acids is investigated from ozone absorption experiments in a semi-continuous reactor. After the evaluation of stoichiometric ratios for the individual reactions between ozone and each phenolic acid, the oxidation of p-hydroxybenzoic acid by ozone is performed in a first stage. The influence of the operating variables on the degradation process is established, and the application of a mass transfer with chemical reaction model based on the film theory leads to the determination of the reaction orders and kinetic rate constants. The experimental absorption rates obtained agree well with those calculated theoretically. In the second stage, a mixture of ferulic acid (4-hydroxy-3-methoxycinnamic acid), beta-resorcylic acid (2,4-dihydroxybenzoic acid) and p-hydroxybenzoic acid is ozonated under different experimental conditions. The kinetic study is performed by means of a competitive method that takes p-hydroxybenzoic acid as reference compound. The application of this model allows to determine the kinetic rate constants for each compound, which are correlated as a function of pH and temperature. The results obtained support that the kinetic regime of absorption is fast and pseudo-first order with respect to ozone, a condition required by the competitive method used.

  10. Determination of seven phenolic compounds in Rhizoma Sparganii by RP-HPLC.

    PubMed

    Wang, Xinsheng; Wu, Qi-nan; Wu, Yanfang; Wu, Chengying; Yue, Wei; Liang, Qiaoli

    2013-04-01

    A reversed-phase high-performance liquid chromatographic method was developed for the simultaneous quantification of seven phenolic compounds from Rhizoma Sparganii. The samples were separated on a Waters SunFire C18 column with a temperature of 30°C. Gradient elution was applied, using 0.8% acetic acid (solvent A) and methanol (solvent B) with a flow rate of 1.0 mL/min, and detection wavelength was 280 nm. The validation of the method included linearity, precision, repeatability, stability and recovery. The calibration curves showed good linear regression (R(2) > 0.9996) within the test range. The developed method indicated good precision and accuracy, with the overall intra-day and inter-day variation at less than 3%. The range of recoveries for the seven analytes was 95.34-100.06% with relative standard deviation < 3.08 %. The established method was successfully applied for the determination of seven phenolic compounds in 12 batches of Rhizoma Sparganii. The study may be useful in the quality evaluation of Rhizoma Sparganii, and can provide technical support for pharmacological and clinical research of related drugs.

  11. The roasting process does not influence the extent of conjugation of coffee chlorogenic and phenolic acids.

    PubMed

    Sanchez-Bridge, Belén; Renouf, Mathieu; Sauser, Julien; Beaumont, Maurice; Actis-Goretta, Lucas

    2016-05-01

    Understanding the bioavailability and metabolism of coffee compounds will contribute to identify the unknown biological mechanism(s) linked to their beneficial effects. The influence of the roasting process on the metabolism of coffee chlorogenic acids in humans was evaluated. In a randomized, double-blind, crossover study, 12 healthy volunteers consumed four instant coffees namely, high roasted coffee (HRC), low roasted coffee (LRC), unroasted coffee (URC), and in vitro hydrolyzed unroasted coffee (HURC). The sum of areas under the curve (AUC) ranged from 8.65-17.6 to 30.9-126 µM/h (P < 0.05) for HRC, LRC, URC, and HURC, respectively. The AUC of HRC, LRC, and URC was correlated with the initial level of phenolic acids in the coffee drinks. Despite different absorption rates, the extent of conjugation was comparable between HRC, LRC, and URC coffees but different for HURC. The most abundant circulating metabolites during the first 5 H were dihydroferulic acid (DHFA), caffeic acid-3'-O-sulfate (CA3S) and isoferulic-3'-O-glucuronide (iFA3G). DHFA and 5-4-dihydro-m-coumaric acid (mDHCoA) were the main metabolites in the period of 5-24 H. The phenolic compounds after consumption of HURC were most rapidly absorbed (Tmax 1 H) compared with the other coffees (Tmax between 9 and 11 H). Using coffees with different degrees of roasting we highlighted that in spite of different absorption rates the extent of conjugation of phenolic acids was comparable. In addition, by using a hydrolyzed unroasted coffee we demonstrated an increased absorption of phenolic acids in the small intestine. © 2016 BioFactors, 42(3):259-267, 2016.

  12. 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

  13. 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.

  14. Analysis of phenolic compounds from corn, oat, and wheat bran extracts by LC-MS-PDA

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phenolic compounds are among the most common secondary metabolites produced by plants and can exhibit a range of bioactive properties including antimicrobial, antioxidant, and antihypertensive. These natural products have applications in nutraceutical, pharmaceutical and functional food or animal fe...

  15. 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.

  16. LC-MS analysis of phenolic compounds and antioxidant activity of buckwheat at different stages of malting.

    PubMed

    Terpinc, Petra; Cigić, Blaž; Polak, Tomaž; Hribar, Janez; Požrl, Tomaž

    2016-11-01

    The impact of malting on the profile of the phenolic compounds and the antioxidant properties of two buckwheat varieties was investigated. The highest relative increases in phenolic compounds were observed for isoorientin, orientin, and isovitexin, which are consequently major inducible phenolic compounds during malting. Only a minor relative increase was observed for the most abundant phenolic compound, rutin. The radical-scavenging activity of buckwheat seeds was evaluated using ABTS and DPPH assays. A considerable increase in total phenolic compounds and higher antioxidant activity were observed after 64h of germination, whereas kilning resulted in decreased total phenolic compounds and antioxidant activity. Higher antioxidant activities for extracts were found for buffered solvents than for pure methanol and water. Changes in the composition of the phenolic compounds and increased antioxidant content were confirmed by several methods, indicating that buckwheat malt can be used as a food rich in antioxidants.

  17. Flavonoids and Other Phenolic Compounds in Needles of Pinus peuce and Other Pine Species from the Macedonian Flora.

    PubMed

    Karapandzova, Marija; Stefkov, Gjose; Cvetkovikj, Ivana; Stanoeva, Jasmina Petreska; Stefova, Marina; Kulevanova, Svetlana

    2015-06-01

    Flavonoids and other phenolic compounds in young needles of four pine species, Pinus peuce, P. nigra, P. mugo and P. sylvestris from the Macedonian flora were investigated. The amount of total phenols and total flavonoids were determined using Folin-Ciocalteau and aluminum chloride assay, respectively. The obtained results revealed that the total phenolic content (TPC) and total flavonoids content (TFC) varied among different pine species ranging from 9.8 to 14.0 mg GAE/g and from 3.3 to 7.2 mg CE/g of dried plant material, respectively. Qualitative analysis of flavonoids and other phenolic components was made by a LC-DAD/ESI-MS(n) optimized chromatographic method. A total of 17 phenolic components were identified and classified as: acids (2), procyanidins (2) and flavonoid glycosides (13). The most prevalent components were flavonoid glycosides, especially flavonols and methylated flavonols (9). Additionally, 3 components were found as acylated flavonol glycosides with ferulic and p-coumaric acid. The last one was found not only in esterified form but also in the free form. Only one flavone-apigenin glycoside was detected. Procyanidins were identified as catechin derivatives, both dimers and trimers.

  18. Instability of, and generation of hydrogen peroxide by, phenolic compounds in cell culture media.

    PubMed

    Long, Lee Hua; Hoi, Aina; Halliwell, Barry

    2010-09-01

    Many papers in the literature have described complex effects of flavonoids and other polyphenols on cells in culture. In this paper we show that hydroxytyrosol, delphinidin chloride and rosmarinic acid are unstable in three commonly-used cell culture media (Dulbecco's modified Eagle's medium (DMEM), RPMI 1640 (RPMI) and Minimal Essential Medium Eagle (MEM)) and undergo rapid oxidation to generate H2O2. This may have confounded some previous studies on the cellular effects of these compounds. By contrast, apigenin, curcumin, hesperetin, naringenin, resveratrol and tyrosol did not generate significant H2O2 levels in these media. Nevertheless, curcumin and, to a lesser extent, resveratrol (but not tyrosol) were also unstable in DMEM, so the absence of detectable H2O2 production by a compound in cell culture media should not be equated to stability of that compound. Compound instability and generation of H2O2 must be taken into account in interpreting effects of phenolic compounds on cells in culture.

  19. 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.

  20. Olive oil phenolic compounds inhibit homocysteine-induced endothelial cell adhesion regardless of their different antioxidant activity.

    PubMed

    Manna, Caterina; Napoli, Daniela; Cacciapuoti, Giovanna; Porcelli, Marina; Zappia, Vincenzo

    2009-05-13

    In this study, we examine the effect of extra virgin olive oil phenolic compounds on homocysteine-induced endothelial dysfunction and whether the protective effects are related to their different scavenging activities. Structurally related compounds have been assayed for their ability to reduce homocysteine-induced monocyte adhesion as well as the cell surface expression of intercellular adhesion molecule-1 (ICAM-1) in EA.hy.926 cells. As well-known, among the selected phenolic compounds, hydroxytyrosol, homovanillyl alcohol, and the hydroxycinnamic acid derivatives caffeic and ferulic acid display high scavenging activities, while tyrosol and p-coumaric acid are poorly active. All of the tested compounds, approaching potential in vivo concentrations, significantly reduce homocysteine-induced cell adhesion and ICAM-1 expression. Interestingly, we report the first evidence that monophenols tyrosol and p-coumaric acid are selectively protective only in homocysteine-activated cells, while they are ineffective in reducing ICAM-1 expression induced by TNFalpha. Finally, we report the synergistic effect of o-diphenolic and monophenolic compounds.

  1. Phenol compounds in solutions of soils of different types in the central forest state biosphere reserve

    NASA Astrophysics Data System (ADS)

    Malinina, M. S.; Ivanilova, S. V.

    2008-04-01

    The interannual, seasonal, and daily dynamics of the contents of phenol compounds in the soil solution of a peat-podzolic-gleyic soil in the southern taiga are considered. The concentrations of phenol compounds in the studied soil remain relatively stable. In the solutions obtained from different soil types, the main limiting factor is the degree of hydromorphism, which manifests itself via the biological factor—the intensity of the microorganisms activity and the composition and quality of the forest litters.

  2. Fractionation of Phenolic Compounds Extracted from Propolis and Their Activity in the Yeast Saccharomyces cerevisiae

    PubMed Central

    Petelinc, Tanja; Polak, Tomaž; Demšar, Lea; Jamnik, Polona

    2013-01-01

    We have here investigated the activities of Slovenian propolis extracts in the yeast Saccharomyces cerevisiae, and identified the phenolic compounds that appear to contribute to these activities. We correlated changes in intracellular oxidation and cellular metabolic energy in these yeasts with the individual fractions of the propolis extracts obtained following solid-phase extraction. The most effective fraction was further investigated according to its phenolic compounds. PMID:23409133

  3. 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.

  4. 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,...

  5. 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,...

  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, 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,...

  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. 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.

  10. 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.

  11. Stability of Virgin Olive Oil Phenolic Compounds during Long-Term Storage (18 Months) at Temperatures of 5-50 °C.

    PubMed

    Krichene, Dhouha; Salvador, María Desamparados; Fregapane, Giuseppe

    2015-08-05

    Virgin olive oil (VOO) phenolic compounds have high nutritional and biological properties. The purpose of this research was to study the stability of VOO phenolic compounds during long-term storage (18 months) at different temperatures (5, 15, 25, and 50 °C) and to verify the advantage of storing VOO at a temperature lower than the usual commercial conditions (20-25 °C). Four monovarietal VOOs that differed in their fatty acid profile and content of natural antioxidants were used in this study. The degradation of secoiridoid phenolics during storage displayed pseudo-first-order kinetics and depended on the initial content of phenolics related to olive oil variety. The initial degradation rate was similar at 5 and 15 °C but increased considerably at 25 °C and was even faster at 50 °C. Tyrosol derivatives were more stable than hydroxytyrosol compounds, especially in closed bottles with limited oxygen availability. The increase in the content of simple phenolics, the decrease of their secoiridoid derivatives, or the ratio of simple to secoiridoid phenolics could be used as indices of the oxidative and hydrolytic degradation of VOO phenolics. The shelf life of the studied VOO was considerably extended at reduced storage temperature (15 vs 25 °C). Moreover, storage conditions affected VOO phenolic content and therefore the expiration date of the health claim that olive oil polyphenols contribute to the protection of blood lipids from oxidative stress.

  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 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

  14. 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.

  15. Dynamics of phenolic acids and lignin accumulation in metal-treated Matricaria chamomilla roots.

    PubMed

    Kovácik, Jozef; Klejdus, Borivoj

    2008-03-01

    Phenylalanine ammonia-lyase (PAL) activity, 11 phenolic acids and lignin accumulation in Matricaria chamomilla roots exposed to low (3 microM) and high (60 and 120 microM) levels of cadmium (Cd) or copper (Cu) for 7 days were investigated. Five derivatives of cinnamic acid (chlorogenic, p-coumaric, caffeic, ferulic and sinapic acids) and six derivatives of benzoic acid (protocatechuic, vanillic, syringic, p-hydroxybenzoic, salicylic acids and protocatechuic aldehyde) were detected. Accumulation of glycoside-bound phenolics (revealed by acid hydrolysis) was enhanced mainly towards the end of the experiment, being more expressive in Cu-treated roots. Interestingly, chlorogenic acid was extremely elevated by the highest Cu dose (21-fold higher than control) suggesting its involvement in antioxidative protection. All compounds, with the exception of chlorogenic acid, were detected in the cell wall bound fraction, but only benzoic acids were found in the ester-bound fraction (revealed by alkaline hydrolysis). Soluble phenolics were present in substantially higher amounts in Cu-treated roots and more Cu was retained there in comparison to Cd. Cu strongly elevated PAL activity (by 5.4- and 12.1-fold in 60 and 120 microM treatment, respectively) and lignin content (by 71 and 148%, respectively) after one day of treatment, indicating formation of a barrier against metal entrance. Cd had slighter effects, supporting its non-redox active properties. Taken together, different forms of phenolic metabolites play an important role in chamomile tolerance to metal excess and participate in active antioxidative protection.

  16. Oxidation of phenols by horseradish peroxidase and lactoperoxidase compound II--kinetic considerations.

    PubMed

    Zahida, M S; Deva, W; Peerzada, G M; Behere, D V

    1998-12-01

    Oxidation of para substituted phenols by horseradish peroxidase compound II (HRP-II) and lactoperoxidase compound II (LPO-II) were studied using stopped flow technique. Apparent second order rate constants (kapp) of the reactions were determined. The kinetics of oxidation of phenols by HRP-II and LPO-II have been compared with the oxidation potentials of the substrates. Reorganization energies of electron-transfer of phenols to the enzymes were estimated from the variation of second order rate constants with the thermodynamic driving force.

  17. 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.

  18. 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.

  19. 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.

  20. 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

  1. 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.

  2. Beaver (Castor canadensis) responses to major phenolic and neutral compounds in castoreum.

    PubMed

    Schulte, B A; Müller-Schwarze, D; Tang, R; Webster, F X

    1994-12-01

    North American beaver (Castor canadensis) mark their territories with castoreum, a chemically complex secretion from their castor sacs. The phenolic and neutral fractions of castoreum have been shown to elicit specific behavioral responses from beavers in a field setting. Our objective was to identify compounds/mixtures that evoked responses similar to those stimulated by castoreum. We assayed recently identified phenolic compounds, some phenolics that had been determined to be biologically active in previous studies, the neutral compound borneol, and combinations of phenolic compounds, neutral compounds, and the two combined. Biological activity was measured by the elicitation and extent of specific responses and their strength (duration, frequency, and proportion of beavers responding). Generally, single compounds stimulated fewer responses than mixtures. A 26-compound mixture of phenolic and neutral compounds elicited responses in a similar proportion of trials as castoreum. However, responses to castoreum were stronger than to any synthetic sample. Further investigation of different measures of response, namely, elicitation, completeness, and strength, are deemed necessary to fully decipher the design of social odors.

  3. Dietary Phenolic Compounds Interfere with the Fate of Hydrogen Peroxide in Human Adipose Tissue but Do Not Directly Inhibit Primary Amine Oxidase Activity.

    PubMed

    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 [(14)C]-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.

  4. 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

  5. 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+).

  6. 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.

  7. Methodologies for the extraction of phenolic compounds from environmental samples: new approaches.

    PubMed

    Mahugo Santana, Cristina; Sosa Ferrera, Zoraida; Esther Torres Padrón, M; Juan Santana Rodríguez, José

    2009-01-09

    Phenolic derivatives are among the most important contaminants present in the environment. These compounds are used in several industrial processes to manufacture chemicals such as pesticides, explosives, drugs and dyes. They also are used in the bleaching process of paper manufacturing. Apart from these sources, phenolic compounds have substantial applications in agriculture as herbicides, insecticides and fungicides. However, phenolic compounds are not only generated by human activity, but they are also formed naturally, e.g., during the decomposition of leaves or wood. As a result of these applications, they are found in soils and sediments and this often leads to wastewater and ground water contamination. Owing to their high toxicity and persistence in the environment, both, the US Environmental Protection Agency (EPA) and the European Union have included some of them in their lists of priority pollutants. Current standard methods of phenolic compounds analysis in water samples are based on liquid-liquid extraction (LLE) while Soxhlet extraction is the most used technique for isolating phenols from solid matrices. However, these techniques require extensive cleanup procedures that are time-intensive and involve expensive and hazardous organic solvents, which are undesirable for health and disposal reasons. In the last years, the use of news methodologies such as solid-phase extraction (SPE) and solid-phase microextraction (SPME) have increased for the extraction of phenolic compounds from liquid samples. In the case of solid samples, microwave assisted extraction (MAE) is demonstrated to be an efficient technique for the extraction of these compounds. In this work we review the developed methods in the extraction and determination of phenolic derivatives in different types of environmental matrices such as water, sediments and soils. Moreover, we present the new approach in the use of micellar media coupled with SPME process for the extraction of phenolic

  8. Application of microchip-CE electrophoresis to follow the degradation of phenolic acids by aquatic plants.

    PubMed

    Ding, Yongsheng; Garcia, Carlos D

    2006-12-01

    In this paper, we describe the separation and detection of six phenolic acids using an electrophoretic microchip with pulsed amperometric detection (PAD). The selected phenolic acids are particularly important because of their biological activity. The analysis of these compounds is typically performed by chromatography or standard CE coupled with a wide variety of detection modes. However, these methods are slow, labor intensive, involve a multistep solvent extraction, require skilled personnel, or use bulky and expensive instrumentation. In contrast, microchip CE offers the possibility of performing simpler, less expensive, and faster analysis. In addition, integrated devices can be custom-fabricated and incorporated with portable computers to perform on-site analysis. In the present report, the effect of the separation potential, buffer pH and composition, injection time and PAD parameters were studied in an effort to optimize both the separation and detection of these phenolic acids. Using the optimized conditions, the analysis can be performed in less than 3 min, with detection limits ranging from 0.73 microM (0.10 microg/mL) for 4-hydroxyphenylacetic acid to 2.12 microM (0.29 microg/mL) for salicylic acid. In order to demonstrate the capabilities of the device, the degradation of a mixture of these acids by two aquatic plants was followed using the optimized conditions.

  9. Salicylic acid-induced changes to growth and phenolic metabolism in Matricaria chamomilla plants.

    PubMed

    Kovácik, Jozef; Grúz, Jirí; Backor, Martin; Strnad, Miroslav; Repcák, Miroslav

    2009-01-01

    The influence of salicylic acid (SA) doses of 50 and 250 microM, for a period of up to 7 days, on selected physiological aspects and the phenolic metabolism of Matricaria chamomilla plants was studied. SA exhibited both growth-promoting (50 microM) and growth-inhibiting (250 microM) properties, the latter being correlated with decrease of chlorophylls, water content and soluble proteins. In terms of phenolic metabolism, it seems that the higher SA dose has a toxic effect, based on the sharp increase in phenylalanine ammonia-lyase (PAL) activity (24 h after application), which is followed by an increase in total soluble phenolics, lignin accumulation and the majority of the 11 detected phenolic acids. Guaiacol-peroxidase activity was elevated throughout the experiment in 250 microM SA-treated plants. In turn, some responses can be explained by mechanisms associated with oxidative stress tolerance; these mitigate acute SA stress (which is indicated by an increase in malondialdehyde content). However, PAL activity decreased with prolonged exposure to SA, indicating its inhibition. Accumulation of coumarin-related compounds (umbelliferone and herniarin) was not affected by SA treatments, while (Z)- and (E)-2-beta-D: -glucopyranosyloxy-4-methoxycinnamic acids increased in the 250 microM SA-treated rosettes. Free SA content in the rosettes increased significantly only in the 250 microM SA treatment, with levels tending to decrease towards the end of the experiment and the opposite trend was observed in the roots.

  10. Anti-HSV-1, antioxidant and antifouling phenolic compounds from the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502.

    PubMed

    Huang, Zhonghui; Nong, Xuhua; Ren, Zhe; Wang, Jie; Zhang, Xiaoyong; Qi, Shuhua

    2017-02-15

    Chemical investigation of the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502 resulted in the isolation of three new anthraquinones, aspergilols G-I (1-3), one new diphenyl ether, 4-carbglyceryl-3,3'-dihydroxy-5,5'-dimethyldiphenyl ether (4), and one new benzaldehyde derivative, 2,4-dihydroxy-6-(4-methoxy-2-oxopentyl)-3-methylbenzaldehyde (5), along with 23 known phenolic compounds (6-28). The structures of new compounds were elucidated by extensive spectroscopic analysis. The absolute configuration of 3 was established by CD spectrum and the modified Mosher method. Compounds 2, 3 and 9 had evident antiviral activity towards HSV-1 with EC50 values of 4.68, 6.25, and 3.12μM, respectively. Compounds 15, 18, 20 and 22-24 showed more potent antioxidant activity than l-ascorbic acid with IC50 values of 18.92-52.27μM towards DPPH radicals. Comparison of the structures and antioxidant activities of 1-28 suggests that the number of phenolic hydroxyl group that can freely rotate can significantly affect the antioxidant activity of phenolic compounds. In addition, 4, 22-24 and 27 had significant antifouling activity against Bugula neritina larval settlement with EC50 values of 1.28, 2.61, 5.48, 1.59, and 3.40μg/ml, respectively.

  11. Determination of phenolic compounds derived from hydrolysable tannins in biological matrices by RP-HPLC.

    PubMed

    Díez, María Teresa; García del Moral, Pilar; Resines, José Antonio; Arín, María Jesús

    2008-08-01

    An RP-HPLC method for the determination of four phenolic compounds: gallic acid (GA), pyrogallol (PY), resorcinol (RE) and ellagic acid (EA), derived from hydrolysable tannins is reported. Separation was achieved on a SunFire C18 (250 x 4.6 mm id, 5 microm) column at 40 degrees C with gradient elution. UV detection at 280 nm was applied. The developed method was validated in terms of linearity, accuracy and precision. Satisfactory repeatability and between day precision were noticed with RSD values lower than 3%. Recoveries from different biological samples ranged from 91.50 to 105.25%. The LODs were estimated as 1.70 mg/L for PY, 1.68 mg/L for GA, 1.52 mg/L for RE and 0.98 mg/L for EA with a 20 microL injection volume. The method was applied for the determination of these compounds in oak leaves and in ruminal fluid and urine samples taken from beef cattle fed with oak leaves. The proposed method could be used in ruminant nutrition studies to verify the effect that a diet rich in tannins have on ruminal fermentation and to determine the toxicity of these compounds.

  12. Phenolic compounds in olive oil: antioxidant, health and organoleptic activities according to their chemical structure.

    PubMed

    Servili, M; Esposto, S; Fabiani, R; Urbani, S; Taticchi, A; Mariucci, F; Selvaggini, R; Montedoro, G F

    2009-04-01

    Hydrophilic phenols are the most abundant natural antioxidants of virgin olive oil (VOO), in which, however, tocopherols and carotenes are also present. The prevalent classes of hydrophilic phenols found in VOO are phenolic alcohols and acids, flavonoids, lignans and secoiridoids. Among these substances the last two classes include the most concentrate phenols of VOO. Secoiridoids, like aglycone derivatives of oleuropein, demethyloleuropein and ligstroside, are present in olive fruit as most abundant VOO phenolic antioxidants. Several important biological properties (antioxidant, anti-inflammatory, chemopreventive and anti-cancer) and the characteristic pungent and bitter tasty properties have been attributed to VOO phenols. Relationships between polyphenols activities and their chemical structures are discussed in this paper.

  13. Separation and characterization of phenolic compounds from U.S. pecans by liquid chromatography-tandem mass spectrometry.

    PubMed

    Robbins, Katherine S; Ma, Yuanyuan; Wells, M Lenny; Greenspan, Phillip; Pegg, Ronald B

    2014-05-14

    The phenolic acids and proanthocyanidins (PACs) of pecans possess bioactive properties, which might be useful in retarding the onset of and ameliorating the status of certain chronic disease states. There is a general lack of information in the literature regarding such compounds, especially the PACs. Crude phenolic extracts pooled from eight commercially significant cultivars were selected based on their relatively high antioxidant capacities. The pooled extracts were separated via Sephadex LH-20 column chromatography into five ethanolic low-molecular-weight (LMW) fractions and one acetonic high-molecular-weight (HMW) fraction. The preparations were then characterized using RP-HPLC-ESI-MS/MS and diol-phase HPLC-ESI-MS/MS in order to determine the key constituents present in the LMW and HMW fractions, respectively. As previously observed in pecan nutmeat, ellagic acid and (+)-catechin were found to be the major phenolics in the LMW fractions. The last eluting LMW fraction did not contain phenolic acids; rather it possessed PAC monomers and dimers. The HMW fraction comprised a majority of its PACs as dimers; yet, monomers, trimers, tetramers, pentamers, and hexamers were also separated and characterized.

  14. 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'.

  15. Fractionation of organosolv lignin from olive tree clippings and its valorization to simple phenolic compounds.

    PubMed

    Toledano, Ana; Serrano, Luis; Balu, Alina Mariana; Luque, Rafael; Pineda, Antonio; Labidi, Jalel

    2013-03-01

    Lignin valorization practices have attracted a great deal of interest in recent years due to the large excess of lignin produced by the pulp and paper industry, together with second-generation bioethanol plants. In this work, a new lignin valorization approach is proposed. It involves ultrafiltration as a fractionation process to separate different molecular weight lignin fractions followed by a hydrogen-free, mild, hydrogenolytic, heterogeneously catalyzed methodology assisted by microwave irradiation to obtain simple phenolic, monomeric products by depolymerization using a nickel-based catalyst. The main products obtained were desaspidinol, syringaldehyde, and syringol; this proves the efficiency of the depolymerization conditions applied. The concentration of these observed compounds increased when the molecular weights of the lignin fractions increased. The applied depolymerization conditions, which take advantage of the use of formic acid as a hydrogen-donating solvent, did not generate any biochar in the systems.

  16. Isolation of functional RNA from plant tissues rich in phenolic compounds.

    PubMed

    Schneiderbauer, A; Sandermann, H; Ernst, D

    1991-08-15

    A method for the isolation of RNA from different tissues of trees (seedlings, saplings, and adult trees) is described. Using this procedure it is possible to remove large amounts of disturbing polyphenolic compounds from nucleic acids. The method involves an acetone treatment of the freeze-dried and powdered plant material, the use of high salt concentrations in the extraction buffer and an aqueous two-phase system. These steps were combined with the conventional phenol/chloroform extraction and CsCl centrifugation. The method has been successfully applied to the isolation and purification of RNA from pine (Pinus sylvestris L. and Pinus mugo Turr.), Norway spruce (Picea abies L.), and beech (Fagus sylvatica L.). The functional quality of RNA extracted by this procedure has been characterized by its uv spectrum, by agarose gel electrophoresis with ethidium bromide staining, Northern blot hybridization, and in vitro translation.

  17. Simultaneous isocratic separation of phenolic acids and flavonoids using micellar liquid chromatography.

    PubMed

    Hadjmohammadi, Mohammad Reza; Nazari, S Saman S J

    2013-12-01

    The simultaneous isocratic separation of a mixture of five phenolic acids and four flavonoids (two important groups of natural polyphenolic compounds with very different polarities) was investigated in three different RPLC modes using a hydro-organic mobile phase, and mobile phases containing SDS at concentrations below and above the critical micellar concentration (submicellar LC and micellar LC (MLC), respectively). In the hydro-organic mode, methanol and acetonitrile; in the submicellar mode methanol; and in the micellar mode, methanol and 1-propanol were examined individually as organic modifiers. Regarding the other modes, MLC provided more appropriate resolutions and analysis time and was preferred for the separation of the selected compounds. Optimization of separation in MLC was performed using an interpretative approach for each alcohol. In this way, the retention of phenolic acids and flavonoids were modeled using the retention factors obtained from five different mobile phases, then the Pareto optimality method was applied to find the best compatibility between analysis time and quality of separation. The results of this study showed some promising advantages of MLC for the simultaneous separation of phenolic acids and flavonoids, including low consumption of organic solvent, good resolution, short analysis time, and no requirement of gradient elution.

  18. Identification of bioaccessible and uptaken phenolic compounds from strawberry fruits in in vitro digestion/Caco-2 absorption model.

    PubMed

    Kosińska-Cagnazzo, Agnieszka; Diering, Sascha; Prim, Denis; Andlauer, Wilfried

    2015-03-01

    Strawberry fruits are highly valued for their taste and nutritional value. However, results describing the bioaccessibility and intestinal absorption of phenolic compounds from strawberries are still scarce. In our study, a combined in vitro digestion/Caco-2 absorption model was used to mimic physiological conditions in the gastrointestinal track and identify compounds transported across intestinal epithelium. In the course of digestion, the loss of anthocyanins was noted whilst pelargonidin-3-glucoside remained the most abundant compound, amounting to nearly 12 mg per 100 g of digested strawberries. Digestion increased the amount of ellagic acid available by nearly 50%, probably due to decomposition of ellagitannins. Only trace amounts of pelargonidin-3-glucoside were found to be absorbed in the intestine model. Dihydrocoumaric acid sulphate and p-coumaric acid were identified as metabolites formed in enterocytes and released at the serosal side of the model.

  19. Effects of environment and genotype on phenolic acids in wheat in the HEALTHGRAIN diversity screen.

    PubMed

    Fernandez-Orozco, Rebeca; Li, Li; Harflett, Claudia; Shewry, Peter R; Ward, Jane L

    2010-09-08

    Phenolic acid content and composition have been determined in 26 wheat genotypes grown in Hungary over three consecutive years and at three additional locations (France, United Kingdom, and Poland) during the third year. Fractions comprising free, soluble conjugated, and bound phenolic acids were analyzed using HPLC with measurements being made for individual phenolic acids in each fraction. Statistically significant differences in phenolic acid content occurred across the different growing locations with the average total phenolic acid content being highest in the genotypes grown in Hungary. The growth year in Hungary also had a large impact, especially on the free and conjugated phenolic acid contents. Certain genotypes were more resistant to environmental impacts than others. Of the genotypes with high levels of total phenolic acids, Lynx, Riband, Tommi, and Cadenza were most stable with respect to their total contents, whereas Valoris, Herzog, and Malacca, also high in phenolic acid content, were least stable. Of the three fractions analyzed, the free and conjugated phenolic acids were most variable and were also susceptible to the effect of environment, whereas bound phenolic acids, which comprised the greatest proportion of the total phenolic acids, were the most stable.

  20. 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.

  1. 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

    2008-10-08

    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.

  2. 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.

  3. 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