Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity

Sulfate conjugation by phenolsulfotransferase (PST) enzyme is an important process in the detoxification of xenobiotics and endogenous compounds. There are two forms of PST that are specific for the sulfation of small phenols (PST-P) and monoamines (PST-M). Phenoilc acids have been reported to have important biological and pharmacological properties and may have benefits to human health. In the present study, human platelets were used as a model to investigate the influence of 13 phenolic acids on human PST activity and to evaluate the relationship to their antioxidant activity. The results showed that chlorogenic acid, syringic acid, protocatechuic acid, vanillic acid, sinapic acid, and caffeic acid significantly (p < 0.05) inhibited the activities of both forms of PST by 21-30% at a concentration of 6.7 microM. The activity of PST-P was enhanced (p < 0.05) by p-hydroxybenzoic acid, gallic acid, gentisic acid, o-coumaric acid, p-coumaric acid, and m-coumaric acid at a concentration of 6.7 microM, whereas the activity of PST-M was enhanced by gentisic acid, gallic acid, p-hydroxybenzoic acid, and ferulic acid. The phenolic acids exhibited antioxidant activity as determined by the oxygen radical absorbance capacity (ORAC) assay and Trolox equivalent antioxidant capacity (TEAC) assay, especially gallic acid, p-hydroxybenzoic acid, gentisic acid, and coumaric acid, which had strong activity. The overall effect of phenolic acids tested on the activity of PST-P and PST-M was well correlated to their antioxidant activity of ORAC value (r = 0.71, p < 0.01; and r = 0.66, p < 0.01). These observations suggest that antioxidant phenolic acids might alter sulfate conjugation.     

Comparison of antioxidant activity, anthocyanins, carotenoids, and phenolics of three native fresh and sun-dried date (Phoenix dactylifera L.) varieties grown in Oman

Fresh and sun-dried dates of three native varieties from Oman, namely, Fard, Khasab, and Khalas, were examined for their antioxidant activity and total contents of anthocyanins, carotenoids, and phenolics, as well as free and bound phenolic acids. All results are expressed as mean value +/- standard deviation (n = 3) on a fresh weight basis. Fresh date varieties were found to be a good source of antioxidants (11687-20604 micromol of Trolox equiv/g), total contents of anthocyanins (0.24-1.52 mg of cyanidin 3-glucoside equiv/100 g), carotenoids (1.31-3.03 mg/100 g), phenolics (134-280 mg of ferulic acid equiv/100 g), free phenolic acids (2.61-12.27 mg/100 g), and bound phenolic acids (6.84-30.25 mg/100 g). A significant (p < 0.05) amount of antioxidants and carotenoids was lost after sun-drying of dates, whereas the total content of phenolics and free and bound phenolic acids increased significantly (p < 0.05). Anthocyanins were detected only in fresh dates. Date varieties had different levels and patterns of phenolic acids. Four free phenolic acids (protocatechuic acid, vanillic acid, syringic acid, and ferulic acid) and nine bound phenolic acids (gallic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, syringic acid, p-coumaric acid, ferulic acid, and o-coumaric acid) were tentatively identified. Of the date varieties studied, Khalas, which is considered to be premium quality, had higher antioxidant activity, total carotenoids, and bound phenolic acids than other varieties. These results suggest that all date varieties serve as a good source of natural antioxidants and could potentially be considered as a functional food or functional food ingredient, although some of their antioxidant constituents are lost during sun-drying.     

Exudation of allelopathic substances in buckwheat (Fagopyrum esculentum Moench)

Root exudates of the common buckwheat, especially phenolic compounds, were studied. Their contents, both in the soil during the growing season and in agar medium during germination, were determined by HPLC and GC-MS. The allelopathic activity of the soil from a buckwheat stand was evaluated, as well. Palmitic acid, squalene, epicatechin, vitexin, a gallic acid derivative, and a quercetin derivative were the main compounds of the agar medium. In the soil, palmitic acid methyl ester, vanillic acid, rutin, a gallic acid derivative, and a 4-hydroxyacetophenone derivative were identified. The effects of vitexin, squalene, epicatechin, 4-hydroxyacetophenone, and vanillic and gallic acids were tested on eight plant species. Inhibitive effects were observed in the cases of 4-hydroxyacetophenone and vanillic and gallic acids. Comparisons of the identified compounds and inhibitive effects of soil extracts indicated that palmitic acid and the gallic acid derivative probably have an important function in the allelopathic root response of buckwheat.     

Bending affects phenolic content of William pear leaves

Abstract

The effect of branch bending on the phenolic content in pear leaves was investigated. Leaves were sampled from the tree branches which were bent in summer 2003 (1 September), in spring 2004 (15 May), and from unbent trees. Samplings were made during the growing season May to October 2004, on the following dates: 1st sampling, 15 May; 2nd sampling, 11 June; 3rd sampling, 9 July; 4th sampling, 6 August; 5th sampling, 2 September; and 6th sampling, 1 October. The leaves contained caffeic acid, chlorogenic acid, sinapic acid, syringic acid, vanillic acid, rutin, epicatechin and catechin. The lowest contents of phenolics were found on the first occasion. After that, in the sequence of sampling dates, an increase was noticed at first, but after reaching their highest point, the contents of phenolics decreased. In most cases fewer contents of phenolic compounds were found in leaves from bent branches (especially from branches bent in summer), and the highest ones in leaves from the control group. For all phenolics, apart from the caffeic and vanillic acids, significant differences were evident among treatments, with the highest contents in the control group and almost the lowest in the summer treatment. It is suggested that the change in branch angle caused the physiological response of pear tree, with different contents of phenolic compounds in its leaves from bent and non-bent branches.     

Phenolic composition of kiwifruit juice

Phenolic compounds in kiwifruit pulp were separated and characterized by reversed-phase HPLC, and the effect of juice processing on the phenolic composition was studied. Fractionation of phenolic compounds was achieved through selective elution from C-18 cartridges prior to preconcentration and subsequent separation by HPLC. Strongly acidic compounds were identified as derivatives of coumaric and caffeic acids, including chlorogenic acid, protocatechuic acid, and a derivative of 3,4-dihydroxybenzoic acid. The weakly acidic fraction contained epicatechin, catechin, and procyanidins (B3, B2, or B4 and oligomers). Flavonols were present as the glycosides of quercetin (glucoside, rhamnoside, and rutinoside) and kaempferol (rhamnoside and rutinoside). Phenolic compounds were present, at levels of <1-7 mg/L, in clarified juice. The concentration of phenolics was highest after high-temperature short-time treatment (HTST) of juice. Hydrolysis of hydroxycinnamic acids occurred after enzyme addition and HTST treatment. The flavonol glycoside composition is the best identifier of kiwifruit juice.     

Major flavonoids in grape seeds and skins: antioxidant capacity of catechin, epicatechin, and gallic acid

Grape seeds and skins are good sources of phytochemicals such as gallic acid, catechin, and epicatechin and are suitable raw materials for the production of antioxidative dietary supplements. The differences in levels of the major monomeric flavanols and phenolic acids in seeds and skins from grapes of Vitis vinifera varieties Merlot and Chardonnay and in seeds from grapes of Vitis rotundifolia variety Muscadine were determined, and the antioxidant activities of these components were assessed. The contribution of the major monomeric flavonols and phenolic acid to the total antioxidant capacity of grape seeds and skins was also determined. Gallic acid, monomeric catechin, and epicatechin concentrations were 99, 12, and 96 mg/100 g of dry matter (dm) in Muscadine seeds, 15, 358, and 421 mg/100 g of dm in Chardonnay seeds, and 10, 127, and 115 mg/100 g of dm in Merlot seeds, respectively. Concentrations of these three compounds were lower in winery byproduct grape skins than in seeds. These three major phenolic constituents of grape seeds contributed <26% to the antioxidant capacity measured as ORAC on the basis of the corrected concentrations of gallic acid, catechin, and epicatechin in grape byproducts. Peroxyl radical scavenging activities of phenolics present in grape seeds or skins in decreasing order were resveratrol > catechin > epicatechin = gallocatechin > gallic acid = ellagic acid. The results indicated that dimeric, trimeric, oligomeric, or polymeric procyanidins account for most of the superior antioxidant capacity of grape seeds.     

Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Acai (Euterpe oleracea Mart.)

Phenolic compounds present in crude oil extracts from acai fruit ( Euterpe oleracea) were identified for the first time. The stability of acai oil that contained three concentrations of phenolics was evaluated under short- and long-term storage for lipid oxidation and phenolic retention impacting antioxidant capacity. Similar to acai fruit itself, acai oil isolates contained phenolic acids such as vanillic acid (1,616 +/- 94 mg/kg), syringic acid (1,073 +/- 62 mg/kg), p-hydroxybenzoic acid (892 +/- 52 mg/kg), protocatechuic acid (630 +/- 36 mg/kg), and ferulic acid (101 +/- 5.9 mg/kg) at highly enriched concentrations in relation to acai pulp as well as (+)-catechin (66.7 +/- 4.8 mg/kg) and numerous procyanidin oligomers (3,102 +/- 130 mg/kg). Phenolic acids experienced up to 16% loss after 10 weeks of storage at 20 or 30 degrees C and up to 33% loss at 40 degrees C. Procyanidin oligomers degraded more extensively (23% at 20 degrees C, 39% at 30 degrees C, and 74% at 40 degrees C), in both high- and low-phenolic acai oils. The hydrophilic antioxidant capacity of acai oil isolates with the highest phenolic concentration was 21.5 +/- 1.7 micromol Trolox equivalents/g, and the total soluble phenolic content was 1252 +/- 11 mg gallic acid equivalents/kg, and each decreased by up to 30 and 40%, respectively, during long-term storage. The short-term heating stability at 150 and 170 degrees C for up to 20 min exhibited only minor losses (<10%) in phenolics and antioxidant capacity. Because of its high phenolic content, the phytochemical-enriched acai oil from acai fruit offers a promising alternative to traditional tropical oils for food, supplements, and cosmetic applications.     

Free radical scavenging properties and phenolic content of Chinese black-grained wheat

Free radical scavenging properties and phenolic content of extracts from a novel Chinese black-grained wheat were evaluated for comparison with selected wheat controls. Extracts of bran and whole meal were compared for their scavenging activities against the 2,2-diphenyl-1-picryhydrazyl (DPPH) free radical. The total phenolic content and phenolic acid levels were determined using colorimetric and high-performance liquid chromatography (HPLC) methods, respectively. There were significant differences in radical scavenging activities and phenolic contents among bran or whole meal samples of Chinese black-grained wheat and selected wheat controls. Chinese black-grained wheat had the strongest scavenging activity and the highest total phenolic content among the wheat samples. The scavenging activity and total phenolic content of wheat bran was generally twice as high as that of whole meal. A positive correlation was found between DPPH radical scavenging activity and total phenolic content of bran (R = 0.86) and whole meal (R = 0.96). In addition, HPLC analysis detected the presence of gallic, p-hydroxybenzoic, caffeic, syringic, p-coumaric, vanillic, gentisic, o-coumaric acid, and ferulic acids in wheat bran. Ferulic acid content was highest among the phenolic acids. Chinese black-grained wheat may be considered as a potential source of natural antioxidants given its high free radical scavenging ability and phenolic content. Additional research is needed to further investigate other phenolic compounds and evaluate their contribution to the antioxidant activity in order to understand the nutraceutical value of the novel black-grained wheat genotype.     

Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection

A high-performance liquid chromatographic (HPLC) method with diode-array detection (DAD) was used to identify and quantify free and total phenolic acids (m-hydroxybenzoic acid, p-hydroxybenzoic acid, protocatechuic acid, gallic acid, vanillic acid, syringic acid, o-coumaric acid, m-coumaric acid, p-coumaric acid, caffeic acid, ferulic acid, sinapic acid, chlorogenic acid, and ellagic acid) in plant foods. Free phenolic acids were extracted with a mixture of methanol and 10% acetic acid. Bound phenolic acids were liberated using first alkaline and then acid hydrolysis followed by extraction with diethyl ether/ethyl acetate (1:1). All fractions were quantified separately by HPLC. After HPLC quantification, results of alkali and acid hydrolysates were calculated to represent total phenolic acids. Ellagic acid was quantified separately after long (20 h) acid hydrolysis. The methods developed were effective for the determination of phenolic acids in plant foods. DAD response was linear for all phenolic acids within the ranges evaluated, with correlation coefficients exceeding 0.999. Coefficients of variation for 4-8 sample replicates were consistently below 10%. Recovery tests of phenolic acids were performed for every hydrolysis condition using several samples. Recoveries were generally good (mean >90%) with the exceptions of gallic acid and, in some cases, caffeic acid samples.     

Behavior of phenolic substances in the decaying process of plants: I. Identification and Quantitative Determination of Phenolic Acids in Rice Straw and Its Decayed Product by Gas Chromatography

Phenolic acids in rice straw and its decayed product were surveyed and quantitatively analyzed by gas chromatography.

1) Thirteen kinds of phenolic acids in rice straw and its decayed product were identified. Besides p-hydroxybenzoic, vanillic, P-coumaric, and ferulic acids which had been already reported, nine phenolic acids were newly identified; these were benzoic, salicylic, syringic, protocatechuic, β-resorcylic, caffeic, sinapic, gallic, and gentisic acids.

2) A gas chromatographic analysis was applied to the micro-determination of major phenolic acids in rice straw and . the decayed products. The methanolic alkaline extracts from them were washed with ether, acidified, transferred into ether, trimethylsilylated, and injected into a gas chromatograph equipped with a silicon SE-30 column. The recoveries of p-coumaric, p-hydroxybenzoic, vanillic, and syringic acids were more than 90%, and ferulic and syringic acids were recovered at about 70%.

3) The content of each of the above described major phenolic acids in rice straw ranged from 0.002 to 0.037% per dry weight. p-Coumaric acid was contained in the largest amount. Ferulic and vanillic acids followed. In the decayed straw, these contents decreased to 0.002–0.017%. The whole phenolic substances in ether-extracted fraction were present at 0.34%, and the amount decreased to one-third during the decaying process.     

Interaction of the Mixture of Phenolic Acids with Modified Kaolinite under Batch and Dynamic Conditions

Phenolic acids play an important role in the formation of soil profiles, however their cooperative sorption by mineral phases under environmentally relevant concentrations is poorly studied. In the present work the sorption of an equimolar mixture of phenolic acids by kaolinite modified with amorphous aluminum hydroxide has been studied under both batch and continuous-flow conditions. It has been found that the sorption of gallic and protocatechuic acids containing OH groups in the ortho position exceeds the sorption of p-hydroxybenzoic and methoxylated acids (vanillic, syringic, and ferulic) by an order of magnitude. The study of sorption under dynamic (continuous-flow) conditions has shown the competition of acids for binding sites, while the active centers of kaolinite-Al(OH)_x are being occupied. The sorbed gallic acid displaces the other acids, which pass into solution in the following order: p-hydroxybenzoic acid > vanillic acid > syringic acid ? ferulic acid > protocatechuic acid. The revealed regularities indicate potentially important role of ortho-substituted hydroxybenzoic acids in the formation of soil organic matter, while p-hydroxybenzoic, vanillic, and syringic acids can be more important for the composition of soil solutions and natural waters.     

Phenolic content and antioxidant capacity of muscadine grapes

Fruits of 10 cultivars of muscadine grapes (five bronze skin and five purple skin) grown in southern Georgia were separated into skin, seed, and pulp. Each fruit part and the leaves from the corresponding varieties were extracted for HPLC analysis of major phenolics. Total phenolics were determined colorimetrically using Folin-Ciocalteu reagent. Total anthocyanins were determined according to a pH-differential method, using a UV-visible spectrophotometer. Antioxidant capacity was determined by the Trolox equivalent antioxidant capacity (TEAC) assay. Gallic acid, (+)-catechin, and epicatechin were the major phenolics in seeds, with average values of 6.9, 558.4, and 1299.4 mg/100 g of fresh weight (FW), respectively. In the skins, ellagic acid, myricetin, quercetin, kaempferol, and trans-resveratrol were the major phenolics, with respective average values of 16.5, 8.4, 1.8, 0.6, and 0.1 mg/100 g of FW. Contrary to previous results, ellagic acid and not resveratrol was the major phenolic in muscadine grapes. The HPLC solvent system used coupled with fluorescence detection allowed separation of ellagic acid from resveratrol and detection of resveratrol. Reported here for the first time are the phenolic content and antioxidant capacity of muscadine leaves. Major phenolics in muscadine leaves were myricetin, ellagic acid, kaempferol, quercetin, and gallic acid, with average concentrations of 157.6, 66.7, 8.9, 9.8, and 8.6, respectively. Average total phenolics were 2178.8, 374.6, 23.8, and 351.6 mg/g gallic acid equivalent in seed, skin, pulp, and leaves, respectively. Total anthocyanin contents were 2.1 and 132.1 mg/100 g of FW in the skins of bronze and purple grapes, respectively, and 4.3 and 4.6 mg/100 g of FW in seeds and pulps, in that order. Antioxidant capacity values were, on average, 2.4, 12.8, 281.3, and 236.1 microM TEAC/g of FW for pulps, skins, seeds, and leaves, respectively.     

Antioxidant Potentials and Phenolic Composition of Tef Varieties: An Indigenous Ethiopian Cereal

Tef, Eragrostis tef (Zucc.) Trotter, is a cereal crop originated and diversified in Ethiopia, where it is used to produce a range of food products. This study aimed to profile and quantify the phenolic composition and antioxidant potential of seven tef grain varieties. Soluble and bound phenolics ranged from 37 to 71 and from 226 to 376 mg of gallic acid equivalent/100 g dry basis (db), and soluble and bound flavonoid contents varied between 36 and 64 and between 113 and 258 mg of catechin equivalent/100 g db, respectively. Protocatechuic, vanillic, syringic, p‐coumaric, sinapic, ferulic, and rosmarinic acids, catechin, and naringenin were detected at least in three of the varieties studied. The dominant phenolic compounds were catechin, rosmarinic acid, and ferulic acid in the soluble extracts, whereas ferulic, rosmarinic, and p‐coumaric acids were the dominant ones in the bound extract. Gallic, caffeic, and salicylic acids were not detected in any of the varieties studied. The majority (>84%) of tef grain phenolics were found in bound form, contributing >84% of total 2,2‐diphenyl‐1‐picrylhydrazyl antioxidative capacity and >80% of total ferric reducing antioxidant power. These results clearly demonstrated the differences in phenolic profile among tef grain varieties. These results are relevant for developing healthy and nutritious tef‐based food products.     

LDL isolated from plasma-loaded red wine procyanidins resist lipid oxidation and tocopherol depletion

Dietary phenolic compounds may act as antioxidants in vitro, but because of structural modifications during absorption, its role based on concentrations high enough to afford an antioxidant protection needs to be re-evaluated. We have explored the hypothesis that red wine procyanidins interact with low density lipoproteins (LDL) and that, at this location, the phenolic compounds efficiently protect LDL from oxidation and maintain LDL alpha-tocopherol at a high steady state concentration by recycling it back from the alpha-tocopheroxyl radical. To this end, human plasma was supplemented with wine procyanidins and isolated LDL were challenged with a constant flux of peroxyl radicals. As compared with LDL from plasma-free procyanidins, those LDL better resisted lipid oxidation and exhibited longer lag-phases of alpha-tocopherol consumption. The procyanidins, depending on their structure, were able to reduce the UV-induced alpha-tocopherol radical in a micellar system, as evidenced by electron paramagnetic ressonance. Mechanistically, the protection of LDL was interpreted in terms of quenching of peroxyl radicals and the recycling of alpha-tocopherol by the procyanidins bound to the lipoproteins. These results support the notion that, in human plasma, the procyanidins, via binding to LDL, may act as efficient local antioxidants.     

Antioxidant properties of Fusarium head blight-resistant and -susceptible soft red winter wheat grains grown in Virginia

Fusarium head blight (FHB) has emerged as a major threat to wheat crops around the world, and it has been hypothesized that wheat antioxidants may play a role against Fusarium infections. The current study aimed to determine antioxidant properties of FHB-resistant wheat grains as compared to susceptible wheat. The wheat samples were collected from a single growing location (Warsaw, VA) and the same growing season. The results showed that both FHB-resistant and -susceptible wheat grains exerted strong radical scavenging activities against DPPH* radical [0.91-1.53 micromol of Trolox equivalents (TE)/g], peroxyl radical (15.5-24.5 micromol of TE/g), and hydroxyl radical (15.7-35.8 micromol of TE/g). Their total phenolic contents ranged from 888 to 1117 microg of gallic acid equivalents (GAE)/g. Five phenolic acids including ferulic, syringic, vanillic, caffeic, and p-coumaric acids were determined in soluble and insoluble fractions of wheat grains, altogether with a range of 219-389 microg/g. On average, the FHB-resistant wheat group showed significantly higher average values in DPPH* and hydroxyl radicals scavenging activities (30 and 41% higher, respectively) than the FHB-susceptible wheat group.     

Maple syrup phytochemicals include lignans, coumarins, a stilbene, and other previously unreported antioxidant phenolic compounds

Twenty-three phenolic compounds were isolated from a butanol extract of Canadian maple syrup (MS-BuOH) using chromatographic methods. The compounds were identified from their nuclear magnetic resonance and mass spectral data as 7 lignans [lyoniresinol (1), secoisolariciresinol (2), dehydroconiferyl alcohol (3), 5'-methoxy-dehydroconiferyl alcohol (4), erythro-guaiacylglycerol-β-O-4'-coniferyl alcohol (5), erythro-guaiacylglycerol-β-O-4'-dihydroconiferyl alcohol (6), and [3-[4-[(6-deoxy-α-l-mannopyranosyl)oxy]-3-methoxyphenyl]methyl]-5-(3,4-dimethoxyphenyl)dihydro-3-hydroxy-4-(hydroxymethyl)-2(3H)-furanone (7)], 2 coumarins [scopoletin (8) and fraxetin (9)], a stilbene [(E)-3,3'-dimethoxy-4,4'-dihydroxystilbene (10)], and 13 phenolic derivatives [2-hydroxy-3',4'-dihydroxyacetophenone (11), 1-(2,3,4-trihydroxy-5-methylphenyl)ethanone (12), 2,4,5-trihydroxyacetophenone (13), catechaldehyde (14), vanillin (15), syringaldehyde (16), gallic acid (17), trimethyl gallic acid methyl ester (18), syringic acid (19), syringenin (20), (E)-coniferol (21), C-veratroylglycol (22), and catechol (23)]. The antioxidant activities of MS-BuOH (IC50>1000 μg/mL), pure compounds, vitamin C (IC50=58 μM), and a synthetic commercial antioxidant, butylated hydroxytoluene (IC50=2651 μM), were evaluated in the diphenylpicrylhydrazyl (DPPH) radical scavenging assay. Among the isolates, the phenolic derivatives and coumarins showed superior antioxidant activity (IC50<100 μM) compared to the lignans and stilbene (IC50>100 μM). Also, this is the first report of 16 of these 23 phenolics, that is, compounds 1, 2, 4-14, 18, 20, and 22, in maple syrup.     

The Effect of Bioprocessing on the Phenolic Acid Composition and Antioxidant Activity of Wheat Bran

In the present study, bioprocessing with eight microbial strains including Bacillus species, yeasts, and filamentous fungi was evaluated for its potential to improve the phenolic acid composition and antioxidant activity of wheat bran. The soluble free and soluble conjugated fractions of ethanolic extracts of the treated bran samples were compared for their total phenolic contents, phenolic acid composition, and in vitro antioxidant activities. In general, total phenolic content in the soluble free fraction increased significantly, accounting for 241.11 ± 1.25 μg of gallic acid equivalents (GE)/g (Rhizopus oryzae), 230.50 ± 1.05 μg of GE/g (Mucor circinelloides), and 230.19 ± 1.02 μg of GE/g (Saccharomycopsis fibuligera). The phenolic acid composition, especially of the soluble free fraction, was improved most by S. fibuligera (hydroxybenzoic, vanillic, syringic, and trans‐ferulic acids), M. circinelloides (chlorogenic acid), and R. oryzae (protocatechuic, trans‐coumaric, and benzoic acids). Comparatively, bioprocessing exhibited less effectiveness on conjugated phenolic acid composition. Fermented wheat bran displayed enhanced reducing capacity, superoxide anion radical scavenging activity, and 1,1‐diphenyl‐2‐picrylhydrazyl radical scavenging activity in comparison with the nonfermented sample. The antioxidant activity was significantly correlated to the total phenolic content.     

A universal HPLC method for the determination of phenolic acids in compound herbal medicines

A universal method to separate and quantify 13 phenolic acids (gallic acid, chlorogenic acid, gentsic acid, vanillic acid, caffeic acid, syringic acid, sinapic acid, p-coumaric acid, ferulic acid, anisic acid, rosmarinic acid, salicylic acid, and cinnamic acid) in some compound herbal medicines was established by liquid chromatographic (HPLC). On an Agela XBP-C18 (5 microm, 4.6 mm x 150 mm) column, a multistep binary gradient elution program and a simplified sample pretreatment approach were used in the experiment. For all of the phenolic acids, detection limits ranged around 0.01 mg/L. Linear ranges of higher than 2 orders of magnitude were obtained with a correlation coefficient of 0.9991 to 1. Repeatability was 0.39-2.24% (relative standard deviation, RSD) for intraday, 1.17-3.96% (RSD) for interday, and 0.14-5.33% (RSD) for drug sample analysis. Recovery, tested by a standard addition method, ranged from 83.3% to 104.9% for various trace phenolic acids.     

Allelochemicals in wheat (Triticum aestivum l.): variation of phenolic acids in root tissues

Analysis by GC/MS/MS showed that a worldwide collection of 58 wheat accessions differed significantly in the production of seven phenolic acids in the roots of 17-day-old wheat seedlings. The allelochemical contents among wheat accessions ranged from 24.5 to 94.5, 19.9 to 91.7, 3.7 to 15.4, 2.2 to 38.6, 1.0 to 42.2, 19.3 to 183.6, and 11.7 to 187.6 mg/kg of root dry weight for p-hydroxybenzoic, vanillic, cis-p-coumaric, syringic, cis-ferulic, trans-p-coumaric, and trans-ferulic acids, respectively. trans-Ferulic acid was identified as the most predominant phenolic acid in the roots. Phenolic acids, with the exception of syringic acid, were more concentrated in roots than in shoots. Significant correlation was found between the roots and the shoots in the contents of vanillic, cis-p-coumaric, syringic, trans-p-coumaric, and trans-ferulic acids, and in the content of each structural group of phenolic acids. Wheat accessions with high levels of total identified phenolic acids in the roots were generally strongly allelopathic to the growth of annual ryegrass.     

Individual and combined antioxidant effects of seven phenolic agents in human erythrocyte membrane ghosts and phosphatidylcholine liposome systems: importance of the partition coefficient

Antioxidant activities of seven phenolic agents against Fe(2+)-induced lipid oxidation were compared with alpha-tocopherol, beta-carotene, and vitamin C in human erythrocyte membrane ghosts and liposome systems. The antioxidant activity of five test flavonoids followed the order catechin > epicatechin > rutin > quercetin > myricetin in both systems (p < 0.05), which was negatively correlated with their partition coefficients. The antioxidant interaction of these phenolic agents with alpha-tocopherol, beta-carotene, or vitamin C in inhibiting Fe(2+)-induced lipid oxidation was examined. Synergistic effects were present in the combinations of alpha-tocopherol plus caffeic acid, catechin, or epicatechin as well as in all combinations of vitamin C plus phenolic antioxidants. On the basis of the stronger individual and combined effects present in caffeic acid, catechin, and epicatechin, the application of these three phenolic agents with or without alpha-tocopherol, beta-carotene, and vitamin C may provide stronger protective benefits against lipid oxidation, which may be helpful for oxidation-related diseases prevention.