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PubMed2001

Resveratrol and a novel tyrosinase in Carignan grape juice.

Polyphenol levels in wines are affected by the wine-making process. Resveratrol is one polyphenol which has been the subject of a commendable amount of recent research. In this work, we found that resveratrol is immediately degraded by tyrosinase. A novel tyrosinase was purified from Carignan grapes. The purification process included salting out and separation on a cation-exchange column, followed by gel filtration. Tyrosinase was purified in a homogeneous form by SDS-PAGE and was characterized: its specific activity toward 3-(3,4-dihydroxyphenyl)-L-alanine (DOPA) increased by a factor of 24 with an overall recovery of 3% of initial activity. The apparent molecular mass of the purified tyrosinase was 40 kDa as determined by SDS-PAGE, and 42 kDa as determined by gel filtration. Its activity was optimal at pH 6 and at 25 degrees C. The enzyme exhibited high activity toward phenylenediamine, epicatechin, pyrogallol, DOPA, and resveratrol. Tyrosinase activity was inhibited by KCN, thiourea, and SO(2). Resveratrol levels were stable following the removal of proteins from the juice, suggesting that early spraying of grapes with SO(2) is an important factor affecting the final amount of resveratrol in wine.

Antioxidants↗

PubMed2002

Diphenol activation of the monophenolase and diphenolase activities of field bean (Dolichos lablab) polyphenol oxidase.

This paper reports a study on the hydroxylation of ferulic acid and tyrosine by field bean (Dolichos lablab) polyphenol oxidase, a reaction that does not take place without the addition of catechol. A lag period similar to the characteristic lag of tyrosinase activity was observed, the length of which decreased with increasing catechol concentration and increased with increasing ferulic acid concentration. The activation constant K(a) of catechol for ferulic acid hydroxylation reaction was 5 mM. The kinetic parameters of field bean polyphenol oxidase toward ferulic acid and tyrosine were evaluated in the presence of catechol. 4-Methyl catechol, L-dihydroxyphenylalanine, pyrogallol, and 2,3,4-trihydroxybenzoic acid, substrates with high binding affinity to field bean polyphenol oxidase, could stimulate this hydroxylation reaction. In contrast, diphenols such as protocatechuic acid, gallic acid, chlorogenic acid, and caffeic acid, which were not substrates for the oxidation reaction, were unable to bring about this activation. It is most likely that only o-diphenols that are substrates for the diphenolase serve as cosubstrates by donating electrons at the active site for the monophenolase activity. The reaction mechanism for this activation is consistent with that proposed for tyrosinase (Sanchez-Ferrer, A.; Rodriguez-Lopez, J. N.; Garcia-Canovas, F.; Garcia-Carmona, F. Biochim. Biophys. Acta 1995, 1247, 1-11). The presence of o-diphenols, viz. catechol, L-dihydroxyphenylalanine, and 4-methyl catechol, is also necessary for the oxidation of the diphenols, caffeic acid, and catechin to their quinones by the field bean polyphenol oxidase. This oxidation reaction occurs immediately with no lag period and does not occur without the addition of diphenol. The kinetic parameters for caffeic acid (K(m) = 0.08 mM, V(max) = 32440 u/mg) in the presence of catechol and the activation constant K(a) of catechol (4.6 mM) for this reaction were enumerated. The absence of a lag period for this reaction indicates that the diphenol mechanism of diphenolase activation differs from the way in which the same o-diphenols activate the monophenolase activity.

Benzoquinones↗

PubMed2002

Antioxidant activity of dodecyl gallate.

Dodecyl (C12) gallate exhibits both potent chain-breaking and preventive antioxidant activity. The pyrogallol moiety is responsible for both activities. Dodecyl (lauryl) gallate prevents generation of superoxide radicals by xanthine oxidase, and this activity comes from its ability to inhibit the enzyme. The inhibition kinetics analyzed by Lineweaver-Burk plots found that dodecylgallate is a noncompetitive inhibitor for the generation of superoxide anion. Dodecyl gallate also inhibits formation of uric acid. The inhibition kinetics analyzed by Lineweaver-Burk plots found that dodecyl gallate is a competitive inhibitor for this oxidation. Mitochondrial lipid peroxidation induced by Fe(III)-adenosine 5'-diphosphate/reduced nicotinamide adenine dinucleotide was inhibited by dodecyl gallate while its parent compound, gallic acid, did not show this inhibitory activity. Dodecyl gallate protected mitochondrial functions and human red blood cells against oxidative stresses, but gallic acid showed little effect. The hydrophobic dodecyl group is largely associated with the preventive antioxidative activity.

Animals↗

PubMed2003

Purification and characterization of a peroxidase from corn steep water.

Three cationic peroxidases have been detected in early, middle, and late corn steep water, with pI values of approximately 8.9, approximately 9.5, and >10.0. The major cationic corn steep water peroxidase (CSWP), with a pI >10, was purified 36400-fold with a 12% recovery from late steep water by a combination of acetone and ammonium sulfate precipitation and sequential chromatography on CM-cellulose, phenyl-Sepharose, and Sephadex G-75. The UV-vis spectrum of purified CSWP is typical of other plant class III peroxidases. The RZ (A(403)/A(280)) of CSWP was between 2.6 and 2.9. It is not glycosylated and exhibited an M(r) of 30662 +/- 7 by MALDI-TOF MS. The pH optimum of CSWP depends on the substrate, and it is active on 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid), guaiacol, ferulic acid, o-dianisidine, o-phenylenediamine, and pyrogallol but is not active on either syringaldazine or ascorbate. At 75 degrees C and pH 4.5, the enzyme has half-lives of 22.7 min (0 mM Ca(2+)) and 248 min (1 mM Ca(2+)). The enzyme is stable at room temperature (22-25 degrees C), losing <3% of the activity at pH 4.5 and <10% at pH 6.2 over 400 h in the presence of 1 mM Ca(2+).

Amino Acids↗

PubMed2005

Effects of structure on radical-scavenging abilities and antioxidative activities of tea polyphenols: NMR analytical approach using 1,1-diphenyl-2-picrylhydrazyl radicals.

Tea (Camellia sinensis) leaves contain various antioxidants such as ascorbic acid (1) and polyphenols. This study tries to clarify the molecular mechanisms underlying the antioxidative and radical-scavenging activities of these antioxidants, and the reactivities of each antioxidant have been compared against that of the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH, 2) using nuclear magnetic resonance (NMR) analysis. Catechol (3) and (+)-taxifolin (4) were oxidized to o-quinone by 2. However, ethyl protocatechuate (5) and quercetin (6) were not oxidized to o-quinone, even though they possess a catechol structure. The radical-scavenging ability of o-dihydroxyl phenolic compounds with a conjugated olefinic double bond (e.g., 6) was superior to that of compounds without this bond (e.g., 4), whereas the ability of o-dihydroxyl phenolic compounds possessing a conjugated carbonyl bond (5) was inferior to that of compounds lacking this bond (3). Vicinal trihydroxyl phenolic compounds with a conjugated olefinic double bond [e.g., myricetin (7)] had an inferior scavenging ability as compared with compounds lacking this bond [e.g., pyrogallol (8)], but 7 was a better scavenger than compounds with a conjugated carbonyl double bond [e.g., ethyl gallate (9)]. In addition, vicinal trihydroxyl phenolic compounds (e.g., 9) were superior to o-dihydroxyl phenolic compounds (e.g., 6). Finally, 1 scavenged radicals more quickly than 8.

Antioxidants↗

PubMed2005

Nuclear magnetic resonance spectroscopic based studies of the metabolism of black tea polyphenols in humans.

Epidemiological studies indicate that a high intake of flavonoids is associated with an improved health status. Tea is one of the most abundant sources of flavonoids in the human diet. The bioavailability and biotransformation of tea flavonoids are, however, not clearly understood. The aim of the present study was to investigate the metabolism of black tea via a nonspecific screening method. (1)H nuclear magnetic resonance (NMR) spectroscopy was used to obtain nonselective profiles of urine samples collected from three human volunteers before and after a single dose of black tea. The complex spectroscopic profiles were interpreted with the use of pattern recognition techniques. Hippuric acid was confirmed as the major urinary black tea metabolite. One previously unknown metabolite was detected and identified as 1,3-dihydroxyphenyl-2-O-sulfate (sulfate conjugate of pyrogallol) using HPLC directly coupled to mass spectrometry and (1)H NMR spectroscopy. This study shows that NMR-pattern recognition studies can be used for the discovery of unknown flavonoid metabolites in humans.

Adult↗

PubMed2004

Novel antioxidant peptides from fermented mushroom Ganoderma lucidum.

Oxidative stress has been linked with the pathogenesis of many human diseases including cancer, aging, and atherosclerosis. The present study investigates the antioxidant activities of peptides isolated from the medicinal mushroom, Ganoderma lucidum. G. lucidum has been shown to possess potent antioxidant activity with little or no side effects. Polysaccharide, polysaccharide-peptide complex, and phenolic components of G. lucidum have been proposed to be responsible for this antioxidant effect. However, research has shown that the G. lucidum peptide (GLP) is the major antioxidant component of G. lucidum. The objective of this study was to evaluate the antioxidant activity of this peptide using different oxidation systems. GLP showed potent antioxidant activities in both lightproof soybean oil and lard systems, assessed by lipid peroxidant value. Compared to butylated hydroxytoluene, GLP showed a higher antioxidant activity in the soybean oil system. Soybean lipoxygenase activity was blocked by GLP in a dose-dependent manner with an IC50 value of 27.1 microg/mL. GLP showed scavenging activity toward hydroxyl radicals produced in a deoxyribose system with an IC50 value of 25 microg/mL, and GLP effectively quenched superoxide radical anion produced by pyrogallol autoxidation in a dose-dependent manner. Malondialdehyde level has been used as the oxidation index in many biological systems. GLP showed substantial antioxidant activity in the rat liver tissue homogenates and mitochondrial membrane peroxidation systems. The auto-hemolysis of rat red blood cells was also blocked by GLP in a dose-dependent manner. On the basis of these results, it is concluded that GLP is the major constituent responsible for the antioxidant activity of G. lucidum. GLP could play an important role in the inhibition of lipid peroxidation in biological systems through its antioxidant, metal chelating, and free radical scavenging activities.

Animals↗

PubMed2004

Comparative study on phenolic content and antioxidant activity during maturation of the olive cultivar Chemlali from Tunisia.

For the first time the identification and quantification of phenolic compounds of the Olea europaea L. cv. Chemlali olive were carried out to examine their profile during maturation. The phenolic composition was studied by using reverse-phase high-performance liquid chromatography during all steps of fruit development. Oleuropein is the abundant phenolic compound in Chemlali olive, and its concentration increases during maturation. An indirect relationship between oleuropein content in olive fruit and hydroxytyrosol was observed. Weak changes in the amounts of the other phenolic monomers and flavonoids were also observed. The total phenolic content varied from 6 to 16 g/kg expressed as pyrogallol equivalents. Its highest level was found at the last maturation period. The antioxidant capacity of olive extracts was evaluated by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl. The IC(50) values of the olive extract ranged from 3.2 to 1.5 microg/mL. There was a correlation between antioxidant activity and total phenolic content of samples. The antioxidant activity increased with maturation. This could be attributed to the increase of the tolal phenol level with fruit development.

Antioxidants↗

PubMed2005

Mechanism of formation of redox-active hydroxylated benzenes and pyrazine in 13C-labeled glycine/D-glucose model systems.

To extend the analytical capabilities of the pyrolysis-gas chromatograph-mass spectrometry system that has been successfully utilized in the past as an integrated reaction, separation, and identification system to study label incorporation patterns in Maillard reaction products, a novel methodology was developed to analyze the composition of nonvolatile residues of the initial reaction products. This was achieved through a postpyrolytic in-situ derivatization technique using trimethylsilyldiethylamine. Application of this technique to the investigation of the nonvolatile products formed during pyrolysis of glucose alone and in the presence of glycine has indicated the formation of several redox-active hydroxylated benzene derivatives such as 1,2,3-trihydroxybenzene (pyrogallol), 1,4-dihydroxybenzene (hydroquinone), 1,2-dihydroxybenzene (catechol), and 2,5-dihydroxypyrazine. Labeling studies have indicated that the intact glucose carbon backbone was involved in the construction of the benzene ring of the hydroxylated benzene derivatives and that dimerization of glycine alone can lead to the formation of 2,5-dihydroxypyrazine.

Benzene↗

PubMed2006

Distinctive antioxidant and antiinflammatory effects of flavonols.

The antioxidant and antiinflammatory effects of flavonols have been suggested to be structure-related. Results revealed that selected flavonols, including fisetin (F), kaempferol (K), morin (MO), myricetin (MY), and quercetin (Q), exhibited distinctive free radical scavenging properties against different kinds of free radicals. The H donation (DPPH bleaching) potential was Q > F approximately equals MY > MO > K, indicating that the presence of a 3',4'-catechol moiety in the B ring correlated with high activity. The 4'-OH in the B ring was suggested to be important for reducing xanthing/xanthine oxidase-generated superoxide; while an additional OH moiety on the ortho sites (3' or 5') attenuated the effect as the observed inhibitory potency was K approximately equals MO > Q > F > MY. The relative inhibitory effect for Fenton-mediated hydroxyl radical was K approximately equals MO approximately equals Q > F > MY. This result implies the involvement of 4-keto, 5-OH region in Fe++ chelating and the negative effect of pyrogallol moiety in the B ring. Similar to the inhibitory activity against a N-formyl-methionyl-leucyl-phenylalanine (f-MLP)-stimulated oxidative burst in human polymorphonuclear neutrophils (PMN), our result showed that the structural peculiarity of the di-OH in the B ring obviously rendered F, Q, and MO more potent as ROS inhibitors than MY and K, which have tri- and mono-OH in the B ring, respectively. All of the previous data indicated that the structure prerequisite to reinforce the free radical scavenging activity varies with the type of free radical. We further analyzed the effects of flavonols on nitric oxide (NO) production in endotoxin-stimulated murine macrophages, RAW264.7 cells. Results showed that all flavonols (up to 10 microM) inhibited NO production without exerting detectable cytotoxicity. F, K, and Q dose-dependently repressed iNOS mRNA expression and prostaglandin E2 (PGE2) production, in part through an attenuating NF-kappaB signaling pathway. This result indicates that flavonols, despite structural similarity, have different antioxidant and antiinflammatory effects.

Animals↗

PubMed2006

Synthesis and structure determination of covalent conjugates formed from the sulfury-roasty-smelling 2-furfurylthiol and di- or trihydroxybenzenes and their identification in coffee brew.

Recent investigations demonstrated that the reaction of odor-active thiols such as 2-furfurylthiol with thermally generated chlorogenic acid degradation products is responsible for the rapid aroma staling of coffee beverages. To get a clear understanding of the molecular mechanisms underlying this aroma staling, the existence of putative phenol/thiol conjugates needs to be verified in coffee. The aim of the present study was therefore to synthesize such conjugates for use as reference substances for LC-MS screening of coffee. To achieve this, catechol, 3-methyl-, 4-methyl-, and 4-ethylcatechol, pyrogallol, hydroxyhydroquinone, 5-O-caffeoylquinic acid, and caffeic acid, respectively, were reacted with 2-furfurylthiol in the presence of iron(III) chloride and air oxygen. After purification, the structures of 25 phenol/thiol conjugates were identified by means of LC-MS/MS and 1D/2D NMR experiments. Using these compounds as reference materials, four conjugates, namely, 3-((2-furylmethyl)sulfanyl)catechol, 3-((2-furylmethyl)sulfanyl)-5-ethylcatechol, 4-((2-furylmethyl)sulfanyl)hydroxyhydroquinone, and 3,4-bis((2-furylmethyl)sulfanyl) hydroxyhydroquinone, were identified for the first time in coffee brew by means of HPLC-MS/MS(MRM). These findings clearly demonstrate catechol, 4-ethylcatechol, and hydroxyhydroquinone as the primary thiol trapping agents involved in the aroma staling of coffee beverages.

Chromatography, High Pressure Liquid↗

PubMed1999

Stabilization of azadirachtin A in neem formulations: effect of some solid carriers, neem oil, and stabilizers.

Formulation of azadirachtin A on attapulgite, kaolinite, fuller's earth, hydrated calcium silicate, and fly ash revealed that it degraded to the tune of 70-95% on different solid carriers as compared to 56% in neem oil, during the 14 day heat storage studies at 54 +/- 1 degrees C in the laboratory. The degradation was reduced by 26-60% on different carriers by employing either anthraquinone or epichlorohydrin as stabilizer. Pyrogallol and hydroquinone enhanced the degradation. The cation exchange capacity and surface area of the carriers revealed a significant negative correlation with t(1/2) of azadirachtin A.

Chemistry, Pharmaceutical↗

PubMed2005

Kinetic study of the quenching reaction of singlet oxygen by flavonoids in ethanol solution.

The quenching rate of singlet oxygen (1O2) by seven kinds of flavonoids (flavone, flavonol, chrysin, apigenin, rutin, quercetin, and myricetin) with 2,3-double bonds has been measured spectrophotometrically in ethanol at 35 degrees C. The overall rate constants kQ (= kq + kr, physical quenching + chemical reaction) increased as the number of OH groups substituted to the flavone skeleton (that is, the total electron-donating capacity of flavonoids) increases. The existence of catechol or pyrogallol structure in the B-ring is essential for the 1O2 quenching of flavonoids. Log kQ was found to correlate with their peak oxidation potentials, E(P); the flavonoids that have smaller E(P) values show higher reactivities. Similarly, log kQ values of flavonoids correlate with the energy level of the highest occupied molecular orbital (E(HOMO)), calculated by the PM3 MO method, and the longest wavelength pi pi* excitation energy (E(ex)). The contribution of the chemical reaction (kr) was found to be negligible in these flavonoids. The kQ values of rutin, quercetin, and myricetin [(1.21 approximately 5.12) x 10(8) M(-1) s(-1)] were found to be larger than those of lipids [(0.9 approximately 6.4) x 10(4) M(-1) s(-1)], amino acids (<3.7 x 10(7) M(-1) s(-1)), and DNA (5.1 x 10(5) M(-1) s(-1)). The result suggests that these flavonoids may contribute to the protection of oxidative damage in foods and plants, by quenching 1O2.

Ethanol↗

PubMed2005

A one-pot regiospecific synthesis of highly functionalized 1,4-benzodioxin derivatives from an electrochemically induced Diels-Alder reaction.

[reaction: see text] The anodic oxidation of pyrogallol derivatives produces chemically unstable o-quinone heterodienes, which are trapped in situ by enamine dienophiles through regiospecific inverse-electron-demand Diels-Alder reactions. The possibility of introducing variations in both cycloaddition partners gives rise to highly substituted 1,4-benzodioxin cycloadducts with up to five elements of diversity. The reactions proceed under mild conditions with a good efficiency. The methodology should be amenable to the assembly of libraries of biologically relevant heterocycles.

Combinatorial Chemistry Techniques↗

PubMed2005

The acid-promoted reaction of the green tea polyphenol epigallocatechin gallate with nitrite ions.

Exposure of 400 microM (-)-epigallocatechin-3-O-gallate (EGCG), the main polyphenolic constituent of green tea, to equimolar concentrations of nitrite ions in 0.5 M HCl at 37 degrees C resulted in the formation of a distinct pattern of products that were trapped as phenazine derivatives by treatment with o-phenylenediamine. Repeated chromatographic fractionation eventually allowed isolation of four main species, which were identified by 2D NMR and MS analysis as 1b, derived from EGCG quinone 1a, the isomeric oximes 2b,c, arising from nitrosation of EGCG on the pyrogallol B-ring, and the dioxime 4b in which the A-ring was doubly substituted. At lower EGCG concentrations (e.g., 25 microM) and at pH 3, reaction with equimolar amounts of nitrite gave 1b as the first formed species, whereas nitrosation products 2b,c and 4b became detectable only with excess nitrite. Similar reaction of chemically prepared 1a with acidic nitrite led to the formation of 2b,c and 4b, suggesting that this quinone may be an intermediate in the nitrosation of EGCG. Exposure of green tea extracts to acidic nitrite ions resulted in the conversion of EGCG to 1a, detected as 1b. Overall these results substantiate literature reports suggesting that the protective effects of EGCG against nitrosation involve mainly an initial redox exchange process and hint at a hitherto unrecognized property of quinone 1a as a potential scavenger of nitrosating species.

Catechin↗

PubMed1998

Silver development in microscopy and bioanalysis: a new versatile formulation for modern needs.

Potentially, silver development could unify most modern demands for clean, accurately localized marker amplification in microscopy and bioanalysis. However, the existing technology leaves room for improvement in developer design. A new formulation has been devised which, by using principles of silver chelation, avoids problems of self-nucleation and catalysis by light. It is made, just before use, by mixing together equal amounts of stock solutions containing high molarity, Tris-buffered silver nitrate and alcoholic, buffered pyrogallol. The two stocks are easily prepared and have very long shelf-lives. The developer is light insensitive for up to an hour at room temperature, so that development can proceed under ambient light conditions and at the neutral pH most suited to biological systems. The powerful reducer in the suggested formulation should allow the detection of low concentrations of marker signal in a wide range of applications.

Humans↗

PubMed1998

Possible mechanism of captopril induced endothelium-dependent relaxation in isolated rabbit aorta.

The mechanism of captopril, an angiotensin converting enzyme (ACE) inhibitor with sulfhydryl group (SH) in its structure, to produce an endothelium-dependent vasorelaxation was studied. In rabbit aorta with intact endothelium and precontracted with phenylephrine, captopril and superoxide dismutase (SOD) produced dose-dependent relaxation. Lisinopril, an ACE inhibitor without a -SH group in its structure, did not produce endothelium-dependent relaxation. It was observed that captopril, like SOD, produced the relaxation by protecting the EDRF from getting inactivated by superoxide anions as pyrogallol and methylene blue inhibited both the captopril and SOD-mediated relaxation. The free radical scavenging action of captopril is further substantiated by the observation that captopril, but not lisinopril, inhibited FeCl3/ascorbic acid-induced lipid peroxidation in whole tissue homogenates of rabbit aorta to a level comparable to that of SOD. These results suggest that endothelium-dependent vasodilation produced by captopril may be due to its ability to scavenge superoxide anion and this property may be ascribed to the -SH group present in its structure.

Angiotensin-Converting Enzyme Inhibitors↗

PubMedDate not supplied

[The determination of total concentration and activity of antioxidants in foodstuffs].

We developed a new method for the analysis of active antioxidants that is based on their reactions with the ABTS+. cation radical obtained by oxidation of ABTS, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt. The feasibility of this method was confirmed by electrochemical and kinetic studies of model antioxidants. ABTS+. was shown to react rapidly with active and slowly with weak antioxidants, which allows it to be used as a model radical for the quantitative determination of the total content of natural antioxidants (antioxidant equivalent) in natural extracts and wines. Another analytical method based on the competitive oxidation of Pyrogallol Red (a detecting molecule) and the examined antioxidants by radicals derived from peroxynitrite was used for measuring the relative activity of antioxidants. A combination of both methods helped measure the total concentration of antioxidants and their average specific activities (per molecule of active compound) in extracts from grape, olive, and tomato and concentrates of various popular beverages (wines, beers, and juices), as well as in the commercial concentrated food product Kréto-A, made from grape, red wine, tomato, and olive. Red wine and red grape juice were shown to be the most rich in antioxidants (up to 20 mM), with their activity being similar to that of polyphenols. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2002, vol. 28, no. 6; see also http://www.maik.ru.

Antioxidants↗