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Original Article

Reaction pH and protein affect the oxidation products of β-pentagalloyl glucose

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Pages 117-124 | Received 22 Jul 2004, Published online: 07 Jul 2009

References

  • Hagerman AE, Rice ME, Ritchard NT. Mechanisms of protein precipitation for two tannins, pentagalloyl glucose and epicatechin16-(4 8)-catechin (procyanidin). J Agric Food Chem 1998;46: 2590–2595.
  • Chen Y, Hagerman AE. Characterizing soluble non-covalent complexes between bovine serum albumin and 13-1,2,3,4,6-penta-0-galloyl-n-glucopyranose by MALDI-TOF mass spec-trometry. J Agric Food Chem 2004;52:4008–4011.
  • Haslam E, Lilley TH, Cai Y, Martin R, Magnolato D. Traditional herbal medicines—the role of polyphenols. Planta Med 1989;55:1–8.
  • Wroblewski K, Muhandiram R, Chakrabartty A, Bennick A. The molecular interaction of human salivary histatins with polyphenolic compounds. Eur J Biochem 2001; 268:4384–4397.
  • Raha S, Robinson BH. Mitochondria, oxygen free radicals, disease and aging. Trends Biochem Sci 2000;25:502–508.
  • Droge W. Free radicals in the physiological control of cell function. Physiol Rev 2002;82:47–95.
  • Vandervliet A, Bast A. Role of reactive oxygen species in intestinal diseases. Free Radic Biol Med 1992;12:499–513.
  • Blau S, Rubinstein A, Bass P, Singaram C, Kohen R Differences in the reducing power along the rat GI tract: lower antioxidant capacity of the colon. Mol Cell Biochem 1999;194:185–191.
  • Aw TY. Molecular and cellular responses to oxidative stress and changes in oxidation-reduction imbalance in the intestine. Am J Chin Nutr 1999;70:565–577.
  • Srigiridhar K, Nair KM. Supplementation with alpha-tocopherol or a combination of alpha-tocopherol and ascorbic acid protects the gastrointestinal tract of iron-deficient rats against iron-induced oxidative damage during iron repletion. Br J Nutr 2000;84:165–173.
  • Anton PM, Theodorou V, Bertrand V, Eutamene H, Aussenac T, Feyt N, Fioramonti J, Bueno L. Chronic ingestion of a potential food contaminant induces gastrointestinal inflam-mation in rats—role of nitric oxide and mast cells. Dig Dis Sci 2000;45:1842–1849.
  • Zheng W, Sellers TA, Doyle TJ, Kushi LH, Potter JD, Folsom AR. Retinol, antioxidant vitamins, and cancers of the upper digestive-tract in a prospective cohort study of postmenopau-sal women. Am J Epidemiol 1995;142:955–960.
  • Rice-Evans C. Flavonoid antioxidants. Curr Med Chem 2001;8:797–807.
  • Bagchi M, Milnes M, Williams C, Balmoori J, Ye XM, Stohs S, Bagchi D. Acute and chronic stress-induced oxidative gastrointestinal injury in rats, and the protective ability of a novel grape seed proanthocyanidin extract. Nutr Res 1999;19:1189–1199.
  • Halliwell B, Zhao KC, Whiteman M. The gastrointestinal tract: a major site of antioxidant action? Free Radic Res 2000;33:819–830.
  • Hagerman AE, Riedl KM, Jones GA, Sovik KN, Ritchard NT, Hartzfeld PW, Riechel TL. High molecular weight plant polyphenolics (tannins) as biological antioxidants. J Agric Food Chem 1998;46:1887–1892.
  • Bors W, Foo LY, Hertkorn N, Michel C, Stettmaier K. Chemical studies of proanthocyanidins and hydrolyzable tannins. Antioxid Redox Signal 2001;3:995–1008.
  • Hagerman AE. Polymeric phenolics as antioxidants. Polyphenols Actualites 2001;:17–22.
  • Santos-Buelga C, Scalbert A. Proanthocyanidins and tannin-like compounds—nature, occurrence, dietary intake and effects on nutrition and health. J Sci Food Agric 2000; 80:1094–1117.
  • Gunckel S, Santander P, Cordano G, Ferreira J, Munoz S, Nunez-Vergara U, Squella JA. Antioxidant activity of gallates: an electrochemical study in aqueous media. Chem Biol Interact 1998;114:45–59.
  • Barclay LRC, Edwards CE, Vinqvist MR. Media effects on antioxidant activities of phenols and catechols. J Am Chem Soc 1999;121:6226–6231.
  • Snelgrove DW, Lusztyk J, Banks JT, Mulder P, Ingold KU. Kinetic solvent effects on hydrogen-atom abstractions: reliable, quantitative predictions via a single empirical equation. J Am Chem Soc 2001;123:469–477.
  • Kumamoto M, Sonda T, Nagayama K, Tabata M. Effects of pH and metal ions on antioxidative activities of catechins. Biosci Biotechnol Biochem 2001;65:126–132.
  • Riedl KM, Hagerman AE. Tannin-protein complexes as radical scavengers and radical sinks. J Agric Food Chem 2001;49:4917–4923.
  • Arts MJTJ, Haenen GRMM, Voss HP, Bast A. Masking of antioxidant capacity by the interaction of flavonoids with protein. Food Chem Toxicol 2001;39:787–791.
  • Foti MC, Barclay LRC, Ingold KU. The role of hydrogen bonding on the H-atom-donating abilities of catechols and naphthalene diols and on a previously overlooked aspect of their infrared spectra. J Am Chem Soc 2002; 124:12881–12888.
  • Bilia A, Carelli V, Dicolo G, Nannipieri E. In vitro evaluation of a pH-sensitive hydrogel for control of gi drug delivery from silicone-based matrices. Int. J Pharm 1996;130:83–92.
  • Davidson JM, Linforth RST, Taylor AJ. In-mouth measure-ment of pH and conductivity during eating. J Agric Food Chem 1998;46:5210–5214.
  • Chen Y, Hagerman AE, Minto RE. Preparation of 1,2,3,4,6-penta-0-galloy1-[U-14C]-D-glucopyranose. J Label Compd Radiopharm 2003;46: 99–105.
  • Hagerman AE, Butler LG. Determination of protein in tannin-protein precipitates. J Agric Food Chem 1980; 28:944–947.
  • Hagerman AE, Butler LG. Condensed tannin purification and characterization of tannin-associated proteins. J Agric Food Chem 1980;28:947–952.
  • Chen Y, Hagerman AE. Quantitative examination of oxidized polyphenol-protein complexes. J Agric Food Chem 2004; 52:6061–6067.
  • Yuu ME, Hwang JY, Deming TJ. Role of 1–3,4-dihydroxy-phenylalanine in mussel adhesive proteins. J Am Chem Soc 1999;121: 5825–5826.
  • Dangles 0, Dufour C, Bret S. Flavonol-serum albumin complexation. Two-electron oxidation of flavonols and their complexes with serum albumin. J Chem Soc Perk Trans 1999;2:737–744.
  • Liberato DJ, Byers VS, Dennick RG, Castagnoli N. Regiospecific attack of nitrogen and sulfur nucleophiles on quinones derived from poison oak-ivy catechols (urushiols) and analogs as models for urushiol-protein conjugate formation. J Med Chem 1981;24:28–33.
  • Paz MA, Fluckiger R, Boak A, Kagan HM, Gallop PM. Specific detection of quinoproteins by redox-cycling staining. J Biol Chem 1991;266:689–692.
  • Kalyanaraman B, Premovic PI, Sealy RC. Semiquinone anion radicals from addition of amino-acids, peptides, and proteins to quinones derived from oxidation of catechols and catecholamines-an electron-spin-resonance spin stabilization study. J Biol Chem 1987;262:11080–11087.
  • Bors W, Michel C, Stettmaier K. Electron paramagnetic resonance studies of radical species of proanthocyanidins and gallate esters. Arch Biochem Biophys 2000;374:347–355.
  • Hagerman AE, Dean RT, Davies MJ. Radical chemistry of epigallocatechin gallate and its relevance to protein damage. Arch Biochem Biophys 2003;414:115–120.
  • Kawamoto H, Nakatsubo F. Effects of environmental factors on two-stage tannin-protein co-precipitation. Phytochemistry 1997;46:479–483.
  • Jovanovic SV, Hara Y, Steenken S, Simic MG. Antioxidant potential of gallocatechins-a pulse-radiolysis and laser photolysis study. J Am Chem Soc 1995;117:9881–9888.
  • Hagerman AE, Butler LG. The specificity of proanthocyani-din-protein interactions. J Biol Chem 1981;256:4494–4497.
  • Bi JL, Felton GW, Murphy JB, Howles PA, Dixon RA, Lamb CJ. Do plant phenolics confer resistance to specialist and generalist insect herbivores? J Agric Food Chem 1997;45:4500–4504.
  • Khan FH, Saha M, Chakrabarti S. Dopamine induced protein damage in mitochondrial-synaptosomal fraction of rat brain. Brain Res 2001;895:245–249.
  • Dean RT, Fu SL, Stocker R, Davies MJ. Biochemistry and pathology of radical-mediated protein oxidation. Biochem J 1997;324:1–18.
  • Kroll J, Rawel HM, Seidelmann N. Physicochemical proper-ties and susceptibility to proteolytic digestion of myoglobin-phenol derivatives. J Agric Food Chem 2000;48:1580–1587.
  • Peter MG. Chemical modifications of bio-polymers by quinones and quinone methides. Angew Chem hit Ed Engl 1989;28:555–570.
  • Simon SA, Disalvo EA, Gawrisch K, Borovyagin V, Toone E, Schiffman SS, Needham D, Mcintosh TJ. Increased adhesion between neutral lipid bilayers-interbilayer bridges formed by tannic-acid. Biophys J 1994;66:1943–1958.
  • Huh NW, Porter NA, Mcintosh TJ, Simon SA. The interaction of polyphenols with bilayers: conditions for increasing bilayer adhesion. Biophys J 1996;71:3261–3277.

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