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Original Article

In Vitro Antioxidative Activity of (−)-Epicatechin Glucuronide Metabolites Present in Human and Rat Plasma

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Pages 1341-1348 | Received 05 Jul 2004, Published online: 07 Jul 2009

References

  • Hertog, M.G., Feskens, E.J., Hollman, P.C., Katan, M.B. and Kromhout, D. (1993) "Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study", Lancet 342, 1007–1011.
  • Hertog, M.G., Kromhout, D., Aravanis, C., Blackburn, H., Buzina, R., Fidanza, E, Giampaoli, S., Jansen, A., Menotti, A., Nedeljkovic, S., Pekkarinen, M., Simic, B.S., Tohima, H., Feskens, E.J.M., Hollman, P.C.H. and Katan, M.B. (1995) "Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study", Arch. Intern. Med. 155, 381–386.
  • Knekt, P., Jarvinen, R., Reunanen, A. and Maatela, J. (1996) "Flavonoid intake and coronary mortality in Finland: a cohort study", BMJ 312, 478–481.
  • Arts, I.C.W., Hollman, P.C.H., Feskens, E.J.M., Bueno de Mesquita, H.B. and Kromhout, D. (2001) "Catechin intake might explain the inverse relation between tea consumption and ischemic heart disease: the Zutphen Elderly Study", Am. J. Clin. Nutr. 74, 227–232.
  • Arts, I.C.W., Jacobs, Jr., D.R., Harnack L.J., Gross, M. and Folsom, A.R. (2001) "Dietary catechins in relation to coronary heart disease death among postmenopausal women", Epidemiology 12, 668–675.
  • Arts, I.C.W., van de Putte, B. and Hollman, P.C.H. (2000) "Catechin contents of foods commonly consumed in The Netherlands. 1. Fruits, vegetables, staple foods, and pro-cessed foods", J. Agric. Food Chem. 48, 1746–1751.
  • Shibusawa, Y., Yanagida, A., Isozaki, M., Shindo, H. and Ito, Y. (2001) "Separation of apple procyanidins into different degrees of polymerization by high-speed counter-current chromatography", J. Chromatogr. A 915, 253–257.
  • Piskula, M.K. and Terao, J. (1998) "Accumulation of (— )-epicatechin metabolites in rat plasma after oral adminis-tration and distribution of conjugation enzymes in rat tissues", J. Nutr. 128, 1172–1178.
  • Baba, S., Osakabe, N., Natsume, M., Yasuda, A., Takizawa, T., Nakamura, T. and Terao, J. (2000) "Cocoa powder enhances the level of antioxidative activity in rat plasma", Br. J. Nutr. 84, 673–680.
  • Baba, S., Osakabe, N., Yasuda, A., Natsume, M., Takizawa, T., Nakamura, T. and Terao, J. (2000) "Bioavailability of (— )-epicatechin upon intake of chocolate and cocoa in human volunteers", Free Radic. Res. 33, 635–641.
  • Natsume, M., Osakabe, N., Oyama, M., Sasaki, M., Baba, S., Nakamura, Y., Osawa, T. and Terao, J. (2003) "Structures of (— )-epicatechin glucuronide identified from plasma and urine after oral ingestion of (—)-epicatechin: differences between human and rat", Free Radic. Biol. Med. 34, 840–849.
  • Moon, J., Tsushida, T., Nakahara, K. and Terao, J. (2001) "Identification of quercetin 3-0-13-o-glucuronide as an antioxidative metabolite in rat plasma after oral adminis-tration of quercetin", Free Radic. Biol. Med. 30, 1274–1285.
  • Harada, M., Kan, Y, Naoki, H., Fukui, Y., Kageyama, N., Nakai, M., Mild, W. and Kiso, Y. (1999) "Identification of the major antioxidative metabolites in biological fluids of the rat with ingested (+ )-catechin and ( — )-epicatechin", Biosci. Biotechnol. Biochem. 63, 973–977.
  • Ukeda, H., Sarker, A., Kawana, D. and Sawamura, M. (1999) "Flow-injection assay of superoxide dismutase based on the reduction of highly water-soluble tetrazolium", Anal. Sci. 15, 353–357.
  • Ohkawa, H., Ohishi, N. and Yagi, K. (1979) "Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction", Anal. Biochem. 95, 351–358.
  • Esterbauer, H., Striegl, G., Puhl, H. and Rotheneder, M. (1989) "Continuous monitoring of in vitro oxidation of human low density lipoprotein", Free Radic. Res. Commun. 6, 67–75.
  • Hirano, R., Osakabe, N., Iwamoto, A., Matsumoto, A., Natsume, M., Takizawa, T., Igarashi, 0., Itakura, H. and Kondo, K. (2000) "Antioxidant effects of polyphenols in chocolate on low-density lipoprotein both in vitro and ex vivo", J. Nutr. Sci. Vitaminol. (Tokyo) 46, 199–204.
  • Chun, Y.J., Kim, M.Y. and Guengerich, EP. (1999) "Resveratrol is a selective human cytochrome P450 1A1 inhibitor", Biochem. Biophys. Res. Commun. 262, 20–24.
  • Steinberg, EM., Holt, R.R., Schmitz, H.H. and Keen, C.L. (2002) "Cocoa procyanidin chain length does not determine ability to protect LDL from oxidation when monomer units are controlled", J. Nutr. Biochem. 13, 645–652.
  • Osakabe, N., Yasuda, A., Natsume, M., Takizawa, T., Terao, J. and Kondo, K. (2002) "Catechins and their oligomers linked by C4 C8 bonds are major cacao polyphenols and protect low-density lipoprotein from oxidation in vitro", Exp. Biol. Med. (Maywood) 227, 51–56.
  • Teissedre, Pi., Frankel, E.N., Waterhouse, A.L., Peleg, H. and German, J.B. (1996) "Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines", J. Sci. Food Agric. 70, 55–61.
  • Frankel, E.N., Kanner, J., German, J.B., Parks, E. and Kinsella, J.E. (1993) "Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine", Lancet 341, 454–457.
  • Yamakoshi, J., Kataoka, S., Koga, T. and Ariga, T. (1999) "Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits", Atherosclerosis 142, 139–149.
  • Lu, Y. and Foo, L.Y. (2000) "Antioxidant and radical scavenging activities of polyphenols from apple pomace", Food Chem. 68, 81–85.
  • Bors, W., Heller, W., Michel, C. and Saran, M. (1990) "Flavonoids as antioxidants: determination of radical-scavenging efficiencies", Methods Enzymol. 186, 343–355.
  • Lotito, S.B. and Fraga, C.G. (1998) "(+)-Catechin prevents human plasma oxidation", Free Radic. Biol. Med. 24, 435–441.
  • Lotito, S.B. and Fraga, C.G. (2000) "Catechins delay lipid oxidation and a-tocopherol and 13-carotene depletion following ascorbate depletion in human plasma", Proc. Soc. Exp. Biol. Med. 225, 32–38.
  • Baba, S., Osakabe, N., Natsume, M., Muto, Y, Takizawa, T. and Terao, J. (2001) "Absorption and urinary excretion of (— )-epicatechin after administration of different levels of cocoa powder or (— )-epicatechin in rats", J. Agric. Food Chem. 49, 6050–6056.
  • Steinberg, D., Parthasarathy, S., Carew, T.E., Khoo, J.C. and Witztum, J.L. (1989) "Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity", N. Engl. J. Med. 320, 915–924.
  • Parthasarathy, S., Printz, D.J., Boyd, D., Joy, L. and Steinberg, D. (1986) "Macrophage oxidation of low density lipoprotein generates a modified form recognized by the scavenger receptor", Arteriosclerosis 6, 505–510.
  • Berliner, J.A., Navab, M., Fogelman, A.M., Frank, J.S., Demer, L.L., Edwards, P.A., Watson, AD. and Lusis, A.J. (1995) "Atherosclerosis: basic mechanisms. Oxidation, inflam-mation, and genetics", Circulation 91, 2488–2496.
  • Kaplan, M. and Aviram, M. (1999) "Oxidized low density lipoprotein: atherogenic and proinflammatory characteristics during macrophage foam cell formation. An inhibitory role for nutritional antioxidants and serum paraoxonase", Clin. Chem. Lab. Med. 37, 777–787.
  • Zettler, M.E. and Pierce, G.N. (2001) "Growth-promoting effects of oxidized low density lipoprotein", Can. J. Cardiol. 17, 73–79.
  • Marathe, G.K., Prescott, S.M., Zimmerman, G.A. and McIntyre, T.M. (2001) "Oxidized LDL contains inflammatory PAF-like phospholipids", Trends Cardiovasc. Med. 11, 139–142.
  • Witztum, J.L. and Steinberg, D. (1991) "Role of oxidized low density lipoprotein in atherogenesis", J. Clin. Investig. 88, 1785–1792.
  • Parthasarathy, S., Young, S.G., Witztum, J.L., Pittman, R.C. and Steinberg, D. (1986) "Probucol inhibits oxidative modification of low density lipoprotein", J. Clin. Investig. 77, 641–644.
  • Lavy, A., Ben Amotz, A. and Aviram, M. (1993) "Preferential inhibition of LDL oxidation by the all-trans isomer of beta-carotene in comparison with 9-cis beta-carotene", Fur. J. Clin. Chem. Clin. Biochem. 31, 83–90.
  • Upritchard, J.E., Schuurman, C.R., Wiersma, A., Tijburg, L.B., Coolen, S.A., Rijken, P.J. and Wiseman, S.A. (2003) "Spread supplemented with moderate doses of vitamin E and carotenoids reduces lipid peroxidation in healthy, nonsmok-ing adults", Am. J. Clin. Nutr. 78, 985–992.
  • Osakabe, N., Baba, S., Yasuda, A., Iwamoto, T., Kamiyama, M., Takizawa, T., Itakura, H. and Kondo, K. (2001) "Daily cocoa intake reduces the susceptibility of low-density lipoprotein to oxidation as demonstrated in healthy human volunteers", Free Radic. Res. 34, 93–99.
  • Natsume, M., Osakabe, N., Yamagishi, M., Takizawa, T., Nakamura, T., Miyatake, H., Hatano, T. and Yoshida, T. (2000) "Analyses of polyphenols in cacao liquor, cocoa, and chocolate by normal-phase and reversed-phase HPLC", Biosci. Biotechnol. Biochem. 64, 2581–2587.
  • Manach, C., Morand, C., Crespy, V, Demigne, C., Texier, 0., Regerat, F. and Remesy, C. (1998) "Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties", FEBS Lett. 426, 331–336.
  • Afanas'ev, I.B., Dorozhko, Al., Brodskii, A.V., Kostyuk, V.A. and Potapovitch, Al. (1989) "Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation", Biochem. Pharmacol. 38, 1763–1769.
  • Kondo, K., Hirano, R., Matsumoto, A., Igarashi, 0. and Itakura, H. (1996) "Inhibition of LDL oxidation by cocoa", Lancet 348, 1514.
  • Manach, C. and Donovan, J.L. (2004) "Pharmacokinetics and metabolism of dietary flavonoids in humans", Free Radic. Res. 38, 771–785.
  • Baba, S., Osakabe, N., Natsume, M. and Terao, J. (2002) "Absorption and urinary excretion of procyanidin B2 [epicatechin-(4-beta-8)-epicatechin] in rats", Free Radic. Biol. Med. 33, 142–148.
  • Shimoi, K., Saka, N., Nozawa, R., Sato, M., Amano, I., Nakayama, T. and Kinae, N. (2001) "Deglucuronidation of a flavonoid, luteolin monoglucuronide, during inflammation", Drug Metab. Dispos. 29, 1521–1524.
  • Halliwell, B. (2003) "Plasma antioxidants: health benefits of eating chocolate?", Nature 426, 787, discussion 788.
  • Deprez, S., Brezillon, C., Rabot, S., Philippe, C., Mila, I., Lapierre, C. and Scalbert, A. (2000) "Polymeric proantho-cyanidins are catabolized by human colonic microflora into low-molecular-weight phenolic acids", J. Nutr. 130, 2733–2738.

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