Metabolism of dietary procyanidins in rats

Free Radical Biology and Medicine

Volumn 35, Issue 8, 2003, Pages 837-844

  Gonthier, Marie Paule ^a   Donovan, Jennifer L ^a   Texier, Odile ^b   Felgines, Catherine ^b   Remesy, Christian ^a   Scalbert, Augustin ^a  

^a CEMAGREF   (France)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Antioxidants; Aromatic acids; Catechin; Dietary polyphenols; Free radicals; Gut microflora; Metabolism; Procyanidins

Indexed keywords

BENZENE DERIVATIVE; BENZOIC ACID DERIVATIVE; CATECHIN; DIMER; PROCYANIDIN; PROPIONIC ACID DERIVATIVE; VALERIC ACID DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CONTROLLED STUDY; DIET; INTESTINE; INTESTINE ABSORPTION; INTESTINE FLORA; MALE; METABOLISM; METABOLITE; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; RAT; URINALYSIS; WILLOW;

ANIMALIA; SALIX;

EID: 0141861933     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(03)00394-0     Document Type: Article

References (40)

1. Santos-Buelga C., Scalbert A. Proanthocyanidins and tannin-like compounds nature, occurrence, dietary intake, and effects on nutrition and health . J. Sci. Food Agric. 80:2000;1094-1117.
2. Salah N., Miller N.J., Paganga G., Tijburg L., Bolwell G.P., Rice-Evans C. Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants. Arch. Biochem. Biophys. 322:1995;339-346.
3. Steinberg F.M., Holt R.R., Schmitz H.H., Keen C.L. Cocoa procyanidin chain length does not determine ability to protect LDL from oxidation when monomer units are controlled. J. Nutr. Biochem. 13:2002;645-652.
4. Rein D., Paglieroni T.G., Pearson D.A., Wun T., Schmitz H.H., Gosselin R., Keen C.L. Cocoa and wine polyphenols modulate platelet activation and function. J. Nutr. 130:2000;2120S-2126S.
5. Kashiwada Y., Nonaka G., Nishioka I., Chang J.J., Lee K.H. Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents. J. Nat. Prod. 55:1992;1033-1043.
6. Packer L., Rimbach G., Virgili F. Antioxidant activity and biological properties of a procyanidin-rich extract from Pine (Pinus Maritima) bark, Pycnogenol. Free Radic. Biol. Med. 27:1999;704-724.
7. Osakabe N., Baba S., Yasuda A., Iwamoto T., Kamiyama M., Takizawa T., Itakura H., Kondo K. Daily cocoa intake reduces the susceptibility of low-density lipoprotein to oxidation as demonstrated in healthy human volunteers. Free Radic. Res. 34:2001;93-99.
8. Yamakoshi J., Kataoka S., Koga T., Ariga T. Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits. Atherosclerosis. 142:1999;139-149.
9. Simonetti P., Ciappellano S., Gardana C., Bramati L., Pietta P. Procyanidins from Vitis vinifera seeds in vivo effects on oxidative stress . J. Agric. Food Chem. 50:2002;6217-6221.
10. Bomser J.A., Singletary K.W., Wallig M.A., Smith M.A. Inhibition of TPA-induced tumor promotion in CD-1 mouse epidermis by a polyphenolic fraction from grape seeds. Cancer Lett. 135:1999;151-157.
11. Spencer J.P.E., Chaudry F., Pannala A.S., Kaila Srai S., Debnam E., Rice-Evans C. Decomposition of cocoa procyanidins in the gastric milieu. Biochem. Biophys. Res. Commun. 272:2000;236-241.
12. Zhu Q.Y., Holt R.R., Lazarus S.A., Ensunsa J.L., Hammerstone J.F., Schmitz H.H., Keen C. Stability of the flavan-3-ols epicatechin and catechin and related dimeric procyanidins derived from cocoa. J. Agric. Food Chem. 50:2002;1700-1705.
13. Rios L.Y., Bennet R.N., Lazarus S.A., Rémésy C., Scalbert A., Williamson G. Cocoa procyanidins are stable during gastric transit in humans. Am. J. Clin. Nutr. 76:2002;1106-1110.
14. 5 after transfer across the small intestine. Biochem. Biophys. Res. Commun. 285:2001;588-593.
15. 2. [epicatechin-(4β-8)-epicatechin] in rats Free Radic. Biol. Med. 33:2002;142-148.
16. 2. [epicatechin-(4β-8)-epicatechin] in human plasma after the consumption of a flavanol-rich cocoa Am. J. Clin. Nutr. 76:2002;798-804.
17. 3. Br. J. Nutr. 87:2002;299-306.
18. Hackett A.M., Shaw I.C., Griffiths L.A. 3′-O-Methyl-(+)-catechin glucuronide and 3′-O-methyl-(+)-catechin sulphate new urinary metabolites of (+)-catechin in the rat and the marmoset . Experientia. 38:1982;538-540.
19. Baba S., Osakabe N., Natsume M., Muto Y., Takizawa T., Terao J. In vivo comparison of the bioavailability of (+)-catechin, (-)-epicatechin, and their mixture in orally administered rats. J. Nutr. 131:2001;2885-2891.
20. Gonthier M.-P., Cheynier V., Donovan J.L., Manach C., Morand C., Mila I., Lapierre C., Rémésy C., Scalbert A. Microbial aromatic acid metabolites formed in the gut account for a major fraction of the polyphenols excreted in urine of rats fed red wine polyphenols. J. Nutr. 133:2003;461-467.
21. Rios L.Y., Gonthier M.P., Rémésy C., Mila I., Lapierre C., Lazarus S.A., Williamson G., Scalbert A. Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects. Am. J. Clin. Nutr. 77:2003;912-918.
22. Groenewoud G., Hundt H.K.L. The microbial metabolism of condensed (+)-catechins by rat-cecal microflora. Xenobiotica. 16:1986;99-107.
23. Déprez S., Brézillon C., Rabot S., Philippe C., Mila I., Lapierre C., Scalbert A. Polymeric proanthocyanidins are catabolized by a human colonic microflora into low molecular weight phenolic acids. J. Nutr. 130:2000;2733-2738.
24. Clifford M.N., Copeland E.L., Bloxsidge J.P., Mitchell L.A. Hippuric acid as a major excretion product associated with black tea consumption. Xenobiotica. 30:2000;317-326.
25. Rechner A.R., Kuhnle G., Bremner P., Hubbard G.P., Moore K.P., Rice-Evans C.A. The metabolic fate of dietary polyphenols in humans. Free Radic. Biol. Med. 33:2002;220-235.
26. Gonthier M.-P., Verny M.-A., Besson C., Rémésy C., Scalbert A. Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J. Nutr. 133:2003;1853-1859.
27. Déprez S., Scalbert A. Carbon-14 biolabeling of (+)-catechin and proanthocyanidin oligomers in willow tree cuttings. J. Agric. Food Chem. 47:1999;4219-4230.
28. Donovan J.L., Crespy V., Manach C., Morand C., Besson C., Scalbert A., Rémésy C. Catechin is metabolized by both the small intestine and the liver in rats. J. Nutr. 131:2000;1753-1757.
29. Gonthier M.-P., Rios L.Y., Verny M.-A., Rémésy C., Scalbert A. Novel liquid chromatography-electrospray ionization mass spectrometry method for the quantification in human urine of microbial aromatic acid metabolites derived from dietary polyphenols. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 789:2003;247-255.
30. Scheline R.R. Handbook of mammalian metabolism of plant compounds. 1991;CRC Press, Boca Raton, FL.
31. Griffiths L.A. Studies on flavonoid metabolism. Identification of the metabolites of (+)-catechin in rat urine. Biochem. J. 92:1964;173-179.
32. Quick A.J. The conjugation of benzoic acid in man. J. Biol. Chem. 92:1931;65.
33. 14C]cyanidol-3 in man following oral administration Xenobiotica. 13:1983;279-286.
34. Curtius H.C., Mettler M., Ettlinger L. Study of the intestinal tyrosine metabolism using stable isotopes and gas chromatography-mass spectrometry. J. Chromatogr. 126:1976;569-580.
35. Scalbert A. Antimicrobial properties of tannins. Phytochemistry. 30:1991;3875-3883.
36. Scalbert A., Morand C., Manach C., Rémésy C. Absorption and metabolism of polyphenols in the gut and impact on health. Biomed. Pharmacother. 56:2002;246-282.
37. Rice-Evans C.A., Miller N.J., Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20:1996;933-956.
38. Natella F., Nardini M., Di Felice M., Scaccini C. Benzoic and cinnamic acid derivatives as antioxidants structure-activity relation . J. Agric. Food Chem. 47:1999;1453-1459.
39. Raneva V., Shimasaki H., Ishida Y., Ueta N., Niki E. Antioxidative activity of 3,4-dihydroxyphenylacetic acid and caffeic acid in rat plasma. Lipids. 36:2001;1111-1116.
40. Kim D.-H., Jung E.-A., Sohng I.-S., Han J.-A., Kim T.-H., Han M.J. Intestinal bacterial metabolism of flavonoids and its relation to some biological activities. Arch. Pharm. Res. 21:1998;17-23.