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Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products

Rechner, A.R., Smith, M.A., Kuhnle, G., Gibson, G.R., Debnam, E.S., Srai, S.K.S., Moore, K.P. and Rice-Evans, C.A. (2004) Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. Free Radical Biology and Medicine, 36 (2). pp. 212-225. ISSN 0891-5849

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To link to this article DOI: 10.1016/j.freeradbiomed.2003.09.022

Abstract/Summary

The metabolism of chlorogenic acid., naringin, and rutin, representative members of three common families of dietary polyphenols, the hydroxycinnamates, the flavanones, and the flavonols, respectively, was studied in an in vitro mixed culture model of the human colonic microflora. Time- and concentration-dependent degradation of all three compounds was observed, which was associated with the following metabolic events after cleavage of the ester or glycosidic bond: reduction of the aliphatic double bond of the resulting hydroxycinnamate caffeic acid residue; dehydroxylation and ring fission of the heterocyclic C-ring of the resulting deglycosylated flavanone, naringenin, and of the deglycosylated flavonol, quercetin (which differed depending on the substitution). The metabolic events, their sequences, and major phenolic end products, as identified by GC-MS or LC-MS/MS, were elucidated from the structural characteristics of the investigated compounds. The major phenolic end products identified were 3-D-hydroxyphenyl)propionic acid for chlorogenic acid, 3-(4-hydroxyphenyl)-propionic acid and 3-phenylpropionic acid for naringin, and 3-hydroxyphenylacetic acid and 3-(3-hydroxyphenyl)-propionic acid for rutin. The degree of degradation of the compounds studied was significantly influenced by the substrate concentration as well as individual variations in the composition of the fecal flora. The results support extensive metabolism of dietary polyphenols in the colon, depending on substrate concentration and residence time, with resultant formation of simple phenolics, which can be considered biomarkers of colonic metabolism if subsequently absorbed. It is also apparent that a relatively small number of phenolic degradation products are formed in the colon from the diverse group of natural polyphenols. (C) 2003 Elsevier Inc. All rights reserved.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Food and Nutritional Sciences
Interdisciplinary centres and themes > Institute for Cardiovascular and Metabolic Research (ICMR)
ID Code:13056
Uncontrolled Keywords:colonic metabolism, flavonoids, hydroxycinnamates, phenolic acids, free, radicals, HUMAN INTESTINAL BACTERIA, CAFFEIC ACID-DERIVATIVES, URINARY, METABOLITES, FLAVONOID GLYCOSIDES, MASS-SPECTROMETRY, HUMAN PLASMA, IN-VIVO, C-RING, HUMANS, QUERCETIN

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