Catabolism of (+)-Catechin and (−)-Epicatechin by Rat Intestinal Microbiota

Catabolism of (+)-catechin (+C) and (−)-epicatechin (EC) by rat intestinal microbiota was examined in vitro. +C and EC metabolites isolated were identified by LC-MS and NMR analyses. As a result, 4-hydroxy-5-(3-hydroxyphenyl)­valeric acid (C-5 and EC-5), 4-oxo-5-(3,4-dihydorxyphenyl)­valeric acid (E...

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Veröffentlicht in:Journal of agricultural and food chemistry 2013-05, Vol.61 (20), p.4927-4935
Hauptverfasser: Takagaki, Akiko, Nanjo, Fumio
Format: Artikel
Sprache:eng
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Zusammenfassung:Catabolism of (+)-catechin (+C) and (−)-epicatechin (EC) by rat intestinal microbiota was examined in vitro. +C and EC metabolites isolated were identified by LC-MS and NMR analyses. As a result, 4-hydroxy-5-(3-hydroxyphenyl)­valeric acid (C-5 and EC-5), 4-oxo-5-(3,4-dihydorxyphenyl)­valeric acid (EC-7), 4-oxo-5-(3-hydorxyphenyl)­valeric acid (EC-8), and 1-(4-hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)­propan-2-ol (EC-13) were identified as new metabolites of +C or EC. From the measurement of optical rotation, each of the +C and EC metabolites possessing the same chemical structure and chiral carbon was inferred to have an enantiomeric relationship to each other and to maintain the configurations at the 3-position of the original catechins. On the basis of these findings together with previous information, the proposed metabolic pathway of +C and EC by rat intestinal microbiota was updated.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf304431v