Catabolism of (+)-catechin and (-)-epicatechin by rat intestinal microbiota

J Agric Food Chem. 2013 May 22;61(20):4927-35. doi: 10.1021/jf304431v. Epub 2013 May 10.

Abstract

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.

MeSH terms

  • Animals
  • Catechin / chemistry
  • Catechin / metabolism*
  • Chromatography, High Pressure Liquid
  • Feces / microbiology
  • Intestines / microbiology*
  • Lactones / chemistry
  • Lactones / metabolism
  • Magnetic Resonance Spectroscopy
  • Male
  • Microbiota / physiology*
  • Molecular Conformation
  • Pentanoic Acids / chemistry
  • Pentanoic Acids / metabolism
  • Rats
  • Rats, Wistar
  • Stereoisomerism

Substances

  • Lactones
  • Pentanoic Acids
  • Catechin
  • n-pentanoic acid