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Structural identification of novel glucoside and glucuronide metabolites of (−)‐epigallocatechin‐3‐gallate in mouse urine using liquid chromatography/electrospray ionization tandem mass spectrometry
Author(s) -
Sang Shengmin,
Yang Chung S.
Publication year - 2008
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.3786
Subject(s) - chemistry , metabolite , chromatography , electrospray ionization , tandem mass spectrometry , polyphenol , mass spectrometry , liquid chromatography–mass spectrometry , metabolomics , epigallocatechin gallate , glucuronide , gallate , glucoside , electrospray , catechin , biochemistry , antioxidant , medicine , alternative medicine , pathology , nuclear chemistry
(−)‐Epigallocatechin‐3‐gallate (EGCG), the most abundant and most biologically active polyphenolic compound in tea, has been proposed to have many health beneficial effects. The metabolic fate of EGCG, however, is not well understood. In the present study, we identified a novel EGCG metabolite, 7‐ O ‐ β ‐D‐glucopyranosyl‐EGCG‐4″‐ O ‐ β ‐D‐glucupyranoside, in a mouse urine sample using liquid chromatography/electrospray ionization tandem mass spectrometry. The structure of this metabolite was confirmed by analyzing the MS n (n = 1–4) spectra as well as comparing the MS/MS spectra of its product ions with those from EGCG and EGCG‐4″‐ O ‐ β ‐D‐glucupyranoside standards. To our knowledge, this is the first report of the identification of a glucoside metabolite of EGCG in mammals. Our results indicate that glucosidation represents a novel pathway in the metabolism of EGCG in mice. Copyright © 2008 John Wiley & Sons, Ltd.