Structural identification of novel glucoside and glucuronide metabolites of (-)-epigallocatechin-3-gallate in mouse urine using liquid chromatography/ electrospray ionization tandem mass spectrometry

Shengmin Sang, Chung Yang

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

(-)-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 MSn (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.

Original languageEnglish (US)
Pages (from-to)3693-3699
Number of pages7
JournalRapid Communications in Mass Spectrometry
Volume22
Issue number22
DOIs
StatePublished - Nov 30 2008

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Electrospray ionization
Glucuronides
Liquid chromatography
Glucosides
Metabolites
Mass spectrometry
Polyphenolic compounds
Mammals
epigallocatechin gallate
Metabolism
Health
Ions

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry

Cite this

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title = "Structural identification of novel glucoside and glucuronide metabolites of (-)-epigallocatechin-3-gallate in mouse urine using liquid chromatography/ electrospray ionization tandem mass spectrometry",
abstract = "(-)-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 MSn (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.",
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N2 - (-)-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 MSn (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.

AB - (-)-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 MSn (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.

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