Identification of glyceollin metabolites derived from conjugation with glutathione and glucuronic acid in male ZDSD rats by online liquid chromatography-electrospray ionization tandem mass spectrometry

Syeda S. Quadri, Robert Stratford Jr., Stephen M. Boué, Richard B. Cole

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Glyceollin-related metabolites produced in rats following oral glyceollin administration were screened in plasma, feces, and urine, and these metabolites were identified by precursor and product ion scanning using liquid chromatography coupled online with electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS). Precursor ion scanning in the negative ion (NI) mode was used to identify all glyceollin metabolites based on production of a diagnostic radical product ion (m/z 148) upon decomposition. Using this approach, precursor peaks of interest were found at m/z 474 and 531. Tandem mass spectra of these two peaks allowed us to characterize them as byproducts of glutathione conjugation. The peak at m/z 474 was identified as the deprotonated cysteinyl conjugate of glyceollins with an addition of an oxygen atom, whereas m/z 531 was identified as the deprotonated cysteinylglyceine glyceollin conjugate plus an oxygen. These results were confirmed by positive ion (PI) mode analyses. Mercapturic acid conjugates of glyceollins were also identified in NI mode. In addition, glucuronidation of glyceollins was observed, giving a peak at m/z 513 corresponding to the deprotonated conjugate. Production of glucuronic acid conjugates of glyceollins was confirmed in vitro in rat liver microsomes. Neither glutathione conjugation byproducts nor glucuronic acid conjugates of glyceollins have been previously reported.

Original languageEnglish (US)
Pages (from-to)2692-2700
Number of pages9
JournalJournal of Agricultural and Food Chemistry
Volume62
Issue number12
DOIs
StatePublished - Mar 26 2014
Externally publishedYes

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Electrospray ionization
Glucuronic Acid
glucuronic acid
Electrospray Ionization Mass Spectrometry
Liquid chromatography
Metabolites
Tandem Mass Spectrometry
Liquid Chromatography
liquid chromatography
Mass spectrometry
Glutathione
Rats
glutathione
ions
metabolites
rats
Ions
byproducts
oxygen
liver microsomes

Keywords

  • phase I metabolism
  • phase II metabolism
  • phytoalexins
  • phytochemicals
  • phytoestrogens
  • reactive oxygen species

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Cite this

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title = "Identification of glyceollin metabolites derived from conjugation with glutathione and glucuronic acid in male ZDSD rats by online liquid chromatography-electrospray ionization tandem mass spectrometry",
abstract = "Glyceollin-related metabolites produced in rats following oral glyceollin administration were screened in plasma, feces, and urine, and these metabolites were identified by precursor and product ion scanning using liquid chromatography coupled online with electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS). Precursor ion scanning in the negative ion (NI) mode was used to identify all glyceollin metabolites based on production of a diagnostic radical product ion (m/z 148) upon decomposition. Using this approach, precursor peaks of interest were found at m/z 474 and 531. Tandem mass spectra of these two peaks allowed us to characterize them as byproducts of glutathione conjugation. The peak at m/z 474 was identified as the deprotonated cysteinyl conjugate of glyceollins with an addition of an oxygen atom, whereas m/z 531 was identified as the deprotonated cysteinylglyceine glyceollin conjugate plus an oxygen. These results were confirmed by positive ion (PI) mode analyses. Mercapturic acid conjugates of glyceollins were also identified in NI mode. In addition, glucuronidation of glyceollins was observed, giving a peak at m/z 513 corresponding to the deprotonated conjugate. Production of glucuronic acid conjugates of glyceollins was confirmed in vitro in rat liver microsomes. Neither glutathione conjugation byproducts nor glucuronic acid conjugates of glyceollins have been previously reported.",
keywords = "phase I metabolism, phase II metabolism, phytoalexins, phytochemicals, phytoestrogens, reactive oxygen species",
author = "Quadri, {Syeda S.} and {Stratford Jr.}, Robert and Bou{\'e}, {Stephen M.} and Cole, {Richard B.}",
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T1 - Identification of glyceollin metabolites derived from conjugation with glutathione and glucuronic acid in male ZDSD rats by online liquid chromatography-electrospray ionization tandem mass spectrometry

AU - Quadri, Syeda S.

AU - Stratford Jr., Robert

AU - Boué, Stephen M.

AU - Cole, Richard B.

PY - 2014/3/26

Y1 - 2014/3/26

N2 - Glyceollin-related metabolites produced in rats following oral glyceollin administration were screened in plasma, feces, and urine, and these metabolites were identified by precursor and product ion scanning using liquid chromatography coupled online with electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS). Precursor ion scanning in the negative ion (NI) mode was used to identify all glyceollin metabolites based on production of a diagnostic radical product ion (m/z 148) upon decomposition. Using this approach, precursor peaks of interest were found at m/z 474 and 531. Tandem mass spectra of these two peaks allowed us to characterize them as byproducts of glutathione conjugation. The peak at m/z 474 was identified as the deprotonated cysteinyl conjugate of glyceollins with an addition of an oxygen atom, whereas m/z 531 was identified as the deprotonated cysteinylglyceine glyceollin conjugate plus an oxygen. These results were confirmed by positive ion (PI) mode analyses. Mercapturic acid conjugates of glyceollins were also identified in NI mode. In addition, glucuronidation of glyceollins was observed, giving a peak at m/z 513 corresponding to the deprotonated conjugate. Production of glucuronic acid conjugates of glyceollins was confirmed in vitro in rat liver microsomes. Neither glutathione conjugation byproducts nor glucuronic acid conjugates of glyceollins have been previously reported.

AB - Glyceollin-related metabolites produced in rats following oral glyceollin administration were screened in plasma, feces, and urine, and these metabolites were identified by precursor and product ion scanning using liquid chromatography coupled online with electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS). Precursor ion scanning in the negative ion (NI) mode was used to identify all glyceollin metabolites based on production of a diagnostic radical product ion (m/z 148) upon decomposition. Using this approach, precursor peaks of interest were found at m/z 474 and 531. Tandem mass spectra of these two peaks allowed us to characterize them as byproducts of glutathione conjugation. The peak at m/z 474 was identified as the deprotonated cysteinyl conjugate of glyceollins with an addition of an oxygen atom, whereas m/z 531 was identified as the deprotonated cysteinylglyceine glyceollin conjugate plus an oxygen. These results were confirmed by positive ion (PI) mode analyses. Mercapturic acid conjugates of glyceollins were also identified in NI mode. In addition, glucuronidation of glyceollins was observed, giving a peak at m/z 513 corresponding to the deprotonated conjugate. Production of glucuronic acid conjugates of glyceollins was confirmed in vitro in rat liver microsomes. Neither glutathione conjugation byproducts nor glucuronic acid conjugates of glyceollins have been previously reported.

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KW - phytoestrogens

KW - reactive oxygen species

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