Mass spectrometric methods for the analysis of chlorinated and nitrated isoflavonoids: a novel class of biological metabolites

JK Prasain, R Patel, M Kirk, L Wilson, Nigel Peter Botting, VM Darley-Usmar, S Barnes

Research output: Other contribution

26 Citations (Scopus)

Abstract

Electrospray ionization combined with tandem mass spectrometry was applied to a study of some representative chlorinated and nitrated isoflavones-potential metabolites of isoflavones in inflammatory cells. Upon collision-induced dissociation of deprotonated [M - H](-) ions of these compounds, a number of structurally characteristic product ions were produced. The product ion analysis of 3'- and 8-chlorodaidzein in the tandom mass spectra led to ready differentiation of these isomers. 3-Nitro derivatives of both genistein and daidzein have product ions due to the losses of HNO2 and two OH groups. Chlorinated derivatives of isoflavones were detected in cell-based experiments and their structures were proposed by comparing the tandem mass spectra of their product ions with those of standards. This work provides a suitable analytical basis to aid the characterization of chlorinated and nitrated metabolites in studies in vivo and in vitro. Copyright (C) 2003 John Wiley Sons, Ltd.

Original languageEnglish
Volume38
DOIs
Publication statusPublished - Jul 2003

Keywords

  • electrospray ionization
  • tandem mass spectrometry
  • chlorinated isoflavones
  • nitration
  • identification
  • NITRIC-OXIDE
  • IN-VITRO
  • LIPOPROTEIN OXIDATION
  • INFLAMMATORY OXIDANTS
  • ESTROGEN-RECEPTORS
  • HYPOCHLOROUS ACID
  • HUMAN NEUTROPHILS
  • SOY
  • MYELOPEROXIDASE
  • GENISTEIN

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