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

Academic Article

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 HNO(2) 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.
  • Published In

    Keywords

  • Chlorine, Genistein, HL-60 Cells, Humans, Isoflavones, Nitrates, Spectrometry, Mass, Electrospray Ionization
  • Digital Object Identifier (doi)

    Author List

  • Prasain JK; Patel R; Kirk M; Wilson L; Botting N; Darley-Usmar VM; Barnes S
  • Start Page

  • 764
  • End Page

  • 771
  • Volume

  • 38
  • Issue

  • 7