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

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...

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Published in:Journal of mass spectrometry. 2003-07, Vol.38 (7), p.764-771
Main Authors: Prasain, Jeevan K., Patel, Rakesh, Kirk, Marion, Wilson, Landon, Botting, Nigel, Darley-Usmar, Victor M., Barnes, Stephen
Format: Article
Language:English
Subjects:
Biological and medical sciences
chlorinated isoflavones
Chlorine - chemistry
Chlorine - metabolism
electrospray ionization
General pharmacology
Genistein - analysis
Genistein - metabolism
HL-60 Cells
Humans
identification
Isoflavones - analysis
Isoflavones - chemistry
Isoflavones - metabolism
Medical sciences
Nitrates - chemistry
Nitrates - metabolism
nitration
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Spectrometry, Mass, Electrospray Ionization - methods
tandem mass spectrometry
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Summary: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 © 2003 John Wiley & Sons, Ltd.
ISSN:1076-5174
1096-9888
DOI:10.1002/jms.492