Glyceollins are isoflavones produced by soybeans under stressed conditions. Benefits of glyceollins include their anti-diabetic, glucose homeostasis, and therapeutic properties for breast, ovarian, and prostate cancers. However, the metabolism of glyceollins is not well understood. In this study, a method is developed for screening glyceollins and their metabolites based upon precursor ion scanning using a triple quadrupole mass spectrometer. Under higher-energy collisions, deprotonated glyceollin precursors yield a diagnostic radical product ion at m/z 148. We propose this resonance-stabilized radical anion, formed in violation of the even-electron rule, to be diagnostic of glyceollins and glyceollin metabolites. Precursor ion scans of m/z 148 from plasma originating from rats dosed with glyceollins produced peaks at m/z 337, 417, and 433. The peak at m/z 337 corresponds to deprotonated glyceollins, whereas m/z 417 and 433 were confirmed by accurate mass measurement to be sulfated metabolites of glyceollins with the latter having an additional oxygen.

Screening and identification of glyceollins and their metabolites by electrospray ionization tandem mass spectrometry with precursor ion scanning

245th National Meeting (2013)

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