Reactions of Genistein with alkylperoxyl radicals.
Antioxidant actions of the soy isoflavone genistein are believed to contribute to its overall chemopreventive activity. However, the mechanisms of its antioxidant reactions remain unknown. The objective of this study was to characterize the reaction products of genistein (5,7,4'-trihydroxyisoflavone) with peroxyl radicals generated by thermolysis of 2,2'-azobis(2,4-dimethylvaleronitrile) (AMVN). Genistein oxidations with AMVN-derived peroxyl radicals yielded orobol (5,7,3',4'-tetrahydroxyisoflavone), a hydroxylated derivative of genistein, and several stable adducts of 4'-oxogenistein with AMVN-derived radicals. Some of these adducts include novel structures resulting from secondary oxidations of the AMVN-derived moiety. For all the observed oxidation products, the modifications occurred on the B-ring of the molecule. Genistein oxidation product structures provide potentially useful markers of genistein antioxidant chemistry.
Arora
A
A
Department of Pharmacology and Toxicology and Southwest Environmental Health Sciences Center, College of Pharmacy, The University of Arizona, Tucson 85721, USA.
Valcic
S
S
Cornejo
S
S
Nair
M G
MG
Timmermann
B N
BN
Liebler
D C
DC
D000097:Acetonitriles / Q000737:chemistry; D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism; D001391:Azo Compounds / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005609:Free Radicals / Q000737:chemistry; D019833:Genistein / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D009570:Nitriles / Q000737:chemistry; D010084:Oxidation-Reduction; D010103:Oxygen Isotopes; D010545:Peroxides / Q000737:chemistry*
D000097:Acetonitriles; D000975:Antioxidants; D001391:Azo Compounds; D005609:Free Radicals; D009570:Nitriles; D010103:Oxygen Isotopes; D010545:Peroxides; C055792:2,2'-azobis(2,4-dimethylvaleronitrile); C049375:perhydroxyl radical; D019833:Genistein; C032159:acetonitrile