linoleic-acid and 9-10-dihydro-9-10-dihydroxybenzo(a)pyrene

Metabolism of resolved radioactive stereoisomer, [14C](+)-benzo-(a)pyrene-trans-7,8-dihydrodiol by highly purified soybean lipoxygenase plus linoleic acid was investigated. Trans-anti-7,8,9,10-tetrahydrotetrol, the product of hydrolytic breakdown of ultimate mutagenic benzo(a)pyrene-anti-7,8-dihydrodiol,9,10-epoxide, was detected as a major metabolite. The epoxidation, depended on the enzyme concentration and was inhibited by nordihydroguaiaretic acid. This study provides evidence on the ability of lipoxygenase to catalyze the epoxidation of benzo(a)pyrene-7,8-dihydrodiol.

Topics: Chromatography, High Pressure Liquid; Dihydroxydihydrobenzopyrenes; Epoxy Compounds; Glycine max; Kinetics; Linoleic Acid; Linoleic Acids; Lipoxygenase; Plants