Abstract
Benz[a]anthracene is metabolized to 5,6-dihydro-5,6-dihydroxybenz[a]anthracene and 8,9-dihydro-8,9-dihydroxybenz[a]anthracene by the microsomal fraction of ratliver and NADPH and these metabolites are formed at similar rates. When the soluble liver fraction and GSH are also present, the rate of formation of the 8,9-dihydrodiol is not affected while that of the 5,6-isomer is considerably reduced. Since epoxides are the intermediates formed in the metabolism of aromatic hydrocarbons, the further metabolism of benz[a]anthracene 5,6- and 8,9-oxide into dihydrodiols and into GSH conjugates has been investigated. Each epoxide is converted into a dihydrodiol by microsomal “epoxide hydrase” at a similar rate, whereas conjugation with GSH. a reaction catalysed by “glutathione S-epoxide transferase” in the soluble liver fraction, proceeds considerably more rapidly with the 5,6- than with the 8,9-isomer. When a mixture of the two epoxides of benz[a]anthracene is incubated both with “epoxide hydrase” and with “GSH transferase”, the 5,6-isomer is converted largely into the GSH conjugate while the main route of metabolism of the 8,9-isomer is by hydration to the dihydrodiol.
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