Two K-regions of 5-methylchrysene are sites of oxidative metabolism.
Two K-region trans-dihydrodiols were identified as products formed in the metabolism of 5-methylchrysene by liver microsomes from phenobarbital-treated male Sprague-Dawley rats. These two dihydrodiols were isolated from a mixture of metabolites by reversed-phase and normal-phase high-performance liquid chromatographies. Both K-region dihydrodiols were characterized by ultra-violet, mass, and circular dichroism spectral analyses. Chiral stationary phase high-performance liquid chromatographic analyses indicated that 5-methylchrysene 5,6-dihydrodiol and 11,12-dihydrodiol contain (S,S): (R,R) enantiomer ratios of 2:98 and 12:88, respectively. Although it is a bay-region dihydrodiol, the hydroxyl groups of 5-methylchrysene trans-5,6-dihydrodiol adopt a quasidiequatorial conformation.
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D002911:Chrysenes / Q000378:metabolism*; D002942:Circular Dichroism; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D010084:Oxidation-Reduction; D010616:Phenanthrenes / Q000378:metabolism*; D051381:Rats; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D002911:Chrysenes; D010616:Phenanthrenes; C008422:5-methylchrysene