Metabolic conversion of dibenz[a,h]anthracene (+/-)trans-1,2-dihydrodiol and chrysene (+/-)trans-3,4-dihydrodiol to vicinal dihydrodiol epoxides.
The hydroxyl groups of dibenz[a,h]anthracene trans-1,2-dihydrodiol and chrysene trans-3,4-dihydrodiol are known to be predominantly in quasi-axial conformations. These dihydrodiols were metabolized by liver microsomes from 3-methylcholanthrene-pretreated rats to form 1,2,3,4-tetrahydrotetrols as the major products. The major metabolites of the dihydrodiols were isolated by reversed-phase high-performance liquid chromatography and identified by ultraviolet--visible absorption and mass spectral analyses. The results indicate that axial hydroxyl groups of dibenz[a,h]anthracene trans-1,2-dihydrodiol and of chrysene trans-3,4-dihydrodiol do not direct metabolism away from their respective vicinal double bond.
D000818:Animals; D001551:Benz(a)Anthracenes / Q000378:metabolism*; D001711:Biotransformation; D002474:Cell-Free System; D002851:Chromatography, High Pressure Liquid; D002911:Chrysenes / Q000378:metabolism*; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D010616:Phenanthrenes / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains; D013056:Spectrophotometry, Ultraviolet
D001551:Benz(a)Anthracenes; D002911:Chrysenes; D010616:Phenanthrenes; C018911:dibenzoanthracene-1,2-dihydrodiol; C021646:chrysene-3,4-dihydrodiol