Metabolism of 7-methylbenz[a]anthracene and 7-hydroxymethylbenz[a]anthracene by Cunninghamella elegans.
The fungal metabolism of 7-methylbenz[a]anthracene (7-MBA) and 7-hydroxymethylbenz[a]anthracene (7-OHMBA) was studied. 7-MBA was metabolized by Cunninghamella elegans to form 7-OHMBA-trans-8,9-dihydrodiol and 7-OHMBA-trans-3,4-dihydrodiol as the predominant metabolites. Other metabolites were identified as 7-OHMBA, 7-MBA-trans-8,9-dihydrodiol and 7-MBA-trans-3,4-dihydrodiol, and 7-MBA-8,9,10,11-tetraol. Incubation of 7-OHMBA with C. elegans cells indicated that 7-OHMBA-trans-8,9-dihydrodiol and 7-OHMBA-trans-3,4-dihydrodiol were major metabolites. The metabolism of 7-MBA by rat liver microsomes from 3-methylcholanthrene-treated rats showed that the metabolites were qualitatively similar to those formed by C. elegans, except additional dihydrodiol metabolites were formed at the 5,6 and 10,11 positions. The metabolites formed were isolated by high-performance liquid chromatography and identified by comparing their chromatographic, UV-visible absorption and mass spectral properties with those of reference compounds.
D000818:Animals; D001551:Benz(a)Anthracenes / Q000378:metabolism*; D055598:Chemical Phenomena; D002621:Chemistry; D008862:Microsomes, Liver / Q000378:metabolism; D009090:Mucorales / Q000378:metabolism*; D010084:Oxidation-Reduction; D051381:Rats
D001551:Benz(a)Anthracenes; C035844:7-hydroxymethylbenz(a)anthracene-8,9-dihydrodiol; C025909:7-hydroxymethylbenz(a)anthracene; C035845:7-hydroxymethylbenz(a)anthracene-3,4-dihydrodiol; C021219:7-methylbenzanthracene