Biotransformation of 1-nitrobenzo[e]pyrene by the fungus Cunninghamella elegans

Biotransformation of 1-nitrobenzo[e]pyrene (l-nitro-BeP), an environmental pollutant derived from the nitration of a non-carcinogen, benzo[e]pyrene, w as studied using the fungus Cunninghamella elegans ATCC 36112, After 72 h i ncubation, 89% of 1-nitro-[H-3]BeP added had been metabolized to two major metabolites. These metabolites were separated by reversed-phase high perfor mance liquid chromatography and identified by H-1 NMR, UV-visible, and mass spectral techniques as 1-nitro-6-benzo[e]pyrenylsulfate and 1-nitrobenzo[e ]pyrene 6-O-beta-glucopyranoside. Comparison of the fungal metabolism patte rns of 1-nitro-BeP and BeP indicates that the nitro group at the C-l positi on of BeP altered the regioselectivity of metabolism.