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

Biotransformation of 1-nitrobenzo[e]pyrene (1-nitro-BeP) an environmental pollutant derived from the nitration of non-carcinogen, benzo[e]pyrene was studied using the fungus Cunninghamella elegans ATCC 36112. After 72 incubation, 89% of 1-nitro-[3H]BeP added had been metabolized to two major metabolites. These metabolites were separated by reversed-phase high performance liquid chromatography and identified by 1H 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 patterns of 1-nitro-BeP and BeP indicates that the nitro group at the C-1 position of BeP altered the regioselectivity of metabolism.