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Microbial Transformation of 6-nitrobenzo[a]pyrene

Microbial Transformation of 6-nitrobenzo[a]pyrene

G C Millner, P P Fu, C E Cerniglia

J Toxicol Environ Health. 1986;19(4):519-30.

PMID: 3783769

Abstract:

The fungal metabolism of the potent mutagenic and carcinogenic nitropolycyclic aromatic hydrocarbon (nitro-PAH) 6-nitrobenzo[a]pyrene (6-NO2-BaP) was investigated. Cunninghamella elegans was incubated with 6-NO2-BaP for periods ranging between 1 and 7 d, and the metabolites formed were separated by high-performance liquid chromatography and identified by their UV-visible absorption, mass, and 1H nuclear magnetic resonance spectra. The results of our study indicate that C. elegans metabolized 6-NO2-BaP to glucoside and sulfate conjugates of 1- and 3-hydroxy 6-NO2-BaP and suggests that glycosylation and sulfation reactions may represent detoxification pathways in the fungal metabolism of nitro-PAHs. Experiments using [G3H]-6-NO2-BaP indicated that C. elegans metabolized 62% of 6-NO2-BaP within 168 h. Our data also indicated that the nitro group at the C-6 position of benzo[a]pyrene blocked metabolism at the regions peri to the nitro substituent (C-7, C-8 positions) and enhanced metabolism at the C-1 and C-3 positions. The ability of the fungus C. elegans to metabolize 6-NO2-BaP to biologically inactive compounds may have practical applications in the detoxification of nitro-PAH-contaminated wastes.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP63041907	6-Nitrobenzo[a]pyrene		63041-90-7	Price

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