Microbial transformation of 6-nitrobenzo(a)pyrene. [Cunninghamella elegans]
The fungal metabolism of the potent mutagenic and carcinogenic nitropolycyclic aromatic hydrocarbon (nitro-PAH) 6-nitrobenzo(a)pyrene (6-NO/sub 2/-BaP) was investigated. Cunninghamella elegans was incubated with 6-NO/sub 2/-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 /sup 1/H nuclear magnetic resonance spectra. The results of the study indicate that C. elegans metabolized 6-NO/sub 2/-BaP to glucoside and sulfate conjugates of 1- and 3-hydroxy 6-NO/sub 2/-BaP and suggests that glycosylation and sulfation reactions may represent detoxification pathways in the fungal metabolism of nitro-PAHs. Experiments using (G-/sup 3/H)-6-NO/sub 2/-BaP indicated that C. elegans metabolized 62% of 6-NO/sub 2/-BaP with 168 h. The 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-NO/sub 2/-BaP to biologically inactive compounds may have practical applications in the detoxification of nitro-PAH-contaminated wastes.
- Research Organization:
- National Center for Toxicological Research, Jefferson, AR
- OSTI ID:
- 7065460
- Journal Information:
- J. Toxicol. Environ. Health; (United States), Journal Name: J. Toxicol. Environ. Health; (United States) Vol. 19:4; ISSN JTEHD
- Country of Publication:
- United States
- Language:
- English
Similar Records
Oxidation of benzo(a)pyrene by the filamentous fungus Cunninghamella elegans
Metabolism of 1-, 3-, and 6-nitrobenzo(a)pyrene by intestinal microflora
Related Subjects
59 BASIC BIOLOGICAL SCIENCES
AROMATICS
BENZOPYRENE
BIODEGRADATION
BIOLOGICAL PATHWAYS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CONDENSED AROMATICS
DECOMPOSITION
DETOXIFICATION
FUNGI
HYDROCARBONS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
LIQUID COLUMN CHROMATOGRAPHY
MASS SPECTRA
METABOLISM
NITRO COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PLANTS
SEPARATION PROCESSES
SPECTRA
TRACER TECHNIQUES
TRITIUM COMPOUNDS
ULTRAVIOLET SPECTRA