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Fungal oxidation of benzo(a)pyrene and (+-)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene

Journal Article · · J. Biol. Chem.; (United States)
OSTI ID:5098774
;

The oxidation of benzo(a)pyrene by intact cells of the filamentous fungus Cunninghamella elegans resulted in the formation of a complex mixture of polar products which were detected by high pressure liquid chromatography. One of the products had a retention time on high pressure liquid chromatography identical with that given by (+-)-7..beta..,8a,9a,10..beta..-tetrahydroxy-7,8,9,10-tetrahydrobenzo(a)pyrene. In addition the absorption and mass spectra given by the fungal metabolite were consistent with this structural assignment. Incubation of (+-)-trans-7,8-dihydrobenzo(a)pyrene with cells of C. elegans led to the formation of the same tetrahydroxymetabolite. Two other products were formed that were identified as new phenolic derivatives of (+-)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene. Experiments with (+-)-trans (G-/sup 3/H) 7,8-dihydrobenzo(a)pyrene showed that over a 12-h period 4.0% of the dihydrodiol was converted to ethyl acetate-soluble products and 7..beta..,8..cap alpha..,9..cap alpha..,10..beta..-tetrahydroxy-7,8,9,10-tetrahdrobenzo(a)pyrene accounted for 25% of these metabolites. The results suggest that C. elegans can oxidize benzo(a)pyrene to either (+-)-7..beta..,8..cap alpha..-dihydroxy-9..cap alpha..,10..cap alpha..-epoxy-7,8,9,10-tetrahydroxy(a)pyrene or one of the two possible enantiomers of this compound. Under the experimental conditions, no evidence was found to suggest the formation of (+-)-7..beta..,8..cap alpha..-dihydroxy-9..beta..,10..beta..-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene. Thus, C. elegans has the ability to form at least one of the two diastereomeric benzo(a)pyrene 7,8-diol-9,10-epoxides that have been implicated as the ultimate carcinogenic forms of benzo(a)pyrene in higher organisms.

Research Organization:
Univ. of Texas, Austin
OSTI ID:
5098774
Journal Information:
J. Biol. Chem.; (United States), Journal Name: J. Biol. Chem.; (United States) Vol. 255:11; ISSN JBCHA
Country of Publication:
United States
Language:
English

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Related Subjects

550200 -- Biochemistry
550700 -- Microbiology
560302* -- Chemicals Metabolism & Toxicology-- Microorganisms-- (-1987)
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
BENZOPYRENE
BIOCHEMICAL REACTION KINETICS
CHEMICAL ANALYSIS
CHEMICAL REACTIONS
CONDENSED AROMATICS
EPOXIDES
FUNGI
HYDROCARBONS
KINETICS
METABOLISM
METABOLITES
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIDATION
PLANTS
QUALITATIVE CHEMICAL ANALYSIS
REACTION KINETICS