Fungal oxidation of (+-)-9,10-dihydroxy-9,10-dihydrobenzo(a)pyrene: formation of diastereomeric benzo(a)pyrene 9,10-diol 7,8-epoxides

Journal Article · Fri Aug 01 00:00:00 EDT 1980 · Proc. Natl. Acad. Sci. U.S.A.; (United States)

DOI:https://doi.org/10.1073/pnas.77.8.4554· OSTI ID:6850410

Cerniglia, C E; Gibson, D T

The filamentous fungus Cunninghamella elegans oxidized (+-) trans-9,10-dihydroxy-9,10-dihydrobenzo(a)-pyrene to a complex mixture of metabolites which were detected by high-pressure liquid chromatography. Two of the metabolites were identified as (+-)-7..beta..,8..cap alpha..,9..cap alpha..,10..beta..-tetrahydroxy-7,8,9,10-tetrahydrobenzo(a)pyrene and (+-)-7..beta..,8..cap alpha..,9..cap alpha..,10..cap alpha..-tetrahydroxy-7,8,9,10-tetrahydrobenzo(a)pyrene. A third product gave absorption and mass spectra consistent with a diol-epoxide structure. Hydrolysis of this compound gave (+-)-7..beta..,8..cap alpha..,9..beta..,10..cap alpha..-tetrahydroxy-7,8,9,10-tetrahydrobenzo(a)pyrene as the major identifiable product with a minor unidentified tetraol. Synthetic (+-)-9..cap alpha..,10..beta..-dihydroxy-7..beta..,8..beta..-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene gave the same hydrolysis products and had the same retention time on high-pressure liquid chromatography as did the fungal metabolite. The trans-9,10-dihydroxy-9,10-dihydrobenzo(a)pyrene recovered at the end of the experiment showed no optical activity, indicating that both enantiomers were metabolized by the fungus. The results suggest that C. elegans oxidized (+-)-trans-9,10-dihydroxy-9,10-dihydrobenzo(a)pyrene to diastereomeric benzo(a)pyrene 9,10-diol 7,8-epoxides.

• Research Organization: Univ. of Texas, Austin
• OSTI ID: 6850410
• Journal Information: Proc. Natl. Acad. Sci. U.S.A.; (United States), Journal Name: Proc. Natl. Acad. Sci. U.S.A.; (United States) Vol. 77:8; ISSN PNASA
• Country of Publication: United States
• Language: English

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59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ABSORPTION SPECTRA
ALCOHOLS
AROMATICS
BENZOPYRENE
BIOCHEMISTRY
CHEMICAL REACTIONS
CHEMISTRY
CONDENSED AROMATICS
DECOMPOSITION
ENANTIOMORPHS
EPOXIDES
FUNGI
GLYCOLS
HYDROCARBONS
HYDROLYSIS
HYDROXY COMPOUNDS
LYSIS
METABOLISM
METABOLITES
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIDATION
PLANTS
SOLVOLYSIS
SPECTRA