Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans

Journal Article · Sat Dec 31 23:00:00 EST 1983 · Appl. Environ. Microbiol.; (United States)

OSTI ID:6980199

Cerniglia, C E; Yang, S K

The fungus Cunninghamella elegans oxidized anthracene and phenanthrene to form predominately transdihydrodiols. The metabolites were isolated by reversed-phase high-pressure liquid chromatography for structural and conformational analyses. Comparison of the circular dichroism spectrum of the fungal trans-1,2-dihydroxy-1,2-dihydroanthracene to that formed by rat liver microsomes indicated that the major enantiomer of the trans-1,2-dihydroxy-1,2-dihydroanthracene formed by C. elegans had an S,S absolute stereochemistry, which is opposite to the predominately 1R,2R dihydrodiol formed by rat liver microsomes. C. elegans oxidized phenanthrene primarily in the 1,2-positions to form trans-1,2-dihydroxy-1,2-dihydrophenanthrene. In addition, a minor amount of trans-3,4-dihydroxy-3,4-dihydrophenanthrene was detected. Metabolism at the K-region (9,10-positions) of phenanthrene was not detected. Comparison of the circular dichroism spectra of the phenanthrene trans-1,2- and trans-3,4-dihydrodiols formed by C. elegans to those formed by mammalian enzymes indicated that each of the dihydrodiols formed by C. elegans had an S,S absolute configuration. The results indicate that there are differences in both the regio- and stereoselective metabolism of anthracene and phenanthrene between the fungus C. elegans and rat liver microsomes. 26 references.

• Research Organization: Food and Drug Administration, Jefferson, AR
• OSTI ID: 6980199
• Journal Information: Appl. Environ. Microbiol.; (United States), Journal Name: Appl. Environ. Microbiol.; (United States) Vol. 47:1; ISSN AEMID
• Country of Publication: United States
• Language: English

Related Subjects

560302* -- Chemicals Metabolism & Toxicology-- Microorganisms-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ALCOHOLS
ANIMALS
ANTHRACENE
AROMATICS
BIOLOGICAL MODELS
BIOSYNTHESIS
CELL CONSTITUENTS
CHROMATOGRAPHY
COMPARATIVE EVALUATIONS
CONDENSED AROMATICS
FUNGI
GLYCOLS
HYDROCARBONS
HYDROXY COMPOUNDS
LIQUID COLUMN CHROMATOGRAPHY
MAMMALS
METABOLISM
MICROSOMES
MOLECULAR STRUCTURE
OPTICAL PROPERTIES
ORGANIC COMPOUNDS
ORGANOIDS
PHENANTHRENE
PHYSICAL PROPERTIES
PLANTS
RATS
RODENTS
SEPARATION PROCESSES
STEREOCHEMISTRY
SYNTHESIS
VERTEBRATES