Metabolic conversion of dibenz(a,h)anthracene (+/-)trans-1,2-dihydrodiol and chrysene (+/-)trans-3,4-dihydrodiol to vicinal dihydrodiol epoxides

Journal Article · Wed Jul 01 04:00:00 EDT 1981 · Proc. Natl. Acad. Sci. U.S.A.; (United States)

DOI:https://doi.org/10.1073/pnas.78.7.4270· OSTI ID:6078894

Chou, M W ^[1]; Fu, P P; Yang, S K

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1. Uniformed Services University of the Health Sciences, Bethesda, MD

The hydroxyl groups of dibenz(z,h)anthracene trans-1,2-dihydrodiol and chrysene trans-3,4-dihydrodiol are known to be predominantly in quasi-axial conformations. These dihydrodiols were metabolized by liver microsomes from 3-methylcholanthrene-pretreated rats to form 1,2,3,4-tetrahydrotetrols as the major products. The major metabolites of the dihydrodiols were isolated by reversed-phase high-performance liquid chromatography and identified by ultraviolet-visible absorption and mass spectral analyses. The results indicate that axial hydroxyl groups of dibenz(a,h)anthracene trans-1,2-dihydrodiol and of chrysene trans-3,4-dihydrodiol do not direct metabolism away from their respective vicinal double bond.

• OSTI ID: 6078894
• Journal Information: Proc. Natl. Acad. Sci. U.S.A.; (United States), Journal Name: Proc. Natl. Acad. Sci. U.S.A.; (United States) Vol. 78:7; ISSN PNASA
• Country of Publication: United States
• Language: English

Related Subjects

550900* -- Pathology
59 BASIC BIOLOGICAL SCIENCES
ALCOHOLS
ANIMALS
ANTHRACENE
AROMATICS
BODY
CARCINOGENESIS
CARCINOGENS
CELL CONSTITUENTS
CHROMATOGRAPHY
CHRYSENE
CONDENSED AROMATICS
DIGESTIVE SYSTEM
EPOXIDES
GLANDS
GLYCOLS
HYDROCARBONS
HYDROXY COMPOUNDS
LIQUID COLUMN CHROMATOGRAPHY
LIVER
MAMMALS
MASS SPECTRA
MASS SPECTROSCOPY
METABOLISM
METABOLITES
MICROSOMES
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANOIDS
ORGANS
PATHOGENESIS
RATS
RODENTS
SEPARATION PROCESSES
SPECTRA
SPECTROPHOTOMETRY
SPECTROSCOPY
VERTEBRATES