Metabolism of benz[a]anthracene by the filamentous fungus Cunninghamella elegans.
The metabolism of the carcinogen benz[a]anthracene (BA), a tetracyclic aromatic hydrocarbon, by Cunninghamella elegans was investigated. C. elegans grown on Sabouraud dextrose broth transformed [14C]BA to labeled BA trans-8,9-dihydrodiol (90%), BA trans-10,11-dihydrodiol (6%), and BA trans-3,4-dihydrodiol (4%), but not to BA trans-5,6-dihydrodiol. These metabolites were separated by thin-layer chromatography and reversed-phase high-performance liquid chromatography and were identified by UV and mass spectral techniques. A BA tetraol, 8 beta,9 alpha,10 alpha,11 beta-tetrahydroxy-8 alpha, 9 beta,10 beta,11 alpha-tetrahydro-BA, was also identified as a metabolite and may have arisen as an additional oxidation product of either BA 8,9- or 10,11-dihydrodiol. This is the first study in which a biologically produced BA tetraol has been identified. Our results suggest that the transformation of BA to trans-dihydrodiols by C. elegans is similar to the transformation of BA found in mammals, except that BA 5,6-dihydrodiol is not produced.
Cerniglia
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Microbiology Division, Food and Drug Administration, Jefferson, Arkansas 72079.
Gibson
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Dodge
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D001551:Benz(a)Anthracenes / Q000302:isolation & purification* / Q000378:metabolism*; D009090:Mucorales / Q000378:metabolism*; D013997:Time Factors
D001551:Benz(a)Anthracenes; C021626:benzanthracene-8,9-dihydrodiol; C015149:benzanthracene-3,4-dihydrodiol; C021627:benzanthracene-10,11-dihydrodiol