Article Abstract:
The metabolites produced by Cunninghamella elegans from fluorethane (FA) were tested for mutagenicity by the Salmonella typhimurium reversion assay. Results showed that the overall effect of incubating FA with C. elegans was the reduce mutagenicity. Positive mutagenic responses occured only in the presence of rat liver microsomes. These microsomal fractions convert FA to the more mutagenic trans-2,3,-dihydrodiol. However, fungal dihydrodiols were only weakly mutagenic. Stereochemical analysis showed that the fungi produced both enantiomers of trans-2,3,-dihydrodiol, with no optical activity. The microsomal dihydrodiol was optically active.
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Article Abstract:
The stereoselectivity of trans-dihydrodiols produced from phenanthrene by Cunninghamella elegans, Syncephalastrum racemosum and Phanerochaete chrysosporium were investigated by circular dichroism spectroscopy and chiral stationary-phase high-performance liquid chromatography. The results showed that C. elegans produced both enantiomers of trans-1,2-dihydrodiol, P. chrysosporium produced the 3R,4R enantiomer of trans-3,4-dihydrodiol and S. racemosum produced both enantiomers. These results demonstrate interspecies variability in the regio- and stereoselectivity of enzymes involved in phenanthrene metabolism.
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Article Abstract:
The white rot fungus Pleurotus ostreatus metabolizes 94% of the added polycyclic aromatic hydrocarbon phenanthrene to form phenanthrene trans-9,10-dihydrodiol, and small amounts of CO2 and 2,2'-diphenic acid. The stereoselective oxidation of phenanthrene by cytochrome P-450 monooxygenase, followed by epoxide hydrolase-mediated hydration, forms the dihydrodiol. The dihydrodiol is the main metabolic product and is mainly present as the 9R,10R enantiomere. The metabolism is suppressed by P-450 inhibitors such as SKF 525-A and fluoxetine.
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