Stereoselective fungal metabolism of methylated anthracenes
| Autor: | Warren L. Campbell, Carl E. Cerniglia, Peter P. Fu, James P. Freeman, Frederick E. Evans |
|---|---|
| Rok vydání: | 1990 |
| Předmět: |
Circular dichroism
Magnetic Resonance Spectroscopy Stereochemistry Stereoisomerism In Vitro Techniques Methylation Applied Microbiology and Biotechnology Hydroxylation chemistry.chemical_compound Animals Hydroxymethyl Enantiomeric excess Anthracenes Cunninghamella elegans Ecology biology Circular Dichroism Absolute configuration biology.organism_classification Rats chemistry Microsomes Liver Mucorales Enantiomer Research Article Food Science Biotechnology |
| Zdroj: | Applied and Environmental Microbiology. 56:661-668 |
| ISSN: | 1098-5336 0099-2240 |
| DOI: | 10.1128/aem.56.3.661-668.1990 |
| Popis: | The metabolism of 9-methylanthracene (9-MA), 9-hydroxymethylanthracene (9-OHMA), and 9,10-dimethylanthracene (9,10-DMA) by the fungus Cunninghamella elegans ATCC 36112 is described. The metabolites were isolated by high-performance liquid chromatography and characterized by UV-visible, mass, and 1H nuclear magnetic resonance spectral techniques. The compounds 9-MA and 9,10-DMA were metabolized by two pathways, one involving initial hydroxylation of the methyl group(s) and the other involving epoxidation of the 1,2- and 3,4- aromatic double bond positions, followed by enzymatic hydration to form hydroxymethyl trans-dihydrodiols. For 9-MA metabolism, the major metabolites identified were trans-1,2-dihydro-1,2-dihydroxy and trans-3,4-dihydro-3,4-dihydroxy derivatives of 9-MA and 9-OHMA. 9-OHMA was also metabolized to trans-1,2- and 3,4-dihydrodiol derivatives. The absolute configuration and optical purity were determined for each of the trans-dihydrodiols formed by fungal metabolism and compared with previously published circular dichroism spectral data obtained from rat liver microsomal metabolism of 9-MA, 9-OHMA, and 9,10-DMA. Circular dichroism spectral analysis revealed that the major enantiomer for each dihydrodiol was predominantly in the S,S configuration, in contrast to the predominantly R,R configuration of the trans-dihydrodiol formed by mammalian enzyme systems. These results indicate that C. elegans metabolizes methylated anthracenes in a highly stereoselective manner that is different from that reported for rat liver microsomes. |
| Databáze: | OpenAIRE |
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