| Fungal oxidation of (+/-)-9,10-dihydroxy-9,10-dihydrobenzo[a]pyrene: formation of diastereomeric benzo[a]pyrene 9,10-diol 7,8-epoxides. | |
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MedLine Citation:
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PMID: 6933504 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The filamentous fungus Cunninghamella elegans oxidized (+/-) trans-9,10-dihydroxy-9,10-dihydrobenzo[a]-pyrene to a complex mixture of metabolites which were detected by high-pressure liquid chromatography. Two of the metabolites were identified as (+/-)7 beta, 8 alpha, 9 alpha, 10 beta-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene and (+/-)-7 beta,8 alpha,9 beta,10 alpha-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene. A third product gave absorption and mass spectra consistent with a diol-epoxide structure. Hydrolysis of this compound gave (+/-)-7 beta, 8 alpha, 9 beta, 10 alpha-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene as the major identifiable product with a minor unidentified tetraol. Synthetic (+/-)-9 alpha, 10 beta-dihydroxy-7 beta, 8 beta-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene gave the same hydrolysis products and had the same retention time on high-pressure liquid chromatography as did the fungal metabolite. The trans-9,10-dihydroxy-9,10-dihydrobenzo[a]pyrene recovered at the end of the experiment showed no optical activity, indicating that both enantiomers were metabolized by the fungus. the results suggest that C. elegans oxidizes (+/-)-trans-9,10-dihydroxy-9,10-dihydrobenzo[a]pyrene to diastereomeric benzo[a]pyrene 9,10-diol 7,8-epoxides. |
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Authors:
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C E Cerniglia; D T Gibson |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Proceedings of the National Academy of Sciences of the United States of America Volume: 77 ISSN: 0027-8424 ISO Abbreviation: Proc. Natl. Acad. Sci. U.S.A. Publication Date: 1980 Aug |
Date Detail:
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Created Date: 1981-01-26 Completed Date: 1981-01-26 Revised Date: 2009-11-18 |
Medline Journal Info:
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Nlm Unique ID: 7505876 Medline TA: Proc Natl Acad Sci U S A Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 4554-8 Citation Subset: IM |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Benzopyrenes
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metabolism* Biotransformation Chromatography, High Pressure Liquid Epoxy Compounds Mucorales / metabolism* Oxidation-Reduction Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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CA 19078/CA/NCI NIH HHS; T32 CA 09182/CA/NCI NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Benzopyrenes; 0/Epoxy Compounds |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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