The metabolism of muzigadial by microorganisms.
1. A total of 114 microorganisms were evaluated for their ability to metabolize the antifungal drimane sesquiterpene, muzigadial. 2. Cryptococcus neoformans was found to convert muzigadial to one major metabolite, identified as a hemiacetal. 3. Streptomyces platensis produced three metabolites: the hemiacetal, its corresponding lactone, and the epoxide of the hemiacetal. 4. Streptomyces spectabilis produced the hemiacetal as well as the epoxy hemiacetal. 5. The proposed structures of all of the metabolites were based on comparisons of the spectroscopic data (1H- and 13C-n.m.r. spectra and mass spectra) between the metabolites and the parent compound. 6. Antimicrobial evaluation of the microbial metabolites indicate that metabolism decreases antifungal activity.
Jurgens
T M
TM
Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University 38677.
Hufford
C D
CD
Clark
A M
AM
D000935:Antifungal Agents / Q000378:metabolism* / Q000494:pharmacology / Q000633:toxicity; D002175:Candida / Q000187:drug effects; D002855:Chromatography, Thin Layer; D003454:Cryptococcus / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D005285:Fermentation; D007928:Lethal Dose 50; D012717:Sesquiterpenes / Q000378:metabolism* / Q000494:pharmacology / Q000633:toxicity; D013302:Streptomyces / Q000378:metabolism*
D000935:Antifungal Agents; D012717:Sesquiterpenes; C077185:muzigadial