Microbial transformation of sampangine.
Microbial transformation studies of the antifungal alkaloid sampangine (2) have revealed that it is metabolized by a number of microorganisms. Using a standard two-stage fermentation technique, Beauvaria bassiana (ATCC 7159), Doratomyces microsporus (ATCC 16225), and Filobasidiella neoformans (ATCC 10226) produced the 4'-O-methyl-beta-glucopyranose conjugate (3), while Absidia glauca (ATCC 22752), Cunninghamella elegans (ATCC 9245), Cunninghamella species (NRRL 5695), and Rhizopus arrhizus (ATCC 11145) produced the beta-glucopyranose conjugate (4). Metabolites 3 and 4 have been characterized on the basis of spectral data. Both 3 and 4 had significant in vitro activity against Cryptococcus neoformans but were inactive against Candida albicans. Metabolite 4 was inactive in vivo in a mouse model of cryptococcosis.
Orabi
K Y
KY
Department of Pharmacognosy and National Center for the Development of Natural Products, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
Li
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Clark
A M
AM
Hufford
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CD
D000107:Acetylation; D000470:Alkaloids / Q000378:metabolism / Q000494:pharmacology*; D000818:Animals; D000935:Antifungal Agents / Q000378:metabolism* / Q000494:pharmacology*; D005285:Fermentation; D005658:Fungi / Q000187:drug effects / Q000378:metabolism*; D006576:Heterocyclic Compounds, 4 or More Rings; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008826:Microbial Sensitivity Tests; D009287:Naphthyridines; D012233:Rhizopus / Q000187:drug effects / Q000378:metabolism
D000470:Alkaloids; D000935:Antifungal Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D009287:Naphthyridines; C121572:sampangine