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...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1999-07, Vol.62 (7), p.988-992
Main Authors: Orabi, Khaled Y, Li, Erguang, Clark, Alice M, Hufford, Charles D
Format: Article
Language:English
Subjects:
4'-Methyl-^b-glucopyranose
Acetylation
alkaloids
Alkaloids - metabolism
Alkaloids - pharmacology
Animals
Annonaceae
antibiotics
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antifungal agents
Antifungal Agents - metabolism
Antifungal Agents - pharmacology
antifungal properties
Beauveria bassiana
Bioconversions. Hemisynthesis
biodegradation
Biological and medical sciences
Biotechnology
Candida albicans
chemical constituents of plants
chemical structure
cleistophathis patens
Cryptococcus neoformans
Cunninghamella elegans
Doratomyces microsporus
Fermentation
Filobasidiella neoformans
Fundamental and applied biological sciences. Psychology
Fungi - drug effects
Fungi - metabolism
Heterocyclic Compounds, 4 or More Rings
Hydrolysis
Magnetic Resonance Spectroscopy
Medical sciences
medicinal plants
metabolism
metabolites
Methods. Procedures. Technologies
Mice
Microbial Sensitivity Tests
Pharmacology. Drug treatments
Rhizopus - drug effects
Rhizopus - metabolism
sampangine
spectral analysis
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Summary: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-β-glucopyranose conjugate (3), while Absidia glauca (ATCC 22752), Cunninghamella elegans (ATCC 9245), Cunninghamella species (NRRL 5695), and Rhizopus arrhizus (ATCC 11145) produced the β-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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np980457a