Abstract
Microbial transformation of the germacranolide pyrethrosin (1) using Rhizopus nigricans NRRL 1477 has resulted in the isolation of 6 alpha-acetoxy-1 beta,4 alpha-dihydroxy-5,7 alpha H,8 beta H-eudesm-11 beta,13-dihydro-8,12-olide (5), a new eudesmanolide-type metabolite, in addition to the previously reported eudesmanolides: 2, 3, 4, and 6. The structure elucidation of these metabolites was based primarily on 1D and 2D NMR analyses. The isolated metabolites exhibited cytotoxic, antifungal, and antiprotozoal activities.
MeSH terms
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Animals
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Anti-Infective Agents / chemistry
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Anti-Infective Agents / isolation & purification*
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Anti-Infective Agents / pharmacology
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Antifungal Agents / chemistry
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Antifungal Agents / isolation & purification*
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Antifungal Agents / pharmacology
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Antimalarials / chemistry
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Antimalarials / isolation & purification*
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Antimalarials / pharmacology
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification*
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Antineoplastic Agents, Phytogenic / pharmacology
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Biotransformation
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Candida albicans / drug effects
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Carcinoma, Squamous Cell
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Cryptococcus neoformans / drug effects
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Female
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Humans
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Magnetic Resonance Spectroscopy
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Melanoma
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Molecular Structure
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Ovarian Neoplasms
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Plasmodium falciparum / drug effects
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Pyrethrins / chemistry
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Pyrethrins / metabolism*
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Rhizopus / metabolism
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Sesquiterpenes / chemistry
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / metabolism*
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Sesquiterpenes / pharmacology
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Sesquiterpenes, Eudesmane*
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Tumor Cells, Cultured / drug effects
Substances
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6alpha-acetoxy-1beta,4alpha-dihydroxy-5,7alpha H,8 beta H-eudesm-11beta,13-dihydro-8,12-olide
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Anti-Infective Agents
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Antifungal Agents
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Antimalarials
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Antineoplastic Agents, Phytogenic
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Pyrethrins
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Sesquiterpenes
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Sesquiterpenes, Eudesmane
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pyrethrosin