Abstract
Versicolactones A-D (1-4), four new butyrolactones, along with four known butyrolactones (5-8) were isolated from the fermentation products of the endophytic fungus Aspergillus versicolor. The structures of compounds 1-4, including absolute configuration, were elucidated by interpretation of the NMR and CD data. Compound 2 was further confirmed by single-crystal X-ray diffraction analysis. In particular, compound 1 is the first naturally occurring butyrolactone possessing an unusual 2-oxopropyl group. More importantly, compounds 1 and 8 displayed significant antitobacco mosaic virus activities with inhibition rates of 46.4 % and 35.4 %, even more potent than the positive control ningnanmycin (30.8 %). Compound 1 also showed moderate cytotoxicity against A549 and MCF7 cells with IC50 values of 3.2 and 2.5 µM, respectively.
Georg Thieme Verlag KG Stuttgart · New York.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adenocarcinoma / drug therapy
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Adenocarcinoma of Lung
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / pharmacology
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Antineoplastic Agents / therapeutic use
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Antiviral Agents / chemistry
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Antiviral Agents / isolation & purification
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Antiviral Agents / pharmacology*
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Aspergillus / chemistry*
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Biological Products / chemistry
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Biological Products / pharmacology*
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Biological Products / therapeutic use
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Breast Neoplasms / drug therapy
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Fermentation
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Humans
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Inhibitory Concentration 50
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Lactones / chemistry
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Lactones / isolation & purification
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Lactones / pharmacology*
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Lactones / therapeutic use
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Lung Neoplasms / drug therapy
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MCF-7 Cells
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Molecular Structure
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Sesquiterpenes / chemistry
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Sesquiterpenes / isolation & purification
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Sesquiterpenes / pharmacology*
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Sesquiterpenes / therapeutic use
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Tobacco Mosaic Virus / drug effects*
Substances
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Antineoplastic Agents
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Antiviral Agents
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Biological Products
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Lactones
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Sesquiterpenes
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versicolactone A