Abstract
Cetoniacytone A (1) and some related minor components (2, 6, 7) were produced by Actinomyces sp. (strain Lu 9419), which was isolated from the intestines of a rose chafer (Cetonia aureata). The structures of the novel metabolites were established by detailed spectroscopic analysis. The absolute configuration of 1 was determined by X-ray analysis and derivatisation with chiral acids. 1 exhibits a significant cytotoxicity against selected tumor cell lines. The biosynthesis of 1 was studied by feeding 13C labelled precursors. The results suggest that the characteristic p-C7N skeleton of the aminocarba sugar is formed via the pentose phosphate pathway by cyclisation of a heptulose phosphate intermediate.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Actinomyces / chemistry*
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Actinomyces / metabolism
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / metabolism
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Antineoplastic Agents / pharmacology
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Crystallography, X-Ray
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Culture Media
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Cyclohexanones / chemistry*
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Cyclohexanones / isolation & purification
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Cyclohexanones / metabolism
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Cyclohexanones / pharmacology*
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Drug Screening Assays, Antitumor
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Fermentation
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Glucose / metabolism
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Glycerol / metabolism
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Magnetic Resonance Spectroscopy
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Microbial Sensitivity Tests
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Molecular Structure
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Symbiosis
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Tumor Cells, Cultured
Substances
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Antineoplastic Agents
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Culture Media
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Cyclohexanones
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cetoniacytone A
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cetoniacytone B
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Glucose
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Glycerol