Abstract
Two new caprolactones, (R)-10-methyl-6-undecanolide (1) and (6R,10S)-10-methyl-6-dodecanolide (2), were identified in the lipid extract of a marine streptomycete (isolate B6007). Their structures were proposed on the basis of GC-MS experiments and proved by synthesis. The absolute configuration of the compounds was established by comparison of the natural and synthetic stereoisomers using chiral gas chromatography. These caprolactones show a moderate phytotoxicity and a promising activity against cancer cells with concomitant low general cytotoxicity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Bacterial Agents / chemical synthesis
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification*
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Anti-Bacterial Agents / pharmacology
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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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Drug Screening Assays, Antitumor
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Gas Chromatography-Mass Spectrometry
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Lactones / chemical synthesis
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Lactones / chemistry
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Lactones / isolation & purification*
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Lactones / pharmacology
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Marine Biology*
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Microbial Sensitivity Tests
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Molecular Structure
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Papua New Guinea
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Stereoisomerism
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Streptomyces / chemistry*
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Structure-Activity Relationship
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Tumor Cells, Cultured
Substances
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(6R,10S)-10-methyl-6-dodecanolide
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(R)-10-methyl-6-undecanolide
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Anti-Bacterial Agents
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Antineoplastic Agents
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Lactones