Abstract
A new stereoisomer of malyngamide C, 8-epi-malyngamide C (1), and the known compound lyngbic acid [(4E,7S)-7-methoxytetradec-4-enoic acid] were isolated from a sample of Lyngbya majuscula collected near Bush Key, Dry Tortugas, Florida. The structure of 1 was determined by NMR and MS experiments. The absolute configuration of 1 was determined by selective Mitsunobu inversion of C-8 to give malyngamide C, as determined by NMR, MS, and comparison of specific rotation. Both 1 and malyngamide C were found to be cytotoxic to HT29 colon cancer cells (IC(50) 15.4 and 5.2 microM, respectively) and to inhibit bacterial quorum sensing in a reporter gene assay.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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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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Cyanobacteria / chemistry*
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Cyclohexanones / chemistry
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Cyclohexanones / isolation & purification*
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Cyclohexanones / pharmacology*
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Drug Screening Assays, Antitumor
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Fatty Acids, Monounsaturated / chemistry
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Fatty Acids, Monounsaturated / isolation & purification*
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Fatty Acids, Monounsaturated / pharmacology*
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Florida
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HT29 Cells
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Humans
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Inhibitory Concentration 50
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Marine Biology
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Quorum Sensing / physiology
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Stereoisomerism
Substances
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Antineoplastic Agents
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Cyclohexanones
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Fatty Acids, Monounsaturated
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malyngamide C