Abstract
Two new cytotoxins have been isolated from a species of marine cyanobacterium belonging to the genus Symploca that was collected in Guam. These new compounds, micromide (1) and guamamide (2), were accompanied by the known lipopeptides apramides A (3), B (4), and G (5). The planar structures of both alkaloids were elucidated by standard 2D NMR techniques, and the configurations of the amino acid-derived units in 1 were determined by chiral HPLC. The stereochemistry of the beta-methoxyhexanoic acid in 1 was determined by derivatization with methyl d-mandelate, after acid hydrolysis, and comparison with synthetic standards.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkaloids / chemistry
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Alkaloids / isolation & purification*
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Alkaloids / pharmacology
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Cell Line, Tumor
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Chromatography, High Pressure Liquid
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Cyanobacteria / chemistry*
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Drug Screening Assays, Antitumor
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Guam
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Humans
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Inhibitory Concentration 50
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KB Cells
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Lipoproteins / chemistry
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Lipoproteins / isolation & purification*
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Lipoproteins / pharmacology
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oligopeptides / chemistry
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Oligopeptides / isolation & purification*
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Oligopeptides / pharmacology
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Stereoisomerism
Substances
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Alkaloids
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Lipoproteins
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Oligopeptides
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apramide A
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apramide B
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apramide G
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guamamide
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micromide