Abstract
An analogue of the potent microfilament-disrupter lyngbyabellin A (1) has been isolated as a minor metabolite from the marine cyanobacterium Lyngbya majuscula collected at Apra Harbor, Guam. It possesses slightly weaker cytotoxicity than 1 and has been named lyngbyabellin B (2). Primarily NMR spectroscopy was used to determine its structure. The absolute configuration of 2 has been ascertained by chiral HPLC analysis of degradation products and by comparison with lyngbyabellin A (1). The known modified tetrapeptide lyngbyapeptin A (3) has also been found in the same extract, and its absolute stereochemistry could be determined for the first time.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Bacterial Toxins / chemistry
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Bacterial Toxins / isolation & purification*
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Bacterial Toxins / pharmacology
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Cyanobacteria / chemistry*
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Cytotoxins / chemistry
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Cytotoxins / isolation & purification*
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Cytotoxins / pharmacology
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Depsipeptides*
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Inhibitory Concentration 50
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Lyngbya Toxins / chemistry
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Lyngbya Toxins / isolation & purification*
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Lyngbya Toxins / pharmacology
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Peptides, Cyclic / chemistry
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Peptides, Cyclic / isolation & purification
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Peptides, Cyclic / pharmacology
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Thiazoles / chemistry
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Thiazoles / isolation & purification*
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Thiazoles / pharmacology
Substances
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Bacterial Toxins
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Cytotoxins
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Depsipeptides
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Lyngbya Toxins
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Peptides, Cyclic
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Thiazoles
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lyngbyabellin A
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lyngbyabellin B