Abstract
Ulongapeptin (1), a cyclic depsipeptide, was isolated from a Palauan marine cyanobacterium Lyngbya sp. The gross structure was elucidated through one-dimensional TOCSY experiments and other spectroscopic techniques. The absolute and relative stereochemistry of the beta-amino acid, 3-amino-2-methyl-7-octynoic acid (AMO), in 1 was determined by synthesis of the saturated alpha-alkyl-beta-amino acid and Marfey's analysis of the acid hydrolysate of tetrahydro-1. Ulongapeptin (1) was cytotoxic against KB cells at an IC(50) value of 0.63 microM.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
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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Depsipeptides*
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Drug Screening Assays, Antitumor
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Humans
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Inhibitory Concentration 50
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KB Cells / drug effects
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Palau
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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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Stereoisomerism
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Tumor Cells, Cultured
Substances
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Antineoplastic Agents
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Depsipeptides
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Peptides, Cyclic
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ulongapeptin