Abstract
Leucamide A (1), a bioactive cyclic heptapeptide containing a unique mixed 4,2-bisheterocycle tandem pair consisting of a methyloxazole and thiazole subunit was isolated together with the known compound BRS1 (2), from the dichloromethane extract of the Australian marine sponge Leucetta microraphis. The planar structure of leucamide A (1) was elucidated by employing spectroscopic techniques (NMR, MS, UV, and IR). Its absolute stereochemistry was established by chemical degradation, derivatization, and chiral GC[bond]MS analysis. A conformational analysis of 1 was made using MMFF. Leucamide A (1) was found to be moderately cytotoxic toward several tumor cell lines.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amino Acids / chemistry
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Amino Alcohols / chemistry
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Amino Alcohols / isolation & purification
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Amino Alcohols / pharmacology
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Animals
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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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Australia
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Cells, Cultured / drug effects
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Chromatography, High Pressure Liquid
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Drug Screening Assays, Antitumor
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Fatty Alcohols / chemistry
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Fatty Alcohols / isolation & purification
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Fatty Alcohols / pharmacology
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Gas Chromatography-Mass Spectrometry
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Humans
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Liver Neoplasms
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Models, Molecular
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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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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Porifera / chemistry*
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Stereoisomerism
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Stomach Neoplasms
Substances
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Amino Acids
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Amino Alcohols
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Antineoplastic Agents
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BRS1 compound
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Fatty Alcohols
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Peptides, Cyclic
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leucamide A