Abstract
A new class of four depsipentapeptides called chaiyaphumines A-D (1-4) was isolated from Xenorhabdus sp. PB61.4. Their structures were elucidated by detailed 1D and 2D NMR experiments and by a Marfey's analysis following flash hydrolysis of the peptide. Verification of the structure was achieved by three-dimensional modeling using NOE-derived distance constraints, molecular dynamics, and energy minimization. Chaiyaphumine A (1) showed good activity against Plasmodium falciparum (IC50 of 0.61 μM), the causative agent of malaria, and was active against other protozoal tropical disease causing agents.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antiparasitic Agents / chemistry
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Antiparasitic Agents / isolation & purification*
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Antiparasitic Agents / pharmacology*
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Bacillus subtilis / drug effects
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Depsipeptides / chemistry
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Depsipeptides / isolation & purification*
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Depsipeptides / pharmacology*
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Escherichia coli / drug effects
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Humans
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Inhibitory Concentration 50
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Micrococcus luteus / drug effects
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Molecular Structure
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Nematoda / drug effects
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Nuclear Magnetic Resonance, Biomolecular
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Parasitic Sensitivity Tests
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Plasmodium falciparum / drug effects*
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Saccharomyces cerevisiae / drug effects
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Thailand
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Trypanosoma brucei rhodesiense / drug effects
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Trypanosoma cruzi / drug effects
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Xenorhabdus / chemistry*
Substances
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Antiparasitic Agents
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Depsipeptides
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chaiyaphumine A