Abstract
Cancer cell toxicity-guided fractionation of extracts of the Papua New Guinea marine cyanobacteria Lyngbya majuscula and Lyngbya sordida led to the isolation of apratoxin D (1). Compound 1 contains the same macrocycle as apratoxins A and C but possesses the novel 3,7-dihydroxy-2,5,8,10,10-pentamethylundecanoic acid as the polyketide moiety. The planar structures and stereostructures of compound 1 were determined by extensive 1D and 2D NMR and MS data analyses and by comparison with the spectroscopic data of apratoxins A and C. Apratoxin D (1) showed potent in vitro cytotoxicity against H-460 human lung cancer cells with an IC 50 value of 2.6 nM.
Publication types
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Research Support, N.I.H., Extramural
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 / chemistry
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Depsipeptides / isolation & purification*
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Depsipeptides / pharmacology*
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Drug Screening Assays, Antitumor
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Humans
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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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Marine Toxins / chemistry
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Marine Toxins / isolation & purification*
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Marine Toxins / pharmacology*
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Papua New Guinea
Substances
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Antineoplastic Agents
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Depsipeptides
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Lyngbya Toxins
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Marine Toxins
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apratoxin D