Abstract
Fractionation of the extract of the marine cyanobacterium Lyngbya majuscula collected from Panama led to the isolation of malyngolide dimer (1). The planar structure of 1 was determined using 1D and 2D NMR spectroscopy and HRESI-TOFMS. The absolute configuration was established by chemical degradation followed by chiral GC-MS analyses and comparisons with an authentic sample of malyngolide seco-acid (4). Compound 1 showed moderate in vitro antimalarial activity against chloroquine-resistant Plasmodium falciparum (W2) (IC(50) = 19 microM) but roughly equivalent toxicity against H-460 human lung cell lines. Furthermore, because the closely related cyanobacterial natural product tanikolide dimer (5) was a potent SIRT2 inhibitor, compound 1 was evaluated in this assay but found to be essentially inactive.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Chloroquine / pharmacology
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Cyanobacteria / chemistry*
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Drug Resistance / drug effects
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Ethers, Cyclic / chemistry
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Ethers, Cyclic / isolation & purification*
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Ethers, Cyclic / pharmacology*
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Humans
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Lactones / chemistry
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Lactones / isolation & purification
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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 Biology
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Panama
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Parasitic Sensitivity Tests
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Plasmodium falciparum / drug effects*
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Pyrones / chemistry
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Pyrones / isolation & purification
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Pyrones / pharmacology
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Structure-Activity Relationship
Substances
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Ethers, Cyclic
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Lactones
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Lyngbya Toxins
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Pyrones
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malyngolide dimer
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tanikolide
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malyngolide
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Chloroquine