Abstract
Lophocladines A (1) and B (2), two 2,7-naphthyridine alkaloids, were isolated from the marine red alga Lophocladiasp. collected in the Fijian Islands. Their structures were deduced on the basis of high-resolution mass spectra and one- and two-dimensional NMR spectroscopy. Lophocladine A (1) displayed affinity for NMDA receptors and was found to be a delta-opioid receptor antagonist, whereas lophocladine B (2) exhibited cytotoxicity to NCI-H460 human lung tumor and MDA-MB-435 breast cancer cell lines. Immunofluorescence studies indicated that the cytotoxicity of lophocladine B (2) was correlated with microtubule inhibition. This is the first reported occurrence of alkaloids based on a 2,7-naphthyridine skeleton from red algae.
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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Alkaloids* / chemistry
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Alkaloids* / isolation & purification
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Alkaloids* / pharmacology
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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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Drug Screening Assays, Antitumor
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Female
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Fiji
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Humans
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Molecular Structure
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Naphthyridines* / chemistry
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Naphthyridines* / isolation & purification
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Naphthyridines* / pharmacology
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Nuclear Magnetic Resonance, Biomolecular
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Receptors, N-Methyl-D-Aspartate / drug effects
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Receptors, Opioid, delta / antagonists & inhibitors
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Rhodophyta / chemistry*
Substances
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Alkaloids
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Antineoplastic Agents
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Naphthyridines
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Receptors, N-Methyl-D-Aspartate
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Receptors, Opioid, delta
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lophocladine A
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lophocladine B