Lophocladines, bioactive alkaloids from the red alga Lophocladia sp.

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.

• Authors: Harald Gross, Douglas E Goeger, Patrice Hills, Susan L Mooberry, David L Ballantine, Thomas F Murray, Frederick A Valeriote, William H Gerwick
• Journal: Journal of natural products (J Nat Prod) Vol. 69 Issue 4 Pg. 640-4 (Apr 2006) ISSN: 0163-3864 [Print] United States
• PMID: 16643042 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• Alkaloids
• Antineoplastic Agents
• Naphthyridines
• Receptors, N-Methyl-D-Aspartate
• Receptors, Opioid, delta
• lophocladine A
• lophocladine B

Topics

• Alkaloids (chemistry, isolation & purification, pharmacology)
• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Female
• Fiji
• Humans
• Molecular Structure
• Naphthyridines (chemistry, isolation & purification, pharmacology)
• Nuclear Magnetic Resonance, Biomolecular
• Receptors, N-Methyl-D-Aspartate (drug effects)
• Receptors, Opioid, delta (antagonists & inhibitors)
• Rhodophyta (chemistry)