Lophocladines, bioactive alkaloids from the red alga lophocladia sp.

Harald Gross, Douglas E. Goeger, Patrice Hills, Susan L. Mooberry, David L. Ballantine, Thomas F. Murray, Frederick A. Valeriote, William H. Gerwick

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Abstract

Lophocladines A (1) and B (2), two 2,7-naphthyridine alkaloids, were isolated from the marine red alga Lophocladia sp. 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 δ-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.

Original languageEnglish
Pages (from-to)640-644
Number of pages5
JournalJournal of Natural Products
Volume69
Issue number4
DOIs
StatePublished - Apr 2006
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Gross, H., Goeger, D. E., Hills, P., Mooberry, S. L., Ballantine, D. L., Murray, T. F., Valeriote, F. A., & Gerwick, W. H. (2006). Lophocladines, bioactive alkaloids from the red alga lophocladia sp. Journal of Natural Products, 69(4), 640-644. https://doi.org/10.1021/np050519e