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

Research output: Contribution to journalArticle

55 Citations (Scopus)

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

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Lophocladia
Naphthyridines
Rhodophyta
Cytotoxicity
Algae
Alkaloids
cytotoxicity
alkaloids
receptors
Narcotic Antagonists
narcotics
lung neoplasms
N-Methyl-D-Aspartate Receptors
breast neoplasms
microtubules
Nuclear magnetic resonance spectroscopy
fluorescent antibody technique
skeleton
nuclear magnetic resonance spectroscopy
Tumors

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., ... 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

Lophocladines, bioactive alkaloids from the red alga lophocladia sp. / Gross, Harald; Goeger, Douglas E.; Hills, Patrice; Mooberry, Susan L.; Ballantine, David L.; Murray, Thomas F.; Valeriote, Frederick A.; Gerwick, William H.

In: Journal of Natural Products, Vol. 69, No. 4, 04.2006, p. 640-644.

Research output: Contribution to journalArticle

Gross, H, Goeger, DE, Hills, P, Mooberry, SL, Ballantine, DL, Murray, TF, Valeriote, FA & Gerwick, WH 2006, 'Lophocladines, bioactive alkaloids from the red alga lophocladia sp.', Journal of Natural Products, vol. 69, no. 4, pp. 640-644. https://doi.org/10.1021/np050519e
Gross, Harald ; Goeger, Douglas E. ; Hills, Patrice ; Mooberry, Susan L. ; Ballantine, David L. ; Murray, Thomas F. ; Valeriote, Frederick A. ; Gerwick, William H. / Lophocladines, bioactive alkaloids from the red alga lophocladia sp. In: Journal of Natural Products. 2006 ; Vol. 69, No. 4. pp. 640-644.
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