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

doi:10.1021/np050519e

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

Department of Pharmacology

Research output: Contribution to journal › Article › peer-review

86 Scopus citations

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 language	English (US)
Pages (from-to)	640-644
Number of pages	5
Journal	Journal of Natural Products
Volume	69
Issue number	4
DOIs	https://doi.org/10.1021/np050519e
State	Published - Apr 2006

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/np050519e

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title = "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 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.",

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T1 - Lophocladines, bioactive alkaloids from the red alga lophocladia sp.

AU - Gross, Harald

AU - Goeger, Douglas E.

AU - Hills, Patrice

AU - Mooberry, Susan L.

AU - Ballantine, David L.

AU - Murray, Thomas F.

AU - Valeriote, Frederick A.

AU - Gerwick, William H.

PY - 2006/4

Y1 - 2006/4

N2 - 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.

AB - 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.

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JF - Journal of Natural Products

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ER -

Lophocladines, bioactive alkaloids from the red alga lophocladia sp.

Abstract

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