Neamphamide A, a New HIV-Inhibitory Depsipeptide from the Papua New Guinea Marine Sponge Neamphius huxleyi

A new HIV-inhibitory cyclic depsipeptide, neamphamide A (2), was isolated from a Papua New Guinea collection of the marine sponge Neamphius huxleyi. Its structure was established through interpretation of spectroscopic data and by acid hydrolysis, derivatization of the free amino acids, and LC-MS an...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2004-08, Vol.67 (8), p.1407-1411
Main Authors: Oku, Naoya, Gustafson, Kirk R, Cartner, Laura K, Wilson, Jennifer A, Shigematsu, Nobuharu, Hess, Sonja, Pannell, Lewis K, Boyd, Michael R, McMahon, James B
Format: Article
Language:English
Subjects:
Animals
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Anti-HIV Agents - pharmacology
Biological and medical sciences
Depsipeptides
General pharmacology
HIV-1 - drug effects
Human immunodeficiency virus
Human immunodeficiency virus 1
Marine
Medical sciences
Molecular Structure
Neamphius huxleyi
Papua New Guinea
Peptides, Cyclic - chemistry
Peptides, Cyclic - isolation & purification
Peptides, Cyclic - pharmacology
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Porifera
Porifera - chemistry
Stereoisomerism
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Summary:A new HIV-inhibitory cyclic depsipeptide, neamphamide A (2), was isolated from a Papua New Guinea collection of the marine sponge Neamphius huxleyi. Its structure was established through interpretation of spectroscopic data and by acid hydrolysis, derivatization of the free amino acids, and LC-MS analysis of the derivatives. Neamphamide A (2) contains 11 amino acid residues and an amide-linked 3-hydroxy-2,4,6-trimethylheptanoic acid moiety. The amino acid constituents were identified as l-Leu, l-NMeGln, d-Arg, d- and l-Asn, two residues of d-allo-Thr, l-homoproline, (3S,4R)-3,4-dimethyl-l-glutamine, β-methoxytyrosine, and 4-amino-7-guanidino-2,3-dihydroxyheptanoic acid. In a cell-based XTT assay, 2 exhibited potent cytoprotective activity against HIV-1 infection with an EC50 of approximately 28 nM.
ISSN:0163-3864
1520-6025
DOI:10.1021/np040003f