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

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    Neamphamide A, a New HIV-Inhibitory Depsipeptide from the Papua New Guinea Marine Sponge Neamphius huxleyi†
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    Molecular Targets Development Program, Center for Cancer Research, National Cancer Institute, Building 1052, Room 121, Frederick, Maryland 21702-1201, Intramural Research Support Program, SAIC-Frederick, Frederick, Maryland 21702-1201, Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Disease, Bethesda, Maryland 20892-0805, and USA Cancer Research Institute, College of Medicine, University of South Alabama, 307 University Boulevard, MSB 2310, Mobile, Alabama 36688
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2004, 67, 8, 1407–1411
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    https://doi.org/10.1021/np040003f
    Published June 30, 2004
    Copyright © 2004 American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    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.

    Copyright © 2004 American Chemical Society and American Society of Pharmacognosy

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    †

     Dedicated to the late Dr. D. John Faulkner (Scripps) and the late Dr. Paul J. Scheuer (Hawaii) for their pioneering work on bioactive marine natural products.

    ‡

     Molecular Targets Development Program, CCR, NCI.

    *

     To whom correspondence should be addressed. Tel:  (301) 846-5391. Fax:  (301) 846-6919.

    §

     SAIC-Frederick.

    ⊥

     Laboratory of Bioorganic Chemistry, NIDDK.

    ‖

     Present address:  Exploratory Research Laboratories, Fujisawa Pharmaceutical Co. Ltd., 5-2-3 Tokodai, Tsukuba, Ibaraki, 300-2698, Japan.

    ∇

     USA Cancer Research Institute.

    ○

     Present address:  USA Cancer Research Institute, College of Medicine, University of South Alabama, Mobile, AL 36688.

    Supporting Information Available

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    1H, 13C, gCOSY45, gTOCSY, gHSQC, gHMBC, gNOESY, and gROESY spectra of compound 2. This material is available free of charge via the Internet at http:// pubs.acs.org.

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    Cite this: J. Nat. Prod. 2004, 67, 8, 1407–1411
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    https://doi.org/10.1021/np040003f
    Published June 30, 2004
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