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Isolation, Structural Elucidation, and Absolute Stereochemistry of Enigmazole A, a Cytotoxic Phosphomacrolide from the Papua New Guinea Marine Sponge Cinachyrella enigmatica

  1. Author:
    Oku, N.
    Takada, K.
    Fuller, R. W.
    Wilson, J. A.
    Peach, M. L.
    Pannell, L. K.
    McMahon, J. B.
    Gustafson, K. R.

  2. Author Address

    NCI, Mol Targets Lab, Ctr Canc Res, NCI Frederick, Frederick, MD 21701 USA. SAIC Frederick Inc, NCI Frederick, Biol Chem Lab, Frederick, MD 21702 USA. NIDDK, Bioorgan Chem Lab, Bethesda, MD 20892 USA.;Gustafson, KR, NCI, Mol Targets Lab, Ctr Canc Res, NCI Frederick, Bldg 1052,Room 121, Frederick, MD 21701 USA.;gustafki@mail.nih.gov
    1. Year: 2010
    2. Date: Aug
  2. Journal: Journal of the American Chemical Society
    1. 132
    2. 30
    3. Pages: 10278-10285
  4. Type of Article: Article
  5. ISSN: 0002-7863
  1. Abstract:

    Enigmazole A (1), a novel phosphate-containing macrolide, was isolated from a Papua New Guinea collection of the marine sponge Cinachyrella enigmatica. The structure of 1, including the absolute stereochemistry at all eight chiral centers, was determined by a combination of spectroscopic analyses and a series of microscale chemical derivatization studies. Compound 1 is comprised of an 18-membered phosphomacrolide that contains an embedded exomethylene-substituted tetrahydropyran ring and an acyclic portion that spans an embedded oxazole moiety. Two additional analogues, 15-O-methylenigmazole A and 13-hydroxy-15-O-methylenigmazole A, were also isolated and assigned. The enigmazoles are the first phosphomacrolides from a marine source and 1 exhibited significant cytotoxicity in the NCI 60-cell line antitumor screen, with a mean GI(50) of 1.7 mu M.

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External Sources

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  2. DOI: 10.1021/ja1016766
  3. View record in Web of Science®
  4. WOS: 000280456100025

Library Notes

  1. Fiscal Year: FY2009-2010
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