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Elucidation of Spirodactylone, a Polycyclic Alkaloid from the Sponge Dactylia sp., and Nonenzymatic Generation from the Co-metabolite Denigrin B

  1. Author:
    Kang,Unwoo
    Caldwell,Donald
    Cartner, Laura K.
    Wang,Dongdong
    Kim,Chang-Kwon
    Tian, Xiangrong
    Bokesch,Heidi
    Henrich,Curtis
    Woldemichael,Girma
    Schnermann,Martin
    Gustafson,Kirk

  2. Author Address

    NCI, Mol Targets Program, Ctr Canc Res, Frederick, MD 21702 USA.NCI, Biol Chem Lab, Ctr Canc Res, Frederick, MD 21702 USA.NCI, Basic Sci Program, Leidos Biomed Res Inc, Frederick Natl Lab Canc Res, Frederick, MD 21702 USA.Northwest A&F Univ, Coll Plant Protect, Res & Dev Ctr Biorat Pesticide, Yangling 712100, Shaanxi, Peoples R China.
    1. Year: 2019
    2. Date: Jun 21
  2. Journal: ORGANIC LETTERS
  3. AMER CHEMICAL SOC,
    1. 21
    2. 12
    3. Pages: 4750-4753
  5. Type of Article: Article
  6. ISSN: 1523-7060
  1. Abstract:

    Spirodactylone (1), a hexacyclic indolizidone alkaloid possessing a novel Spiro ring system, was isolated from the marine sponge Dactylia sp. The structure was elucidated by extensive spectroscopic methods including application of the LR-HSQMBC NMR pulse sequence. Oxidative cyclization of denigrin B (2), an aryl-substituted 2-oxo-pyrroline derivative that was also isolated from the sponge extract, provided material identical to spirodactylone (1). This confirmed the assigned structure and provides insight into the probable biogenesis of 1.

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External Sources

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  2. DOI: 10.1021/acs.orglett.9b01636
  3. PMID: 31150264
  4. View record in Web of Science®
  5. WOS: 000473116000075

Library Notes

  1. Fiscal Year: FY2018-2019
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