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Spiro[3.5]nonenyl Meroterpenoid Lactones, Cryptolaevilactones G-L, an Ionone Derivative, and Total Synthesis of Cryptolaevilactone M from Cryptocarya laevigata

  1. Author:
    Tsurumi, Fumika
    Miura, Yuta
    Nakano, Misaki
    Saito, Yohei [ORCID]
    Fukuyoshi, Shuichi [ORCID]
    Miyake, Katsunori [ORCID]
    Newman, David J [ORCID]
    O'Keefe,Barry [ORCID]
    Lee, Kuo-Hsiung [ORCID]
    Nakagawa-Goto, Kyoko [ORCID]

  2. Author Address

    School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences , Kanazawa University , Kanazawa , 920-1192 , Japan., Tokyo University of Pharmacy and Life Sciences , Hachioji , Tokyo 192-0392 , Japan., NIH Special Volunteer , Wayne , Pennsylvania 19087 , United States., Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, and Molecular Targets Program, Center for Cancer Research , National Cancer Institute, NCI at Frederick , Frederick , Maryland 21702-1201 , United States., Natural Products Research Laboratories, UNC Eshelman School of Pharmacy , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599-7568 , United States., Chinese Medicine Research and Development Center , China Medical University and Hospital , 2 Yuh-Der Road , Taichung , 40447 , Taiwan.,
    1. Year: 2019
    2. Date: SEP
    3. Epub Date: 2019 08 23
  2. Journal: Journal of natural products
    1. 82
    2. 9
    3. Pages: 2368-2378
  4. Type of Article: Article
  5. ISSN: 0163-3864
  1. Abstract:

    A CH3OH-CH2Cl2 (1:1) extract (N025439) of the leaves and twigs of Cryptocarya laevigata furnished eight new compounds, 1-8. Based on extensive 1D and 2D NMR spectroscopic data examination, the new d-lactone derivatives 1-6 are monoterpene-polyketide hybrids containing a unique spiro[3.5]nonenyl moiety. Their trivial names, cryptolaevilactones G-L, follow those of the related known meroterpenoids cryptolaevilactones A-F. Cryptolaevilactone L (6) contains 11,12-cis-oriented substituents, while the other cryptolaevilactones contain trans-oriented groups. The structure of the linear d-lactone 7, cryptolaevilactone M, was characterized from various spectroscopic data analysis, and the absolute configuration was determined by total synthesis through stereoselective allylation and Grubbs olefin metathesis. Compound 8 was elucidated to be an ionone derivative with a 3,4-syn-diol functionality.

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  1. Keywords:

External Sources

  1. View Full Text
  2. DOI: 10.1021/acs.jnatprod.8b00732
  3. PMID: 31442048
  4. View record in Web of Science®
  5. WOS: 000488424000002

Library Notes

  1. Fiscal Year: FY2018-2019
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