Nonthmicin, a Polyether Polyketide Bearing a Halogen-Modified Tetronate with Neuroprotective and Antiinvasive Activity from <i>Actinomadura</i> sp.

  • Yasuhiro Igarashi
    Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan
  • Noriaki Matsuoka
    Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan
  • Yasuko In
    Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences, Takatsuki, Osaka 569-1041, Japan
  • Tetsushi Kataura
    Bioscience and Informatics, Keio University, Yokohama, Kanagawa 223-8522, Japan
  • Etsu Tashiro
    Bioscience and Informatics, Keio University, Yokohama, Kanagawa 223-8522, Japan
  • Ikuo Saiki
    Department of Bioscience, Institute of Natural Medicine, Toyama University, 2630 Sugitani, Toyama 930-0194, Japan
  • Yuri Sudoh
    Hyphagenesis, Inc., 2-18-28 Tamagawa Gakuen, Machida, Tokyo 194-0041, Japan

書誌事項

公開日
2017-03-03
資源種別
journal article
DOI
  • 10.1021/acs.orglett.7b00318
公開者
American Chemical Society (ACS)

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説明

Nonthmicin (1), a new polyether polyketide bearing a chlorinated tetronic acid, was isolated from the culture extract of a soil-derived Actinomadura strain. The structure of 1 was elucidated by interpretation of NMR and MS spectroscopic data, and the absolute configuration of 1 was proposed on the basis of the crystal structure of its dechloro congener ecteinamycin (2) also isolated from the same strain. Tetronic acids modified by halogenation have never been reported from natural products. Compounds 1 and 2 were found to have neuroprotective activity and antimetastatic properties at submicromolar concentrations in addition to antibacterial activity.

収録刊行物

  • Organic Letters

    Organic Letters 19 (6), 1406-1409, 2017-03-03

    American Chemical Society (ACS)

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