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Synthetic studies and SAR of the structurally complex indole diterpenes showing strong insecticidal activities

Research Project

Project/Area Number 23780112
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionNational Institute of Advanced Industrial Science and Technology (2012-2013)
Tohoku University (2011)

Principal Investigator

ENOMOTO Masaru  独立行政法人産業技術総合研究所, 生物プロセス研究部門, 研究員 (90546342)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywords天然有機化合物 / indole diterpine / paspalinine / lecanindole D / 全合成 / 構造活性相関 / thiersinine / 部分構造 / 構造活性相関研究 / nodulisporic acid / paspalicine / 殺虫活性
Research Abstract

Indole diterpenes are known to possess intriguing biological activity such as insecticidal, mito-inhibitory, and anti-MRSA activities. Therefore, synthetic studies and chemical supply of these compounds could solve the mechanism of action and contribute to development of various biology such as chemical ecology, cell biology, medicinal science. But, it was difficult to synthesis this family of natural products due to their complex structures. In this study, we have developed an efficient method to construct the indole diterpine framework and achieved total synthesis of paspalinine, a tremorgenic alkaloid, and lecanindole D, a progesterone receptor agonist.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (30 results)

All 2014 2013 2012 2011 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (20 results) Remarks (5 results)

  • [Journal Article] TotalTotal synthesis of aurachins C, D, and L, and a structurally simplified analog of aurachin C2014

    • Author(s)
      Masaru Enomoto, Wataru Kitagawa, Yoshiaki Yasutake and Hiroki Shimizu
    • Journal Title

      Bioscience, Biotechnology and Biotechnology

      Volume: (in press) Pages: 78-78

    • URL

      https://www.jstage.jst.go.jp/browse/bbb

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (±)-Lecanindole D2013

    • Author(s)
      Akiko Asanuma, Masaru Enomoto, Tomohiro Nagasawa, and Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Pages: 4561-4563

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (±)-lecanindole D2013

    • Author(s)
      Akiko Asanuma, Masaru Enomoto, Tomohiro Nagasawa and Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 34 Pages: 4561-4563

    • DOI

      10.1016/j.tetlet.2013.06.084

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of the Tremorgenic Indole Diterpene Paspalinine2012

    • Author(s)
      Masaru Enomoto, Akira Morita, Shigefumi Kuwahara
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 51 Pages: 12833-12836

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Substrate Specificity of The Aspartate : Alanine antiporter (AspT) of Tetragenococcus halophilus in Reconstituted Liposomes2011

    • Author(s)
      Ayako Sasahara, Kei Nanatani, Masaru Enomoto, Shigefumi Kuwahara, Keietsu Abe
    • Journal Title

      The Journal of Biological Chemistry

      Volume: 286 Issue: 33 Pages: 29044-29052

    • DOI

      10.1074/jbc.m111.260224

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 抗菌活性物質aurachin類およびそのアナログ化合物の合成研究2014

    • Author(s)
      榎本賢、北川航、安武義晃、清水弘
    • Organizer
      日本農芸化学会2014年度大会
    • Place of Presentation
      東京
    • Year and Date
      2014-03-29
    • Related Report
      2013 Final Research Report
  • [Presentation] 抗菌活性物質aurachin類およびそのアナログ化合物の合成研究2014

    • Author(s)
      榎本賢、北川航、安武義晃、清水弘樹
    • Organizer
      日本農芸化学会2014年度大会
    • Place of Presentation
      明治大学生田キャンパス(神奈川県川崎市)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 抗菌活性物質aurachin類およびそのアナログ化合物の合成研究2013

    • Author(s)
      榎本賢、北川航、安武義晃、清水弘
    • Organizer
      日本農芸化学会2014年度北海道支部大会
    • Place of Presentation
      北海道
    • Year and Date
      2013-11-29
    • Related Report
      2013 Final Research Report
  • [Presentation] 生物活性天然物部分構造を付与した金ナノ粒子の合成研究2013

    • Author(s)
      榎本賢、桑原重文、清水弘樹
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      仙台
    • Year and Date
      2013-03-25
    • Related Report
      2013 Final Research Report
  • [Presentation] 黄体ホルモン作用物質Lecanindole Dの合成研究2013

    • Author(s)
      浅沼明子、榎本賢、永沢友裕、桑原重文
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      仙台
    • Year and Date
      2013-03-25
    • Related Report
      2013 Final Research Report
  • [Presentation] 癌細胞浸潤阻害物質BU-4664Lの合成研究2013

    • Author(s)
      藤田聡美、渡邊麻衣、廣川高史、榎本賢、桑原重文
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      仙台
    • Year and Date
      2013-03-25
    • Related Report
      2013 Final Research Report
  • [Presentation] AI-77-BおよびSg17-1-4の合成研究2013

    • Author(s)
      鈴木智美、永沢友裕、榎本賢、桑原重文
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      仙台
    • Year and Date
      2013-03-25
    • Related Report
      2013 Final Research Report
  • [Presentation] 抗炎症活性物質Rossinone Aの合成研究2013

    • Author(s)
      滝野ちあき、榎本賢、桑原重文
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      仙台
    • Year and Date
      2013-03-25
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthetic Studies on Sg17-1-42013

    • Author(s)
      Tomomi Suzuki, Tomohiro Nagasawa, Masaru Enomoto and Shigefumi Kuwahara
    • Organizer
      International Symposium for the 70^<th> Aniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      Sendai.
    • Related Report
      2013 Final Research Report
  • [Presentation] Total Synthesis of Paspalinine2013

    • Author(s)
      Masaru Enomoto, Akira Morita and Shigefumi Kuwahara
    • Organizer
      13^<th> International Conference on the Chemistry of Antibiotics and Other Bioactive Compounds
    • Place of Presentation
      Yamanashi.
    • Related Report
      2013 Final Research Report
  • [Presentation] Total Synthesis of Paspalinine2013

    • Author(s)
      Shigefumi Kuwahara, Masaru Enomoto and Akira Morita
    • Organizer
      Tohoku University Campus Asia Summer School
    • Place of Presentation
      Sendai, L-1, oral
    • Related Report
      2013 Final Research Report
  • [Presentation] 抗菌活性物質aurachin類およびそのアナログ化合物の合成研究2013

    • Author(s)
      榎本賢、北川航、安武義晃、清水弘樹
    • Organizer
      日本農芸化学会北海道支部講演会
    • Place of Presentation
      北海道大学農学部(北海道札幌市)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 生物活性天然物部分構造を付与した金ナノ粒子の合成研究2013

    • Author(s)
      榎本賢、桑原重文、清水弘樹
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内北キャンパス(仙台市)
    • Related Report
      2012 Research-status Report
  • [Presentation] Paspalinineの全合成2012

    • Author(s)
      榎本賢、森田暁、桑原重文
    • Organizer
      第54回天然有機化合物討論会
    • Place of Presentation
      東京
    • Year and Date
      2012-09-20
    • Related Report
      2013 Final Research Report
  • [Presentation] PaspalicineおよびPaspalinineの合成研究2012

    • Author(s)
      榎本賢、森田暁、桑原重文
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-24
    • Related Report
      2013 Final Research Report
  • [Presentation] Paspalinineの全合成2012

    • Author(s)
      榎本賢、森田暁、桑原重文
    • Organizer
      第54回天然有機化合物討論会
    • Place of Presentation
      東京農業大学世田谷キャンパス(世田谷区)
    • Related Report
      2012 Research-status Report
  • [Presentation] 特異な複素環構造を有する生物活性天然物の合成研究2011

    • Author(s)
      榎本賢
    • Organizer
      日本農芸化学会東北支部第12回若手の会
    • Place of Presentation
      山形
    • Year and Date
      2011-10-07
    • Related Report
      2013 Final Research Report
  • [Presentation] Total Synthesis of Paspalinine

    • Author(s)
      榎本賢、森田暁、桑原重文
    • Organizer
      日本農芸化学会北海道支部夏期シンポジウム
    • Place of Presentation
      北海道大学水産学部(函館市)
    • Related Report
      2012 Research-status Report
  • [Presentation] 特異な複素環構造を有する生物活性天然物の合成研究

    • Author(s)
      榎本賢
    • Organizer
      2011年度日本農芸化学会東北支部若手奨励賞受賞講演(招待講演)
    • Place of Presentation
      山形県鶴岡市
    • Related Report
      2011 Research-status Report
  • [Presentation] Paspalicineおよびpaspalinineの合成研究

    • Author(s)
      榎本賢、森田暁、桑原重文
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都市
    • Related Report
      2011 Research-status Report
  • [Remarks] 東北大学大学院農学研究科生物有機化学分野

    • URL

      http://www.agri.tohoku.ac.jp/yuuki/abc/Top.html

    • Related Report
      2013 Final Research Report
  • [Remarks] (独)産業技術総合研究所生物プロセス研究部門

    • URL

      https://unit.aist.go.jp/bpri/

    • Related Report
      2013 Final Research Report
  • [Remarks] 独立行政法人産業技術総合研究所

    • URL

      http://www.aist.go.jp/index_ja.html

    • Related Report
      2013 Annual Research Report
  • [Remarks] 独立行政法人産業技術総合研究所

    • URL

      http://www.aist.go.jp/index_ja.html

    • Related Report
      2012 Research-status Report
  • [Remarks]

    • URL

      http://www.agri.tohoku.ac.jp/yuuki/index-j.html

    • Related Report
      2011 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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