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Elucidation of mode-of-action of maitotoxin based on chemical synthesis

Research Project

Project/Area Number 16H04112
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKyushu University

Principal Investigator

Oishi Tohru  九州大学, 理学研究院, 教授 (90241520)

Co-Investigator(Kenkyū-buntansha) 此木 敬一  東北大学, 農学研究科, 准教授 (40292825)
Research Collaborator TORIKAI Kohei  
EBINE Makoto  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥17,290,000 (Direct Cost: ¥13,300,000、Indirect Cost: ¥3,990,000)
Fiscal Year 2018: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2017: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥8,710,000 (Direct Cost: ¥6,700,000、Indirect Cost: ¥2,010,000)
Keywordsマイトトキシン / 梯子状ポリエーテル / カルシウムイオン流入活性 / 化学合成 / 生物活性発現機構 / Ca2+流入活性 / 生物活性 / ポリエーテル / 天然物
Outline of Final Research Achievements

Maitotoxin (MTX) is one of the causative toxins of ciguatera seafood poisoning, and it elicits potent calcium ion influx activity in cells. In this study, development of an inhibitor against the calcium ion influx activity by synthesizing a simplified artificial analog based on the partial structure of MTX. For this purpose, a partial structure corresponding to the hydrophobic part of MTX whose molecular weight exceeds 1000 was designed. The WXYZA’B’C’D’E’F’ ring system of MTX was constructed from the WXYZ and C’D’E’F’ rings by using the convergent method via two-rings construction useful for synthesizing ladder-shaped polyethers developed in our laboratory.

Academic Significance and Societal Importance of the Research Achievements

マイトトキシン(MTX)は,食中毒シガテラの原因物質のひとつであり,強力な細胞内へのCa2+流入活性を有する。本申請者は,MTXのように分子量が3000を超える巨大な分子の場合,「生物活性の発現には全構造が必須なのではなく,重要な部分構造が存在する」という仮説を立てた。これまでに様々なMTXの部分構造を合成し,特に疎水性の部分構造がMTXによって引き起こされるCa2+流入活性をより強く阻害することを明らかにした点は,学術的に意義がある。これらの阻害剤の探索は,食中毒シガテラの治療法や予防法の開発に繋がると考えられるため,社会的意義は大きい。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (36 results)

All 2019 2018 2017 2016 Other

All Journal Article (4 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 4 results,  Open Access: 2 results) Presentation (29 results) (of which Int'l Joint Research: 8 results,  Invited: 5 results) Remarks (3 results)

  • [Journal Article] Synthesis of 6/6/6-Tricyclic Ether System via Achmatowicz and Intramolecular Oxa-Michael Reactions2018

    • Author(s)
      Yamamoto, H.; Torikai, K.; Ebine, M.; Oishi, T.
    • Journal Title

      Heterocycles

      Volume: in press Issue: 1 Pages: 158-162

    • DOI

      10.3987/com-17-s(t)10

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Convergent Syntheses of the WXYZ Ring of Maitotoxin and the HIJK Ring of Brevisulcenal-F2018

    • Author(s)
      Osato Naoya、Onoue Hisaaki、Toma Yoshiki、Torikai Kohei、Ebine Makoto、Satake Masayuki、Oishi Tohru
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 3 Pages: 265-268

    • DOI

      10.1246/cl.171056

    • NAID

      130006434032

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Syntheses and Biological Activities of the LMNO, ent-LMNO, and NOPQR(S) Ring Systems of Maitotoxin2017

    • Author(s)
      Onoue Hisaaki、Marubayashi Riho、Ishikawa Erina、Konoki Keiichi、Torikai Kohei、Ebine Makoto、Murata Michio、Oishi Tohru
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 18 Pages: 9595-9618

    • DOI

      10.1021/acs.joc.7b01658

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of a Truncated Analog of Amphidinol 3 Corresponding to the C21-C39/C52-C67 Section2017

    • Author(s)
      Makoto Ebine, Yuri Takada, Naoto Yanai, and Tohru Oishi
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 5 Pages: 662-664

    • DOI

      10.1246/cl.160985

    • NAID

      130005655669

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] マイトトキシンのAB環部の合成研究2019

    • Author(s)
      吉村 庄太郎,鳥飼 浩平,海老根 真琴,大石 徹
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] マイトトキシンのDEFおよびGHI環部の統一的合成2019

    • Author(s)
      安冨 貴也,薬師寺 宏幸,鳥飼 浩平,海老根 真琴,大石 徹
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Structure Determination, Chemical Synthesis, and Evaluation of Biological Activity of Super Carbon Chain Natural Products2019

    • Author(s)
      Tohru Oishi
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] マイトトキシンのDEF環部の合成研究2018

    • Author(s)
      安冨 貴也,薬師寺 宏幸,鳥飼 浩平,海老根 真琴,大石 徹
    • Organizer
      創薬懇話会2018in志賀島
    • Related Report
      2018 Annual Research Report
  • [Presentation] マイトトキシンのDEF環部の合成研究2018

    • Author(s)
      安冨 貴也,薬師寺 宏幸,鳥飼 浩平,海老根 真琴,大石 徹
    • Organizer
      第55回化学関連支部合同九州大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] マイトトキシンのAB環部の合成研究2018

    • Author(s)
      吉村 庄太郎,鳥飼 浩平,海老根 真琴,大石 徹
    • Organizer
      第55回化学関連支部合同九州大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] マイトトキシンのDEF環部の合成研究2018

    • Author(s)
      安冨 貴也,薬師寺 宏幸,鳥飼 浩平,海老根真琴,大石 徹
    • Organizer
      第8回CSJフェスタ2018
    • Related Report
      2018 Annual Research Report
  • [Presentation] Structure-Activity Relationship Studies of Maitotoxin Based on the Chemical Synthesis of Partial Structures2018

    • Author(s)
      Tohru Oishi
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-14)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis of Partial Structures2018

    • Author(s)
      Tohru Oishi
    • Organizer
      ICAMS-1
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] マイトトキシンのDEF環部の合成研究2018

    • Author(s)
      安冨 貴也,薬師寺 宏幸,鳥飼 浩平,海老根 真琴,大石 徹
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis2018

    • Author(s)
      Hisaaki Onoue, Naoya Ohsato, Kohei Torikai, Makoto Ebine, Keiichi Konoki, Tohru Oishi
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] ブレビスルセナールFのHIJK環部の合成研究2017

    • Author(s)
      大里直哉,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] マイトトキシンのC’D’E’環部の合成研究2017

    • Author(s)
      山本大樹,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 連続した核間メチル基を有する6/7/6/6-四環性エーテルの収束的合成法2017

    • Author(s)
      大里直哉,當間佳樹,尾上久晃,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      第27回万有福岡シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 6/6/6/6/6-五環性梯子状ポリエーテルの新奇合成法の開発2017

    • Author(s)
      手嶋博也,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      第54回化学関連支部合同九州大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis of Partial Structures2017

    • Author(s)
      Tohru Oishi
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC 2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis of Partial Structures2017

    • Author(s)
      Tohru Oishi
    • Organizer
      第23回日本化学会九州支部・韓国化学会釜山支部合同セミナー
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis, Structure Determination, and Biological Activities of Marine Natural Products2017

    • Author(s)
      Tohru Oishi
    • Organizer
      Lecture in KAIST
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis of Partial Structures2017

    • Author(s)
      Tohru Oishi
    • Organizer
      120th KCS General Meeting & Exposition
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 化学合成に基づいたマイトトキシンの構造活性相関研究2017

    • Author(s)
      尾上久晃,石川絵理奈,丸林里帆,此木敬一,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Convergent Method for Synthesizing 6/7/6/6-Tetracyclic Ethers Possessing Contiguous Angular Methyl Groups2017

    • Author(s)
      Noaya Osato, Hisaaki Onoue, Yoshiki Toma, Kohei Torikai, Makoto Ebine and Tohru Oishi
    • Organizer
      ISONIS-11
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis of Partial Structures2016

    • Author(s)
      Tohru Oishi
    • Organizer
      ACP-2016-Korea
    • Place of Presentation
      KAIST,韓国
    • Year and Date
      2016-10-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] マイトトキシンのNOPQRS環部およびLMNO環部の合成と生物活性2016

    • Author(s)
      尾上久晃,石川絵理奈,丸林里帆,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      第51回天然物談話会
    • Place of Presentation
      湯沢東映ホテル
    • Year and Date
      2016-07-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] 梯子状ポリエーテル天然物の新奇二環構築型収束的合成法の開発2016

    • Author(s)
      大里直哉,當間佳樹,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      第51回天然物談話会
    • Place of Presentation
      湯沢東映ホテル
    • Year and Date
      2016-07-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] 梯子状ポリエーテルの新奇二環構築型収束的合成法の開発2016

    • Author(s)
      大里直哉,當間佳樹,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      第53回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Related Report
      2016 Annual Research Report
  • [Presentation] マイトトキシンのC’D’E’環部の合成研究2016

    • Author(s)
      山本大樹,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      第53回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Related Report
      2016 Annual Research Report
  • [Presentation] C-グリコピラノシドのフローマイクロ合成2016

    • Author(s)
      神徳瑞生,岸上隼大,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      第53回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Related Report
      2016 Annual Research Report
  • [Presentation] マイトトキシンのBCDおよびDEF環部の合成研究2016

    • Author(s)
      藥師寺宏幸,久保卓也,海老根真琴,鳥飼浩平,大石 徹
    • Organizer
      第53回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Related Report
      2016 Annual Research Report
  • [Presentation] 梯子状ポリエーテルの新奇二環構築型収束的合成法の開発2016

    • Author(s)
      大里直哉,當間佳樹,鳥飼浩平,海老根真琴,大石 徹
    • Organizer
      第28回若手研究者のためのセミナー
    • Place of Presentation
      九州大学伊都キャンパス
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Remarks] 九州大学理学部化学科生物有機化学研究室

    • URL

      http://www.scc.kyushu-u.ac.jp/Seibutsuyuki/index.html

    • Related Report
      2018 Annual Research Report
  • [Remarks]

    • URL

      http://www.scc.kyushu-u.ac.jp/Seibutsuyuki/index.htm

    • Related Report
      2017 Annual Research Report
  • [Remarks] 九州大学理学部化学科 生物有機化学研究室

    • URL

      http://www.scc.kyushu-u.ac.jp/Seibutsuyuki/index.htm

    • Related Report
      2016 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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