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Exploration of biosynthetic enzymes of marine cyclic ethers in dinoflagellates

Research Project

Project/Area Number 15K01798
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Biomolecular chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

Satake Masayuki  東京大学, 大学院理学系研究科(理学部), 准教授 (90261495)

Project Period (FY) 2015-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Keywords環状エーテル / 生合成酵素 / 海洋微細藻 / エポキシド開環反応 / 6員環エーテル / 渦鞭毛藻 / 梯子状ポリエーテル / 酵素反応 / 脱水素反応 / ポリ環状エーテル / 環化酵素 / 生合成
Outline of Final Research Achievements

Ladder-shaped polyethers (LSPs) are secondary metabolites produced by marine dinoflagellates and have unique structures and strong bioactivities. The biosynthesis of LSPs has been proposed. However, the fused ether ring formation of marine LSPs has not yet been elucidated because of a lack of genetic information of dinoflagellates and the complexity of these structures.
For exploration of biosynthetic enzymes such as epoxidase and an epoxide-opening enzyme, model precursor compounds were synthesized. Incubation of the model compounds with dinoflagellate extracts gave rise to a 6-membered ether ring products. These results strongly indicated that the epoxide-opening enzyme was found in the extract from dinoflagellates.

Academic Significance and Societal Importance of the Research Achievements

渦鞭毛藻が生産する環状エーテル化合物の生合成酵素の発見は、これまで不明であった海産天然物の生合成機構の詳細を明らかとした。本酵素の利用により、環状エーテル化合物の合成が有機試薬、溶媒の使用無く行えることになる。有機溶媒を使用しないため、製品の安全性が向上し、今後、医薬品や化学品への応用が可能となる。また、酵素阻害剤の開発により有毒物質生産制御につながり、赤潮被害や海産食中毒予防が可能となり、公衆衛生および水産業保護にも貢献する。

Report

(5 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (17 results)

All 2019 2018 2017 2016 2015 Other

All Int'l Joint Research (3 results) Journal Article (5 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 5 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (9 results) (of which Int'l Joint Research: 2 results,  Invited: 1 results)

  • [Int'l Joint Research] コースロン研究所(ニュージーランド)

    • Related Report
      2017 Research-status Report
  • [Int'l Joint Research] コースロン研究所(ニュージーランド)

    • Related Report
      2016 Research-status Report
  • [Int'l Joint Research] コースロン研究所(ニュージーランド)

    • Related Report
      2015 Research-status Report
  • [Journal Article] New aplysiatoxin derivatives from the Okinawan cyanobacterium Moorea producens2019

    • Author(s)
      H. Nagai, M. Watanabe, S. Sato, M. Kawaguchi, Y. Y. Xiao, K. Hayashi, R. Watanabe, H. Uchida , M. Satake
    • Journal Title

      Tetrahedron

      Volume: 75 Issue: 17 Pages: 2486-2494

    • DOI

      10.1016/j.tet.2019.03.020

    • 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
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Brevisulcenal-G, -H, and -I, Polycyclic Ether Marine Toxins from the Dinoflagellate Karenia brevisulcata2018

    • Author(s)
      M. Satake, R. Irie, Y. Hamamoto, K. Tachibana, P. T. Holland, D. T. Harwood, F. Shi, V. Beuzenberg, Y. Itoh, F. Hayashi, H. Zhang
    • Journal Title

      Heterocycles

      Volume: 96 Issue: 12 Pages: 2096-2105

    • DOI

      10.3987/com-18-14014

    • NAID

      40021835835

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure-Activity Relationships2017

    • Author(s)
      M. Satake, K. Cornelio, S. Hanashima, R. Malabed, M. Murata, N. Matsumori, H. Zhang, F. Hayashi, S. Mori, J. S. Kim, C.-H. Kim, J.-S. Lee
    • Journal Title

      Journal of Natural Products

      Volume: 80 Issue: 11 Pages: 2883-2888

    • DOI

      10.1021/acs.jnatprod.7b00345

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Brevisulcatic acids from a marine microalgae implicated in a toxic vent in New Zealand2016

    • Author(s)
      R. Irie, R. Suzuki, K. Tachibana, P. T. Holland, D. T. Harwood, F. Shi, P. McNabb, V.Beuzenberg, F. Hayashi, H. Zhang, M. Satake
    • Journal Title

      Heterocycles

      Volume: 92 Issue: 1 Pages: 45-54

    • DOI

      10.3987/com-15-13332

    • Related Report
      2016 Research-status Report 2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] ブレビスルセナール-FのRS環部の合成研究2019

    • Author(s)
      新井智之・鳥飼浩平・海老根真琴・佐竹真幸・大石徹
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthetic Study of the VWX Ring System of Brevisulcenal-F2019

    • Author(s)
      TANAKA, Tatsuya; TORIKAI, Kohei; EBINE, Makoto; SATAKE, Masayuki; OISHI, Tohru
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] アミロイドペプチドへの結合モチーフとしての各種梯子状ポリエーテル化合物の評価と相互作用についての考察2019

    • Author(s)
      Xiong Weiqi・土川博史・原利明・村田道雄・佐竹真幸
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Biosynthetic enzymes related to marine polyethers in dinoflagellate extracts2018

    • Author(s)
      Masayuki Satake, Daisuke Naganuma
    • Organizer
      The 18th international conference on harmful algae
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 梯子状ポリエーテル化合物のアミロイドβ凝集阻害活性および相互作用の評価2018

    • Author(s)
      Xiong Weigi、原利明、土川博、村田道雄、佐竹真幸
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] ブレビスルセナールーFのVWX環部の合成研究2018

    • Author(s)
      田中達也、鳥飼浩平、海老根真琴、佐竹真幸、大石徹
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 沖縄産ラン藻より得られたアプリシアトキシン類の構造と生物活性2017

    • Author(s)
      渡辺陽光・金山卓郎・江 偉娜・ 内田 肇・渡邊龍一・鈴木敏之・佐竹真幸・永井宏史
    • Organizer
      平成29年度日本水産学会春季大会
    • Place of Presentation
      東京海洋大学(東京都 港区)
    • Year and Date
      2017-03-28
    • Related Report
      2016 Research-status Report
  • [Presentation] Exploration of biosynthetic enzymes of marine polyethers in dinoflagellates2017

    • Author(s)
      Masayuki Satake, Daisuke Naganuma, Takahisa Genji
    • Organizer
      The International Symposium Fisheries Science for Future Generations
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Interaction between transmembrane model peptides and ladder shaped polycyclic ethers2015

    • Author(s)
      K. Yamada, M. Satake, S. Fukuzawa, K. Tachibana, T. Hara, M. Murata
    • Organizer
      環太平洋国際化学会議
    • Place of Presentation
      米国ハワイ
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2020-03-30  

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