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Structure and detection of toxins from dinoflagellate

Research Project

Project/Area Number 22404006
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section海外学術
Research Field Living organism molecular science
Research InstitutionThe University of Tokyo

Principal Investigator

SATAKE Masayuki  東京大学, 理学(系)研究科(研究院), 准教授 (90261495)

Project Period (FY) 2010-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥15,600,000 (Direct Cost: ¥12,000,000、Indirect Cost: ¥3,600,000)
Fiscal Year 2013: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2012: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2011: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2010: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Keywords構造決定 / 定量法開発 / ポリエーテル化合物 / 渦鞭毛藻 / 神経毒 / 細胞毒 / 構造解析 / 細胞毒性 / NMR / 赤潮 / マウス致死毒性 / ポリオキシ化合物 / NMRスペクトル
Outline of Final Research Achievements

A red tide occurred in New Zealand. This caused mass mortalities of fish within the harbour. Over 500 cases of human respiratory distress were also reported, with symptoms including a dry cough, severe sore throat, and headache. A cell extract of the causataive dinoflagellate showed strong mouse lethality and cytotoxicity.
From the neutral lipophilic fraction five novel toxins were identified. Isolation was guided by cytotoxicity against mouse leukemia P388 cells. The sodiated cations of toxins in MALDI mass spectra were observed at over m/z 2000. The most abundant toxin was determined to be a large polycyclic ether compound with 24 ether rings, including dihydrofuran, 13 hydroxy groups, and a 2-methylbut-2-enal side chain. From the hydrophilic acidic fraction another novel set of toxins were identified. The toxins consist of nine contiguous ether rings and contain a 9-membered ether ring within the central portion of the molecule. Toxins showed cytotoxicity against neuro2A cells.

Report

(5 results)
  • 2014 Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (26 results)

All 2014 2013 2011 2010 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 3 results) Presentation (19 results) (of which Invited: 2 results)

  • [Journal Article] A sensitive LC-MS/MS assay for brevisulcenal and brevisulcatic acid toxins produced by the dinoflagellate Karenia brevisulcata2014

    • Author(s)
      D. T. Harwood, F. Shi, M. Satake, P. T. Holland
    • Journal Title

      Toxicon

      Volume: 84 Pages: 19-27

    • DOI

      10.1016/j.toxicon.2014.03.004

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Brevisulcatic acids, marine ladder-frame polyethers from the red tide dinoflagellate Karenia brevisulcata in New Zealand2014

    • Author(s)
      R. Suzuki, R. Irie, Y. Harntaweesup, K. Tachibana, P. T. Holland, D. T. Harwood, F. Shi, V. Beuzenberg, Y. Itoh, S. Pascal, P. J. B. Edwards, M. Satake
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 22 Pages: 5850-5853

    • DOI

      10.1021/ol502700h

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Gymnocin-A carboxylic acid and Gymnocin-A2, new cytotoxic polyethers from the red tide dinoflagellate, Karenia mikimotoi2013

    • Author(s)
      Y. Tanaka, M. Satake, M. Yotsu-Yamashita, Y. Oshima
    • Journal Title

      Heterocycles

      Volume: 87 Issue: 10 Pages: 2037-2046

    • DOI

      10.3987/com-12-12814

    • Related Report
      2013 Annual Research Report 2012 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Gambieroxide, a novel epoxy polyether compound from the dinoflagellate Gambierdiscus toxicus GTP2 strain.2013

    • Author(s)
      R. Watanabe
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 48 Pages: 10299-10303

    • DOI

      10.1016/j.tet.2013.10.022

    • Related Report
      2013 Annual Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Complete 13C-labeling pattern of yessotoxin a marine ladder-frame polyether2011

    • Author(s)
      Masatoshi Yamazaki
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 5 Pages: 877-880

    • DOI

      10.1016/j.tet.2010.12.015

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of (-)-brevisin: a concise synthesis of a new marine polycyclic ether.2011

    • Author(s)
      Takefumi Kuranaga
    • Journal Title

      Organic Letters

      Volume: 13 Issue: 4 Pages: 696-699

    • DOI

      10.1021/ol102925d

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Prorocentrol, a polyoxy linear carbon chain compound isolated from the toxic dinoflagellate, Prorocentrum hoffmannianum.2011

    • Author(s)
      Kohtaro Sugahara
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 76 Issue: 9 Pages: 3131-3138

    • DOI

      10.1021/jo102585k

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] Novel toxins from the New Zealand red tide dinoflagellate Karenia brevisulcata2014

    • Author(s)
      M. Satake, Y. Hamamoto, R. Suzuki, R. Irie, P. Holland, T. Harwood, P. McNabb, F. Shi, V. Veuzenberg
    • Organizer
      The 16th International Conference on Harmful Algae
    • Place of Presentation
      Wellington (New Zealand)
    • Year and Date
      2014-10-27 – 2014-10-31
    • Related Report
      2013 Annual Research Report
  • [Presentation] ニュージーランド赤潮渦鞭毛藻が生産する梯子状ポリエーテル化合物の単離と2014

    • Author(s)
      入江樂、鈴木里菜、佐竹真幸、橘和夫、Tim Harwood、Patrick Holland、伊藤喜之
    • Organizer
      第56回天然有機化合物討論会
    • Place of Presentation
      高知県民会館
    • Year and Date
      2014-10-15
    • Related Report
      2013 Annual Research Report
  • [Presentation] ニュージーランド産有毒渦鞭毛藻の生産する新規水溶性化合物の構造解析2014

    • Author(s)
      鈴木里菜、佐竹真幸、橘和夫、HARWOOD T.、HOLLAND P.、BEUZENBERG V.、SHI F.
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-29
    • Related Report
      2013 Annual Research Report
  • [Presentation] ニュージーランドの赤潮有毒渦鞭毛藻が生産するポリ環状エーテル化合物の単離と構造解析2014

    • Author(s)
      入江樂、佐竹真幸、橘和夫、HARWOOD T.、HOLLAND P.
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-29
    • Related Report
      2013 Annual Research Report
  • [Presentation] 抗珪藻マクロライド化合物の合成研究2013

    • Author(s)
      水上篤志
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 合成的手法による梯子状ポリエーテルKBT-Fの構造解明2013

    • Author(s)
      佐々木幸治
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] ニュージーランド産赤潮渦鞭毛藻の生産する新規水溶性化合物の単離と性状2013

    • Author(s)
      鈴木里奈
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] ニュージーランド産赤潮渦鞭毛藻由来新規ポリ環状エーテル化合物の構造解析2011

    • Author(s)
      濱本友佳(佐竹真幸)
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川県)
    • Year and Date
      2011-03-23
    • Related Report
      2010 Annual Research Report
  • [Presentation] 構造解明を目的とした新規海産ポリ環状エーテルBSX-1推定部分構造の合成2011

    • Author(s)
      堤亮祐(佐竹真幸)
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川県)
    • Year and Date
      2011-03-23
    • Related Report
      2010 Annual Research Report
  • [Presentation] NMR法を用いた付着性渦鞭毛藻由来ポリエンポリオール化合物プロロセントロールの立体構造研究2011

    • Author(s)
      菅原孝太郎(佐竹真幸)
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川県)
    • Year and Date
      2011-03-23
    • Related Report
      2010 Annual Research Report
  • [Presentation] ニュージーランド産赤潮渦鞭毛藻の生産する新規有毒成分の単離と性状2010

    • Author(s)
      佐竹真幸
    • Organizer
      第57回トキシンシンポジウム
    • Place of Presentation
      長浜グランドホテル(滋賀県)
    • Year and Date
      2010-07-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] ニュージーランドで大規模赤潮被害をもたらした新規ポリ環状エーテル化合物の構造解析

    • Author(s)
      濱本友佳
    • Organizer
      新規素材探索研究会第10回セミナー
    • Place of Presentation
      新横浜ビューホテル(神奈川県)
    • Related Report
      2011 Annual Research Report
  • [Presentation] オカダ酸産生渦鞭毛藻由来ポリエンポリオール化合物prorocentrolの立体構造解析

    • Author(s)
      菅原孝太郎
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際センター(大阪府)
    • Related Report
      2011 Annual Research Report
  • [Presentation] ニュージーランドで発生した渦鞭毛藻が生産する巨大ポリ環状エーテル化合物の構造決定

    • Author(s)
      濱本友佳
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際センター(大阪府)
    • Related Report
      2011 Annual Research Report
  • [Presentation] 海産梯子状ポリエーテル化合物yessotoxinの生合成解明

    • Author(s)
      山崎正稔
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際センター(大阪府)
    • Related Report
      2011 Annual Research Report
  • [Presentation] Marine Toxins in New Zealand

    • Author(s)
      Masayuki Satake
    • Organizer
      NZ Institute of Chemistry Conference
    • Place of Presentation
      Hamilton (New Zealand)
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Structures of new polycyclic ether toxins from the red tide dinoflagellate Karenia brevisulcata in New Zealand.

    • Author(s)
      Yuka Hamamoto
    • Organizer
      NZ Institute of Chemistry Conference
    • Place of Presentation
      Hamilton (New Zealand)
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] ニュージーランドの赤潮渦鞭毛藻被害に関わる巨大ポリ環状エーテル化合物群の構造決定

    • Author(s)
      濱本友佳
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県)
    • Related Report
      2011 Annual Research Report
  • [Presentation] 合成的手法によるポリ環状エーテル、赤潮毒KBT-Fの構造解明

    • Author(s)
      佐々木幸治
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県)
    • Related Report
      2011 Annual Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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