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Molecular mechanisms of toxin synthesis in paralytic shellfish toxin producing dinoflagellates

Research Project

Project/Area Number 15K07569
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Aquatic life science
Research InstitutionTohoku University

Principal Investigator

Cho Yuko  東北大学, 農学研究科, 助教 (60323086)

Co-Investigator(Kenkyū-buntansha) 日出間 志寿  東北大学, 農学研究科, 助教 (30241558)
Co-Investigator(Renkei-kenkyūsha) YAMASHITA MARI  東北大学, 大学院農学研究科, 教授 (50192430)
KONOKI KEIICHI  東北大学, 大学院農学研究科, 准教授 (40292825)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords生合成 / 麻痺性貝毒 / サキシトキシン / 免疫染色 / LC-MS / 発現解析 / 渦鞭毛藻 / 麻痺性貝毒生合成酵素 / 抗ペプチド抗体 / LC-MSMS / リアルタイムPCR / ELISA / LC-MS/MS / クローニング
Outline of Final Research Achievements

Saxitoxin and its analogues are potent neurotoxins which are named as paralytic shellfish toxins, collectively. The mechanism of their biosynthesis were investigated by the comparison of the toxic and non-toxic subclones of the dinoflagellate, Alexandrium tamarense. The analytical methods were developed for the expression analysis (the immunohistochemical method for the biosynthetic enzymes and the column switching HILIC-MS method for the biosynthetic intermediates). By these methods, the key steps toward the non-toxic mutation was suggested to be the first few steps in the complicated STX biosynthetic pathway. Moreover unexpectedly, the localization of the enzymes which catalize the first and the second step were suggested to be different. It leads us to the new hypothesis that there could be some unknown regulation mechanism other than the regulation of the protein expression.

Report

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

    (30 results)

All 2018 2017 2016 2015

All Journal Article (9 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 9 results,  Open Access: 3 results,  Acknowledgement Compliant: 4 results) Presentation (21 results) (of which Int'l Joint Research: 5 results)

  • [Journal Article] Spiro Bicyclic Guanidino Compounds from Pufferfish, Possible Biosynthetic Intermediates of Tetrodotoxin in Marine Environments2018

    • Author(s)
      Ueyama Nozomi、Sugimoto Keita、Kudo Yuta、Onodera Ken-ichi、Cho Yuko、Konoki Keiichi、Nishikawa Toshio、Yotsu-Yamashita Mari
    • Journal Title

      Chem. Eur. J.

      Volume: 印刷中 Issue: 28 Pages: 7250-7258

    • DOI

      10.1002/chem.201801006

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Six domoic acid related compounds from the red alga, Chondria armata, and domoic acid biosynthesis by the diatom, Pseudo-nitzschia multiseries2018

    • Author(s)
      Maeno Yukari、Kotaki Yuichi、Terada Ryuta、Cho Yuko、Konoki Keiichi、Yotsu-Yamashita Mari
    • Journal Title

      Sci. Rep.

      Volume: 8 Issue: 1 Pages: 356-356

    • DOI

      10.1038/s41598-017-18651-w

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Differential binding of tetrodotoxin and its derivatives to voltage-sensitive sodium channel subtypes (Nav1.1 to Nav1.7)2017

    • Author(s)
      Tsukamoto Tadaaki、Chiba Yukie、Wakamori Minoru、Yamada Tomoshi、Tsunogae Shunsuke、Cho Yuko、Sakakibara Ryo、Imazu Takuya、Tokoro Shouta、Satake Yoshiki、Adachi Masaatsu、Nishikawa Toshio、Yotsu-Yamashita Mari、Konoki Keiichi
    • Journal Title

      Br. J. Pharmacol.

      Volume: 174 Issue: 21 Pages: 3881-3892

    • DOI

      10.1111/bph.13985

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dietary administration of tetrodotoxin and its putative biosynthetic intermediates to the captive-reared non-toxic Japanese fire-bellied newt, Cynops pyrrhogaster2017

    • Author(s)
      Kudo Yuta、Chiba Chikafumi、Konoki Keiichi、Cho Yuko、Yotsu-Yamashita Mari
    • Journal Title

      Toxicon

      Volume: 137 Pages: 78-82

    • DOI

      10.1016/j.toxicon.2017.07.016

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Inhibition of veratridine-induced delayed inactivation of the voltage-sensitive sodium channel by synthetic analogs of crambescin B,2017

    • Author(s)
      Tadaaki Tsukamoto, Yukie Chiba, Atsuo Nakazaki, Yuki Ishikawa, Yoshiki Nakane, Yuko Cho, Mari Yotsu-Yamashita, Toshio Nishikawa, Minoru Wakamori, and Keiichi Konoki,*
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 27 Issue: 5 Pages: 1247-1251

    • DOI

      10.1016/j.bmcl.2017.01.054

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis and identification of key biosynthetic intermediates for formation of the tricyclic skeleton of saxitoxin2017

    • Author(s)
      Shigeki Tsuchiya, Yuko Cho, Renpei Yoshioka, Keiichi Konoki, Kazuo Nagasawa, Yasukatsu Oshima, and Mari Yotsu-Yamashita
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Issue: 19 Pages: 1-6

    • DOI

      10.1002/anie.201612461

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Column switching combined with hydrophilic interaction chromatography-tandem mass spectrometry for the analysis of saxitoxin analogues, and their biosynthetic intermediates in dinoflagellates2016

    • Author(s)
      Yuko Cho*, Shigeki Tsuchiya, Renpei Yoshioka, Takuo Omura, Keiichi Konoki, Yasukatsu Oshima, Mari Yotsu-Yamashita
    • Journal Title

      Journal of Chromatography A

      Volume: 1474 Pages: 109-120

    • DOI

      10.1016/j.chroma.2016.10.065

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Biosynthetic route towards saxitoxin and shunt pathway2016

    • Author(s)
      Shigeki Tsuchiya, Yuko Cho, Keiichi Konoki, Kazuo Nagasawa, Yasukatsu Oshima and Mari Yotsu-Yamashita
    • Journal Title

      Scientific Reports

      Volume: 6 Issue: 1 Pages: 20340-20340

    • DOI

      10.1038/srep20340

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] The presence of 12β-deoxydecarbamoylsaxitoxin in the Japanese toxic dinoflagellate Alexandrium determined by simultaneous analysis for paralytic shellfish toxins using HILIC-LC-MS/MS2015

    • Author(s)
      Yuko Cho*, Shigeki Tsuchiya, Renpei Yoshioka, Takuo Omura, Keiichi Konoki, Yasukatsu Oshima and Mari Yotsu-Yamashita
    • Journal Title

      Harmful Algae

      Volume: 49 Pages: 58-67

    • DOI

      10.1016/j.hal.2015.09.003

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 15N同位体標識培地による渦鞭毛藻の麻痺性貝毒及び生合成中間体への15N取り込み挙動の解析2018

    • Author(s)
      長 由扶子、土屋 成輝、此木 敬一、大島 泰克、山下 まり
    • Organizer
      平成30年度公益社団法人日本水産学会春季大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] クロイソカイメン共生菌が生産する新規有毒二次代謝産物の構造決定2018

    • Author(s)
      菊池 颯、岡田 華弥、長 由扶子、吉田 慎一朗、權 垠相、山下 まり、此木 敬一
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 記憶喪失性貝毒ドウモイ酸の生合成経路に関する研究2018

    • Author(s)
      前野 優香理、小瀧 裕一、長 由扶子、此木 敬一、山下 まり
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 海洋生物における新規テトロドトキシン関連化合物の探索2018

    • Author(s)
      上山 望、杉本 敬太、長 由扶子、此木 敬一、山下 まり
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 巨大ゲノム生物の毒生合成マシナリー探索とゲノム解析の基盤技術開発2018

    • Author(s)
      長 由扶子
    • Organizer
      科学研究費補助金 新学術領域研究(研究領域提案型)生物合成系の再設計による複雑骨格機能分子の革新的創成科学、第3回公開シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 渦鞭毛藻有毒、無毒種の STX 生合成中間体定量と推定 STX 生合成酵素 SxtA4 の発現解析2017

    • Author(s)
      長 由扶子・土屋成輝・日出間志寿・大村卓朗・ 小池一彦・及川 寛・ 此木敬一・大島泰克・山下まり
    • Organizer
      平成29年度公益社団法人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
      2017-03-26
    • Related Report
      2016 Research-status Report
  • [Presentation] 渦鞭毛藻の麻痺性貝毒及び生合成中間体のカラムスイッチング HILIC-HILIC-MS-MRMによる分析2017

    • Author(s)
      長 由扶子、土屋 成輝、吉岡 廉平、大村 卓朗、此木 敬一、大島 泰克、山下 まり
    • Organizer
      日本農芸化学会2017年度大会
    • Place of Presentation
      京都女子大学(京都府京都市)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] フグ由来のテトロドトキシン関連化合物の合成2017

    • Author(s)
      杉本 敬太 、上山 望 、長 由扶子 、此木 敬一 、西川 俊夫 、山下 まり
    • Organizer
      日本農芸化学会東北支部第152回大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ”Biosynthetic pathway of saxitoxin based on the structures of its intermediate2017

    • Author(s)
      Mari Yotsu-Yamashita, Shigeki Tsuchiya, Yuko Cho, Keiichi Konoki, and Yasukatsu Oshima
    • Organizer
      The JSFS 85th Anniversary-Commemorative International Symposium
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] フグの新規スピロ環状グアニジノ化合物の単離、構造決定と海産テトロドトキシンの生合成経路の推定2017

    • Author(s)
      上山望, 杉本敬太, 工藤雄大, 長 由扶子, 此木敬一, 西川俊夫, 山下まり
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Screening of novel toxic secondary metabolites from symbiotic bacteria of the marine sponge Halichondria okadai2017

    • Author(s)
      Sou Kikuchi, Kayo Okada, Yuko Cho, Mari Yotsu-Yamashita, Keiichi Konoki
    • Organizer
      Tohoku University's Chemistry Summer School
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Screening of biosynthetic intermediates of domoic acid2017

    • Author(s)
      Yukari Ebine, Yuichi Kotaki, Ryuta Terada, Yuko Cho, Keiichi Konoki and Mari Yotsu-Yamashita
    • Organizer
      Tohoku University's Chemistry Summer School
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 巨大ゲノム生物の毒生合成マシナリー探索とゲノム解析の基盤技術開発2017

    • Author(s)
      長 由扶子
    • Organizer
      新学術領域研究(研究領域提案型)生物合成系の再設計による複雑骨格機能分子の革新的創成科学、第2回公開シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 電位依存性Na+チャネルに対するCrambescin B誘導体の阻害活性2017

    • Author(s)
      塚本匡顕、千葉雪絵、中崎敦夫、石川裕生、中根嘉祈、長 由扶子、西川俊夫、山下まり、此木敬一
    • Organizer
      第12回化学生態学研究会
    • Related Report
      2017 Annual Research Report
  • [Presentation] フグのテトロドトキシン関連化合物の構造と推定生合成経路2017

    • Author(s)
      上山望、杉本敬太、西川俊夫、長 由扶子、此木敬一、山下まり
    • Organizer
      第28回万有仙台シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Column switching HILIC-MS for the analysis of saxitoxin analogues and their biosynthetic intermediates in toxic and non-toxic dinoflagellates2017

    • Author(s)
      Yuko Cho, Shigeki Tsuchiya, Takuo Omura, Kazuhiko Koike, Hiroshi Oikawa, Keiichi Konoki, Yasukatsu Oshima and Mari Yotsu-Yamashita
    • Organizer
      Gordon Conference (Mycotoxins & Phycotoxins)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 麻痺性貝毒生合成中間体の同定と生合成経路の解明2016

    • Author(s)
      土屋成輝・長由扶子・吉岡廉平・美野輪高之・此木敬一・長澤和夫・大島泰克・山下まり
    • Organizer
      第58回天然有機化合物討論会
    • Place of Presentation
      東北大学理学研究科(仙台市青葉区)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 渦鞭毛藻Alexandrium tamarense有毒、無毒株比較研究 推定STX生合成酵素SxtAの免疫化学的手法によるタンパク発現解析2016

    • Author(s)
      長 由扶子、日出間志寿、土屋成輝、此木敬一、大島泰克、山下まり
    • Organizer
      平成28年度日本水産学会春季大会
    • Place of Presentation
      東京海洋大学、(東京都品川区)
    • Year and Date
      2016-03-29
    • Related Report
      2015 Research-status Report
  • [Presentation] Screening of the biosynthetic intermediates of paralytic shellfish toxins using a stable isotope-labeled precursors2016

    • Author(s)
      Shigeki Tsuchiya, Yuko Cho, Keiichi Konoki, and Mari Yotsu-Yamashita
    • Organizer
      Tohoku University's Chemistry Summer School
    • Place of Presentation
      東北大学理学研究科(仙台市青葉区)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 麻痺性貝毒の生合成経路解明に向けた予想生合成中間体の合成及び同定2016

    • Author(s)
      土屋成輝、吉岡廉平、長由扶子、此木敬一、長澤和夫、大島泰克、山下まり
    • Organizer
      日本農芸化学会東北支部第151回大会
    • Place of Presentation
      山形大学農学部(山形県、鶴岡市)
    • Related Report
      2016 Research-status Report
  • [Presentation] The simultaneous analysis of saxitoxin analogues and their biosynthetic intermediates by HILIC-LC-MS/MS2015

    • Author(s)
      Yuko Cho, Renpei Yoshioka, Shigeki Tsuchiya, Keiichi Konoki, Yasukatsu Oshima and Mari Yotsu-Yamashita
    • Organizer
      環太平洋国際化学会議
    • Place of Presentation
      ホノルル、ハワイ、米国
    • Year and Date
      2015-12-17
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2019-03-29  

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