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Elucidation of the biosynthetic pathways of tetrodotoxin and saxitoxin based on the intermediates

Research Project

Project/Area Number 17H03809
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

Yamashita Mari  東北大学, 農学研究科, 教授 (50192430)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥17,290,000 (Direct Cost: ¥13,300,000、Indirect Cost: ¥3,990,000)
Fiscal Year 2019: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2017: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Keywordsテトロドトキシン / サキシトキシン / 生合成 / 中間体 / 構造決定 / LC/MS
Outline of Final Research Achievements

Seven novel bicyclic guanidino compounds were isolated from the tetrodotoxin (TTX) possessing pufferfish, and their structures were elucidated. These compounds have the same relative stereochemistry as that of TTX. Based on their structures, oxidative biosynthetic pathway towards TTX was suggested. For biosynthesis of saxitoxin (STX), predicted intermediates, 11-hydroxy Int-C’2 and Int-E’were chemically synthesized. They were identified in toxin producing dinoflagellate and cyanobacterium using HR-LC/MS. In addition, a new STX analogue, 12beta-deoxyGTX3 was identified in the toxic cyanobacterium using the standard which was prepared by chemical derivatization.

Academic Significance and Societal Importance of the Research Achievements

フグ毒として知られるテトロドトキシン(TTX)は、最もよく知られた生物毒の一つであるが、その生合成機構は解明されていない。最近ではヨーロッパなどで食用の二枚貝などからもTTXが検出され、食品衛生上、その生合成機構を解明することは社会的にも重要である。また、麻痺性貝毒は近年猛威を振るっており、その代表的な毒素であるサキシトキシンの生合成は、世界各地で活発に研究されおり、その特異な三環性の化学構造から、生合成経路の解明は学術的にも注目を集めている。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (95 results)

All 2020 2019 2018 2017 Other

All Int'l Joint Research (4 results) Journal Article (27 results) (of which Int'l Joint Research: 9 results,  Peer Reviewed: 26 results,  Open Access: 8 results,  Acknowledgement Compliant: 2 results) Presentation (61 results) (of which Int'l Joint Research: 11 results,  Invited: 12 results) Book (1 results) Remarks (2 results)

  • [Int'l Joint Research] フランクフルト大学(ドイツ)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] ユタ州立大学(米国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] フランクフルト大学(ドイツ)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] フランクフルト大学(ドイツ)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Synthesis of C12-keto saxitoxin derivatives with unusual inhibitory activity against voltage‐gated sodium channels.2020

    • Author(s)
      Adachi, K., Yamada, T., Ishizuka, H., Oki, M., Tsunogae, S., Shimada, N., Chiba, O., Orihara, T., Hidaka, M., Hirokawa, T., Odagi, M., Konoki, K., Yotsu-Yamashita, M., Nagasawa, K.
    • Journal Title

      Chem. Eur. J.

      Volume: 26 Issue: 9 Pages: 2025-2033

    • DOI

      10.1002/chem.201904184

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Revisited - Failure of tetrodotoxin to protect red-spotted newts, Notophthalmus viridescens, from endoparasites2020

    • Author(s)
      Dietrich Mebs *, Mari Yotsu-Yamashita, Katharina Hartmann , Christine Elbert ,Richard Zehner, Stefan W. Toennes
    • Journal Title

      Toxicon

      Volume: 178 Pages: 77-81

    • DOI

      10.1016/j.toxicon.2020.02.026

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] セミナー室 / 農芸化学の中での化学生態学研究-その発展と展望- 生物が作り出す毒 どくどくしくない毒のはなし2020

    • Author(s)
      山下 まり, 此木 敬一, 稲垣 英利, 森 直樹, 森 哲
    • Journal Title

      化学と生物

      Volume: 58 Pages: 111-119

    • Related Report
      2019 Annual Research Report
  • [Journal Article] Total Syntheses and Determination of Absolute Configurations of Cep-212 and Cep-210, Predicted Biosynthetic Intermediates of Tetrodotoxin Isolated from Toxic Newt.2019

    • Author(s)
      Masaatsu Adachi,Tadachika Miyasaka, Yuta Kudo, Keita Sugimoto, Mari Yotsu-Yamashita, Toshio Nishikawa.
    • Journal Title

      Org. Lett.

      Volume: 21 Issue: 3 Pages: 780-784

    • DOI

      10.1021/acs.orglett.8b04043

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Metabolomic study of saxitoxin analogues and biosynthetic intermediates in dinoflagellates using 15N-labelled sodium nitrate as a nitrogen source2019

    • Author(s)
      1.Cho, Y., Tsuchiya, S., Omura, T., Koike, K., Oikawa, H., Konoki, K., Oshima, Y., Yotsu-Yamashita, M.
    • Journal Title

      Sci. Rep.

      Volume: 9 Issue: 1 Pages: 3460-3460

    • DOI

      10.1038/s41598-019-39708-y

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Quantitation of Tetrodotoxin and Its Analogues with a Combination of Liquid Chromatography-Tandem Mass Spectrometry and Quantitative 1H_NMR Spectroscopy2019

    • Author(s)
      Ryuichi Watanabe, Masato Tanioka, Hajime Uchida, Ryoji Matsushima, Hiroshi Oikawa,Masahiro Matsumiya, Mari Yotsu-Yamashita, and Toshiyuki Suzuki*
    • Journal Title

      J. Agric. Food Chem.

      Volume: 67 Issue: 46 Pages: 12911-12917

    • DOI

      10.1021/acs.jafc.9b06380

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Temporal Variation of the Profile and Concentrations of Paralytic Shellfish Toxins and Tetrodotoxin in the Scallop, Patinopecten yessoensis, Cultured in a Bay of East Japan2019

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

      Marine Drugs

      Volume: 17 Issue: 12 Pages: 653-653

    • DOI

      10.3390/md17120653

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Identification of a Novel Saxitoxin Analogue, 12β-Deoxygonyautoxin 3, in the Cyanobacterium, Anabaena circinalis (TA04)2019

    • Author(s)
      Minowa T.、Cho Y.、Oshima Y. 、Konoki K.、Yotsu-Yamashita M.
    • Journal Title

      Toxins

      Volume: 11 Issue: 9 Pages: 539-539

    • DOI

      10.3390/toxins11090539

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Possible Biosynthetic Products and Metabolites of Kainic Acid from the Red Alga Digenea simplex and Their Biological Activity2019

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

      Journal of Natural Products

      Volume: 82 Issue: 6 Pages: 1627-1633

    • DOI

      10.1021/acs.jnatprod.9b00128

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Isolation and biological activity of 8-epitetrodotoxin and the structure of a possible biosynthetic shunt product of tetrodotoxin, Cep-226A, from the newt, Cynops ensicauda popei2019

    • Author(s)
      Yuta Kudo and Mari Yotsu-Yamashita*
    • Journal Title

      Journal of Natural Products

      Volume: 82 Issue: 6 Pages: 1656-1663

    • DOI

      10.1021/acs.jnatprod.9b00178

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tetrodotoxin content of Rough-skinned Newts, Taricha granulosa (Salamandridae), from their northern distribution range, British Columbia, Canada, and Southeast-Alaska, USA2019

    • Author(s)
      Dietrich Mebs*, Mari Yotsu-Yamashita, Stefan W. Toennes
    • Journal Title

      Salamandra ISSN 0036-3375

      Volume: 55 Pages: 82-88

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A novel compound, “FA-1” isolated from Prunus mume, protects human bronchial epithelial cells and keratinocytes from cigarette Smoke extract-induced damage.2018

    • Author(s)
      Andrew J. Jang, Ji-Hyeok Lee, Mari Yotsu-Yamashita, Joodong Park, Steve Kye, Raymond L. Benza, Michael J. Passineau, You-Jin Jeon, Toru Nyunoya.
    • Journal Title

      Sci. Rep.

      Volume: 8 Issue: 1 Pages: 11504-11504

    • DOI

      10.1038/s41598-018-29701-2

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Lack of alkaloids and tetrodotoxin in the neotropical frogs Allobates spp. (Aromobatidae) and Silverstoneia flotator (Dendrobatidae).2018

    • Author(s)
      Dietrich Mebs, Mari Yotsu-Yamashita, Werner Pogoda, Joseph Vargas Alvarez, Raffael Ernst, Gunther Kohler, Stefan W. Toennes.
    • Journal Title

      Toxicon

      Volume: 152 Pages: 103-105

    • DOI

      10.1016/j.toxicon.2018.07.027

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Pufferfish Saxitoxin and Tetrodotoxin Binding Protein (PSTBP) Analogues in the Blood Plasma of the Pufferfish Arothron nigropunctatus, A. hispidus, A. manilensis, and Chelonodon patoca2018

    • Author(s)
      2.Yotsu-Yamashita, M., Nagaoka, Y., Muramoto, K., Cho, Y., Konoki, K.
    • Journal Title

      Mar. Drugs

      Volume: 16 Issue: 7 Pages: 224-224

    • DOI

      10.3390/md16070224

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Isolation and structure determination of lysiformine from bacteria associated with marine sponge Halichondria okadai2018

    • Author(s)
      3.Kikuchi, S., Okada, K., Cho, Y., Yoshida, S., Kwon, E., Yotsu-Yamashita, M., *Konoki, K.
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 27 Pages: 3742-3747

    • DOI

      10.1016/j.tet.2018.05.049

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Geographic range expansion of tetrodotoxin in amphibians ? First record in Atelopus hoogmoedi from the Guiana Shield2018

    • Author(s)
      Mebs Dietrich*、Lorentz Max、Yotsu-Yamashita Mari、Roler Daniela C.、Ernst Raffael、L?tters Stefan
    • Journal Title

      Toxicon

      Volume: 150 Pages: 175-179

    • DOI

      10.1016/j.toxicon.2018.05.011

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [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
      2018 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
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] A new sarasinoside congener, sarasinoside M2, from a marine sponge collected in the Solomon Islands2017

    • Author(s)
      Clyde Gorapava Puilingi, Yuta Kudo, Yuko Cho, Keiichi Konoki, and Mari Yotsu-Yamashita*
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 81 Issue: 2 Pages: 222-225

    • DOI

      10.1080/09168451.2016.1246172

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [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
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tetrodotoxin in Asian newts (Salamandridae)2017

    • Author(s)
      Yotsu-Yamashita, M., Toennes, S.W., Mebs, D.
    • Journal Title

      Toxicon

      Volume: 134 Pages: 14-17

    • DOI

      10.1016/j.toxicon.2017.05.014

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [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] 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] Total Synthesis of Polycavernosides A and B, Two Lethal Toxins from Red Alga.2017

    • Author(s)
      Kotaro Iwasaki, Satori Sasaki, Yusuke Kasai, Yuki Kawashima, Shohei Sasaki, Takanori Ito, Mari Yotsu-Yamashita, Makoto Sasaki.
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 24 Pages: 13201-13219

    • DOI

      10.1021/acs.joc.7b02293

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 貝毒,魚毒,腔腸動物の毒 神経毒とNeuroscience 20172017

    • Author(s)
      山下まり,此木敬一
    • Journal Title

      臨床神経科学,Clinical Neuroscience

      Volume: 35 Pages: 1443-1448

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Taricha granulosa (Rough-Skinned Newt) Predation2017

    • Author(s)
      Dietrich Mebs* and Mari Yotsu-Yamashita
    • Journal Title

      Herpetological Review

      Volume: 48 Pages: 828-829

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] サキシトキシン類の非天然型エナンチオマーの合成及びナトリウムチャネル阻害活性評価2020

    • Author(s)
      ◯高柳優夏*、安達栞菜、石塚 颯、此木敬一、山下まり、小田木 陽、長澤和夫
    • Organizer
      日本化学会 第100春季年会 (2020)
    • Related Report
      2019 Annual Research Report
  • [Presentation] フグ由来の新規テトロドトキシン関連化合物の単離と構造2020

    • Author(s)
      八重樫優士*、工藤雄大、長由扶子、此木敬一、山下まり
    • Organizer
      日本農芸化学会 2020 大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 麻痺性貝毒サキシトキシンの推定生合成中間体の合成と有毒生物中の分析2020

    • Author(s)
      ○東海林 千容*、長 由扶子、赤松 みちる、安達 栞菜、石塚 颯、此木 敬一、長澤 和夫、山下 まり
    • Organizer
      日本農芸化学会2020年度大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 有毒イモリより得られたN-hydroxy型テトロドトキシン類縁体の構造解析2020

    • Author(s)
      ○工藤 雄大*、ハニフィン チャールス、小瀧 裕一、山下 まり
    • Organizer
      日本農芸化学会2020年度大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] コルヒチン存在下の渦鞭毛藻サキシトキシン 生合成のメタボロミクス解析2020

    • Author(s)
      ○長 由扶子、土屋 成輝、 小池 一彦、此木 敬一、 大島 泰克、山下 まり
    • Organizer
      令和2年度日本水産学会春季大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 高純度テトロドトキシン類縁体の定量とNav阻害活性2020

    • Author(s)
      ○山下まり*・佐藤恭佳・千葉 修・長 由扶子・此木敬一
    • Organizer
      令和2年度日本水産学会春季大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] クロイソカイメン抽出物由来電位依存性ナトリウムチャネル阻害剤の探索2020

    • Author(s)
      ○島田 紀子*、長 由扶子、此木 敬一、山下 まり
    • Organizer
      日本農芸化学会2020年度大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 超活性海洋天然有機化合物マイトトキシンの標的分子探索2020

    • Author(s)
      角替 俊輔、チャン キャサリーン、トン エイミーヒンヤン、アウラク カマルディープカウアー、ハスビド アンドレア、松本 健、八代田 陽子、モファット ジェイソン、ブーン チャールズ、山下 まり、村田 道雄、吉田 稔、○此木 敬一*
    • Organizer
      日本農芸化学会2020年度大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 致死性海藻中毒原因物質ポリカバノシド類の作用機序2019

    • Author(s)
      〇山下まり*,土肥裕花,島田紀子,岩崎浩太郎,佐々木 理,川島悠岐,此木敬一,佐々木誠
    • Organizer
      科研費新学術領域研究 化学コミュニケーションのフロンテイア 第6回公開シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] 中間体に基づく海洋生物毒の生合成研究2019

    • Author(s)
      山下まり
    • Organizer
      東京大学大学院薬学系研究科天然物化学教室セミナー
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] テトロドトキシン類縁体の電位依存性Naチャネル阻害活性と生合成経路の推定2019

    • Author(s)
      山下まり
    • Organizer
      第46回日本毒性学会学術年会,シンポジウム「海産毒リビジテッド」
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Identification of biosynthetic intermediates of amnesic shellfish toxin domoic acid and anthelmintic compound kainic acid2019

    • Author(s)
      〇Maeno, Y., Kotaki, Y., Terada, R., Cho, Y., Konoki, K. and Yotsu-Yamashita, M.
    • Organizer
      Gordon Research Conference, Mycotoxins and Phycotoxins
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Metabolomic study of saxitoxin biosynthesis in dinoflagellates using 15N-labelled sodium nitrate as a nitrogen source2019

    • Author(s)
      〇Cho, Y., Tsuchiya, S., Omura, T., Koike, K., Oikawa, H., Konoki, K., Oshima, Y. and Yotsu-Yamashita, M.
    • Organizer
      Gordon Research Conference, Mycotoxins and Phycotoxins
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 神経興奮物質カイノイド類の生合成中間体の同定及び生理活性評価2019

    • Author(s)
      前野優香理* 、小瀧裕一 、寺田竜太 、長由扶子 、此木敬一 、山下まり
    • Organizer
      第30回万有仙台シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Identification of new analogs and putative biosynthetic intermediates of tetrodotoxin aimed at elucidating its biosynthetic pathway and structure activity relationship2019

    • Author(s)
      ○Kudo, Y. and Yotsu-Yamashita, M.
    • Organizer
      60th American Society of Pharmacognosy Annual Meeting 2019
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Screening of novel secondary metabolites from microorganisms associated with the marine sponge Halichondria okadai2019

    • Author(s)
      〇Goto, M., Kikuchi, S., Okada, K., Cho, Y., Yotsu-Yamashita, M. and Konoki, K.
    • Organizer
      Tohoku University’s Chemistry Summer School
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Isolation and structural elucidation of tetrodotoxin related compounds from pufferfish2019

    • Author(s)
      〇Yaegashi, Y., Ueyama, N., Kudo, Y., Cho, Y., Konoki, K. and Yotsu-Yamashita, M.
    • Organizer
      Tohoku University’s Chemistry Summer School
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ドウモイ酸とカイニン酸の新規関連化合物の単離,構造決定と生合成経路2019

    • Author(s)
      〇前野優香理, 小瀧裕一, 寺田竜太, 長 由扶子,此木敬一, 山下まり
    • Organizer
      第61回天然有機化合物討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] C11位炭素置換型サキシトキシン誘導体の合成と活性評価2019

    • Author(s)
      〇安達栞菜,石塚 颯,山田智士,日高將文,広川貴次,小田木 陽,此木敬一,山下まり,長澤和夫
    • Organizer
      第61回天然有機化合物討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] テトロドトキシンの推定生合成中間体の全合成と絶対立体配置の決定2019

    • Author(s)
      ○宮坂忠親,安立昌篤,工藤雄大,杉本敬太,山下まり,西川俊夫
    • Organizer
      第61回天然有機化合物討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ホタテガイに含有する麻痺性貝毒の代謝物に関する研究2019

    • Author(s)
      沼野 聡,加賀克昌,工藤雄大,山下まり
    • Organizer
      第115回日本食品衛生学会学術講演会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 海洋生物毒の謎に迫る2019

    • Author(s)
      山下まり
    • Organizer
      仙台青葉学院短期大学講演会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Crisprスクリーニングによる maitotoxin の標的分子探索(2)2019

    • Author(s)
      角替俊輔,Katherine Chan,Amy Hin Yan Tong, Kamaldeep Kaur Aulakh, Andrea Habsid,八代田陽子,Jason Moffat,Charles Boone,山下まり, 村田道雄,〇此木敬一
    • Organizer
      公益社団法人日本農芸化学会東北支部・第154回大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Crisprスクリーニングによる maitotoxin の標的分子探索(1)2019

    • Author(s)
      〇角替俊輔,Katherine Chan,Amy Hin Yan Tong,Kamaldeep Kaur Aulakh, Andrea Habsid,八代田陽子,Jason Moffat,Charles Boone,山下まり,村田道雄,此木敬一
    • Organizer
      公益社団法人日本農芸化学会東北支部・第154回大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] LC-MS/MSを用いた抗マラリア活性天然物サリニポスチンの新規類縁体の探索2019

    • Author(s)
      ○工藤雄大, 山下まり
    • Organizer
      公益社団法人日本農芸化学会東北支部・第154回大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 淡水産藍藻 Anabaena circinalis (TA04 株)における新規麻痺性貝毒類縁体の探索2019

    • Author(s)
      赤松みちる,長 由扶子,此木敬一,山下まり
    • Organizer
      公益社団法人日本農芸化学会東北支部・第154回大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 岩手県産ホタテガイの中腸腺に含有する麻痺性貝毒の分析2019

    • Author(s)
      沼野 聡*,加賀克昌,工藤雄大,山下まり
    • Organizer
      第56回 全国衛生化学技術協議会年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Identification of seven possible biosynthetic intermediates of tetrodotoxin in marine environments isolated from pufferfish2018

    • Author(s)
      ○Mari Yotsu-Yamashita, Nozomi Ueyama, Keita Sugimoto, Yuji Yaegashi, Yuta Kudo, Ken-ichi Onodera, Yuko Cho, Keiichi Konoki, and Toshio Nishikawa.
    • Organizer
      18th International Conference on Harmful Alga
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Usefulness of column switching HILIC-MS and 15N-labeled inorganic nitrogen for the study of STX biosynthesis in dinoflagellates2018

    • Author(s)
      ○Yuko Cho, Shigeki Tsuchiya, Keiichi Konoki, Yasukatsu Oshima, and Mari Yotsu-Yamashita.
    • Organizer
      18th International Conference on Harmful Alga
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Bioconversion of putative biosynthetic intermediates of amnesic shellfish toxin, domoic acid, in the diatom Pseudo-nitzschia multiseries.2018

    • Author(s)
      ○Yukari Maeno, Yuichi Kotaki, Yuko Cho, Keiichi Konoki, and Mari Yotsu-Yamashita.
    • Organizer
      Tohoku University Chemistry Summer School 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Screening for bioactive compounds in marine organisms collected in the Solomon Islands2018

    • Author(s)
      ○Masato Kasuga, Clyde Gorapava Puilingi, Atsuo Nakazaki, Shunsuke Tsunogae, Yuko Cho, Keiichi Konoki, Toshio Nishikawa, and Mari Yotsu-Yamashita
    • Organizer
      Tohoku University Chemistry Summer School 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 化学的手法による海産毒の生合成経路の推定2018

    • Author(s)
      山下まり
    • Organizer
      2018年度農芸化学会東北支部シンポジウム 天然有機化合物が拓く新研究展開
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 中間体を基盤とした海産毒の生合成研究2018

    • Author(s)
      山下まり
    • Organizer
      日本薬学会生薬天然物部会 「第22回天然薬物の開発と応用シンポジウム」
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 海洋生物毒の謎に迫る2018

    • Author(s)
      山下まり
    • Organizer
      仙台青葉学院短期大学講演会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 紅藻ハナヤナギ(Chondria armata)から同定したドウモイ酸の推定生合成中間体のLC-MS分析法の検討2018

    • Author(s)
      前野 優香理,○山下まり,長 由扶子,此木敬一,小瀧裕一,寺田竜太
    • Organizer
      平成30年度日本水産学会春季大会
    • Related Report
      2018 Annual Research Report
  • [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年度日本水産学会春季大会
    • Related Report
      2018 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
      2018 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
      2018 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
      2018 Annual Research Report
  • [Presentation] 記憶喪失性貝毒ドウモイ酸の新規生合成中間体の同定と生合成経路の解明2018

    • Author(s)
      ○前野 優香理,小瀧裕一,寺田竜太,長 由扶子,此木敬一,山下まり
    • Organizer
      第29回万有仙台シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] テトロドトキシン類縁体に対する電位依存性ナトリウムチャネルの感受性評価2018

    • Author(s)
      ○塚本匡顕,千葉雪絵,若森 実,日高將文,山田智士,角替俊輔,長 由扶子,榊原 良,今津拓也,所 聖太,佐竹佳樹,安立昌篤,西川俊夫,山下まり,○此木敬一
    • Organizer
      第60回天然有機化合物討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 記憶喪失性貝毒ドウモイ酸の新規生合成中間体の同定と生合成経路の解明2018

    • Author(s)
      ○前野 優香理,小瀧裕一,寺田竜太,長 由扶子,此木敬一,山下まり
    • Organizer
      第65回トキシンシンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] ホタテガイ中腸腺に存在するオカダ酸アシル化酵素の探索法の開発2018

    • Author(s)
      ○寺内将斗,古用幸愛,長 由扶子,山下まり,此木敬一
    • Organizer
      日本農芸化学会東北・北海道合同支部大会(東北支部第153回大会)
    • Related Report
      2018 Annual Research Report
  • [Presentation] マイトトキシンの膜透過性亢進作用の機構解明に向けた電気生理学的アプローチ2018

    • Author(s)
      〇山田智士,岩本真幸,長 由扶子,老木成稔,村田道雄,山下まり,此木敬一
    • Organizer
      日本農芸化学会東北・北海道合同支部大会(東北支部第153回大会)
    • Related Report
      2018 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 “Fisheries Science for Future Generations”
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Prediction of Biosynthetic Pathways of Tetrodotoxin and Saxitoxin Based on the Structures of Intermediates.2017

    • Author(s)
      M. Yotsu-Yamashita
    • Organizer
      The 5th Tohoku University (TU)-Dalian University of Technology (DUT) Joint Symposium on Chemistry.
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] フグ毒の生合成経路解明へのアプローチ2017

    • Author(s)
      山下まり
    • Organizer
      日本農芸化学会創立100周年に向けたシンポジウム,Visionary農芸化学100シンポジウム 天然物化学領域 第一回「生命現象に介在する天然物の化学」
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 化学的手法による天然毒の生合成研究2017

    • Author(s)
      山下まり
    • Organizer
      第34回有機合成化学セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 食中毒を引き起こす海洋生物毒と対応策の進展2017

    • Author(s)
      山下まり
    • Organizer
      五大学共同開催フォーラム第7回食の安全研究ホットトピックス
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 化学的手法による天然毒の生合成研究2017

    • Author(s)
      山下まり
    • Organizer
      名古屋大学大学院生命農学研究科セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [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年度日本水産学会春季大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] モヨウフグ(Arothron)属3種およびオキナワフグ(Chelonodon patoca)血漿中のテトロドトキシン類とPSTBP類似タンパク質の解析2017

    • Author(s)
      長岡佑真,村本光二,長 由扶子,此木敬一,○山下まり
    • Organizer
      平成29年度日本水産学会春季大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 記憶喪失性貝毒ドウモイ酸新規関連化合物の探索2017

    • Author(s)
      ○海老根 優香理,小瀧裕一,寺田竜太,長 由扶子,此木敬一,山下まり
    • Organizer
      日本農芸化学会2017年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 有毒藍藻 Anabaena circinalis (TA04)からの未知麻痺性貝毒サキシトキシン類縁体の探索2017

    • Author(s)
      ○美野輪 高之,長 由扶子,土屋成輝,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
    • Related Report
      2017 Annual Research Report
  • [Presentation] フグにおける新規テトロドトキシン関連化合物の探索2017

    • 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2017年度大会
    • 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探索2017

    • Author(s)
      ○菊池 颯,岡田華弥,長 由扶子,山下まり,此木敬一
    • Organizer
      日本農芸化学会2017年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ベラトリジンによる電位依存性ナトリウムチャネルの不活性化遅延作用に対するクランベシンB類縁体の抑制効果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
      日本農芸化学会2017年度大会
    • 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] 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] 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
  • [Book] 水産の科学 カキ・ホタテガイの科学 5.1貝毒 (分担執筆)pp.139-152.2019

    • Author(s)
      山下まり、此木敬一
    • Total Pages
      214
    • Publisher
      朝倉書店
    • ISBN
      9784254485035
    • Related Report
      2019 Annual Research Report
  • [Remarks] 東北大学大学院農学研究科天然物生命化学分野HP

    • URL

      https://www.agri.tohoku.ac.jp/bukka/index-j.html

    • Related Report
      2019 Annual Research Report
  • [Remarks] 東北大学大学院農学研究科天然物生命化学分野HP

    • URL

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

    • Related Report
      2018 Annual Research Report 2017 Annual Research Report

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Published: 2017-04-28   Modified: 2021-02-19  

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