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Synthetic study on a bioactive natural product, the most active hatching agent of potato cyst nematodes by radical cyclization

Research Project

Project/Area Number 15K07410
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bioorganic chemistry
Research InstitutionNagoya University

Principal Investigator

Adachi Masaatsu  名古屋大学, 生命農学研究科, 助教 (80432251)

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: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords天然物化学 / 有機化学 / 合成化学
Outline of Final Research Achievements

Synthesis of solanoeclepin A, the most active hatching agent of potato cyst nematode isolated from hydroponic potato cultures was examined not only for the chemical supply of solanoeclepin A but also for the structure-activity relationship study. As a result, a tricyclic compound possessing a DEF ring of the right-hand nucleus of solanoeclepin A was synthesized from Hajos-Parrish ketone through introduction of a hydroxy group at the C-15 position and construction of the highly strained cyclobutane by samarium(II)-mediated 4-exo-trig radical cyclization.

Report

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

    (35 results)

All 2018 2017 2016 2015

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Acknowledgement Compliant: 4 results) Presentation (26 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] Facile Enzymatic Synthesis of Phosphatidylthreonine Using an Engineered Phospholipase D2018

    • Author(s)
      Damnjanovic, J.; Matsunaga, N.; Adachi, M.; Nakano, H.; Iwasaki, Y
    • Journal Title

      Eur. J. Lipid Sci. Technol.

      Volume: 120 Issue: 6 Pages: 1800089-1800095

    • DOI

      10.1002/ejlt.201800089

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-step Transformation of Trichloroacetamide into Isonitrile.2017

    • Author(s)
      Adachi, M.; Miyasaka, T.; Hashimoto, H.; Nishikawa, T.
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 2 Pages: 380-383

    • DOI

      10.1021/acs.orglett.6b03583

    • Related Report
      2017 Annual Research Report 2016 Research-status 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] Improved Syntheses of (+)-Iridomyrmecin and (-)-Isoiridomyrmecin, Major Components of Matatabilactone.2016

    • Author(s)
      Adachi, M.; Miyazawa, Y; Nishikawa, T.
    • Journal Title

      Nat. Prod. Commun.

      Volume: 11 Pages: 883-886

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct Enzymatic Synthesis of 1-Phosphatidyl-β-D-glucose by Engineered Phospholipase D.2016

    • Author(s)
      Inoue, A.; Adachi, M.; Damnjanovic, J.; Nakano, H.; Iwasaki, Y.
    • Journal Title

      Chemistryselect

      Volume: 1 Issue: 13 Pages: 4121-4125

    • DOI

      10.1002/slct.201600839

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Synthesis of 3-Azide-4-fluoro-L-phenylalanine.2015

    • Author(s)
      Adachi, M.; Nakajima, M.; Isobe, M.
    • Journal Title

      Biosci. Biotechnol. Biochem.

      Volume: XX Issue: 5 Pages: 0-0

    • DOI

      10.1080/09168451.2014.997185

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Synthesis of ABC-tricycle of Solanoeclepin A.2015

    • Author(s)
      Adachi, M.; Torii, M.; Nishikawa, T.
    • Journal Title

      Synlett

      Volume: 26 Issue: 07 Pages: 965-969

    • DOI

      10.1055/s-0034-1380399

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Multifunctionality of the N-Trichloroacetyl Group Developed in the Synthesis of Tetrodotoxin, a Puffer Fish Toxin2015

    • Author(s)
      Toshio Nishikawa, Daisuke Urabe, Masaatsu Adachi, Minoru Isobe
    • Journal Title

      Synlett

      Volume: 26 Issue: 14 Pages: 1930-1939

    • DOI

      10.1055/s-0034-1380781

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 分子内C-グリコシル化反応を利用したPolygalolide Aの全合成2015

    • Author(s)
      安立昌篤
    • Journal Title

      有機合成化学協会誌

      Volume: 73 Pages: 607-615

    • NAID

      130005088786

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] テトロドトキシンの推定生合成中間体の化学合成研究2018

    • Author(s)
      宮坂忠親、安立昌篤、杉本敬太、山下まり、西川俊夫
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ジャガイモシスト線虫孵化促進物質ソラノエクレピンAの右側部分の合成研究2018

    • Author(s)
      幸木謙典、宮澤 悠、駒田武馬、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] テトロドトキシンのフグ誘引活性の解明を目的とした類縁体の合成研究2018

    • Author(s)
      中東亮太、安立昌篤、野口能寿、山本直之、阿部秀樹、西川俊夫
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] クサフグ(Takifugu niphobles)におけるフグ毒類縁体に対する嗅覚感知機構2018

    • Author(s)
      野口能寿、榊原 良、佐竹佳樹、安立昌篤、西川俊夫、山本直之、阿部秀樹
    • Organizer
      平成30年度日本水産学会
    • Related Report
      2017 Annual Research Report
  • [Presentation] トリクロロアセトアミドからイソニトリルへの新規な一段階変換反応2017

    • Author(s)
      宮坂忠親、橋本穂果、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2017年度大会
    • Place of Presentation
      京都
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] 蛍光デキストランを利用した匂い刺激に応答するクサフグ嗅上皮細胞の同定2017

    • Author(s)
      野口能寿、榊原 良、佐竹佳樹、安立昌篤、西川俊夫・山本直之、阿部秀樹
    • Organizer
      日本動物学会第88回富山大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] フグ毒テトロドトキシンの推定生合成中間体の化学合成研究2017

    • Author(s)
      宮坂忠親、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会中部支部180回例会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ジャガイモシスト線虫孵化促進物質ソラノエクレピンAの右側部分の合成研究2017

    • Author(s)
      幸木謙典、宮澤 悠、駒田武馬、安立昌篤、西川俊夫
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Can Grass Pufferfish (Takifugu Niphobles) Sniff “Tetrodotoxins” ?2016

    • Author(s)
      Yoshihisa Noguchi, Ryo Sakakibara, Yoshiki Satake, Masaatsu Adachi, Naoyuki Yamamoto, Toshio Nishikawa, Hideki Abe
    • Organizer
      The 22nd International Congress of Zoology and The 87th Meeting of The Zoological Society of Japan Joint Events
    • Place of Presentation
      Okinawa
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] トリクロロアセトアミドからイソニトリルへの新規な一段階変換反応2016

    • Author(s)
      宮坂忠親、橋本穂果、安立昌篤、西川俊夫
    • Organizer
      第47回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋
    • Year and Date
      2016-11-05
    • Related Report
      2016 Research-status Report
  • [Presentation] クサフグはTTX を匂いとして感知できるか?2016

    • Author(s)
      野口能寿、榊原 良、佐竹直樹、安立昌篤、西川俊夫、山本直之、阿部秀樹
    • Organizer
      第二回ユニークな少数派実験動物を使う若手が最先端アプローチを勉強する会
    • Place of Presentation
      岡崎
    • Year and Date
      2016-08-21
    • Related Report
      2016 Research-status Report
  • [Presentation] ジャガイモシスト線虫孵化促進物質ソラノエクレピンA右側部分の合成研究2016

    • Author(s)
      宮澤 悠、駒田武馬、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] 8-epiテトロドトキシンの合成研究2016

    • Author(s)
      岩瀬翔太郎、堀田貴大、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] セスペンドール芳香環部分の光学活性体の合成研究2016

    • Author(s)
      植木佳織、樋口恵子、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] ジャガイモシスト線虫孵化促進物質ソラノエクレピンA左側部分の合成研究2016

    • Author(s)
      長谷川耕太、鳥居真衣、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] ネコにマタタビ反応を誘発する新規活性物質の同定2016

    • Author(s)
      室岡孝信、宮澤 悠、安立昌篤、山下哲郎、西川俊夫、宮崎雅雄
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] 電位依存性ナトリウムチャネルに対するテトロドトキシンおよびその類縁体の阻害活性評価2016

    • Author(s)
      塚本匡顕、千葉雪絵、安立昌篤、榊原 良、所 聖太、今津拓也、佐竹佳樹、長 由扶子、西川俊夫、山下まり、此木敬一
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] 酵素によるホスファチジル-β-1-グルコースの合成2016

    • Author(s)
      井上ありさ, 安立昌篤, ダムニャノビッチヤスミナ, 中野秀雄, 岩崎雄吾
    • Organizer
      第6回学際的脂質創生研究部会講演会
    • Place of Presentation
      徳島
    • Year and Date
      2016-01-22
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis of biologically active steroid-derived compounds from an edible mushroom2015

    • Author(s)
      Toshio Nishikawa, Yoshiki Nakane, Atsuo Nakazaki, Takuya Imazu, Shouta Tokoro, Ryo Sakakibara, Masaatsu Adachi, Keiichi Konoki, Mari Yotsu-Yamashita
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and biological activities of guanidine-containing natural products2015

    • Author(s)
      Toshio Nishikawa, Yoshiki Nakane, Atsuo Nakazaki, Takuya Imazu, Shouta Tokoro, Ryo Sakakibara, Masaatsu Adachi, Keiichi Konoki, Mari Yotsu-Yamashita
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ジャガイモシスト線虫孵化促進物質ソラノエクレピンAの右側部分の合成研究2015

    • Author(s)
      宮澤 悠、駒田武馬、安立昌篤、西川俊夫
    • Organizer
      第46回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      津
    • Year and Date
      2015-11-07
    • Related Report
      2015 Research-status Report
  • [Presentation] 電位依存性ナトリウムチャネルに対するテトロドトキシンおよび類縁体の活性阻害評価2015

    • Author(s)
      塚本匡顕、千葉雪絵、長 由扶子、安立昌篤、榊原 良、所 聖太、今津拓也、中崎敦夫、石川裕生、西川俊夫、山下まり、此木敬一
    • Organizer
      日本農芸化学会東北支部第150回大会
    • Place of Presentation
      仙台
    • Year and Date
      2015-10-03
    • Related Report
      2015 Research-status Report
  • [Presentation] 1-ホスファチジル-β-D-グルコースの酵素合成2015

    • Author(s)
      井上ありさ, 安立昌篤,中野秀雄, Jasmina Damnjanovic, 岩崎雄吾
    • Organizer
      2015 年度日本農芸化学会中部・関西支部合同大会
    • Place of Presentation
      富山
    • Year and Date
      2015-09-19
    • Related Report
      2015 Research-status Report
  • [Presentation] 1 -ホスファチジル-β-D-グルコースの酵素合成2015

    • Author(s)
      井上ありさ, 安立昌篤, 中野 秀雄, ダムナニョヴィッチ ヤスミナ, 岩崎 雄吾.
    • Organizer
      生物工学若手研究者の集い(若手会)夏のセミナー2015
    • Place of Presentation
      名古屋
    • Year and Date
      2015-07-16
    • Related Report
      2015 Research-status Report
  • [Presentation] ナトリウムチャネル阻害剤の創製を目指したグアニジン系天然物の合成2015

    • Author(s)
      西川俊夫、中崎敦夫、中根嘉祈、石川裕生、安立昌篤、橋本穂果、今津拓也、所聖太、榊原良、此木敬一、千葉雪絵、山下まり
    • Organizer
      日本ケミカルバイオロジー学会 第10回年会
    • Place of Presentation
      仙台
    • Year and Date
      2015-06-10
    • Related Report
      2015 Research-status Report
  • [Presentation] 天然グアニジン化合物を基盤としたイオンチャネル阻害剤の開発2015

    • Author(s)
      西川俊夫、中崎敦夫、安立昌篤、此木敬一、山下まり
    • Organizer
      天然物ケミカルバイオロジー~分子標的と活性制御~ 第8回公開シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2015-06-08
    • Related Report
      2015 Research-status Report

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

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