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

Research Project

Project/Area Number 18K05456
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 38040:Bioorganic chemistry-related
Research InstitutionTohoku University (2019-2020)
Nagoya University (2018)

Principal Investigator

Adachi Masaatsu  東北大学, 薬学研究科, 准教授 (80432251)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords有機化学 / 合成化学 / 天然物化学 / 生理活性
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 for the chemical supply of solanoeclepin A. 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.

Academic Significance and Societal Importance of the Research Achievements

申請者は、化学合成によって得られる天然物や中間体等を利用すれば生命現象を分子レベルで詳細に解明できると考え、天然から得ることが困難でその生理活性の詳細が明らかにされていない天然有機化合物を研究材料に取り上げ、その合成研究を行っている。本研究で着目した高度に歪んだシクロブタンを持つソラノエクレピンAは、天然からの単離収率が極めて低く、生合成経路も未だ不明なことから、有機合成による量的供給が必要不可欠である。また、合成難度が極めて高いため、構造活性相関の情報に基づきシスト線虫の孵化促進活性を保持した単純化アナログを開発することが重要であると考えた。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (21 results)

All 2021 2020 2019 2018

All Journal Article (7 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 7 results,  Open Access: 2 results) Presentation (14 results)

  • [Journal Article] The characteristic response of domestic cats to plant iridoids allows them to gain chemical defense against mosquitoes.2021

    • Author(s)
      Uenoyama, R.; Miyazaki, T.; Hurst, J.; Beynon, R.; Asachi, M.; Murooka, T.; Onoda, I.; Miyazawa, Y.; Katayama, T.; Yamashita, T.; Kaneko, S.; Nishikawa, T.; Miyazaki, M.
    • Journal Title

      Sci. Adv.

      Volume: 7 Issue: 4 Pages: 1-14

    • DOI

      10.1126/sciadv.abd9135

    • NAID

      120006952777

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] First Detection of Tetrodotoxins in the Cotylean Flatworm Prosthiostomum trilineatum2021

    • Author(s)
      Suo Rei、Kashitani Maho、Oyama Hikaru、Adachi Masaatsu、Nakahigashi Ryota、Sakakibara Ryo、Nishikawa Toshio、Sugita Haruo、Itoi Shiro
    • Journal Title

      Marine Drugs

      Volume: 19 Issue: 1 Pages: 40-40

    • DOI

      10.3390/md19010040

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Biosynthesis of Indole Diterpene Lolitrems: Radical-Induced Cyclization of an Epoxyalcohol Affording a Characteristic Lolitremane Skeleton2020

    • Author(s)
      Yulu Jiang, Taro Ozaki, Mei Harada, Tadachika Miyasaka, Hajime Sato, Kazunori Miyamoto, Junichiro Kanazawa, Chengwei Liu, Jun-ichi Maruyama, Masaatsu Adachi, Atsuo Nakazaki, Toshio Nishikawa, Masanobu Uchiyama, Atsushi Minami, Hideaki Oikawa
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 59 Issue: 41 Pages: 17996-18002

    • DOI

      10.1002/anie.202007280

    • NAID

      120007160289

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [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 Research-status Report 2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Concise Stereocontrolled Synthesis of an α-Carbagalactose Segment of RCAI-56, a Candidate of Anticancer Agent.2019

    • Author(s)
      Ushida, N.; Nagai, N.; Adachi, M.; Nishikawa, T.
    • Journal Title

      Synlett

      Volume: 30 Issue: 08 Pages: 977-981

    • DOI

      10.1055/s-0037-1611806

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of the Aromatic Fragment of Sespendole.2019

    • Author(s)
      Ono, Y.; Nakazaki, A.; Ueki, K.; Higuchi, K.; Sriphana, U.; Adachi, M.; Nishikawa, T.
    • Journal Title

      J. Org. Chem.

      Volume: 84 Issue: 15 Pages: 9750-9757

    • DOI

      10.1021/acs.joc.9b01597

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [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
      2018 Research-status Report
    • Peer Reviewed
  • [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2021

    • Author(s)
      安立 昌篤、柳 誠人、幸木 謙典、宮澤 悠、駒田 武馬、西川 俊夫、土井 隆行
    • Organizer
      日本薬学会第141年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Solid Phase Synthesis of Heterocyclic Compounds by Suzuki-Miyaura Cross Coupling Reaction2020

    • Author(s)
      安立 昌篤、川平浩希、土井 隆行
    • Organizer
      令和2年度化学系学協会東北大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Synthetic Studies on Right Segment of Solanoeclepin A, a Hatching Agent of Potato Cyst Nematode2020

    • Author(s)
      安立 昌篤、柳 誠人、幸木 謙典、宮澤 悠、駒田 武馬、西川 俊夫、土井 隆行
    • Organizer
      令和2年度化学系学協会東北大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] テトロドトキシンの推定生合成中間体の合成研究2020

    • Author(s)
      宮坂忠親、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2020年度大会
    • Related Report
      2019 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のABCD環部分の合成研究2020

    • Author(s)
      立松怜史、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2020年度大会
    • Related Report
      2019 Research-status Report
  • [Presentation] プルミスクレリンAの合成研究2020

    • Author(s)
      柴田将貴、西川俊夫、安立昌篤
    • Organizer
      日本農芸化学会2020年度大会
    • Related Report
      2019 Research-status Report
  • [Presentation] テトロドトキシン推定生合成中間体Cep-212とCep-210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 Research-status Report
  • [Presentation] Sensitivity of the voltage-gated sodium channel subtypes, Nav1.1 to Nav1.7, against guanidine-containing natural products and their analogues2019

    • Author(s)
      Tadaaki Tsukamoto, Yukie Chiba, Shunsuke Tsunogae, Tomoshi Yamada, Yuko Cho, Ryo Sakakibara, Takuya Imazu, Shouta Tokoro, Yoshiki Satake, Yuki Ishikawa, Yoshiki Nakane, Masaatsu Adachi, Atsuo Nakazaki, Toshio Nishikawa, Minoru Wakamori, Mari Yotsu-Yamashita, Keiichi Konoki
    • Organizer
      The 1st International Symposium on Chemical Communication (ISCC2019)
    • Related Report
      2018 Research-status 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
      日本農芸化学会2019年度大会
    • Related Report
      2018 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2019

    • Author(s)
      立松怜史、安立昌篤、西川俊夫
    • Organizer
      日本農芸化学会2019年度大会
    • Related Report
      2018 Research-status Report
  • [Presentation] テトロドトキシン推定生合成中間体のテトロドトキシン含有生物への投与2019

    • Author(s)
      杉本敬太、工藤雄大、宮坂忠親、安立昌篤、長 由扶子、此木敬一、千葉親文、西川俊夫、山下まり
    • Organizer
      日本農芸化学会2019年度大会
    • Related Report
      2018 Research-status Report
  • [Presentation] 天然物の網羅的合成と新生物機能の解明2019

    • Author(s)
      西川俊夫、中崎敦夫、安立昌篤
    • Organizer
      日本農芸化学会2019年度大会シンポジウム「農芸化学における有機合成の力―その視点と未来―」
    • Related Report
      2018 Research-status Report
  • [Presentation] テトロドトキシン推定生合成中間体の合成研究2018

    • Author(s)
      宮坂忠親、安立昌篤、杉本敬太、山下まり、西川俊夫
    • Organizer
      第113回有機合成シンポジウム2018年
    • Related Report
      2018 Research-status 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、角替俊輔、山田智士、若森 実、日高 將文、長 由扶子、安立昌篤、榊原 良、所 聖太、今津拓也、佐竹佳樹、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 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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