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Structural Elucidation and Structure-Activity Relationship Study of Biologically Active Natural Products on the Basis of Organic Synthetic Chemistry

Research Project

Project/Area Number 17K05862
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionOkayama University

Principal Investigator

TAKAMURA Hiroyoshi  岡山大学, 自然科学研究科, 准教授 (70422798)

Co-Investigator(Kenkyū-buntansha) 大野 修  工学院大学, 先進工学部, 准教授 (20436992)
Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2019: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords有機合成化学 / 構造解明 / 生物活性 / 天然物 / 全合成 / 発散的合成 / 立体化学 / 構造活性相関 / 有機化学 / 合成化学 / 天然物化学
Outline of Final Research Achievements

Structural elucidation of natural products is a significant research topic. Structural elucidation can give information of the structure-activity relationship and lead to identification of the pharmacophore, design and synthesis of the molecular probe, identification of the target molecule in vivo, clarification of the mode of action, and creation of the biologically active analogue. In this research, the stereostructures of the biologically active natural products have been determined by the synthetic approach. In addition, the structure-activity relationship has been elucidated by the biological evaluation of the synthetic products and the novel biologically active molecules have been created.

Academic Significance and Societal Importance of the Research Achievements

近年の機器分析の著しい発展に伴い、天然物の構造決定が微量成分にて可能となってきた。しかしながら、分子サイズが大きい、多官能基化されている、誘導化が困難である、結晶化が困難であるなどの場合には、天然物を用いての構造解析は困難を極める。このような場合には、化学合成による構造決定が有効かつ信頼性の高い手段となる。本研究では、機器分析による構造決定が困難な生物活性天然物を研究対象とし、合成化学的アプローチを用いることで、その立体構造と構造活性相関を解明した。さらに、天然物を構造基盤とした新規生物活性分子を創製した。

Report

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

    (38 results)

All 2020 2019 2018 2017 Other

All Int'l Joint Research (4 results) Journal Article (13 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 13 results,  Open Access: 10 results) Presentation (18 results) (of which Int'l Joint Research: 1 results) Book (1 results) Remarks (2 results)

  • [Int'l Joint Research] 中国科学院上海薬物研究所(中国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] アテネ大学(ギリシャ)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] 中国科学院上海薬物研究所(中国)

    • Related Report
      2018 Research-status Report
  • [Int'l Joint Research] アテネ大学(ギリシャ)

    • Related Report
      2017 Research-status Report
  • [Journal Article] Chemical synthesis and biological effect on xylem formation of xylemin and Its analogues2020

    • Author(s)
      Hiroyoshi Takamura, Hiroyasu Motose, Taichi Otsu, Shiori Shinohara, Ryugo Kouno, Isao Kadota, Taku Takahashi
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2020 Issue: 18 Pages: 2745-2753

    • DOI

      10.1002/ejoc.202000322

    • NAID

      120006999366

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Inhibitory effects of biseokeaniamide A against lipopolysaccharide-induced signal transduction2020

    • Author(s)
      Osamu Ohno, Takuro Terasaki, Takuya Sano, Yuki Hitomi, Junichiro Miyamoto, Kenji Matsuno,
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 30 Issue: 11 Pages: 127069-127069

    • DOI

      10.1016/j.bmcl.2020.127069

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Unified Total Synthesis, Stereostructural Elucidation, and Biological Evaluation of Sarcophytonolides2019

    • Author(s)
      Takamura Hiroyoshi、Kadota Isao
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 77 Issue: 12 Pages: 1190-1200

    • DOI

      10.5059/yukigoseikyokaishi.77.1190

    • NAID

      130007760860

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2019-12-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Stereocontrolled synthesis of the macrolactone core of neopeltolide2019

    • Author(s)
      Meissner Andreas、Tanaka Nobuhiro、Takamura Hiroyoshi、Kadota Isao
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 5 Pages: 432-434

    • DOI

      10.1016/j.tetlet.2018.12.066

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Stereodivergent and Stereoselective Synthesis of cis- and trans-4-Substituted Prolinols2019

    • Author(s)
      Ando Junki、Tazawa Aoi、Ishizawa Kohei、Tanaka Minoru、Takamura Hiroyoshi
    • Journal Title

      HETEROCYCLES

      Volume: - Issue: 1 Pages: 188-199

    • DOI

      10.3987/com-18-s(f)8

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Concise Synthesis of Anticancer Active trans-4-(4-Octylphenyl)prolinol2019

    • Author(s)
      Ando Junki、Tazawa Aoi、Ishizawa Kohei、Tanaka Minoru、Takamura Hiroyoshi
    • Journal Title

      HETEROCYCLES

      Volume: - Issue: 1 Pages: 716-723

    • DOI

      10.3987/com-18-s(f)44

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthetic Approach toward the Structural Elucidation of Symbiodinolide: Stereodivergent Synthesis and Stereostructural Revision of the C79-C104 Fragment2018

    • Author(s)
      Takamura Hiroyoshi
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 76 Issue: 5 Pages: 474-477

    • DOI

      10.5059/yukigoseikyokaishi.76.474

    • NAID

      130006733908

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2018-05-01
    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Unified Total Synthesis, Stereostructural Elucidation, and Biological Evaluation of Sarcophytonolides2018

    • Author(s)
      Takamura Hiroyoshi、Kikuchi Takahiro、Iwamoto Kohei、Nakao Eiji、Harada Naoki、Otsu Taichi、Endo Noriyuki、Fukuda Yuji、Ohno Osamu、Suenaga Kiyotake、Guo Yue-Wei、Kadota Isao
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 18 Pages: 11028-11056

    • DOI

      10.1021/acs.joc.8b01634

    • NAID

      120006712888

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Formal total synthesis of enigmazole A2018

    • Author(s)
      Meissner Andreas、Kishi Takayuki、Fujisawa Yuka、Murai Yuto、Takamura Hiroyoshi、Kadota Isao
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 51 Pages: 4492-4495

    • DOI

      10.1016/j.tetlet.2018.11.017

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total Synthesis of Rhoiptelol B2018

    • Author(s)
      Kadota Isao、Tanaka Nobuhiro、Takamura Hiroyoshi
    • Journal Title

      HETEROCYCLES

      Volume: 97 Issue: 2 Pages: 1157-1164

    • DOI

      10.3987/com-18-s(t)57

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Recent topics of the stereodivergent synthesis of natural products2018

    • Author(s)
      Takamura Hiroyoshi
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 11 Pages: 955-966

    • DOI

      10.1016/j.tetlet.2018.02.004

    • NAID

      120006623774

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Two Possible Diastereomers of Natural 6-Chlorotetrahydrofuran Acetogenin and Its Stereostructural Elucidation2017

    • Author(s)
      Takamura Hiroyoshi、Katsube Tomoya、Okamoto Kazuki、Kadota Isao
    • Journal Title

      Chemistry - A European Journal

      Volume: 23 Issue: 68 Pages: 17191-17194

    • DOI

      10.1002/chem.201703234

    • NAID

      120006517772

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Late-stage divergent synthesis and antifouling activity of geraniol-butenolide hybrid molecules2017

    • Author(s)
      Takamura Hiroyoshi、Ohashi Takumi、Kikuchi Takahiro、Endo Noriyuki、Fukuda Yuji、Kadota Isao
    • Journal Title

      Organic and Biomolecular Chemistry

      Volume: 15 Issue: 26 Pages: 5549-5555

    • DOI

      10.1039/c7ob01160a

    • NAID

      120006522864

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] スカブロライドFの合成研究2020

    • Author(s)
      杉谷侑紀、青木浩孝、髙村浩由、門田功
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 構造解明を目的としたシンビオジノライドC69-C83フラグメントの立体発散的合成研究2020

    • Author(s)
      服部光祐、大津泰知、大橋拓実、髙村浩由、門田功、上村大輔
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Unified Total Synthesis, Stereochemical Elucidation, and Antifouling Activity of Sarcophytonolides2019

    • Author(s)
      Takamura Hiroyoshi、Kikuchi Takahiro、Iwamoto Kohei、Nakao Eiji、Harada Naoki、Otsu Taichi、Endo Noriyuki、Fukuda Yuji、Guo Yue-Wei、Kadota Isao
    • Organizer
      27th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ゲラニオール-ブテノライド ハイブリッド分子の発散的合成と付着阻害活性2019

    • Author(s)
      髙村浩由、大橋拓実、菊地崇浩、遠藤紀之、福田祐司、門田功
    • Organizer
      第61回天然有機化合物討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 全合成を基盤とした6-クロロテトラヒドロフランアセトゲニンの構造解明2019

    • Author(s)
      髙村浩由、勝部友哉、岡本和樹、門田功
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] ブテノライドを構造基盤とする付着阻害活性分子の合成と評価2019

    • Author(s)
      髙村浩由、菊地崇浩、大津泰知、大橋拓実、門田功、遠藤紀之、福田祐司
    • Organizer
      2019年度日本付着生物学会研究集会
    • Related Report
      2018 Research-status Report
  • [Presentation] シンビオジノライドC61-C74フラグメントの立体発散的合成と構造決定2019

    • Author(s)
      大橋拓実、髙村浩由、門田功、上村大輔
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ビピナチンIの合成研究2018

    • Author(s)
      菊地崇浩、髙村浩由、門田功
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] カリビアンシガトキシン(C-CTX-1)のAB環部の合成研究2018

    • Author(s)
      大塚史也、髙村浩由、門田功
    • Organizer
      第34回若手化学者のための化学道場(高知2018)
    • Related Report
      2018 Research-status Report
  • [Presentation] 6-クロロテトラヒドロフランアセトゲニン類の合成研究2018

    • Author(s)
      山本克裕、髙村浩由、門田功
    • Organizer
      第34回若手化学者のための化学道場(高知2018)
    • Related Report
      2018 Research-status Report
  • [Presentation] Formal Total Syntheses of Enigmazole A and Neopeltolide2018

    • Author(s)
      Andreass Meissner, Takayuki Kishi, Yuka Fujisawa, Yuto Murai, Nobuhiro Tanaka, Hiroyoshi Takamura, Isao Kadota
    • Organizer
      第60回天然有機化合物討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ビピナチンIの合成研究2018

    • Author(s)
      菊地崇浩、髙村浩由、門田功
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] ゲラニオール-ブテノライド ハイブリッド分子の発散的合成と付着阻害活性2018

    • Author(s)
      大橋拓実、菊地崇浩、遠藤紀之、福田祐司、髙村浩由、門田功
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 6-クロロテトラヒドロフランアセトゲニンの全合成と立体構造解明2017

    • Author(s)
      髙村浩由、勝部友哉、岡本和樹、門田功
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] サルコフィトノライドJの構造予測および全合成による構造決定2017

    • Author(s)
      大津泰知、髙村浩由、門田功
    • Organizer
      第111回有機合成シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] スカブロライドEのテトラヒドロフランフラグメントの合成2017

    • Author(s)
      青木浩孝、森下諒平、髙村浩由、門田功
    • Organizer
      第33回若手化学者のための化学道場(鳥取2017)
    • Related Report
      2017 Research-status Report
  • [Presentation] ゲラニオール-ブテノライド ハイブリッド分子の発散的合成と付着阻害活性2017

    • Author(s)
      大橋拓実、髙村浩由、菊地崇浩、遠藤紀之、福田祐司、門田功
    • Organizer
      第33回若手化学者のための化学道場(鳥取2017)
    • Related Report
      2017 Research-status Report
  • [Presentation] ゲラニオール-ブテノライド ハイブリッド分子の発散的合成と付着阻害活性2017

    • Author(s)
      髙村浩由、大橋拓実、菊地崇浩、遠藤紀之、福田祐司、門田功
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Research-status Report
  • [Book] Protecting-Group-Free Organic Synthesis: Improving Economy and Efficiency2018

    • Author(s)
      Takamura, H.; Kadota, I.
    • Total Pages
      288
    • Publisher
      John Wiley & Sons Ltd.
    • ISBN
      9781119295204
    • Related Report
      2018 Research-status Report
  • [Remarks] 研究代表者のホームページ

    • URL

      http://chem.okayama-u.ac.jp/staff/detail/hiroyoshi-takamura.html

    • Related Report
      2019 Annual Research Report 2018 Research-status Report
  • [Remarks] 研究代表者ホームページ

    • URL

      http://chem.okayama-u.ac.jp/staff/detail/hiroyoshi-takamura.html

    • Related Report
      2017 Research-status Report

URL: 

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

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