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Total synthesis and structure activity relationship of natural products with potent anticancer activity and unique structures

Research Project

Project/Area Number 22380064
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

KUWAHARA Shigefumi  東北大学, 大学院・農学研究科, 教授 (30170145)

Co-Investigator(Kenkyū-buntansha) KIYOTA Hiromasa  東北大学, 大学院・農学研究科, 准教授 (30234397)
Co-Investigator(Renkei-kenkyūsha) IGARASHI Yasuhiro  富山県立大学, 工学部, 教授 (20285159)
Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2012: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2011: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2010: ¥7,670,000 (Direct Cost: ¥5,900,000、Indirect Cost: ¥1,770,000)
Keywords有機化学 / 有機合成化学 / 全合成 / cytotoxic / antitumor / lactimidomycin / oxylipin / pestaloquinol / BU-4664L / Sg17-1-4 / rumphellaone A / 細胞毒性 / 癌細胞転移阻害 / lupinacidin / aspergillide / rumphellaone / nigricanoside / tumor cell invasion / macrolide / alchivemycin / 浸潤阻害 / 不斉アルドール反応 / マクロライド
Research Abstract

Total syntheses of natural products with unique structural architectures as well as potent cytotoxicity and/or migration inhibitory activity against several cancer cell lines have been accomplished. Most of the syntheses were the fist examples of the total synthesis of the targeted molecules. Structure activity relationship study on lupinacidins, potent cancer cell migration inhibitors, led to the discovery of an analog which was comparable to lupinaidin C (most potent migration inhibitor among the three congeners) in activity.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (50 results)

All 2013 2012 2011 2010 Other

All Journal Article (17 results) (of which Peer Reviewed: 17 results) Presentation (30 results) Remarks (3 results)

  • [Journal Article] Enantioselective synthesis of hushinone, birkenol, and birkenal2013

    • Author(s)
      Takafumi Hirokawa, Shigefumi Kuwahara
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2013 Issue: 14 Pages: 2780-2782

    • DOI

      10.1002/ejoc.201300257

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of rumphellaone A via epoxy nitrile cyclization2012

    • Author(s)
      Takafumi Hirokawa, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron

      Volume: vol. 68 Issue: 24 Pages: 4581-4587

    • DOI

      10.1016/j.tet.2012.04.035

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of Lumphellaone A via Epoxy Nitrile Cyclization2012

    • Author(s)
      Hirokawa T.; Nagasawa, T.; Kuwahara, S.
    • Journal Title

      Tetrahedron Letters

      Volume: 53 Issue: 6 Pages: 705-706

    • DOI

      10.1016/j.tetlet.2011.11.145

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of a Protected Form of (6<I>R</I>,7<I>E</I>,9<I>S</I>,10<I>R</I>,12<I>Z</I>)-6,9,10-Trihydroxy-7,12-hexadecadienoic Acid2012

    • Author(s)
      Yusuke Kurashina, Shigefumi Kuwahara
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 76 Issue: 3 Pages: 605-607

    • DOI

      10.1271/bbb.110829

    • NAID

      10030751045

    • ISSN
      0916-8451, 1347-6947
    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Aspergillides A, B and C2012

    • Author(s)
      Nagasawa, T.; Kuwahara, S.
    • Journal Title

      Heterocycles

      Volume: 85 Issue: 3 Pages: 587-613

    • DOI

      10.3987/rev-12-727

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran2011

    • Author(s)
      Tomohiro Nagasawa, Tomoo Nukada, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron

      Volume: vol. 67 Issue: 16 Pages: 2882-2888

    • DOI

      10.1016/j.tet.2011.02.061

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of malyngic acid and fulgidic acid2011

    • Author(s)
      Yusuke Kurashina, Ayako Miura, Masaru Enomoto, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron

      Volume: vol. 67 Issue: 9 Pages: 1649-1653

    • DOI

      10.1016/j.tet.2011.01.005

    • Related Report
      2012 Final Research Report 2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Lupinacidin C, an inhibitor of tumor cell invasion from Micromonopora lupini2011

    • Author(s)
      Yasuhiro Igarashi, Saeko Yanase, Kohei Sugimoto, Masaru Enomoto, Satoshi Miyanaga, Martha E.Trujillo, Ikuo Saeki, Shigefumi Kuwahara
    • Journal Title

      Journal of Natural Products

      Volume: 74 Issue: 4 Pages: 862-865

    • DOI

      10.1021/np100779t

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Total Synthesis of the Potent Anti-HIV Nucleoside EFdA2011

    • Author(s)
      Kageyama, M.; Nagasawa, T.; Yoshida, M.; Ohrui, H.; Kuwahara, S.
    • Journal Title

      Organic Letters

      Volume: 13 Issue: 19 Pages: 5264-5266

    • DOI

      10.1021/ol202116k

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of N^1-and N^8-(γ-L-Glutamyl)spermidines and (γ-L-Glutamyl)putrescine2011

    • Author(s)
      Kazuya Toho, Naoki Abe, Teiko Yamada, Yoshifumi Ito, Hiroyuki Konno, Shigefumi Kuwahara, Hiromasa Kiyota
    • Journal Title

      Letters in Organic Chemistry

      Volume: 8 Pages: 1-4

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of lupinacidins A and B via sequential cycloaddition.double elimination2010

    • Author(s)
      Kohei Sugimoto, Masaru Enomoto,Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Lett

      Volume: vol. 51 Issue: 34 Pages: 4570-4572

    • DOI

      10.1016/j.tetlet.2010.06.121

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] 特異な複素環構造を有するバシロサルシンA,Bおよび関連化合物の合成研究2010

    • Author(s)
      榎本賢, 桑原重文
    • Journal Title

      有機合成化学協会誌

      Volume: 68 Pages: 387-398

    • NAID

      10026868671

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective total synthesis of idesolide via NaHCO_3-promoted dimerization2010

    • Author(s)
      Tomohiro Nagasawa, Naoyuki Shimada, Munefumi Torihata Shigefumi Kuwahara
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 4965-4969

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of lupinacidins A and B via sequential cycloaddition-double elimination2010

    • Author(s)
      Kohei Sugimoto, Masaru Enomoto, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 4570-4572

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the DEF-ring moiety of thiersine B2010

    • Author(s)
      Masaru Enomoto, Shigefumi Kuwahara
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 75 Pages: 6286-6289

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of pteroenonc and its stereoisomers, a defensive metabolite of the abducted Antarctic pteropod Clione antarctica2010

    • Author(s)
      Hiroki Asao, Yoko Nakamura, Yukito Furuya, Shigefumi Kuwahara, Bill J.Baker, Hiromasa Kiyota
    • Journal Title

      Helvetica Chimica Acta

      Volume: 93 Pages: 1933-1944

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Partial racemization occurring in the hydroxylactonizaton of a δ,ε-epoxy amide2010

    • Author(s)
      Masaru Enomoto, Shigefumi Kuwahara
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 74 Pages: 2535-2537

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Pestaloquinol A,BおよびCytosporin Dの全合成研究2013

    • Author(s)
      廣川高史,山真将,桑原重文
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内キャンパス
    • Year and Date
      2013-03-25
    • Related Report
      2012 Final Research Report
  • [Presentation] 癌細胞浸潤阻害物質BU-466Lの合成研究2013

    • Author(s)
      藤田聡美,渡邊麻衣,廣川高史,榎本賢,桑原重文
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内キャンパス
    • Year and Date
      2013-03-25
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] AI-77-BおよびSg17-1-4の合成研究2013

    • Author(s)
      鈴木智美,永沢友裕,榎本賢,桑原重文
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] Pestaloquinol A, BおよびCytosporin Dの全合成研究2013

    • Author(s)
      廣川高史,陰山真将, 桑原重文
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 癌細胞浸潤阻害物質lactimidomycinの全合成研究2013

    • Author(s)
      永沢友裕,桑原重文
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 血管新生阻害物質cortistatin A類の合成研究2013

    • Author(s)
      柴田要,佐藤勇気,山田てい子,桑原重文,清田洋正
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 抗腫瘍物質Maoecrystal Vの合成研究2013

    • Author(s)
      小竹正晃,浅尾洋樹,佐々木郁香,島崎泰治,桑原重文,清田洋正
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] Pestaloquinol A及びBの合成研究2012

    • Author(s)
      陰山真将, 桑原重文
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都女子大学(京都府)
    • Year and Date
      2012-03-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] Lactimidomycinの全合成研究2012

    • Author(s)
      永沢友裕, 桑原重文
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都女子大学(京都府)
    • Year and Date
      2012-03-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] Rumphellaone AおよびHushinoneの合成研究2012

    • Author(s)
      廣川高史, 桑原重文
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都女子大学(京都府)
    • Year and Date
      2012-03-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] Lactimidomycinの全合成研究2011

    • Author(s)
      永沢友裕, 桑原重文
    • Organizer
      第22回万有仙台シンポジウム
    • Place of Presentation
      仙台国際センター(宮城県)
    • Year and Date
      2011-12-19
    • Related Report
      2011 Annual Research Report
  • [Presentation] (+)-Rumphellaone Aの全合成2011

    • Author(s)
      廣川高史, 桑原重文
    • Organizer
      日本農芸化学会東北支部第146回大会
    • Place of Presentation
      山形大学農学部(山形県)
    • Year and Date
      2011-10-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] 強力な抗HIV活性を有するEFdAの全合成2011

    • Author(s)
      陰山真将, 永沢友裕, 吉田真弓, 大類洋, 桑原重文
    • Organizer
      日本農芸化学会東北支部第146回大会
    • Place of Presentation
      山形大学農学部(山形県)
    • Year and Date
      2011-10-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] 抗ガン物質cortistatin類のアナログ及びモデル合成研究2011

    • Author(s)
      柴田要, 佐藤勇気, 桑原重文, 清田洋正
    • Organizer
      日本農芸化学会東北支部第146回大会
    • Place of Presentation
      山形大学農学部(山形県)
    • Year and Date
      2011-10-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] 癌細胞浸潤阻害物質Lactimidomycinの全合成研究2011

    • Author(s)
      永沢友裕, 桑原重文
    • Organizer
      日本農芸化学会東北支部第146回大会
    • Place of Presentation
      山形大学農学部(山形県)
    • Year and Date
      2011-10-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] Lactimidomycinの全合成研究2011

    • Author(s)
      永沢友裕,桑原重文
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際交流センター
    • Year and Date
      2011-09-28
    • Related Report
      2012 Final Research Report
  • [Presentation] 抗HIV活性を有する4'Ed2FAの合成研究2011

    • Author(s)
      陰山真将, 吉田真弓, 永沢友裕, 榎本賢, 桑原重文
    • Organizer
      日本農芸化学会2011年度大会
    • Place of Presentation
      京都,京都女子大学
    • Year and Date
      2011-03-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] Maoecrystal Vの合成研究2011

    • Author(s)
      佐々木郁香, 浅尾洋樹, 島崎泰治, 桑原重文, 清田洋正
    • Organizer
      日本農芸化学会2011年度人会
    • Place of Presentation
      京都,京都女子大学
    • Year and Date
      2011-03-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] イネいもち病菌の生産する毒素ピリキュラリオールはラセミ体であった2011

    • Author(s)
      佐々木郁香, 田中功二, 兵藤孝次, 桑原重文, 鈴木雄二, 貫名学, 清田洋正
    • Organizer
      日本農薬学会第36回大会
    • Place of Presentation
      町田,玉川大学
    • Year and Date
      2011-03-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] 特異な環構造を有する生物活性天然物の全合成2010

    • Author(s)
      桑原重文
    • Organizer
      第54回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      山梨大学甲府キャンパス
    • Year and Date
      2010-10-24
    • Related Report
      2012 Final Research Report
  • [Presentation] 特異な環構造を有する生物活性天然物の全合成2010

    • Author(s)
      桑原重文
    • Organizer
      第54回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      甲府,山梨大学甲府キャンパス
    • Year and Date
      2010-10-24
    • Related Report
      2010 Annual Research Report
  • [Presentation] 抗HIV活性を有する4'Ed2FAの合成研究2010

    • Author(s)
      陰山真将, 吉田真弓, 永沢友裕, 榎本賢, 桑原重文
    • Organizer
      日本農芸化学会東北支部第145回大会
    • Place of Presentation
      仙台,東北大学農学研究科
    • Year and Date
      2010-09-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] Malyngic acidおよび12-epi-malyngic acidの合成研究2010

    • Author(s)
      倉科友輔, 二浦絢子, 永沢友裕, 榎本賢, 桑原重文
    • Organizer
      日本農芸化学会東北支部第145回大会
    • Place of Presentation
      仙台,東北大学農学研究科
    • Year and Date
      2010-09-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] 細胞毒性物質Sgl7-1-4の合成研究2010

    • Author(s)
      小関良卓, 曾之緯, 榎本賢, 桑原重文
    • Organizer
      日本農芸化学会東北支部第145回大会
    • Place of Presentation
      仙台,東北大学農学研究科
    • Year and Date
      2010-09-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] 特異な四環性セスキテルペノイドechinopine類の合成研究2010

    • Author(s)
      長島優太, 田中功二, 桑原重文, 史清文, 清田洋正
    • Organizer
      日本農芸化学会東北支部第145回大会
    • Place of Presentation
      仙台,東北大学農学研究科
    • Year and Date
      2010-09-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] 特異な環構造を有する生物活性天然物の合成研究2010

    • Author(s)
      桑原重文
    • Organizer
      平成22年度化学系学協会東北大会
    • Place of Presentation
      岩手大学工学部
    • Year and Date
      2010-09-25
    • Related Report
      2012 Final Research Report
  • [Presentation] 特異な環構造を有する生物活性天然物の合成研究2010

    • Author(s)
      桑原重文
    • Organizer
      平成22年度化学系学協会東北大会
    • Place of Presentation
      盛岡,岩手大学工学部
    • Year and Date
      2010-09-25
    • Related Report
      2010 Annual Research Report
  • [Presentation] (-)-idesolideの不斉全合成2010

    • Author(s)
      永沢友裕, 嶋田直之, 鳥羽田宗史, 桑原重文
    • Organizer
      第21回万有仙台シンポジウム
    • Place of Presentation
      仙台,仙台国際センター
    • Year and Date
      2010-06-05
    • Related Report
      2010 Annual Research Report
  • [Presentation] Malyngic acidおよびfulgidic acidの全合成2010

    • Author(s)
      倉科友輔, 三浦絢子, 永沢友裕, 榎本賢, 桑原重文
    • Organizer
      日本農芸化学会2011年度大会
    • Place of Presentation
      京都,京都女子大学
    • Year and Date
      2010-03-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] カバノキより単離された転位型カリオフィレン誘導体の全合成研究

    • Author(s)
      廣川高史,桑原重文
    • Organizer
      日本農芸化学会東北支部第147回大会
    • Place of Presentation
      弘前大学農学生命科学部
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2012 Final Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2010 Annual Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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