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Synthetic and Structural Studies on Bioactive Natural Products

Research Project

Project/Area Number 22580115
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

ISHIGAMI Ken  東京大学, 大学院・農学生命科学研究科, 准教授 (70292787)

Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2010: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords有機化学 / 天然物化学 / 立体化学 / 抗ピロリ菌 / セスキテルペン / ラジカル環化 / ラジカル環化反応 / Topsentolide / 抗腫瘍活性 / 有機合成化学 / 有機合成 / Ma jusculoic acid
Research Abstract

Synthetic studies on bioactive natural products, which could be new drugs, were carried out in order to determine their stereochemistry. A new sesquiterpene, potent inhibitor of H. pylori growth, was efficiently synthesized as a racemate via tandem radical cyclization. The stereochemistry of topsentolide A was determined by synthesis of their possible stereoisomers, and cytotoxicity of the synthetic isomers was examined. About Majusculoic acid, a novel antifungal drug, new method to prepare the chiral building block was established.

Report

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

    (38 results)

All 2013 2012 2011 2010 Other

All Journal Article (13 results) (of which Peer Reviewed: 11 results) Presentation (22 results) (of which Invited: 1 results) Remarks (3 results)

  • [Journal Article] Total synthesis of (±)-lysidicin A.2012

    • Author(s)
      Y. Ogura, K. Ishigami, H. Watanabe
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 1723-1728

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] 最新のトピックス 「フローケミストリーでマラリアを克服!?」2012

    • Author(s)
      K. Ishigami
    • Journal Title

      化学

      Volume: 67 Pages: 68-69

    • Related Report
      2012 Annual Research Report
  • [Journal Article] Total synthesis of (±)-lysidicin A2012

    • Author(s)
      Y.Ogura
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 1723-1728

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 天然物化学における有機合成.2011

    • Author(s)
      K. Ishigami
    • Journal Title

      Annual Report 2010 (Cryogenic Research Center, The University of Tokyo)

      Volume: 2 Pages: 32-38

    • Related Report
      2012 Final Research Report
  • [Journal Article] Determination of the absolute configuration of marine oxylipin topsentolide A by the synthesis of theenantiomer of the natural product.2010

    • Author(s)
      M. Kobayashi, K. Ishigami, H. Watanabe;
    • Journal Title

      Tetrahedron Lett.

      Volume: 51(1) Pages: 2762-2764

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Determination of the absolute configuration of nodulisporacid A by the concise synthesis of four stereoisomers via three-component reaction and one-pot construction of the framework.2010

    • Author(s)
      T. Sumiya, K. Ishigami, H. Watanabe
    • Journal Title

      Tetrahedron Lett

      Volume: 51 Pages: 2765-2767

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Total Synthsis of (±)-Urechitol A2010

    • Author(s)
      T. Sumiya, K. Ishigami, H. Watanabe
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 49 Pages: 5527-5528

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (2RS,8R,10R)-YM-193221 and an improved approach to tyroscherin, bioactive natural compounds from Pseudallescheria sp2010

    • Author(s)
      R. Katsuta, A. Yajima, K. Ishigami, T. Nukada, H. Watanabe;
    • Journal Title

      Biosci. Biotechnol. Biochem

      Volume: 74 Pages: 2056-2059

    • NAID

      10027560555

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Determination of the absolute configuration of marine oxylipin topsentolide A_1 by the synthesis of the enantiomer of the natural product.2010

    • Author(s)
      M.Kobayashi
    • Journal Title

      Tetrahedron Lett.

      Volume: 51 Pages: 2762-2764

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Determination of the absolute configuration of nodulisporacid A by the concise synthesis of four stereoisomers via three-component reaction and one-pot construction of the framework.2010

    • Author(s)
      T.Sumiya
    • Journal Title

      Tetrahedron Lett.

      Volume: 51 Pages: 2765-2767

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Total Synthsis of (±)-Urechitol A.2010

    • Author(s)
      T.Sumiya
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: 49 Pages: 5527-5528

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Spliceostatin A blocks angiogenesis by inhibiting global gene expression including VEGF.2010

    • Author(s)
      R.Furumai
    • Journal Title

      Cancer Sci.

      Volume: 101 Pages: 2483-2489

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (2RS, 8R, 10R)-YM-193221 and an improved approach to tyroscherin, bioactive natural compounds from Pseudallescheria sp.2010

    • Author(s)
      R.Furumai
    • Journal Title

      Biosci.Biotechnol.Biochem.

      Volume: 74 Pages: 2056-2059

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] GlabramycinCの立体化学の決定を目的とした合成研究.2013

    • Author(s)
      山本 将起、石神 健、渡邉 秀典;
    • Organizer
      日本農芸化学会 2013 年度大会
    • Place of Presentation
      仙台
    • Year and Date
      2013-03-26
    • Related Report
      2012 Final Research Report
  • [Presentation] Efficient synthesis of (±)-(Z)-2 β- hydroxy-14-hydro-β-santalol employing tandem radical cyclization.2012

    • Author(s)
      K. Ishigami;
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry (
    • Place of Presentation
      Kyoto
    • Year and Date
      2012-11-13
    • Related Report
      2012 Final Research Report
  • [Presentation] Syntheses of Natural Anti-cancer and Anti-infective Agents, Topsentolide A and (Z)-2 β -Hydroxy-14-hydro- β-santalol.2012

    • Author(s)
      K. Ishigami;
    • Organizer
      The 13th International Symposium on Natural Product Chemistry
    • Place of Presentation
      Karachi, Pakistan
    • Year and Date
      2012-09-22
    • Related Report
      2012 Final Research Report
  • [Presentation] ラジカル環化反応を用いたサンタロール誘導体の合成研究.2012

    • Author(s)
      山田 慎也、石神 健、渡邉 秀典;
    • Organizer
      日本農芸化学会 2012 年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-24
    • Related Report
      2012 Final Research Report
  • [Presentation] ラジカル環化反応を用いたサンタロール誘導体の合成研究2012

    • Author(s)
      山田慎也
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] 生合成仮説に基づく(-)-Chamobtusin Aの合成2012

    • Author(s)
      森直紀
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] (+)-Anthecularinの不斉全合成2012

    • Author(s)
      小倉由資
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] 抗マラリア原虫活性を有するセスキテルペンの合成研究2011

    • Author(s)
      迫田大地
    • Organizer
      第55回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      つくば
    • Year and Date
      2011-11-19
    • Related Report
      2011 Annual Research Report
  • [Presentation] エーテル環の立体制御を軸とした生物活性天然物の合成2011

    • Author(s)
      小倉由資
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪
    • Year and Date
      2011-09-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] Enantioselective synthesis and determination of the absolute configurations of marine oxylipin topsentolide A.2010

    • Author(s)
      K. Ishigami, M.
    • Organizer
      Kobayashi, H. Watanabe; PACIFICHEM 2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-18
    • Related Report
      2012 Final Research Report
  • [Presentation] Enantioselective synthesis and determination of the absolute configurations of marine oxylipin topsentolide A_1.2010

    • Author(s)
      K.Ishigami
    • Organizer
      PACIFICHEM 2010
    • Place of Presentation
      Honolulu(米国)
    • Year and Date
      2010-12-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Enantioselective syntheses and determination of the absolute configurations of anti-cancer agents, tyroscherin and topsentolide A.2010

    • Author(s)
      K. Ishigami;
    • Organizer
      Bangladesh Chemical Congress 2010
    • Place of Presentation
      Dhaka, Bangladesh.
    • Year and Date
      2010-12-12
    • Related Report
      2012 Final Research Report
  • [Presentation] Enantioselective syntheses and determination of the absolute configurations of anti-cancer agents, tyroscherin and topsentolide A_1.2010

    • Author(s)
      K.Ishigami
    • Organizer
      Bangladesh Chemical Congress 2010
    • Place of Presentation
      Dhaka(バングラディシュ)
    • Year and Date
      2010-12-12
    • Related Report
      2010 Annual Research Report
  • [Presentation] Synthesis and structure revision of tyroscherin, a growth inhibitor of IGF-1-dependent tumor cells2010

    • Author(s)
      K. Ishigami, R. Katsuta, H. Watanabe, T. Kitahara
    • Organizer
      The 5th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Hsinchu, Taiwan
    • Year and Date
      2010-11-09
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis and structure revision of tyroscherin, a growth inhibitor of IGF-1-dependent tumor cells.2010

    • Author(s)
      K.Ishigami
    • Organizer
      The 5th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Hsinchu(台湾)
    • Year and Date
      2010-11-08
    • Related Report
      2010 Annual Research Report
  • [Presentation] 抗ピロリ菌活性セスキテルペンの合成研究.2010

    • Author(s)
      山田慎也、石神 健、渡邉秀典
    • 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
    • Year and Date
      2010-10-23
    • Related Report
      2012 Final Research Report
  • [Presentation] ラジカル環化反応を用いた抗ピロリ菌活性セスキテルペンの合成研究2010

    • Author(s)
      山田 慎也、石神 健、渡邉 秀典
    • Organizer
      日本農芸化学会関東支部2010年度大会
    • Place of Presentation
      千葉
    • Year and Date
      2010-10-09
    • Related Report
      2012 Final Research Report
  • [Presentation] Syntheses of Natural Anti-cancer and Anti-infective Agents, Topsentolide A1 and (Z)-2β-Hydroxy-14-hydro-β-santalol.

    • Author(s)
      K. Ishigami
    • Organizer
      The 13th International Symposium on Natural Product Chemistry
    • Place of Presentation
      カラチ(パキスタン)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Efficient synthesis of (±)-(Z)-2β-hydroxy-14-hydro-β-santalol employing tandem radical cyclization.

    • Author(s)
      K. Ishigami
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      リーガロイヤルホテル京都(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Glabramycin C の立体化学の決定を目的とした合成研究

    • Author(s)
      山本 将起
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内北キャンパス(宮城県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Okundoperoxideの合成研究

    • Author(s)
      迫田 大地
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内北キャンパス(宮城県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] アザジラクチンの全合成研究 -右側ジヒドロフランアセタール部を中心に-

    • Author(s)
      森 直紀
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学川内北キャンパス(宮城県)
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://park.itc.u-tokyo.ac.jp/org-chem/

    • Related Report
      2012 Final Research Report
  • [Remarks] 東京大学有機化学研究室

    • URL

      http://park.itc.u-tokyo.ac.jp/org-chem/

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://park.itc.u-tokyo.ac.jp/org-chem/

    • Related Report
      2011 Annual Research Report

URL: 

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

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