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Synthetic Studies on Novel, Natural Anti-Mitotic Agents, Nigricanosides, toward Elucidation of Their Stereochemistry and Biological Activity

Research Project

Project/Area Number 21510218
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Living organism molecular science
Research InstitutionHokkaido University

Principal Investigator

FUJIWARA Kenshu  北海道大学, 大学院・理学研究院, 准教授 (20222268)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2011: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2010: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2009: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords生物活性分子の設計 / 合成 / グリセロ糖脂質 / 立体構造解明 / ニグリカノシAジメチルエステル / 立体選択的合成 / 全合成 / エーテル結合性脂質 / 酸化脂質 / 有糸分裂阻害剤 / ニグリカノシドAジメチルエステル / 有糸分裂阻害物質
Research Abstract

Nigricanoseides, isolated from the green alga Avrainvillea nigricans, belong to a monogalactosyldiacylglycerol family and exhibit potent growth inhibitory activity against cancer cells. Because of the scarce supply from natural source and the unknown stereochemistry, nigricanosides are not explored biologically in detail. Therefore, studies aiming at the elucidation of their stereochemistry and biological activity have commenced with the partial synthesis of a congener, nigricanoseide A dimethyl ester. As a result, methods for the construction of the two ether linkages have been established, and the stereochemistry of the ether junction between the galactose moiety and the lower acyl chain has been clarified.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (15 results)

All 2011 2010 2009

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (8 results)

  • [Journal Article] Improved synthesis of C8-C20 segmentof pectenotoxin-2.2011

    • Author(s)
      Kenshu Fujiwara, Yuki Suzuki, Nao Koseki, Shun-ichi Murata, Akio Murai, Hidetoshi Kawai, and Takanori Suzuki
    • Journal Title

      Tetrahedron Lett

      Volume: 52,(43) Issue: 43 Pages: 5589-5592

    • DOI

      10.1016/j.tetlet.2011.08.051

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of theC22-C37 segment of prorocentin.2011

    • Author(s)
      Atsushi Takemura, Yasushi Katagiri, Kenshu Fujiwara, Hidetoshi Kawai, and Takanori Suzuki
    • Journal Title

      Tetrahedron Lett

      Volume: 52,(11) Issue: 11 Pages: 1222-1224

    • DOI

      10.1016/j.tetlet.2011.01.042

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the C22-C37 segment of prorocentin2011

    • Author(s)
      Kenshu Fujiwara
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Pages: 1222-1224

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Model studies for the stereoselective construction of the BC-ring of armatol F based on Ireland-Claisen rearrangement and relay ring-closing olefin metathesis.2010

    • Author(s)
      Kenshu Fujiwara, Keita Tanaka, Yasushi Katagiri, Hidetoshi Kawai, and Takanori Suzuki
    • Journal Title

      Tetrahedron Lett

      Volume: 51,(34) Issue: 34 Pages: 4543-4546

    • DOI

      10.1016/j.tetlet.2010.06.103

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Studies toward the total synthesis of armatol F : stereoselective construction of the C6 and C7 stereocenters and formation of the A-ring skeleton.2010

    • Author(s)
      Kenshu Fujiwara, Yuta Hirose, Daisuke Sato, Hidetoshi Kawai, and Takanori Suzuki
    • Journal Title

      Tetrahedron Lett

      Volume: 51,(32) Issue: 32 Pages: 4263-4266

    • DOI

      10.1016/j.tetlet.2010.06.026

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Model studies for the stereoselective construction of the BC-ring of armatol F based on Ireland-Claisen rearrangement and relay ring-closing olefin metathesis2010

    • Author(s)
      Kenshu Fujiwara
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 4543-4546

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Studies toward the total synthesis of armatol F : stereoselective construction of the C6 and C7 stereocenters and formation of the A-ring skeleton2010

    • Author(s)
      Kenshu Fujiwara
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 4263-4266

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] ニグリカノシドAジメチルエステルの合成研究2011

    • Author(s)
      木梨尚人、藤原憲秀、河合英敏、鈴木孝紀
    • Organizer
      化学系学協会北海道支部2011年夏季研究発表会講演要旨集B05
    • Place of Presentation
      室蘭工業大学、室蘭
    • Year and Date
      2011-07-23
    • Related Report
      2011 Final Research Report
  • [Presentation] ニグリカノシドAジメチルエステルの合成研究2011

    • Author(s)
      木梨尚人、藤原憲秀
    • Organizer
      日本化学会北海道支部2011年夏季研究発表会
    • Place of Presentation
      室蘭工業大学(室蘭市)
    • Year and Date
      2011-07-23
    • Related Report
      2010 Annual Research Report
  • [Presentation] ニグリカノシドAジメチルエステルの合成研究2011

    • Author(s)
      木梨尚人、藤原憲秀、河合英敏、鈴木孝紀
    • Organizer
      日本化学会第91春季年会講演要旨集1A1-31
    • Place of Presentation
      神奈川大学横浜キャンパス、横浜(東日本大震災のため要旨集公開のみを以て発表成立)
    • Year and Date
      2011-03-26
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthetic Studies on Nigricanoside A Dimethyl Ester (2) : An Approach to Construct the Ether Linkage between the Lipid Chains2010

    • Author(s)
      Kenshu Fujiwara, Ayako Kawai, Naoto Kinashi, Hidetoshi Kawai, and Takanori Suzuki
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies Abstract Book 1901
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthetic Studies on Nigricanoside A Dimethyl Ester (1) : Construction of the Ether Linkage between the Galactose Moiety and the C20 Lipid Chain2010

    • Author(s)
      Naoto Kinashi, Kenshu Fujiwara, Hidetoshi Kawai, and Takanori Suzuki
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies Abstract Book 1904
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2011 Final Research Report
  • [Presentation] エーテル結合性グリセロ糖脂質の合成研究2010

    • Author(s)
      藤原憲秀、木梨尚人、河合英敏、鈴木孝紀
    • Organizer
      日本化学会第90春季年会講演要旨集3A5-30
    • Place of Presentation
      近畿大学本部キャンパス、東大阪
    • Year and Date
      2010-03-28
    • Related Report
      2011 Final Research Report
  • [Presentation] エーテル結合性グリセロ糖脂質の合成研究2010

    • Author(s)
      藤原憲秀
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス(東大阪市)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] エーテル結合性糖脂質の合成研究2009

    • Author(s)
      木梨尚人、藤原憲秀、河合英敏、鈴木孝紀
    • Organizer
      化学系学協会北海道支部2009年夏季研究発表会講演要旨集A08
    • Place of Presentation
      苫小牧工業高等専門学校、苫小牧
    • Year and Date
      2009-07-11
    • Related Report
      2011 Final Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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