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Synthetic Studies on Anti-Mitotic Natural Products, Nigricanosides, and Their Artificial Analogues for Biological Evaluation

Research Project

Project/Area Number 24510289
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Living organism molecular science
Research InstitutionHokkaido University

Principal Investigator

FUJIWARA Kenshu  北海道大学, 理学(系)研究科(研究院), 准教授 (20222268)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords天然物合成化学 / 有糸分裂阻害 / ニグリカノシド / 人工類縁体 / 有機化学 / 立体選択的合成 / グリセロ糖脂質 / エーテル化合物 / 有糸分裂阻害剤 / 有機合成化学 / 部分構造合成 / エーテル合成
Outline of Final Research Achievements

Nigricanoseides, isolated from the green alga Avrainvillea nigricans, belong to a monogalactosyldiacylglycerol family and exhibit potent growth inhibition against cancer cells due to their anti-mitotic activity. 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 chemical synthesis of artificial analogues of nigricanoseide A dimethyl ester. As a result, a common method for the construction of the two ether linkages has been established, and several artificial analogues have been synthesized.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (3 results)

All 2015 2013

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (2 results)

  • [Journal Article] A stereoselective method for the construction of the C8'-O-C6" ether of nigricanoside-A: synthesis of simple models for the C20 lipid chain/galactosyl glycerol segment2013

    • Author(s)
      Naoto Kinashi
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 34 Pages: 4564-4567

    • DOI

      10.1016/j.tetlet.2013.06.085

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] ニグリカノシドAのC10-O-C11'エーテル結合部の立体選択的構築の検討2015

    • Author(s)
      藤原 憲秀、角田 隆幸、木梨 尚人、上遠野 亮、鈴木 孝紀
    • Organizer
      日本化学会第95年会(2015)
    • Place of Presentation
      日本大学(船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] ニグリカノシドAジメチルエステルの脂肪酸鎖間エーテル部の構築2013

    • Author(s)
      木梨尚人
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(草津市)
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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