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Revealing the mechanism of ring expansion reaction to tropolon formation uniquely found in woody plant.

Research Project

Project/Area Number 24580248
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Wood science
Research InstitutionKyushu University

Principal Investigator

FUJITA Koki  九州大学, (連合)農学研究科(研究院), 助教 (90264100)

Co-Investigator(Kenkyū-buntansha) TSUTSUMI Yuji  九州大学, 大学院農学研究院, 教授 (30236921)
Co-Investigator(Renkei-kenkyūsha) ICHINOSE Hirofumi  九州大学, 大学院農学研究院, 准教授 (00432948)
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: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywordsヒノキチオール / トロポロン環 / テルピノレン / GCMS / P450 / ジオキシゲナーゼ / テルペン / Cupressus lusitanica / トロポロン / P450 / メキシコイトスギ / 重水素ラベル / エポキシ / 生合成 / モノテルペン
Outline of Final Research Achievements

Feeding experiment with deuterized terpinolene into Cupressus lusitanica cultured cell revealed that terpinolene is the first olefin monoterpene intermediate to biosynthesize beta-thujaplicin. This pathway was the first report that tropolon ring was formed from terpenoid.
Serching other intermediates by comparing GCMS analysis of extractives from normal and deuterized terpinolene fed to the cell did not give the good candidate of the intermediates. Therefore, we should consider another pathway driven by dioxygenase.

Report

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

    (8 results)

All 2014 2013 2012

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 1 results) Presentation (5 results)

  • [Journal Article] Stereo-selective oxidations of terpinolene by cytochrome P450 monooxygenases in the microsomal fraction of Cupressus lusitanica cultured cells2014

    • Author(s)
      Takako Harada, Koki Fujita, Jun Shigeto, Yuji Tsutsumi
    • Journal Title

      Journal of Wood Science

      Volume: 60 Issue: 6 Pages: 446-452

    • DOI

      10.1007/s10086-014-1432-0

    • NAID

      40020303246

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A novel synthetic pathway for tropolone ring formation via the olefin monoterpene intermediate terpinolene in cultured Cupressus lusitanica cells2014

    • Author(s)
      Koki Fujita, Yasufumi Bunyua, Ken’ich Kurodaa, Tatsuya Ashitanib, Jun Shigetoa, Yuji Tsutsumi
    • Journal Title

      Journal of Plant Physiology

      Volume: 171 Issue: 8 Pages: 610-614

    • DOI

      10.1016/j.jplph.2013.12.016

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Regio- and Substrate-specific Oxidative Metabolism of Terpinolene by Cytochrome P450 Monooxygenases in Cupressus lusitanica Cultured Cells2012

    • Author(s)
      Takako Harada, et al
    • Journal Title

      American Journal of Plant Science

      Volume: 3-2 Issue: 02 Pages: 268-275

    • DOI

      10.4236/ajps.2012.32032

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] d6 - ラベル化テルピノレン投与による Cupressus lusitanica でのヒノキチ オール生合成中間体の探索2014

    • Author(s)
      藤村隼人,藤田弘毅,堤祐司
    • Organizer
      第 21 回日本木材学会 九州支部大会
    • Place of Presentation
      熊本
    • Year and Date
      2014-09-11 – 2014-09-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] テルピノレンはヒノキチオール生合成中間体である2013

    • Author(s)
      豊丹生泰史,藤田弘毅,黒田健一,芦谷竜矢,堤 祐司
    • Organizer
      第63回日本木材学会大会(盛岡)
    • Place of Presentation
      盛岡
    • Related Report
      2012 Research-status Report
  • [Presentation] Cuplessus lusitanica培養細胞における炭化水素モノテルペンを介したシグナル伝達2013

    • Author(s)
      神戸 良,藤田弘毅,堤 祐司
    • Organizer
      第63回日本木材学会大会(盛岡)
    • Place of Presentation
      盛岡
    • Related Report
      2012 Research-status Report
  • [Presentation] Terpinolene is the first olefin monoterpene intermediate to a tropolone, β- thujaplicin; - Potential novel pathway to tropolone ring -2013

    • Author(s)
      Koki Fujita,Yasufumi Bunyu, Ken’ichi Kuroda, Tatsuya Ashitani, Yuji Tsutsumi
    • Organizer
      TERPNET 2013
    • Place of Presentation
      Kolymvari, Greece
    • Related Report
      2012 Research-status Report
  • [Presentation] The relationship between the time courses of the β-thujaplicin production and of the activities of terpinolene oxygenases in Cupressus lusitanica cultured cells2012

    • Author(s)
      TAKAKO HARADA, KOKI FUJITA AND YUJI TSUTSUMI
    • Organizer
      28th International Society of Chemical Ecology
    • Place of Presentation
      Vilnius, Lithuania
    • Related Report
      2012 Research-status Report

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

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