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Elucidation and controlment of diverse structure in the biosynthesis of indole diterpene

Research Project

Project/Area Number 16K16636
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Biomolecular chemistry
Research InstitutionHokkaido University

Principal Investigator

Liu Chengwei  北海道大学, 理学研究院, 助教 (60773801)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsbiosynthesis / indole diterpene / Indole sesquiterpene / shearinine / sespendole / Biosynthesis / 生合成
Outline of Final Research Achievements

Indole terpenes are a large class of fungal natural product. In this study, we used Aspergillus oryzea heterologous expression system to express shearinine and sespendole biosynthetic genes. ①The late-stage biosynthetic pathway of the shearinine involving four enzymatic reaction was elucidated by heterologous expression in A. oryzae. When incubated this transformants with the corresponding intermediates, we found that shearinine D was produced. In vitro enzymatic reaction with a recombinant protein, we elucidated the key oxidative cyclization, forming a characteristic 6/5 bicyclic of shearinine by flavoprotein oxidase. ② Sespendole biosynthetic gene cluster were identified. The biosynthetic pathway that involves genes encoding six enzymes was elucidated through heterologous expression of spd genes in A. oryzae. Thereby, revealing the mechanism underlying the characteristic modification on the indole ring, catalyzed by a set of prenyltransferase (SpdE)/cytochrome P450 (SpdJ) enzymes.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (8 results)

All 2018 2017 2016 Other

All Int'l Joint Research (1 results) Journal Article (1 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 1 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (3 results) (of which Int'l Joint Research: 1 results) Book (1 results) Remarks (2 results)

  • [Int'l Joint Research] Institute of Fundamental Sciences/Massey University(New Zealand)

    • Related Report
      2016 Research-status Report
  • [Journal Article] Biosynthesis of shearinine: Diversification of a tandem prenyl moiety of fungal indole diterpenes2016

    • Author(s)
      Liu, C.; Minami, A.; Dairi, T.; Gomi, K.; Scott, B.; Oikawa, H.
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 19 Pages: 5026-5029

    • DOI

      10.1021/acs.orglett.6b02482

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] 糸状菌が生産するインドールセスキテルペンの生合成研究(3)2018

    • Author(s)
      工藤洸星・松本知之・劉成偉・尾﨑太郎・ 五味勝也・南篤志・及川 英秋
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 糸状菌が生産するインドールセスキテルペンの生合成研究(2)2017

    • Author(s)
      工藤洸星・松本知之・劉成偉・尾﨑太郎・ 五味勝也・南篤志・及川英秋
    • Organizer
      日本化学会 第97春季年会 (2017)
    • Place of Presentation
      慶應義塾大学(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] Study on the biosynthesis of fungal indole diterpenes2017

    • Author(s)
      Chengwei Liu
    • Organizer
      2nd US-Japan Seminar on the Biosynthesis of Natural Products for Young Researchers
    • Place of Presentation
      東京工業大学(東京都・目黒区)
    • Year and Date
      2017-03-04
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Book] 酵母菌・麹菌・乳酸菌の産業応用展開2018

    • Author(s)
      南 篤志、劉 成偉、尾﨑太郎、及川英秋
    • Total Pages
      264
    • Publisher
      シーエムシー出版
    • ISBN
      9784781313177
    • Related Report
      2017 Annual Research Report
  • [Remarks]

    • URL

      http://barato.sci.hokudai.ac.jp/~yuhan/

    • Related Report
      2017 Annual Research Report
  • [Remarks] https://wwwchem.sci.hokudai.ac.jp/~yuhan/

    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2019-03-29  

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