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Combinatorial biosynthesis of triterpenoid using fungal cytochrome P450 monooxygenases

Research Project

Project/Area Number 16H04955
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Wood science
Research InstitutionKyushu University

Principal Investigator

Ichinose Hirofumi  九州大学, 農学研究院, 准教授 (00432948)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥16,900,000 (Direct Cost: ¥13,000,000、Indirect Cost: ¥3,900,000)
Fiscal Year 2018: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2017: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2016: ¥9,750,000 (Direct Cost: ¥7,500,000、Indirect Cost: ¥2,250,000)
KeywordsシトクロムP450 / トリテルペン / 糸状菌 / 担子菌 / テルペノイド / バイオテクノロジー / 微生物 / トリテルペノイド
Outline of Final Research Achievements

A functional screening of fungal cytochromes P450 for combinatorial biosynthesis of triterpenoids was conducted. To elucidate catalytic potentials of fungal P450s against plant triterpenoids, we generated recombinant yeasts that allow co-expression of fungal P450 and plant triterpene synthase. Based upon metabolic studies, we identified fungal P450s showing catalytic activities for plant triterpenoids lupeol and beta-amyrin, indicating a series of plant-like triterpenoids could be produced using fungal P450s. In addition, some basidiomycetous P450s were suggested to be capable of decorating steroid compounds appeared from steroid metabolism by yeast. These results suggested that basidiomycetes possess P450-dependent metabolic systems to generate various ergostane-type steroids.

Academic Significance and Societal Importance of the Research Achievements

トリテルペノイドは各種生物が産生する代謝物であり、薬理活性を示す化合物も多く知られている。一方で、自然界に産出される代謝産物の大量獲得は困難な現状であり、自然界に眠る“魅力あるトリテルペノイド”の利用には、これらを戦略的に合成する新しいバイオ技術の開発が重要な課題として残されている。本研究では、植物型トリテルペノイドの合成を可能とする糸状菌のシトクロムP450を同定した。本研究の成果は、自然界において稀少・有用なトリテルペノイドの戦略的合成を進展させるとともに、新奇な有用疑似天然物の発掘を加速すると期待される。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (18 results)

All 2019 2018 2017 2016

All Journal Article (4 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 4 results,  Open Access: 2 results) Presentation (14 results) (of which Int'l Joint Research: 5 results,  Invited: 1 results)

  • [Journal Article] Jianqiao Wang, Haruka Ohno, Yuuri Ide, Hirofumi Ichinose, Toshio Mori, Hirokazu Kawagishi, Hirofumi Hirai2019

    • Author(s)
      Identification of the cytochrome P450 involved in the degradation of neonicotinoid insecticide acetamiprid in Phanerochaete chrysosporium
    • Journal Title

      Journal of Hazardous Materials

      Volume: 371 Pages: 494-498

    • DOI

      10.1016/j.jhazmat.2019.03.042

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Insight into metabolic diversity of the brown-rot basidiomycete Postia placenta responsible for sesquiterpene biosynthesis: semi-comprehensive screening of cytochrome P450 monooxygenase involved in protoilludene metabolism2018

    • Author(s)
      Ichinose Hirofumi, Kitaoka Takuya
    • Journal Title

      Microbial Biotechnology

      Volume: 11 Issue: 5 Pages: 952-965

    • DOI

      10.1111/1751-7915.13304

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Biochemical Characterization of CYP505D6, a Self-Sufficient Cytochrome P450 from the White-Rot Fungus Phanerochaete chrysosporium2018

    • Author(s)
      Sakai Kiyota、Matsuzaki Fumiko、Wise Lisa、Sakai Yu、Jindou Sadanari、Ichinose Hirofumi、Takaya Naoki、Kato Masashi、Wariishi Hiroyuki、Shimizu Motoyuki
    • Journal Title

      Applied and Environmental Microbiology

      Volume: 84 Issue: 22

    • DOI

      10.1128/aem.01091-18

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Impacts of amino acid substitutions in fungal cytochrome P450 monooxygenase (CYP57B3) on the effective production of 3′-hydroxygenistein2017

    • Author(s)
      Mayumi Hatakeyama, Takuya Kitaoka, Hirofumi Ichinose
    • Journal Title

      FEMS Microbiology Letters

      Volume: 364 Issue: 11

    • DOI

      10.1093/femsle/fnx107

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Presentation] 糸状菌シトクロムP450の潜在機能を活用したトリテルペノイド生合成2019

    • Author(s)
      大園昂貴、一瀬博文、北岡卓也
    • Organizer
      第69回日本木材学会大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 褐色腐朽担子菌Postia placentaにおけるプロトイルデン型セスキテルペノイドの生合成機構2019

    • Author(s)
      木村紘也、一瀬博文、北岡卓也
    • Organizer
      第69回日本木材学会大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 糸状菌シトクロムP450の機能多様性とテルペノイドのコンビナトリアル生合成2018

    • Author(s)
      大園 昂貴, 筌場 将太, 北岡 卓也, 一瀬 博文
    • Organizer
      第70回日本生物工学会大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Idenfitication of cytochrome P450 monooxygenases responsible for terpene biosynthesis by basidiomycetes2018

    • Author(s)
      Hirofumi Ichinose
    • Organizer
      The 14th International Symposium on Cytochrome P450 Biodiversity and Biotechnology
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 出芽酵母を宿主とした担子菌型セスキテルペノイドのコンビナトリアル生合成2018

    • Author(s)
      筌場将太、一瀬博文、北岡卓也
    • Organizer
      第68回日本木材学会大会(京都大会)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 担子菌シトクロムP450の異種発現が及ぼす酵母の代謝物変動2017

    • Author(s)
      熊丸さち、一瀬博文、北岡卓也
    • Organizer
      第67回日本木材学会大会
    • Place of Presentation
      福岡
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] 木材腐朽菌 Phanerochaete chrysosporium が有するセスキテルペン合成酵素の多様性2017

    • Author(s)
      筌場将太、一瀬博文、北岡卓也
    • Organizer
      第67回日本木材学会大会
    • Place of Presentation
      福岡
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] Studies on terpene synthases and cytochrome P450 monooxygenases of basidiomycetes2017

    • Author(s)
      Ichinose Hirofumi, Ukeba Shota
    • Organizer
      20th International conference on cytochrome P450, biochemistry, biophysics and biotechnology
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Diversity of sesquiterpene synthase from the white-rot basidiomycete Phanerochaete chrysosporium2016

    • Author(s)
      Ukeba S., Kitaoka T., Ichinose H.
    • Organizer
      The 22nd Symposium of Young Asian Biological Engineers' Community
    • Place of Presentation
      Miyazaki, Japan
    • Year and Date
      2016-10-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] シトクロムP450 BM3と補酵素再生系の近接配置による酵素反応2016

    • Author(s)
      畠山真由美、野北昂志、北岡卓也、一瀬博文
    • Organizer
      第68回日本生物工学会大会
    • Place of Presentation
      富山
    • Year and Date
      2016-09-28
    • Related Report
      2016 Annual Research Report
  • [Presentation] 白色腐朽菌 Phanerochaete chrysosporium が有するセスキテルペン合成酵素の同定および機能解析2016

    • Author(s)
      筌場将太、北岡卓也、一瀬博文
    • Organizer
      第68回日本生物工学会大会
    • Place of Presentation
      富山
    • Year and Date
      2016-09-28
    • Related Report
      2016 Annual Research Report
  • [Presentation] Functionalization of fungal cytochrome P450 in Escherichia coli2016

    • Author(s)
      Ichinose H.
    • Organizer
      13th International Symposium on Cytochrome P450 Biodiversity and Biotechnology
    • Place of Presentation
      Vancouver, Canada
    • Year and Date
      2016-07-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Heterologous expression and functionalization of fungal cytochromes P450 (CYP5136A1 and CYP5136A3) in Escherichia coli2016

    • Author(s)
      Hatakeyama M., Kitaoka T., Ichinose H.
    • Organizer
      13th International Symposium on Cytochrome P450 Biodiversity and Biotechnology
    • Place of Presentation
      Vancouver, Canada
    • Year and Date
      2016-07-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 担子菌由来シトクロムP450 (CYP5136A1, CYP5136A3) の異種発現およびシトクロムb5による機能発現2016

    • Author(s)
      畠山真由美、北岡卓也、一瀬博文
    • Organizer
      第16回日本蛋白質科学会年会
    • Place of Presentation
      福岡
    • Year and Date
      2016-06-07
    • Related Report
      2016 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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