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METABOLIC FATE OF SECONDARY METABOLITES : INVOLVEMENT OF CELL WALLS

Research Project

Project/Area Number 17580095
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionKyoto University

Principal Investigator

ISHIHARA Atsushi  Kyoto University, GRADUATE SCHOOL OF AGRICULTURE, ASSISTANT PROFESSOR (80281103)

Project Period (FY) 2005 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥3,710,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥210,000)
Fiscal Year 2007: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2006: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2005: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordsoats / Arabidopsis thaliana / phytoalexin / secondary metabolism / cell wall / Laos (Lao P.D.R) / インドール-3-カルボン酸 / ファイトアレキシン / HPLC / アベナンスラミド
Research Abstract

The metabolic fates of secondary metabolites were investigated in gramineous plants, oats, and a model plant Arabidopsis thaliana.
In oats, it has been demonstrated that their phytoalesxins, avenanthramides, are incorporated into cell walls. lb know the incorporation processes in detail, the metabolites that are derived from avenanthramides were investigated. The avenanthramide metabolites that are genrerated by the action of peroxidase were found to be present in oat leaves. The analysis of their chemical structures revealed that they are dehydrodimers of avenanthramides. The spectroscopic analysis revealed that they have unique carbon skeletons that have not been found in natural products. These compounds are considered to be units for the incorporation of avenanthramides into cell walls.
In Arabidopsis thaliana, indole-3-carboxylic acid (ICA) has been indicated to bound to the cell walls. We found that the amount of ICA increases in the leaves infected by A. brassicicola. The biosynthetic pathway of ICA was analyzed by using stable isotope labeled putative precursors and mutants that exhibit modified tryptophan metabolism. First, Arabidopsis leaves were fed with labeled tryptophan and the conidia of A. brassicicola were inoculated. The leaves were extracted with methanol and the incorporation of tryptophan into ICA was analyzed by LC-MS/MS. The labeled tryptophan was effectively incorporated into ICA, indicating de novo synthesis of ICA in the infected leaves. Next, we analyzed ICA contents in multiple lines that have altered tryptophan metabolism. The increase of the amount of ICA in the cell walls was found in pad 3 mutant line. pad 3 line larks the accumulation of indolic phytoalexin, camalexin. Thus, this finding strongly suggests that ICA is not directly derived from camalexin, and that the biosynthetic pathway of ICA is shared by the pathway for camalexin.

Report

(4 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • 2005 Annual Research Report
  • Research Products

    (7 results)

All 2007 2006

All Journal Article (3 results) (of which Peer Reviewed: 2 results) Presentation (4 results)

  • [Journal Article] New dimeric compounds of avenanthramid phytoalexin in oats.2007

    • Author(s)
      Okazaki Y
    • Journal Title

      Journal of Organic Chemistry 72

      Pages: 3830-3839

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] New dimeric compounds of avenanthramide phytoalexin in oats2007

    • Author(s)
      Okazaki, Y
    • Journal Title

      Journal of Organic Chemistry 72

      Pages: 3830-3839

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] New dimeric compounds of avenanthramide phytoalexin in oats.2007

    • Author(s)
      Okazaki Y, Ishizuka A, Ishihara A, Nishioka T, Iwamura H
    • Journal Title

      Journal of Organic Chemistry 72

      Pages: 3830-3839

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] エンバクのファイトアレキシン,アベナンスラミド類の二量体の構造解析2006

    • Author(s)
      岡咲洋三
    • Organizer
      日本農薬学会第31回大会
    • Place of Presentation
      福岡工業大学、福岡市
    • Year and Date
      2006-03-22
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Structural elucidation of dimers of avenanthramide phytoalexins in oats2006

    • Author(s)
      Okazaki, Y
    • Organizer
      31th Annual Meeting of Japanese Society of Pesticide Sciences
    • Place of Presentation
      Fukuoka Institute of Technology, Fukuoka City
    • Year and Date
      2006-03-22
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Identification of dimers of avenanthramide phytoalexins in oats2006

    • Author(s)
      Ishihara A
    • Organizer
      11th IUPAC international Congress of Pesticide Chemistry
    • Place of Presentation
      神戸国際会議場,神戸市
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Identification of dimers of avenanthramide phytoalexins in oats2006

    • Author(s)
      Ishihara, A
    • Organizer
      11th IUPAC International Congress of Pesticide Chemistry
    • Place of Presentation
      Kobe International Conference Center, Kobe City
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary

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Published: 2005-04-01   Modified: 2016-04-21  

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