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Bioorganic Chemical Studies on Novel Sulfur-Containing Phytoalexins Produced by Crucifers

Research Project

Project/Area Number 63470019
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionHokkaido University

Principal Investigator

TAKASUGI Mitsuo  Hokkaido University, Faculty of Science, Professor, 理学部, 教授 (70000833)

Co-Investigator(Kenkyū-buntansha) MONDE Kenji  Hokkaido University, Faculty of Science, Instructor, 理学部, 助手 (40210207)
Project Period (FY) 1988 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥7,800,000 (Direct Cost: ¥7,800,000)
Fiscal Year 1990: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1989: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1988: ¥4,700,000 (Direct Cost: ¥4,700,000)
KeywordsCrucifer / Phytoalexin / Sulfur compound / Indole / Biosynthesis / biologically active compound / Glucosinolate / Isothiocyanate / 含硫化合物 / イソチオシアナ-ト / カブ / キャベツ / HPLC分析 / アブラナ科 / ハクサイ / ダイコン / ハクラン / イオウ原子
Research Abstract

(1) Several sulfur-containing phytoalexins have been isolated from cruciferous vegetables ; Chinese cabbage, cabbage, radish, and turnip. These phytoalexins, represented by brassinin, cyclobrassinin, and spirobrassinin, are characterized by the presence of indolic nucleus with the appendage containigone or two sulfur atoms.
(2) Time-course studies of cruciferous phytoalexins and glucosinolates have been carried out using UV-irradiated and non-irradiated turnip root tissues. Both of the levels of indole glucosinolates and phytoalexins increased in the UV-irradiated tissue whereas only the former did in non-irradiated control tissue. The levels of aliphatic glucosinolates decreased markedly both in the UV-irradiated and non-irradiated control tissues. Structural features of brassinins and indple glucosinolates suggest close biosynthetic relationships between two types of indoles. Additional parhway seems to be needed to induce the synthesis of phytoalexns.
(3) Biosynthetic pathway to cruciferous phytoalexins was investigated using UV-irradiated turnip and deuterium- or ^<13> C-labeled precursors : Tryptophan is a biological origin of the indole ring ; methyl portion of the methyothio groups of these phytoalexins originates from methionine ; molecular rearrangement would be involved in the pathway from tryprophan to brassinin ; transformation of benzyl isothiocyanate into brassinin-type compound in the tissue suggests that indo1-3-ylmethyl isothiocyanate, synthesized via indole glucosinolate or directly from tryptophan, would be a key intermediate in the biosynthesis of brassinin.
(4) Administration of artificial 2-methylbrassinin into UV-irradiated tissue resulted in the formation of an indoxyl and an indolenine derivative, suggesting 3-hydroxyindolenine or 2, 3-dihydroxyindole as a common intermediate to cyclobrassinin, dioxibrassinin, and spirobrassinin.
(5) A biosynthetic scheme starting from tryptophan to cruciferous phytoalexins is proposed.

Report

(4 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • 1988 Annual Research Report
  • Research Products

    (21 results)

All Other

All Publications (21 results)

  • [Publications] Kenji Monde: "Brassicanals A and B,Novel SulfurーContaining Phytoalexins from the Chinese Cabbage Brassica campestris L.ssp.pekinensis" Chemistry Letters. 209-210 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "4ーMethoxybrassinin,a SulphurーContaining Phytoalexin from Brassica oleracea" Phytochemistry. 29. 1499-1500 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "TimeーCourse Studies of Phytoalexins and Glucosinolates in UVーIrradiated Turnip Tissue" Z.Naturforsch.,C.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "Brassicanal C and Two Dioxindoles from Brassica oleracea var.capitt" Phytochemistry.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "Biosynthesis of Cruciferous Phytoalexins:Involvement of a Molecular Rearrangement in the Biosynthesis of Brassinin" J.Chem.Soc.Chem.Commun.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "Methoxybrassenins A and B,Two SulphurーContaining Stress Metabolites from Brassica oleracea" Phytochemistry.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "Brassicanals A and B, Novel Sulfur-Containing Phytoalexins from the Chinese Cabbage Brassica Campestris L. ssp. pekinensis" Chemistry Letters. 209-210 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "4-Methoxybrassinin, a Sulphur-Containing Phytoalexin from Brassica oleracea" Phytochemistry. 29. 1499-1500 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "Time-Course Studies of Phytoslexins and Glucosinolates in UV-Irradiatd Turnip Tissue" Z. Naturforsch.,. C.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "Brassicanal C and Two Dioxindoles from Brassica olerscea var capitata" Phytochemistry.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "Biosynthesis of Cruciferous Phytoalexins Involvement of a Molecular Rearrangement in the Biosysthesis of Brassinin" J. Chem. Soc. Chem. Commun.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "Methoxybrassenins A and B, Two Sulphur-Containing Stress Metaboletes from Brassica oleracea" Phytochemistry,.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Kenji Monde: "Brassicanals A and B,Novel SulfurーContaining Phytoalexins from the Chinese Cabbage <Brassica>___ー <campestris>___ー L.ssp.<pekinensis>___ー" Chemistry Letters. 209-210 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Kenji Monde: "4ーMethoxybrassinin,a SulphurーContaining phytoalexin from <Brassica>___ー <oleracea>___ー" Phytochemistry. 29. 1499-1500 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Kenji Monde: "TimeーCourse Studies of Phytoalexins and Glucosinolates in UVーIrradiated Turnip Tissue" Z.Naturforsch.,C.

    • Related Report
      1990 Annual Research Report
  • [Publications] Kenji Monde: "Brassicanal C and Two Dioxindoles from <Brassica>___ー <oleracea>___ー var.<capitata>___ー" Phytochemistry.

    • Related Report
      1990 Annual Research Report
  • [Publications] Kenji Monde: "Biosynthesis of Cruciferous Phytoalexins:Involvement of a Molecular Rearrangement in the Biosynthesis of Brassinin" J.Chem.Soc.Chem.Commun.

    • Related Report
      1990 Annual Research Report
  • [Publications] Kenji Monde: "Methoxybrassenins A and B,Two SulphurーContaining Stress Metabolites from <Brassica>___ー <oleracea>___ー" Phytochemistry.

    • Related Report
      1990 Annual Research Report
  • [Publications] Kenji Monde: "Brassicanals A and B,Novel Sulfur-Containing Phytoalexin from the Chinese Cabbage" Chemistry Letters. 209-210 (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kenji Monde: "4-Methoxybrassinin,a Sulphur-Containing Phytoalexin from Brassica oleracea" Phytochemistry. 28. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kenji,Monde: Chemistry Letters. (1989)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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