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C3 unit addition reaction accompanied by formation of C-C bond in phytotoxin biosynthesis of phytopathogen.

Research Project

Project/Area Number 11660111
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

NAKAJIMA Hiromitsu  Tottori University, Faculty of Agriculture, Professor, 農学部, 教授 (40144646)

Co-Investigator(Kenkyū-buntansha) 中島 廣光  鳥取大学, 農学部, 教授 (40144646)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2000: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1999: ¥2,400,000 (Direct Cost: ¥2,400,000)
Keywordsplant pathogens / phytotoxins / biosynthesis / Bipolaris sorokiniana / sesquiterpene / ^<14>C labeled compound / ^3H labeled compound / GCMS / ^<18>O標識化合物
Research Abstract

Sorokinianin is a phytotoxin produced by a strain (OB-25-1) of Bipolaris sorokiniana, a pathogen causing spot blotch or foot and root rot diseases of wheat and other grasses. This toxin is assumed to be composed of a helminthosporol-type sesquiterpene and a C_3 portion. The feeding experiments conducted previously suggested that sorokinianin was synthesized from prehelminthosporol by reactions that include the addition of a member of the TCA cycle, decarboxylation and lactonization. A feeding experiment with L-[hydroxy-^<18>O] malic acid indicated that the direct C_3 unit precursor was not malic acid/oxalacetic acid but fumaric acid/succinic acid. The aim of this research is to identify the product formed just after addition of fumaric acid/succinic acid to prehelminthosporol. For this purpose we prepared ^<14>C labeled prehelminthosporol (1.7 mg, specific radioactivity 35 KBq/mg) from B.sorokiniana cultured on the medium containing ^<14>C labeled glucose. Among the fractions obtained from the mycelium incubated with both ^<14>C labeled prehelminthosporol and ^3H labeled succinic acid we found a fraction which had both ^<14>C and ^3H radioactivity. Then we analyzed the same fraction obtained in the cold run as in the radio isotopic experiment by GCMS after acetylation and methylation.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] F.Furumoto: "Biosynthesis of phytotoxin neovasinin and its related metabolites, neovasipyrones A and B and neovasifuranones A and B, in the phytopathogenic fungus Neocosmospora vasinfecta"J.Chem.Soc.,Perkin Trans.1. 1999. 131-135 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] P.Singh: "Purification and biological characterization of host-specific SV-toxins from Stemphylium vesicarium causing brown spot of European pear"Phytopathology. 89. 947-953 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Fujii: "Zygosporin D and two new cytochalasins produced by the fungus Metarrhizium anisopliae"Journal of Natural Products. 63. 132-135 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] P.Singh: "Effects of host-selective SV-toxin from Stemphylium vesicarium, the cause of brown spot of European pear plants, on ultrastructure of leaf cells"J.Phytopathology. 148. 87-93 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] E.Sakuno: "A new inhibitor of 5'-hydroxyaverantin dehydrogenase, an enzyme involved in aflatoxin biosynthesis, from Trichoderma hamatum"Journal of Natural Products. 63. 1677-1678 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Furumoto: "Biosynthesis of phytotoxin neovasinin and its related metabolites, neovasipyrones A and B and neovasifuranones A and B, in the phytopathogenic fungus Neocosmospora vasinfecta"J.Chem.Soc., Perkin Trans.1. 1999. 131-135 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] P.Singh: "Purification and biological characterization of host-specific SV-toxins from Stemphylium vesicarium causing brown spot of European pear"Phytopathology. 89. 947-953 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Fujii: "Zygosporin D and two new cytochalasins produced by the fungus Metarrhizium anisopliae"Journal of Natural Products. 63. 132-135 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] P.Singh: "Effects of host-selective SV-toxin from Stemphylium vesicarium, the cause of brown spot of European pear plants on ultrastructure of leaf cells"J.Phytopathology. 148. 87-93 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] E.Sakuno: "A new inhibitor of 5'-hydroxyaverantin dehydrogenase, an enzyme involved in aflatoxin biosynthesis, from Trichoderma hamatum"Journal of Natural Products. 63. 1677-1678 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Fujii,H.Tani,M.Ichinoe and H.Nakajima: "Zygosporin D and Two new cytochalasins produced by the fungus Metarrhizium anisopliae"Journal of Natural Products. 63. 132-135 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] P.Singh,P.Park,R.Bugiani,P.Cavanni,H.Nakajima et.al.: "Effects of host-selective SV-toxin from Stemphylium vesicarium, the cause of brown spot of European pear plants, on ultrastructure of leaf cells"J. Phytopathology. 148. 87-93 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] E.Sakuno,K.Yabe,T.Hamasaki and H.Nakajjima: "A new inhibitor of 5'-hydroxyaverantin dehydrogenase, an enzyme involved in aflatoxin biosynthesis, from Trichoderma hamatum"Journal of Natural Products. 63. 1677-1678 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] H.Tani,Y.Fujii and H.Nakajjima: "Chlamydocin analogues from the soil fungus Peniophora sp.: structures and plant growth-retardant activity"Pytochemistry. (発表予定). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Furumoto,T.Hamasaki and H.Nakajima: "Biosynthesis of phytotoxin neovasinin and its related metabolites,neovasipyrones A and B and neovasifuranones A and B,in the phytopathogenic fungus Neocosmospora vasinfecta"J.Chem.Soc.,Perkin Trans.1. 1999. 131-135 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] P.Singh,R.Bugiani,P.Cavanni,H.Nakajima,M.Kodama,H.Otani and K.Kohmoto: "Purification and biological characterization of host-specific SV-toxins from Stemphylium vesicarium causing brown spot of European pear"Phytopathology. 89. 947-953 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Y.Fujii,H.Tani,M.Ichinoe and H.Nakajima: "Zygosporin D and two new cytochalasins produced by the fungus Metarrhizium anisopliae"Journal of Natural Products. 63. 132-135 (2000)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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