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Dynamic Molecular aspects on Plant Disease and Defense Mechanism

Research Project

Project/Area Number 03403021
Research Category

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

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionHokkaido University

Principal Investigator

ICHIHARA Akitami  Hokkaido University, Fac.of Agric.Dept.of Biosci. and Chem. Professor, 農学部, 教授 (20000820)

Co-Investigator(Kenkyū-buntansha) SATO Hiroji  Hokkaido University, Fac.of Agric.Experiment Farm, Associate Professor, 農学部・附属農場, 助教授 (20002074)
TAHARA Satoshi  Hokkaido University, Fac.of AGric.Dept.of Biosci. and Chem. Associate Professor, 農学部, 助教授 (50001475)
YOSHIHARA Teruhiko  Hokkaido University, Fac.of Agric.Dept.of Biosci. and Chem. Associate Professor, 農学部, 助教授 (90002071)
Project Period (FY) 1991 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥34,700,000 (Direct Cost: ¥34,700,000)
Fiscal Year 1993: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1992: ¥8,100,000 (Direct Cost: ¥8,100,000)
Fiscal Year 1991: ¥23,100,000 (Direct Cost: ¥23,100,000)
KeywordsPhytotoxins / Plant Pathogenic fungi / Defensive substaces / ストレス化合物 / 植物毒素 / 生理活性物質 / アルタナル酸 / 防御物質 / 交叉防除
Research Abstract

This project was undertaken to investigate in molecular level on the phytotoxins involved in the invasion of plants by pathogens and defense substance (stress compounds) involved in the resistance of plants to the invading microorganisms. Summary of research results are as follows.
1. Stereochemistry of alternaric acid, a phytotoxic metabolite of Alternaric solani, have been elucidated, and total synthesis of the phytotoxin has been completed. Several phytoxines related to alternaric acid have been isolated from culture filtrate of the fungus.
2. The structures of phytotoxic compounds from Valsa ambiens have been determined.
3. Many stress compounds were isolated from Leguminosae and their bioorganic chemistry has been studied.
4. The structures of the metabolites of Ceratocystis piceae were revealed to be (3R, 5R)-(+)-3-hydroxytetradecan-5-olide and its derivatives. The structure of abscisterol isolated from Cryptosporiopsis abietina has been determined as 21-nor-24-methylene-5alpha-cholesta-7,17(20)-E-diene-4beta ; 19-epoxy-3beta-01 from NMR spectra and CD experiments.
5. Degradation of AAL-toxin, a host-specific toxin and synthesis of model aminotriols allowed us to determine the absolute configuration as 2S, 4S and 5R.

Report

(4 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • 1991 Annual Research Report
  • Research Products

    (35 results)

All Other

All Publications (35 results)

  • [Publications] H.Tabuchi: "Total Synthyesis of Alternaric Acid" Tetrahedron Letters. 34. 2327-2330 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tabuchi: "Structures and Stereochemistries of New Compounds Related to Alternaric Acid" J.Chem.Soc.,Perkin Trans.I. 125-133 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Y.Jiao: "Two Phenolic Compounds from Valsa ambiens" Biosci.Biotech.Biochem.58. 784-785 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Y.Hashidoko: "Six Sesquiterpenoids from Glandular Trichome Exudates of Rosa rugosa" Phytochemistry. 35. 325-329 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Yada: "New Aliphatic δ-Lactones,Metabolites of Ceratocystis piceae" Natural Products Letters. 2. 221-226 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tabuchi, A.Tajimi, A.Ichihara: "Novel Acetamides Isolated from Scolecotrichum graminis Fuckel" Agric.Biol.Chem.55. 2669-2671 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tabuchi, A.Tajimi, A.Ichihara: "(+)-Isocercosporin, A Phytotoxic Compunds Isolated from Scolecotrichum graminis Fuckel" Agric.Biol.Chem.55. 2675-2676 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] R.Sakai, Y.Mino, T.Sakaki, A.Ichihara, S.Sakamura: "Phytotoxicity of Fulvic Acid Produced by Cercospora beticola, of Fulvic Acid Produced by Cercospora beticola" Ann.Phytopath.Soc.Japan. 58. 95-98 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tabuchi, A.Ichihara: "Stereochemistry of Alternaric Acid : Synthesis of the C(9)-C(14) Fragment" Tetrahedron Lett.33. 4933-4936 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Yoshihara, T.Sakamura, A.Ichihara: "Yellow Fluorescent Stress Compounds, Pratenols A and B, from Red Clover (Trifolium pratense) Infected by Kabatiella caulivora" Biosci.Biotech.Biochem.56. 1955-1958 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Koshino, T.Yoshihara, A.Ichihara, A.Tajimi, T.Shimanuki: "Two Sphingoid Derivatives from Stromata of Epichloe Typhina on Phleum Pratense" Phytochemistry. 31. 3757-3759 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tabuchi, T.Hamamoto, S.Miki, T.Tejima, A.Ichihara: "Total Synthesis of Alternaric Acid" Tetrahedron Lett.34. 2327-2330 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] S.Tahara, F.Saitoh, J.Mizutani: "7-0-Methyl-luteone Metabolism in Botrytis cinerea : Identification of the Epoxy-intermediate and Absolute Configuration of the Pyrano-isoflavone Metabolite" Z.Naturforsch.48C. 16-21 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] S.Tahara, M.Moriyama, J.L.Ingham, J.Mizutani: "Atropisomers from Piscidia erythrina" Phytochemistry. 34. 545-552 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Yada, H.Sato, S.Kaneko, A.Ichihara: "New Aliphatic delta-Lactones, Metabolites of Ceratocystis piceae" Natural Product Lett.2. 221-226 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tabuchi, T.Hamamoto, A.Ichihara: "Modification of Fries Type Rearrangement of 0-Enol Acyl Group Using N,N-Dicyclohexylcarbodiimide and 4-Dimethyllaminopyridine" Synlett.651-652 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tabuchi, A.Ichihara: "Structures and Streochemistries of New Compounds Related to Alternaric Acid" J.Chem.Soc., Perkin Trans.1. 125-133 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Y.Jiao, T.Yoshihara, M.Akimoto, A.Ichihara, Y.Koda: "Two Phenolic Compounds from Valsa Ambiens" Biosci.Biotech.Biochem.58. 784-785 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.Nakamori, H.Matsuura, T.Yoshihara, A.Ichihara, Y.Koda: "Potato micro-tuber Inducing Substances from Lasiodiplodia Theobramae" Phytochemistry. 32, (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Oikawa, I.Matsuda, A.Ichihara, K.Kohmoto: "Absolute Configuration of C(1)-C(5) Fragment of AAL-toxin" Tetrahedron Lett.35, (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tabuchi: "Stereochemistry of Alternaric Acid" Tetrahedron Letters. 33. 4933-4936 (1992)

    • Related Report
      1993 Annual Research Report
  • [Publications] H.Tabuchi: "Total Synthyesis of Alternaric Acid" Tetrahedron Letters. 34. 2327-2330 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] H.Tabuchi: "Structures and Stereochemistries of New Compounds Related to Alternaric Acid" J.Chem.Soc.,Perkin Trans.I. 125-133 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.Jiao: "Two Phenolic Compounds from Valsa ambiens" Biosci.Biotech.Biochem.58. 784-785 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.Hashidoko: "Six Sesquiterpenoids from Glandular Trichome Exudates of Rosa rugosa" Phytochemistry. 35. 325-329 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] H.Yada: "New Aliphatic δ-Lactones,Metabolites of Ceratocystis piceae" Natural Products Letters. 2. 221-226 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] R.Sakai: "Phytotoxicity of Fulvic Acid Produced by Cercospora beticola" Ann Phytopath. Soc Japan. 58. 95-98 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.Tabuchi: "Strereochemistry of Alteranaric Acid ; Symthesis of the C(9)-C(14) Fragment" Tetrahedrom Lett.33. 4933-4936 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.MAtsuura: "A Novel Sesquiterpene, Tuberonone, from Solanum Tuberosum L" Biosci. Biotech. Biochem. 56. 1890-1891 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Yodhihara: "Yrllow Fluorescent Stress Compounds. Pratenols A and B from Red Clover(Trifolium Pratense) Inrected by Kabatiella caulivora" Biosci. Biotech. Biochem. 56. 1955-1958 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.Gagnon: "Biosynthesis of White Lupin Lsoflavonoids from [U-^<14>C]L-Phenylalanine and their release into the Culture Medium" Plant Physiol.100. 76-79 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Hiroyasu Tabuchi: "Novel Acetamides Isolated from Scolecotrichum graminis Fuckel" Agric.Biol.Chem.55. 2669-2671 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Hiroyasu Tabuchi: "(+)ーIsocercosporin,A Phytotoxic Compound Isolated from Scolecotrichum graminis Fuckel" Agric.Biol.Chem.55. 2675-2676 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Hideaki Oikawa: "New Plausible Precursors of Chaetoglobosin A Accumulated by Treatment of Chaetomium subaffine with Cytochrome Pー450 Inhibitors" Tetrahedron Lett.35. 4533-4536 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Fujinori Hanawa: "Isoflavonoids Produced by Iris pseudocorus Leaves Treated with Cupric Chloride" Phytochemistry. 30. 157-163 (1991)

    • Related Report
      1991 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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