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1993 Fiscal Year Final Research Report Summary

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
KeywordsPhytotoxins / Plant Pathogenic fungi / Defensive substaces / ストレス化合物
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.

  • Research Products

    (20 results)

All Other

All Publications (20 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1995-03-27  

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