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Bioorganic Chemical Studies for Biorational Pest Control

Research Project

Project/Area Number 59430021
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

MIZUTANI Junya  Faculty of Agriculture, Hokkaido University Prof., 農学部, 教授 (50014923)

Co-Investigator(Kenkyū-buntansha) TAHARA Satoshi  Faculty of Agriculture, Hokkaido University Associate Prof., 農学部, 助教授 (50001475)
KASAI Takanori  Faculty of Agriculture, Hokkaido University Associate Prof., 農学部, 助教授 (80001444)
SAKAMURA Sadao  Faculty of Agriculture, Hokkaido University Prof., 農学部, 教授 (10001372)
Project Period (FY) 1984 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥32,900,000 (Direct Cost: ¥32,900,000)
Fiscal Year 1986: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1985: ¥6,400,000 (Direct Cost: ¥6,400,000)
Fiscal Year 1984: ¥25,500,000 (Direct Cost: ¥25,500,000)
KeywordsBiorational Pest Control / Plant Growth Inhibitors / Fungitoxic Substances / Cyclopentanoid Sesquiterpenes / <gamma> -Glutamyl Peptides / Canavanine / Isoflavones / ファイトアレキシン / 植物病原菌 / γ-Glu誘導体 / 自己防衛的能力
Research Abstract

1. Hirsutin ( <1!wave> ), a mustard oil of Rorippa sylvestris (Cruciferae) exhibited the plant growth inhibitory activity. We investigated the structure-activity relationships of <1!wave> and related compounds (29 compounds in all), and it has been shown that <1!wave> may be a lead compound for the development of herbicides. Lichenic acids (3 phenolic acids and 6 depsides) isolated from Usnea spp. (Lecanorales) showed the plant growth inhibitory activity.
2. New fungitoxic cyclopentanoid sesquiterpenes (6 compounds), new oxidized C-18 unsaturated fatty acids (6 compounds), oxidized C-9 <to> C-11 fatty acids and hydroxydi-hydrobovolide have been isolated from timothy choke caused by Epichloe typhina. Antifungal, and plant seed germination and growth inhibitory activities of these compounds were tested. The timothy plant infected by E. typhina has been found to be resistant against another timothy leaf spot disease pathogen, Cladosporium phlei, and the resistant mechanism was discussed in … More connection with these antifungal compounds. The above-mentioned compounds were also suggested to cause the inhibition of coming into ears of the infected timothy plants.
3. Eight <gamma> -glutamyl peptides were isolated from the bulbs of Allium bakeri (Liliaceae). The canavanine content of alfalfa seeds rather increased during germination contrary to the knowledge from literature. The insecticidal and antimicrobial activities of <gamma> -glutamyl peptides, canavanine and related compounds were tested, but no compounds were found to show remarkable activities.
4. New complex isoflavones (6 compounds), coumaronochromones (6 compounds) and 5-o-methylisoflavones (5 compounds) were isolated from yellow and white lupins. Five pterocarpans including one new compound and new four 3-hydroxyflavanones as phytoalexins were found in two species (Leguminosae), respectively. Furthermore, metabolic pathways of fungitoxic prenylated isoflavones by fungi were studied, and it was suggested that the chemical defense mechanism against pathogens in the lupins might be broken down through the detoxification of antifungal compounds by fungi. Less

Report

(2 results)
  • 1986 Final Research Report Summary
  • 1985 Annual Research Report
  • Research Products

    (33 results)

All Other

All Publications (33 results)

  • [Publications] YOSHIHARA,Teruhiko: Tetrahedron Letters. 26. 5551-5554 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] TAHARA,Satoshi: Agric.Biol.Chem.49. 1775-1783 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] TAHARA,Satoshi: Agric.Biol.Chem.49. 2605-2612 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] INGHAM,John L.: Z.Naturforsch.40C. 482-489 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] 田原哲士: 日本農芸化学会誌. 59. 1039-1044 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] KASAI,Takanori.: J.Nutr.Sci.Vitaminol.32. 77-82 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] INGHAM,John L.: Z.Naturforsch.41C. 403-408 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] NAKAHARA,Shiro: Agric.Biol.Chem.50. 863-873 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] HASHIDOKO,Yasuyuki: Agric.Biol.Chem.50. 1797-1807 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] TAHARA,Satoshi: Agric.Biol.Chem.50. 1809-1819 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] INGHAM,John L.: J.Nat.Prod.49. 631-638 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] KOSHINO,Hiroyuki: Tetrahedron Letters. 28. 73-76 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] SUZUKI,Ken: Agric.Biol.Chem.51. 1003-1008 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] NISHITOBA,Yukiko: Phytochemistry.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] YOSHIHARA, Teruhiko: "Three Fungitoxic Cyclopentanoid Sesquiterpenes from Stromata of Epichloe typhina." Tetrahedron Letters. 26. 5551-5554 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] TAHARA, Satoshi: "New Coumaronochromones from White Lupin Lupinus albus L. (Leguminosae)." Agric. Biol. Chem.49. 1775-1783 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] TAHARA, Satoshi: "Fungal Metabolism of the Prenylated Isoflavone Licoisoflavone A." Agric. Biol. Chem.49. 2605-2612 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] TAHARA, Satoshi: "Fungal Metabolites of Antifungal Isoflavone Wighteone." Nippon Nogeikagaku Kaishi. 59. 1039-1044 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] INGHAM, John L.: "Isoneorautenol and Other Pterocarpan Phytoalexins from Calopogonium mucunoides." Z. Naturforsch.40c. 482-489 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] KASAI, Takanori: "Reexamination of Canavanine Disappearance during Germination of Alfalfa (Medicago sativa)." J. Nutr. Sci. Vitaminol.32. 77-82 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] INGHAM, John L.: "A Chemical Investigation of Pueraria mirifica Roots." Z. Naturforsch.41c. 403-408 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] NAKAHARA, Shiro: "Transformation of the Diprenylated Isoflavone 2'-Hydroxylupalbigenin by Aspergillus flavus." Agric. Biol. Chem.50. 863-873 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] HASHIDOKO, Yasuyuki: "New Complex Isoflavones in the Roots of Yellow Lupin (Lupinus luteus L. cv. Barpine)." Agric. Biol. Chem.50. 1797-1807 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] TAHARA, Satoshi: "New 5-o-Methylisoflavones in the Roots of Yellow Lupin (Lupinus luteus L. cv. Barpine)." Agric. Biol. Chem.50. 1809-1819 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] INGHAM, John L.: "New 3-Hydroxyflavanone (Dihydroflavonol) Phytoalexins from the Papilionate Legume Shuteria vestita." J. Nat. Prod.49. 631-638 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] KOSHINO, Hiroyuki: "Four Fungitoxic C-18 Hydroxy Unsaturated Fatty Acids from Stromata of Epichloe typhina." Tetrahedron Letters. 28. 73-76 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] SUZUKI, Ken: "New 3,5,4'-Trihydroxystilbene (Resveratrol) Oligomers from Carex fedia Nees var. miyabei (Franchet) T. Koyama (Cyperaceae)." Agric. Biol. Chem.51. 1003-1008 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] NISHITOBA, Yukiko: "Lichenic Acids, Plant Growth Inhibitors in Usnea longissimae." Phytochemistry.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Tetrahedron Letters. 26-45. (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] J.Nutr.Sci.Vitaminol.37-1. (1986)

    • Related Report
      1985 Annual Research Report
  • [Publications] Agric.Biol.Chem.49-6. (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] Agric.Biol.Chem.49-9. (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] 日本農芸化学会誌. 59-10. (1985)

    • Related Report
      1985 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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