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Chemical Studies on Growth Self-inhibitors Produced by Phytopathogenic Fungi.

Research Project

Project/Area Number 60470134
Research Category

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

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

Principal Investigator

SASSA Takeshi  Professor, Faculty of Agriculture, Yamagata University, 農学部, 教授 (80023456)

Project Period (FY) 1985 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥4,200,000 (Direct Cost: ¥4,200,000)
Fiscal Year 1987: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1986: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1985: ¥2,600,000 (Direct Cost: ¥2,600,000)
KeywordsPhytopathogenic fungi / Rowth self-inhibitor / Chloromonilicin / Bromomonilicin / 4-chloropinselin / Moniliphenone / Chloromonilinic acids / ウスニン酸イソメトキシド / オウトウ炭疽病菌 / オウトウ灰星病菌 / クロロモニリシンの生合成 / モニリフェノン
Research Abstract

1. Chloromonilicin, a growth self-inhibitor produced by cherry brown fungus Momilinia fructicola.
(1) A new growth self-inhibitor, chloromonilicin (I), was isolated from M. fructicola, and its structure having a novel seven-membered lactone ring was determined on the basis of chemical and spectroscopic evidence. 4-Chloropinselin (II), a probable precursor of I, was also isolated and identified. I showed strong antifungal activity against phytopathogenic fungi.
(2) The bromine congener, bromomonilicin, was prepared by fermentation. In addition, moniliphenone (III), a new benzophenone metabolite, was isolated from the bromomonilicinfe- fermentation broth. The biosynthetic pathway, III-> II-> I, was revealed by feeding experiments using deuterated III.
(3) Novel lactone-reduced catabolites of I, which were named chloromonilinic acids A and B, were isolated from the chloromonilicin-fermrntation broth. They hardly showed antimicrobial activity. Bromomonilicin was transformed into bromomonilinic acid B, and then the latter into bromomonilinic acid A by M. fructicola.
2. Growth self-inhibiting substances produced by other phytopathogenic fungi.
(1) Two structurally related growth self-inhibitors were isolated form circular leaf spot fungus Mycosphaerella nawae. One of them was identified as (-)-usnic acid isomethoxide.
(2) A growth self-inhibiting substance was obtained from cherry anthracnose fungus Glomerella cingulata. The active substance was unstable, and gave an inactive compound by methanolysis.

Report

(2 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] Takeshi, Sassa: J. Antibiot.38. 439-441 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hideaki, Kachi: J. Antibiot. 39. 164-166 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hideaki, Kachi: Agric. Biol. Chem.50. 1669-1671 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 佐々武史: 第28回天然有機化合物討論会講演要旨集. 17-24 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Takeshi Sassa: Agric. Biol. Chem.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Takeshi,Sassa: "Chloromonilicin, a New Antifungal Metabolite Produced by Monilinia fructicola." J. Antibiot.38. 439-441 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hideaki,Kachi: "A New Antifungal Substance, Bromomonilicin, and Its Precursor Produced by Monilinia fructicola." J. Antibiot.39. 164-166 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hideaki,Kachi: "Isolation of Moniliphenone, a Key Intermediate in Xanthone Biosyuthesis form Monilinia fructicola." Agric. Biol. Chem.50. 1669-1671 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Takeshi,Sassa: "chloromonilicin as a Growth Self-inhibitor and Its Biosynthetic Intermediates produced by Monilinia fructicola." Abstracts of Papers, 28th Symposium on the chemistry of naturay of Natural Products Abstracts of Papers, 28th Symposium on the chemistry of naturay of Natural Products (Sendai, October). 17-24 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Takeshi,Sassa: "Chloromonilinic Acids A and B, Novel lactone-reduced Catabolites of a Growth Self-inhibitor Chloromonilicin Produced by Monilinia fructicola." Agric. Biol. Chem., submitted for publication.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Kachi,Hideaki: Agric.Biol.Chem.50. 1669-1671 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] 佐々武史: 第28回天然有機化合物討論会講演要旨集. 17-24 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] 佐々武史: 日本農芸化学会誌. 60. 991- (1986)

    • Related Report
      1986 Annual Research Report

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

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