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2004 Fiscal Year Final Research Report Summary

Preparation of insect juvenile hormone (JH) antagonists and identification of JH receptors

Research Project

Project/Area Number 14360031
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 植物保護
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

KUWANO Eiichi  Kyushu University, Department of Applied Genetics and Pest Management, Professor, 大学院・農学研究院, 教授 (00108672)

Project Period (FY) 2002 – 2004
Keywordsanti-juvenile hormone / precocious metamorphosis / juvenile hormone esterase
Research Abstract

Ethyl 4-[2-(tert-butylcarbonyloxy)butyloxy]benzoate (ETB), an anti juvenile hormone (anti-JH) agent, has been reported to act as a partial JH antagonist at the target tissue of the larval epidermis. By modifying the structure of ETB, we have found that ethyl [2-(6-methyl-3-pyridyloxy)butyloxy]-benzoate (EMP) induced precocious metamorphosis in larvae of Bombyx mori, which is clearly recognized as a JH-deficiency symptom. In contrast to ETB, EMP induced precocious metamorphosis in a dose-dependent manner. The structure-activity relationship studies indicated that the 4-ethoxycarbonyl group on the benzene ring and the 6-methyl-3-pyridyl moiety were apparently essential for activity. The activity of EMP could be fully counteracted by methoprene, a JH agonist, but not by the dietary administration of 20-hydroxyecdysone, indicating that EMP causes a deficiency of JH titers in the larval hemolymph. In order to identify a target molecule of EMP, which might be related to a JH receptor, an EMP … More derivative coupled to horseradish peroxidase was prepared as an affinity ligand. However, high-affinity binding site for EMP was not found in the ovary follicular cell of the pupae and larval head capsules. To develop more potent anti-JH agent, the ethyl side chain of EMP was modified. Of the compounds tested, ethyl 4-[4-methyl-2-(6-methyl-3-pyridyloxy)pentyl-oxy]benzoate (1) was the most effective when applied to 24hr-old 3rd instar larvae. There was no significant different in precocious metamorphosis-inducing activity between 1R(+)- and 1S(-)-enantiomers. Since the benzoic acid analogs did not show any activity by both topical application and dietary administration, the ethoxycarbonyl group itself was responsible for activity. When 3rd instar larvae were treated with compound 1, hemolymph JH esterase, which is indispensable for the initiation of pupation in the last instar larvae, was induced during the 4th instar larvae. Compound 1 represents a structurally novel class of anti-JH agent. Less

  • Research Products

    (8 results)

All 2004 2003

All Journal Article (8 results)

  • [Journal Article] Detection of proteins with a high affinity for imidazole insect Growth regulator, KK-422004

    • Author(s)
      T.Shiotsuki et al.
    • Journal Title

      Journal of Pesticide Science 29

      Pages: 121-123

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Detection of proteins with a high affinity for imidazole insect growth regulator, KK-42.2004

    • Author(s)
      T.Shiotsuki, E.Kuwano
    • Journal Title

      J.Pestic.Sci. 29

      Pages: 121-123

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis and structure-activity relationships of 6-methyl-3-pyridyl ethers as anti-juvenile hormone agents2003

    • Author(s)
      In-Hae Kim et al.
    • Journal Title

      Journal of the Faculty of Agriculture, Kyushu University 47

      Pages: 395-405

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Ethyl 4-[2-(6-methyl-3-pyridyloxy)butyloxy]benzoate, a novel anti-juvenile hormone agent2003

    • Author(s)
      H.Ishiguro et al.
    • Journal Title

      Bioscience Biotechnology and Biochemistry 67

      Pages: 2045-2047

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 1,5-Disubstituted imidazoles inhibit juvenile hormone biosynthesis by the corpora allata of the mosquito Aedes aegypti2003

    • Author(s)
      Yieping Li et al.
    • Journal Title

      Journal of Insect Physiology 49

      Pages: 1005-1011

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis and structure-activity relationships of 6-methyl-3-pyridyl ethers as anti-juvenile hormone agents.2003

    • Author(s)
      I.-H.Kim, E.Kuwano
    • Journal Title

      J.Fac.Agr.Kyushu Univ. 47

      Pages: 395-405

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Ethyl 4-[2-(6-methyl-3-pyridyloxy)butyloxy]benzoate, a novel anti-juvenile hormone agent.2003

    • Author(s)
      H.Ishiguro, N.Fujita, I.-H.Kim, T.Shiotsuki, E.Kuwano
    • Journal Title

      Biosci.Biotechnol.Biochem. 67

      Pages: 2045-2047

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] 1,5-Disubstituted imidazoles inhibit juvenile hormone biosynthesis by the corpora allata of the mosquito Aedes aegypti.2003

    • Author(s)
      Y.Li, E.Kuwano, F.G.Noriega
    • Journal Title

      J.Insect Physiol. 49

      Pages: 1005-1011

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2006-07-11  

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