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2001 Fiscal Year Final Research Report Summary

Study on mechanisms for production and reception of epoxy sex pheromones produced by Geometrid moths

Research Project

Project/Area Number 10660315
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Applied molecular and cellular biology
Research InstitutionTokyo University of Agriculture and Technology

Principal Investigator

ANDO Tetsu  Tokyo University of Agriculture and Tecnology Gradnate School of BASE, Prof., 大学院・生物システム応用科学研究科, 教授 (50151204)

Project Period (FY) 1998 – 2001
Keywordspheromone / Sex pheromone / Lepidoptera / biosynthesis / offactory perception / epoxidation / neuropeptide / pheromore binding protein
Research Abstract

Female moths in the family of Geometridae produce cis-epoxides of poly-unsaturated hydrocarbons with a straight chain. In vivo experiments using deuterium-labeled compound revealed substrate specificity of enzymes for a step of mono-epoxidation in the pheromone biosynthesis. Analysis of hemolymph of the virgin females showed occurrence of the hydrocarbons, indicating that the precursors of the epoxy pheromones were produced.outside of the pheromone gland and transported to the gland via hemolymph for perfection of the biosynthesis. This production system is different from that proposed for the silkworm moth. Furthermore, experiments with incubated pheromone glands showed that the pheromone production was regulated by a hormone (pheromone biosynthesis activating neuropeptide, PBAN) secreted from a subesophageal ganglion. The neuropeptide did not stimulate the epoxidation enzyme, but activate transport of the hydrocarbons into the glands.
The antennae of male moths include pheromone-binding protein (PBP). The amino acid sequence of a gerometrid PBP showed positional conservation of six cysteine residues and high homology (about 80 %) with the PBP of the silkworm moth. In order to understand the mechanism of olfactory perception, its binding specificity and function is studying.
Epoxy pheromones have been also identified from females in other families ; I.e. Noctuidae, Arctiidae, and Lymantriidae. These families include a large number of species, and it is expected that some females produced further modified compounds. From two lymantriid species in, we successfully identified novel pheromone components with two epoxy rings or a trans-epoxy ring, which offered new interesting subjects for research of the epoxy sex pheromones.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Takashi MIYAMOTO et al.: "Substrate specificity of the epoxidation reaction in sex pheromone biosynthesis of the Japanese giant looper (Lepidoptera : Geometridae)"Insect Biochem. Mol. Biol.. 29. 63-69 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Masanobu YAMAMOTO et al.: "A convenient preparation of optically active diepoxyhenicosene (leucomalure), lymantrid sex pheromone, by chiral HPLC"Eur. J. Org. Chem.. 7. 1503-1506 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Masanobu YAMAMOTO et al.: "Identification of chiral sex pheromone secreted by giant geometrid moth, Biston robustum Butler"J. Chem. Ecol.. 26. 2579-2590 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sadao WAKAMURA et al.: "Posticlure : a novel trans-epoxide as a sex pheromone component of the tussock moth, Orgyia postica (Walker)"Tetrahedron Lett.. 42. 687-689 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki YAMAZAWA et al.: "Synthesis and characterization of diepoxyalkenes derived from (3Z,6Z,9Z)-trienes, lymantriid sex pheromones and their candidates"J. Chem. Ecol.. 27. 2153-2167 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sadao WAKAMURA et al.: "Identification of epoxyhenicosadiene and novel diepoxy derivatives as sex pheromone components of the clear-winged tussock moth Perina nuda"J. Chem. Ecol.. 28. 431-449 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takashi MIYAMOTO, Masanobu YAMAMOTO, Akihiko ONO, Kazuya OHTANI, Tetsu ANDO: "Substrate Specificity of the Epoxidation Reaction in Sex Pheromone Biosynthesis of the Japanese Giant Looper (Lepidoptera : Geometridae)"Insect Biochem. Mol Biol.. 29(1). 63-69 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Masanobu YAMAMOTO, Hiroyuki YAMAZAWA, Naoto NAKAJIMA, Tetsu ANDO: "A Convenient Preparation of Optically Active Diepoxyhen icosene (Leucomalure), Lymantrid Sex Pheromone, by Chiral HPLC"Euro. J. Org. Chem.. 1503-1506 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Masanobu YAMAMOTO, Masaaki KISO, Hiroyuki YAMAZAWA, Jun TAKEUCHI, Tetsu ANDO: "Identification of Chiral Sex Pheromone Secreted by Giant Geometrid Moth, Biston robustum Butler"J. Chem. Ecol.. 26(11). 2579-2590 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sadao WAKAMURA, Norio ARAKAKI, Masanobu YAMAMOTO, Syuntaro HIRADATE, Hiroe YASUI, Tetsuya YASUDA, Tetsu ANDO: "Posticlure : a Novel trans-Epoxide as a sex Pheromone Component of the Tussock Moth, Orgyia postica (Walker)"Tetrahedron Lett.. 42(4). 687-689 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki YAMAZAWA, Naoto NAKAJIMA, Sadao WAKAMURA, Norio ARAKAKI, Masanobu YAMAMOTO, Tetsu ANDO: "Synthesis and Characterization of Diepoxyalkenes Derived from (3Z,6Z,92)-Trienes, Lymantriid Sex Pheromones and Their Candidates"J. Chem. Ecol.. 27(11). 2153-2167 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sadao WAKAMURA, Norio ARAKAKI, Hiroyuki YAMAZAWA, Naoto NAKAJIMA, Masanobu YAMAMOTO, Tetsu ANDO: "Identification of Epoxyheriicoxadiene and Novel Diepoxy Derivatives as Sex Pheromone Components of the Clear-Winged Tussock Moth Perina nuda"J. Chem. Ecol.. 28(3). 431-449 (2002)

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

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Published: 2003-09-17  

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