Cyclopropene Fatty Acid and Amide

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  • ANDO Tetsu
    Department of Applied Biological Science, Faculty of Agriculture, Tokyo University of Agriculture and Technology
  • OHNO Ryuta
    Department of Applied Biological Science, Faculty of Agriculture, Tokyo University of Agriculture and Technology
  • IKEMOTO Kazuhisa
    Department of Applied Biological Science, Faculty of Agriculture, Tokyo University of Agriculture and Technology
  • YAJIMA Yohko
    Department of Applied Biological Science, Faculty of Agriculture, Tokyo University of Agriculture and Technology

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Other Title
  • シクロプロペン構造を有する脂肪酸とそのアミド体
  • シクロプロペン構造を有する脂肪酸とそのアミド体--カイコガ性フェロモン生合成の阻害剤〔英文〕
  • シクロプロペン コウゾウ オ ユウスル シボウサン ト ソノ アミドタイ カイ
  • Inhibitors of the Pheromone Biosynthesis in <i>Bombyx mori</i>

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11, 12-Methylenehexadec-11-enoic acid and the amide were synthesized by the method of Baird et al. (1992) via a key intermediate, 1, 2, 2-tribromo-1-butylcyclopropane, which was debrominated and coupled with an alkylhalide resulting in a dialkylcyclopropene. Their activities as inhibitors of pheromone biosynthesis were examined with virgin females of the silkworm moth, Bombyx mori, in vivo. Bombykol titer diminished in the pheromone glands treated with the cyclopropenes, and experiments utilizing [1-14C] or [16, 16, 16-2H3]-hexadecanoic acids as a biosynthetic precursor showed that the cyclopropenes completely inhibited incorporation of the isotopes into bombykol and (Z)-11-hexadecen-1-ol at the dose of 1μg per pheromone gland but accelerated incorporation into hexadecan-1-ol. These results revealed the acid and amide with a propene ring at the 11-position are inhibitors of desaturation step(s), Δ11-desaturation and possibly Δ10, 12-desaturation, in the biosynthetic pathway. The nitrite derivative with the propene ring did not inhibit the bombykol biosynthesis.

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