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Identification of Conjugated Pentadecadienals as Sex Pheromone Components of the Sphingid Moth, Dolbina tancrei

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An Erratum to this article was published on 01 August 2014

Abstract

Homologs of bombykal, (10E,12Z)-10,12-hexadecadienal, have been reported to be sex pheromones or sexual attractants of several species of sphingid moths. In this study, we identified novel bombykal analogs as sex pheromone components from a Japanese sphingid moth, Dolbina tancrei. Staudinger (Sphingidae: Lepidoptera). Sex pheromone gland extracts from calling female moths were subjected to gas chromatography/electroantennograhic detection (GC/EAD), gas chromatography/mass spectrometry (GC/MS), and gas chromatography (GC) analyses. GC/EAD analyses showed two active components in the crude pheromone extracts. GC/MS analysis determined these two components to be pentadecadienals. GC/MS of their MTAD derivatives showed conjugated double bonds at the 9- and 11-positions, indicating 9,11-pentadecadienals. The isomeric configurations of these candidates were determined by comparison of their Kováts retention indices with those of synthetic compounds. Field bioassays with the four isomers of 9,11-pentadecadienal and their mixtures confirmed that the two sex pheromone components of D. tancrei are (9E,11Z)-9,11-pentadecadienal and (9Z,11Z)-9,11-pentadecadienal, with the highest male catches observed for a 90:10 blend. This is the first report of 9,11-pentadecadienals as sex pheromone components in lepidopteran species.

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Acknowledgments

We thank Dr. DeMar Taylor for his critical reading of the manuscript and Mr. Takahiro Yano for important information on D. tancrei. We are also grateful to Ms. Kanako Ohbayashi and students of the Laboratory of Applied Entomology in Tottori University for their help with insect collection and rearing.

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Authors and Affiliations

  1. Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki, 305-8572, Japan

    Takuya Uehara

  2. Faculty of Agriculture, Tottori University, Tottori, Koyama Minami, 680-8553, Japan

    Hideshi Naka

  3. Faculty of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki, 305-8572, Japan

    Shigeru Matsuyama & Hiroshi Honda

  4. Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Koganei, 184-8588, Japan

    Le van Vang & Tetsu Ando

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  1. Takuya Uehara
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  2. Hideshi Naka
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  3. Shigeru Matsuyama
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  4. Le van Vang
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  5. Tetsu Ando
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  6. Hiroshi Honda
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Correspondence to Hiroshi Honda.

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Uehara, T., Naka, H., Matsuyama, S. et al. Identification of Conjugated Pentadecadienals as Sex Pheromone Components of the Sphingid Moth, Dolbina tancrei . J Chem Ecol 39, 1441–1447 (2013). https://doi.org/10.1007/s10886-013-0357-1

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  • DOI: https://doi.org/10.1007/s10886-013-0357-1

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