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Contact Sex Pheromone Components of the Seed Beetle, Callosobruchus analis (F.)

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Abstract

Callosobruchus analis (Coleoptera: Chrysomelidae: Bruchinae), found throughout tropical Asia and Africa, is a pest of stored legumes. Previous work has shown that females of this species produce a contact sex pheromone that elicits copulatory behavior in males. Comparisons of copulatory activity between any two of four congeneric species suggest that the contact sex pheromones are species specific. In laboratory bioassays, male C. analis exhibited copulatory behavior to a female dummy to which a crude extract of virgin females was applied. The extract had been collected by a filter paper method and was purified by acid–base partition and chromatographic techniques. Gas chromatography-mass spectrometry (GC-MS) analyses of active fractions revealed that the active compounds were 2,6-dimethyloctane-1,8-dioic acid (1) and callosobruchusic acid, (E)-3,7-dimethyl-2-octene-1,8-dioic acid (2), previously identified as contact sex pheromones of Callosobruchus maculatus (F.) and C. chinensis (L.), respectively. The stereoisomeric and chemical compositions were determined by the 2D-HPLC-Ohrui-Akasaka method as (2S,6R)-1:(S)-2 = 1.8:1, which meant that both compounds in C. analis were stereochemically pure, unlike the case of C. maculatus and C. chinensis. An examination of the influence of synthetic pheromone compounds on male copulatory activity revealed that (2S,6R)-1 is the main component, and that (S)-2 has an additive effect. In the examination of the stereochemistry-activity relationship, no copulatory behavior was elicited by (2R,6S)-1, and, furthermore, the enantiomer significantly masked the pheromonal activity of (2S,6R)-1. Glass rod dummy assays also suggested the presence of synergists. These results could elucidate the specificity of mate recognition in C. analis.

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Acknowledgments

We thank Dr. Yukihiko Toquenaga (University of Tsukuba) for providing C. analis. We are also thankful to Associate Editor Steven J. Seybold for his help on previous drafts of this manuscript.

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Authors and Affiliations

  1. Department of Bioscience, Faculty of Applied Bioscience, Tokyo University of Agriculture, Tokyo, 156-8502, Japan

    Kenji Shimomura, Takanori Mimura, Shunsuke Yajima & Kanju Ohsawa

  2. Department of Human Health and Nutrition, Shokei Gakuin University, Miyagi, 981-1295, Japan

    Kazuaki Akasaka

  3. Department of Fermentation Science, Faculty of Applied Bioscience, Tokyo University of Agriculture, Tokyo, 156-8502, Japan

    Arata Yajima

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  1. Kenji Shimomura
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  2. Kazuaki Akasaka
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  3. Arata Yajima
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Correspondence to Kenji Shimomura.

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Shimomura, K., Akasaka, K., Yajima, A. et al. Contact Sex Pheromone Components of the Seed Beetle, Callosobruchus analis (F.). J Chem Ecol 36, 955–965 (2010). https://doi.org/10.1007/s10886-010-9841-z

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