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Chemical Ecology of Astigmatid Mites LXXXVII. S-(+)-Isopiperitenone: Re-identification of the Alarm Pheromone as the Female Sex Pheromone in Tyrophagus similis (Acari: Acaridae)

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Abstract

Behavioral analysis revealed that S-(+)-isopiperitenone [(S)-3-methyl-6-isopropenyl-2-cyclohexen-1-one], previously identified as an alarm pheromone, is also the female sex pheromone of Tyrophagus similis (Astigmata: Acaridae), showing maximum male attraction at a dose of 0.1 female equivalent. Although the antipode, R-(−)-isopiperitenone, was not detectable in the mite extract, this synthetic optical isomer (80% e.e.) also induced activity at a dose of 100 ng, a response indicative of S-(+)-isopiperitenone being the active compound. The average content was determined to be 38.5 ng per female and 19.8 ng per male. This is the first example of an astigmatid mite species possessing a compound that functions as an alarm as well as a sex pheromone.

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Acknowledgements

This study was supported partly by a Grant-in-aid for Scientific Research (no. 22380068) from the Ministry of Education, Culture, Sports, Science and Technology of Japan and by Development Works for Practical Technology driving novel Policies for Agriculture, Forestry and Fisheries (no. 22005) from the Ministry of Agriculture, Forestry and Fisheries.

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  1. Yasumasa Kuwahara

    Present address: Department of Bioenvironmental Science, Kyoto Gakuen University, Kameoka-shi, Kyoto, 621-8555, Japan

Authors and Affiliations

  1. Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan

    Gorou Maruno, Naoki Mori & Yasumasa Kuwahara

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  1. Gorou Maruno
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  2. Naoki Mori
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  3. Yasumasa Kuwahara
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Correspondence to Naoki Mori.

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Maruno, G., Mori, N. & Kuwahara, Y. Chemical Ecology of Astigmatid Mites LXXXVII. S-(+)-Isopiperitenone: Re-identification of the Alarm Pheromone as the Female Sex Pheromone in Tyrophagus similis (Acari: Acaridae). J Chem Ecol 38, 36–41 (2012). https://doi.org/10.1007/s10886-012-0059-0

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