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Contact Sex Pheromone Activity of Synthetic Gomadalactones in Male White-Spotted Longhorn Beetle, Anoplophora malasiaca (Coleoptera: Cerambycidae)

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Abstract

The elytra of females of the white-spotted longhorn beetle, Anoplophora malasiaca (Coleoptera: Cerambycidae), are coated with a contact sex pheromone, which was previously shown to be composed of at least three chemical groups. Individually, the chemical groups had little pheromonal activity, but a blend of all three exhibited activity equal to that of the crude female extract. Two groups are female-specific aliphatic hydrocarbons and ketones, which were previously synthesized and confirmed to elicit mating behavior. The third group consists of three lactones, gomadalactones A, B, and C, whose chemical structures were previously identified. These have now been synthesized, and the contact sex pheromone activities of synthetic gomadalactones A, B, and C, and the diastereomer of gomadalactone C, were tested in bioassays in this study. When tested in combination with synthetic hydrocarbons and ketones at the same doses as found in female elytra extract, the individual gomadalactones and a blend showed potent pheromonal activity equivalent to that of the crude extract of the elytra of female beetles. This completes the identification of the essential components of the contact sex pheromone of A. malasiaca. Redundancy of components in the hydrocarbon and ketone groups required to elicit mating behavior was observed previously, and this was also true for the gomadalactones.

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Acknowledgements

We thank Yoshinobu Kiyosue, Kazuhiro Harada, Minoru Narahara, Koji Nakashima, Michiko Goto, Akira Tamanoi, and Yuta Goto of the Oita Prefectural Citrus Experiment Station; Seishi Toda, Shigekatsu Noda, and Yutaka Gyoutoku of the Kumamoto Prefectural Agricultural Research Center; and Shinichi Osaki and Mariko Yoshida of the Uki Agricultural Improvement Extension Center for collecting the insects used in this study. Thanks are also due to Shuko Iwata, Akiko Shimizu, Kazumi Hojo, Taeko Maeda, and Ikuko Hashimoto for assistance with the behavioral bioassays and insect rearing. This project was partially supported by a Grant-in-Aid for Scientific Research (C) (17 K07686) and a Grant-in-Aid for Challenging Exploratory Research (16 K14867) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We thank Harry Taylor, PhD, and Mallory Eckstut, PhD, from Edanz Group (www.edanzediting.com/ac) for editing drafts of this manuscript.

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Author notes

  1. Nao Fujiwara-Tsujii, Hiroe Yasui & Tetsuya Yasuda

    Present address: Chemical Ecology Group, Central Region Agricultural Research Center, National Agriculture and Food Research Organization (NARO), Kannondai, Tsukuba, Ibaraki, 305-8666, Japan

  2. Sadao Wakamura

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

  3. Toshiharu Akino

    Present address: Applied Insect Laboratory, Kyoto Institute of Technology, Saga-ippongi-cho 1, Ukyo-ku, Kyoto, 616-8354, Japan

  4. Midori Fukaya

    Present address: Laboratory of Forest Zoology, College of Bioresource Sciences, Nihon University, Fujisawa, Kanagawa, 252-0880, Japan

  5. Nao Fujiwara-Tsujii and Hiroe Yasui contributed equally to this work.

Authors and Affiliations

  1. Laboratory of Insect Behavior, National Institute of Agrobiological Sciences (NIAS), Ohwashi, Tsukuba, Ibaraki, 305-0851, Japan

    Nao Fujiwara-Tsujii, Hiroe Yasui, Tetsuya Yasuda, Sadao Wakamura, Toshiharu Akino & Midori Fukaya

  2. Faculty of Engineering, Niigata University, 2-Nocho, Ikarashi, Nishi-ku, Niigata, 950-2181, Japan

    Toshio Suzuki & Takashi Hoshi

  3. Graduate School of Science and Technology, Niigata University, 2-Nocho, Ikarashi, Nishi-ku, Niigata, 950-2181, Japan

    Hisahiro Hagiwara

  4. Bioactive Compounds Team, Advanced Analysis Center, National Agriculture and Food Research Organization (NARO), Kannondai, Tsukuba, Ibaraki, 305-8642, Japan

    Hiroshi Ono

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  1. Nao Fujiwara-Tsujii
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  2. Hiroe Yasui
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Correspondence to Nao Fujiwara-Tsujii.

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Fujiwara-Tsujii, N., Yasui, H., Yasuda, T. et al. Contact Sex Pheromone Activity of Synthetic Gomadalactones in Male White-Spotted Longhorn Beetle, Anoplophora malasiaca (Coleoptera: Cerambycidae). J Chem Ecol 45, 440–446 (2019). https://doi.org/10.1007/s10886-019-01069-1

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