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

  • Nao Fujiwara-TsujiiEmail author
  • Hiroe Yasui
  • Tetsuya Yasuda
  • Sadao Wakamura
  • Toshiharu Akino
  • Midori Fukaya
  • Toshio Suzuki
  • Takashi Hoshi
  • Hisahiro Hagiwara
  • Hiroshi Ono
Article
  • 73 Downloads

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.

Keywords

Contact sex pheromone Gomadalactones White-spotted longhorn beetle Anoplophora malasiaca Mating behavior 

Notes

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.

References

  1. Akino T, Fukaya M, Yasui H, Wakamura S (2001) Sexual dimorphism in cuticular hydrocarbons of the white-spotted longicorn beetle, Anoplophora malasiaca (Coleoptera: Cerambycidae). Entomol Sci 4:271–277Google Scholar
  2. Barbour JD, Lacey ES, Hanks LM (2007) Cuticular hydrocarbons mediate mate recognition in a species of longhorned beetle (Coleoptera: Cerambycidae) of the primitive subfamily Prioninae. Ann Entomol Soc Am 100:333–338CrossRefGoogle Scholar
  3. Brodie BS, Wickham JD, Teale SA (2012) The effect of sex and maturation on cuticular semiochemicals in Monochamus scutellatus (Coleoptera: Cerambycidae). Can Entomol 144:801–808CrossRefGoogle Scholar
  4. Fujiwara-Tsujii N, Yasui H, Wakamura S, Hashimoto I, Minamishima M (2012) White-spotted longicorn beetle, Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae), with a blueberry host may utilize original host chemicals for mate location. Appl Entomol Zool 47:103–110CrossRefGoogle Scholar
  5. Fukaya M, Yasuda T, Wakamura S, Honda H (1996) Reproductive biology of the yellow-spotted longicorn beetle, Psacothea hilaris (Pascoe)(Coleoptera: Cerambycidae). III. Identification of contact sex pheromone on female body surface. J Chem Ecol 22:259–270CrossRefGoogle Scholar
  6. Fukaya M, Akino T, Yasuda T, Tatsuki S, Wakamura S (1999) Mating sequence and evidence for synergistic component in female contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae). Entomol Sci 2:183–193Google Scholar
  7. Fukaya M, Akino T, Yasuda T, Wakamura S, Satoda S, Senda S (2000) Hydrocarbon components in contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae) and pheromonal activity of synthetic hydrocarbons. Entomol Sci 3:211–218Google Scholar
  8. Ginzel MD, Millar JG, Hanks LM (2003) (Z)-9-Pentacosene− contact sex pheromone of the locust borer, Megacyllene robiniae. Chemoecology 13:135–141CrossRefGoogle Scholar
  9. Ginzel MD, Moreira JA, Ray AM, Millar JG, Hanks LM (2006) (Z)-9-Nonacosene— major component of the contact sex pheromone of the beetle Megacyllene caryae. J Chem Eco 32:435–451CrossRefGoogle Scholar
  10. Higuchi T, Saika T, Senda S, Mizobata T, Kawata Y, Nagai J (1997) Development of biorational pest control formation against longicorn beetles using a fungus, Beauveria brongniartii (Sacc.) Petch. J Ferment Bioeng 84:236–243CrossRefGoogle Scholar
  11. Lacey ES, Ginzel MD, Millar JG, Hanks LM (2008) 7-Methylheptacosane is a major component of the contact sex pheromone of the cerambycid beetle Neoclytus acuminatus acuminatus. Physiol Entomol 33:209–216CrossRefGoogle Scholar
  12. Lingafelter SW, Hoebeke ER (2002) Revision of Anoplophora (Coleoptera: Cerambycidae). Entomological Society of Washington, Washington DC, p 236Google Scholar
  13. Makihara H (2000) True taxonomy and distribution of Anoplophora cerambycid beetles in East Asia. Shinrin-boeki (Forest Pests) 49:180–194 (in Japanese)Google Scholar
  14. Makihara H (2007) Illustrated key & description of Lamiinae. In: Ohbayashi N, Niisato T (eds) Longicorn beetles of Japan: manual with keys and illustrations. Tokai University Press, Tokyo, pp 576–605 (In Japanese)Google Scholar
  15. Mori K (2007) Absolute configuration of gomadalactones A, B and C, the components of the contact sex pheromone of Anoplophora malasiaca. Tetrahedron Lett 48:5609–5611CrossRefGoogle Scholar
  16. Muraji M, Wakamura S, Yasui H, Arakaki N, Sadoyama Y, Ohno S, Matsuhira K (2011) Genetic variation of the white-spotted longicorn beetle Anoplophora spp. (Coleoptera: Cerambycidae) in Japan detected by mitochondrial DNA sequence. Appl Entomol Zool 46:363–373CrossRefGoogle Scholar
  17. Ohbayashi N (1992) Genus Anoplophora Hope, 1839. In: Ohbayashi N et al (eds) An illustrated guide to identification of longicorn beetles of Japan. Tokai University Press, Tokyo, pp 583–584Google Scholar
  18. Suzuki T, Hagiwara H, Uchida H, Tsujii N, Ono H. (2017) Japan Patent JP2017–095381. https://astamuse.com/ja/published/JP/No/2017095381. (in Japanese). Accessed 1 June 2017
  19. Tanigaki T, Yamaoka R, Sota T (2007) The role of cuticular hydrocarbons in mating and conspecific recognition in the closely related longicorn beetles Pidonia grallatrix and P. takechii. Zool Sci 24:39–45CrossRefGoogle Scholar
  20. Yasui H (2009) Chemical communication in mate location and recognition in the white-spotted longicorn beetle, Anoplophora malasiaca (Coleoptera: Cerambycidae). Appl Entomol Zool 44:183–194CrossRefGoogle Scholar
  21. Yasui H, Akino T, Yasuda T, Fukaya M, Ono H, Wakamura S (2003) Ketone components in contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca, and pheromonal activity of synthetic ketones. Entomol Exp Appl 107:167–176CrossRefGoogle Scholar
  22. Yasui H, Akino T, Yasuda T, Fukaya M, Wakamura S, Ono H (2007a) Gomadalactones A, B, and C: novel 3-oxabicyclo[3.3.0]octane compounds in the contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca. Tetrahedron Lett 48:2395–2400CrossRefGoogle Scholar
  23. Yasui H, Fujiwara-Tsujii N, Wakamura S (2011) Volatile attractant phytochemicals for a population of white-spotted longicorn beetles Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae) fed on willow differ from attractants for a population fed on citrus. Chemoecology 21(2):51-58CrossRefGoogle Scholar
  24. Yasui H, Yasuda T, Fukaya M, Akino T, Wakamura S, Hirai Y, Kawasaki K, Ono H, Narahara M, Kousa K, Fukuda T (2007b) Host plant chemicals serve intraspecific communication in the white-spotted longicorn beetle, Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae). Appl Entomol Zool 42:255–268CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Nao Fujiwara-Tsujii
    • 1
    • 2
    Email author
  • Hiroe Yasui
    • 1
    • 2
  • Tetsuya Yasuda
    • 1
    • 2
  • Sadao Wakamura
    • 1
    • 3
  • Toshiharu Akino
    • 1
    • 4
  • Midori Fukaya
    • 1
    • 5
  • Toshio Suzuki
    • 6
  • Takashi Hoshi
    • 6
  • Hisahiro Hagiwara
    • 7
  • Hiroshi Ono
    • 8
  1. 1.Laboratory of Insect BehaviorNational Institute of Agrobiological Sciences (NIAS)IbarakiJapan
  2. 2.Chemical Ecology Group, Central Region Agricultural Research CenterNational Agriculture and Food Research Organization (NARO)IbarakiJapan
  3. 3.Faculty of Bioenvironmental ScienceKyoto Gakuen UniversityKyotoJapan
  4. 4.Applied Insect LaboratoryKyoto Institute of TechnologyKyotoJapan
  5. 5.Laboratory of Forest Zoology, College of Bioresource SciencesNihon UniversityFujisawaJapan
  6. 6.Faculty of EngineeringNiigata UniversityNiigataJapan
  7. 7.Graduate School of Science and TechnologyNiigata UniversityNiigataJapan
  8. 8.Bioactive Compounds Team, Advanced Analysis CenterNational Agriculture and Food Research Organization (NARO)IbarakiJapan

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