Skip to main content
Log in

Biosynthesis and Site of Production of Sex Pheromone Components of the Cerambycid Beetle, Hedypathes betulinus

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

We determined the site of pheromone production tissues and a partial route for the biosynthesis of the sex pheromone in Hedypathes betulinus (Coleoptera: Cerambycidae: Lamiinae), Brazil’s main green maté pest. Pheromone was found predominantly in the prothorax of males, suggesting that this is the region of production of pheromones in this insect. Scanning electron microscopy revealed small pores that may be associated with pheromone release in males; these pores also were observed in females. A deuterium-labeled putative precursor (geranyl acetone-D5) of the sex pheromone of H. betulinus was synthesized. When applied to the prothorax of males, label from the precursor was incorporated into the pheromone components, confirming that pheromone production occurs in the prothorax and that the pheromone components are biosynthesized from geranyl acetone.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Scheme 1
Fig. 4
Fig. 5

Similar content being viewed by others

References

  • Ayres, M., Ayres Jr., M., Ayres, D. L., and Santos, A. S. 2003. BioEstat3.0, Aplicações estatística nas áreas das ciências biológicas e médicas. Sociedade Civil Mamirauá, Belém.

    Google Scholar 

  • Bastos, D. H. M., Ishimoto, E. Y., Marques, M. O. M., Ferri, A. F., and Torres, E. A. F. S. 2006. Essential oil and antioxidant activity of green mate and mate tea (Ilex paraguariensis) infusions. J. Food Comp. Analys. 19:538–543.

    Article  CAS  Google Scholar 

  • Biemont, J. C., Chaibou, M., and Pouzat, J. 1992. Localization and fine structure of the female sex pheromone-producing glands in Bruchidius atrolineatus (Pic) (Coleoptera: Bruchidae). J. Insect Morphol. Embryol. 21:251–262.

    Article  Google Scholar 

  • Brandão Filho, J. S. 1945. Uma broca do mate. Boletim Agrícola Secção Formação Agrícola Curitiba 3:55–58.

    Google Scholar 

  • CASSANELLO, A. M. L. 1993. Ciclo de vida e aspectos morfológicos de Hedypathes betulinus (Klug, 1825) (Coleoptera, Cerambycidae, Lamiinae), broca-da-erva-mate (Ilex paraguariensis St. Hil.), pp. 59, Dissertação de Mestrado, UFPR, Curitiba.

  • Dowd, P. F. and Bartelt, R. J. 1993. Aggregation pheromone gland of Carpophilus freemani (Coleoptera: Nitidulidae) and gland distribution among other sap beetles. Ann. Ent. Soc. Am. 86:464–469.

    Google Scholar 

  • Fonseca, M. G. and Zarbin, P. H. G. 2009. Mating behaviour and evidence for sex-specific pheromones in Hedypathes betulinus (Coleoptera: Cerambycidade: Lamiinae). J. Appl. Entomol. 133:695–701.

    Article  CAS  Google Scholar 

  • Fonseca, M. G., Vidal, D. M., and Zarbin, P. H. G. 2010. Male-produced sex pheromone of the cerambycid beetle Hedypathes betulinus: Chemical Identification and biological activity. J. Chem. Ecol. 36:1132–1139.

    Article  PubMed  CAS  Google Scholar 

  • Gäbler, A. and Boland, W. 1991. Stereochemical studies on homoterpene biosynthesis in higher plants; mechanistic, phylogenetic, and ecological aspects. Helv. Chim. Acta 74:1773–1789.

    Article  Google Scholar 

  • Hanks, L. M., Millar, J. G., Moreira, J. A., Barbour, J. D., Lacey, E. S., McElfresh, J. S., Reuter, F. R., and Ray, A. M. 2007. Using generic pheromone lures to expedite identification of aggregation pheromones for the cerambycid beetles Xylotrechus nauticus, Phymatodes lecontei, and Neoclytus modestus modestus. J. Chem. Ecol. 33:889–907.

    Article  PubMed  CAS  Google Scholar 

  • Ivastschenko, I. I. and Adamenko, E. A. 1980. Place of pheromone formation in females of Selatosomus latus (Coleoptera: Elateridae). Zoologicheski Zhurnal 59:225–228.

    Google Scholar 

  • Kiyota, R., Yamakawa, R., Iwabuchi, K., Hoshino, K., and Ando, T. 2009. Synthesis of the deuterated sex pheromone components of the grape borer, Xylotrechus pyrrhoderus. Biosci. Biotechnol. Biochem. 73:2252–2256.

    Article  PubMed  CAS  Google Scholar 

  • Lacey, E. S., Moreira, J. A., Millar, J. G., Ray, A. M., and Hanks, L. M. 2007a. Male-produced aggregation pheromone of the cerambycid beetle Neoclytus mucronatus mucronatus. Entomol. Exp. Appl. 122:171–179.

    Article  CAS  Google Scholar 

  • Lacey, E. S., Ray, A. M., and Hanks, L. M. 2007b. Calling behavior of the cerambycid beetle Neoclytus acuminatus acuminatus (F.). J. Insect Behav. 20:117–127.

    Article  Google Scholar 

  • Leal, W. S., Zarbin, P. H. G., Wojtasek, H., and Ferreira, J. T. 1999. Biosynthesis of scarab beetle pheromones. Enantioselective 8-hydroxylation of fatty acids. Eur. J. Biochem. 259:175–180.

    Article  PubMed  CAS  Google Scholar 

  • Levinson, H. Z., Levinson, A. R., Kahn, G. E., and Schafer, K. 1983. Occurrence of a pheromone-producing gland in female tabacco beetles. Experientia 39:1095–1097.

    Article  Google Scholar 

  • Lew, A. C. and Ball, H. J. 1978. The structure of the apparent pheromone-secreting cells in female Diabrotica virgifera. Ann. Ent. Soc. Am. 71:685–688.

    Google Scholar 

  • Liendo, C., Morillo, F., Sanchez, P., Munoz, W., Guerra, J., Cabrera, A., and Hernandez, J. V. 2005. Olfactory behavior and electroantennographic response of the cocoa beetle, Steirastoma breve (Coleoptera: Cerambycidae). Fla. Entomol. 88:117–122.

    Google Scholar 

  • Mazuchowski, J. Z. 1991. pp. 104, Manual da erva-mate (Ilex paraguariensis St. Hil.). Emater, Curitiba.

    Google Scholar 

  • Mitchell, R. F., Grahan, E. E., Wong, J. C. H., Reagel, P. F., Striman, B. L., Hughes, G. P., Paschen, M. A., Ginel, M. D., Millar, J. D., and Hanks, L. M. 2011. Fuscumol and fuscumol acetate are general attractants for many species of cerambycid beetles in the subfamily Lamiinae. Ent. Exp Appl. 141:71–77.

    Article  CAS  Google Scholar 

  • Ray, A. M., Lacey, E. S., and Hanks, L. M. 2006. Predicted taxonomic patterns in pheromone production by longhorned beetles. Naturwissenschaften 93:543–550.

    Article  PubMed  CAS  Google Scholar 

  • Reddy, G. V. and Guerrero, A. 2004. Interactions of insect pheromones and plant semiochemicals. Trends Plant Sci. 9:253–261.

    Article  PubMed  CAS  Google Scholar 

  • Seybold, S. J. and Vanderwel, D. 2003. Biosynthesis and endocrine regulation of pheromone production in the Coleoptera, pp. 137–200, in G. J. Blomquist and R. G. Vogt (eds.), Insect pheromone biochemistry and molecular biology. Elsevier Academic Press, London.

    Chapter  Google Scholar 

  • Silk, P. J., Sweeney, J., Wu, J., Price, J., Gutowski, L. M., and Kettela, E. G. 2007. Evidence for a male-produced pheromone in Tetropium fuscum (F.) and Tetropium cinnamopterum (Kirby) (Coleoptera: Cerambycidae). Naturwissenschaften 94:697–701.

    Article  PubMed  CAS  Google Scholar 

  • Silverstein, R. M., Webster, F. X., and Kiemle, D. J. 2005. Spectrometric identification of organic compounds. John Wiley & Sons, New York.

    Google Scholar 

  • Tada, S. and Leal, W. S. 1997. Localization and morphology of sex pheromone glands in scarab Beetles. J. Chem. Ecol. 23:903–915.

    Article  CAS  Google Scholar 

  • Thompson, A. C. and Mitlin, N. 1979. Biosynthesis of the sex pheromone of the male boll weevil from monoterpene precursors. Insect Biochem. 9:293–294.

    Article  CAS  Google Scholar 

  • Tillman, J. A., Seybold, S. J., Jurenka, R. A., and Blomquist, G. J. 1999. Insect pheromones—an overview of biosynthesis and endocrine regulation. Insect Biochem. Mol. Biol. 29:481–514.

    Article  PubMed  CAS  Google Scholar 

  • Vidal, D. M., Fonseca, M. G., and Zarbin, P. H. G. 2010. Enantioselective synthesis and absolute configuration of the sex pheromone of Hedypathes betulinus (Coleoptera; Cerambycidae). Tetrahedron Lett. 51:6704–6706.

    Article  CAS  Google Scholar 

  • Zarbin, P. H. G., Ferreira, J. T. B., and Leal, W. S. 1999. Metodologias gerais empregadas no isolamento e identificação estrutural de feromônio de insetos. Quím. Nova 22:263–268.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank VIER farm for providing access to their fields for the insect collections. This research was supported by CNPq, INCT de Semioquímicos na Agricultura, and CAPES. PHGZ thanks Carla F. Fávaro - Laboratório de Semioquímicos UFPR, for strong support on the preparation of the revised version of the manuscript.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Paulo H. G. Zarbin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zarbin, P.H.G., Fonseca, M.G., Szczerbowski, D. et al. Biosynthesis and Site of Production of Sex Pheromone Components of the Cerambycid Beetle, Hedypathes betulinus . J Chem Ecol 39, 358–363 (2013). https://doi.org/10.1007/s10886-013-0252-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10886-013-0252-9

Keywords

Navigation