Skip to main content

1-Tridecene—male-produced sex pheromone of the tenebrionid beetle Parastizopus transgariepinus

Naturwissenschaften volume 95, pages 247–251 (2008)Cite this article

Abstract

Males of the genus Parastizopus (Coleoptera: Tenebrionidae) exhibit a special pheromone-emitting behaviour. They do a headstand, expose the aedeagus and remain in this posture for a few seconds. The pheromone emitted by P. transgariepinus was collected by solid-phase micro-extraction (100 μm polydimethylsiloxane fibre) and identified as 1-tridecene by gas chromatography/mass spectrometry. Presumably, this compound originates from the aedeagal gland, a special feature in Parastizopus, as 1-tridecene is the main compound in the gland reservoirs (23.6 ± 3.8%), accompanied by various less volatile fatty acid esters (25.2 ± 2.0%) and hydrocarbons (51.2 ± 5.7%). 1-Tridecene is also part of the pygidial defensive secretion of both sexes, together with other 1-alkenes, monoterpene hydrocarbons and 1,4-benzoquinones, but as none of these other compounds was detected during calling, the pygidial gland could be ruled out as pheromone source. Extracts of the aedeagal gland reservoirs and the pygidial defensive secretion contained comparable amounts of 1-tridecene, 1.24 ± 0.41 and 1.88 ± 0.54 μg/male, respectively. Chemo-orientation experiments using a servosphere showed that 1 μg of 1-tridecene was attractive to females but not to males.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

Fig. 1
Fig. 2

References

  • Arnaud L, Lognay G, Verscheure M, Leenaers L, Gaspar C, Haubruge E (2002) Is dimethyldecanal a common aggregation pheromone of Tribolium flour beetles? J Chem Ecol 28:523–532

    PubMed  Article  CAS  Google Scholar 

  • Batschelet E (1981) Circular statistics in biology. Academic, London

    Google Scholar 

  • Blum MS (1981) Chemical defenses of arthropods. Academic, New York

    Google Scholar 

  • Blum MS (1996) Semiochemical parsimony in the Arthropoda. Annu Rev Entomol 41:353–374

    PubMed  Article  CAS  Google Scholar 

  • Brits JA (1982) The anatomy, histology and physiology of the internal adult male reproductive system of Parastizopus armaticeps Péringuey (Coleoptera: Tenebrionidae). J Entomol Soc South Afr 45:239–260

    Google Scholar 

  • Brown WV, Doyen JT, Moore BP, Lawrence JF (1992) Chemical composition and taxonomic significance of defensive secretions of some Australian Tenebrionidae (Coleoptera). J Aust Entomol Soc 31:79–89

    Article  Google Scholar 

  • Bryning GP, Chambers J, Wakefield ME (2005) Identification of a sex pheromone from male yellow mealworm beetles, Tenebrio molitor. J Chem Ecol 31:2721–2730

    PubMed  Article  CAS  Google Scholar 

  • Francis GW, Veland K (1981) Alkylthiolation for the determination of double-bond position in linear alkenes. J Chromatogr 219:379–384

    Article  CAS  Google Scholar 

  • Geiselhardt S, Szepat T, Rasa OAE, Peschke K (2006) Defensive secretion components of the host Parastizopus armaticeps as kairomones for the cleptoparasite Eremostibes opacus. J Chem Ecol 32:767–778

    PubMed  Article  CAS  Google Scholar 

  • Keville R, Kannowski PB (1975) Sexual excitation by pheromones of the confused flour beetle. J Insect Physiol 21:81–84

    PubMed  Article  CAS  Google Scholar 

  • Leal WS (1997) Evolution of sex pheromone communication in plant-feeding scarab beetles. In: Cardé RT, Minks AK (eds) Insect pheromone research: new directions. Chapman and Hall, New York, pp 505–513

    Google Scholar 

  • Loconti JD, Roth LM (1953) Composition of the odorous secretion of Tribolium castaneum. Ann Entomol Soc Am 46:281–289

    CAS  Google Scholar 

  • Peschke K (1983) Defensive and pheromonal secretion of the tergal gland of Aleochara curtula II. Release and inhibition of male copulatory behavior. J Chem Ecol 9:13–31

    Article  CAS  Google Scholar 

  • Rasa OAE, Bisch S, Teichner T (1998) Female mate choice in a subsocial beetle: male phenotype correlates with helping potential and offspring survival. Anim Behav 56:1213–1220

    PubMed  Article  Google Scholar 

  • Suzuki T (1981) Identification of the aggregation pheromone of flour beetles Tribolium castaneum and T. confusum (Coleoptera: Tenebrionidae). Agric Biol Chem 45:1357–1363

    CAS  Google Scholar 

  • Tanaka Y, Honda H, Ohsawa K, Yamamoto I (1986) A sex attractant of the yellow mealworm, Tenebrio molitor L., and its role in the mating behavior. J Pestic Sci 11:49–55

    CAS  Google Scholar 

  • Tashiro T, Kurosawa S, Mori K (2004) Revision of the structure of the major aggregation pheromone of the broad-horned flour beetle (Gnatocerus cornutus) to (1S,4R,5R)-a-acoradiene by its synthesis. Biosci Biotechnol Biochem 68:663–670

    PubMed  Article  CAS  Google Scholar 

  • Tebayashi S, Hirai N, Suzuki T, Matsuyama S, Nakakita H, Nemoto T, Nakanishi H (1998a) Identification of (+)-acoradiene as an aggregation pheromone for Gnathocerus cornutus (F.) (Coleoptera: Tenebrionidae). J Stored Prod Res 34:99–106

    Article  CAS  Google Scholar 

  • Tebayashi S, Hirai N, Suzuki T, Matsuyama S, Nakakita H, Nemoto T, Nakanishi H (1998b) alpha-Cedren-14-al: Minor aggregation pheromone component of Gnatocerus cornutus (F.) (Coleoptera: Tenebrionidae). J Pestic Sci 23:402–406

    CAS  Google Scholar 

  • Walter F (1993) Identification of the sex pheromone of an ant, Formica lugubris (Hymenoptera, Formicidae). Naturwissenschaften 80:30–34

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank O. A. E. Rasa for valuable information about the biology of Parastizopus, the management of the Brandkaros Farm and the Northern Cape Nature Conservation Service for the collection permits and the Deutsche Forschungsgemeinschaft, Bonn, for the financial support (Pe 231/13-1,2).

Author information

Author notes

  1. Sven Geiselhardt

    Present address: Angewandte Zoologie/Ökologie der Tiere, Freie Universität Berlin, Haderslebener Straße 9, 12163, Berlin, Germany

Authors and Affiliations

  1. Institut für Biologie I, Universität Freiburg, Hauptstraße 1, 79104, Freiburg, Germany

    Sven Geiselhardt & Klaus Peschke

  2. Hansjakobstraße 14, 79199, Kirchzarten, Germany

    Peter Ockenfels

Authors
  1. Sven Geiselhardt
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Peter Ockenfels
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Klaus Peschke
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sven Geiselhardt.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Geiselhardt, S., Ockenfels, P. & Peschke, K. 1-Tridecene—male-produced sex pheromone of the tenebrionid beetle Parastizopus transgariepinus . Naturwissenschaften 95, 247–251 (2008). https://doi.org/10.1007/s00114-007-0312-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00114-007-0312-5

Keywords

  • 1-Tridecene
  • Parastizopus transgariepinus
  • Sex pheromone
  • Chemo-orientation