Skip to main content

4-Methylquinazoline is a Minor Component of the Male Sex Pheromone in Nasonia vitripennis


We identified 4-methylquinazoline (4-MeQ) as a minor component of the male sex pheromone of the parasitoid Nasonia vitripennis. Like the major components (4R,5R)- and (4R,5S)-5-hydroxy-4-decanolide (HDL), 4-MeQ is synthesized in the abdomen of males. At doses of 6 or 1 ng, 4-MeQ synergized the response of virgin females to the HDL-diastereomers in a still-air olfactometer, but was not attractive as a single component. 4-MeQ is also responsible for the characteristic medicinal odor of N. vitripennis males.

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

Fig. 1


  • Bailey, R. J. E., Birkett, M. A., Ingvarsdottir, A., Mordue, A. J., Mordue, W., O’Shea, B., Pickett, J. A., and Wadhams, L. J. 2006. The role of semiochemicals in host location and non-host avoidance by salmon louse (Lepeophtheirus salmonis) copepodids. Can. J. Fish. Aqu. Sci. 63:448–456.

    Article  CAS  Google Scholar 

  • Bergmann, J., Brynolf, A., Elman, B., and Vuorinen, E. 1986. Synthesis of quinazolines. Tetrahedron 42:3697–3706.

    Article  Google Scholar 

  • Cônsoli, F. L., Williams, H. J., Vinson, S. B., Matthews, R. W., and Cooperband, M. F. 2002. trans-Bergamotenes-male pheromone of the ectoparasitoid Melittobia digitata. J. Chem. Ecol 28:1675–1689.

    Article  Google Scholar 

  • Cruz-López, L. and Morgan, D. 1995. Chemical investigation of aggregation behavior of Triatoma bugs (Hemiptera: Reduviidae). J. Chem. Ecol 21:2069–2078.

    Article  Google Scholar 

  • D’yakonov, A. L. and Telezhenetskaya, M. V. 1997. Quinazoline alkaloids in nature. Chem. Nat. Prod 33:221–267.

    CAS  Google Scholar 

  • Garbe, L. A. and Tressl, R. 2003. Metabolism of deuterated isomeric 6,7-dihydroxydodecanoic acids in Saccharomyces cerevisiae—diastereo- and enantioselective formation and characterization of 5-hydroxydecano-4-lactone (= 4,5-dihydro-5-(1-hydroxyhexyl)furan-2(3H)-one) isomers. Helv. Chim. Acta 86:2349–2363.

    Article  CAS  Google Scholar 

  • Ruther, J., Stahl, L. M., Steiner, S., Garbe, L. A., and Tolasch, T. 2007. A male sex pheromone in a parasitic wasp and control of the behavioral response by the female’s mating status. J. Exp. Biol 210:2163–2169.

    PubMed  Article  CAS  Google Scholar 

  • Steiner, S., Hermann, N., and Ruther, J. 2006. Characterization of a female-produced courtship pheromone in the parasitoid Nasonia vitripennis. J. Chem. Ecol 32:1687–1702.

    PubMed  Article  CAS  Google Scholar 

  • Van den Assem, J., Jachmann, F., and Simbolotti, P. 1980. Courtship behaviour of Nasonia vitripennis (Hym., Pteromalidae): Some qualitative, experimental evidence for the role of pheromones. Behaviour 75:301–307.

    Google Scholar 

  • Zhang, J. X., Soini, H. A., Bruce, K. E., Wiesler, D., Woodley, S. K., Baum, M. J., and Novotny, M. V. 2005. Putative chemosignals of the ferret (Mustela furo) associated with individual and gender recognition. Chem. Senses 30:727–737.

    PubMed  Article  CAS  Google Scholar 

Download references


This research was funded by the Deutsche Forschungsgemeinschaft (DFG, grant RU-717/8-1). J. R. was supported by a Heisenberg fellowship of the DFG (grant RU-717/7-1). The authors thank Waltraud Poppe (Technical University of Berlin) for technical assistance.

Author information

Authors and Affiliations


Corresponding author

Correspondence to Joachim Ruther.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Ruther, J., Steiner, S. & Garbe, LA. 4-Methylquinazoline is a Minor Component of the Male Sex Pheromone in Nasonia vitripennis . J Chem Ecol 34, 99–102 (2008).

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI:


  • Nasonia vitripennis
  • Parasitoid
  • Pteromalidae
  • Sex pheromone
  • 4-methylquinazoline