Journal of Chemical Ecology

, Volume 41, Issue 8, pp 732–739 | Cite as

(7E,11E)-3,5,9,11-Tetramethyltridecadienal: Sex Pheromone of the Strepsipteran Xenos peckii

  • Michael Hrabar
  • Huimin Zhai
  • Regine Gries
  • Paul W. Schaefer
  • Jason Draper
  • Robert Britton
  • Gerhard GriesEmail author


Xenos peckii is a strepsipteran parasitoid of the common North American paper wasp, Polistes fuscatus. Mate-seeking X. peckii males respond to a long-range sex pheromone emitted by the female, which remains permanently embedded within the abdomen of a mobile host wasp. During peak pheromone signalling, we excised the female from her host, severed the cephalothorax containing the pheromone gland, extracted it in hexane, and analyzed aliquots of combined extracts by coupled gas chromatographic-electroantennographic detection (GC-EAD). These analyses revealed a candidate pheromone component (CPC) that consistently elicited strong responses from male antennae. We identified the CPC as (7E,11E)-3,5,9,11-tetramethyltridecadienal based on its retention indices (RI) on three GC-columns, RI inter-column differentials, mass and NMR spectra, and synthesis of an authentic standard that matched the GC-retention and spectrometric characteristics of the CPC. For a field experiment, we prepared (7E,11E)-3,5,9R,11-tetramethyltridecadienal and (7E,11E)-3,5,9S,11-tetramethyltridecadienal. Xenos peckii males were caught in traps baited with either compound singly or a 1:1 mixture of the two but not in unbaited control traps. The sex pheromone of X. peckii resembles that reported for the strepsipterans Stylops mellittae and S. muelleri, (R,R,R)-3,5,9-trimethyldodecanal, suggesting a common biosynthetic pathway across taxonomic genera.


Twisted wing parasite Strepsiptera Stylopidia Xenidae Xenos peckii endoparasioid GC-EAD GC-MS Sex pheromone (7E,11E)-3,5,9,11-tetramethyltridecadienal 



We thank Pilar Cepeda for assistance with rearing wax moths to feed wasps; Jim Henshaw, Dan Long, Parker Nelson, Christine Payne, Ralph Payne, Dianne Pratt, and Dan Ring for permission to collect wasp nests from their properties or to hang pheromone-baited traps; Stephen DeMuth for graphical illustrations; Laurence Packer for help in locating stylopized hymenoptera populations; Caesar Inducil and Anna Löppmann for help with field collections; Rodney Bushway, Francis Drummond, Eleanor Groden, and Tamara Levitsky (University of Maine) for providing laboratory space and logistical support, and two anonymous reviewers for constructive comments. This research was supported by a Natural Sciences and Engineering Research Council of Canada (NSERC) – Discovery Grant to GG, and by an NSERC Discovery Grant and a MSFHR Career Investigator Award to RB.

Supplementary material


Xenos peckii male locating and mating with a female embedded in a Polistes fuscatus host wasp. Note repeated copulation attempts. (MP4 14256 kb)

10886_2015_613_MOESM2_ESM.docx (26 kb)
ESM 2 Details of all synthetic procedures (DOCX 25 kb)


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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Michael Hrabar
    • 1
  • Huimin Zhai
    • 1
    • 2
  • Regine Gries
    • 1
  • Paul W. Schaefer
    • 3
  • Jason Draper
    • 2
  • Robert Britton
    • 2
  • Gerhard Gries
    • 1
    Email author
  1. 1.Department of Biological SciencesSimon Fraser UniversityBurnabyCanada
  2. 2.Chemistry DepartmentSimon Fraser UniversityBurnabyCanada
  3. 3.ElktonUSA

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