Skip to main content

Advertisement

SpringerLink
Log in

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

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

Abstract

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.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  • Amorelli B, Arruda ME, Belko RP, Cai T, Closson AP, Giffin NL, Mertz GJ, Monteleone MG (2015) Novel organoleptic compounds. U.S. Pat. Appl. Publ. US 20150057207

  • Appel R (1975) Tertiary phosphane/tetrachloromethane, a versatile reagent for chlorination, dehydration, and P—N linkage. Angew Chem Int Ed Engl 14:801–811

    Article  Google Scholar 

  • Arn H, Städler E, Rausher S (1975) The electroantennographic detector – a selective and sensitive tool in the gas chromatographic analysis of insect pheromones. Z Naturforsch 30c:722–725

    CAS  Google Scholar 

  • Borden JH, Chong L, McLean JA, Slessor KN, Mori K (1976) Gnathotrichus sulcatus: synergistic response to enantiomers of the aggregation pheromone sulcatol. Science 192:894–896

    Article  CAS  PubMed  Google Scholar 

  • Borden JH, Handley JR, McLean JA, Silverstein RM, Chong L, Slessor KN, Johnston BD, Shuler HR (1980) Enantiomer-based specificity in pheromone communication by two sympatric Gnathotrichus species (Coleoptera: Scolytidae). J Chem Ecol 6:445–456

    Article  Google Scholar 

  • Boussau B, Walton Z, Delgado JA, Collantes F, Beani L, Stewart IJ, Cameron SA, Whitfield JB, Johnston S, Holland PWH, Bachtrog D, Kathirithamby J, Huelsenbeck JP (2014) Strepsiptera, phylogeomics and the long branch attraction problem. PloS ONE 9(10):e107709

    Article  PubMed Central  PubMed  Google Scholar 

  • Cvačka J, Jiroš P, Kalinová B, Straka J, Černá K, Šebesta P, Tomčala A, Vašíčková K, Jahn U, Šobotník J (2012) Stylopsal: the first identified female-produced sex pheromone of Strepsiptera. J Chem Ecol 38:1483–1491

    Article  PubMed  Google Scholar 

  • Dallai R, Lupetti P, Guisti F, Mercati D, Paccagnini E, Turillazzi S, Beani L, Kathirithamby J (2004) Fine structure of the Nassonow’s gland in the neotenic endoparasitic female Xenos vesparum (Rossi) (Strepsiptera, Insecta). Tissue Cell 36:211–220

    Article  CAS  PubMed  Google Scholar 

  • Evans DA, Ennis MD, Mathre DJ (1982) Asymmetric alkylation reactions of chiral imide enolates. A practical approach to the enantioselective synthesis of α-substituted carboxylic acid derivatives. J Am Chem Soc 104:1737–1739

    Article  CAS  Google Scholar 

  • Fotiadou AD, Zografos AL (2011) Accessing the structural diversity of pyridine alkaloids: concise total synthesis of rac-citridone A. Org Lett 13:4592–4595

    Article  CAS  PubMed  Google Scholar 

  • Francke W, Dettner K (2005) Chemical signalling in beetles. In: Schulz S (ed) The chemistry of pheromones and other semiochemicals II: topics in current chemistry 240. Springer, Berlin, Heidelberg, New York, pp 85–166

    Google Scholar 

  • Gries G, Gries R, Schaefer PW, Gotoh T, Higashiura Y (1999) Sex pheromone components of pink gypsy moth, Lymantria mathura. Naturwissenschaften 86:235–238

    Article  CAS  Google Scholar 

  • Gries R, Khashkin G, Gries G, Bennett RG, King S, Morewood P, Slessor KN, Morewood WD (2002) (Z,Z)-4,7-Tridecadien-(S)-2-yl acetate: sex pheromone of Douglas-fir cone gall midge contarinia oregonensis. J Chem Ecol 28:2283–2297

    Article  CAS  PubMed  Google Scholar 

  • Gries R, Khaskin G, Khaskin E, Foltz JL, Schaefer PW, Gries G (2003) Enantiomers of (Z,Z)-6,9-heneicosadien-11-ol: sex pheromone components of Orgyia detrita. J Chem Ecol 29:2201–2212

    Article  CAS  PubMed  Google Scholar 

  • Gries R, Khashkin G, Schaefer PW, Hahn R, Gotoh T, Gries G (2005) (7R,8S)-cis-7,8-Epoxy-2-methyloctadec-17-ene: a novel trace component from the sex pheromone gland of gypsy moth, Lymentria dispar. J Chem Ecol 31:49–62

    Article  CAS  PubMed  Google Scholar 

  • Hanessian S, Mascitti V, Giroux S (2004) Total synthesis of the cytotoxic cyclodepsipeptide (−)-doliculide: the “ester” effect in acyclic 1,3-induction of deoxypropionates. Proc Natl Acad Sci U S A 101:11996–12001

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Hrabar M, Danci A, McCann S, Schaefer P, Gries G (2014) New findings on life history traits of Xenos peckii (Strepsiptera, Xenidae). Can Entomol 146:512–527

    Google Scholar 

  • Kathirithamby J (2009) Host-parasitoid associations in strepsiptera. Annu Rev Entomol 54:227–249

    Article  CAS  PubMed  Google Scholar 

  • Krombein KV, Hurd PD Jr (1979) Catalog of hymenoptera in America North of Mexico. Volume 2 apocrita (Aculeata). Smithsonian Institution Press, Washington

    Google Scholar 

  • Lagoutte R, Šebesta P, Jiroš P, Kalinová B, Jirošová A, Straka J, Černá K, Šobotník J, Cvačka J, Jahn U (2013) Total synthesis, proof of absolute configuration, and biosynthetic origin of stylopsal, the first isolated sex pheromone of Strepsiptera. Chem Eur J 19:8515–8524

    Article  CAS  PubMed  Google Scholar 

  • Millar JG, Giblin M, Barton D, Morrison A, Underhill EW (1990) Synthesis and field testing of enantiomers of 6Z,9Z-cis-epoxydienes as sex attractants for geometrid moths. J Chem Ecol 16:2317–2339

    Article  CAS  PubMed  Google Scholar 

  • Millar JG, Giblin M, Barton D, Underhill EW (1991) Chiral lepidopteran sex attractants: blends of optically active C20 and C21 diene epoxides as sex attractants for geometrid and noctuid moths (Lepidoptera). Environ Entomol 20:450–457

    Article  CAS  Google Scholar 

  • Payne TL, Richerson JV, Dickens JC, West JR, Mori K, Berisford CW, Hedden RL, Vité JP, Blum MS (1982) Southern pine beetle: olfactory receptor and behaviour discrimination of enantiomers of the attractant pheromone frontalin. J Chem Ecol 8:873–881

    Article  CAS  PubMed  Google Scholar 

  • Rodstein J, Millar JG, Barbour JD, McElfresh JS, Wright IM, Barbour KS, Ray AM, Hanks LM (2011) Determination of the relative and absolute configurations of the female-produced sex pheromone of the cerambycid beetle Prionus californicus. J Chem Ecol 37:114–124

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Schaefer PW, Jiang M, Gries R, Gries G, Wu J (2013) Attraction of male Lymantria schaeferi Schintlmeister (Lepidoptera: Erebidae: Lymantriinae) to traps baited with (+)-xylinalure in Jiangxi Province, China. Life Excitement Biol 1:95–99

    Article  Google Scholar 

  • Schmidt Y, Lehr K, Colas L, Breit B (2012) Assignment of relative configuration of desoxypropionates by 1H NMR spectroscopy: method development, proof of principle by asymmetric total synthesis of xylarinic acid A and applications. Chem Eur J 18:7071–7081

    Article  CAS  PubMed  Google Scholar 

  • Schraeder SH (1924) Reproduction in Achroschismus wheeleri Pierce. J Morphol Physiol 39:157–205

    Article  Google Scholar 

  • Staddon BW, Everton IJ (1980) Haemolymph of milkweed bug Oncopeltus fasciatus (Heteroptera: Lygaeidae): inorganic constituents and amino acids. Comp Biochem Physiol 65A:371–374

    Article  CAS  Google Scholar 

  • Tolasch T, Kehl S, Dötterl S (2010) Sex pheromone of a twisted-wing parasite. Lecture on the 26th Annual Meeting of the ISCE, August 2nd 2010, Tours, France

  • Tolasch T, Kehl S, Dötterl S (2012) First sex pheromone of the order strepsiptera: (3R,5R,9R)-3,5,9-trimethyldodecanal in Stylops melittae Kirby, 1802. J Chem Ecol 38:1493–1503

    Article  CAS  PubMed  Google Scholar 

  • Van den Dool H, Kratz PD (1963) A generalization of the retention index system including linear temperature-programmed gas–liquid partition chromatography. J Chromatogr 2:463–471

    Article  Google Scholar 

  • Wood DL (1982) The role of pheromones, kairomones, and allomones in the host selection and colonization behaviour of bark beetles. Annu Rev Entomol 27:411–446

    Article  CAS  Google Scholar 

Download references

Acknowledgments

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.

Author information

Authors and Affiliations

  1. Department of Biological Sciences, Simon Fraser University, Burnaby, BC, V5A 1S6, Canada

    Michael Hrabar, Huimin Zhai, Regine Gries & Gerhard Gries

  2. Chemistry Department, Simon Fraser University, Burnaby, BC, V5A 1S6, Canada

    Huimin Zhai, Jason Draper & Robert Britton

  3. 4 Dare Drive, Elkton, MD, 21921, USA

    Paul W. Schaefer

Authors
  1. Michael Hrabar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Huimin Zhai
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Regine Gries
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Paul W. Schaefer
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jason Draper
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Robert Britton
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Gerhard Gries
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Gerhard Gries.

Electronic supplementary material

Below is the link to the electronic 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)

ESM 2

Details of all synthetic procedures (DOCX 25 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hrabar, M., Zhai, H., Gries, R. et al. (7E,11E)-3,5,9,11-Tetramethyltridecadienal: Sex Pheromone of the Strepsipteran Xenos peckii . J Chem Ecol 41, 732–739 (2015). https://doi.org/10.1007/s10886-015-0613-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10886-015-0613-7

Keywords

Search

Navigation