Journal of Chemical Ecology

, Volume 44, Issue 12, pp 1115–1119 | Cite as

(Z)-7-Hexadecene is an Aggregation-Sex Pheromone Produced by Males of the South American Cerambycid Beetle Susuacanga octoguttata

  • Weliton D. SilvaEmail author
  • José Maurício S. Bento
  • Lawrence M. Hanks
  • Jocelyn G. Millar
Rapid Communication


We describe the identification, synthesis, and field bioassays of a novel aggregation-sex pheromone produced by males of Susuacanga octoguttata (Germar), a South American cerambycid beetle. Analyses of extracts of headspace volatiles produced by adult beetles revealed a sex-specific compound emitted by males which was identified as (Z)-7-hexadecene by microchemical and spectroscopic analyses. The synthesized pheromone was attractive to beetles of both sexes in field trials. This unsaturated hydrocarbon motif is unprecedented among cerambycid pheromones identified to date. During field bioassays, we serendipitously discovered that adults of S. octoguttata trapped in two Brazilian biomes differed considerably in elytral markings, although males from both populations produced (Z)-7-hexadecene as an aggregation-sex pheromone.


Semiochemical Longhorned beetle Pheromone chemistry Phenotypic plasticity Local adaptation 



A special thank you to Araci R. and Cassio D. Silva for their invaluable help in field bioassays and to Antonio Santos-Silva (Museu de Zoologia da Universidade de São Paulo) for identifying the cerambycid beetle species. We gratefully acknowledge financial support from Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP, grant #2013/26923-2) to WDS, USDA-APHIS (grant #15-8130-1422-CA) to JGM and LMH, and the Alphawood Foundation to LMH. This work also was supported by INCT-Semioquímicos na Agricultura (FAPESP and CNPq - grants #2014/50871-0 and #465511/2014-7, respectively). Field collections of the cerambycid beetles were conducted under the SISBIO permit n° #46395-2 from the Brazilian Ministry of the Environment.

Supplementary material

10886_2018_1024_MOESM1_ESM.pdf (4.6 mb)
ESM 1 Supplementary online information includes the details of the synthesis of (Z)-7-hexadecene, mass spectra of the epoxidized (Z)-7-hexadecene from the insect extracts and from an authentic standard, gas chromatograms of the epoxidized insect extract and the epoxidized authentic standard of (Z)-7-hexadecene, the mass spectrum of the epoxide of the trace amount of (E)-7-hexadecene present in the (Z)-7-hexadecene standard, the mass spectrum of the epoxide of the tentatively identified (Z)-6-pentadecene present as a minor component in the extracts from male beetles of the Valentim Gentil population, and photographs of male beetles from the two populations. (PDF 4752 kb)


  1. Agrawal AA (2001) Phenotypic plasticity in the interactions and evolution of species. Science 294:321–326. CrossRefPubMedGoogle Scholar
  2. Cardé RT (2014) Defining attraction and aggregation pheromones: teleological versus functional perspectives. J Chem Ecol 40:519–520. CrossRefPubMedGoogle Scholar
  3. Hanks LM, Millar JG (2016) Sex and aggregation-sex pheromones of cerambycid beetles: basic science and practical applications. J Chem Ecol 42:631–654. CrossRefPubMedGoogle Scholar
  4. Linsley EG (1959) Ecology of Cerambycidae. Annu Rev Entomol 4:99–138. CrossRefGoogle Scholar
  5. Martins UR (1999) Tribo Eburiini Blanchard, 1845. In: Martins UR (ed) Cerambycidae Sul-Americanos (Coleoptera): taxonomia, vol 3. Sociedade Brasileira de Entomologia, São Paulo, pp 119–391 (in Portuguese)Google Scholar
  6. McDonald JH (2014) Handbook of biological statistics, 3rd edn. Sparky House Publishing, BaltimoreGoogle Scholar
  7. Millar JG, Hanks LM (2017) Chemical ecology of cerambycids. In: Wang Q (ed) Cerambycidae of the world: biology and pest management. CRC Press. Taylor & Francis, Boca Raton, pp 167–202Google Scholar
  8. Monné MA (2018) Catalogue of the Cerambycidae (Coleoptera) of the Neotropical region. Part I: subfamily Cerambycinae Accessed 24 July 2018
  9. Newcombe RG (1998) Two-sided confidence intervals for the single proportion: comparison of seven methods. Stat Med 17:857–872.<857::AID-SIM777>3.0.CO;2-E CrossRefPubMedGoogle Scholar
  10. SAS Institute (2011) SAS/STAT 9.3 user’s guide. SAS Institute Inc., CaryGoogle Scholar
  11. Silva WD, Millar JG, Hanks LM, Bento JMS (2016) 10-Methyldodecanal, a novel attractant pheromone produced by males of the south American cerambycid beetle Eburodacrys vittata. PLoS One 11:e0160727. CrossRefPubMedPubMedCentralGoogle Scholar
  12. Sokal RR, Rohlf FJ (1995) Biometry, 3rd edn. W. H. Freeman, New YorkGoogle Scholar
  13. Tippmann FF (1960) Studien über neotropische longicornier III. Koleopterologische Rundschau 37-38:82–217 (in German)Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Entomology and AcarologyUniversity of São PauloPiracicabaBrazil
  2. 2.Department of EntomologyUniversity of Illinois at Urbana-ChampaignUrbanaUSA
  3. 3.Departments of Entomology and ChemistryUniversity of CaliforniaRiversideUSA

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