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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. Silva
  • José Maurício S. Bento
  • Lawrence M. Hanks
  • Jocelyn G. Millar
Rapid Communication

Abstract

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.

Keywords

Semiochemical Longhorned beetle Pheromone chemistry Phenotypic plasticity Local adaptation 

Notes

Acknowledgements

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)

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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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