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Journal of Chemical Ecology

, Volume 38, Issue 7, pp 836–845 | Cite as

Sex Pheromone Communication in Two Sympatric Neotropical Stink Bug Species Chinavia ubica and Chinavia impicticornis

  • M. C. Blassioli-Moraes
  • R. A. Laumann
  • M. W. M. Oliveira
  • C. M. Woodcock
  • P. Mayon
  • A. Hooper
  • J. A. Pickett
  • M. A. Birkett
  • M. Borges
Article

Abstract

Chinavia and Nezara spp. stink bugs (Heteroptera: Pentatomidae) include over100 species, with highest diversity in Afrotropical and Neotropical regions. Species thus far studied in these genera utilize trans-(Z)-(4 S)-bisabolene epoxide (BE) and cis-(Z)-(4 S)-BE as major sex pheromone components, with species specificity ensured by different ratios of the two compounds. Gas chromatography (GC) and coupled GC-mass spectrometry (GC-MS) analyses of a volatiles from C. ubica males revealed the presence of two BE isomers in approximately a 90:10 ratio, which were shown by microprobe 1 H NMR to be cis-(Z)-BE and trans-(Z)-BE isomers, respectively. Analyses of volatiles from C. impicticornis males suggested the presence of a single isomer, trans-(Z)-BE, in high purity (>90 %). The absolute configurations of the isomers produced by C. ubica and C. impicticornis were determined using chiral GC analysis (β-DEX column). Oxidative microchemistry of synthetic standards of cis-(Z)-(4 S)-BE and trans-(Z)-(4R)-BE, and volatiles from male of C. ubica, revealed the absolute stereochemistry of the cis-(Z)-BE to be (1R,2 S,4 S) [cis-(Z)-(4 S) for short]. Similarly, analyses of trans-(Z)-(4 S)-BE and cis-(Z)-(4R)-BE standards, and volatiles from males of C. ubica and C. impicticornis, revealed the absolute stereochemistry of the trans-(Z)-BE to be (1 S,2R,4 S) [trans-(Z)-(4 S) for short]. Olfactometer bioassays with synthetic BEs confirmed attraction of female C. ubica and C. impicticornis to conspecific synthetic pheromone, but not to heterospecific synthetic pheromone. Chinavia impicticornis appeared not to discriminate behaviorally between the conspecific pheromone and its enantiomer. Coupled GC-electroantennography with antennae from females suggested that C. ubica and C. impicticornis possess olfactory receptors for both cis-(Z)-(4 S)-BE and trans-(Z)-(4 S)-BE. The results in this study confirm that C. ubica and C. impicticornis, as for other Chinavia and Nezara spp., utilize cis-(Z)-(4 S)-BE and trans-(Z)-(4 S)-BE as sex pheromone components, with different ratios guaranteeing species specificity. Furthermore, the results suggest that the absolute stereochemistry of BEs may be less important for conspecific recognition than the relative stereochemistry between the epoxide group and the alkyl substituent on the bisabolene ring.

Keywords

Soybean pest Sex pheromone Bisabolene epoxide Olfactometer bioassay Heteroptera Pentatomidae 

Notes

Acknowledgements

We thank Hélio Moreira for rearing the insects. This work was funded by International Foundation for Science (IFS), National Council for Scientific and Technological Development (CNPq), Distrito Federal Research Foundation, and Brazilian Agricultural Research Corporation (Embrapa). Rothamsted Research receives grant-aided support from the Biotechnology and Biological Sciences Research Council (BBSRC) of the United Kingdom.

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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • M. C. Blassioli-Moraes
    • 1
  • R. A. Laumann
    • 1
  • M. W. M. Oliveira
    • 1
  • C. M. Woodcock
    • 2
  • P. Mayon
    • 2
  • A. Hooper
    • 2
  • J. A. Pickett
    • 2
  • M. A. Birkett
    • 2
  • M. Borges
    • 1
  1. 1.Embrapa Genetic Resources and BiotechnologyBrasília-DFBrazil
  2. 2.Biological Chemistry DivisionRothamsted ResearchHarpendenUK

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