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Journal of Chemical Ecology

, Volume 46, Issue 1, pp 1–9 | Cite as

Male-Produced Sex Pheromone of Tibraca limbativentris Revisited: Absolute Configurations of Zingiberenol Stereoisomers and their Influence on Chemotaxis Behavior of Conspecific Females

  • M. C. Blassioli-Moraes
  • A. Khrimian
  • M. F. F. Michereff
  • D. M. Magalhães
  • E. Hickel
  • T. F. S. de Freitas
  • J. A. F. Barrigossi
  • R. A. Laumann
  • A. T. Silva
  • S. D. Guggilapu
  • C. C. Silva
  • J. Sant’Ana
  • M. BorgesEmail author
Article
  • 48 Downloads

Abstract

The rice stalk stink bug, Tibraca limbativentris, is an important rice pest in Brazil with a high invasive potential for Mexico and the USA. The sex pheromone of this species was previously identified as a combination of two stereoisomers of 1,10-bisaboladien-3-ol (zingiberenol), but the absolute configurations of these sesquiterpenes were not determined, neither were their effect(s) on T. limbativentris behavior evaluated. In this study, using two chiral columns, we compared retention times of the two natural 1,10-bisaboladien-3-ol stereoisomers from air-entrainment samples of male T. limbativentris with those of synthetic stereoisomers of 1,10-bisaboladien-3-ol. The results showed that T. limbativentris males produce (3S,6S,7R)-1,10-bisaboladien-3-ol (1) and (3R,6S,7R)-1,10-bisaboladien-3-ol (5) as their sex pheromone. Two new minor, male-specific components were also identified as cis and trans isomers of 2,10-bisaboladien-1-ol (sesquipiperitol). Y-tube olfactometer bioassays showed that the major (3S,6S,7R) isomer 1 was essential for attraction of T. limbativentris females, but the minor (3R,6S,7R) isomer 2 was not, nor did it show synergistic/antagonistic effects when added to the major isomer. The (1S,6S,7R) and (1R,6S,7R) stereoisomers of sesquipepiritol also attracted T. limbativentris females.

Keywords

Rice pest Stink bug behavior Attractants 

Notes

Acknowledgements

This work received financial support from the National Council of Technological and Scientific Development (CNPq), Federal District Research Foundation (FAP-DF) and the Brazilian Corporation of Agricultural Research (EMBRAPA). We state that our work conforms to the legal requirements for animal welfare in Brazil.

Supplementary material

10886_2019_1125_MOESM1_ESM.docx (144 kb)
ESM 1 (DOCX 144 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • M. C. Blassioli-Moraes
    • 1
  • A. Khrimian
    • 2
  • M. F. F. Michereff
    • 1
  • D. M. Magalhães
    • 1
  • E. Hickel
    • 3
  • T. F. S. de Freitas
    • 4
  • J. A. F. Barrigossi
    • 5
  • R. A. Laumann
    • 1
  • A. T. Silva
    • 1
    • 6
  • S. D. Guggilapu
    • 7
  • C. C. Silva
    • 1
  • J. Sant’Ana
    • 4
  • M. Borges
    • 1
    Email author
  1. 1.Laboratório de Semioquímicos, Embrapa Recursos Genéticos e BiotecnologiaBrasíliaBrazil
  2. 2.Invasive Insect Biocontrol and Behavior LaboratoryUSDA-ARS, NEABeltsvilleUSA
  3. 3.Empresa de Pesquisa Agropecuária e Extensão Rural de Santa Catarina - EPAGRI - Estação Experimental de ItajaíItajaíBrazil
  4. 4.Laboratório de Etologia e Ecologia Química de Insetos, PPG-FitotecniaUniversidade Federal do Rio Grande do Sul (UFRGS)Porto AlegreBrazil
  5. 5.Embrapa Arroz e FeijãoSanto Antônio de GoiásBrazil
  6. 6.Faculdade de Agronomia e Medicina Veterinária (FAV)Campus Darcy Ribeiro, Universidade de BrasiliaBrasíliaBrazil
  7. 7.National Institutes of HealthNational Institute of Diabetes and Digestive and Kidney Diseases, Laboratory of Bioorganic ChemistryBethesdaUSA

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