Journal of Chemical Ecology

, Volume 45, Issue 5–6, pp 464–473 | Cite as

Subtle Chemical Variations with Strong Ecological Significance: Stereoselective Responses of Male Orchid Bees to Stereoisomers of Carvone Epoxide

  • Katharina Brandt
  • Stefan Dötterl
  • Roman Fuchs
  • Daniela Maria do Amaral Ferraz Navarro
  • Isabel Cristina Sobreira Machado
  • Daniel Dobler
  • Oliver Reiser
  • Manfred Ayasse
  • Paulo Milet-PinheiroEmail author


Different enantiomers of chiral compounds within floral perfumes usually trigger distinct responses in insects; however, this has frequently been neglected in studies investigating semiochemicals in plant-pollinator interactions. Approximately 1000 neotropical plants produce floral perfumes as the only reward for pollinators, i.e. male euglossine bees. The chiral compound carvone epoxide is a key component of the scent bouquet of many perfume-rewarding plants that are pollinated by males of Eulaema. Here, we tested the biological activity of the four carvone epoxide stereoisomers to four Eulaema species occurring in the Atlantic Rainforest of NE-Brazil. We determined the stereochemistry of carvone epoxide in the floral scent of several Catasetum species, tested whether the antennae of bees respond differentially to these stereoisomers and investigated if there is a behavioural preference for any of the stereoisomers. We found that 1) Catasetum species emit only the (−)-trans-stereoisomer of carvone epoxide, 2) for E. atleticana and E. niveofasciata antennal responses to the (−)-trans-carvone epoxide were significantly stronger than those to (−)-cis-carvone epoxide, 3) the strength and pattern of antennal responses to all 4 stereoisomers (separately tested) did not differ among Eulaema species, and 4) there were significant differences in attractiveness of the four stereoisomers to the bees species with the (−)-trans-stereoisomer being particularly attractive. We assume (−)-trans-carvone epoxide to be the dominant isomer in perfume-rewarding plants pollinated by Eulaema. The universal occurrence of carvone epoxide in Catasetum species pollinated by Eulaema, suggests that this compound has evolved in perfume-rewarding as a specific attractant for Eulaema bees as pollinators.


Catasetum Chirality Electrophysiology Eulaema Euglossine bees Perfume-rewarding plants Pollinators 



We thank Tiago César and Juan Fernández Gómez for providing Catasetum plants for sampling of floral perfumes and Hans Saegesser Santos for performing preliminary EAG analyses. This work was supported by the Deutsche Forschungsgemeinschaft (AY 12/12-1), the Deutscher Akademischer Austauschdienst (DAAD grant number 57210526), Coordenação de Aperfeiçoamento de Nível Superior (CAPES, Brazil - Finance Code 001 - grant to P.M.P.), Fundação de Amparo à Ciência e Tecnologia do Estado de Pernambuco (grant number FACEPE/BCT - 0288-2.05/17 to P.M.P.), and Conselho Nacional de Desenvolvimento Científico e Tecnológico (grant number CNPq/PDJ -152077/2016-2 to P.M.P).

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Copyright information

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

Authors and Affiliations

  • Katharina Brandt
    • 1
  • Stefan Dötterl
    • 2
  • Roman Fuchs
    • 2
  • Daniela Maria do Amaral Ferraz Navarro
    • 3
  • Isabel Cristina Sobreira Machado
    • 4
  • Daniel Dobler
    • 5
  • Oliver Reiser
    • 5
  • Manfred Ayasse
    • 1
  • Paulo Milet-Pinheiro
    • 4
    Email author
  1. 1.Institute of Evolutionary Ecology and Conservation GenomicsUniversity of UlmUlmGermany
  2. 2.Department of BiosciencesUniversity of SalzburgSalzburgAustria
  3. 3.Departamento de Química FundamentalUniversidade Federal de PernambucoRecifeBrazil
  4. 4.Departamento de BotânicaUniversidade Federal de PernambucoRecifeBrazil
  5. 5.Institute of Organic ChemistryUniversity of RegensburgRegensburgGermany

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