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Chemical Senses Advance Access published online on June 15, 2006
Chemical Senses, doi:10.1093/chemse/bjl001
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Published by Oxford University Press 2006.
Accepted May 17, 2006

Article

Olfactory Discrimination among Sex Pheromone Stereoisomers: Chirality Recognition by Pink Hibiscus Mealybug Males

Aijun Zhang 1 *, Shifa Wang 2, Justin Vitullo 3, Amy Roda 4, Catharine Mannion 5, and J. Christopher Bergh 6

1 Chemicals Affecting Insect Behavior Laboratory, Beltsville Agriculture Research Center-West, US Department of Agriculture (USDA), Agriculture Research Service, Beltsville, MD 20705, USA
2 Department of Entomology, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061, USA; College of Chemical Engineering, Nanjing Forestry University, Long Pan Road, Nanjing, Jiangsu 210037, People's Republic of China
3 Department of Entomology, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061, USA
4 Plant Protection and Quarantine, Center for Plant Health Science and Technology, USDA, Animal and Plant Health Inspection Service, Miami, FL 33158, USA
5 Department of Entomology, University of Florida, Tropical Research and Education Center, Homestead, FL 33031, USA
6 Alson H. Smith, Jr Agricultural Research and Extension Center, Virginia Polytechnic Institute and State University, Winchester, VA 22602, USA

* To whom correspondence should be addressed.
Aijun Zhang, E-mail: zhanga{at}ba.ars.usda.gov


  Abstract

Our previous field studies suggested that the two chiral centers in the sex pheromone of pink hibiscus mealybug, Maconellicoccus hirsutus, could elicit different male responses. The chiral center in the acid moiety of the pheromone seemed to be more critical than the alcohol portion of the pheromone molecule for attractiveness. The objective of the current study was to test this hypothesis by deploying stereoisomeric blends in pheromone traps. Captures of male M. hirsutus showed that pheromone with the naturally occurring (R)-maconelliyl (S)-2-methylbutanoate and (R)-lavandulyl (S)-2-methylbutanoate [R-S configuration] was most attractive and that pheromone with the unnatural S-S configuration was less attractive. In addition, the RS-R blend (containing R-R and S-R stereoisomers) yielded captures of male M. hirsutus that were comparable to blank controls, and an inhibitory effect was observed when R-R and S-R were combined with naturally occurring R-S blend. These results suggest a unique chirality recognition mechanism; olfactory discrimination among different pheromone stereoisomers depends upon both asymmetric centers. The S configuration on the acid moiety elicits attraction, whereas the R configuration induces inhibition. However, the attractive activity shows some degree of tolerance toward chirality change in the alcohol portion of the pheromone molecules.

Keywords: antagonistic effect; chirality recognition; pink hibiscus mealybug; sex pheromone; stereoisomer.
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