Chemoecology

, Volume 24, Issue 1, pp 35–39 | Cite as

Stereochemistry affects sesquiterpene lactone bioactivity against an herbivorous grasshopper

Short Communication

Abstract

Sesquiterpene lactones are defensive compounds which protect plants against a variety of herbivores and other natural enemies. Sesquiterpene lactones from higher plants can be divided into two groups based on the stereochemistry of their lactone ring junction, either cis-fused or trans-fused. It is unclear whether and how this variation affects potentially important ecological interactions. To investigate whether stereochemical variation in sesquiterpene lactone ring junctions can influence resistance to herbivorous insects, we performed controlled feeding trials with two pairs of diastereomeric sesquiterpene lactones and examined the deterrent effect of each compound on feeding by the polyphagous grasshopper Schistocerca americana (Drury). Sesquiterpene lactone stereochemistry and concentration significantly influenced feeding behavior with grasshoppers consuming less of the trans-fused compounds than the cis-fused compounds. To our knowledge, this is the first demonstration that sesquiterpene lactone ring junction stereochemistry influences the feeding behavior of herbivores. Because this stereochemical trait polymorphism is widely distributed in nature, it could have substantial consequences for the ecology and evolution of large groups of plants, particularly the Asteraceae.

Keywords

Xanthium strumarium Isomer Herbivory Secondary metabolite Plant defense Feeding trial 

Supplementary material

49_2013_144_MOESM1_ESM.pdf (258 kb)
Supplementary material 1 (PDF 259 kb)

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Copyright information

© Springer Basel 2013

Authors and Affiliations

  1. 1.Laboratory of Organic Chemistry and Chemical Biology, Department of ChemistryUniversity of TurkuTurkuFinland
  2. 2.Department of BiologyUniversity of New MexicoAlbuquerqueUSA
  3. 3.Department of Ecology and Evolutionary BiologyRice UniversityHoustonUSA

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