title: Sesquiterpene lactone stereochemistry influences herbivore resistance and plant fitness in the field.
abstract: OBJECTIVE
  Stereochemical variation is widely known to influence the bioactivity of compounds in the context of pharmacology and pesticide science, but our understanding of its importance in mediating plant-herbivore interactions is limited, particularly in field settings. Similarly, sesquiterpene lactones are a broadly distributed class of putative defensive compounds, but little is known about their activities in the field.
  
  
  METHODS
  Natural variation in sesquiterpene lactones of the common cocklebur, Xanthium strumarium (Asteraceae), was used in conjunction with a series of common garden experiments to examine relationships between stereochemical variation, herbivore damage and plant fitness.
  
  
  RESULTS
  The stereochemistry of sesquiterpene lactone ring junctions helped to explain variation in plant herbivore resistance. Plants producing cis-fused sesquiterpene lactones experienced significantly higher damage than plants producing trans-fused sesquiterpene lactones. Experiments manipulating herbivore damage above and below ambient levels found that herbivore damage was negatively correlated with plant fitness. This pattern translated into significant fitness differences between chemotypes under ambient levels of herbivore attack, but not when attack was experimentally reduced via pesticide.
  
  
  CONCLUSIONS
  To our knowledge, this work represents only the second study to examine sesquiterpene lactones as defensive compounds in the field, the first to document herbivore-mediated natural selection on sesquiterpene lactone variation and the first to investigate the ecological significance of the stereochemistry of the lactone ring junction. The results indicate that subtle differences in stereochemistry may be a major determinant of the protective role of secondary metabolites and thus of plant fitness. As stereochemical variation is widespread in many groups of secondary metabolites, these findings suggest the possibility of dynamic evolutionary histories within the Asteraceae and other plant families showing extensive stereochemical variation.
authors.affiliation: Laboratory of Organic Chemistry and Chemical Biology, Department of Chemistry, University of Turku, FI-20014 Turku, Finland.
authors.forename: Jeffrey R
authors.initials: JR
authors.lastname: Ahern
authors.forename: Kenneth D
authors.initials: KD
authors.lastname: Whitney
mesh_terms: D000818:Animals; D001517:Coleoptera / Q000187:drug effects*; D060434:Herbivory; D006790:Host-Parasite Interactions; D007783:Lactones / Q000737:chemistry* / Q000378:metabolism; D018515:Plant Leaves / Q000737:chemistry / Q000469:parasitology / Q000502:physiology; D012717:Sesquiterpenes / Q000737:chemistry* / Q000378:metabolism; D031210:Xanthium / Q000737:chemistry* / Q000469:parasitology / Q000502:physiology
chemical_list: D007783:Lactones; D012717:Sesquiterpenes
keywords: Asteraceae; Xanthium strumarium; common cocklebur; common garden; defence; herbivory; plant resistance; plant–insect interactions; sesquiterpene lactone