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

Stereochemistry affects sesquiterpene lactone bioactivity against an herbivorous grasshopper

Short Communication


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.


Xanthium strumarium Isomer Herbivory Secondary metabolite Plant defense Feeding trial 



For invaluable assistance we thank Spencer Behmer, Marion Le Gall, Paul Lenhart, Alexander Zaykov, Jorge Fallas, Ron Parry, Steve Hovick and Evan Siemann. Funding was provided by a Wray-Todd Fellowship, Sigma Xi GIAR, NSF DEB 0716868 and NSF DEB 1011661.

Supplementary material

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


  1. Ahern JR, Whitney KD (in press) Sesquiterpene lactone stereochemistry influences herbivore resistance and plant fitness. Ann BotGoogle Scholar
  2. Boswell AW, Provin T, Behmer ST (2008) The relationship between body mass and elemental composition in nymphs of the grasshopper Schistocerca americana. J Orthoptera Res 17:307–313Google Scholar
  3. Budesínský M, Saman D (1995) Carbon-13 NMR spectra of sesquiterpene lactones. Annual reports on NMR spectroscopy, vol 30. Academic Press, London, pp 231–475Google Scholar
  4. Harborne JB, Baxter H, Moss GP (1999) Phytochemical dictionary: a handbook of bioactive compounds from plants, 2nd edn. Taylor and Francis, LondonGoogle Scholar
  5. Harwood LM (1985) “Dry-column” flash chromatography. Aldrichimica Acta 18:25Google Scholar
  6. Kalsi PS (2009) Stereochemistry conformation and mechanism, 7th edn. Anshan Ltd., KentGoogle Scholar
  7. Krogsgaard-Larsen P (1998) GABA synaptic mechanisms: stereochemical and conformational requirements. Med Res Rev 8(1):27–56CrossRefGoogle Scholar
  8. Mullin CA, Mason CH, Chou JC, Linderman JR (1992) Phytochemical antagonism of γ-aminobutyric acid based resistances in Diabrotica. In: Mullin CA, Scott JG (eds) Molecular mechanisms of insecticide resistance: diversity among insects. ACS symposium series no. 505. American Chemical Society, Washington, DC, pp 288–308CrossRefGoogle Scholar
  9. Mullin CA, Chyb S, Eichenseer H, Hollister B, Frazier JL (1994) Neuroreceptor mechanisms in insect gustation: a pharmacological approach. J Insect Physiol 40(11):913–931CrossRefGoogle Scholar
  10. Otte D (1975) Plant preference and plant succession. A consideration of evolution of plant preference in Schistocerca. Oecologia 18(2):129–144Google Scholar
  11. Passreiter CM, Isman MD (1997) Antifeedant bioactivity of sesquiterpene lactones from Neurolaena lobata and their antagonism by gamma-aminobutyric acid. Biochem Syst Ecol 25(5):371–377CrossRefGoogle Scholar
  12. Picman AK (1986) Biological-activities of sesquiterpene lactones. Biochem Syst Ecol 14:255–281CrossRefGoogle Scholar
  13. Rodriguez E, Towers GHN, Mitchell JC (1976) Biological activities of sesquiterpene lactones. Phytochemistry 15:1573–1580CrossRefGoogle Scholar
  14. SAS Institute (2010) The SAS system for Windows, Version 9.3. SAS Institute, CaryGoogle Scholar
  15. Schmidt TJ (1999) Toxic activities of sesquiterpene lactones: structural and biochemical aspects. Curr Org Chem 3:577–608Google Scholar
  16. Schmidt TJ (2006) Structure-activity relationships of sesquiterpene lactones. In: Rahman A (ed) Studies in natural products chemistry: Bioactive natural products, (Part M), vol 33. Elsevier, Amsterdam, pp 309–392Google Scholar
  17. Seaman FC (1982) Sesquiterpene lactones as taxonomic characters in the Asteraceae. Bot Rev 48:121–594CrossRefGoogle Scholar
  18. Testa B, Vistoli G, Pedretti A, Caldwell J (2013) Organic stereochemistry. Part 5. Stereoselectivity in molecular and clinical pharmacology. Helvetica Chimica Acta 96(5):747–798CrossRefGoogle Scholar
  19. Yoshioka H, Mabry TJ, Timmermann BN (1973) Sesquiterpene lactones: chemistry, NMR and plant distribution. The University of Tokyo Press, TokyoGoogle Scholar

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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