Stereochemistry affects sesquiterpene lactone bioactivity against an herbivorous grasshopper

Chemoecology

Volumn 24, Issue 1, 2014, Pages 35-39

  Ahern, Jeffrey R ^a,c   Whitney, Kenneth D ^b,c  

^a UNIVERSITY OF TURKU   (Finland)

^b UNIVERSITY OF NEW MEXICO   (United States)

^c RICE UNIVERSITY   (United States)

Author keywords

Feeding trial; Herbivory; Isomer; Plant defense; Secondary metabolite; Xanthium strumarium

Indexed keywords

ASTERACEAE; CAELIFERA; EMBRYOPHYTA; HEXAPODA; SCHISTOCERCA AMERICANA; TRACHEOPHYTA; XANTHIUM STRUMARIUM;

EID: 84892535609     PISSN: 09377409     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00049-013-0144-z     Document Type: Article

References (19)

1. Ahern JR, Whitney KD (in press) Sesquiterpene lactone stereochemistry influences herbivore resistance and plant fitness. Ann Bot.
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: 307-313.
3. Budesínský M, Saman D (1995) Carbon-13 NMR spectra of sesquiterpene lactones. Annual reports on NMR spectroscopy, vol 30. Academic Press, London, pp 231-475.
4. Harborne JB, Baxter H, Moss GP (1999) Phytochemical dictionary: a handbook of bioactive compounds from plants, 2nd edn. Taylor and Francis, London.
5. Harwood LM (1985) "Dry-column" flash chromatography. Aldrichimica Acta 18: 25.
6. Kalsi PS (2009) Stereochemistry conformation and mechanism, 7th edn. Anshan Ltd., Kent.
7. Krogsgaard-Larsen P (1998) GABA synaptic mechanisms: stereochemical and conformational requirements. Med Res Rev 8(1): 27-56.
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 288-308.
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): 913-931.
10. Otte D (1975) Plant preference and plant succession. A consideration of evolution of plant preference in Schistocerca. Oecologia 18(2): 129-144.
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): 371-377.
12. Picman AK (1986) Biological-activities of sesquiterpene lactones. Biochem Syst Ecol 14: 255-281.
13. Rodriguez E, Towers GHN, Mitchell JC (1976) Biological activities of sesquiterpene lactones. Phytochemistry 15: 1573-1580.
14. SAS Institute (2010) The SAS system for Windows, Version 9. 3. SAS Institute, Cary.
15. Schmidt TJ (1999) Toxic activities of sesquiterpene lactones: structural and biochemical aspects. Curr Org Chem 3: 577-608.
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 309-392.
17. Seaman FC (1982) Sesquiterpene lactones as taxonomic characters in the Asteraceae. Bot Rev 48: 121-594.
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): 747-798.
19. Yoshioka H, Mabry TJ, Timmermann BN (1973) Sesquiterpene lactones: chemistry, NMR and plant distribution. The University of Tokyo Press, Tokyo.