The Relationship between Structurally Different Pyrrolizidine Alkaloids and Western Flower Thrips Resistance in F 2 Hybrids of Jacobaea vulgaris and Jacobaea aquatica

Journal of Chemical Ecology

Volumn 37, Issue 10, 2011, Pages 1071-1080

  Cheng, Dandan ^a,b   Kirk, Heather ^a,c   Vrieling, Klaas ^a   Mulder, Patrick P J ^d   Klinkhamer, Peter G L ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b CHINA UNIVERSITY OF GEOSCIENCES   (China)

^c TRENT UNIVERSITY   (Canada)

^d WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Chemical defense; Frankliniella occidentalis; Hybridization; Jacobaea aquatica; Jacobaea vulgaris; Secondary metabolite diversity

Indexed keywords

PYRROLIZIDINE ALKALOID;

ADAPTIVE RADIATION; ALKALOID; CHEMICAL DEFENSE; CONCENTRATION (COMPOSITION); GENE EXPRESSION; GENOTYPE; HERB; HYBRID; HYBRIDIZATION; MOLECULAR ANALYSIS; OXIDE; PEST RESISTANCE; PLANT DEFENSE; PLANT-HERBIVORE INTERACTION; REGRESSION ANALYSIS; SECONDARY METABOLITE; THRIPS;

ARTICLE; CHEMISTRY; CHIMERA; FLOWER; GENETICS; GENOTYPE; HERBIVORY; HOST PARASITE INTERACTION; METABOLISM; PARASITOLOGY; PHYSIOLOGY; SENECIO; THYSANOPTERA;

CHIMERA; FLOWERS; GENOTYPE; HERBIVORY; HOST-PARASITE INTERACTIONS; PYRROLIZIDINE ALKALOIDS; SENECIO; THYSANOPTERA;

FRANKLINIELLA OCCIDENTALIS; HEXAPODA;

EID: 80255133229     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-011-0021-6     Document Type: Article

References (44)

1. Abbott, R. J., Ritchie, M. G., and Hollingsworth, P. M. 2008. Speciation in plants and animals: pattern and process-Introduction. Phil. Trans. R. Soc. Lond. B. 363: 2965-2969.
2. Barton, N. H. 2001. The role of hybridization in evolution. Mol. Ecol. 10: 551-568.
3. Cheng, D., Kirk, H., Mulder, P. P. J., Vrieling, K., and Klinkhamer, P. G. L. 2011. Pyrrolizidine alkaloid variation in shoots and roots of segregating hybrids between Jacobaea vulgaris and Jacobaea aquatica. New Phytol. doi: 10. 1111/j. 1469-8137. 2011. 03841. x.
4. Chou, M. W., Wang, Y. P., Yan, J., Yang, Y. C., Beger, R. D., Williams, L. D., Doerge, D. R., and Fu, P. P. 2003. Riddelliine N-oxide is a phytochemical and mammalian metabolite with genotoxic activity that is comparable to the parent pyrrolizidine alkaloid riddelliine. Toxicology Letters. 145: 239-247.
5. Christie, S. M. H., Kropman, M., Leisegang, E. C., and Warren, F. L. 1949. The senecio alkaloids. Part III. The structure of retrorsine and isatidine, and the isomerism of retronecic acid and isatinecic acid. J. Chem. Soc. 1700-1702.
6. Crawley, M. J. 2005. Statistics: An Introduction Using R. John Wiley & Sons, Ltd., Longdon.
7. Dominguez, D. M., Reina, M., Santos-Guerra, A., Santana, O., Agullo, T., Lopez-Balboa, C., and Gonzalez-Coloma, A. 2008. Pyrrolizidine alkaloids from Canarian endemic plants and their biological effects. Biochem. Syst. Ecol. 36: 153-166.
8. Fritz, R. S. 1999. Resistance of hybrid plants to herbivores: genes, environment, or both? Ecology 80: 382-391.
9. Hallgren, P., Ikonen, A., Hjalten, J., and Roininen, H. 2003. Inheritance patterns of phenolics in F1, F2, and back-cross hybrids of willows: implications for herbivore responses to hybrid plants. J. Chem. Ecol. 29: 1143-1158.
10. Hartmann, T. 1999. Chemical ecology of pyrrolizidine alkaloids. Planta. 207: 483-495.
11. Hartmann, T. and Toppel, G. 1987. Senecionine N-oxide, the primary product of pyrrolizidine alkaloid biosynthesis in root cultures of Senecio vulgaris. Phytochemistry 26: 1639-1643.
12. Hartmann, T. and Witte, L. 1995. Pyrrolizidine alkaloids: Chemical, biological and chemoecological aspects, pp. 155-233, in S. W. Pelletier (eds.), Alkaloids: Chemical and Biological Perspectives, vol. 9. Pergamon Press, Oxford, UK.
13. Hartmann, T., Ehmke, A., Eilert, U., Von Borstel, K., and Theuring, C. 1989. Sites of synthesis, translocation and accumulation of pyrrolizidine alkaloid N-oxides in Senecio vulgaris L. Planta 177: 98-107.
14. He, Y.-Q., Yang, L., Liu, H. X., Zhang, J.-W., Liu, Y., Fong, A., Xiong, A.-Z., Lu, Y.-L., Yang, L., Wang, C.-H., and Wang, Z.-T. 2010. Glucuronidation, a new metabolic pathway for pyrrolizidine alkaloids. Chem. Res. Toxicol. 23: 591-599.
15. Hochwender, C. G., Fritz, R. S., and Orians, C. M. 2000. Using hybrid systems to explore the evolution of tolerance to damage. Evol. Ecol. 14: 509-521.
16. Joosten, L., Mulder, P. P. J., Vrieling, K., van Veen, J. A. V., and Klinkhamer, P. G. L. 2010. The analysis of pyrrolizidine alkaloids in Jacobaea vulgaris; a comparison of extraction and detection methods. Phytochem. Anal. 21: 197-204.
17. Joosten, L., Cheng, D., Mulder, P. P. J., Vrieling, K., van Veen, J. A. V., and Klinkhamer, P. G. L. 2011. The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in Jacobaea vulgaris. Phytochemistry 70: 214-222.
18. Kirk, W. D. J., and Terry, L. I. 2003. The spread of the western flower thrips Frankliniella occidentalis (Pergande). Agric. For. Entomol. 5: 301-310.
19. Kirk, H., Macel, M., Klinkhamer, P. G. L., and Vrieling, K. 2004. Natural hybridization between Senecio jacobaea and Senecio aquaticus: molecular and chemical evidence. Mol. Ecol. 13: 2267-2274.
20. Kirk, H., Vrieling, K., and Klinkhamer, P. G. L. 2005. Reproductive fitness of hybrids between Senecio jacobaea and S. aquaticus (Asteraceae). Am. J. Bot. 92: 1467-1473.
21. Kirk, H., Cheng, D., Choi, Y. H., Vrieling, K., and Klinkhamer, P. G. L. 2011. Transgressive segregation of primary and secondary metabolites in F2 hybrids between Jacobaea aquatica and J. vulgaris. Metabolomics doi: 10. 1007/s11306-011-0301-8.
22. Langel, D. Ober, D. and Pelser, P. B. 2011. The evolution of pyrrolizidine alkaloid biosynthesis and diversity in the Senecioneae. Phytochem. Rev. 10: 3-74.
23. Leiss, K. A., Choi, Y. H., Abdel-Farid, I. B., Verpoorte, R., and Klinkhamer, P. G. L. 2009. NMR metabolomics of thrips (Frankliniella occidentalis) resistance in Senecio hybrids. J. Chem. Ecol. 35: 219-229.
24. Lexer, C., Randell, R. A., and Rieseberg, L. H. 2003. Experimental hybridization as a tool for studying selection in the wild. Ecology 84: 1688-1699.
25. Logie, C. G., Grue, M. R., and Liddell, J. R. 1994. Proton NMR speectroscopy of pyrrolizidine alkaloids. Phytochemistry, 37: 43-109.
26. 48.Macel, M. 2003. On the evolution of the diversity of pyrrolizidine alkaloids: The role of insects as selective forces. PhD Dissertation. University of Leiden.
27. Macel, M. 2011. Attract and deter: a dual role for pyrrolizidine alkaloids in plant-insect interactions. Phytochem. Rev. 1-8.
28. Macel, M., Bruinsma, M., Dijkstra, S. M., Ooijendijk, T., Niemeyer, H. M., and Klinkhamer, P. G. L. 2005. Differences in effects of pyrrolizidine alkaloids on five generalist insect herbivore species. J. Chem. Ecol. 31: 1493-1508.
29. Orians, C. M. 2000. The effects of hybridization in plants on secondary chemistry: implications for the ecology and evolution of plant-herbivore interactions. Am. J. Bot. 87: 1749-1756.
30. Orians, C. M., Hochwender, C. G., Fritz, R. S., and Snall, T. 2010. Growth and chemical defense in willow seedlings: trade-offs are transient. Oecologia 163: 283-290.
31. Pelser, P. B., Gravendeel, B., and van Der Meijden, R. 2003. Phylogeny reconstruction in the gap between too little and too much divergence: the closest relatives of Senecio jacobaea (Asteraceae) according to DNA sequences and AFLPs. Mol. Phylogenet. Evol. 29: 613-628.
32. Pelser, P. B., De Vos, H., Theuring, C., Beuerle, T., Vrieling, K., and Hartmann, T. 2005. Frequent gain and loss of pyrrolizidine alkaloids in the evolution of Senecio section Jacobaea (Asteraceae). Phytochemistry 66: 1285-1295.
33. R DEVELOPMENT CORE TEAM. 2009. R: A language and environment for statistical computing. R Foundation for Statistical Computing, Vienna, Austria. URL http://www.R-project.org.
34. Rieseberg, L. H. and Ellstrand, N. C. 1993. What can molecular and morphological markers tell us about plant hybridization. Crit. Rev. Plant Sci. 12: 213-241.
35. Rizk, A. M. 1991. Naturally Occurring Pyrrolizidine Alkaloids. Boca Raton, Florida, USA: CRC Press. 240 p.
36. Seehausen, O. 2004. Hybridization and adaptive radiation. Trends Ecol. Evol. 19: 198-207.
37. Thoden, T. C., Boppre, M., and Hallmann, J. 2009. Effects of pyrrolizidine alkaloids on the performance of plant-parasitic and free-living nematodes. Pest Manage. Sci. 65: 823-830.
38. van Dam, N. M., van Der Meijden, E., and Verpoorte, R. 1993. Induced responses in 3 alkaloid-containing plant-species. Oecologia. 95: 425-430.
39. van Dam, N. M., Vuister, L. W. M., Bergshoeff, C., De Vos, H., and van Der Meijden, E. D. 1995. The 'raison d'etre' of pyrrolizidine alkaloids in Cynoglossum officinale deterrent effects against generalist herbivores. J. Chem. Ecol. 21: 507-523.
40. Vincent, P. L. D. 1996. Progress on clarifying the generic concept of Senecio based on an extensive world-wide sample of taxa, pp. 597-611 in: D. Hind, H. Beentje (eds.), Compositae: Systematics. Proceedings of the International Compositae Conference. Royal Botanic Gardens, Kew.
41. Vrieling, K., and Bruin, J. 1987. Induction of pyrrolizidine alkaloids after artificial damage of rosette-plants of Senecio jacobaea L. Rijksuniversiteit Faculteit Landbouwwetenschappen Gent. 52: 1321-1326.
42. Vrieling, K., De Vos, H., and van Wijk, C. A. M. 1993. Genetic analysis of the concentrations of pyrrolizidine alkaloids in Senecio Jacobaea. Phytochemistry 32: 1141-1144.
43. Wiedenfeld, H., Roeder, E., Bourauel, T., and Edgar, J. 2008. Pyrrolizidine Alkaloids: Structure and Toxicity. V& R unipress GmbH, Bonn.
44. Yudin, L. S., Cho, J. J., and Mitchell, W. C. 1986. Host range of western flower thrips, Frankliniella occidentalis (Thysanoptera, Thripidae), with special reference to Leucaena glauca. Environ. Entomol. 15: 1292-1295.