UHPLC-ESI/TOFMS Determination of Salicylate-like Phenolic Gycosides in Populus tremula Leaves

Journal of Chemical Ecology

Volumn 37, Issue 8, 2011, Pages 857-870

  Abreu, Ilka Nacif ^a   Ahnlund, Maria ^b   Moritz, Thomas ^b   Albrectsen, Benedicte Riber ^a  

^a UMEÅ UNIVERSITY   (Sweden)

^b SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

Author keywords

Chemotyping; Diversity; Eurasian aspen; Genotype recognition; Natural variation; PG; Salicinoids; Salicylates

Indexed keywords

GLUCOSIDE; PHENOL DERIVATIVE; SALICYLIC ACID DERIVATIVE;

BIOACTIVITY; DECIDUOUS TREE; FORMIC ACID; GENOTYPE; HERBIVORE; IDENTIFICATION METHOD; IONIZATION; LEAF; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHENOLIC COMPOUND; POPULATION STRUCTURE; SPECIES DIVERSITY; ULTRAVIOLET RADIATION;

ARTICLE; ASPEN; CHEMISTRY; ECONOMICS; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; PLANT LEAF; TIME;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCOSIDES; PHENOLS; PLANT LEAVES; POPULUS; SALICYLATES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TIME FACTORS;

POPULUS; POPULUS TREMULA; SALIX;

EID: 79961016024     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-011-9991-7     Document Type: Article

References (42)

1. Albrectsen, B. R., Gutierrez, L., Fritz, R. S., Fritz, R. D., and Orians, C. M. 2007. Does the differential seedling mortality caused by slugs alter the foliar traits and subsequent susceptibility of hybrid willows to a generalist herbivore? Ecol. Entomol. 32: 211-220.
2. Albrectsen, B. R., Witzell, J., Robinson, K. M., Wulff, S., Luquez, V. M. C., Agren, R., and Jansson, S. 2010. Large scale geographic clines of parasite damage to Populus tremula L. Ecography. 33: 483-493.
3. Babst, B. A., Harding, S. A., and Tsai, C. J. 2010. Biosynthesis of phenolic glycosides from phenylpropanoid and benzenoid precursors in Populus. J. Chem. Ecol. 36: 286-297.
4. Boerjan, W., Ralph, J., and Baucher, M. 2003. Lignin biosynthesis. Annu. Rev. Plant. Biol. 54: 519-546.
5. Chen, F., Liu, C. J., Tschaplinski, T. J., and Zhao, N. 2009. Genomics of secondary metabolism in Populus: interactions with biotic and abiotic environments. Crit. Rev. Plant. Sci. 28: 375-392.
6. De Carvalho, D., Ingvarsson, P. K., Joseph, J., Suter, L., Sedivy, C., Macaya-Sanz, D., Cottrell, J., Heinze, B., Schanzer, I., and Lexer, C. 2010. Admixture facilitates adaptation from standing variation in the European aspen (Populus tremula L.), a widespread forest tree. Mol. Ecol. 19: 1638-1650.
7. Dixon, R. A., Xie, D. Y., and Sharma, S. B. 2005. Proanthocyanidins-a final frontier in flavonoid research? New. Phytol. 165: 9-28.
8. Donaldson, J. R., and Lindroth, R. L. 2007. Genetics, environment, and their interaction determine efficacy of chemical defense in trembling aspen. Ecology. 88: 729-739.
9. Greenaway, W., English, S., May, J., and Whatley, F. R. 1991. Chemotaxonomy of section leuce poplars by GC-MS of bud exudate. Biochem. Syst. Ecol. 19: 507-518.
10. Gullberg, J., Jonsson, P., Nordstrom, A., Sjostrom, M., and Moritz, T. 2004. Design of experiments: an efficient strategy to identify factors influencing extraction and derivatization of Arabidopsis thaliana samples in metabolomic studies with gas chromatography/mass spectrometry. Anal. Biochem. 331: 283-295.
11. Harding, S. A., Jarvie, M. M., Lindroth, R. L., and Tsai, C. J. 2009. A comparative analysis of phenylpropanoid metabolism, N utilization, and carbon partitioning in fast- and slow-growing Populus hybrid clones. J. Exp. Bot. 60: 3443-3452.
12. Hemming, J. D. C., and Lindroth, R. L. 1995. Intraspecific variation in aspen phytochemistry-effects on performance of gypsy moths and forest tent caterpillars. Oecologia. 103: 79-88.
13. Hjältén, J., Niemi, L., Wennstrom, A., Ericson, L., Roininen, H., and Julkunen-Tiitto, R. 2007. Variable responses of natural enemies to Salix triandra phenotypes with different secondary chemistry. Oikos. 116: 751-758.
14. Hu, Q. Z., Noll, R. J., Li, H. Y., Makarov, A., Hardman, M., and Cooks, R. G. 2005. The Orbitrap: a new mass spectrometer. J. Mass Spectrom. 40: 430-443.
15. Ingvarsson, P. K. 2005. Nucleotide polymorphism and linkage disequilbrium within and among natural populations of European Aspen (Populus tremula L., Salicaceae). Genetics. 169: 945-953.
16. Jones, C. G., Hopper, R. F., Coleman, J. S., and Krischik, V. A. 1993. Control of systemically induced herbivore resistance by plant vascular architecture. Oecologia. 93: 452-456.
17. Julkunen-Tiitto, R. 1986. A chemotaxonomic survey of phenolics in leaves of northern Salicaceae species. Phytochemistry. 25: 663-667.
18. Kammerer, B., Kahlich, R., Biegert, C., Gleiter, C. H., and Heide, L. 2005. HPLC-MS/MS analysis of willow bark extracts contained in pharmaceutical preparations. Phytochem. Analysis. 16: 470-478.
19. Lindroth, R. L., and Hwang, S.-Y. 1996. Clonal variation in foliar chemistry of quaking aspen (Populus tremuloides Michx.). Biochem. Syst. Ecol. 24.
20. Luquez, V., Hall, D., Albrectsen, B. R., Karlsson, J., Ingvarsson, P., and Jansson, S. 2008. Natural phenological variation in aspen (Populus tremula): the SwAsp collection. Tree Genet. Genomes. 4: 279-292.
21. Makarov, A., Denisov, E., Kholomeev, A., Baischun, W., Lange, O., Strupat, K., and Horning, S. 2006. Performance evaluation of a hybrid linear ion trap/orbitrap mass spectrometer. Anal. Chem. 78: 2113-2120.
22. Morse, A. M., Tschaplinski, T. J., Dervinis, C., Pijut, P. M., Schmelz, E. A., Day, W., and Davis, J. M. 2007. Salicylate and catechol levels are maintained in nahG transgenic poplar. Phytochemistry. 68: 2043-2052.
23. Murashige, T., and Skoog, F. 1962. A revised medium for rapid growth and bio assays with tobacco tissue cultures. Physiol. Plantarum. 15: 473-&.
24. Mutikainen, P., Walls, M., Ovaska, J., Keinanen, M., Julkunen-Tiitto, R., and Vapaavuori, E. 2000. Herbivore resistance in Betula pendula: Effect of fertilization, defoliation, and plant genotype. Ecology. 81: 49-65.
25. Orians, C. M., and Fritz, R. S. 1995. Secondary chemistry of hybrid and parental willows-phenolic glycosides and condensed tannins in Salix sericea, S. eriocephala, and their hybrids. J. Chem. Ecol. 21: 1245-1253.
26. Orians, C. M., and Jones, C. G. 2001. Plants as resource mosaics: a functional model for predicting patterns of within-plant resource heterogeneity to consumers based on vascular architecture and local environmental stability. Oikos 94: 493-504.
27. Orians, C. M., Huang, C. H., Wild, A., Dorfman, K. A., Zee, P., Dao, M. T. T., and Fritz, R. S. 1997. Willow hybridization differentially affects preference and performance of herbivorous beetles. Entomol. Exp. Appl. 83: 285-294.
28. Osier, T. L., and Lindroth, R. L. 2006. Genotype and environment determine allocation to and costs of resistance in quaking aspen. Oecologia. 148: 293-303.
29. Palo, R. T. 1984. Distribution of birch (Betula spp), willow (Salix spp), and poplar (Populus spp) secondary metabolites and their potential role as chemical defense against herbivores. J Chem. Ecol. 10: 499-520.
30. Philippe, R. N., and Bohlman, J. 2007. Poplar defense against insect herbivores. Can. J. Forest Res. 85: 1111-1126.
31. Robinson, A. R., Gheneim, R., Kozak, R. A., Ellis, D. D., and Mansfield, S. D. 2005. The potential of metabolite profiling as a selection tool for genotype discrimination in Populus. J. Exp. Bot. 56: 2807-2819.
32. Robinson, A. R., Ukrainetz, N. K., Kang, K. Y., and Mansfield, S. D. 2007. Metabolite profiling of Douglas fir (Pseudotsuga menziesii) field trials reveals strong environmental and weak genetic variation. New. Phytol. 174: 762-773.
33. Ruuhola, T., and Julkunen-Tiitto, R. 2000. Salicylates of intact Salix myrsinifolia plantlets do not undergo rapid metabolic turnover. Plant Physiology. 122: 895-905.
34. Ruuhola, T., and Julkunen-Tiitto, R. 2003. Trade-off between synthesis of salicylates and growth of micropropagated Salix pentandra. J. Chem. Ecol. 29: 1565-1588.
35. Ruuhola, T., Julkunen-Tiitto, R., and Vainiotalo, P. 2003. In vitro degradation of willow salicylates. J. Chem. Ecol. 29: 1083-1097.
36. Sterky, F., Regan, S., Karlsson, J., Hertzberg, M., Rohde, A., Holmberg, A., Amini, B., Bhalerao, R., Larsson, M., Villarroel, R., et al. 1998. Gene discovery in the wood-forming tissues of poplar: Analysis of 5, 692 expressed sequence tags. Proc. Natl. Acad. Sci. USA. 95: 13330-13335.
37. Tanner, G. J., Francki, K. T., Abrahams, S., Watson, J. M., Larkin, P. J., and Ashton, A. R. 2003. Proanthocyanidin biosynthesis in plants-Purification of legume leucoanthocyanidin reductase and molecular cloning of its cDNA. J. Biol. Chem. 278: 31647-31656.
38. Tsai, C. J., Harding, S. A., Tschaplinski, T. J., Lindroth, R. L., and Yuan, Y. N. 2006. Genome-wide analysis of the structural genes regulating defense phenylpropanoid metabolism in Populus. New. Phytol. 172: 47-62.
39. Warren, J. M., Bassman, J. H., Fellman, J. K., Mattinson, D. S., and Eigenbrode, S. 2003. Ultraviolet-B radiation alters phenolic salicylate and flavonoid composition of Populus trichocarpa leaves. Tree Physiol. 23: 527-535.
40. Wimp, G. M., Wooley, S., Bangert, R. K., Young, W. P., Martinsen, G. D., Keim, P., Rehill, B., Lindroth, R. L., and Whitham, T. G. 2007. Plant genetics predicts intra-annual variation in phytochemistry and arthropod community structure. Mol. Ecol. 16: 5057-5069.
41. Witzell, J., and Martin, J. A. 2008. Phenolic metabolites in the resistance of northern forest trees to pathogens-past experiences and future prospects. Can. J. Forest. Res. 38: 2711-2727.
42. Zapesochnaya, G. G., Kurkin, V. A., Braslavskii, V. B., and Filatova, N. V. 2002. Phenolic compounds of Salix acutifolia bark. Chem. Nat. Compd. 38: 314-318.