Table of Contents Author Guidelines Submit a Manuscript
Journal of Analytical Methods in Chemistry
Volume 2015 (2015), Article ID 350259, 10 pages
http://dx.doi.org/10.1155/2015/350259
Research Article

Study of Grape Polyphenols by Liquid Chromatography-High-Resolution Mass Spectrometry (UHPLC/QTOF) and Suspect Screening Analysis

1Consiglio per la Ricerca e la Sperimentazione in Agricoltura, Centro di Ricerca per la Viticoltura (CRA-VIT), Laboratorio Chimico, Viale XXVIII Aprile 26, 31015 Conegliano, Italy
2Istituto di Frutti-Viticoltura, Università Cattolica S.C., Via Emilia Parmense 84, 29122 Piacenza, Italy

Received 17 November 2014; Accepted 7 January 2015

Academic Editor: Antonio Ruiz Medina

Copyright © 2015 Riccardo Flamini et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. Flamini, “Recent applications of mass spectrometry in the study of grape and wine polyphenols,” ISRN Spectroscopy, vol. 2013, Article ID 813563, 45 pages, 2013. View at Publisher · View at Google Scholar
  2. N. Castillo-Muñoz, S. Gómez-Alonso, E. García-Romero, and I. Hermosín-Gutiérrez, “Flavonol profiles of Vitis vinifera red grapes and their single-cultivar wines,” Journal of Agricultural and Food Chemistry, vol. 55, no. 3, pp. 992–1002, 2007. View at Publisher · View at Google Scholar · View at Scopus
  3. N. Castillo-Muñoz, S. Gómez-Alonso, E. García-Romero, M. U. Gómez, H. A. Velders, and I. Hermosín-Gutiérrez, “Flavonol 3-O-glycosides series of Vitis vinifera Cv. Petit Verdot red wine grapes,” Journal of Agricultural and Food Chemistry, vol. 57, no. 1, pp. 209–219, 2009. View at Publisher · View at Google Scholar · View at Scopus
  4. R. Flamini, “Mass spectrometry in grape and wine chemistry. Part I: polyphenols,” Mass Spectrometry Reviews, vol. 22, no. 4, pp. 218–250, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. H. Wang, E. J. Race, and A. J. Shrikhande, “Characterization of anthocyanins in grape juices by ion trap liquid chromatography-mass spectrometry,” Journal of Agricultural and Food Chemistry, vol. 51, no. 7, pp. 1839–1844, 2003. View at Publisher · View at Google Scholar · View at Scopus
  6. M. E. Camire, A. Chaovanalikit, M. P. Dougherty, and J. Briggs, “Blueberry and grape anthocyanins as breakfast cereal colorants,” Journal of Food Science, vol. 67, no. 1, pp. 438–441, 2002. View at Publisher · View at Google Scholar · View at Scopus
  7. J. He and M. Monica Giusti, “Anthocyanins: natural colorants with health-promoting properties,” Annual Review of Food Science and Technology, vol. 1, no. 1, pp. 163–187, 2010. View at Publisher · View at Google Scholar · View at Scopus
  8. V. Hong and R. E. Wrolstad, “Characterization of anthocyanin-containing colorants and fruit juices by HPLC/photodiode array detection,” Journal of Agricultural and Food Chemistry, vol. 38, no. 3, pp. 698–708, 1990. View at Publisher · View at Google Scholar · View at Scopus
  9. M. de Rosso, L. Tonidandel, R. Larcher et al., “Study of anthocyanic profiles of twenty-one hybrid grape varieties by liquid chromatography and precursor-ion mass spectrometry,” Analytica Chimica Acta, vol. 732, pp. 120–129, 2012. View at Publisher · View at Google Scholar · View at Scopus
  10. M. de Rosso, L. Tonidandel, R. Larcher et al., “Identification of new flavonols in hybrid grapes by combined liquid chromatography-mass spectrometry approaches,” Food Chemistry, vol. 163, no. 1, pp. 244–251, 2014. View at Publisher · View at Google Scholar · View at Scopus
  11. X. Vitrac, A. Bornet, R. Vanderlinde et al., “Determination of stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian wines,” Journal of Agricultural and Food Chemistry, vol. 53, no. 14, pp. 5664–5669, 2005. View at Publisher · View at Google Scholar · View at Scopus
  12. L. Bavaresco, E. Cantù, M. Fregoni, and M. Trevisan, “Constitutive stilbene contents of grapevine cluster stems as potential source of resveratrol in wine,” Vitis, vol. 36, no. 3, pp. 115–118, 1997. View at Google Scholar · View at Scopus
  13. P. Waffo-Teguo, D. Lee, M. Cuendet, J.-M. Mërillon, J. M. Pezzuto, and A. Douglas Kinghorn, “Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures,” Journal of Natural Products, vol. 64, no. 1, pp. 136–138, 2001. View at Publisher · View at Google Scholar · View at Scopus
  14. R. H. Cichewicz, S. A. Kouzi, and M. T. Hamann, “Dimerization of resveratrol by the grapevine pathogen Botrytis cinerea,” Journal of Natural Products, vol. 63, no. 1, pp. 29–33, 2000. View at Publisher · View at Google Scholar · View at Scopus
  15. M. Sbaghi, P. Jeandet, R. Bessis, and P. Leroux, “Degradation of stilbene-type phytoalexins in relation to the pathogenicity of Botrytis cinerea to grapevines,” Plant Pathology, vol. 45, no. 1, pp. 139–144, 1996. View at Publisher · View at Google Scholar · View at Scopus
  16. F. Mattivi, U. Vrhovsek, G. Malacarne et al., “Profiling of resveratrol oligomers, important stress metabolites, accumulating in the leaves of hybrid Vitis vinifera (Merzling × Teroldego) genotypes infected with Plasmopara viticola,” Journal of Agricultural and Food Chemistry, vol. 59, no. 10, pp. 5364–5375, 2011. View at Publisher · View at Google Scholar · View at Scopus
  17. A. D. Pawlus, R. Sahli, J. Bisson et al., “Stilbenoid profiles of canes from Vitis and Muscadinia species,” Journal of Agricultural and Food Chemistry, vol. 61, no. 3, pp. 501–511, 2013. View at Publisher · View at Google Scholar · View at Scopus
  18. M. Jang, L. Cai, G. O. Udeani et al., “Cancer chemopreventive activity of resveratrol, a natural product derived from grapes,” Science, vol. 275, no. 5297, pp. 218–220, 1997. View at Publisher · View at Google Scholar · View at Scopus
  19. L.-M. Hung, J.-K. Chen, S.-S. Huang, R.-S. Lee, and M.-J. Su, “Cardioprotective effect of resveratrol, a natural antioxidant derived from grapes,” Cardiovascular Research, vol. 47, no. 3, pp. 549–555, 2000. View at Publisher · View at Google Scholar · View at Scopus
  20. E. N. Frankel, A. L. Waterhouse, and J. E. Kinsella, “Inhibition of human LDL oxidation by resveratrol,” The Lancet, vol. 341, no. 8852, pp. 1103–1104, 1993. View at Google Scholar · View at Scopus
  21. L. Frémont, L. Belguendouz, and S. Delpal, “Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids,” Life Sciences, vol. 64, no. 26, pp. 2511–2521, 1999. View at Publisher · View at Google Scholar · View at Scopus
  22. A. A. E. Bertelli, L. Giovannini, D. Giannessi et al., “Antiplatelet activity of synthetic and natural resveratrol in red wine,” International Journal of Tissue Reactions, vol. 17, no. 1, pp. 1–3, 1995. View at Google Scholar · View at Scopus
  23. C. R. Pace-Asciak, S. E. Hahn, E. P. Diamandis, G. Soleas, and D. M. Goldberg, “The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease,” Clinica Chimica Acta, vol. 235, no. 2, pp. 207–219, 1995. View at Publisher · View at Google Scholar · View at Scopus
  24. L. Bavaresco, F. Mattivi, M. de Rosso, and R. Flamini, “Effects of elicitors, viticultural factors, and enological practices on resveratrol and stilbenes in Grapevine and Wine,” Mini-Reviews in Medicinal Chemistry, vol. 12, no. 13, pp. 1366–1381, 2012. View at Publisher · View at Google Scholar · View at Scopus
  25. R. L. Geahlen and J. L. McLaughlin, “Piceatannol (3,4,3,5-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor,” Biochemical and Biophysical Research Communications, vol. 165, no. 1, pp. 241–245, 1989. View at Publisher · View at Google Scholar · View at Scopus
  26. M. Swanson-Mungerson, M. Ikeda, L. Lev, R. Longnecker, and T. Portis, “Identification of latent membrane protein 2A (LMP2A) specific targets for treatment and eradication of Epstein-Barr virus (EBV)-associated diseases,” Journal of Antimicrobial Chemotherapy, vol. 52, no. 2, pp. 152–154, 2003. View at Publisher · View at Google Scholar · View at Scopus
  27. M. Larrosa, F. A. Tomás-Barberán, and J. C. Espín, “The grape and wine polyphenol piceatannol is a potent inducer of apoptosis in human SK-Mel-28 melanoma cells,” European Journal of Nutrition, vol. 43, no. 5, pp. 275–284, 2004. View at Publisher · View at Google Scholar · View at Scopus
  28. R. Di Stefano and R. Flamini, “High performance liquid chromatography analysis of grape and wine polyphenols,” in Hyphenated Techniques in Grape & Wine Chemistry, pp. 33–80, John Wiley & Sons, Hoboken, NJ, USA, 2008. View at Google Scholar
  29. R. Flamini and M. de Rosso, “Polyphenols analysis by liquid-mass spectrometry,” in Hyphenated Techniques in Grape & Wine Chemistry, pp. 81–128, John Wiley & Sons, Hoboken, NJ, USA, 2008. View at Google Scholar
  30. M. de Rosso, A. Panighel, A. D. Vedova, L. Stella, and R. Flamini, “Changes in chemical composition of a red wine aged in acacia, cherry, chestnut, mulberry, and oak wood barrels,” Journal of Agricultural and Food Chemistry, vol. 57, no. 5, pp. 1915–1920, 2009. View at Publisher · View at Google Scholar · View at Scopus
  31. L. Stella, M. De Rosso, A. Panighel, A. Dalla Vedova, R. Flamini, and P. Traldi, “Collisionally induced fragmentation of [M-H]- species of resveratrol and piceatannol investigated by deuterium labelling and accurate mass measurements,” Rapid Communications in Mass Spectrometry, vol. 22, no. 23, pp. 3867–3872, 2008. View at Publisher · View at Google Scholar · View at Scopus
  32. S. Pati, M. T. Liberatore, G. Gambacorta, D. Antonacci, and E. la Notte, “Rapid screening for anthocyanins and anthocyanin dimers in crude grape extracts by high performance liquid chromatography coupled with diode array detection and tandem mass spectrometry,” Journal of Chromatography A, vol. 1216, no. 18, pp. 3864–3868, 2009. View at Publisher · View at Google Scholar · View at Scopus
  33. D. Favretto and R. Flamini, “Application of electrospray ionization mass spectrometry to the study of grape anthocyanins,” American Journal of Enology and Viticulture, vol. 51, no. 1, pp. 55–64, 2000. View at Google Scholar · View at Scopus
  34. R. Flamini, M. de Rosso, A. Smaniotto et al., “Fast analysis of isobaric grape anthocyanins by chip-liquid chromatography/mass spectrometry,” Rapid Communications in Mass Spectrometry, vol. 23, no. 18, pp. 2891–2896, 2009. View at Publisher · View at Google Scholar · View at Scopus
  35. P. Arapitsas, M. Scholz, U. Vrhovsek et al., “A metabolomic approach to the study of wine micro-oxygenation,” PLoS ONE, vol. 7, no. 5, Article ID e37783, 2012. View at Publisher · View at Google Scholar · View at Scopus
  36. A. Cuadros-Inostroza, P. Giavalisco, J. Hummel, A. Eckardt, L. Willmitzer, and H. Peña-Cortés, “Discrimination of wine attributes by metabolome analysis,” Analytical Chemistry, vol. 82, no. 9, pp. 3573–3580, 2010. View at Publisher · View at Google Scholar · View at Scopus
  37. L. Vaclavik, O. Lacina, J. Hajslova, and J. Zweigenbaum, “The use of high performance liquid chromatography-quadrupole time-of-flight mass spectrometry coupled to advanced data mining and chemometric tools for discrimination and classification of red wines according to their variety,” Analytica Chimica Acta, vol. 685, no. 1, pp. 45–51, 2011. View at Publisher · View at Google Scholar · View at Scopus
  38. M. Krauss, H. Singer, and J. Hollender, “LC-high resolution MS in environmental analysis: from target screening to the identification of unknowns,” Analytical and Bioanalytical Chemistry, vol. 397, no. 3, pp. 943–951, 2010. View at Publisher · View at Google Scholar · View at Scopus
  39. R. Flamini, M. de Rosso, F. de Marchi et al., “An innovative approach to grape metabolomics: stilbene profiling by suspect screening analysis,” Metabolomics, vol. 9, no. 6, pp. 1243–1253, 2013. View at Publisher · View at Google Scholar · View at Scopus
  40. S. Kueger, D. Steinhauser, L. Willmitzer, and P. Giavalisco, “High-resolution plant metabolomics: from mass spectral features to metabolites and from whole-cell analysis to subcellular metabolite distributions,” The Plant Journal, vol. 70, no. 1, pp. 39–50, 2012. View at Publisher · View at Google Scholar · View at Scopus
  41. T. R. Sana, J. C. Roark, X. Li, K. Waddell, and S. M. Fischer, “Molecular formula and METLIN personal metabolite database matching applied to the identification of compounds generated by LC/TOF-MS,” Journal of Biomolecular Techniques, vol. 19, no. 4, pp. 258–266, 2008. View at Google Scholar · View at Scopus
  42. K. Hanhineva, I. Rogachev, H. Kokko et al., “Non-targeted analysis of spatial metabolite composition in strawberry (Fragaria × ananassa) flowers,” Phytochemistry, vol. 69, no. 13, pp. 2463–2481, 2008. View at Publisher · View at Google Scholar · View at Scopus
  43. M. Brown, W. B. Dunn, P. Dobson et al., “Mass spectrometry tools and metabolite-specific databases for molecular identification in metabolomics,” Analyst, vol. 134, no. 7, pp. 1322–1332, 2009. View at Publisher · View at Google Scholar · View at Scopus
  44. R. C. H. De Vos, S. Moco, A. Lommen, J. J. B. Keurentjes, R. J. Bino, and R. D. Hall, “Untargeted large-scale plant metabolomics using liquid chromatography coupled to mass spectrometry,” Nature Protocols, vol. 2, no. 4, pp. 778–791, 2007. View at Publisher · View at Google Scholar · View at Scopus
  45. A. Scalbert, L. Brennan, O. Fiehn et al., “Mass-spectrometry-based metabolomics: limitations and recommendations for future progress with particular focus on nutrition research,” Metabolomics, vol. 5, no. 4, pp. 435–458, 2009. View at Publisher · View at Google Scholar · View at Scopus
  46. A. I. Romero-Pérez, M. Ibern-Gómez, R. M. Lamuela-Raventós, and M. C. de La Torre-Boronat, “Piceid, the major resveratrol derivative in grape juices,” Journal of Agricultural and Food Chemistry, vol. 47, no. 4, pp. 1533–1536, 1999. View at Publisher · View at Google Scholar · View at Scopus
  47. B. Baderschneider and P. Winterhalter, “Isolation and characterization of novel stilbene derivatives from Riesling wine,” Journal of Agricultural and Food Chemistry, vol. 48, no. 7, pp. 2681–2686, 2000. View at Publisher · View at Google Scholar · View at Scopus
  48. X. Vitrac, C. Castagnino, P. Waffo-Téguo et al., “Polyphenols newly extracted in red wine from Southwestern France by centrifugal partition chromatography,” Journal of Agricultural and Food Chemistry, vol. 49, no. 12, pp. 5934–5938, 2001. View at Publisher · View at Google Scholar · View at Scopus
  49. R. Pezet, C. Perret, J. B. Jean-Denis, R. Tabacchi, K. Gindro, and O. Viret, “δ-viniferin, a resveratrol dehydrodimer: one of the major stilbenes synthesized by stressed grapevine leaves,” Journal of Agricultural and Food Chemistry, vol. 51, no. 18, pp. 5488–5492, 2003. View at Publisher · View at Google Scholar · View at Scopus
  50. T. Püssa, J. Floren, P. Kuldkepp, and A. Raal, “Survey of grapevine Vitis vinifera stem polyphenols by liquid chromatography-diode array detection-tandem mass spectrometry,” Journal of Agricultural and Food Chemistry, vol. 54, no. 20, pp. 7488–7494, 2006. View at Publisher · View at Google Scholar · View at Scopus
  51. J. B. Jean-Denis, R. Pezet, and R. Tabacchi, “Rapid analysis of stilbenes and derivatives from downy mildew-infected grapevine leaves by liquid chromatography-atmospheric pressure photoionisation mass spectrometry,” Journal of Chromatography A, vol. 1112, no. 1-2, pp. 263–268, 2006. View at Publisher · View at Google Scholar · View at Scopus
  52. A. D. Pawlus, P. Waffo-Téguo, J. Shaver, and J.-M. Mérillon, “Stilbenoid chemistry from wine and the genus Vitis, a review,” Journal International des Sciences de la Vigne et du Vin, vol. 46, no. 2, pp. 57–111, 2012. View at Google Scholar · View at Scopus
  53. Y. Takaya, K. Terashima, K.-X. Yan, and M. Niwa, “(+)-Viniferol D, a new stilbenetrimer from the stem of Vitis vinifera ‘Kyohou’,” Heterocycles, vol. 60, no. 6, pp. 1433–1439, 2003. View at Publisher · View at Google Scholar · View at Scopus
  54. H. A. Guebailia, K. Chira, T. Richard et al., “Hopeaphenol: the first resveratrol tetramer in wines from North Africa,” Journal of Agricultural and Food Chemistry, vol. 54, no. 25, pp. 9559–9564, 2006. View at Publisher · View at Google Scholar · View at Scopus
  55. F. Mazzotti, L. DiDonna, H. Benabdelkamel, B. Gabriele, A. Napoli, and G. Sindona, “The assay of pterostilbene in spikedmatrices by liquid chromatography tandemmass spectrometry and isotope dilution method,” Journal of Mass Spectrometry, vol. 45, no. 4, pp. 358–363, 2010. View at Publisher · View at Google Scholar · View at Scopus
  56. M. Adrian, P. Jeandet, A. C. Douillet-Breuil, D. Levite, S. Debord, and R. Bessis, “Assay of resveratrol and derivative stilbenes in wines by direct injection high performance liquid chromatography,” American Journal of Enology and Viticulture, vol. 51, no. 1, pp. 37–41, 2000. View at Google Scholar · View at Scopus
  57. M. Adrian, P. Jeandet, A. C. Douillet-Breuil, L. Tesson, and R. Bessis, “Stilbene content of mature Vitis vinifera berries in response to UV-C elicitation,” Journal of Agricultural and Food Chemistry, vol. 48, no. 12, pp. 6103–6105, 2000. View at Publisher · View at Google Scholar · View at Scopus
  58. A.-C. Douillet-Breuil, P. Jeandet, M. Adrian, and R. Bessis, “Changes in the phytoalexin content of various Vitis spp. in response to ultraviolet C elicitation,” Journal of Agricultural and Food Chemistry, vol. 47, no. 10, pp. 4456–4461, 1999. View at Publisher · View at Google Scholar · View at Scopus
  59. V. Jerkovic, F. Nguyen, S. Nizet, and S. Collin, “Combinatorial synthesis, reversed-phase and normal-phase high-performance liquid chromatography elution data and liquid chromatography/positive atmospheric pressure chemical ionization tandem mass spectra of methoxylated and glycosylated resveratrol analogues,” Rapid Communications in Mass Spectrometry, vol. 21, no. 15, pp. 2456–2466, 2007. View at Publisher · View at Google Scholar · View at Scopus