Characterization of the cis/trans Isomerization of Resveratrol by High-Performance Liquid Chromatography

Analytical Letters

Volumn 50, Issue 2, 2017, Pages 294-303

  Flieger, J ^a   Tatarczak Michalewska, Małgorzata ^a   Blicharska, Eliza ^a  

^a MEDICAL UNIVERSITY OF LUBLIN   (Poland)

Author keywords

cis trans isomerization; high performance liquid chromatography; resveratrol

Indexed keywords

EID: 85011665357     PISSN: 00032719     EISSN: 1532236X     Source Type: Journal    
DOI: 10.1080/00032719.2016.1178756     Document Type: Article

References (33)

1. Ali, K., F., Maltese, and Y. H., Choi. 2010. Metabolic constituents of grapevine and grape-derived products. Phytochem. Rev. 9 (3):357–78. doi:10.1007/s11101-009-9158-0
2. Almeida, L., M., Vaz-da-Silva, A., Falcão, E., Soares, R., Costa, A. I., Loureiro, C., Fernandes-Lopes, J. F., Rocha, T., Nunes, L., Wright, and P., Soares-da-Silva. 2009. Pharmacokinetic and safety profile of trans-resveratrol in a rising multiple-dose study in healthy volunteers. Mol. Nutr. Food Res. 53:S7–15. doi:10.1002/mnfr.200800177
3. Arce, L., M. T., Tena, A., Rios, and M., Valcarcel. 1998. Determination of trans-resveratrol and other polyphenols in wines by a continuous flow sample clean-up system followed by a capillary electrophoresis separation. Anal. Chim. Acta 359 (1–2):27–38. doi:10.1016/S0003-2670(97)00668-5
4. Baur, J. A., and D. A., Sinclair. 2006. Therapeutic potential of resveratrol:The in vivo evidence. Nat. Rev. Drug Discov. 5:493–506. doi:10.1038/nrd2060
5. Campos-Toimil, M., J., Elies, E., Alvarez, I., Verde, and F., Orallo. 2007. Effects of trans- and cis-resveratrol on Ca2+ handling in A7r5 vascular myocytes. Eur. J. Pharmacol. 577:91–99. doi:10.1016/j.ejphar.2007.08.003
6. Das, D. K., and N., Maulik. 2006. Resveratrol in cardioprotection:A therapeutic promise of alternative medicine. Mol. Interv. 6:36–47. doi:10.1124/mi.6.1.7
7. de Quirós, A. R. B., J., López-Hernández, P., Ferraces-Casais, and M., Lage-Yusty. 2007. Analysis of non-anthocyanin phenolic compounds in wine samples using high performance liquid chromatography with ultraviolet and fluorescence detection. J. Sep. Sci. 30:1262–66. doi:10.1002/jssc.200600489
8. Galeano-Díaz, T., I., Durán-Merás, and D., Airado-Rodríguez. 2007. Isocratic chromatography of resveratrol and piceid after previous generation of fluorescent photoproducts:Wine analysis without sample preparation. J. Sep. Sci. 30:3110–19. doi:10.1002/jssc.200700285
9. German, J. B., and R. L., Walzem. 2000. The health benefits of wine. Annu. Rev. Nutr. 20:561–93. doi:10.1146/annurev.nutr.20.1.561
10. Goldberg, D. M., A., Karumanchiri, E., Ng, J., Yan, E. P., Diamandis, and G. J., Soleas. 1995. Direct gas chromatographic-mass spectrometric method to assay cis-resveratrol in wines:Preliminary survey of its concentration in commercial wines. J. Agric. Food Chem. 43:1245–50. doi:10.1021/jf00053a023
11. Gonçalves, J., and J. S., Câmara. 2011. New method for determination of (E)-resveratrol in wine based on microextraction using packed sorbent and ultra-performance liquid chromatography. J. Sep. Sci. 34:2376–84. doi:10.1002/jssc.201100336
12. Harikumar, K. B., and B. B., Aggarwal. 2008. Resveratrol:A multitargeted agent for age-associated chronic diseases. Cell Cycle 7:1020–35. doi:10.4161/cc.7.8.5740
13. Kanner, J., E., Frankel, R., Granit, B., German, and J. E., Kinsella. 1994. Natural antioxidants in grapes and wines. J. Agric. Food Chem. 42:64–69. doi:10.1021/jf00037a010
14. Kolouchova-Hanzlikova, I., K., Melzoch, V., Filip, and J., Smidrkal. 2004. Rapid method for resveratrol determination by HPLC with electrochemical and UV detection in wines. Food Chem. 87:151–58. doi:10.1016/j.foodchem.2004.01.028
15. Kopp, P., 1998. Resveratrol, a phytoestrogen found in red wine. A possible explanation for the conundrum of the ‘French paradox’? Eur. J. Endocrinol. 138:619–20. doi:10.1530/eje.0.1380619
16. Lamuela, R. M., and A. L., Waterhouse. 1993. Occurrence of resveratrol in selected California wines by a new HPLC method. J. Agric. Food Chem. 41:521–23. doi:10.1021/jf00028a001
17. Langcake, P., and R. J., Pryce. 1976. The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection or injury. Physiol. Plant Pathol. 9:77–86. doi:10.1016/0048-4059(76)90077-1
18. Li, F., Q., Gong, H., Dong, and J., Shi. 2012. Resveratrol, a neuroprotective supplement for Alzheimer’s disease. Curr. Pharm. Des. 18:27–33. doi:10.2174/138161212798919075
19. Lopez, M., F., Martinez, C., Del Valle, C., Orte, and M., Miro. 2001. Analysis of phenolic constituents of biological interest in red wines by high-performance liquid chromatography. J. Chromatogr. A 922:359–63. doi:10.1016/S0021-9673(01)00913-X
20. Lopez, R., P., Dugo, and L., Mondello. 2007. Determination of trans-resveratrol in wine by micro-HPLC with fluorescence detection. J. Sep. Sci. 30:669–72. doi:10.1002/jssc.200600300
21. Mercolini, L., A. M., Saracino, F., Bugamelli, A., Ferranti, M., Malaguti, S., Hrelia, and M. A., Raggi. 2008. HPLC-F analysis of melatonin and resveratrol isomers in wine using an SPE procedure. J. Sep. Sci. 31:1007–14. doi:10.1002/jssc.200700458
22. Orallo, F., 2006. Comparative studies of the antioxidant effects of cis- and trans-resveratrol. Curr. Med. Chem. 13:87–98. doi:10.2174/092986706775197962
23. Pauwels, E. K. J., and M., Kostkiewicz. 2009. The Mediterranean diet, part II:Red wine and cardiovascular disease–more facts, less fancy. Drugs Future 34:565–71. doi:10.1358/dof.2009.034.07.1390996
24. Perestrelo, R., C., Silva, and J. S., Câmara. 2014. Gas chromatography combined with mass spectrometry data as useful approach for wines differentiation according to geographical origin based on global volatile patterns. J. Sep. Sci. 37:1974–81. doi:10.1002/jssc.201400374
25. Renaud, S., and M., de Lorgeril. 1992. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet 339:1523–26. doi:10.1016/0140-6736(92)91277-F
26. Saiko, P., A., Szakmary, W., Jaeger, and T., Szekeres. 2008. Resveratrol and its analogs:Defense against cancer, coronary disease and neurodegenerative maladies or just a fad? Metat. Res. 658:68–94. doi:10.1016/j.mrrev.2007.08.004
27. Selkoe, D. J., 2001. Alzheimer’s disease:Genes, proteins, and therapy. Physiol. Rev. 81:741–66.
28. Sun, A. Y., Q., Wang, A., Simonyi, and G. Y., Sun. 2008. Botanical phenolics and brain health. Neuromolecular Med. 10:259–74. doi:10.1007/s12017-008-8052-z
29. Tanzi, R. E., and L., Bertram. 2005. Twenty years of the Alzheimer’s disease amyloid hypothesis:A genetic perspective. Cell 120:545–55. doi:10.1016/j.cell.2005.02.008
30. Trela, B. C., and A. L., Waterhouse. 1996. Resveratrol:Isomeric molar absorptivities and stability. J. Agric. Food Chem. 44:1253–57. doi:10.1021/jf9504576
31. Vinas, P., C., Lopez-Erroz, J. J., Martin-Hernancez, and M., Henandez-Cordoba. 2000. Determination of phenols in wines by liquid chromatography with photodiode array and fluorescence detection. J. Chromatogr. A 871:85–93. doi:10.1016/S0021-9673(99)01087-0
32. Yáñez, M., N., Fraiz, E., Cano, and F., Orallo. 2006. Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity. Biochem. Biophys. Res. Commun. 344:688–95. doi:10.1016/j.bbrc.2006.03.190
33. Zhu, Y., T., Huang, M., Cregor, H., Long, C. B., Kissinger, and P. T., Kissinger. 2000. Liquid chromatography with multi-channel electrochemical determination of trans-resveratrol in rat blood sampled by automated blood sampling system. J. Chromatogr. B 740:129–33. doi:10.1016/S0378-4347(99)00564-2