Stability of Hydroxytyrosol in Aqueous Solutions at Different Concentration, Temperature and with Different Ionic Content: A Study Using UPLC-MS — Oak Academic Publishing
Research ArticleOpen AccessGoogle Scholar indexed
Stability of Hydroxytyrosol in Aqueous Solutions at Different Concentration, Temperature and with Different Ionic Content: A Study Using UPLC-MS
The work describes a stability study of hydroxytyrosol (HTyr) in aqueous solutions carried out varying the following parameters: HTyr concentration, temperature and ionic content in the aqueous solution. First, an analytical method based on the use of ultra performance liquid chromatography (UPLC-MS) as analytical technique was developed and validated. The equation of the linear model was A/A<sub>ISTD</sub>= –0.0013 + 0.0117. [HTyr], with a very good linearity, since the R-Squared was 99.9% and the P value of the lack of fit test was higher than 5%. Limits of quantification estimated, CC<sub>α</sub>(α= 0.05%) and CC<sub>β</sub>(β= 0.05%), were 0.2 and 0.4 g/L respectively. As well, the relative standard deviation in the intra-day precision was lower than 3%. Therefore, the method is reproducible. We have applied this methodology to study the stability of HTyr and have observed that the most critical aspect turned to be the ionic content of the aqueous solutions. A tap water with high contents of calcium and magnesium (52 and 21 mg/L) degraded HTyr up to 64% in 48 hours whereas a low mineralization water with low contents of calcium and magnesium (4 and 2 mg/L) produced only 19% degradation.
C. W. Arts and P. C. H. Hollman, “Polyphenols and Disease Risk in Epidemiologic Studies,” American Journal of Clinical Nutrition, Vol. 81, No. 1, 2005, pp. 317S-325S.
I. Rahman, S. K. Biswas and P. A. Kirkham, “Regulation of Inflammation and Redox Signaling by Dietary Polyphenols,” Biochemical Pharmacology, Vol. 72, No. 11, 2006, pp. 1439-1452. doi:10.1016/j.bcp.2006.07.004
T. L. Zern and M. L. Fernandez, “Cardioprotective Effects of Dietary Polyphenols,” Journal of Nutrition, Vol. 135, No. 10, 2005, pp. 2291-2294.
M. Daglia, A. Papetti, P. Grisoli, C. Aceti, C. Dacarro and G. Gazzani, “Antibacterial Activity of Red and White Wine Against Oral Streptococci,” Journal of Agricultural and Food Chemistry, Vol. 55, No. 13, 2007, pp. 5038-5042. doi:10.1021/jf070352q
R. W. Owen, A. Giacosa, W. E. Hull, R. Haubner, B. Spiegelhalder and H. Bartsch, “The Antioxidant/Anticancer Potential of Phenolic Compounds Isolated from Olive Oil,” European Journal of Cancer, Vol. 36, No. 10, 2000, pp. 1235-1247. doi:10.1016/S0959-8049(00)00103-9
A. Keys, “Mediterranean Diet and Public Health: Personal Reflections,” American Journal of Clinical Nutrition, Vol. 61, No. 6, 1995, pp. 1321S-1323S.
P. M. Kris-Etherton, K. D. Hecker, A. Bonanome, S. M. Coval, A. E. Binkoski, K. F. Hilpert, A. E. Griel and T. D. Etherton, “Bioactive Compounds in Foods: Their Role in the Prevention of Cardiovascular Disease and Cancer,” American Journal of Medicine, Vol. 113, No. 9, 2002, pp. 71-88.
H. L. Newmark, “Plant Phenolics as Potential Cancer Prevention Agents,” Advances in Experimental Medicine and Biology, Vol. 401, 1996, pp. 25-34. doi:10.1007/978-1-4613-0399-2_3
L. Rossi, S. Mazzitelli, M. Arciello, C. R. Capo and G. Rotilio, “Benefits from Dietary Polyphenols for Brain Aging and Alzheimer’s Disease,” Neurochemistry Research, Vol. 33, No. 12, 2008, pp. 2390-2400. doi:10.1007/s11064-008-9696-7
A. Geerlings, E. López-Huertas, J. C. Morales, J. Boza and J. Jiménez, “Natural Phenolic Products and Derivatives Thereof for Protection against Neurodegenerative Diseases,” Patent WO 03/082259, 2003.
M. González-Santiago, E. Martín-Bautista, J. J. Carrero, J. Fonollá, L. Baró, M. V. Bartolomé, P. Gil-Loyzaga and E. López-Huertas, “One-Month Administration of Hydroxytyrosol, a Phenolic Antioxidant Present in Olive Oil, to Hyperlipemic Rabbits Improves Blood Lipid Profile, Antioxidant Status and Reduces Atherosclerosis Development,” Atherosclerosis, Vol. 188, No. 1, 2006, pp. 35-42. doi:10.1016/j.atherosclerosis.2005.10.022
M. J. Oliveras-López, G. Berná, E. M. Carneiro, H. López-García de la Serrana, F. Martín and M. C. López, “An Extra-Virgin Olive Oil Rich in Polyphenolic Compounds Has Antioxidant Effects in OF1 Mice,” Journal of Nutrition, Vol. 138, No. 6, 2008, pp. 1074-1078.
C. M. Bitler, T. M. Viale, B. Damaj and R. Crea, “Hydrolyzed Olive Vegetation Water in Mice Has Anti-Inflammatory Activity,” Journal of Nutrition, Vol. 135, No. 6, 2005, pp. 1475-1479.
E. Miro-Casas, M. I. Covas, M. Farre, M. Fito, J. Ortu?o, T. Weinbrenner, P. Roset and R. de la Torre, “Hydroxytyrosol Disposition in Humans,” Clinical Chemisty, Vol. 49, No. 6, 2003, pp. 945-952. doi:10.1373/49.6.945
F. N. Bazoti, E. Gikas, C. Puel, V. Coxam and A. Tsarbopoulos, “Development of a Sensitive and Specific Solid Phase Extraction—Gas Chromatograph—Tandem Mass Spectrometry Method for the Determination of Elenolic Acid, Hydroxytyrosol, and Tyrosol in Rat Urine,” Journal of Agricultural and Food Chemistry, Vol. 53, No. 16, 2005, pp. 6213-6221. doi:10.1021/jf050851w
M. Brenes, A. García, P. García, J. J. Rios and A. Garrido, “Phenolic Compounds in Spanish Olive Oils,” Journal of Agricultural and Food Chemistry, Vol. 47, No. 9, 1999, pp. 3535-3540. doi:10.1021/jf990009o
E. De Marco, M. Savarese, A. Paduano and R. Sacchi, “Characterization and Fractionation of Phenolic Compounds Extracted from Olive Oil Mill Wastewaters,” Food Chemistry, Vol. 104, No. 2, 2007, pp. 858-867. doi:10.1016/j.foodchem.2006.10.005
P. Del Boccio, A. Di Deo, A. De Curtis, N. Celli, L. Iacoviello and D. Rotilio, “Liquid Chromatographytandem Mass Spectrometry Analysis of Oleuropein and Its Metabolite Hydroxytyrosol in Rat Plasma and Urine after Oral Administration,” Journal of Chromatography B, Vol. 785, No. 1, 2003, pp. 47-56. doi:10.1016/S1570-0232(02)00853-X
H. W. Tan, K. L. Tuck, I. Stupans and P. J. Hayball, “Simultaneous Determination of Oleuropein and Hydroxytyrosol in Rat Plasma Using Liquid Chromatography with Fluorescence Detection,” Journal of Chromatography B, Vol. 785, No. 1, 2003, pp. 187-191.
R. Capasso, A. Evidente, S. Avolio and F. Solla, “A Highly Convenient Synthesis of Hydroxytyrosol and Its Recovery from Agricultural Wastewaters,” Journal of Agricultural and Food Chemistry, Vol. 47, No. 4, 1999, pp. 1745-1748. doi:10.1021/jf9809030
P. G. Baraldi, D. Simoni, S. Manfredini and E. Menziani, “Preparation of 3,4-Dihydroxy-1-benzeneethanol: A Reinvestigation,” Liebig’s Annals of Chemistry, Vol. 1983, No. 4, 1983, pp. 684-686. doi:10.1002/jlac.198319830417
Analytical Methods Committee, “Is My Calibration Linear?” Analyst, Vol. 119, No. 11, 1994, pp. 2363-2366. doi:10.1039/an9941902363
“COMMISSION DECISION 2002/657/EC of 12 August 2002 Implementing Council Directive 96/23/EC Concerning the Performance of Analytical Methods and the Interpretation of Results,” Official Journal of the European Communities, 2002, pp. L221/8-L221/36.
P. García, C. Romero, M. Brenes and A. Garrido, “Effect of Metal Cations on the Chemical Oxidation of Olive o-Diphenols in Model Systems,” Journal of Agricultural and Food Chemistry, Vol. 44, No. 8, 1996, pp. 2101- 2105. doi:10.1021/jf9503265
J. J. L. Cilliers and V. L. Singleton, “Nonenzymic Autoxidative Phenolic Browning Reactions in a Caffeic Acid Model System,” Journal of Agricultural and Food Chemistry, Vol. 37, No. 4, 1989, pp. 890-896. doi:10.1021/jf00088a013
D. Vogna, A. Pezzella, L. Panzella, A. Napolitano and M. d’Ischia, “Oxidative Chemistry of Hidroxytyrosol: Isolation and Characterization of Novel Methanoxo Cinobenzodioxinone Derivatives,” Tetrahedron Letters, Vol. 44, No. 45, 2003, pp. 8289-8292. doi:10.1016/j.tetlet.2003.09.066
M. de Lucia, L. Panzella, A. Pezzella, A. Napolitano and M. d’Ischia, “Oxidative Chemistry of the Natural Anti-Oxidant Hydroxytyrosol: Hydrogen Peroxide-Dependent Hydroxylation and Hydroxyquinone/o-Quinone Coupling Pathways,” Tetrahedron, Vol. 62, No. 6, 2006, pp. 1273-1278. doi:10.1016/j.tet.2005.10.055
F. Paiva-Martins and M. H. Gordon, “Interactions of Ferric Ions with Olive Oil Phenolic Compounds,” Journal of Agricultural and Food Chemistry, Vol. 53, No. 7, 2005, pp. 2704-2709. doi:10.1021/jf0481094
A. Bendini, L. Cerretani, S. Vecchi, A. Carrasco-Pancorbo and G. Lecker, “Protective Effects of Extra Virgin Olive Oil Phenolics on Oxidative Stability in the Presence or Absence of Copper Ions,” Journal of Agricultural and Food Chemistry, Vol. 54, No. 13, 2006, pp. 4880-4887. doi:10.1021/jf060481r
F. Paiva-Martins and M. H. Gordon, “Effects of pH and Ferric Ions on the Antioxidant Activity of Olive Polyphenols in Oil-In-Water Emulsions,” Journal of the American Oil Chemists’ Society, Vol. 79, No. 6, 2002, pp. 571-576.
T. Keceli and M. H. Gordon, “Ferric Ions Reduce the Antioxidant Activity of the Phenolic Fraction of Virgin Olive Oil,” Journal of Food Science, Vol. 67, No. 3, 2002, pp. 943-947. doi:10.1111/j.1365-2621.2002.tb09432.x
F. Paiva-Martins, V. Santos, H. Mangericao and M. H. Gordon, “Effects of Copper on the Antioxidant Activity of Olive Polyphenols in Bulk Oil and Oil-In-Water Emulsions,” Journal of Agricultural and Food Chemistry, Vol. 54, No. 10, 2006, pp. 3738-3743. doi:10.1021/jf060033j