Direct analysis of glucuronidated metabolites of main olive oil phenols in human urine after dietary consumption of virgin olive oil

Food Chemistry

Volumn 126, Issue 1, 2011, Pages 306-314

  Khymenets, Olha ^a,b,c   Farré, Magí ^a,d   Pujadas, Mitona ^a,b   Ortiz, Erika ^a   Joglar, Jesús ^e   Covas, Maria I ^b,f   De La Torre, Rafael ^a,b,c  

^a HOSPITAL DEL MAR   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c UNIVERSITAT POMPEU FABRA   (Spain)

^d UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^e INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

^f INST MUNIC D INVESTIGACIO MEDICA   (Spain)

Author keywords

Glucuronides; Metabolism; Olive oil phenols; Urinary excretion

Indexed keywords

ANALYTES; CONCENTRATION RANGES; DIRECT ANALYSIS; EXCRETION RATES; GLUCURONIDES; HUMAN URINE; METHOD VALIDATIONS; OLIVE OIL; OLIVE OIL PHENOLS; POLYPHENOLS; STANDARD REQUIREMENTS; TYROSOL; URINARY EXCRETION; VALIDATED METHODS; VIRGIN OLIVE OIL;

BIOMOLECULES; BODY FLUIDS; CHEMICAL ANALYSIS; METABOLISM; METABOLITES; PHYSIOLOGY; VEGETABLE OILS;

PHENOLS;

3' O HYDROXYTYROSOL GLUCURONIDE; 4' O HOMOVANILLYL ALCOHOL; 4' O HYDROXYTYROSOL GLUCURONIDE; 4' O TYROSOSOL GLUCURONIDE; GLUCURONIDE; HOMOVANILLYL ALCOHOL; HYDROXYTYROSOL; OLIVE OIL; PHENOL DERIVATIVE; TYROSOL; UNCLASSIFIED DRUG;

ADULT; ARTICLE; DIET; FEMALE; FOOD INTAKE; GLUCURONIDATION; HUMAN; HUMAN EXPERIMENT; MALE; METABOLITE; NORMAL HUMAN; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; URINALYSIS; VALIDATION STUDY;

EID: 78650222669     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2010.10.044     Document Type: Article

References (32)

1. L. Antonio, J. Xu, J.M. Little, B. Burchell, J. Magdalou, and A. Radominska-Pandya Glucuronidation of catechols by human hepatic, gastric, and intestinal microsomal UDP-glucuronosyltransferases (UGT) and recombinant UGT1A6, UGT1A9, and UGT2B7 Archives of Biochemistry and Biophysics 411 2003 251 261
2. G.P. Cartoni, F. Coccioli, and M. Spagnoli Analysis of ethereal extracts of wines and other alcoholic beverages by high-performance liquid chromatography with microbore columns Journal of Chromatography A 782 1997 219 226
3. D. Caruso, F. Visioli, R. Patelli, C. Galli, and G. Galli Urinary excretion of olive oil phenols and their metabolites in humans Metabolism 50 2001 1426 1428
4. A.F. Cicero, S. Nascetti, M.C. López-Sabater, R. Elosua, J.T. Salonen, and K. Nyyssönen Changes in LDL fatty acid composition as a response to olive oil treatment are inversely related to lipid oxidative damage: The Eurolive study Journal of the American College of Nutrition 27 2008 314 320
5. G. Corona, X. Tzounis, M. Assunta Dess, M. Deiana, E.S. Debnam, and F. Visioli The fate of olive oil polyphenols in the gastrointestinal tract: implications of gastric and colonic microflora-dependent biotransformation Free Radical Research 40 2006 647 658
6. M.I. Covas, K. Nyyssönen, H.E. Poulsen, J. Kaikkonen, H.J. Zunft, and H. Kiesewetter The effect of polyphenols in olive oil on heart disease risk factors: a randomized trial Annals of Internal Medicine 145 2006 333 341
7. M.I. Covas, V. Ruiz-Gutiérrez, R. de la Torre, A. Kafatos, R.M. Lamuela-Raventós, and J. Osada Minor components of olive oil: evidence to date of health benefits in humans Nutrition Reviews 64 2006 20 30
8. S. D'Angelo, C. Manna, V. Migliardi, O. Mazzoni, P. Morrica, and G. Capasso Pharmacokinetics and metabolism of hydroxytyrosol, a natural antioxidant from olive oil Drug Metabolism and Disposition 29 2001 1492 1498
9. R. de la Torre, M.I. Covas, M.A. Pujadas, M. Fitó, and M. Farré Is dopamine behind the health benefits of red wine? European Journal of Nutrition 45 2006 307 310
10. K. de la Torre-Carbot, O. Jauregui, A.I. Castellote, R.M. Lamuela-Raventós, M.I. Covas, and I. Casals Rapid high-performance liquid chromatography-electrospray ionization tandem mass spectrometry method for qualitative and quantitative analysis of virgin olive oil phenolic metabolites in human low-density lipoproteins Journal of Chromatography A 1116 2006 69 75
11. D. Di Tommaso, R. Calabrese, and D. Rotilio Identification and quantitation of hydroxytyrosol in Italian wines Journal of High Resolution Chromatography 21 1998 549 553
12. D.J. Edwards, and M. Rizk Conversion of 3,4-dihydroxyphenylalanine and deuterated 3,4-dihydroxyphenylalanine to alcoholic metabolites of catecholamines in rat brain Journal of Neurochemistry 36 1981 1641 1647 (Pubitemid 11083535)
13. M. Fitó, M.I. Covas, R.M. Lamuela-Raventós, J. Vila, L. Torrents, and C. de la Torre Protective effect of olive oil and its phenolic compounds against low density lipoprotein oxidation Lipids 35 2000 633 638
14. D.S. Goldstein, G. Eisenhofer, and I.J. Kopin Sources and significance of plasma levels of catechols and their metabolites in humans Journal of Pharmacology and Experimental Therapeutics 305 2003 800 811
15. C. Hartmann, J. Smeyers-Verbeke, D.L. Massart, and R.D. McDowall Validation of bioanalytical chromatographic methods Journal of Pharmaceutical and Biomedical Analysis 14 1998 193 218
16. O. Khymenets, J. Joglar, P. Clapes, T. Parella, M.I. Covas, and R. de la Torre Biocatalyzed synthesis and structural characterization of monoglucuronides of hydroxytyrosol, tyrosol, homovanillic alcohol, and 3-(4'-hydroxyphenyl) propanol Advanced Synthesis and Catalysis 348 2006 2155 2162
17. C. La Vecchia Association between Mediterranean dietary patterns and cancer risk Nutrition Reviews 67 2009 S126 129
18. H. Lu, X. Meng, C. Li, S. Sang, C. Patten, and S. Sheng Glucuronides of tea catechins: Enzymology of biosynthesis and biological activities Drug Metabolism and Disposition 31 2003 452 461
19. C. Manna, P. Galletti, G. Maisto, V. Cucciolla, S. D'Angelo, and V. Zappia Transport mechanism and metabolism of olive oil hydroxytyrosol in Caco-2 cells FEBS Letters 470 2000 341 344
20. R. Mateos, L. Goya, and L. Bravo Metabolism of the olive oil phenols hydroxytyrosol, tyrosol, and hydroxytyrosyl acetate by human hepatoma HepG2 cells Journal of Agricultural and Food Chemistry 53 2005 9897 9905
21. E. Miró-Casas, M.I. Covas, M. Farre, M. Fito, J. Ortuño, and T. Weinbrenner Hydroxytyrosol disposition in humans Clinical Chemistry 49 2003 945 952
22. E. Miró-Casas, M.I. Covas, M. Fitó, M. Farré- Albadalejo, J. Marrugat, and R. de la Torre Tyrosol and hydroxytyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans European Journal of Clinical Nutrition 57 2003 186 190
23. E. Miró-Casas, M. Farré Albaladejo, M.I. Covas, J.O. Rodriguez, E. Menoyo-Colomer, and R.M. Lamuela-Raventós Capillary gas chromatography-mass spectrometry quantitative determination of hydroxytyrosol and tyrosol in human urine after olive oil intake Analytical Biochemistry 294 2001 63 72
24. N. Nenadis, L.F. Wang, M.Z. Tsimidou, and H.Y. Zhang Radical scavenging potential of phenolic compounds encountered in O. europaea products as indicated by calculation of bond dissociation enthalpy and ionization potential values Journal of Agricultural and Food Chemistry 53 2005 295 299
25. M. Servili, and G.F. Montedoro Contribution of phenolic compounds to virgin olive oil quality European Journal of Lipid Science and Technology 104 2002 602 613
26. A. Trichopoulou, T. Costacou, C. Bamia, and D. Trichopoulos Adherence to a Mediterranean diet and survival in a Greek population The New England Journal of Medicine 348 2003 2599 2608
27. K.L. Tuck, M.P. Freeman, P.J. Hayball, G.L. Stretch, and I. Stupans The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats Journal of Nutrition 131 2001 1993 1996
28. K.L. Tuck, P.J. Hayball, and I. Stupans Structural characterization of the metabolites of hydroxytyrosol, the principal phenolic component in olive oil, in rats Journal of Agricultural and Food Chemistry 50 2002 2404 2409
29. R.H. Tukey, and C.P. Strassburg Human UDP-glucuronosyltransferases: metabolism, expression, and disease Annual Review of Pharmacology and Toxicology 40 2000 581 616
30. F. Visioli, C. Galli, F. Bornet, A. Mattei, R. Patelli, and G. Galli Olive oil phenolics are dose-dependently absorbed in humans FEBS Letters 468 2000 159 160
31. F. Visioli, C. Galli, S. Grande, K. Colonnelli, C. Patelli, and G. Galli Hydroxytyrosol excretion differs between rats and humans and depends on the vehicle of administration Journal of Nutrition 133 2003 2612 2615
32. T. Weinbrenner, M. Fitó, R. de la Torre, G.T. Saez, P. Rijken, and C. Tormos Olive oils high in phenolic compounds modulate oxidative/ antioxidative status in men Journal of Nutrition 134 2004 2314 2321