Analysis of free hydroxytyrosol in human plasma following the administration of olive oil

Journal of Chromatography A

Volumn 1437, Issue , 2016, Pages 183-190

  Pastor, Antoni ^a,b,c   Rodríguez Morató, Jose ^a,c,d   Olesti, Eulàlia ^a,d   Pujadas, Mitona ^a,c   Pérez Mañá, Clara ^a,b   Khymenets, Olha ^a,c   Fitó, Montserrat ^a,c   Covas, María Isabel ^a,c,e   Solá, Rosa ^f   Motilva, María José ^g   Farré, Magí ^a,b,h   de la Torre, Rafael ^a,c,d  

^a HOSPITAL DEL MAR   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^c Instituto de Salud Carlos III   (Spain)

^d UNIVERSITAT POMPEU FABRA   (Spain)

^e NUPROAS (Nutritional Project Assessment)   (Sweden)

^f UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^g UNIVERSITY OF LLEIDA   (Spain)

^h HOSPITAL UNIVERSITARI GERMANS TRIAS I PUJOL   (Spain)

Author keywords

Benzylamine derivatization; Health; Humans; Hydroxytyrosol; LC MS MS; Virgin olive oil

Indexed keywords

BIOACTIVITY; HEALTH; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHASE SEPARATION; PLASMA (HUMAN); PLASMA DIAGNOSTICS; PLASMA STABILITY;

DERIVATIZATIONS; HUMANS; HYDROXYTYROSOL; LC-MS/MS; VIRGIN OLIVE OIL;

OLIVE OIL;

BENZYLAMINE; EXTRA VIRGIN OLIVE OIL; HYDROXYTYROSOL; OLIVE OIL; 3,4-DIHYDROXYPHENYLETHANOL; EDIBLE OIL; PHENETHYL ALCOHOL; POLYPHENOL;

AREA UNDER THE CURVE; ARTICLE; BLOOD ANALYSIS; CONTROLLED STUDY; DERIVATIZATION; HUMAN; HUMAN EXPERIMENT; LIMIT OF DETECTION; LIMIT OF QUANTITATION; LIQUID CHROMATOGRAPHY; MALE; MAXIMUM PLASMA CONCENTRATION; NORMAL HUMAN; PRECIPITATION; PRIORITY JOURNAL; PURIFICATION; SENSITIVITY AND SPECIFICITY; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; TIME TO MAXIMUM PLASMA CONCENTRATION; VALIDATION STUDY; ANALOGS AND DERIVATIVES; BIOAVAILABILITY; BLOOD; CHEMISTRY; METABOLISM; OLIVE TREE;

BIOLOGICAL AVAILABILITY; BLOOD CHEMICAL ANALYSIS; CHROMATOGRAPHY, LIQUID; DIETARY FATS, UNSATURATED; HUMANS; OLEA; OLIVE OIL; PHENYLETHYL ALCOHOL; POLYPHENOLS; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY;

EID: 84959207382     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2016.02.016     Document Type: Article

References (36)

1. Servili M., Montedoro G. Contribution of phenolic compounds to virgin olive oil quality. Eur. J. Lipid Sci. Technol. 2002, 104:602-613.
2. Owen R.W., Giacosa A., Hull W.E., Haubner R., Spiegelhalder B., Bartsch H. The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. Eur. J. Cancer 2000, 36:1235-1247.
3. Owen R.W., Mier W., Giacosa A., Hull W.E., Spiegelhalder B., Bartsch H. Phenolic compounds and squalene in olive oils: the concentration and antioxidant potential of total phenols simple phenols, secoiridoids, lignansand squalene. Food Chem. Toxicol. 2000, 38:647-659.
4. Trujillo M., Mateos R., Collantes de Teran L., Espartero J.L., Cert R., Jover M., Alcudia F., Bautista J., Cert A., Parrado J. Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems. J. Agric. Food Chem. 2006, 54:3779-3785.
5. Granados-Principal S., Quiles J.L., Ramirez-Tortosa C.L., Sanchez-Rovira P., Ramirez-Tortosa M.C. Hydroxytyrosol: from laboratory investigations to future clinical trials. Nutr. Rev. 2010, 68:191-206.
6. Rietjens S.J., Bast A., Haenen G.R.M.M. New insights into controversies on the antioxidant potential of the olive oil antioxidant hydroxytyrosol. J. Agric. Food Chem. 2007, 55:7609-7614.
7. Visioli F., Galli C., Bornet F., Mattei A., Patelli R., Galli G., Caruso D. Olive oil phenolics are dose-dependently absorbed in humans. FEBS Lett. 2000, 468:159-160.
8. Nousis L., Doulias P.-T., Aligiannis N., Bazios D., Agalias A., Galaris D., Mitakou S. DNA protecting and genotoxic effects of olive oil related components in cells exposed to hydrogen peroxide. Free Radic. Res. 2005, 39:787-795.
9. Aviram M. Interaction of oxidized low density lipoprotein with macrophages in atherosclerosis, and the antiatherogenicity of antioxidants. Eur. J. Clin. Chem. Clin. Biochem. 1996, 34:599-608.
10. González-Santiago M., Martín-Bautista E., Carrero J.J., Fonollá J., Baró L., Bartolomé M.V., Gil-Loyzaga P., López-Huertas E. 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 2006, 188:35-42.
11. Covas M.-I., de la Torre K., Farré-Albaladejo M., Kaikkonen J., Fitó M., López-Sabater C., Pujadas-Bastardes M.A., Joglar J., Weinbrenner T., Lamuela-Raventós R.M., de la Torre R. Postprandial LDL phenolic content and LDL oxidation are modulated by olive oil phenolic compounds in humans. Free Radic. Biol. Med. 2006, 40:608-616.
12. Ruano J., Lopez-Miranda J., Fuentes F., Moreno J.A., Bellido C., Perez-Martinez P., Lozano A., Gómez P., Jiménez Y., Pérez Jiménez F. Phenolic content of virgin olive oil improves ischemic reactive hyperemia in hypercholesterolemic patients. J. Am. Coll. Cardiol. 2005, 46:1864-1868.
13. Weinbrenner T., Fitó M., de la Torre R., Saez G.T., Rijken P., Tormos C., Coolen S., Albaladejo M.F., Abanades S., Schroder H., Marrugat J., Covas M.-I. Olive oils high in phenolic compounds modulate oxidative/antioxidative status in men. J. Nutr. 2004, 134:2314-2321.
14. Hernáez Á., Remaley A.T., Farràs M., Fernández-Castillejo S., Subirana I., Schröder H., Fernández-Mampel M., Muñoz-Aguayo D., Sampson M., Solà R., Farré M., de la Torre R., López-Sabater M.-C., Nyyssönen K., Zunft H.-J.F., Covas M.-I., Fitó M. Olive oil polyphenols decrease LDL concentrations and LDL atherogenicity in men in a randomized controlled trial. J. Nutr. 2015, 145:1692-1697.
15. EFSA, Panel on Dietetic Products, Nutrition and Allergies (NDA), Scientific Opinion on the substantiation of health claims related to polyphenols in olive and protection of LDL particles from oxidative damage (ID 1333, 1638, 1639, 1696, 2865), maintenance of normal blood HDL-cholesterol concentrations (ID 1639), maintenance of normal blood pressure (ID 3781), anti-inflammatory properties (ID 1882), contributes to the upper respiratory tract health (ID 3468), can help to maintain a normal function of gastrointestinal tract (3779), and contributes to body defences against external agents (ID 3467) pursuant to Article 13(1) of Regulation (EC) No 1924/2006, EFSA J. 9 (2011), 2033, . Available online: (accessed on July 2015). http://www.efsa.europa.eu/efsajournal.
16. Miró-Casas E., Covas M.I., Fitó M., Farré-Albadalejo M., Marrugat J., de la Torre R. Tyrosol and hydroxytyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans. Eur. J. Clin. Nutr. 2003, 57:186-190.
17. Khymenets O., Fitó M., Touriño S., Muñoz-Aguayo D., Pujadas M., Torres J.L., Joglar J., Farré M., Covas M.-I., De la Torre R. Antioxidant activities of hydroxytyrosol main metabolites do not contribute to beneficial health effects after olive oil ingestion. Drug Metab. Dispos. 2010, 38:1417-1421.
18. Miró-Casas E., Covas M.-I., Farré M., Fitó M., Ortuño J., Weinbrenner T., Roset P., De la Torre R. Hydroxytyrosol disposition in humans. Clin. Chem. 2003, 49:945-952.
19. Rubió L., Valls R.-M., Macià A., Pedret A., Giralt M., Romero M.-P., de la Torre R., Covas M.-I., Solà R., Motilva M.-J. Impact of olive oil phenolic concentration on human plasmatic phenolic metabolites. Food Chem. 2012, 135:2922-2929.
20. De la Torre R. Bioavailability of olive oil phenolic compounds in humans. Inflammopharmacology 2008, 16:245-247.
21. Vissers M.N., Zock P.L., Katan M.B. Bioavailability and antioxidant effects of olive oil phenols in humans: a review. Eur. J. Clin. Nutr. 2004, 58:955-965.
22. Catalán Ú., López de las Hazas M.-C., Rubió L., Fernández-Castillejo S., Pedret A., de la Torre R., Motilva M.-J., Solà R. Protective effect of hydroxytyrosol and its predominant plasmatic human metabolites against endothelial dysfunction in human aortic endothelial cells. Mol. Nutr. Food Res. 2015, 1-14.
23. Giordano E., Dangles O., Rakotomanomana N., Baracchini S., Visioli F. 3-O-Hydroxytyrosol glucuronide and 4-O-hydroxytyrosol glucuronide reduce endoplasmic reticulum stress in vitro. Food Funct. 2015, 6:3275-3281.
24. Lamuela-Raventós R.M., Covas M.-I., Fitó M., Marrugat J., de la Torre-Boronat M.C. Detection of dietary antioxidant phenolic compounds in human LDL. Clin. Chem. 1999, 45:1870-1872.
25. Konstantinidou V., Covas M.-I., Sola R., Fitó M. Up-to date knowledge on the in vivo transcriptomic effect of the Mediterranean diet in humans. Mol. Nutr. Food Res. 2013, 57:772-783.
26. Miró-Casas E., Farré Albaladejo M., Covas M.-I., Rodriguez J.O., Menoyo Colomer E., Lamuela Raventós R.M., de la Torre R. Capillary gas chromatography-mass spectrometry quantitative determination of hydroxytyrosol and tyrosol in human urine after olive oil intake. Anal. Biochem. 2001, 294:63-72.
27. Weinbrenner T., Fito M., Farre Albaladejo M., Saez G.T., Rijken P., Tormos C., Coolen S., De La Torre R., Covas M.I. Bioavailability of phenolic compounds from olive oil and oxidative/antioxidant status at postprandial state in healthy humans. Drugs Exp. Clin. Res. 2004, 30:207-212.
28. Miró-Casas E., Covas M.-I., Farré M., Fitó M., Ortuño J., Weinbrenner T., Roset P., de la Torre R. Hydroxytyrosol disposition in humans. Clin. Chem. 2003, 49:945-952.
29. Pennington J., Schöneich C., Stobaugh J. Selective fluorogenic derivatization with isotopic coding of catechols and 2-amino phenols with benzylamine: a chemical basis for the relative determination of 3-hydroxy-tyrosine and 3-nitro-tyrosine peptides. Chroma 2007, 66:649-659.
30. García A., Brenes M., García P., Romero C., Garrido A. Phenolic content of commercial olive oils. Eur. Food Res. Technol. 2003, 216:520-525.
31. Rodríguez-Morató J., Xicota L., Fitó M., Farré M., Dierssen M., de la Torre R. Potential role of olive oil phenolic compounds in the prevention of neurodegenerative diseases. Molecules 2015, 20:4655-4680.
32. Kotronoulas A., Pizarro N., Serra A., Robledo P., Joglar J., Rubió L., Hernaéz Á., Tormos C., Motilva M.J., Fitó M., Covas M.-I., Solà R., Farré M., Saez G., de la Torre R. Dose-dependent metabolic disposition of hydroxytyrosol and formation of mercapturates in rats. Pharmacol. Res. 2013, 77:47-56.
33. Suárez M., Romero M.-P., Macià A., Valls R.M., Fernández S., Solà R., Motilva M.-J. Improved method for identifying and quantifying olive oil phenolic compounds and their metabolites in human plasma by microelution solid-phase extraction plate and liquid chromatography-tandem mass spectrometry. J. Chromatogr. B 2009, 877:4097-4106.
34. Ruiz-Gutiérrez V., Juan M.E., Cert A., Planas J.M. Determination of hydroxytyrosol in plasma by HPLC. Anal. Chem. 2000, 72:4458-4461.
35. González-Santiago M., Fonollá J., Lopez-Huertas E. Human absorption of a supplement containing purified hydroxytyrosol, a natural antioxidant from olive oil, and evidence for its transient association with low-density lipoproteins. Pharmacol. Res. 2010, 61:364-370.
36. Pérez-Mañá C., Farré M., Rodríguez-Morató J., Papaseit E., Pujadas M., Fitó M., Robledo P., Covas M.-I., Cheynier V., Meudec E., Escudier J.-L., de la Torre R. Moderate consumption of wine, through both its phenolic compounds and alcohol content, promotes hydroxytyrosol endogenous generation in humans. A randomized controlled trial. Mol. Nutr. Food Res. 2015, 59:1213-1216. 10.1002/mnfr.201400842.