Major phenolic compounds in olive oil: Metabolism and health effects

Journal of Nutritional Biochemistry

Volumn 13, Issue 11, 2002, Pages 636-644

  Tuck, Kellie L ^a   Hayball, Peter J ^a  

^a UNIVERSITY OF SOUTH AUSTRALIA   (Australia)

Author keywords

Hydroxytyrosol; Mediterranean diet; Oleuropein; Olive oil; Phenolic compounds; Tyrosol

Indexed keywords

3,4 DIHYDROXYPHENYLACETIC ACID; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ANTIOXIDANT; CINNAMIC ACID; ELENOL; FREE RADICAL; GLUCURONIDE; HOMOVANILLIC ACID; HYDROXYTYROSOL; OLEUROPEIN; OLIVE OIL; PARA COUMARIC ACID; PHENOL DERIVATIVE; SCAVENGER; SULFATE; TYROSOL;

ABSORPTION; ANALYTIC METHOD; ANTIMICROBIAL ACTIVITY; ANTIOXIDANT ACTIVITY; BACTERIAL STRAIN; CANCER INCIDENCE; COLON CANCER; CONJUGATE; DIETARY INTAKE; HUMAN; INCIDENCE; ISCHEMIC HEART DISEASE; MEDICAL LITERATURE; METABOLISM; PROSTATE CANCER; REVIEW; SOUTHERN EUROPE; VEGETARIAN DIET;

BACTERIA (MICROORGANISMS); LETHRINIDAE;

EID: 0036849837     PISSN: 09552863     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0955-2863(02)00229-2     Document Type: Review

References (53)

1. Rose D.P., Boyar A.P., Wynder E.L. International comparison of mortality rates for cancer of the breast, ovary, prostate, and colon and per capita food consumption. Cancer. 58:1986;2363-2371.
2. Quaranta G., Rotundo V. Economic and commercial prospects for olive oil in view of the changes in the common market organisation (CMO) (Part one). Olivæ 91:2000;20-24.
3. Montedoro G. Phenolic substances present in virgin olive oil. Note 1. Identification of phenolic acids and their antioxidant power. Sci Technol Aliment. 2:1972;177-186.
4. Kohyama N., Nagata T., Fujimoto S., Sekiya K. Inhibition of arachidonate lipoxygenase activities by 2-(3,4-dihydroxyphenyl)ethanol, a phenolic compound from olives. Biosci Biotechnol Biochem. 61:1997;347-350.
5. Manna C., Galletti P., Cucciolla V., Moltedo O., Leone A., Zappia V. The protective effect of the olive oil polyphenol (3,4-dihydroxyphenyl)-ethanol counteracts reactive oxygen metabolite-induced cytotoxicity in Caco-2 cells. J Nutr. 127:1997;286-292.
6. Saija A., Trombetta D., Tomaino A., Lo Cascio R., Princi P., Uccella N., Bonina F., Castelli F. In vitro evaluation of the antioxidant activity and biomembrane interaction of the plant phenols oleuropein and hydroxy-tyrosol. Int J Pharmaceut. 166:1998;123-133.
7. Visioli F., Bellomo G., Montedoro G., Galli C. Low density lipoprotein oxidation is inhibited in vitro by olive oil constituents. Atherosclerosis. 117:1995;25-32.
8. Visioli F., Galli C. Oleuropein protects low density lipoprotein from oxidation. Life Sci. 55:1994;1965-1971.
9. Boskov D. Olive oil chemistry and technology. 1996;115-117 AOCS Press, Illinois, USA.
10. Gutfinger T. Phenols in olive oil. J Am Oil Chem Soc. 68:1981;966-968.
11. Brenes M., Garcia A., Garcia P., Rios J.J., Garrido A. Phenolic Compounds in Spanish Olive Oils. J Agric Food Chem. 47:1999;3535-3540.
12. Owen R.W., Giacosa A., Hull W.E., Haubner R., Spiegelhalder B., Bartsh H. The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. Europ. J. Cancer. 36:2000;1235-1247.
13. Visioli F., Galli C. Olive oil phenols and their potential effects on human health. J Agric Food Chem. 46:1998;4292-4296.
14. Montedoro G., Servili N., Baldioli M., Miniati E. Simple and hydrolyzable phenolic compounds in virgin olive oil their extraction, separation, and quantification and semiquantitative evaluation by HPLC . J Agric Food Chem. 40:1992;1571-1576.
15. Maestro-Durán R., León-Cabello R., Ruíz-Gutierrez V., Fiestas P., Vázquez-Roncero A. Glúcosidos fenólicos amargos de la semilla del olivo (Olea europea). Grasas y aceites. 45:1994;332-335.
16. Amiot M.J., Fleuriet A., Macheix J.J. Importance and evolution of phenolic compounds in olive during growth and maturation. J Agric Food Chem. 34:1996;823-826.
17. Cimato A., Mattei A., Osti M. Variation of polyphenol composition with harvesting period. Acta Horticulturae. 286:1990;453-456.
18. Ryan D., Robards K., Lavee S. Changes in phenolic content of olive during maturation. Int J Food Sci Tech. 34:1999;265-274.
19. Coni E., Di Benedetto R., Di Pasquale M., Masella R., Modesti D., Attei R., Carlini E.A. Protective effect of Oleuropein, and olive oil biophenol, on low density lipoprotein oxidizability in rabbits. Lipids. 35:2000;45-54.
20. Papadopoulos G., Boskou D. Antioxidant effect of natural phenols on olive oil. J Am Oil Chem Soc. 68:1991;669-671.
21. Tsimidou M., Papadopoulos G., Boskou D. Phenolic compounds and stability of virgin olive oil - Part I. Food Chem. 45:1992;141-144.
22. Baraldi P.G., Simoni D., Manfredine S., Menziani E. Preparation of 3,4-dihydroxy-1-benzeneethanol a reinvestigation . Liebigs Ann Chem. 83:1983;684-686.
23. Bai C., Yan X., Takenaka M., Sekiya S., Nagata T. Determination of synthetic hydroxytyrosol in rat plasma by GC-MS. J Agric Food Chem. 46:1998;3998-4001.
24. Tuck K.L., Tan H., Hayball P.J. Synthesis of tritiated hydroxytyrosol. J Agric Food Chem. 48:2000;4087-4090.
25. Verhe R., Papadopoulos G., Boskou D. Preparation of hydroxytyrosol. Bull. Liason-Groupe Polyphenols. 15:1992;237-244.
26. Espin J.C., Soler-Rivas C., Cantos E., Tomas-Barberan F.A., Wichers H.J. Synthesis of the antioxidant hydroxytyrosol using tyrosinase as biocatalyst. J Agric Food Chem. 49:2001;1187-1193.
27. Tuck K.L., Tan H., Hayball P.J. A simple procedure for the deuteriation of phenols. J Labeled Compd Radiopharm. 43:2000;817-823.
28. Manna C., Galletti P., Maisto G., Cucciolla V., D'Angelo S., Zappia V. Transport mechanism and metabolism of olive oil hydroxytyrosol in Caco-2 cells. FEBS Lett. 470:2000;341-344.
29. Ruiz-Gutierrez V., Juan M.E., Cert A., Planas J.M. Determination of hydroxytyrosol in plasma by HPLC. Anal Chem. 72:2000;4458-4461.
30. 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. 468:2000;159-160.
31. Grignaffini P., Roma P., Galli C., Catapano A.L. Protection of low-density lipoprotein from oxidation by 3,4-dihydroxyphenylethanol. Lancet. 343:1994;1296-1297.
32. 2-isoprostanes in oxidized low density lipoprotein inhibitory effect of hydroxytyrosol . Pharmacol Res. 31:1995;275-279.
33. Petroni A., Blasevich M., Papini N., Salami M., Sala A., Galli C. Inhibition of leukocyte leukotriene B-4 production by an olive oil-derived phenol identified by mass-spectrometry. Thrombosis Res. 87:1997;315-322.
34. Petroni A., Blasevich M., Salami M., Servili M., Montedoro G.F., Galli C. A phenolic antioxidant extracted from olive oil inhibits platelet aggregation and arachidonic acid metabolism in vitro. World Rev Nutr Diet. 75:1994;169-172.
35. Petroni A., Blasevich M., Salami M., Papini N., Montedoro G.F., Galli C. Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil. Thromb Res. 78:1995;151-160.
36. Stupans I., Stretch G., Hayball P. Olive oil phenols inhibit human hepatic microsomal activity. J Nutr. 130:2000;2367-2370.
37. Stupans I., Murray M., Kirlich A., Tuck K.L., Hayball P.J. Inactivation of cytochrome P450 by the food-derived complex phenol oleuropein. Food Chem Toxicol. 39:2001;1119-1124.
38. Gordon M.H., Paiva-Martins F., Almeida M. Antioxidant activity of hydroxytyrosol acetate compared with that of other olive oil polyphenols. J Agric Food Chem. 49:2001;2480-2485.
39. Briante R., La Cara F., Pia Tonziello M., Febbraio F., Nucci R. Antioxidant activity of the main bioactive derivatives from oleuropein hydrolysis by hyperthermophilic β-glycosidase. J Agric Food Chem. 49:2001;3198-3203.
40. Tuck K.L., Hayball P.J., Stupans I. Structural characterisation of the metabolites of hydroxytyrosol, the principal phenolic component in olive oil, in rats. J Agric Food Chem. 50:2002;2404-2409.
41. Bisignano G., Tomaino A., Lo Cascio R., Crisafi G., Uccella N., Saija A. On the in-vitro antiomicrobial activity of oleuropein and hydroxytyrosol. J Pharm Pharmacol. 31:1999;971-974.
42. De la Puerta R., Dominguez M.E.M., Ruiz-Gutierrez V., Flavill J.A., Hoult J.R.S. Effects of virgin olive oil phenolics on scavenging of reactive nitrogen species and upon nitrergic neurotransmission. Life Sci. 69:2001;1213-1222.
43. Visioli F., Romani A., Mulinacci N., Zarini S., Conte D., Vincieri F.F., Galli C. Antioxidant and other biological activities of olive mill waste waters. J Agric Food Chem. 48:1999;3397-3401.
44. Visioli F., Bellomo G., Galli C. Free radical-scavenging of olive oil phenols. Biochem Biophys Res Commun. 247:1998;60-64.
45. Caruso D., Visioli F., Patelli R., Galli C., Galli G. Urinary excretion of olive oil phenols and their metabolites in humans. Metabolism Clinical and Experimental . 50:2001;1426-1428.
46. Edgecombe S.C., Stretch G.L., Hayball P.J. Oleuropein, an antioxidant polyphenol from olive oil, is poorly absorbed from isolated perfused rat intestine. J Nutr. 130:2000;2996-3002.
47. Artursson P., Karlsson J. Correlation between oral-drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelian (Caco-2) cells. Biochem Biophys Res Commun. 175:1991;880-885.
48. Visioli F., Galli C., Plasmati E., Viappiani S., Hernandez A., Colombo C., Sala A. Olive phenol hydroxytyrosol prevents passive smoking-induced oxidative stress. Circulation. 102:2000;2169-2171.
49. Visioli F., Caruso D., Plasmati E., Patelli R., Mulinacci N., Romani A., Galli G., Galli C. Hydroxytyrosol, as a component of olive mill waste water, is dose-dependently absorbed and increases the antioxidant capacity of rat plasma. Free Rad Res. 34:2001;301-305.
50. Miró-Casas E., Albadalego M.F., Covas M.I., Rodrigues F.O., Colomer E.M., Raventós R.M.L., de la Torre Fornell R. Capillary gas chromatography-mass spectrometry quantitative determination of hydroxytyrosol and tyrosol in human urine after olive intake. Analytical Biochem. 294:2001;63-72.
51. Miró-Casas E., Albadalego M.F., Pianells M.I.C., Colomer M.F., Raventós R.M.L., de la Torre Fornell R. Tyrosol bioavailability in humans after ingestion of virgin olive oil. Clin Chem. 47:2001;341-343.
52. Tuck K.L., Freeman M.P., Hayball P.J., Stretch G.L., Stupans I. The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, following intravenous and oral dosing of labeled compounds to rats. J Nutr. 131:2001;1993-1996.
53. D'Angelo S., Manna C., Migliardi V., Mazzoni O., Morrica P., Capasso G., Pontoni G., Galletti P., Zappia V. Pharmacokinetics and metabolism of hydroxytyrosol, a natural antioxidant from olive oil. Drug Metabolism and Disposition. 29:2001;1492-1498.