Biological activities of phenolic compounds present in virgin olive oil

International Journal of Molecular Sciences

Volumn 11, Issue 2, 2010, Pages 458-479

  Cicerale, Sara ^a   Lucas, Lisa ^a   Keast, Russell ^a  

^a DEAKIN UNIVERSITY   (Australia)

Author keywords

Health benefits; Olive oil phenolic compounds; Virgin olive oil

Indexed keywords

C REACTIVE PROTEIN; GLUTATHIONE; GLUTATHIONE DISULFIDE; GLUTATHIONE PEROXIDASE; HYDROXYTYROSOL; INTERCELLULAR ADHESION MOLECULE 1; INTERLEUKIN 6; LEUKOTRIENE B4; LIPID PEROXIDE; LIPOPROTEIN; OLEOCANTHAL; OLEUROPEIN; OLIVE OIL; PHENOL DERIVATIVE; REACTIVE OXYGEN METABOLITE; THROMBOXANE B2; TYROSOL; UNCLASSIFIED DRUG; VASCULAR CELL ADHESION MOLECULE 1;

ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; CELL FUNCTION; CLINICAL TRIAL; COMPETITIVE INHIBITION; DIETARY INTAKE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG EXCRETION; DRUG METABOLISM; DYSLIPIDEMIA; HUMAN; HYPERCHOLESTEROLEMIA; ISCHEMIC HEART DISEASE; LIPID OXIDATION; LIPOPROTEIN BLOOD LEVEL; MEDITERRANEAN DIET; MORBIDITY; MORTALITY; NONHUMAN; OSSIFICATION; OXIDATIVE STRESS; PERIPHERAL VASCULAR DISEASE; REVIEW; RISK REDUCTION; THROMBOCYTE FUNCTION;

HEALTH BENEFITS; OLIVE OIL PHENOLIC COMPOUNDS; VIRGIN OLIVE OIL;

BLOOD PLATELETS; CELL SURVIVAL; CLINICAL TRIALS AS TOPIC; DNA DAMAGE; HUMANS; LIPIDS; OSTEOGENESIS; OXIDATIVE STRESS; PHENOLS; PLANT OILS;

ANIMALIA;

EID: 77649223901     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms11020458     Document Type: Review

References (143)

1. De Lorgeril, M.; Salen, P.; Martin, J.L.; Monjaud, I.; Delaye, J.; Mamelle, N. Mediterranean diet, traditional risk factors, and the rate of cardiovascular complications after myocardial infarction: final report of the Lyon Diet Heart Study. Circulation 1999, 99, 779-785.
2. Singh, R.B.; Dubnov, G.; Niaz, M.A.; Ghosh, S.; Singh, R.; Rastogi, S.S.; Manor, O.; Pella, D.; Berry, E.M. Effect of an Indo-Mediterranean diet on progression of coronary artery disease in high risk patients (Indo-Mediterranean Diet Heart Study): A randomised single-blind trial. Lancet 2002, 360, 1455-1461.
3. Stark, A.H.; Madar, Z. Olive oil as a functional food: epidemiology and nutritional approaches. Nutr. Rev. 2002, 60, 170-176.
4. Trichopoulou, A.; Costacou, T.; Bamia, C.; Trichopoulos, D. Adherence to a Mediterranean diet and survival in a Greek population. N. Engl. J. Med. 2003, 348, 2599-2608.
5. Visioli, F.; Galli, C. Natural antioxidants and prevention of coronary heart disease: the potential role of olive oil and its minor constituents. Nutr. Metab. Cardio. Dis. 1995, 5, 306-314.
6. Fortes, C.; Forastiere, F.; Farchi, S.; Mallone, S.; Trequattrinni, T.; Anatra, F.; Schmid, G.; Perucci, C.A. The protective effect of the Mediterranean diet on lung cancer. Nutr. Cancer 2003, 46, 30-37.
7. Grasso, S.; Siracusa, L.; Spatafora, C.; Renis, M.; Tringali, C. Hydroxytyrosol lipophilic analogues: Enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection. Bioorg. Chem. 2006, 35, 137-152.
8. Herrera, M.D.; Perez-Guerrero, C.; Marhuenda, E.; Ruiz-Gutierrez, V. Effects of dietary oleicrich oils (virgin olive and high-oleic-acid sunflower) on vascular reactivity in Wistar-Kyoto and spontaneously hypertensive rats. Br. J. Nutr. 2001, 86, 349-357.
9. Matalas, A.-L.; Zampelas, A.; Stavrinos, V.; Wolinsky, I. The Mediterranean Diet: Constituents and Health Promotion; CRC Press: Boca Raton, FL, USA, 2001.
10. Galeone, C.; Talamini, R.; Levi, F.; Pelucchi, C.; Negri, E.; Giacosa, A.; Montella, M.; Franceschi, S.; La Vecchia, C. Fried foods, olive oil and colorectal cancer. Ann. Oncol. 2006, 18, 36-39.
11. Filik, L.; Ozyilkan, O. Olive-oil consumption and cancer risk. Eur. J. Clin. Nutr. 2003, 57, 191.
12. Hu, F.B. The Mediterranean diet and mortality-olive oil and beyond. N. Engl. J. Med. 2003, 348, 2595-2596.
13. Kok, F.J.; Kromhout, D. Atherosclerosis-epidemiological studies on the health effects of a Mediterranean diet. Eur. J. Nutr. 2004, 43, 1S-5S.
14. Kris-Etherton, P.; Eckel, R.H.; Howard, B.V.; St. Jeor, S.; Bazzarre, T.L. AHA Science advisory: Lyon diet heart study. benefits of a mediterranean-style, national cholesterol education program/american heart association step i dietary pattern on cardiovascular disease. Circulation 2001, 103, 1823-1825.
15. Kushi, L.H.; Lenart, E.B.; Willett, W.C. Health implications of Mediterranean diets in light of contemporary knowledge. 2. Meat, wine, fats, and oils. Am. J. Clin. Nutr. 1995, 61, 1416S-1427S.
16. Willett, W.C.; Sacks, F.; Trichopoulou, A.; Drescher, G.; Ferro-Luzzi, A.; Helsing, E.; Trichopoulos, D. Mediterranean diet pyramid: a cultural model for healthy eating. Am. J. Clin. Nutr. 1995, 61, 1402S-1406S.
17. Fung, T.T.; Rexrode, K.M.; Mantzoros, C.S.; Manson, J.E.; Willett, W.C.; Hu, F.B. Mediterranean diet and incidence of and mortality from coronary heart disease and stroke in women. Circulation 2009, 119, 1093-1100.
18. Corona, G.; Spencer, J.P.E.; Dessi, M.A. Extra virgin olive oil phenolics: absorption, metabolism, and biological activities in the GI tract. Toxical. Ind. Health 2009, 25, 285-293.
19. Tripoli, E.; Giammanco, M.; Tabacchi, G.; Di Majo, D.; Giammanco, S.; La Guardia, M. The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health. Nutr. Res. Rev. 2005, 18, 98-112.
20. Harper, C.R.; Edwards, M.C.; Jacobson, T.A. Flaxseed oil supplementation does not affect plasma lipoprotein concentration or particle size in human subjects. J. Nutr. 2006, 136, 2844-2848.
21. Aguilera, C.M.; Mesa, M.D.; Ramirez-Tortosa, M.C.; Nestares, M.T.; Ros, E.; Gil, A. Sunflower oil does not protect against LDL oxidation as virgin olive oil does in patients with peripheral vascular disease. Clin. Nutr. 2004, 23, 673-681.
22. Visioli, F.; Galli, C. Biological properties of olive oil phytochemicals. Crit. Rev. Food Sci. Nutr. 2002, 42, 209-221.
23. Psaltopoulou, T.; Naska, A.; Orfanos, P.; Trichopoulos, D.; Mountokalakis, T.; Trichopoulou, A. Olive oil, the Mediterranean diet, and arterial blood pressure: the Greek European Prospective Investigation into Cancer and Nutrition (EPIC) study. Am. J. Clin. Nutr. 2004, 80, 1012-1018.
24. Martin-Moreno, J.M.; Willett, W.C.; Gorgojo, L.; Banegas, J.R.; Rodriguez-Artalejo, F.; Fernandez-Rodriguez, J.C.; Maisonneuve, P.; Boyle, P. Dietary fat, olive oil intake and breast cancer risk. Int. J. Cancer 1994, 58, 774-780.
25. Covas, M.I.; Nyyssonen, K.; Poulsen, H.E.; Kaikkonen, J.; Zunft, H.J.; Kiesewetter, H.; Gaddi, A.; de la Torre, R.; Mursu, J.; Baumler, H.; Nascetti, S.; Salonen, J.T.; Fito, M.; Virtanen, J.; Marrugat, J.; Group, E.S. The effect of polyphenols in olive oil on heart disease risk factors: a randomized trial. Ann. Int. Med. 2006, 145, 333-341.
26. Nicolaiew, N.; Lemort, N.; Adorni, L.; Berra, B.; Montorfano, G.; Rapelli, S.; Cortesi, N.; Jacotot, B. Comparison between extra virgin olive oil and oleic acid rich sunflower oil: effects on postprandial lipemia and LDL susceptibility to oxidation. Ann. Nutr. Metab. 1998, 42, 251-260.
27. Carluccio, M.A.; Siculella, L.; Ancora, M.A.; Massaro, M.; Scoditti, E.; Storelli, C.; Visioli, F.; Distante, A.; De Caterina, R. Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: antiatherogenic properties of Mediterranean diet phytochemicals. Arterio. Throm. Vasc. Bio. 2003, 23, 622-629.
28. Tuck, K.L.; Hayball, P.J. Major phenolic compounds in olive oil: metabolism and health effects. J. Nutr. Biochem. 2002, 13, 636-644.
29. Visioli, F.; Caruso, D.; Galli, C.; Viappiani, S.; Galli, G.; Sala, A. Olive oils rich in natural catecholic phenols decrease isoprostane excretion in humans. Biochem. Biophys. Res. Comm. 2000, 278, 797-799.
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. 2000, 468, 159-160.
31. Bai, C.; Yan, X.; Takenaka, M.; Sekiya, K.; Nagata, T. Determination of synthetic hydroxytyrosol in rat plasma by GC-MS. J. Agric. Food Chem. 1998, 46, 3998-4001.
32. Vissers, M.N.; Zock, P.L.; Roodenburg, A.J.; Leenen, R.; Katan, M.B. Olive oil phenols are absorbed in humans. J. Nutr. 2002, 132, 409-417.
33. Miro Casas, E.; Albadalejo, M. F.; Covas Planells, M. I.; Colomer, F. M.; Lamuela Raventos, R. M.; de la Torre Fornell, R. Tyrosol bioavailability in humans after ingestion of virgin olive oil. Clin. Chem. 2001, 47, 341-343.
34. Bruni, N.; Cortesi, N.; Fiorino, P. Influence of agricultural techniques, cultivar and area of origin on characteristics of virgin olive oil and levels of some of its "minor" components. Olivae 1994, 1, 28-34.
35. Esti, M.; Cinquanta, L.; La Notte, E. Phenolic compounds in different olive varieties. J. Agric. Food Chem. 1998, 46, 32-35.
36. Gomez-Alonzo, S.; Salvador, M.D.; Fregapane, G. Phenolic compounds profile of Cornicarba virgin olive oil. J. Agric. Food Chem. 2002, 50, 6812-6817.
37. Vinha, A.F.; Ferreres, F.; Silva, B.M.; Valentao, P.; Goncalves, A.; Pereira, J.A.; Oliveira, M.B.; Seabra, R.M.; Andrade, P.B. Phenolic profiles of Portuguese olive fruits (Olea europaea L.): Influences of cultivar and geographical origin. Food Chem. 2005, 89, 561-568.
38. Cerretani, L.; Bendini, A.; Rotondi, A.; Lercker, G.; Toschi, T.G. Analytical comparison of monovarietal virgin olive oils obtained by both a continuous industrial plant and low-scale mill. Eur. J. Lipid Sci. Technol. 2005, 107, 93-100.
39. Sivakumar, G.; Bati, C.B.; Uccella, N. HPLC-MS screening of the antioxidant profile of Italian olive cultivars. Chem. Nat. Comp. 2005, 41, 588-591.
40. Franconi, F.; Coinu, R.; Carta, S.; Urgeghe, P.P.; Ieri, F.; Mulinacci, N.; Romani, A. Antioxidant effect of two virgin olive oils depends on the concentration and composition of minor polar compounds. J. Agric. Food Chem. 2006, 54, 3121-3125.
41. Carrasco Pancorbo, A.; Cruces-Blanco, C.; Segura Carretero, A.; Fernandez Gutierrez, A. Sensitive determination of phenolic acids in extra-virgin olive oil by capillary zone electrophoresis. J. Agric. Food Chem. 2004, 52, 6687-6693.
42. Caravaca, A.M.G.; Pancorbo, A.C.; Diaz, B.C.; Carretero, A.S.; Gutierrez, A.F. Electrophoretic identification and quantification of compounds in the polyphenolic fraction of extra-virgin olive oil. Electrophoresis 2005, 26, 3538-3551.
43. Romero, M.P.; Tovar, M.J.; Girona, J.; Motilva, M.J. Changes in the HPLC phenolic profile of virgin olive oil from young trees (Olea europaea L. Cv. Arbequina) grown under different deficit irrigation strategies. J. Agric. Food Chem. 2002, 50, 5349-5354.
44. Gomez-Rico, A.; Salvador, M.D.; La Greca, M.; Fregapane, G. Phenolic and volatile compounds of extra virgin olive oil (Olea europaea L. Cv. Cornicabra) with regard to fruit ripening and irrigation management. J. Agric. Food Chem. 2006, 54, 7130-7136.
45. Gimeno, E.; Castellote, A.I.; Lamuela-Raventos, R.M.; De la Torre, M.C.; Lopez-Sabater, M.C. The effects of harvest and extraction methods on the antioxidant content (phenolics, alphatocopherol, and beta-carotene) in virgin olive oil. Food Chem. 2002, 78, 207-211.
46. Brenes, M.; Garcia, A.; Garcia, P.; Rios, J.J.; Garrido, A. Phenolic compounds in Spanish olive oils. J. Agric. Food Chem. 1999, 47, 3535-3540.
47. Kalua, C.M.; Allen, M.S.; Bedgood, D.R., Jr.; Bishop, A.G.; Prenzler, P.D. Discrimination of olive oils and fruits into cultivars and maturity stages based on phenolic and volatile compounds. J. Agric. Food Chem. 2005, 53, 8054-8062.
48. Tovar, M.J.; Motilva, M.J.; Romero, M.P. Changes in the phenolic composition of virgin olive oil from young trees (Olea europaea L. cv. Arbequina) grown under linear irrigation strategies. J. Agric. Food Chem. 2001, 49, 5502-5508.
49. Ranalli, A.; Ferrante, M.L.; De Mattia, G.; Costantini, N. Analytical evaluation of virgin olive oil of first and second extraction. J. Agric. Food Chem. 1999, 47, 417-424.
50. Kalua, C.M.; Bedgood, D.R., Jr.; Bishop, A.G.; Prenzler, P.D. Changes in volatile and phenolic compounds with malaxation time and temperature during virgin olive oil production. J. Agric. Food Chem. 2006, 54, 7641-7651.
51. Mailer, R.J.; Ayton, J. Comparison of olive oil (Olea europaea) quality extracted by stonemill and hammermill. NZ. J. Crop Hort. Sci. 2004, 32, 325-330.
52. Fregapane, G.; Lavelli, V.; Leon, S.; Kapuralin, J.; Desamparados Salvador, M. Effect of filtration on virgin olive oil stability during storage. Eur. J. Lip. Sci. Technol. 2006, 108, 134-142.
53. Di Giovacchino, L.; Sestili, S.; Di Vincenzo, D. Influence of olive processing on virgin olive oil quality. Eur. J. Lip. Sci. Technol. 2002, 104, 587-601.
54. Brenes, M.; Garcia, A.; Garcia, P.; Garrido, A. Acid hydrolysis of secoiridoid aglycons during storage of virgin olive oil. J. Agric. Food Chem. 2001, 49, 5609-5614.
55. Gutierrez, F.; Fernandez, J.L. Determinant parameters and components in the storage of virgin olive oil. Prediction of storage time beyond which the oil is no longer of "extra" quality. J. Agric. Food Chem. 2002, 50, 571-577.
56. Okogeri, O.; Tasioula-Margari, M. Changes occurring in phenolic compounds and alphatocopherol of virgin olive oil during storage. J. Agric. Food Chem. 2002, 50, 1077-1080.
57. Rastrelli, L.; Passi, S.; Ippolito, F.; Vacca, G.; De Simone, F. Rate of degradation of alpha-tocopherol, squalene, phenolics, and polyunsaturated fatty acids in olive oil during different storage conditions. J. Agric. Food Chem. 2002, 50, 5566-5570.
58. Brenes, M.; Garcia, A.; Dobarganes, M.C.; Velasco, J.; Romero, C. Influence of thermal treatments simulating cooking processes on the polyphenol content in virgin olive oil. J. Agric. Food Chem. 2002, 50, 5962-5967.
59. Gomez-Alonso, S.; Fregapane, G.; Salvador, M.D.; Gordon, M.H. Changes in phenolic composition and antioxidant activity of virgin olive oil during frying. J. Agric. Food Chem. 2003, 51, 667-672.
60. Cicerale, S.; Conlan, X.A.; Barnett, N.W.; Sinclair, A.J.; Keast, R.S. Influence of heat on biological activity and concentration of oleocanthal - A natural anti-inflammatory agent in virgin olive oil. J. Agric. Food Chem. 2009, 57, 1326-1330.
61. Carrasco-Pancorbo, A.; Cerretani, L.; Bendini, A.; Segura-Carretero, A.; Gallina-Toschi, T.; Fernandez-Gutierez, A. Analytical determination of polyphenols in olive oils. J. Sep. Sci. 2005, 28, 837-858.
62. Cicerale, S.; Conlan, X.A.; Sinclair, A.J.; Keast, R.S.J. Chemistry and health of olive oil phenolics. Crit. Rev. Food Sci. Nutr. 2009, 49, 218-236.
63. Martini, F.H. Fundamentals of Anatomy and Physiology, 7 ed.; Pearson Education Inc.: San Francisco, CA, USA, 2006.
64. Visioli, F.; Galli, C.; Plasmati, E.; Viappiani, S.; Hernandez, A.; Colombo, C.; Sala, A. Olive phenol hydroxytyrosol prevents passive smoking-induced oxidative stress. Circulation 2000, 102, 2169-2171.
65. Caruso, D.; Visioli, F.; Patelli, R.; Galli, C.; Galli, G. Urinary excretion of olive oil phenols and their metabolites in humans. Metabolism 2001, 50, 1426-1428.
66. 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, after intravenous and oral dosing of labeled compounds to rats. J. Nutr. 2001, 131, 1993-1996.
67. Edgecombe, S.; Stretch, G.L.; Hayball, P.J. Oleuropein, an antioxidant polyphenol from olive oil, is poorly absorbed from isolated perfused rat intestine. J. Nutr. 2000, 130, 2996-3002.
68. Manna, C.; Galletti, P.; Maisto, G.; Cucciolla, V.; D'Angelo, S.; Zappia, V. Transport mechanism and metabolsi of olive oil hydroxytyrosol in Caco-2 cells. FEBS Letters 2000, 470, 341-344.
69. 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. 2001, 34, 301-305.
70. Fito, M.; Cladellas, M.; de la Torre, R.; Marti, J.; Munoz, D.; Schroder, H.; Alcantara, M.; Pujadas-Bastardes, M.; Marrugat, J.; Lopez-Sabater, M.C.; Bruguera, J.; Covas, M.I. Anti-inflammatory effect of virgin olive oil in stable coronary disease patients: a randomized, crossover, controlled trial. Eur. J. Clin. Nutr. 2008, 62, 570-574.
71. Ruano, J.; Lopez-Miranda, J.; de la Torre, R.; Delgado-Lista, J.; Fernandez, J.; Caballero, J.; Covas, M.I.; Jimenez, Y.; Perez-Martinez, P.; Marin, C.; Fuentes, F.; Perez-Jimenez, F. Intake of phenol-rich virgin olive oil improves the postprandial prothrombotic profile in hypercholesterolemic patients. Am. J. Clin. Nutr. 2007, 86, 341-346.
72. Gimeno, E.; de la Torre-Carbot, K.; Lamuela-Raventos, R.M.; Castellote, A.I.; Fito, M.; de la Torre, R.; Covas, M.I.; Carmen Lopez-Sabater, M. Changes in the phenolic content of low density lipoprotein after olive oil consumption in men. A randomized crossover controlled trial. Br. J. Nutr. 2007, 1-8.
73. Bogani, P.; Galli, C.; Villa, M.; Visioli, F. Postprandial anti-inflammatory and antioxidant effects of extra virgin olive oil. Atherosclerosis 2007, 190, 181-186.
74. Salvini, S.; Sera, F.; Caruso, D.; Giovannelli, L.; Visioli, F.; Saieva, C.; Masala, G.; Ceroti, M.; Giovacchini, V.; Pitozzi, V.; Galli, C.; Romani, A.; Mulinacci, N.; Bortolomeazzi, R.; Dolara, P.; Palli, D. Daily consumption of a high-phenol extra-virgin olive oil reduces oxidative DNA damage in postmenopausal women. Br. J. Nutr. 2006, 95, 742-751.
75. Covas, M.I.; de la Torre, K.; Farre-Albaladejo, M.; Kaikkonen, J.; Fito, M.; Lopez-Sabater, C.; Pujadas-Bastardes, M.A.; Joglar, J.; Weinbrenner, T.; Lamuela-Raventos, R.M.; de la Torre, R. Postprandial LDL phenolic content and LDL oxidation are modulated by olive oil phenolic compounds in humans. Free Rad. Biol. Med. 2006, 40, 608-616.
76. Ruano, J.; Lopez-Miranda, J.; Fuentes, F.; Moreno, J.A.; Bellido, C.; Perez-Martinez, P.; Lozano, A.; Gomez, P.; Jimenez, Y.; Perez Jimenez, F. Phenolic content of virgin olive oil improves ischemic reactive hyperemia in hypercholesterolemic patients. J. Am. Coll. Cardiol. 2005, 46, 1864-1868.
77. Visioli, F.; Caruso, D.; Grande, S.; Bosisio, R.; Villa, M.; Galli, G.; Sirtori, C.; Galli, C. Virgin Olive Oil Study (VOLOS): Vasoprotective potential of extra virgin olive oil in mildly dyslipidemic patients. Eur. J. Nutr. 2005, 44, 121-127.
78. Fito, M.; Cladellas, M.; de la Torre, R.; Marti, J.; Alcantara, M.; Pujadas-Bastardes, M.; Marrugat, J.; Bruguera, J.; Lopez-Sabater, M.C.; Vila, J.; Covas, M.I. Antioxidant effect of virgin olive oil in patients with stable coronary heart disease: a randomized, crossover, controlled, clinical trial. Atherosclerosis 2005, 181, 149-158.
79. Marrugat, J.; Covas, M.I.; Fito, M.; Schroder, H.; Miro-Casas, E.; Gimeno, E.; Lopez-Sabater, M.C.; de la Torre, R.; Farre, M. Effects of differing phenolic content in dietary olive oils on lipids and LDL oxidation - a randomized controlled trial. Eur. J. Nutr. 2004, 43, 140-147.
80. Weinbrenner, T.; Fito, 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.
81. Moschandreas, J.; Vissers, M.N.; Wiseman, S.; van Putte, K.P.; Kafatos, A. Extra virgin olive oil phenols and markers of oxidation in Greek smokers: a randomized cross-over study. Eur. J. Clin. Nutr. 2002, 56, 1024-1029.
82. Vissers, M.N.; Zock, P.L.; Wiseman, S.A.; Meyboom, S.; Katan, M B. Effect of phenol-rich extra virgin olive oil on markers of oxidation in healthy volunteers. Eur. J. Clin. Nutr. 2001, 55, 334-341.
83. Bonanome, A.; Pagnan, A.; Caruso, D.; Toia, A.; Xamin, A.; Fedeli, E.; Berra, B.; Zamburlini, A.; Ursini, F.; Galli, G. Evidence of postprandial absorption of olive oil phenols in humans. Nutr. Metab. Cardiovas. Dis. 2000, 10, 111-120.
84. Ramirez-Tortosa, M.C.; Urbano, G.; Lopez-Jurado, M.; Nestares, T.; Gomez, M.C.; Mir, A.; Ros, E.; Mataix, J.; Gil, A. Extra-virgin olive oil increases the resistance of LDL to oxidation more than refined olive oil in free-living men with peripheral vascular disease. J. Nutr. 1999, 129, 2177-2183.
85. Gordon, T.; Kannel, W.B.; Castelli, W.P.; Dawber, T.R. Lipoproteins, cardiovascular disease, and death. The Framingham study. Arch. Intern. Med. 1981, 141, 1128-1131.
86. Chrysohoou, C.; Pitsavos, C.; Skoumas, J.; Masoura, C.; Katinioti, A.; Panagiotakos, D.; Stefanadis, C. The emerging anti-inflammatory role of HDL-cholesterol, illustrated in cardiovascular disease free population; the ATTICA study. Int. J. Cardio. 2006, 122, 29-33.
87. Gimeno, E.; Fito, M.; Lamuela-Raventos, R.M.; Castellote, A.I.; Covas, M.; Farre, M.; de La Torre-Boronat, M.C.; Lopez-Sabater, M.C. Effect of ingestion of virgin olive oil on human lowdensity lipoprotein composition. Eur. J. Clin. Nutr. 2002, 56, 114-120.
88. Gorinstein, S.; Leontowicz, H.; Lojek, A.; Leontowicz, M.; Ciz, M.; Krzeminski, R.; Gralak, M.; Czerwinski, J.; Jastrzebski, Z.; Trakhtenberg, S.; Grigelmo-Miguel, N.; Soliva-Fortuny, R.; Martin-Belloso, O. Olive oils improve lipid metabolism and increase antioxidant potential in rats fed diets containing cholesterol. J. Agric. Food Chem. 2002, 50, 6102-6108.
89. Mangas-Cruz, M.A.; Fernandez-Moyano, A.; Albi, T.; Guinda, A.; Relimpio, F.; Lanzon, A.; Pereira, J.L.; Serrera, J.L.; Montilla, C.; Astorga, R.; Garcia-Luna, P.P. Effects of minor constituents (non-glyceride compounds) of virgin olive oil on plasma lipid concentrations in male Wistar rats. Clin. Nutr. 2001, 20, 211-215.
90. Witztum, J.L. The oxidation hypothesis of atherosclerosis. Lancet 1994, 344, 793-795.
91. Coni, E.; Di Benedetto, R.; Di Pasquale, M.; Masella, R.; Modesti, D.; Mattei, R.; Carlini, E.A. Protective effect of oleuropein, an olive oil biophenol, on low density lipoprotein oxidizability in rabbits. Lipids 2000, 35, 45-54.
92. Patrick, L.; Uzick, M. Cardiovascular disease: C-reactive protein and the inflammatory disease paradigm: HMG-CoA reductase inhibitors, alpha-tocopherol, red yeast rice, and olive oil polyphenols. A review of the literature. Altern. Med. Rev. 2001, 6, 248-271.
93. Ramirez-Tortosa, C.; Lopez-Pedrosa, J.M.; Suarez, A.; Ros, E.; Mataix, J.; Gil, A. Olive oil- and fish oil-enriched diets modify plasma lipids and susceptibility of LDL to oxidative modification in free-living male patients with peripheral vascular disease: the Spanish Nutrition Study. Br. J. Nutr. 1999, 82, 31-39.
94. Ochoa, J.J.; Quiles, J.L.; Ramirez-Tortosa, C.; Mataix, J.; Huertas, J.R. Dietary oil high in oleic acid but with different unsaponifiable fraction contents have different effects in fatty acid composition and peroxidation in rabit LDL. Nutrition 2002, 18, 60-65.
95. De la Torre-Carbot, K.; Chavez-Servin, J.L.; Jauregui, O.; Castellote, A.I.; Lamuela-Raventos, R.M.; Fito, M.; Covas, M.I.; Munoz-Aguayo, D.; Lopez-Sabater, M.C. Presence of virgin olive oil phenolic metabolites in human low density lipoprotein fraction: determination by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. Analyt. Chim. Acta 2007, 583, 402-410.
96. Berrougui, H.; Cloutier, M.; Isabelle, M.; Khalil, A. Phenolic-extract from argan oil (Argania spinosa L.) inhibits human low-density lipoprotein (LDL) oxidation and enhances cholesterol efflux from human THP-1 macrophages. Atherosclerosis 2006, 184, 389-396.
97. Masella, R.; Vari, R.; D'Archivio, M.; Di Benedetto, R.; Matarrese, P.; Malorni, W.; Scazzocchio, B.; Giovannini, C. Extra virgin olive oil biophenols inhibit cell-mediated oxidation of LDL by increasing the mRNA transcription of glutathione-related enzymes. J. Nutr. 2004, 134, 785-791.
98. Visioli, F.; Bellomo, G.; Montedoro, G.; Galli, C. Low density lipoprotein oxidation is inhibited in vitro by olive oil constituents. Atherosclerosis 1995, 117, 25-32.
99. Cooke, M.S.; Evans, M.D.; Dizdaroglu, M.; Lunec, J. Oxidative DNA damage: mechanisms, mutation, and disease. Fed. Am. Soc. Exper. Biol. J. 2003, 17, 1195-1214.
100. Machowetz, A.; Poulsen, H.E.; Gruendel, S.; Weimann, A.; Fito, M.; Marrugat, J.; de la Torre, R.; Salonen, J.T.; Nyyssonen, K.; Mursu, J.; Nascetti, S.; Gaddi, A.; Kiesewetter, H.; Baumler, H.; Selmi, H.; Kaikkonen, J.; Zunft, H.J.; Covas, M.I.; Koebnick, C. Effect of olive oils on biomarkers of oxidative DNA stress in Northern and Southern Europeans. FASEB J. 2007, 21, 45-52.
101. Jacomelli, M.; Pitozzi, V.; Zaid, M.; Larrosa, M.; Tonini, G.; Martini, A.; Urbani, S.; Taticchi, A.; Servili, M.; Dolara, P.; Giovannelli, L. Dietary extra-virgin olive oil rich in phenolic antioxidants and the aging process: long-term effects in the rat. J. Nutr. Biochem. 2009, doi:10.1016/j.jnutbio.2008.12.014.
102. Quiles, J.L.; Farquharson, A.J.; Simpson, D.K.; Grant, I.; Wahle, K.W. Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells. Br. J. Nutr. 2002, 88, 225-234.
103. Fabiani, R.; Rosignoli, P.; De Bartolomeo, A.; Fuccelli, R.; Servili, M.; Montedoro, G.F.; Morozzi, G. Oxidative DNA damage is prevented by extracts of olive oil, hydroxytyrosol, and other olive phenolic compounds in human blood mononuclear cells and HL60 cells. J. Nutr. 2008, 138, 1411-1416.
104. Reinisch, N.; Kiechl, S.; Mayr, C.; Schratzberger, P.; Dunzendorfer, S.; Kahler, C.M.; Buratti, T.; Willeit, J.; Wiedermann, C.J. Association of high plasma antioxidant capacity with new lesion formation in carotid atherosclerosis: a prospective study. Eur. J. Clin. Invest. 1998, 28, 787-792.
105. Goya, L.; Mateos, R.; Bravo, L. Effect of the olive oil phenol hydroxytyrosol on human hepatoma HepG2 cells: Protection against oxidative stress induced by tert-butylhydroperoxide. Eur. J. Nutr. 2007, 46, 70-78.
106. De la Puerta, R.; Martinez Dominguez, M.E.; Ruiz-Gutierrez, V.; Flavill, J.A.; Hoult, J.R. Effects of virgin olive oil phenolics on scavenging of reactive nitrogen species and upon nitrergic neurotransmission. Life Sci. 2001, 69, 1213-1222.
107. 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.
108. Paiva-Martins, F.; Fernandes, J.; Rocha, S.; Nascimento, H.; Vitorino, R.; Amado, F.; Borges, F.; Belo, L.; Santos-Silva, A. Effects of olive oil polyphenols on erythrocyte oxidative damage. Mol. Nutr. Food Res. 2009, 53, 609-616.
109. Moreno, J.J. Effect of olive oil minor components on oxidative stress and arachidonic acid mobilization and metabolism by macrophages. Free Rad. Biol. Med. 2003, 35, 1073-1081.
110. Biswas, S.K.; Newby, D.E.; Rahman, I.; Megson, I.L. Depressed glutathione synthesis precedes oxidative stress and atherogenesis in Apo-E(-/-) mice. Biochem. Biophys. Res. Comm. 2005, 338, 1368-1373.
111. Visioli, F.; Wolfram, R.; Richard, D.; Abdullah, M.I.C.B.; Crea, R. Olive phenolics increase glutathione levelsin healthy volunteers. J. Agric. Food Chem. 2009, 57, 1793-1796.
112. Loru, D.; Incani, A.; Deiaa, M.; Corona, G.; Atzeri, A.; Melis, M.P.; Rosa, A.; Dessi, M.A. Protective effect of hydroxytyrosol and tyrosol against oxidative stress in kidney cells. Toxicol. Ind. Health 2009, 25, 301-310.
113. Packard, R.R.S.; Libby, P. Inflammation in atherosclerosis: From vascular biology to biomarker discovery and risk prediction. Clin. Chem. 2008, 54, 24-38.
114. Groff, J.L.; Gropper, S.S. Advanced Nutrition and Human Metabolism, 3rd ed.; Wadsworth Thomson Learning: Belmont, CA, USA, 2000.
115. Tiziani, A. Harvard's Nursing Guide to Drugs; Elsevier Australia: Sydney, Australia, 2006.
116. Leger, C.L.; Carbonneau, M.A.; Michel, F.; Mas, E.; Monnier, L.; Cristol, J.P.; Descomps, B.A thromboxane effect of a hydroxytyrosol-rich olive oil wastewater extract in patients with uncomplicated type I diabetes. Eur. J. Clin. Nutr. 2005, 59, 727-730.
117. Beauchamp, G.K.; Keast, R.S.; Morel, D.; Lin, J.; Pika, J.; Han, Q.; Lee, C.H.; Smith, A.B.; Breslin, P.A. Phytochemistry: ibuprofen-like activity in extra-virgin olive oil. Nature 2005, 437, 45-46.
118. Brody, T. Nutritional Biochemistry, 2nd ed.; Academic Press: San Diego, CA, USA, 1999.
119. White, J.G. Platelets and atherosclerosis. Eur. J. Clin. Invest. 1994, 24 (Suppl 1), 25-29.
120. De La Cruz, J.P.; Villalobos, M.A.; Carmona, J.A.; Martin-Romero, M.; Smith-Agreda, J.M.; de la Cuesta, F.S. Antithrombotic potential of olive oil administration in rabbits with elevated cholesterol. Thromb. Res. 2000, 100, 305-315.
121. Perona, J.S.; Cabello-Moruno, R.; Ruiz-Gutierrez, V. The role of virgin olive oil components in the modulation of endothelial function. J. Nutr. Biochem. 2006, 17, 429-445.
122. Togna, G.I.; Togna, A.R.; Franconi, M.; Marra, C.; Guiso, M. Olive oil isochromans inhibit human platelet reactivity. J. Nutr. 2003, 133, 2532-2536.
123. Petroni, A.; Blasevich, M.; Salami, M.; Papini, N.; Montedoro, G.; Galli, C. Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil. Thromb. Res. 1995, 78, 151-160.
124. Dell' Agli, M.; Maschi, O.; Galli, G. V.; Fagnani, R.; Dal Cero, E.; Caruso, D.; Bosisio, E. Inhibition of platelet aggregation by olive oil phenols via cAMP-phosphodiesterase. Br. J. Nutr. 2008, 99, 945-951.
125. Manna, C.; Napoli, D.; Cacciapuoti, G.; Porcelli, M.; Zappia, V. Olive oil phenolic compounds inhibit homocysteine-induced endothelial cell adhesion regardless of their different antioxidant activity. J. Agric. Food Chem. 2009, 57, 3478-3482.
126. Evan, G.I.; Vousden, K.H. Proliferation, cell cycle and apoptosis in cancer. Nature 2001, 411, 342-348.
127. Fabiani, R.; De Bartolomeo, A.; Rosignoli, P.; Servili, M.; Selvaggini, R.; Montedoro, G.F.; Di Saverio, C.; Morozzi, G. Virgin olive oil phenols inhibit proliferation of human promyelocytic leukemia cells (HL60) by inducing apoptosis and differentiation. J. Nutr. 2006, 136, 614-619.
128. Gill, C.I.; Boyd, A.; McDermott, E.; McCann, M.; Servili, M.; Selvaggini, R.; Taticchi, A.; Esposto, S.; Montedoro, G.; McGlynn, H.; Rowland, I. Potential anti-cancer effects of virgin olive oil phenols on colorectal carcinogenesis models in vitro. Int. J. Cancer 2005, 117, 1-7.
129. Fini, L.; Hotchkiss, E.; Fogliano, V.; Graziani, G.; Romano, M.; De Vol, E.B.; Qin, H.; Selgrad, M.; Boland, C.R.; Ricciardiello, L. Chemopreventive properties of pinoresinol-rich olive oil involve a selective activation of the ATM-p53 cascade in colon cancer cell lines. Carcinogenesis 2008, 29, 139-146.
130. Hashim, Y.Z.; Rowland, I.R.; McGlynn, H.; Servili, M.; Selvaggini, R.; Taticchi, A.; Esposto, S.; Montedoro, G.; Kaisalo, L.; Wahala, K.; Gill, C.I. Inhibitory effects of olive oil phenolics on invasion in human colon adenocarcinoma cells in vitro. Int. J. Cancer 2008, 122, 495-500.
131. Corona, G.; Deiana, M.; Incani, A.; Vauzour, D.; Dessi, M.A.; Spencer, J.P.E. Hydroxytyrosol inhibits the proliferation of human colon adeocarcinoma cells through ihibition of ERK1/2 ad cyclin D1. Mol. Nutr. Food Res. 2009, 53, 897-903.
132. Menendez, J.A.; Vazquez-Martin, A.; Colomer, R.; Brunet, J.; Carrasco-Pancorbo, A.; Garcia-Villalba, R.; Fernandez-Gutierrez, A.; Segura-Carretero, A. Olive oil's bitter principle reverses acquired autoresistance to trastuzumab (Herceptin) in HER2-overexpressing breast cancer cells. BMC Cancer 2007, 7, 80-99.
133. Menendez, J.A.; Vazquez-Martin, A.; Oliveras-Ferraros, C.; Garcia-Villalba, R.; Carrasco Pancorbo, A.; Fernandez-Gutierez, A.; Segura-Carretero, A. Analysing effects of extra-virgin olive oil polyphenols on breast cancer-associated fatty acid synthase protein expression using reverse-phase protein microarrays. Int. J. Mol. Med. 2008, 22, 433-439.
134. Menendez, J.A.; Vazquez-Martin, A.; Oliveras-Ferraros, C.; Garcia-Villalba, R.; Carrasco Pancorbo, A.; Fernandez-Gutierrez, A.; Segura-Carretero, A. Extra-virgin olive oil polyphenolics inhibit HER2 (erbB-2)-induced malignant transformation in human breast epithelial cells: Relationship between the chemical structures of extra-virgin olive oil secoiridoids and lignans and their inhibitory activities on the tyrosine kinase activity of HER2. Int. J. Oncol. 2009, 34, 43-51.
135. Han, J.; Talorete, T.P.N.; Yamada, P.; Isoda, H. Anti-proliferative and apototic effects of oleuropein and hydroxytyrosol on human breast cancer MCF-7 cells. Cytotechnology 2009, 59, 45-53.
136. 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. 1997, 127, 286-292.
137. Li, W.; Sperry, J.B.; Crowe, A.; Trojanowki, J.Q.; Smith, A.B.; Lee, V.M.Y. Inhibition of tau fibrillization by oleocanthal via reaction with amino groups of tau. J. Neurochem. 2009, 110, 1339-1351.
138. Pitt, J.; Roth, W.; Lacor, P.; Blankenship, M.; Velasco, P.; De Felice, F.; Breslin, P.A.; Klein, W.L. Alzheimer's-associated A-beta oligomers show altered structure, immunoreactivity and synaptotoxicity with low doses of oleocanthal. Toxicol. Appl. Pharmacol. 2009, doi:10.1016/j.taap. 2009.07.018.
139. Gonzalez-Correa, J.A.; Navas, M.D.; Lopez-Villodres, J.A.; Trujillo, M.; Espartero, J.L.; De la Cruz, J.P. Neuroprotective effect of hydroxytyrosol and hydroxytyrosol acetate in rat brain slices subjected to hypoxia-reoxygeation. Neurosci. Lett. 2008, 446, 143-146.
140. Medina, E.; de Castro, A.; Romero, C.; Brenes, M. Comparison of the concentrations of phenolic compounds in olive oils and other plant oils: correlation with antimicrobial activity. J. Agric. Food Chem. 2006, 54, 4954-4961.
141. Romero, C.; Medina, E.; Vargas, J.; Brenes, M.; De Castro, A. In vitro activity of olive oil polyphenols against Helicobacter pylori. J. Agric. Food Chem. 2007, 55, 680-686.
142. Bisignano, G.; Tomaino, A.; Lo Cascio, R.; Crisafi, G.; Uccella, N.; Saija, A. On the in-vitro antimicrobial activity of oleuropein and hydroxytyrosol. J. Pharma. Pharmacol. 1999, 51, 971-974.
143. Puel, C.; Mardon, J.; Agalias, A.; Davicco, M.J.; Lebecque, P.; Mazur, A.; Horcajada, M.N.; Skaltsounis, A.L.; Coxam, V. Major phenolic compounds in olive oil modulate bone loss in an ovariectomy/inflammation experimental model. J. Agric. Food Chem. 2008, 56, 9417-9422.