3784 J. Agric. Food Chem., Vol. 54, No. 11, 2006
Trujillo et al.
LITERATURE CITED
(22) Baldioli, M.; Servili, M.; Perretti, G.; Montedoro, G. F. Anti-
oxidant activity of tocopherol and phenolic compounds of virgin
olive oil. J. Am. Oil Chem. Soc. 1996, 73, 1589-1593.
(23) 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. 2001, 49, 2480-
2485.
(24) Mateos, R.; Dom´ınguez, M. M.; Espartero, J. L.; Cert, A.
Antioxidant effect of phenolic compounds, R-tocopherol, and
other minor components in virgin olive oil. J. Agric. Food Chem.
2003, 51, 7170-7175.
(25) Hudson, B. J. F., Ed. Food Antioxidants; Elsevier: London, 1990.
(26) Evans, R. J. Optimizing lipid stability with natural antioxidants.
In Natural Antioxidants, Chemistry, Health Effects and Applica-
tions; Shaidi, F., Ed.; AOCS Press: Champaign, IL, 1997; pp
224-244.
(27) Moure, A.; Cruz, J. M.; Franco, D.; Dom´ınguez, J. M.; Sineiro,
J.; Dom´ınguez, H.; Nu´n˜ez, M. J.; Parajo´, J. C. Natural antioxi-
dants from residual sources. Food Chem. 2001, 72, 145-171.
(28) Jin, G.; Yoshioka, H. Synthesis of lipophilic poly-lauroyl-(+)-
catechins and radical-scavenging activity. Biosci., Biotechnol.,
Biochem. 2005, 69, 440-447.
(1) Keys, A. Coronary heart disease in seven countries. Circulation
1970, 44, 163-175.
(2) Keys, A. Mediterranean diet and public health: personal reflec-
tions. Am. J. Clin. Nutr. 1995, 41, 1321S-1323S.
(3) Martin-Moreno, J. M.; Willett, W.; Gorgojo, L.; Benegas, J. R.;
Rodriguez-Artalejo, F.; Fernandez-Rodriguez, J. C.; Maison-
neuve, P.; Boyle, P. Dietary fat, olive oil intake, and breast cancer
risk. Int. J. Cancer 1994, 58, 774-780.
(4) Trichopoulou, A.; Katsouyanni, K.; Stuver, S.; Tzala, L.;
Gnardellis, C.; Rimm, E.; Trichopoulos, D. Consumption of olive
oil and specific food groups in relation to breast cancer risk in
Greece. J. Natl. Cancer Inst. 1995, 87, 110-116.
(5) 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.
(6) Lipworth, L.; Martinez, M. E.; Angell, J.; Hsieh, C. C.;
Trichopoulos, D. Olive oil and human cancer: an assessment
of evidence. PreV. Med. 1997, 26, 181-190.
(7) Willett, W. C. Specific fatty acids and risks of breast and prostate
cancer: dietary intake. Am. J. Clin. InVest. 1997, 66, 1557S-
1576S.
(8) Braga, C.; La Vecchia, C.; Franceschi, S.; Negri, E.; Parpinel,
M.; Decarli, A.; Giacosa, A.; Trichopoulos, D. Olive oil, other
seasoning fats, and the risk of colorectal carcinoma. Cancer 1998,
82, 448-453.
(9) Wiseman, S. A.; Mathot, J. N.; De Fouw, N. J.; Tijburg, L. B.
Dietary non-tocopherol antioxidants present in extra virgin olive
oil increase the resistance of low-density lipoproteins to oxidation
in rabbits. Atherosclerosis 1996, 120, 15-23.
(10) Bravo, L. Polyphenols: chemistry, dietary sources, metabolism,
and nutritional significance. Nutr. ReV. 1998, 56, 317-333.
(11) Tuck, K. L.; Hayball, P. J. Major phenolic compounds in olive
oil: metabolism and health effects. J. Nutr. Biochem. 2002, 13,
636-644.
(12) Visioli, F.; Galli, C. Olive oil phenols and their potential effects
on human health. J. Agric. Food Chem. 1998, 46, 4292-4296.
(13) Fito´, M.; Covas, M. I.; Lamuela-Ravento´s, R. M.; Vila, J.;
Torrents, J.; De la Torre, M. C.; Marrugat, J. Protective effect
of olive oil and its phenolic compounds against low density
lipoproteins oxidation. Lipids 2000, 35, 633-638.
(14) Visioli, F.; Galli, C.; Galli, G.; Caruso, D. Biological activities
and metabolic fate of olive oil phenols. Eur. J. Lipid Sci. Technol.
2002, 104, 677-684.
(15) Bisignano, G.; Tomaino, A.; Lo Cascio, R.; Crisafi, G.; Uccella,
N.; Saija, A. On the in vitro antimicrobial activity of oleuropein
and hydroxytyrosol. J. Pharm. Pharmacol. 1999, 51, 971-974.
(16) Furneri, P. M.; Piperno, A.; Sajia, A.; Bisignano, G. Antimy-
coplasmal activity of hydroxytyrosol. Antimicrob. Agents Chemoth-
er. 2004, 48, 4892-4894.
(17) Visioli, F.; Bellomo, G.; Montedoro, G. F.; Galli, C. Low-density
lipoprotein oxidation is inhibited in vitro by olive oil constituents.
Atherosclerosis 1995, 117, 25-32.
(18) Beauchamp G. K.; Keast, R. S. J.; Moresl, D.; Lin, J.; Pika, J.,
Han Q.; Lee, C.; Smith, A. B.; Breslin, P. A. S. Enzymes in an
inflammatory pathway are inhibited by oleocanthal, a component
of olive oil. Nature 2005, 437, 45-46.
(19) Kohyama, N.; Nagata, T.; Fujimoto, S. I.; Sekiya, K. Inhibition
of arachidonate lipoxygenase activities by 2-(3,4-dihydroxyphe-
nyl)ethanol, a phenolic compound from olives. Biosci., Biotech-
nol., Biochem. 1997, 61, 347-350.
(29) Cotelle, P.; Cotelle, N.; Teissier, E.; Vezin, H. Synthesis and
antioxidant properties of a new lipophilic ascorbic acid analogue.
Bioorg. Med. Chem. 2003, 11, 1087-1093.
(30) Ley, J. P.; Bertram, H. J. Synthesis of lipophilic clovamide
derivatives and their antioxidant potential against lipid peroxi-
dation. J. Agric. Food Chem. 2003, 51, 4596-4602.
(31) Servili, M.; Baldioli, M.; Miniati, E.; Montedoro, G. F. Anti-
oxidant activity of new phenolic compounds extracted from
virgin olive oil and their interaction with R-tocopherol and
â-carotene. RiV. Ital. Sostanze Grasse 1996, 73, 55-60.
(32) Gutie´rrez-Rosales, F.; R´ıos, J. J.; Go´mez-Rey, M. L. Main
polyphenols in the bitter taste of virgin olive oil. Structural
confirmation by on-line high performance liquid chromatography
electrospray ionization mass spectrometry. J. Agric. Food Chem.
2003, 51, 6021-6025.
(33) Mateos, R.; Cert, A.; Pe´rez-Camino, M. C.; Garc´ıa, J. M.
Evaluation of virgin olive oil bitterness by quantification of
secoiridoid derivatives. J. Am. Oil Chem. Soc. 2004, 81, 71-
75.
(34) Espartero, J. L.; Mateos, R.; Trujillo, M.; Cert, A.; Alcudia, F.
Structural characterization of new polyphenols in olive oil. In
Proceedings of the 27th Biennial Meeting of the Royal Spanish
Society of Chemistry, La Laguna, Spain, 1999; p 165.
(35) Brenes, M.; Garc´ıa, A.; Garc´ıa, P.; R´ıos, J. J.; Garrido, A.
Phenolic compounds in Spanish olive oils. J. Agric. Food Chem.
1999, 47, 3535-3540.
(36) Mateos, R.; Espartero, J. L.; Trujillo, M.; R´ıos, J. J.; Leo´n-
Camacho, M.; Alcudia, F.; Cert, A. Determination of phenols,
flavones, and lignans in virgin olive oils by solid-phase extraction
and high-performance liquid chromatography with diode array
ultraviolet detection. J. Agric. Food Chem. 2001, 49, 2185-
2192.
(37) Baraldi, P. G.; Simoni, D.; Manfredini, S.; Menziani, E.
Preparation of 3,4-dihydroxybenzeneethanol: A reinvestigation.
Liebigs Ann. Chem. 1983, 684-686.
(38) Buisman, G. J. H.; Helteren, C. T. W.; Kramer, G. F. H.;
Veldsink, J. W.; Derksen, J. T. P.; Cuperus, F. P. Enzymatic
esterifications of functionalized phenols for the synthesis of
lipophilic antioxidants. Biotechnol. Lett. 1998,20, 131-136.
(39) Alcudia, F.; Cert, A.; Espartero, J. L.; Mateos, R.; Trujillo, M.
Method of preparing hydroxytyrosol esters, esters thus obtained
and use of same. PCT WO 2004/005237, 2004.
(40) Torregiani, E.; Seu, G.; Minassi, A.; Appendino, G. Cerium-
(III) chloride-promoted chemoselective esterification of phenolic
alcohols. Tetrahedron Lett. 2005, 46, 2193-2196.
(20) De la Puerta, R.; Ru´ız-Gutie´rrez, V.; Hoult, J. R. S. Inhibition
of Leukocyte 5-lipoxygenase by phenolics from virgin olive oil.
Biochem. Pharmacol. 1999, 57, 445-449.
(21) Manna, C.; Della Ragione, F.; Cucciolla, V.; Borriello, A.;
D′Angelo, S.; Galletti, P.; Zappia, V. In AdVances in Nutrition
and Cancer 2; Zappia, V.; Della Ragione, F., Barbarisi, A.,
Russo, G. L., Dello Iacovo, R., Eds.; Kluwer: New York, 1999;
pp 115-130.
(41) Yoshida, H.; Kondo, I.; Kajimoto, G. Participation of free fatty
acids in the oxidation of purified soybean oil during microwave
heating. J. Am. Oil Chem. Soc. 1992, 69, 1136-1140.