Article
J. Agric. Food Chem., Vol. 57, No. 20, 2009 9779
(5) Hsieh, R. J.; Kinsella, J. E. Oxidation of polyunsaturated fatty acids:
mechanisms, products, and inhibition with emphasis on fish. Adv.
Food Nutr. Res. 1989, 33, 233–341.
(6) Frankel, E. N. Lipid oxidation; Oily Press: Dundee, Scotland, 1998.
(7) Mcclements, D. J.; Decker, E. A. Lipid Oxidation in Oil-in-Water
Emulsions: Impact of Molecular Environment on Chemical Reac-
tions in Heterogeneous Food Systems. J. Food Sci. 2000, 65 (8),
1270–82.
(25) 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. 2007, 35 (2), 137–52.
(26) Huang, S. W.; Hopia, A.; Schwarz, K.; Frankel, E. N.; German,
J. B. Antioxidant activity of alpha-tocopherol and Trolox in differ-
ent lipid substrates: Bulk oils vs oil-in-water emulsions. J. Agric.
Food Chem. 1996, 44 (2), 444–52.
(8) Boyd, L. C.; Green, D. P.; Giesbrecht, F. B.; King, M. F. Inhibition
of oxidative rancidity in frozen cooked fish flakes by tert-butylhy-
droquinone and rosemary extract. J. Sci. Food Agric. 1993, 61 (1),
87–93.
(9) Frankel, E. N.; Huang, S.-W.; Kanner, J.; German, J. B. Interfacial
Phenomena in the Evaluation of Antioxidants: Bulk Oils vs Emul-
sions. J. Agric. Food Chem. 1994, 42 (5), 1054–9.
(27) Capasso, R.; Evidente, A.; Avolio, S.; Solla, F. A highly convenient
synthesis of hydroxytyrosol and its recovery from agricultural waste
waters. J. Agric. Food Chem. 1999, 47 (4), 1745–8.
(28) Huang, S.-W.; Frankel, E. N.; Schwarz, K.; Aeschbach, R.; German,
J. B. Antioxidant Activity of Carnosic Acid and Methyl Carnosate in
Bulk Oils and Oil-in-Water Emulsions. J. Agric. Food Chem. 1996, 44
(10), 2951–6.
(10) Chaiyasit, W.; Elias, R. J.; McClements, D. J.; Decker, E. A. Role of
physical structures in bulk oils on lipid oxidation. Cr. Rev. Food Sci.
Nutr. 2007, 47 (3), 299–317.
(29) Medina, I.; Tombo, I.; Satue-Gracia, M. T.; German, J. B.; Frankel,
E. N. Effects of natural phenolic compounds on the antioxidant
activity of lactoferrin in liposomes and oil-in-water emulsions.
J. Agric. Food Chem. 2002, 50 (8), 2392–9.
(30) Nenadis, N.; Tsimidou, M. Observations on the estimation of
scavenging activity of phenolic compounds using 1,1-diphenyl-2-
pycrylhydrazyl (DPPH) tests. J. Am. Oil Chem. Soc. 2002, 79.
(31) Tourino, S.; Selga, A.; Jimenez, A.; Julia, L.; Lozano, C.; Lizarraga,
D.; Cascante, M.; Torres, J. L. Procyanidin fractions from pine
(Pinus pinaster) bark: radical scavenging power in solution, anti-
oxidant activity in emulsion, and antiproliferative effect in melano-
ma cells. J. Agric. Food Chem. 2005, 53 (12), 4728–35.
(32) Benzie, I. F. F.; Strain, J. J. The ferric reducing ability of plasma
(FRAP) as a measure of “Antioxidant Power”: The FRAP assay.
Anal. Biochem. 1996, 239, 70–6.
(33) Ghose, A. K.; Crippen, G. M. Atomic physicochemical parameters
for three-dimensional-structure-directed quantitative structure-ac-
tivity relationships. 2. Modeling dispersive and hydrophobic inter-
actions. J. Chem. Inf. Comput. Sci. 1987, 27 (1), 21–35.
(11) 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 (5), 2480–5.
(12) Jimenez-Alvarez, D.; Giuffrida, F.; Golay, P. A.; Cotting, C.;
Lardeau, A.; Keely, B. J. Antioxidant activity of oregano, parsley,
and olive mill wastewaters in bulk oils and oil-in-water emulsions
enriched in fish oil. J. Agric. Food Chem. 2008, 56 (16), 7151–9.
(13) Sorensen, A. D.; Haahr, A. M.; Becker, E. M.; Skibsted, L. H.;
Bergenstahl, B.; Nilsson, L.; Jacobsen, C. Interactions between iron,
phenolic compounds, emulsifiers, and pH in omega-3-enriched oil-
in-water emulsions. J. Agric. Food Chem. 2008, 56 (5), 1740–50.
(14) Torres de Pinedo, A.; Penalver, P.; Morales, J. C. Synthesis and
evaluation of new phenolic-based antioxidants: structure-activity
relationship. Food Chem. 2007, 103, 55–61.
(15) Halliwell, B. Dietary polyphenols: Good, bad, or indifferent for your
health? Cardiovasc. Res. 2007, 73 (2), 341–7.
(16) Kris-Etherton, P. M.; Hecker, K. D.; Bonanome, A.; Coval, S. M.;
Binkoski, A. E.; Hilpert, K. F.; Griel, A. E.; Etherton, T. D.
Bioactive compounds in foods: their role in the prevention of cardio-
vascular disease and cancer. Am. J. Med. 2002, 113, (9, Suppl. 2),
71-88.
(34) Lu, Z.; Nie, G.; Belton, P. S.; Tang, H.; Zhao, B. Structure-activity
relationship analysis of antioxidant ability and neuroprotective
effect of gallic acid derivatives. Neurochem. Int. 2006, 48 (4), 263–74.
(35) Mateos, R.; Dominguez, M. M.; Espartero, J. L.; Cert, A. Anti-
oxidant effect of phenolic compounds, alpha-tocopherol, and other
minor components in virgin olive oil. J. Agric. Food Chem. 2003, 51
(24), 7170–5.
(36) Figueroa-Espinoza, M. C.; Villeneuve, P. Phenolic acids enzymatic
lipophilization. J. Agric. Food Chem. 2005, 53 (8), 2779–87.
(37) Nenadis, N.; Zhang, H. Y.; Tsimidou, M. Z. Structure-Antioxidant
Activity Relationship of Ferulic Acid Derivatives: Effect of Carbon
Side Chain Characteristic Groups. J. Agric. Food Chem. 2003, 51 (7),
1874–9.
(38) Kikuzaki, H.; Hisamoto, M.; Hirose, K.; Akiyama, K.; Taniguchi,
H. Antioxidant properties of ferulic acid and its related compounds.
J. Agric. Food Chem. 2002, 50 (7), 2161–8.
(39) Yuji, H.; Weiss, J.; Villeneuve, P.; Lopez Giraldo, L. J.; Figueroa-
Espinoza, M. C.; Decker, E. A. Ability of surface-active antioxidants
to inhibit lipid oxidation in oil-in-water emulsion. J. Agric. Food
Chem. 2007, 55 (26), 11052–6.
ꢀ
(17) Pazos, M.; Alonso, A.; Sanchez, I.; Medina, I. Hydroxytyrosol
Prevents Oxidative Deterioration in Foodstuffs Rich in Fish Lipids.
J. Agric. Food Chem. 2008, 56 (9), 3334–40.
(18) Visioli, F.; Bellomo, G.; Montedoro, G.; Galli, C. Low density
lipoprotein oxidation is inhibited in vitro by olive oil constituents.
Atherosclerosis 1995, 117 (1), 25–32.
(19) 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.
1995, 78 (2), 151–60.
(20) de la Puerta, R.; Ruiz Gutierrez, V.; Hoult, J. R. Inhibition of
leukocyte 5-lipoxygenase by phenolics from virgin olive oil. Biochem.
Pharmacol. 1999, 57 (4), 445–9.
(21) Owen, R. W.; Giacosa, A.; Hull, W. E.; Haubner, R.; Wurtele, G.;
Spiegelhalder, B.; Bartsch, H. Olive-oil consumption and health: the
possible role of antioxidants. Lancet Oncol 2000, 1, 107–12.
(40) Yu, C. A.; Gu, L. Q.; Lin, Y. Z.; Yu, L. Effect of alkyl side chain
variation on the electron-transfer activity of ubiquinone derivatives.
Biochemistry 1985, 24 (15), 3897–902.
(41) Pereira-Caro, G.; Madrona, A.; Bravo, L.; Espartero, J. L.; Alcudia,
F.; Cert, A.; Mateos, R. Antioxidant activity evaluation of alkyl
hydroxytyrosyl ethers, a new class of hydroxytyrosol derivatives.
Food Chem. 2009, 115 (1), 86–91.
(22) Torres de Pinedo, A.; Penalver, P.; Rondon, D.; Morales, J. C.
´
Efficient lipase-catalyzed synthesis of new antioxidants based on a
catechol structure. Tetrahedron 2005, 61, 7654–60.
(23) 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 ma-
trices and biological systems. J. Agric. Food Chem. 2006, 54 (11),
3779–85.
Received April 27, 2009. Revised manuscript received September 11,
2009. Accepted September 20, 2009. We would like to thank JAE-Doc
program (RL) and Intramural Frontier Project (200680F0132) from
CSIC for financial support.
(24) Torres de Pinedo, A.; Penalver, P.; Perez-Victoria, I.; Rondon, D.;
´ ´
Morales, J. C. Synthesis of new phenolic fatty acid esters and their
evaluation as lipophilic antioxidants in an oil matrix. Food Chem.
2007, 105, 657–65.