Interactions between α-tocopherol and rosmarinic acid and its alkyl esters in emulsions: Synergistic, additive, or antagonistic effect?

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 41, 2012, Pages 10320-10330

  Panya, Atikorn ^a   Kittipongpittaya, Ketinun ^a   Laguerre, Mickaël ^b   Bayrasy, Christelle ^b   Lecomte, Jérôme ^b   Villeneuve, Pierre ^b   McClements, D Julian ^a   Decker, Eric A ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b CIRAD   (France)

Author keywords

tocopherol; emulsions; ester; rosmarinic acid

Indexed keywords

ALKYL ESTERS; ANTAGONISTIC EFFECTS; ANTAGONISTIC INTERACTIONS; ANTIOXIDANT ACTIVITIES; CAFFEIC ACIDS; FLUORESCENCE QUENCHING; INTERFACIAL REGION; LIPID OXIDATION; O/W EMULSIONS; OIL-IN-WATER EMULSIONS; OXIDATIVE STABILITY; ROSMARINIC ACID; SYNERGISTIC ACTIVITY; SYNERGISTIC INTERACTION;

AGENTS; EMULSIFICATION; EMULSIONS; ESTERS; MAGNETIC RESONANCE; OILS AND FATS; PARAMAGNETISM;

ESTERIFICATION;

ALPHA TOCOPHEROL; ANTIOXIDANT; CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; CINNAMIC ACID DERIVATIVE; DEPSIDE; ESTER; ROSMARINIC ACID;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; DRUG INTERACTION; DRUG POTENTIATION; ELECTRON SPIN RESONANCE; EMULSION; ESTERIFICATION; LIPID PEROXIDATION; SOYBEAN;

ALPHA-TOCOPHEROL; ANTIOXIDANTS; CAFFEIC ACIDS; CINNAMATES; DEPSIDES; DRUG ANTAGONISM; DRUG INTERACTIONS; DRUG SYNERGISM; ELECTRON SPIN RESONANCE SPECTROSCOPY; EMULSIONS; ESTERIFICATION; ESTERS; LIPID PEROXIDATION; SOYBEANS;

EID: 84867653125     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf302673j     Document Type: Article

References (47)

1. Gardner, H. W.; Kleiman, R.; Weisleder, D.; Inglett, G. E. Cysteine adds to lipid hydroperoxide Lipids 1977, 12 (8) 655-660
2. Lambelet, P. S., F.; Loliger, J Radical exchange reactions between vitamin E and vitamin C and phospholipids in autoxidizing polyunsaturated lipids Free Radical Res. 1994, 20 (1) 1-10
3. Sims, R. J.; Fioriti, J. A. Methional as an antioxidant for vegetable-oils J. Am. Oil Chem. Soc. 1977, 54 (1) 4-7
4. Terao, J.; Yamauchi, R.; Murakami, H.; Matsushita, S. Inhibitory effects of tocopherols and beta-carotene on singlet oxygen-initiated photo-oxidation of methyl linoleate and soybean oil J. Food Process. Preserv. 1980, 4 (1-2) 79-93
5. Burton, G. W.; Ingold, K. U. Beta-carotene - An unusual type of lipid antioxidant Science 1984, 224 (4649) 569-573
6. Kennedy, T. A.; Liebler, D. C. Peroxyl radical scavenging by beta-carotene in lipid bilayers-effect of oxygen partial-pressure J. Biol. Chem. 1992, 267 (7) 4658-4663
7. Palozza, P.; Krinsky, N. I. Beta-carotene and alpha-tocopherol are synergistic antioxidants Arch. Biochem. Biophys. 1992, 297 (1) 184-187
8. Parker, T. L.; Miller, S. A.; Myers, L. E.; Miguez, F. E.; Engeseth, N. J. Evaluation of synergistic antioxidant potential of complex mixtures using oxygen radical absorbance capacity (ORAC) and electron paramagnetic resonance (EPR) J. Agric. Food Chem. 2010, 58 (1) 209-217
9. Freeman, B. L.; Eggett, D. L.; Parker, T. L. Synergistic and Antagonistic Interactions of Phenolic Compounds Found in Navel Oranges J. Food Sci. 2010, 75 (6) C570-C576
10. Gonzalez, E. A.; Nazareno, M. A. Antiradical action of flavonoid-ascorbate mixtures LWT - Food Sci. Technol. 2011, 44 (2) 558-564
11. Liu, D. H.; Shi, J.; Ibarra, A. C.; Kakuda, Y.; Xue, S. J. The scavenging capacity and synergistic effects of lycopene, vitamin E, vitamin C, and beta-carotene mixtures on the DPPH free radical LWT - Food Sci. Technol. 2008, 41 (7) 1344-1349
12. Hidalgo, M.; Sanchez-Moreno, C.; de Pascual-Teresa, S. Flavonoid-flavonoid interaction and its effect on their antioxidant activity Food Chem. 2010, 121 (3) 691-696
13. Chen, J.; Shi, J.; Macnaughton, L.; Kakuda, Y.; Xue, S. J.; Ma, Y.; Zhang, M.; Jiang, Y. The scavenging capacity of combinations of lycopene, B-carotene, vitamin e, and vitamin c on the free radical 2,2-diphenyl-1- picrylhydrazyl (DPPH) J. Food Biochem. 2009, 33 (2) 232-245
14. Hiramoto, K.; Miura, Y.; Ohuki, G.; Kato, T.; Kikigawa, K. Are water-soluble natural antioxidants: synergistic in combination with alpha-tocopherol J. Oleo Sci. 2002, 51 (9) 569-576
15. Pedrielli, P.; Skibsted, L. H. Antioxidant synergy and regeneration effect of quercetin, (-)-epicatechin, and (+)-catechin on alpha-tocopherol in homogeneous solutions of peroxidating methyl linoleate J. Agric. Food Chem. 2002, 50 (24) 7138-7144
16. Alamed, J.; Chaiyasit, W.; McClements, D. J.; Decker, E. A. Relationships between Free Radical Scavenging and Antioxidant Activity in Foods J. Agric. Food Chem. 2009, 57 (7) 2969-2976
17. Fukuzawa, K.; Ikebata, W.; Sohmi, K. Location, antioxidant and recycling dynamics of alpha-tocopherol in liposome membranes J. Nutr. Sci. Vitaminol. 1993, 39, S9-S22
18. Lecomte, J.; Giraldo, L. J. L.; Laguerre, M.; Baréa, B.; Villeneuve, P. Synthesis, characterization and free radical scavenging properties of rosmarinic acid fatty esters J. Am. Oil Chem. Soc. 2010, 87 (6) 615-620
19. Waraho, T.; Cardenia, V.; Rodriguez-Estrada, M. T.; McClements, D. J.; Decker, E. A. Prooxidant mechanisms of free fatty acids in stripped soybean oil-in-water emulsions J. Agric. Food Chem. 2009, 57 (15) 7112-7117
20. Boon, C. S.; Xu, Z.; Yue, X.; McClements, D. J.; Weiss, J.; Decker, E. A. Factors affecting lycopene oxidation in oil-in-water emulsions J. Agric. Food Chem. 2008, 56 (4) 1408-1414
21. Faraji, H.; McClements, D. J.; Decker, E. A. Role of continuous phase protein on the oxidative stability of fish oil-in-water emulsions J. Agric. Food Chem. 2004, 52 (14) 4558-4564
22. Bligh, E. G.; Dyer, W. J. A rapid method of total lipid extraction and purification Can. J. Biochem. Physiol. 1959, 37 (8) 911-917
23. Panya, A.; Laguerre, M.; Lecomte, J.; Villeneuve, P.; Weiss, J.; McClements, D. J.; Decker, E. A. Effects of chitosan and rosmarinate esters on the physical and oxidative stability of liposomes J. Agric. Food Chem. 2010, 58 (9) 5679-5684
24. Fujimoto, A.; Masuda, T. Antioxidation mechanism of rosmarinic acid, identification of an unstable quinone derivative by the addition of odourless thiol Food Chem. 2012, 132 (2) 901-906
25. Wilson, G. J.; Lin, C. Y.; Webster, R. D. Significant differences in the electrochemical behavior of the α-, β-, and -tocopherols (Vitamin E) J. Phys. Chem. B 2006, 110 (23) 11540-11548
26. Pazos, M.; Torres, J. L.; Andersen, M. L.; Skibsted, L. H.; Medina, I. Galloylated polyphenols efficiently reduce alpha-tocopherol radicals in a phospholipid model system composed of sodium dodecyl sulfate (SDS) micelles J. Agric. Food Chem. 2009, 57 (11) 5042-8
27. Laguerre, M.; Lopez Giraldo, L. J.; Lecomte, J.; Figueroa-Espinoza, M. C.; Barea, B.; Weiss, J.; Decker, E. A.; Villeneuve, P. Relationship between hydrophobicity and antioxidant ability of "phenolipids" in emulsion: a parabolic effect of the chain length of rosmarinate esters J. Agric. Food Chem. 2010, 58 (5) 2869-2876
28. Panya, A.; Laguerre, M.; Bayrasy, C.; Lecomte, J.; Villeneuve, P.; McClements, D. J.; Decker, E. A. An Investigation of the Versatile Antioxidant Mechanisms of Action of Rosmarinate Alkyl Esters in Oil-in-Water Emulsions J. Agric. Food Chem. 2012, 60 (10) 2692-2700
29. Laguerre, M.; Giraldo, L. J.; Lecomte, J.; Figueroa-Espinoza, M. C.; Barea, B.; Weiss, J.; Decker, E. A.; Villeneuve, P. Chain length affects antioxidant properties of chlorogenate esters in emulsion: the cutoff theory behind the polar paradox J. Agric. Food Chem. 2009, 57 (23) 11335-11342
30. Buettner, G. R. The pecking order of free-radicals and antioxidants-lipid-peroxidation, alpha-tocopherol, and ascorbate Arch. Biochem. Biophys. 1993, 300 (2) 535-543
31. Hotta, H.; Ueda, M.; Nagano, S.; Tsujino, Y.; Koyama, J.; Osakai, T. Mechanistic study of the oxidation of caffeic acid by digital simulation of cyclic voltammograms Anal. Biochem. 2002, 303 (1) 66-72
32. Yang, B.; Kotani, A.; Arai, K.; Kusu, F. Estimation of the antioxidant activities of flavonoids from their oxidation potentials Anal. Sci. 2001, 17 (5) 599-604
33. Kilmartin, P. A.; Zou, H. L.; Waterhouse, A. L. A cyclic voltammetry method suitable for characterizing antioxidant properties of wine and wine phenolics J. Agric. Food Chem. 2001, 49 (4) 1957-1965
34. Gunckel, S.; Santander, P.; Cordano, G.; Ferreira, J.; Munoz, S.; Nunez-Vergara, L. J.; Squella, J. A. Antioxidant activity of gallates: an electrochemical study in aqueous media Chem.-Biol. Interact. 1998, 114 (1-2) 45-59
35. Firuzi, O.; Lacanna, A.; Petrucci, R.; Marrosu, G.; Saso, L. Evaluation of the antioxidant activity of flavonoids by ferric reducing antioxidant power assay and cyclic voltammetry Biochim. Biophys. Acta, Gen. Subj. 2005, 1721 (1-3) 174-184
36. Simic, A.; Manojlovic, D.; Segan, D.; Todorovic, M. Electrochemical Behavior and antioxidant and prooxidant activity of natural phenolics Molecules 2007, 12 (10) 2327-2340
37. Born, M.; Carrupt, P. A.; Zini, R.; Bree, F.; Tillement, J. P.; Hostettmann, K.; Testa, B. Electrochemical behaviour and antioxidant activity of some natural polyphenols Helv. Chim. Acta 1996, 79 (4) 1147-1158
38. Shahidi, F.; Zhong, Y. Revisiting the Polar Paradox Theory: A Critical Overview J. Agric. Food Chem. 2011, 59 (8) 3499-3504
39. Lopez-Giraldo, L. J.; Laguerre, M.; Lecomte, J.; Figueroa-Espinoza, M. C.; Barea, B.; Weiss, J.; Decker, E. A.; Villeneuve, P. Kinetic and stoichiometry of the reaction of chlorogenic acid and its alkyl esters against the DPPH radical J. Agric. Food Chem. 2009, 57 (3) 863-870
40. Kikuzaki, H.; Nakatani, N. Structure of a new antioxidative phenolic acid from oregano (origanum-vulgare L) Agric. Biol. Chem. 1989, 53 (2) 519-524
41. Nakazawa, T.; Ohsawa, K. Metabolism of rosmarinic acid in rats J. Nat. Prod. 1998, 61 (8) 993-996
42. Bel-Rhlid, R.; Crespy, V.; Page-Zoerkler, N.; Nagy, K.; Raab, T.; Hansen, C. E. Hydrolysis of Rosmarinic Acid from Rosemary Extract with Esterases and Lactobacillus johnsonii in Vitro and in a Gastrointestinal Model J. Agric. Food Chem. 2009, 57 (17) 7700-7705
43. Peyrat-Maillard, M. N.; Cuvelier, M. E.; Berset, C. Antioxidant activity of phenolic compounds in 2,2 azobis (2-amidinopropane) dihydrochloride (AAPH)-induced oxidation: Synergistic and antagonistic effects J. Am. Oil Chem. Soc. 2003, 80 (10) 1007-1012
44. Jung, D. M.; de Ropp, J. S.; Ebeler, S. E. Study of interactions between food phenolics and aromatic flavors using one- and two-dimensional H-1 NMR spectroscopy J. Agric. Food Chem. 2000, 48 (2) 407-412
45. Maccarone, E.; Maccarrone, A.; Rapisarda, P. Stabilization of anthocyanins of blood orange fruit juice J. Food Sci. 1985, 50 (4) 901-904
46. Foley, S.; Navaratnam, S.; McGarvey, D. J.; Land, E. J.; Truscott, T. G.; Rice-Evans, C. A. Singlet oxygen quenching and the redox properties of hydroxycinnamic acids Free Radical Biol. Med. 1999, 26 (9-10) 1202-1208
47. Chen, J. H.; Ho, C. T. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds J. Agric. Food Chem. 1997, 45 (7) 2374-2378