Antioxidant properties of chlorogenic acid and its alkyl esters in stripped corn oil in combination with phospholipids and/or water

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 18, 2011, Pages 10361-10366

  Laguerre, Mickaël ^a   Chen, Bingcan ^a   Lecomte, Jérôme ^b   Villeneuve, Pierre ^b   McClements, D Julian ^a   Decker, Eric A ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b UMR IATE   (France)

Author keywords

antioxidant; chlorogenic acid; conjugated diene; corn oil; hexanal; lipid oxidation; polar paradox

Indexed keywords

ANTIOXIDANT; CHLOROGENIC ACID; CONJUGATED DIENE; CORN OIL; HEXANAL; LIPID OXIDATION; POLAR PARADOX;

AGENTS; ESTERIFICATION; ESTERS; HYDROPHOBICITY; OLEFINS; PHOSPHOLIPIDS; VEGETABLE OILS;

PHENOLS;

ANTIOXIDANT; CHLOROGENIC ACID; CORN OIL; ESTER; PHENOL DERIVATIVE; PHOSPHOLIPID; WATER;

ARTICLE; CHEMICAL PHENOMENA; CHEMISTRY;

ANTIOXIDANTS; CHLOROGENIC ACID; CORN OIL; ESTERS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; PHENOLS; PHOSPHOLIPIDS; WATER;

ZEA MAYS;

EID: 80053125161     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2026742     Document Type: Article

References (28)

1. Sherwin, E. R. Antioxidants for vegetable oils J. Am. Oil Chem. Soc. 1976, 53, 430-436
2. Porter, W. L. Recent trends in food applications of antioxidants. In Autoxidation in Food and Biological Systems; Simic, M. G.; Karel, M., Eds.; Plenum Press: New York, 1980; pp 295-365.
3. Porter, W. L.; Black, E. D.; Drolet, A. M. Use of polyamide oxidative fluorescence test on lipid emulsions: contrast in relative effectiveness of antioxidants in bulk versus dispersed systems J. Agric. Food Chem. 1989, 37, 615-624
4. Porter, W. L. Paradoxical behavior of antioxidants in food and biological systems. In Antioxidants: Chemical, Physiological, Nutritional and Toxicological Aspects; Williams, G. M., Ed.; Princeton Scientific: Princeton, NJ, 1993; pp 93-122. (Pubitemid 23216383)
5. Frankel, E. N.; Huang, S.-W.; Kanner, J.; German, J. B. Interfacial phenomena in the evaluation of antioxidants: bulk oils vs emulsion J. Agric. Food Chem. 1994, 42, 1054-1059
6. Chaiyasit, C.; Elias, R. J.; McClements, D. J.; Decker, E. A. Role of physical structures in bulk oils on lipid oxidation Crit. Rev. Food Sci. Nutr. 2007, 47, 299-317 (Pubitemid 46447837)
7. Koga, T.; Terao, J. Phospholipids increase radical-scavenging activity of vitamin E in a bulk oil model system J. Agric. Food Chem. 1995, 43, 1450-1454
8. 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
9. Shahidi, F.; Zhong, Y. Revisiting the polar paradox theory: a critical overview J. Agric. Food Chem. 2011, 59, 3499-3504
10. Laguerre, M.; López-Giraldo, L. J.; Lecomte, J.; Baréa, B.; Cambon, E.; Tchobo, P. F.; Barouh, N.; Villeneuve, P. Conjugated autoxidizable triene (CAT) assay: a novel spectrophotometric method for determination of antioxidant capacity using triacylglycerol as ultraviolet probe Anal. Biochem. 2008, 380, 282-290
11. Laguerre, M.; López 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 cut-off theory behind the polar paradox J. Agric. Food Chem. 2009, 57, 11335-11342
12. Sasaki, K.; Alamed, J.; Weiss, J.; Villeneuve, P.; Lopez Giraldo, L. J.; Lecomte, J.; Figueroa-Espinoza, M. C.; Decker, E. A. Relationship between the physical properties of chlorogenic acid esters and their ability to inhibit lipid oxidation in oil-in-water emulsions Food Chem. 2010, 118, 830-835
13. López Giraldo, L. J.; Laguerre, M.; Lecomte, J.; Figueroa-Espinoza, M. C.; Baréa, 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, 863-870
14. Laguerre, M.; Wrutniak-Cabello, C.; Chabi, B.; López Giraldo, L. J.; Lecomte, J.; Villeneuve, P.; Cabello, G. Does hydrophobicity always enhance antioxidant drugs? A cut-off effect of the chain length of functionalized chlorogenate esters on ROS-overexpressing fibroblasts J. Pharm. Pharmacol. 2011, 63, 531-540
15. López Giraldo, L. J.; Laguerre, M.; Lecomte, J.; Figueroa-Espinoza, M.-C.; Barouh, N.; Barea, B.; Villeneuve, P. Lipase-catalysed synthesis of chlorogenate fatty esters in solvent-free medium Enzyme Microb. Technol. 2007, 41, 721-726 (Pubitemid 47371025)
16. Boon, C. S.; Xu, Z.; Yue, X.; McClements, D. J.; Weiss, J.; Decker, E. A. Factor affecting lycopene oxidation in oil-in-water emulsions J. Agric. Food Chem. 2008, 56, 1408-1414 (Pubitemid 351364076)
17. Kanamoto, R.; Wada, Y.; Miyajima, G.; Kito, M. Phospholipid-phospholipid interaction in soybean oil J. Am. Oil Chem. Soc. 1981, 58, 1050-1053
18. Chan, H. W.-S.; Levett, G. Autoxidation of methyl linoleate. Separation and analysis of isomeric mixtures of methyl linoleate hydroperoxides and methyl hydroxylinoleates Lipids 1977, 12, 99-104 (Pubitemid 8036650)
19. Felgner, A.; Schlink, R.; Kirschenbühler, P.; Faas, B.; Isengard, H.-D. Automated Karl Fischer titration for liquid samples - water determination in edible oils Food Chem. 2008, 106, 1379-1384 (Pubitemid 350011015)
20. Chen, B.; Han, A.; McClements, D. J.; Decker, E. A. Physical structures in soybean oil and their impact on lipid oxidation J. Agric. Food Chem. 2010, 58, 11993-11999
21. Xenakis, A.; Papadimitriou, V.; Sotiroudis, T. G. Colloidal structures in natural oils Curr. Opin. Colloid Interface Sci. 2010, 15, 55-60
22. Luisi, P. L.; Straub, B. Reverse Micelles. Biological and Technological Relevance of Amphilic Structures in Apolar Media; Plenum Press: London, U.K., 1984.
23. Pileni, M. P. In Structure and Reactivity in Reverse Micelles; Pileni, M. P., Ed.; Elsevier: New York, 1989.
24. McClements, D. J. Food Emulsions: Principles, Practices, and Techniques, 2nd ed.; CRC Press: Boca Raton, FL, 2004.
25. Gupta, R.; Muralidhara, H. S.; Davies, H. T. Structure and phase behavior of phospholipids-based micelles in nonaqueous media Langmuir 2001, 17, 5176-5183 (Pubitemid 35330820)
26. Subramanian, R.; Ichikawa, S.; Nakajima, M.; Kimura, T.; Maekawa, T. Characterization of phospholipids reverse micelles in relation to membrane processing of vegetable oils Eur. J. Lipid Sci. Technol. 2001, 103, 93-97
27. Laguerre, M.; Lecomte, J.; Villeneuve, P. Evaluation of the ability of antioxidants to counteract lipid oxidation: existing methods, new trends and challenges Prog. Lipid Res. 2007, 46, 244-282 (Pubitemid 47103214)
28. Laguerre, M.; Decker, E. A.; Lecomte, J.; Villeneuve, P. Methods for evaluating potency and efficacy of antioxidants Curr. Opin. Clin. Nutr. Metab. Care 2010, 13, 518-525