Lipophilization of dihydrocaffeic acid affects its antioxidative properties in fish-oil-enriched emulsions

European Journal of Lipid Science and Technology

Volumn 114, Issue 2, 2012, Pages 134-145

  Sørensen, Ann Dorit Moltke ^a   Nielsen, Nina Skall ^a   Yang, Zhiyong ^b   Xu, Xuebing ^b   Jacobsen, Charlotte ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b AARHUS UNIVERSITY   (Denmark)

Author keywords

Caffeic acid; In vitro antioxidant assays; Lipid oxidation; O w Emulsion; Partitioning

Indexed keywords

EID: 84863115937     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201100002     Document Type: Article

References (33)

1. Jacobsen, C., Let, M. B., Nielsen, N. S., Meyer, A. S., Antioxidant strategies for preventing oxidative flavour deterioration of foods enriched with n-3 polyunsaturated lipids: A comparative evaluation. Trends Food Sci. Technol. 2008, 19, 76-93.
2. Rice-Evans, C. A., Miller, N. J., Paganga, G., Antioxidant properties of phenolic compounds. Trends Plant Sci. 1997, 2, 152-159.
3. Andjelkovic, M., Camp, J. V., Meulenaer, B. D., Depaemelaere, G., et al., Iron-chelation properties of phenolic acids bearing catechol and galloyl groups. Food Chem. 2006, 98, 23-31.
4. Chimi, H., Cillard, J., Rahmani, M., Peroxyl and hydroxyl radical scavenging activity of some natural phenolic antioxidants. J. Am. Oil Chem. Soc. 1991, 68, 307-312.
5. Nenadis, N., Zafiropoulou, I., Tsimidou, M., Commonly used food antioxidants: A comparative study in dispersed systems. Food Chem. 2003, 82, 403-407.
6. Nenadis, N., Boyle, S., Bakalbassis, E. G., Tsimidou, M., An experimental approach to structure-activity relationships of caffeic and dihydrocaffeic acids and related monophenols. J. Am. Oil Chem. Soc. 2003, 80, 451-458.
7. Pekkarinen, S. S., Stockmann, H., Schwarz, K., Heinonen, I. M., Hopia, A. I., Antioxidant activity and partitioning of phenolic acids in bulk and emulsified methyl linoleate. J. Agric. Food Chem. 1999, 47, 3036-3043.
8. Frankel, E. N., Huang, S.-W., Kanner, J., German, J. B., Interfacial phenomena in the evaluation of antioxidants: Bulk oils vs emulsions. J. Agric. Food Chem. 1994, 42, 1054-1059.
9. Porter, W. L., Paradoxical behavior of antioxidants in food and biological systems. Toxicol. Ind. Health 1993, 9, 93-122.
10. Sabally, K., Karboune, S., Yebaoh, F. K., Kermasha, S., Enzymatic esterification of dihydrocaffeic acid with linoleyl alcohol in organic solvent media. Biocatal. Biotransfor. 2005, 23, 37-44.
11. Silva, F. A. M., Borges, F., Guimaraes, C., Lima, J. L. F. C., et al., Phenolic acids and derivatives: Studies on the relationship among structure, radical scavenging activity, and physicochemical parameters. J. Agric. Food Chem. 2000, 48, 2122-2126.
12. Silva, F. A. M., Borges, F., Ferreira, M. A., Effects of phenolic propyl esters on the oxidative stability of refined sunflower oil. J. Agric. Food Chem. 2001, 49, 3936-3941.
13. Laguerre, M., Giraldo, L. J. L., Lecomte, J., Figueroa-Espinoza, M.-C., et al., Chain length affects antioxidant properties of chlorogenate esters in emulsion: The cutoff theory behind the polar paradox. J. Agric. Food Chem. 2009, 57, 11335-11342.
14. Yuji, H., Weiss, J., Villeneuve, P., Giraldo, L. J. L., et al., Ability of surface-active antioxidants to inhibit lipid oxidation in oil-in-water emulsion. J. Agric. Food Chem. 2007, 55, 11052-11056.
15. Laguerre, M., Giraldo, L. J. L., Lecomte, J., Figueroa-Espinoza, M.-C., et al., 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, 2869-2876.
16. Sabally, K., Karboune, S., Yeboah, F. K., Kermasha, S., Lipase-catalyzed esterification of selected phenolic acids with linolenyl alcohols in organic solvent media. Appl. Biochem. Biotechnol. 2005, 127, 17-27.
17. Rawle, A., Basic Principles of Particle Size Analysis, Malvern Instruments Ltd., Worcestershire, UK 1996.
18. Bligh, E. G., Dyer, W. J., A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 1959, 37, 911-917.
19. Iverson, S. J., Lang, S. L. C., Cooper, M. H., Comparision of the Bligh and Dyer and Folch methods for total lipid determination in broad range of marine tissue. Lipids 2001, 36, 1283-1287.
20. AOCS Official Method Ce 2-66. Preparation of Methyl Esters of Fatty Acids. Champaign, IL, USA, 1998.
21. AOCS Official Method Ce 1b-89. Fatty Acid Composition by GC. Marine Oils. Champaign, IL, USA, 1998.
22. Shantha, N. C., Decker, E. A., Rapid, sensitive, iron-based spectrophotometric methods for determination of peroxide values of food lipids. J. AOAC Int. 1994, 77, 421-424.
23. AOCS Official Method Ce 8-89. Determination of Tocopherols and Tocotrienols in Vegetable Oils and Fats by HPLC. Champaign, IL, USA, 1997.
24. Dinis, T. C. P., Madeira, V. M. C., Almeida, L. M., Action of phenolic derivatives (Acetaminophen, Salicylate, and 5-Aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch. Biochem. Biophys. 1994, 315, 161-169.
25. Yang, J., Guo, J., Yuan, J., In vitro antioxidant properties of rutin. LWT 2008, 41, 1060-1066.
26. Schwarz, K., Frankel, E. N., German, J. B., Partition behaviour of antioxidative phenolic compounds in heterophasic systems. Fett-Lipid 1996, 98, 115-121.
27. Sørensen, A.-D. M., Nielsen, N. S., Decker, E. A., Let, M. B., et al., The efficacy of compounds with different polarities as antioxidant in emulsions with fish oil. J. Am. Oil Chem. Soc. 2011, 88, 489-502.
28. Sabally, K., Karboune, S., St-Louis, R., Kermasha, S., Lipase-catalyzed synthesis of phenolic lipids from fish liver oil and dihydrocaffeic acid. Biocatal. Biotransfor. 2007, 25, 211-218.
29. Moon, J. H., Terao, J., Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein. J. Agric. Food Chem. 1998, 46, 5062-5065.
30. Sørensen, A.-D. M., Haahr, A.-M., Becker, E. M., Skibsted, L. H., et al., Interactions between iron, phenolic compounds, emulsifiers, and ph in omega-3-enriched oil-in-water emulsions. J. Agric. Food Chem. 2008, 56, 1740-1750.
31. Lue, B.-M., Nielsen, N. S., Jacobsen, C., Hellgren, L., et al., Antioxidant properties of modified rutin esters by DPPH, reducing power, iron chelation and low density lipoprotein assays. Food Chem. 2010, 123, 221-230.
32. Lue, B.-M., Enzymatic Lipophilization of Bioactive Compounds in Ionic Liquids; PhD Thesis, Department of Molecular Biology, Aarhus University, Denmark 2009.
33. Shahidi, F., Zhong, Y., Revisiting the polar paradox theory: A critical overview. J. Agric. Food Chem. 2011, 59, 3499-3504.