Antioxidative activity of amino phospholipids and phospholipid/amino acid mixtures in edible oils as determined by the rancimat method

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 15, 2006, Pages 5461-5467

  Hidalgo, Francisco J ^a   León, M Mercedes ^a   Zamora, Rosario ^a  

^a INSTITUTO DE LA GRASA   (Spain)

Author keywords

Amino carbonyl reactions; Food processing antioxidants; Lipid oxidation; Non enzymatic browning; Phospholipids; Pyrroles; Pyrrolized phospholipids; Rancimat

Indexed keywords

AMINO ACID; ANTIOXIDANT; BUTYLCRESOL; LYSINE; OLIVE OIL; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE; PHOSPHOLIPID; VEGETABLE OIL;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION;

AMINO ACIDS; ANTIOXIDANTS; BUTYLATED HYDROXYTOLUENE; LYSINE; OXIDATION-REDUCTION; PHOSPHATIDYLCHOLINES; PHOSPHATIDYLETHANOLAMINES; PHOSPHOLIPIDS; PLANT OILS;

IPS;

EID: 33746878176     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf060848s     Document Type: Article

References (48)

1. List, G. R.; Friedrich, J. P. Oxidative stability of seed oils extracted with supercritical carbon dioxide. J. Am. Oil Chem. Soc. 1989, 66, 98-101.
2. King, M. F.; Boyd, L. C.; Sheldon, B. W. Antioxidant properties of individual phospholipids in a salmon oil model system. J. Am. Oil Chem. Soc. 1992, 69, 545-551.
3. 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.
4. Judde, A.; Villeneuve, P.; Rossignol-Castera, A.; le Guillou, A. Antioxidant effect of soy lecithins on vegetable oil stability and their synergism with tocopherols. J. Am. Oil Chem. Soc. 2003, 80, 1209-1215.
5. Privett, O. S.; Quackenbush, F. W. Reaction of phosphoric acid in the autoxidation of fats. J. Am. Oil Chem. Soc. 1954, 31, 225-227.
6. Jewell, N. E.; Nawar, W. W. Thermal oxidation of phospholipids. 1,2-Dipalmitoyl-sn-glycerol-3-phosphoethanolamine. J. Am. Oil Chem. Soc. 1980, 57, 398-402.
7. Husain, S. R.; Terao, J.; Matsushita, S. Comparison of phosphatidylcholine and phosphatidylethanolamine affecting the browning reaction of heated oil. In Amino-Carbonyl Reactions in Food and Biological Systems; Fugimaki, M., Namiki, M., Kato, H., Eds.; Elsevier: New York, 1984; pp 301-309.
8. 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.
9. Hidalgo, F. J.; Nogales, F.; Zamora, R. Changes produced in the antioxidative activity of phospholipids as a consequence of their oxidation. J. Agric. Food Chem. 2005, 53, 659-662.
10. Alaiz, M.; Zamora, R.; Hidalgo, F. J. Antioxidative activity of pyrrole, imidazole, dihydropyridine, and pyridinium salt derivatives produced in oxidized lipid/amino acid browning reactions. J. Agric. Food Chem. 1996, 44, 686-691.
11. Zamora, R.; Alaiz, M.; Hidalgo, F. J. Feed-back inhibition of oxidative stress by oxidized lipid/amino acid reaction products. Biochemistry 1997, 36, 15765-15771.
12. Proestos, C.; Chorianopoulos, N.; Nychas, G. J. E.; Komaitis, M. RP-HPLC analysis of the phenolic compounds of plant extracts. Investigation of their antioxidant capacity and antimicrobial activity. J. Agric. Food Chem. 2005, 53, 1190-1195.
13. Jiabin, L.; Chang, S. K. C.; Wiesenborn, D. Antioxidant properties of soybean isoflavone extract and tofu in vitro and in vivo. J. Agric. Food Chem. 2005, 53, 2333-2340.
14. del Carlo, M.; Sacchetti, G.; di Mattia, C.; Compagnone, D.; Mastrocola, D.; Liberatore, L.; Cichelli, C. Contribution of the phenolic fraction to the antioxidant activity and oxidative stability of olive oil. J. Agric. Food Chem. 2005, 53, 4072-4079.
15. Mateos, R.; Trujillo, M.; Perez-Camino, M. C.; Moreda, W.; Cert, A. Relationships between oxidative stability, triacylglycerol composition, and antioxidant content in olive oil matrices. J. Agric. Food Chem. 2005, 53, 5766-5771.
16. Singleton, W. S.; Gray, M. S.; Brown, M. L.; White, J. L. Chromatographically homogeneous lecithin from egg phospholipids. J. Am. Oil Chem. Soc. 1965, 42, 53-56.
17. Zamora, R.; Hidalgo, F. J. Phosphatidylethanolamine modification by oxidative stress product 4,5(E)-epoxy-2(E)-heptenal. Chem. Res. Toxicol. 2003, 16, 1632-1641.
18. 13C NMR spectroscopy of lipids. In Advances in Lipid Methodology; Christie, W. W., Ed.; The Oily Press: Dundee, Scotland, 1993; Vol. 2, pp 1-68.
19. Zamora, R.; Olmo, C.; Navarro, J. L.; Hidalgo, F. J. Contribution of phospholipid pyrrolization to the color reversion produced during deodorization of poorly degummed vegetable oils. J. Agric. Food Chem. 2004, 52, 4166-4171.
20. Zamora, R.; Hidalgo, F. J. Reversion of Paal-Knorr synthesis: A new strategy for ring opening and N-substituent change in 1H-pyrroles. Synlett 2006, 1428-1430.
21. Zamora, R.; Hidalgo, F. J. 2-Alkylpyrrole formation, from 4,5-epoxy-2-alkenals. Chem. Res. Toxicol. 2005, 18, 342-348.
22. Francis, F. J.; Clydesdale, F. H. Food Colorimetry: Theory and Applications; AVI Publishing: Westport, CT, 1975.
23. Snedecor, G. W.; Cochran, W. G. Statistical Methods, 7th ed.; Iowa State University Press: Ames, IA, 1980.
24. Nawar, W. W. Lipids. In Food Chemistry, 3rd ed.; Fennema, O. R., Ed.; Dekker: New York, 1996; pp 225-319.
25. Hidalgo, F. J.; Zamora, R. Modification of bovine serum albumin structure following reaction with 4,5(E)-epoxy-2(E)-heptenal. Chem. Res. Toxicol. 2000, 13, 501-508.
26. Zamora, R.; Hidalgo, F. J. Comparative methyl linoleate and methyl linolenate oxidation in the presence of bovine serum albumin at several lipid/protein ratios. J. Agric. Food Chem. 2003, 51, 4661-4667.
27. Zamora, R.; Nogales, F.; Hidalgo, F. J. Phospholipid oxidation and nonenzymatic browning development in phosphatidylethanolamine/ribose/lysine model systems. Eur. Food Res. Technol. 2005, 220, 459-465.
28. Hidalgo, F. J.; Zamora, R. Strecker-type degradation produced by the lipid oxidation products 4,5-epoxy-2-alkenals. J. Agric. Food Chem. 2004, 52, 7126-7131.
29. Zamora, R.; Gallardo, E.; Hidalgo, F. J. Amine degradation by 4,5-epoxy-2-decenal in model systems. J. Agric. Food Chem. 2006, 54, 2398-2404.
30. Frankel, E. N. Lipid Oxidation, 2nd ed.; The Oily Press: Bridgwater, U.K., 2005.
31. Hidalgo, F. J.; Alaiz, M.; Zamora, R. A spectrophotometric method for the determination of proteins damaged by oxidized lipids. Anal. Biochem. 1998, 262, 129-136.
32. Hidalgo, F. J.; Nogales, F.; Zamora, R. Determination of pyrrolized phospholipids in oxidized phospholipid vesicles and lipoproteins. Anal. Biochem. 2004, 334, 155-163.
33. Hidalgo, F. J.; Alaiz, M.; Zamora, R. Determination of peptides and proteins in fats and oils. Anal. Chem. 2001, 73, 698-702.
34. Hidalgo, F. J.; Zamora, R. Peptides and proteins in edible oils: Stability, allergenicity, and new processing trends. Trends Food Sci. Technol. 2006, 17, 56-63.
35. Hidalgo, F. J.; Zamora, R. Fluorescent pyrrole products from carbonyl-amine reactions. J. Biol. Chem. 1993, 268, 16190-16197.
36. Zamora, R.; Alaiz, M.; Hidalgo, F. J. Contribution of pyrrole formation and polymerization to the nonenzymatic browning produced by amino-carbonyl reactions. J. Agric. Food Chem. 2000, 48, 3152-3158.
37. Hidalgo, F. J.; Nogales, F.; Zamora, R. Nonenzymatic browning, fluorescence development, and formation of pyrrole derivatives in phosphatidylethanolamine/ribose/lysine model systems. J. Food Sci. 2005, 70, C387-C391.
38. Min, D. B.; Boff, J. M. Lipid oxidation of edible oil. In Food Lipids: Chemistry, Nutrition, and Biotechnology, 2nd ed.; Akoh, C. C., Min, D. B., Eds.; Marcel Dekker: New York, 2002; pp 335-363.
39. Erickson, M. C. Lipid oxidation of muscle foods. In Food Lipids: Chemistry, Nutrition, and Biotechnology, 2nd ed.; Akoh, C. C., Min, D. B., Eds.; Marcel Dekker: New York, 2002; pp 365-411.
40. Reische, D. W.; Lillard, D. A.; Eitenmiller, R. R. Antioxidants. In Food Lipids: Chemistry, Nutrition, and Biotechnology, 2nd ed.; Akoh, C. C., Min, D. B., Eds.; Marcel Dekker: New York, 2002; pp 489-516.
41. Frankel, E. N. In search of better methods to evaluate natural antioxidants and oxidative stability in food lipids. Trends Food Sci. Technol. 1993, 4, 220-225.
42. Alaiz, M.; Zamora, R.; Hidalgo, F. J. Natural antioxidants produced in oxidized lipid/amino acid browning reactions. J. Am. Oil Chem. Soc. 1995, 72, 1571-1575.
43. Alaiz, M.; Hidalgo, F. J.; Zamora, R. Effect of pH and temperature on comparative antioxidant activity of nonenzymatically browned proteins produced by reaction with oxidized lipids and carbohydrates. J. Agric. Food Chem. 1999, 47, 748-752.
44. Alaiz, M.; Hidalgo, F. J.; Zamora, R. Antioxidative activity of nonenzymatically browned proteins produced in oxidized lipid/protein reactions. J. Agric. Food Chem. 1997, 45, 1365-1369.
45. Alaiz, M.; Hidalgo, F. J.; Zamora, R. Comparative antioxidant activity of Maillard- and oxidized lipid-damaged bovine serum albumin. J. Agric. Food Chem. 1997, 45, 3250-3254.
46. Velasco, J.; Dobarganes, C. Oxidative stability of virgin olive oil. Eur. J. Lipid Sci. Technol. 2002, 104, 661-676.
47. 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.
48. Huang, S.-W.; Frankel, E. N.; German, J. B. Antioxidant activity of α- and γ-tocopherols in bulk oils and in oil-in-water emulsions. J. Agric. Food Chem. 1994, 42, 2108-2114.