Free radical-scavenging activity of nonenzymatically-browned phospholipids produced in the reaction between phosphatidylethanolamine and ribose in hydrophobic media

Food Chemistry

Volumn 124, Issue 4, 2011, Pages 1490-1495

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

^a INSTITUTO DE LA GRASA   (Spain)

Author keywords

Amino phospholipids; Carbonyl amine reactions; Free radical scavenging activity; Maillard reaction; Natural antioxidants; Nonenzymatic browning

Indexed keywords

[CARBONYL; AMINO PHOSPHOLIPIDS; MAILLARD REACTION; NATURAL ANTIOXIDANTS; NON-ENZYMATIC BROWNING;

AMINO ACIDS; CARBOHYDRATES; CARBONYLATION; FOOD PRODUCTS; HYDROPHOBICITY; PHOSPHOLIPIDS; VEGETABLE OILS;

FREE RADICALS;

ANTIOXIDANT; OLIVE OIL; PHOSPHATIDYLETHANOLAMINE; PHOSPHOLIPID; RIBOSE;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL REACTION KINETICS; FLUORESCENCE; GLYCATION; HYDROPHOBICITY; MASS FRAGMENTOGRAPHY;

EID: 77957020877     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2010.07.118     Document Type: Article

References (38)

1. Alaiz M., Hidalgo F.J., Zamora R. Antioxidative activity of nonenzymatically browned proteins produced in oxidized lipid/proteins reactions. Journal of Agricultural and Food Chemistry 1997, 45:1365-1369.
2. Alasalvar C., Shahidi F. Natural antioxidants in tree nuts. European Journal of Lipid Science and Technology 2009, 111:1056-1062.
3. American Oil Chemists' Society Official methods and recommended practices 1999, AOCS, Champaign, Illinois, [Method Ce 8-89]. 5th ed.
4. Bhushan S., Kalia K., Sharma M., Singh B., Ahuja P.S. Processing of apple pomace for bioactive molecules. Critical Reviews in Biotechnology 2008, 28:285-296.
5. Blois M.S. Antioxidant activity determination by the use of a stable free radical. Nature 1958, 181:1199-1200.
6. Chávez-Servín J.L., Castellote A.I., Martín M., Chifré R., López-Sabater M.C. Stability during storage of LC-PUFA-supplemented infant formula containing single cell oil or egg yolk. Food Chemistry 2009, 113:484-492.
7. Chawla S.P., Chander R., Sharma A. Antioxidant formation by γ-irradiation of glucose-amino acid model systems. Food Chemistry 2007, 103:1297-1304.
8. Chawla S.P., Chander R., Sharma A. Antioxidant properties of Maillard reaction products obtained by γ-irradiation of whey proteins. Food Chemistry 2009, 116:122-128.
9. Ebrahimzadeh M.A., Nabavi S.F., Nabavi S.M., Eslami B. Antihypoxic and antioxidant activity of Hibiscus esculentus seeds. Grasas Aceites 2010, 61:30-36.
10. Frankel E.N., Cooney P.M., Moser H.A., Cowan J.C., Evans C.D. Effect of antioxidants and metal inactivators in tocopherol-free soybean oil. Fette Seifen Anstrichmittel 1959, 61:1036-1039.
11. Frankel E.N., Finley J.W. How to standardize the multiplicity of methods to evaluate natural antioxidants. Journal of Agricultural and Food Chemistry 2008, 56:4901-4908.
12. Frankel E.N., Huang S.-W., Kanner J., German J.B. Interfacial phenomena in the evaluation of antioxidants: Bulk oils vs emulsions. Journal of Agricultural and Food Chemistry 1994, 42:1054-1059.
13. Goekmen V., Serpen A., Fogliano V. Direct measurement of the total antioxidant capacity of foods: The QUENCHER' approach. Trends in Food Science & Technology 2009, 20:278-288.
14. 13C NMR spectroscopy of lipids. Advances in lipid methodology-two 1993, 1-68. The Oily Press, Dundee, Scotland. W.W. Christie (Ed.).
15. Hidalgo F.J., Alaiz M., Zamora R. Pyrrolization and antioxidant function of proteins following oxidative stress. Chemical Research in Toxicology 2001, 14:582-588.
16. Hidalgo F.J., León M.M., Zamora R. 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 2006, 54:5461-5467.
17. Hidalgo F.J., León M.M., Zamora R. Effect of tocopherols in the antioxidative activity of oxidized lipid-amine reaction products. Journal of Agricultural and Food Chemistry 2007, 55:4436-4442.
18. Hidalgo F.J., León M.M., Zamora R. Effect of β-sitosterol in the antioxidative activity of oxidized lipid-amine reaction products. Food Research International 2009, 42:1215-1222.
19. Hidalgo F.J., Nogales F., Zamora R. Changes produced in the antioxidative activity of phospholipids as a consequence of their oxidation. Journal of Agricultural and Food Chemistry 2005, 53:659-662.
20. Hidalgo F.J., Nogales F., Zamora R. The role of amino phospholipids in the removal of the cito- and geno-toxic aldehydes produced during lipid oxidation. Food and Chemical Toxicology 2008, 46:43-48.
21. Hunter R.S. The measurement of appearance 1973, Hunter Associates Laboratory, Fairfax, VA.
22. Lederer M.O., Baumann M. Formation of a phospholipid-linked pyrrolecarbaldehyde from model reactions of d-glucose and 3-deoxyglucosone with phosphatidylethanolamine. Bioorganic & Medicinal Chemistry 2000, 8:115-121.
23. Madruga M.S., Elmore J.S., Dobson A.T., Mottram D.S. Volatile flavour profile of goat meat extracted by three widely used techniques. Food Chemistry 2009, 115:1081-1087.
24. Morales F.J., Jiménez-Pérez S. Free radical scavenging capacity of Maillard reaction products as related to color and fluorescence. Food Chemistry 2001, 72:119-125.
25. Morales F.J., Martin S., Acar O.C., Arribas-Lorenzo G., Goekmen V. Antioxidant activity of cookies and its relationship with heat-processing contaminants: A risk/benefit approach. European Food Research and Technology 2009, 228:345-354.
26. Nanditha B., Prabhasankar P. Antioxidants in bakery products: A review. Critical Reviews in Food Science and Nutrition 2009, 49:1-27.
27. Özen T. Antioxidant activity of wild edible plants in the Black Sea region of Turkey. Grasas Aceites 2010, 61:86-94.
28. Peralta E.M., Hatate H., Kawabe D., Kuwahara R., Wakamatsu S., Yuki T., et al. Improving antioxidant activity and nutritional components of Philippine salt-fermented shrimp paste through prolonged fermentation. Food Chemistry 2008, 111:72-77.
29. Pokorny J. Are natural antioxidants better-and safer-than synthetic antioxidants?. European Journal of Lipid Science and Technology 2007, 109:629-642.
30. 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. Journal of Agricultural and Food Chemistry 1989, 37:615-624.
31. Queiroz Y.S., Ishimoto E.Y., Bastos D.H.M., Sampaio G.R., Torres E.A.F.S. Garlic (Allium sativum L.) and ready-to-eat garlic products: In vitro antioxidant activity. Food Chemistry 2009, 115:371-374.
32. Requena J.R., Ahmed M.U., Fountain C.W., Degenhardt T.P., Reddy S., Perez C., et al. Carboxymethylethanolamine, a biomarker of phospholipid modification during the Maillard reaction in vivo. Journal of Biological Chemistry 1997, 272:17473-17479.
33. Snedecor G.W., Cochran W.G. Statistical methods 1980, Iowa State University Press, Ames, IA. 7th ed.
34. Solina M., Johnson R.L., Whitfield F.B. Effects of glucose and acid-hydrolysed vegetable protein on the volatile components of extruded wheat starch. Food Chemistry 2007, 100:678-692.
35. Zamora R., Hidalgo F.J. Phosphatidylethanolamine modification by oxidative stress product 4,5(E)-epoxy-2(E)-heptenal. Chemical Research in Toxicology 2003, 16:1632-1641.
36. Zamora R., Hidalgo F.J. 2-Alkylpyrrole formation from 4,5-epoxy-2-alkenals. Chemical Research in Toxicology 2005, 18:342-348.
37. 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.
38. Zamora R., Nogales F., Hidalgo F.J. Phospholipid oxidation and nonenzymatic browning development in phosphatidylethanolamine/ribose/lysine model systems. European Food Research and Technology 2005, 220:459-465.