The effects of acyl moiety and temperature on the polymerization of sterols

European Journal of Lipid Science and Technology

Volumn 114, Issue 6, 2012, Pages 677-686

  Lehtonen, Mari ^a   Lampi, Anna Maija ^a   Agalga, Flora ^a   Struijs, Karin ^a,b   Piironen, Vieno ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b GHENT UNIVERSITY   (Belgium)

Author keywords

Autoxidation; CIS MS; Oligomer; Polymerization; Sterol; Steryl ester

Indexed keywords

EID: 84862191697     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201100305     Document Type: Article

References (28)

1. Porter, N. A., Caldwell, S. E., Mills, K. A., Mechanisms of free radical oxidation of unsaturated lipids. Lipids 1995, 30, 277- 289.
2. Schaich, K. M., in: Shahidi, F. (Ed.), Bailey's Industrial Oil and Fat Products, 6th Edn., John Wiley & Sons, Inc., Hoboken, NJ (USA) 2005, pp. 269- 354.
3. Kamal-Eldin, A., Min, D. B., Lipid Oxidation Pathways, AOCS Press, Urbana, IL (USA) 2008.
4. Miyashita, K., Fujimoto, K., Kaneda, T., Formation of dimers during the initial stage of autoxidation in methyl linoleate. Agric. Biol. Chem. 1982, 46, 751- 755.
5. Miyashita, K., Fujimoto, K., Kaneda, T., Structures of dimers produced from methyl linoleate during initial stage of autoxidation. Agric. Biol. Chem. 1982, 46, 2293- 2297.
6. Blekas, G., Boskou, D., in: Boskou, D., Elmadfa, I. (Eds.), Frying of Food Oxidation, Nutrient and Non-nutrient Antioxidants, Biologically Active Compounds and High Temperatures, Technomic Publishing Company, Inc., Lancaster, PA (USA) 1999, pp. 205- 221.
7. Donner, M. G., Richter, W. O., 3rd International symposium on deep-fat frying-optimal operation. Eur. J. Lipid Sci. Technol. 2000, 102, 306- 308.
8. Lampi, A.-M., Kemmo, S., Mäkelä, A., Heikkinen, S., Piironen, V., Distribution of monomeric, dimeric and polymeric products of stigmasterol during thermo-oxidation. Eur. J. Lipid. Sci. Technol. 2009, 111, 1027- 1034.
9. Struijs, K., Lampi, A.-M., Ollilainen, V., Piironen, V., Dimer formation during the thermo-oxidation of stigmasterol. Eur. Food Res. Technol. 2010, 231, 853- 863.
10. Rudzinska, M., Przybylski, R., Zhao, Y., Curtis, J., Sitosterol thermo-oxidative degradation leads to the formation of dimers, trimers and oligomers: A study using combined size exclusion chromatography/mass spectrometry. Lipids 2010, 45, 549- 558.
11. Billek, G., Health aspects of thermoxidized oils and fats. Eur. J. Lipid Sci. Technol. 2000, 102, 587- 593.
12. Omwamba, M., Artz, W., Mahungu, S., in: Boskou, D., Elmadfa, I. (Eds.), Frying of Food: Oxidation, Nutrient and Non-nutrient Antioxidants, Biologically Active Compounds and High Temperatures, 2nd Edn., CRC Press, Boca Raton, FL (USA) 2010, pp. 23- 47.
13. Gertz, C., Kochhar, P., A new method to determine oxidative stability of vegetable fats and oils at simulated frying temperature. OCL-Ol. Corps Gras. Li. 2001, 8, 82- 88.
14. Márquez-Ruiz, G., Tasioula-Margari, M., Dobarganes, M., Quantitation and distribution of altered fatty acids in frying fats. J. Am. Oil Chem. Soc. 1995, 72, 1171- 1176.
15. Kim, S., Nawar, W., Parameters influencing cholesterol oxidation. Lipids 1993, 28, 917- 922.
16. Soupas, L., Huikko, L., Lampi, A.-M., Piironen, V., Esterification affects phytosterol oxidation. Eur. J. Lipid Sci. Technol. 2005, 107, 107- 118.
17. Lehtonen, M., Kemmo, S., Lampi, A.-M., Piironen, V., Effects of esterification on the formation and decomposition of steryl hydroperoxides. Eur. Food Res. Technol. 2011, 232, 255- 264.
18. Lehtonen, M., Lampi, A.-M., Ollilainen, V., Struijs, K., Piironen, V., The role of acyl moiety in the formation and reactions of steryl ester hydroperoxides. Eur. Food Res. Technol. 2011, 233, 51- 61.
19. Soupas, L., Juntunen, L., Säynäjoki, S., Lampi, A.-M., Piironen, V., GC-MS method for characterization and quantification of sitostanol oxidation products. J. Am. Oil Chem. Soc. 2004, 81, 135- 141.
20. Lampi, A.-M., Juntunen, L., Toivo, J., Piironen, V., Determination of thermo-oxidation products of plant sterols. J. Chromatogr. B 2002, 777, 83- 92.
21. Márquez-Ruiz, G., Holgado, F., García-Martínez, M. C., Dobarganes, M. C., A direct and fast method to monitor lipid oxidation progress in model fatty acid methyl esters by high-performance size-exclusion chromatography. J. Chromatogr. A 2007, 1165, 122- 127.
22. Kamal-Eldin, A., Velasco, J., Dobarganes, C., Oxidation of mixtures of triolein and trilinolein at elevated temperatures. Eur. J. Lipid Sci. Technol. 2003, 105, 165- 170.
23. Seal, J. R., Havrilla, C. M., Porter, N. A., Hachey, D. L., Analysis of unsaturated compounds by Ag+ coordination ionspray mass spectrometry: Studies of the formation of the Ag+/lipid complex. J. Am. Soc. Mass Spectrosc. 2003, 14, 872- 880.
24. Havrilla, C. M., Hachey, D. L., Porter, N. A., Coordination (Ag) ion spray-mass spectrometry of peroxidation products of cholesterol linoleate and cholesterol arachidonate: High-performance liquid chromatography-mass spectrometry analysis of peroxide products from polyunsaturated lipid autoxidation. J. Am. Chem Soc. 2000, 122, 8042- 8055.
25. Seal, J. R., Porter, N. A., Liquid chromatography coordination ion-spray mass spectrometry (LC-CIS-MS) of docosahexaenoate ester hydroperoxides. Anal. Bioanal. Chem. 2004, 378, 1007- 1013.
26. Smith, L. L., Cholesterol Autoxidation, Plenum Press, New York (USA) 1981.
27. Korahani, V., Bascoul, J., Crastes de Paulet, A. Autoxidation of cholesterol fatty acid esters in solid state and aqueous dispersion. Lipids 1982, 17, 703- 708.
28. Soupas, L., Juntunen, L., Lampi, A.-M., Piironen, V., Effects of sterol structure, temperature, and lipid medium on phytosterol oxidation. J. Agric. Food Chem. 2004, 52, 6485- 6491.