Oxidative Pattern from Fluorescent Light Exposition of Crystalline Cholesterol

Food Biophysics

Volumn 7, Issue 3, 2012, Pages 209-219

  Medina Meza, Ilce Gabriela ^a   Rodríguez Estrada, María Teresa ^b   García, Hugo Sergio ^c   Lercker, Giovanni ^b  

^a Instituto Tecnologico y de Estudios Superiores de Occidente   (Mexico)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c INSTITUTO TECNOLÓGICO DE VERACRUZ   (Mexico)

Author keywords

25 hydroxycholesterol; 4 hydroxycholesterol; 6 ketocholestanol; Cholesterol photo oxidation; Side chain COPs

Indexed keywords

25-HYDROXYCHOLESTEROL; 6-KETOCHOLESTANOL; ALIPHATIC CHAINS; AMINOPROPYL; DEGRADATION BEHAVIOR; ENZYMATIC OXIDATIONS; FLUORESCENT LIGHT; GC-MS ANALYSIS; HEMATOPORPHYRIN; PHYSICAL STATE; SECONDARY PRODUCT; SIDE-CHAINS; SOLID-PHASE EXTRACTION; TYPE II;

CRYSTALLINE MATERIALS; DEGRADATION; FLUORESCENCE; OXIDATION; PORPHYRINS;

CHOLESTEROL;

EID: 84865460530     PISSN: 15571858     EISSN: 15571866     Source Type: Journal    
DOI: 10.1007/s11483-012-9259-y     Document Type: Article

References (41)

1. T. Heimburg, Thermal Biophysics of Membrane (Wiley-VCH, Weinheim, 2007).
2. V. Uskoković, Surface charge effect involved in the control of stability of sols comprising uniform cholesterol particles. Mater. Manuf. Process. 23, 620-623 (2008).
3. L. L. Smith, Cholesterol autoxidation (1981-1986). Chem. Phys. Lip. 44, 87-125 (1987).
4. A. Vejux, L. Malvitte, G. Lizard, Side effects of oxysterols: cytotoxicity, oxidation, inflammation, and phospholipidosis. Braz. J. Med. Biol. Res. 41, 545-556 (2008).
5. S. J. Hur, G. B. Park, S. T. Joo, Formation of cholesterol oxidation products (COPs) in animal products. Food Control 18, 939-947 (2007).
6. T. Saldanha, N. Bragagnolo, Effects of grilling on cholesterol oxide formation and fatty acids alteration in fish. Cienc. Tecnol. Alimen. 30(2), 385-390 (2010).
7. L. Ryan, Y. C. O'Callaghan, N. M. O'Brien, Oxidized products of cholesterol: their role in apoptosis. Curr. Nut. Food Sci. 1, 41-51 (2005).
8. G. Poli, B. Sottero, S. Gargiulo, G. Leonarduzzi, Cholesterol oxidation products in the vascular remodeling due to atherosclerosis. Mol. Aspects Med. 30, 180-189 (2009).
9. K. A. Johnson, R. M. Montano, C. J. Morrow, T. J. Scallen, In vivo formation of 25-hydroxicholesterol following a dietary cholesterol challenge. J. Lipid Res. 35(12), 2241-2253 (1994).
10. G. Le Goff, M. F. Vitha, R. J. Clarke, Orientation polarisability of lipid membrane surface. Biochim. Biophys. Acta 1768(3), 562-570 (2007).
11. K. Bodin, U. Andersson, E. Rystedt, E. Ellis, M. Norlin, I. Pikuleva, G. Eggertsen, I. Björkhem, U. Diczfalusy, Metabolism of 4β-hydroxycholesterol in humans. J. Biol. Chem. 276, 38685-38689 (2002).
12. I. G. Medina-Meza, M. T. Rodríguez-Estrada, G. Lercker, H. S. García, Unusual oxidative pattern in thermo-oxidation of dry films of cholesterol. Rev. Mex. Ing. Quim. 10(1), 47-57 (2011).
13. J. T. Chien, H. C. Wang, B. H. Chen, Kinetic model of the cholesterol oxidation during heating. J. Agr. Food Chem. 46, 2572-2577 (1998).
14. T. Y. Yen, B. S. Inbaraj, J. T. Chien, B. H. Chen, Gas chromatography-mass spectrometry determination of conjugated linoleic acids and cholesterol oxides and their stability in a model system. Anal. Biochem. 400, 130-138 (2010).
15. J. M. Luby, J. I. Gray, B. R. Harte, T. C. Ryan, Photooxidation of cholesterol in butter. J. Food Sci. 51(4), 904-907 (1986).
16. E. Boselli, M. F. Caboni, M. T. Rodríguez-Estrada, T. Gallina-Toschi, D. Mara, G. Lercker, Photooxidation of cholesterol and lipids of turkey meat during storage under commercial retail conditions. Food Chem. 91, 705-713 (2005).
17. E. Boselli, M. T. Rodríguez-Estrada, G. Fedrizzi, M. F. Caboni, Cholesterol photosensitized oxidation of beef meat under standard and modified atmosphere at retail condition. Meat Sci. 81, 224-229 (2009).
18. G. Maerker, K. C. Jones, Gamma-irradiation of individual cholesterol oxidation products. J. Am. Oil Chem. Soc. 70(3), 255-259 (1992).
19. G. Maerker, K. C. Jones, A-ring oxidation products from γ-irradiation of cholesterol in liposomes. J. Am. Oil Chem. Soc. 69, 451-455 (1993).
20. P. O. Hu, B. H. Chen, Effects of riboflavin and fatty acid methyl esters on cholesterol oxidation during illumination. J. Agr. Food Chem. 50(12), 3572-3578 (2002).
21. J. T. Chien, Y. F. Lu, P. C. Hu, B. H. Chen, Cholesterol photooxidation as affected by combination of riboflavin and fatty acid methyl esters. Food Chem. 81, 421-431 (2003).
22. M. J. Kulig, L. L. Smith, Sterol metabolism. XXV. Cholesterol oxidation by singlet molecular oxygen. J. Org. Chem. 38(20), 3639-3641 (1973).
23. C. S. Foote, Definition of type I and type II photosensitized oxidation. J. Photoch. Photobio. 54(5), 659 (1991).
24. A. W. Girotti, Photosensitized oxidation of membrane lipids: reaction pathways, cytotoxic effects, and cytoprotective mechanism. J. Photoch. Photobio. B 63, 103-113 (2001).
25. N. C. Shantha, E. A. Decker, Rapid, sensitive, iron-based spectrophotometric methods for determination of peroxide values of food lipids. J. AOAC Int. 77(2), 421-424 (1994).
26. C. Rose-Sallin, A. C. Huggett, J. O. Bosset, R. Tabacchi, L. B. Fay, Quantification of cholesterol oxidation products in milk powders using [2H7]cholesterol to monitor cholesterol autoxidation artifacts. J. Agr. Food Chem. 43(4), 935-941 (1995).
27. N. Li, T. Ohshima, K. Shozen, H. Ushio, C. Koizumi, Effects of the degree of unsaturation of coexisting trialglycerols on cholesterol oxidation. J. Am. Oil Chem. Soc. 71, 623-627 (1994).
28. V. Cardenia, M. T. Rodríguez-Estrada, F. Cumella, L. Sardi, G. Della Casa, G. Lercker, Oxidative stability of pork meat lipids as related to high-oleic sunflower oil and vitamin E diet supplementation and storage conditions. Meat Sci. 88(2), 271-279 (2011).
29. K. Wang, I. C. Peng, Electron paramagnetic resonance study of the effectiveness of myoglobin and its derivative as photosensitizer in singles oxygen generation. J. Food Sci. 53(6), 1863-1865 (1988).
30. A. Santos, A. M. Rodrigues, A. J. F. N. Sobral, P. V. Monsanto, W. L. Vaz, M. J. Moreno, Early events in photodynamic therapy: chemical and physical changes in a POPC: cholesterol bilayer due to the hematoporphyrin IX-mediated photosensitization. Photoch. Photobio. 85, 1409-1417 (2009).
31. J. M. C. Gutteridge, B. Halliwell, Free radicals and antioxidants in the year 2000: a historical look to the future. Ann. N. Y. Acad. Sci. 889, 136-147 (2000).
32. A. W. Girotti, Lipid hydroperoxydes generation, turnover, and effector action in biological systems. J. Lip. Res. 39, 1529-1542 (1998).
33. E. Choe, D. B. Min, Chemistry and reaction of reactive oxygen species in foods. J. Food Sci. 70(9), 142-159 (2005).
34. J. P. Wold, A. V. Dahl, F. Lundby, N. A. Nilsen, A. Juzeniene, J. Moan, Effect of oxygen concentration on photo-oxidation and photosensitizer bleaching in butter. Photochem. Photobio. 85, 669-676 (2009).
35. L. L. Smith, M. J. Kulig, Sterol metabolism. XXXIX. Singlet molecular oxygen from hydrogen peroxide disproportionation. J. Am. Chem. Soc. 98(4), 1027-1029 (1976).
36. G. Lercker, M. T. Rodríguez-Estrada, M. Bonoli, Analysis of the oxidation products of cis- and trans-octadecenoate methyl esters by capillary gas-chromatography-ion-trap mass spectrometry. I. Epoxide and dimeric compounds. J. Chromatogr. A 985, 333-342 (2003).
37. A. W. Girotti, Photosensitized oxidation of cholesterol in biological systems: reaction pathways, cytotoxic effects and defense mechanism. J. Photochem. Photobio. B 13(2), 105-118 (1992).
38. G. Maerker, Cholesterol autoxidation-current status. J. Am. Oil Chem. Soc. 64, 388-392 (1987).
39. L. L. Smith, Review of progress in sterol oxidation. Lipids 31, 453-488 (1986).
40. R. S. Abendan, J. A. Swift, Surface characterization of cholesterol monohydrated single crystal by chemical force microscopy. Langmuir 18, 4847-4853 (2002).
41. C. R. Loomis, G. G. Shipley, D. M. Small, The phase behavior of hydrated cholesterol. J. Lipid Res. 20, 525-535 (1979).