Oxidation of Cholesterol in Foods and Its Importance for Human Health

Food Reviews International

Volumn 28, Issue 1, 2012, Pages 47-70

  Vicente, Silvio J V ^a   Sampaio, Geni R ^a   Ferrari, Carlos K B ^b   Torres, Elizabeth A F S ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF MATO GROSSO   (Brazil)

Author keywords

biologic effects; cholesterol; cholesterol oxidation products

Indexed keywords

ANIMALIA;

EID: 84858836654     PISSN: 87559129     EISSN: 15256103     Source Type: Journal    
DOI: 10.1080/87559129.2011.594972     Document Type: Review

References (92)

1. Ikonen, E. 2006. Mechanisms of cellular cholesterol transport: Defects and human disease. Physiol. Rev., 86: 1237-1261.
2. Hur, S.J., Park, G.B. and Joo, S.T. 2007. Formation of cholesterol oxidation products (COPs) in animal products. Food Control., 18: 939-947.
3. Murphy, R.C. and Johnson, K.M. 2008. Cholesterol, reactive oxygen species, and the formation of biologically active mediators. J. Biol. Chem., 283: 15521-15525.
4. Daniels, T.F., Killinger, K.M., Michal, J.J., Wright, R.W. and Jr.; Jiang, Z. 2009. Lipoproteins, cholesterol homeostasis and cardiac health. Int. J. Sci., 5: 474-488.
5. Ikonen, E. 2008. Cellular cholesterol trafficking and compartmentalization. Nat. Rev. Mol. Cell Biol., 9: 125-138.
6. Yen, T.Y., Inbaraj, B.S., Chien, J.T. and Chen, B.H. 2010. Gas chromatography-mass spectrometry determination of conjugated linoleic acids and cholesterol oxides and their stability in a model system. Anal. Biochem., 400: 130-138.
7. Lloyd-Jones, D., Adams, R, Carnethon, M, Simone, G., Ferguson, T.B.Flegal, K. 2009. Heart disease and stroke statistics-2009 update: A report from the American Heart Association Statistics Committee and Stroke Statistics Subcommittee. Circulation, 119: 480-486.
8. Linseisen, J. and Wolfram, G. 1998. Origin, metabolism and adverse health effects of cholesterol oxidation products. Fett. Lipid., 100: 211-218.
9. Ryan, E., Chopra, J., McCarthy, F., Maguire, A.R. and O'Brian, N.M. 2005. Qualitative and quantitative comparison on the cytotoxic and apoptotic potential of phytosterol oxidation products with their corresponding cholesterol oxidation products. Br. J. Nutr., 94: 443-451.
10. Olkkonen, V.M. and Lehto, M. 2004. Oxysterols and oxysterol binding proteins: Role in lipid metabolism and atherosclerosis. Ann. Med., 36: 562-572.
11. Kemmo, S., Ollilainen, V., Lampi, A.M. and Piironen, V. 2007. Determination of stigmasterol and cholesterol oxides using atmospheric pressure chemical ionization liquid chromatography/mass spectrometry. Food Chem., 101: 1438-1445.
12. Savage, G.P., Dutta, P.C. and Rodriguez-Estrada, M.T. 2002. Cholesterol oxides: Their occurrence and methods to prevent their generation. Asia Pacific J. Clin. Nutr., 11: 72-78.
13. Guardiola, F., Tres, A., Codony, R., Addis, P.B., Bergmann, S.D. and Zavoral, J.H. 2007. Lack of effect of oral supplementation with antioxidants on cholesterol oxidation product concentration of human plasma, as reveled by an improved gas chromatography method. Anal. Bioanal. Chem., 389: 277-289.
14. Valenzuela, A., Sanhueza, J. and Nieto, S. 2003. Cholesterol oxidation: Health hazard and the role of antioxidants in prevention. Biol. Res., 36: 291-302.
15. Schroepfer, G.J. 2000. Oxysterols: Modulators of cholesterol metabolism and other processes. Physiol. Rev., 80: 361-554.
16. Dutta, P.C. 2004. Accurate and reproducible methods for analysis of sterol oxidation products in foods: An overview. J. AOAC Int., 87: 439-440.
17. Raith, K., Brenner, C., Farwanah, H., Muller, G., Eder, K. and Neubert, R.H.H. 2005. A new LC/APCI-MS method for the determination of cholesterol oxidation products in food. J. Chromatogr. A., 1067: 207-211.
18. Vicente, S.J.V. and Torres, E.A.F.S. 2007. Formation of four cholesterol oxidation products and loss of free lipids, cholesterol and water in beef hamburgers as a function of thermal processing. Food Control., 18: 63-68.
19. Smith, L.L. 1996. Review of progress in sterol oxidations: 1987-1995. Lipids, 31: 453-487.
20. Chien, J.T., Lu, Y.F., Hu, P.C. and Chen, B.H. 2003. Cholesterol photooxidation as affected by combination of riboflavin and fatty acid methyl esters. Food Chem., 81: 421-431.
21. Mariutti, L.R.B., Nogueira, G.C. and Bragagnolo, N. 2008. Optimization and validation of analytical conditions for cholesterol and cholesterol oxides extraction in chicken meat using response surface methodology. J. Agric. Food Chem., 56: 2913-2918.
22. Brown, A.J. and Jessup, W. 2009. Oxysterols: Sources, cellular storage and metabolism, and new insights into their roles in cholesterol homeostasis. Mol. Aspects Med., 20: 111-122.
23. Choe, E. and Min, D.B. 2006. Chemistry and reactions of reactive oxygen species in foods. Crit. Rev. Food Sci. Nutr., 46: 1-22.
24. Carpenter, K.L.H. 2002. God COP, bad COP: An unsolved murder. Are dietary cholesterol oxidation products guilty of atherogenicity? Br. J. Nutr., 88: 335-338.
25. Aizpurúa, I.C.M. and Tenuta-Filho, A. 2005. Oxidation of cholesterol in mayonnaise during storage. Food Chem., 89: 611-615.
26. Maerker, G. 1987. Cholesterol autoxidation-Current status. J. Am. Oil Chem. Soc., 64: 388-392.
27. Kubow, S. 1992. Routes of formation and toxic consequences of lipid oxidation products in food. J. Free Radic. Biol. Med., 12: 63-81.
28. Smith, L.L. 1981. "Distribution of Autoxidation Products". In Cholesterol Autoxidation, 49-123. New York: Plenum Press.
29. Gordon, M.H. 2000. "The mechanism of antioxidant action". In Food Antioxidants, 1-18. London: Elsevier Applied Science.
30. Hoac, T., Daun, C., Trafikowska, J. and Akesson, B. 2006. Influence of heat treatment on lipid oxidation and glutathione peroxidase activity in chicken and duck meat. Innov. Food Sci. Emerg. Technol., 7: 88-93.
31. Xu, Z., Zhang, T., Prinyawiwatkul, W. and Godber, S. 2005. Capabilities of different cooking oil in prevention of cholesterol oxidation during heating. J. Am. Oil Chem. Soc., 82: 243-248.
32. Kim, S.K. and Nawar, W.W. 1993. Parameters influencing cholesterol oxidation. Lipids, 28: 917-922.
33. Palozza, P., Barone, E., Mancuso, C. and Picci, N. 2008. The protective role of carotenoids against 7-ketocholesterol formation in solution. Mol. Cell Biochem., 309: 61-68.
34. Broncano, J.M., Petrón, M.J., Parra, V. and Timón, M.L. 2009. Effect of different cooking methods on lipid oxidation and formation of free cholesterol oxidation products (COPs) in Latissimus dorsi of Iberian pigs. Meat Sci., 83: 431-437.
35. Al-Saghir, S., Thurner, K., Wagner, K.H., Frisch, G., Luf, W., Razzazi-Fazeli, E. and Elmadfa, I. 2004. Effects of different cooking procedures on lipid quality and cholesterol oxidation of farmed salmon fish (Salmo salar). J. Agric. Food Chem., 52: 5290-5296.
36. Ohshima, T., Li, N. and Koizumi, C. 1993. Oxidative decomposition of cholesterol in fish products. J. Am. Oil Chem. Soc., 70: 595-599.
37. Sampaio, G.R., Bastos, D.H.M., Soares, R.A.M., Queiroz, Y.S. and Torres, E.A.F.S. 2006. Fatty acids and cholesterol oxidation in salted and dried shrimp. Food Chem., 95: 344-351.
38. Saldanha, T. and Bragagnolo, N. 2007. Cholesterol oxidation is increased and PUFAs decreased by frozen storage and grilling of Atlantic hake fillets (Merluccius hubbsi). Lipids, 42: 671-678.
39. Soto-Rodríguez, I., Campillo-Velázquez, P.J., Ortega-Martínez, J., Rodríguez-Estrada, M.T., Lercker, G. and Garcia, H.S. 2008. Cholesterol oxidation in traditional Mexican dried and deep-fried food products. J. Food Compost. Anal., 21: 489-495.
40. Obara, A., Obiedziński, M. and Kołczak, T. 2006. The effect of water activity on cholesterol oxidation in spray-dried egg powders. Food Chem, 95: 173-179.
41. Maerker, G. and Bunick, F.J. 1986. Cholesterol oxides II: measurement of the 5,6 epoxides during cholesterol oxidation in aqueous dispersions. J. Am. Oil Chem. Soc., 63: 771-777.
42. De Vore, V.R. 1988. TBA values and 7-ketocholesterol in refrigerated raw and cooked ground beef. J. Food Sci., 53: 1058-1061.
43. Conchillo, A., Ansorena, D. and Astiasaran, I. 2005. Intensity of lipid oxidation and formation of cholesterol oxidation products during frozen storage of raw and cooked chicken. J. Sci. Food Agric., 84: 141-146.
44. Cachaldora, P., Garcia-Rebollar, P., Alvarez, C., Méndez, J. and De Blas, J.C. 2008. Double enrichment of chicken eggs with conjugated linoleic acid and n-3 fatty acids through dietary fat supplementation. Anim. Feed Sci. Technol., 144: 315-326.
45. Mazalli, M.R. and Bragagnolo, N. 2009. Increase of cholesterol oxidation and decrease of PUFAs as a result of thermal processing and storage in eggs enriched with n-3 fatty acids. J. Agric. Food Chem., 57: 5028-5034.
46. Mazalli, M.R. and Bragagnolo, N. 2007. Effect of storage on cholesterol oxide formation and fatty acid alterations in egg powder. J. Agric. Food Chem., 55: 2743-2748.
47. Saldanha, T., Benassi, M.T. and Bragagnolo, N. 2008. Fatty acid contents evolution and cholesterol oxides formation in Brazilian sardines (Sardinella brasiliensis) as a result of frozen storage followed by grilling. LWT Food Sci. Technol., 41: 1301-1309.
48. Ferioli, F., Caboni, M.F. and Dutta, P.C. 2008. Evaluation of cholesterol and lipid oxidation in raw and cooked minced beef stored under oxygen-enriched atmosphere. Meat Sci., 80: 681-685.
49. Boselli, E., Caboni, M.A., Rodriguez-Estrada, M.T., Toschi, T.G., Daniel, M. and Lercker, G. 2005. Photoxidation of cholesterol and lipids of turkey meat during storage under commercial retail conditions. Food Chem., 91: 705-713.
50. Ahn, D.U., Nam, K.C., Du, M. and Jo, C. 2001. Effect of irradiation and packing conditions after cooking on the formation of cholesterol and lipid oxidation products in meat during storage. Meat Sci., 57: 413-418.
51. Zanardi, E., Battaglia, A., Ghidini, S., Conter, M., Badiani, A. and Ianieri, A. 2009. Lipid oxidation of irradiated pork products. LWT Food Sci. Technol., 42: 1301-1307.
52. Verardo, V., Pasini, F., Iafelice, F., Messia, M.C., Marconi, E. and Caboni, M.F. 2010. Influence of storage conditions on cholesterol oxidation in dried egg pasta. J. Agric. Food Chem., 58: 3586-3590.
53. Lee, H.W., Chien, J.T. and Chen, B.H. 2008. Inhibition of cholesterol oxidation in marinated foods as affected by antioxidant during heating. Food Chem., 108: 234-244.
54. Baggio, S.R. and Bragagnolo, N. 2006. The effect of heat treatment on the cholesterol oxides, cholesterol, total lipid and fatty contents of processed meat products. Food Chem., 95: 611-619.
55. Baggio, S.R. and Bragagnolo, N. 2006. Cholesterol oxide, cholesterol, total lipid and fatty acid contents in processed meat products during storage. Lebens. Winss. Technol., 39: 513-520.
56. Galvin, K., Lynch, A.M., Kerry, J.P., Morrissey, P.A. and Buckley, D.J. 2000. Effect of dietary vitamin E supplementation on cholesterol oxidation in vacuum packaged cooked beefsteaks. Meat Sci., 55: 7-11.
57. Chien, J.T., Hsu, D.J. and Chen, B.H. 2006. Kinetic model for studying the effect of quercetin on cholesterol oxidation during heating. J. Agric. Food Chem., 54: 1486-1492.
58. Guardiola, F., Bou, R., Boatella, J. and Codony, R. 2004. Analysis of sterol oxidation products in foods. J. AOAC Int., 87: 441-466.
59. Saldanha, T., Sawaya, A.C.H.F., Eberlin, M.N. and Bragagnolo, N. 2006. HPLC separation and determination of 12 cholesterol oxidation products in fish: Comparative study of RI, UV, and APCI-MS detectors. J. Agric. Food Chem., 54: 4107-4113.
60. Gill, S., Chow, R. and Brown, A.J. 2008. Sterol regulators of cholesterol homeostasis and beyond: The oxysterol hypothesis revisited and revised. Prog. Lipid Res., 47: 391-404.
61. Russel, D.W. 2000. Oxysterol biosynthetic enzymes. Biochim. Biophys. Acta, 1529: 126-135.
62. Staprans, I., Rapp, J.H., Pan, X.M. and Feingold, K.R. 2003. Oxidized cholesterol in the diet is a source of oxidized lipoproteins in human serum. J. Lipid Res., 44: 705-715.
63. Meynier, A., Lherminier, J., Demaison-Meloche, J., Ginies, C., Grandgirard, A. and Demaison, L. 2002. Effects of dietary oxysterols on coronary arteries in hyperlipidaemic hamsters. Br. J. Nutr., 87: 447-458.
64. Ando, M., Tomoyori, H. and Imaizumi, K. 2002. Dietary cholesterol-oxidation products accumulate in serum and in liver in apolipoprotein E-deficient mice, but do not accelerated atherosclerosis. Br. J. Nutr., 88: 339-345.
65. Osada, K., Sasaki, E. and Sugano, M. 1994. Lymphatic absorption of oxidized cholesterol in rats. Lipids, 29: 555-559.
66. Linseisen, J. and Wolfram, G. 1998. Absorption of cholesterol oxidation products from ordinary foodstuffs in humans. Ann. Nutr. Metab., 42: 221-230.
67. Emanuel, H.A., Hassel, C.A., Addis, P.B., Bergman, S.D. and Zavorel, J.H. 1991. Plasma cholesterol oxidation products (oxysterols) in humans subject fed a meal rich in oxysterols. J. Food Sci., 56: 843-847.
68. Leonarduzzi, G., Sottero, B. and Poli, G. 2002. Oxidized products of cholesterol: Dietary and metabolic origin, and proatherosclerotic effects [review]. J. Nutr. Biochem., 13: 700-710.
69. Bascoul, J., Domergue, N., Mourot, J., Debry, G. and Paulet, A.C. 1986. Intestinal absorption and fecal excretion of 5,6α-epoxy-5α-cholesta-3β-ol by the male Wistar rats. Lipids, 21: 744-747.
70. Fuda, H., Javitt, N.B., Mitamura, K., Ikegawa, S. and Stroff, C.A. 2007. Oxysterols are substrates for cholesterol sulphotransferase. J. Lipid Res., 48: 1343-1352.
71. Wang, J., Megha, T. and London, E. 2004. Relationship between sterol/steroid structure and participation in ordered lipid domains (lipid rafts): Implications for lipid raft structure and functions. Biochemistry, 43: 1010-1018.
72. Guardiola, F., Codony, R., Addis, P.B., Rafecas, M. and Boatella, J. 1996. Biological effects of oxysterols: Current status. Food Chem. Toxicol., 34: 193-211.
73. Ong, W.Y., Goh, E.W.S., Lu, X.R., Farooqui, A.A., Patel, S.C. and Halliwell, B. 2003. Increase in cholesterol and cholesterol oxidation products, and role of cholesterol oxidation products in kainate-induced neuronal injury. Brain Pathol., 13: 250-262.
74. Lin, C.Y. and Morel, D.W. 1996. Esterification of oxysterols in human serum: Effects on distribution and cellular uptake. J. Lipid Res., 37: 168-178.
75. Olkkonen, V.M. and Hynynen, R. 2009. Interactions of oxysterols with membranes and proteins. Mol. Aspects Med., 30: 123-133.
76. 2/M phase in the human monocytic THP-1 cell line. Life Sci., 72: 1389-1399.
77. Ryan, L., O'Callaghan, Y.C. and O'Brien, N. 2005. The role of the mitochondria in apoptosis induced by 7β-hydroxycholesterol and cholesterol-5β-6β-epoxyde. Br. J. Nutr., 94: 519-525.
78. Li, A.C. and Glass, C.K. 2004. PPAR- and LXR-dependent pathways controlling lipid metabolism and the development of atherosclerosis. J. Lipid Res., 45: 2161-2173.
79. Wielkoszyński, T., Gawron, K., Strzelczyk, J., Bodzek, P., Zalewska-Ziob, M., Trapp, G., Srebniak, M. and Wiczkowski, A. 2006. Cellular toxicity of oxysterols. Bioessays., 28: 387-398.
80. Osada, K., Minehira, K., Inoue, S., Nakamura, S., Yamada, K. and Sugano, M. 2000. Effect of oxidized cholesterol on age-associated changes to immune parameters in spleen lymphocytes and peritoneal exudate cells derived from rats. Biosci. Biotechnol. Biochem., 64: 1047-1051.
81. Umetani, M., Domoto, H., Gormley, A.K., Yuhanna, I.S., Cummins, C.L., Javitt, N.B., Korach, K.S., Shaul, P.W. and Mangelsdorf, D.J. 2007. 27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen. Nat. Med., 13: 1185-1192.
82. Hayden, J.M., Brachova, L., Higgins, K., Obermiller, L., Sevanian, A., Khandrika, S. and Reaven, P.D. 2002. Induction of monocyte differentiation and foam cell formation in vitro by 7-ketocholesterol. J. Lipid Res., 43: 26-35.
83. Staprans, I., Pan, X.M., Rapp, J.H., Grunfeld, C. and Feingold, K.R. 2000. Oxidized cholesterol in the diet accelerate development of atherosclerosis in LDL-receptor and apolipoprotein E-deficient mice. Arterioscler. Thromb. Vasc. Biol., 20: 708-714.
84. Lyons, M.A. and Brown, A.J. 1999. 7-Ketocholesterol. Int. J. Biochem. Cell Biol., 31: 369-375.
85. Ferrari, C.K.B. 2000. Free radicals, lipid peroxidation and antioxidants in apoptosis: Implications in cancer, cardiovascular and neurological diseases. Biologia, 55: 579-590.
86. Black, H.S. and Douglas, D.R. 1972. A model system for the evaluation of the role of α-oxide in ultraviolet carcinogenesis. Cancer Res., 32: 2630-2632.
87. Kendal, C.W., Koo, M., Sokoloff, E. and Rao, V. 1992. Effect of dietary oxidized cholesterol on azoxymethane-induced colonic preneoplasia in mice. Cancer Lett. 1, 66: 241-248.
88. Sevanian, A. and Peterson, A.R. 1986. The cytotoxic and mutagenic properties of cholesterol oxidation products. Food Chem. Toxicol., 24: 1103-1110.
89. Sporer, A., Brill, D.R. and Schaffner, C.P. 1982. Epoxycholesterols in secretions and tissue of normal, benign, and cancerous human prostate glands. Urology, 20: 244-250.
90. Cheng, Y.W., Kang, J.J., Shih, Y.L., Lo, Y.L. and Wang, C.F. 2005. Cholesterol-3-beta, 5-alpha, 6-beta-triol induced genotoxicity through reactive oxygen species formation. Food Chem. Toxicol., 43: 617-622.
91. Yoon, J.H., Canbay, A.E., Werneburg, N.W., Lee, S.P. and Gores, G.J. 2004. Oxysterols induce cyclooxygenase-2 expression in cholangiocytes: Implications for biliary tract carcinogenesis. Hepatology, 39: 732-738.
92. Biasi, F., Mascia, C. and Poli, G. 2008. The contribution of animal fat oxidation products to colon carcinogenesis, through modulation of TGF-β1 signaling. Carcinogenesis, 29: 890-894.