Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
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Formation and Inhibition of Cholesterol Oxidation Products (COPs) in Foods; An Overview

식품 내 콜레스테롤 산화 생성물(COPs)의 생성 및 억제; 개요

  • Joo-Shin Kim (Department of Food and Nutrition, Shinhan University)
  • 김주신 (신한대학교 보건대학, 식품영양학과전공)
  • Received : 2023.09.11
  • Accepted : 2023.10.27
  • Published : 2023.10.31
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Abstract

Cholesterol is prone to oxidation, which results in the formation of cholesterol oxidation products (COPs). This occurs because it is a monounsaturated lipid with a double bond on C-5 position. Cholesterol in foods is mostly non-enzymatically oxidized by reactive oxygen species (ROS)-mediated auto-oxidative reaction. The COPs are found in many common foods of animal-origin and are formed during their manufacture process. The formation of COPs is mainly related to the temperature and the heating time the food is processed, storage condition, light exposure and level of activator present such as free radical. The level of COPs in processed foods could reach up to 1-10 % of the total cholesterol depending on the foods. The most predominant COPs in foods including meat, eggs, dairy products as well as other foods of animal origin were 7-ketocholesterol, 7 α-hydroxycholesterol (7α-OH), 7β-hydroxycholesterol (7β-OH), 5,6α-epoxycholesterol (5,6α-EP), 5,6β-epoxycholesterol (5,6β-EP), 25-hydoxycholesterol (25-OH), 20-hydroxycholesterol (20-OH) and cholestanetriol (triol). They are mainly formed non-enzymatically by cholesterol autoxidation. The COPs are known to be potentially more hazardous to human health than pure cholesterol. The procedure to block cholesterol oxidation in foods should be similar to that of lipid oxidation inhibition since both cholesterol and lipid oxidation go through the same free radical mechanism. The formation of COPs in foods can be stopped by decreasing heating time and temperature, controlling storage condition as well as adding antioxidants into food products. This review aims to present, discuss and respond to articles and studies published on the topics of the formation and inhibition of COPs in foods and key factors that might affect cholesterol oxidation. This review may be used as a basic guide to control the formation of COPs in the food industry.

Keywords

References

  1. S. J. Hur, G. B. Park, S. T. Joo, "Formation of cholesterol oxidation products (COPs) in animal products", Food Control, Vol.18, pp. 939-947, (2007).  https://doi.org/10.1016/j.foodcont.2006.05.008
  2. C.Y. Tai, Y.C. Chen, B. H. Chen, "Analysis, formation and inhibition of cholesterol oxidation products in foods: an overview (part 1)", Journal of Food and Drug Analysis, Vol.7, No.4 pp. 243-257, (1999). 
  3. F. Brahmi, A. Vejux, R. Sghaier, A. Zarrouk, T. Nury, W. Meddeb, L. Rezig, A. Namsi, K. Sassi, A. Yammine, I. Badreddine, D. Vervandier-Fasseur, K. Madani, L. Boulekbache-Makhlouf, B. Nasser, G. Lizard, "Prevention of 7-ketocholesterol -induced side effects by natural compounds," Critical Reviews in Food Science and Nutrition, Vol.59. No.19 pp. 3179-3198, (2019).  https://doi.org/10.1080/10408398.2018.1491828
  4. P. B. Addis, "Occurrence of lipid oxidation products in foods," Food and Chemical Toxicology, Vol.24, pp. 1021-1030, (1986).  https://doi.org/10.1016/0278-6915(86)90283-8
  5. S. K. Peng, B. Hu, R. Morin, "Angiotoxicity and atherogenicity of cholesterol oxides," Journal of Clinical Laboratory Analysis, Vol.5 pp. 144-152, (1991).  https://doi.org/10.1002/jcla.1860050212
  6. E. Lund, I. Bjorkhem, "Down-regulation of hepatic HMG-CoA reductase in mice by dietary cholesterol: importance of the & 5 double bond and evidence that oxidation at C-3, C-5, C-6 or C-7 is not involved," Biochemistry, Vol.33, pp. 291-297, (1994).  https://doi.org/10.1021/bi00167a038
  7. E. Ryan, J. Chopra, F. McCarthy, A. R. Maguire, N. M. O'Brien, "Qualitative and quantitative comparison of the cytotoxic and apoptotic potential of phytosterol oxidation products with their corresponding cholesterol oxidation products," British Journal of Nutrition, Vol.94, pp. 443-51, (2005).  https://doi.org/10.1079/BJN20051500
  8. F. Guardiola, R. Codony, P. B. Addis, R. Rafecas, J. Boatella, "Biological effects of oxysterols: Current status," Food and Chemical Toxicology, Vol.34, pp. 193-211, (1996).  https://doi.org/10.1016/0278-6915(95)00094-1
  9. I. G. Medina-Meza, C. Ramaba, "Kinetics of cholesterol oxidation in model systems and foods: Current status," Food Engineering Reviews, Vol.5, No.3 pp. 171-184, (2013).  https://doi.org/10.1007/s12393-013-9069-0
  10. A. Otaegui-Arrazola, M. Menendez-Carreno, D. Ansorena, I. Astiasaran, "Oxysterols; A world to explore," Food and Chemical Toxicology, Vol.48, No.12 pp. 3289-3303 (2010).  https://doi.org/10.1016/j.fct.2010.09.023
  11. S. J. V. Vicente, G. R. Sampaio, C. K. B. Ferrari, E. A. F. S. Torres, "Oxidation of cholesterol in foods and its importance for human health," Food Reviews International, Vol.28, No.1 pp.47-70, (2012).  https://doi.org/10.1080/87559129.2011.594972
  12. L. L. Smith, The oxidation of cholesterol, In "Biological Effects of Cholesterol Oxides," pp. 7-31, S. K. Peng and J. R. Morin, ed. CRC Press: Boca Raton, FL., U.S.A. (1992). 
  13. N. M. Dantas, G. R. Sampaio, F. S. Ferreira, T. S. Labre, "Cholesterol oxidation in fish and fish products," Journal of Food Science, Vol.80, No.12 pp. R2627-2639, (2015).  https://doi.org/10.1111/1750-3841.13124
  14. N. Miyoshi, L. Iuliano, S. Tomono, H. Ohshima, "Implications of cholesterol autoxidation products in the pathogenesis of inflammatory diseases," Biochemical Biophysical Research Communications, Vol.446, pp. 702-708, (2014).  https://doi.org/10.1016/j.bbrc.2013.12.107
  15. L. L. Smith, "Cholesterol autoxidation," New York: Plenum Press, pp. 8-125, (1987). 
  16. E. Choe, D. B. Min, "Chemistry and reactions of reactive oxygen species in foods," Critical Reviews in Food Science and Nutrition, Vol.46, No.1 pp. 1-22, (2006).  https://doi.org/10.1080/10408390500455474
  17. K. Decamps, I. J. Joye, D. E. De Vos, C. M. Courtin, J. A. Delcour, "Molecular oxygen and reactive oxygen species in bread-making processes: scarce, but nevertheless important," Critical Reviews in Food Science and Nutrition, Vol.56, No. 5 pp.722-736, (2016).  https://doi.org/10.1080/10408398.2013.795929
  18. J. H. Nielson, C. E. Olsen, L. H. Skibsted, "Cholesterol oxidation in a heterogeneous system initiated by water-soluble radicals," Food Chemistry, Vol.56, pp. 33-37, (1996).  https://doi.org/10.1016/0308-8146(95)00146-8
  19. G. Maerker, "Cholesterol autoxidation-current status," Journal of the American Oil Chemistry' Society, Vol.64, pp. 388-392 (1987).  https://doi.org/10.1007/BF02549301
  20. S. K. Kim, W. W. Nawar, "Parameters influencing cholesterol oxidation," Lipids, Vol. 28, pp. 917-22, (1993).  https://doi.org/10.1007/BF02537501
  21. G. Maerker, F. J. Bunick, "Cholesterol oxides II. Measurement of the 5,6- epoxides during cholesterol oxidation in aqueous dispersion," Journal of the American Oil Chemists' Society, Vol.63, pp. 771-777, (1986).  https://doi.org/10.1007/BF02541962
  22. V. Verardo, M. C. Messia, E. Marconi, M. F. Caboni, "Effect of different egg products on lipid oxidation of biscuits," Foods, Vol.9, No.11 Article 1714, (2020). 
  23. D. Risso, V. Leoni, C. Fania, M. Arveda, I. Falchero, M. Barattero, A. Civra, D. Lembo, G. Poli, R. Menta, "Effect of industrial processing and storage procedures on oxysterols in milk and milk products," Food & Function, Vol.12, No.2 pp. 771-780, (2021).  https://doi.org/10.1039/D0FO02462G
  24. S. W. Park, P. B. Addis, "Cholesterol oxidation products in some muscle foods," Journal of Food Science, Vol.52, pp. 1500-1503, (1987).  https://doi.org/10.1111/j.1365-2621.1987.tb05863.x
  25. D. Derewiaka, "Formation of cholesterol oxidation products, cholesterol dimers and cholestadiens after thermal processing of cholesterol standards and butter," Journal of Lipid Science and Technology, Vol.121, No.9 Article 1800373, (2019). 
  26. B. Barriuso, A. Otaegui-Arrazola, M. Menendez-Carreno, I. Astiasaran, D. Ansorena, "Sterols heating: Degradation and formation of their ring-structure polar oxidation products," Food Chemistry, Vol.135, No.2 pp. 706-712, (2012).  https://doi.org/10.1016/j.foodchem.2012.05.027
  27. J. S. Min, S. O. Lee, M. I. Khan, D. G. Yim, K. H. Seol, M, Lee, C. Jo, "Monitoring the formation of cholesterol oxidation products in model systems using response surface methodology," Lipids in Health and Disease, Vol.14, No.9 Article 77, (2015). 
  28. D. Derewiaka, E. Molinska, "Cholesterol transformations during heat treatment," Food Chemistry, Vol.171, pp. 233-240, (2015).  https://doi.org/10.1016/j.foodchem.2014.08.117
  29. Y. Liu, X. Yang, F. Xiao, F. Jie, Q. Zhang, Y. Liu, H. Xiao, B. Lu, "Dietary cholesterol oxidation products: Perspectives linking food processing and storage with health implications," Comprehensive Reviews in Food Science and Food Safety, Vol. 21, pp. 738-779, (2021). 
  30. A. W. Girotti, "Photosensitized oxidation of membrane lipids; Reaction pathways, cytotoxic effects, and cytoprotective mechanisms," Journal of Photochemistry and Photobiology B: Biology, Vol.63, No.1 pp. 103-113, (2001).  https://doi.org/10.1016/S1011-1344(01)00207-X
  31. V. Cardenia, M. T. Rodriguez-Estrada, E. Boselli, G. Lercker, "Cholesterol photosensitized oxidation in food and biological systems," Biochimie, Vol.95, No.3 pp. 473-481, (2013).  https://doi.org/10.1016/j.biochi.2012.07.012
  32. B. Lu, Y. Zhao, "Photooxidation of phytochemicals in food and control: A review," Annals of the New York Academy of Sciences, Vol.1398, No.1 pp. 72-82, (2017).  https://doi.org/10.1111/nyas.13377
  33. l. Kaczynski, D. Cais-Sokolinska, M. Rudzinska, "Cholesterol oxidation products in kefir from goats' milk during storage," International Dairy Journal, Vol.85, pp. 35-40, (2018).  https://doi.org/10.1016/j.idairyj.2018.05.002
  34. E. Boselli, M. F. Caboni, M. T. Rodriguez-Estrada, T. G. Toschi, M. Daniel, G. Lercker, "Photoxidation of cholesterol and lipids of turkey meat during storage under commercial retail conditions," Food Chemistry, Vol.91, No.4 pp. 705-713, (2005).  https://doi.org/10.1016/j.foodchem.2004.06.043
  35. I. Madonado-Peretra, M. Schwetes, C. Bamaba, I. G. Medina-Meza, "The role of cholesterol oxidation products in food toxicity," Food and Chemical Toxicology, Vol. 118, pp. 908-939, (2018).  https://doi.org/10.1016/j.fct.2018.05.059
  36. D. Cais-Sokolinska, M. Rudzinska, "Short communication: Cholesterol oxidation products in traditional buttermilk," Journal of Dairy Science, Vol.101, No.5 pp. 3829-3834, (2018).  https://doi.org/10.3168/jds.2017-13942
  37. S. A. Rather, F. A. Masoodi, J. A. Rather, A. Gani, S. M. Wani, T. A. Ganaie, R. Akhter, "Impact of thermal processing and storage on fatty acid composition and cholesterol oxidation of canned traditional low-fat meat product of India," Lwt-Food Science and Technology, Vol.139, Article 110503, (2021). 
  38. A. Conchillo, D. Ansorena, I. Astiasaran, "Intensity of lipid oxidation and formation of cholesterol oxidation products during frozen storage of raw and cooked chicken," Journal of the Science of Food and Agriculture, Vol.84, pp. 141-146, (2005).  https://doi.org/10.1002/jsfa.1969
  39. D. Risso, V. Leoni, F. Canzoneri, M. Arveda, R. Zivoli, A. Peraino, G. Poli, R. Menta, "Presence of cholesterol oxides in milk chocolates and their correlation with milk power freshness," PLoS ONE, Vol.17, No.3 e0264288, (2022). 
  40. G. Lercker, M. T. Rodriguez-Estrada, "Cholesterol oxidation: presence of 7-ketocholesterol in different food products," Journal of Food Composition and Analysis, Vol.13, pp. 625-631, (2000).  https://doi.org/10.1006/jfca.2000.0901
  41. S. R. Baggio, E. Vicente, N. Bragagnolo, "Cholesterol oxides, cholesterol total lipid and fatty acid composition in Turkey meat," Journal of the Science of Food and Agriculture, Vol.50, pp. 5981-5986, (2002).  https://doi.org/10.1021/jf020025c
  42. J. -S. Kim, "E Vitamer fraction in rice bran inhibits autoxidation of cholesterol and linoleic acid in emulsified system during incubation," Journal of Food Science, Vol. 70, No.4 pp. C286-291, (2005).  https://doi.org/10.1111/j.1365-2621.2005.tb07175.x
  43. M. P. Zubillaga, G. Maerker, "Quantification of three cholesterol oxidation products in raw meat and chicken. Journal of Food Science, Vol.56, pp. 1194-1196, (1991).  https://doi.org/10.1111/j.1365-2621.1991.tb04732.x
  44. J. Pikul, M. Rudzinska, J. Teichert, A. Lasik, R. Dankow, R. Przybylski, "Cholesterol oxidation during storage of UHT-treated bovine and caprine milk," International Dairy Journal, Vol.30, No.1 pp. 29-32, (2013).  https://doi.org/10.1016/j.idairyj.2012.11.005
  45. B. D. Sander, P.B. Addis, S. W. Park, D. E. Smith, "Quantification of cholesterol oxidation products in a variety of foods," Journal of Food Protection, Vol.52, pp. 109-114, (1989).  https://doi.org/10.4315/0362-028X-52.2.109
  46. A. Obara, M. Obiedzinski, T. Kolczak, "The effect of water activity on cholesterol oxidation in spray-and freeze-dried egg powders," Food Chemistry, Vol.95, pp. 173-179, (2005).  https://doi.org/10.1016/j.foodchem.2004.06.021
  47. M. F. Caboni, E. Boseli, M. C. Messia, V. Velazco, A. Fratianni, G. Panfili, E. Marconi, "Effect of processing and storage on the chemical quality markers of spray-dried whole egg," Food Chemistry, Vol.92, pp. 293-303, (2005).  https://doi.org/10.1016/j.foodchem.2004.07.025
  48. A. Valenzuela, J. Sanhueza, S. Nieto, "Cholesterol oxidation: health hazard and the role of antioxidants in prevention," Biological Research, Vol.36, pp. 291-302, (2003). 
  49. M. Joshi, P. Darshane, M. Beke, "Potential means to lower cholesterol oxidation products (COPs) in the diet," International Journal of Current Medical and Pharmaceutical Research, Vol.7, No.3 pp. 5632-5636, (2021). 
  50. S. Kubow, "Lipid oxidation products in food and atherogenesis," Nutrition Review, Vol.51, pp. 33-40, (1993).  https://doi.org/10.1111/j.1753-4887.1993.tb03064.x
  51. A. Csallany, J. H. Lee, D. Shoeman, "Protection of superoxide-induced cholesterol oxidation by antioxidants in protic conditions," International Journal of Food Science and Nutrition, Vol.53, pp. 403-409, (2002).  https://doi.org/10.1080/0963748021000044741
  52. A. Valenzuela, J. Sanhueza, S. Nieto, "Effect of synthetic antioxidants on cholesterol stability during the thermal-induced oxidation of a polyunsaturated vegetable oil," Journal of American Oil Chemists' Society, Vol.79, pp. 325-328, (2002).  https://doi.org/10.1007/s11746-002-0482-x
  53. B. Janoszka, "7-Ketocholesterol and 7-hydroxycholesterol in pork meat and its gravy thermally treated without additives and in the presence of onion and garlic," Meat Science, Vol.86, No.4 pp. 976-984, (2010).  https://doi.org/10.1016/j.meatsci.2010.08.003
  54. L. Mariutti, G. Nogueira, N. Bragagnolo, "Lipid and cholesterol oxidation in chicken meat are inhibited by sage but not by garlic," Journal of Food Science, Vol.76, No.6 pp. C909-915, (2011).  https://doi.org/10.1111/j.1750-3841.2011.02274.x
  55. I. Meza, M. Schweiss, C. Barnaba, "Montmorency tart cherry anthocyanins: dose-dependent antioxidant activity against cholesterol oxidation," The FASEB Journal, Vol.32, No.S1 pp. 656.30, (2018).