Parole chiave
cholesterol oxidation products
analysis
health diseases
Abstract
Cholesterol is one of the important components of biological membranes. It is associated with milk fat in milk and milk products. Cholesterol present in animal origin foods undergoes autoxidation during processing as well as during storage yielding toxic products commonly known as cholesterol oxidation products (COPs). The COPs are significantly affected the human health such as atherosclerosis, inflammation, cancer, neurodegenerative diseases etc. Various methods are reported in literature for determination of cholesterol and its oxidation products in milk and milk products.
Riferimenti bibliografici
Agarwal, B.D., Sikka K.K., Srivastava, D,K,, Wali, M., 1980. Effect of lactose on serum lipids in cases of coronary artery disease. J Indian Med Assoc, 75,153–156.
Andrade, S., Borges, N., 2009. Effect of fermented milk containing Lactobacillus acidophilus and Bifidobacterium longum on plasma lipids of women with normal or moderately elevated cholesterol. J Dairy Res, 76,469–474.
Anggakusuma, Romero-Brey, I. , Berger, C., Colpitts, C.C, Boldanova, T., Engelmann, M., Todt, D., Perin, P.M., Behrendt, P., Vondran, F.W., Xu, S.T., Goffinet, C., Schang, L.M., Heim, M.H., Bartenschlager, R., Pietschmann, T., Steinmann, E., 2015. Interferon-inducible cholesterol-25-hydroxylase restricts hepatitis C virus replication through blockage of membranous web formation. Hepatology 62, 702–714.
AOAC (2005). Cholesterol in foods. Official Methods of Analysis, 18th ed. Chapter 45, pp. 100-102.
Aoyama, T., Nosaka, N., Kasai, M., 2007. Research on the nutritional characteristics of medium chain fatty acids. J Med Invest 54:385–388.
Aristova V., Bekhova E. (1976). Cholesterol in milk and milk products. Trudy, Vsesoyuznyi Nanchnoissledova-tel’skii Institute Malochoi Promyshlennosti 42: 45.
Arul J.A., Boudreau A., Makhloufm J., Tardif R., Grenier B. 1988. Distribution of cholesterol in milk fat fractions. J Dairy Res 55: 361-371.
Bachman K.C., Lin J.H., Wilcox C.J. 1976. Sensitive colorimetric determination of cholesterol in dairy products. J Assoc Off Anal Chem, 59(5), 1146-1149.
Bican P. (1984). Oxycholesterine in Milch and Milch produkte. unpublished results.
Bindal M.P., Jain M. (1973). Estimation of total cholesterol in ghee prepared from milk of cows and buffaloes. Indian J. Chem 3: 63-65.
Bjorkhem I., Lovgren-Sandblom A., Leoni V, Meaney S., Brodin L., Salveson L., Winge K., Palhagen S., Svenningsson P. 2013. Oxysterols and Parkinson’s disease: evidence that levels of 24S-hydroxycholesterol in cerebrospinal fluid correlates with the duration of the disease. Neurosci. Lett 555, 102–105.
Bjorkhem I., Cedazo-Minguez A., Leoni V., Meaney S. 2009. Oxysterols and neurodegenerative diseases. Mol. Aspects Med 30, 171–179.
Bjorkhem I. 2006. Crossing the barrier: oxysterols as cholesterol transporters and metabolic modulators in the brain. J. Intern. Med 260, 493–508.
Bosco D.A., Fowler D.M., Zhang Q., Nieva J., Powers E.T., Wentworth J.P., Lerner R.A., Kelly J.W. 2006. Elevated levels of oxidized cholesterol metabolites in Lewy body disease brains accelerate alpha-synuclein fibrilization. Nat. Chem. Biol 2, 249–253
Boudreau A., Arul J. (1993). Cholesterol Reduction and Fat Fraction Technologies for Milk Fat: An Overview. J Dairy Sci 76, 1772- 1781.
Bourque C., Stonge M.P., Papamandjaris A.A., Cohn J.S., Jones P.J. 2003. Consumption of an oil composed of medium chain triacyglycerols, phytosterols, and N3 fatty acids improves cardiovascular risk profile in overweight women. Metabolism 52:771–777.
Bradley R.L. (1990). Removal of Cholesterol from Milk Fat Using Supercritical Carbon Dioxide. J. Dairy Sci 72(10), 2834-2840.
Brouwer I.A., Wanders A.J., Katan M.B. 2010. Effect of animal and industrial trans fatty acids on HDL and LDL cholesterol levels in humans – a quantitative review. PLoS One 5:e9434.
Brown A.J., Jessup W. 1999. Oxysterols and atherosclerosis. Atherosclerosis 142, 1– 28.
Burke R.W., Diamond B.I., Velapoldi R.A., Menis O. (1974). Mechanisms of the Liebermann-Burchard and Zak Color Reactions for Cholesterol. Clin. Chem 20: 794-801.
Carrol R.M., Rudel L.L. 1981. Evaluation of a high-performance liquid chromatography method for isolation and quantitation of cholesterol and cholesteryl esters. J. Lipid Res 22: 359-363.
Chardigny J.M., Destaillats F., MalpuechBrugere C., Moulin J., Bauman D.E., Lock A.L. 2008.Do trans fatty acids from industrially produced sources and from natural sources have the same effect on cardiovascular disease risk factors in healthy subjects? Results of the trans Fatty Acids Collaboration (TRANSFACT) study. Am J Clin Nutr 87:558–66.
Chen J.H., Peng D.Q. 2015. Is 25-hydroxycholesterol the interplay of statins and inflammation? Int. J. Cardiol 184, 255–256.
Chen Q., Reimer R.A. 2009. Dairy protein and leucine alter GLP1 release and mRNA of genes involved in intestinal lipid metabolism in vitro. Nutrition 25:340–9.
Chisolm G.M., Steinberg D. 2000. The oxidative modification hypothesis of atherogenesis: an overview. Free Radic. Biol Med 28, 1815–1826.
Christodoulou S., Hung T. V., Trewhell M. A., Black R. G. (1994). Enzymatic Degradation of Egg Yolk Cholesterol. J Food Prot 57(10), 908-1012.
Civra A., Cagn, V, Donalisio M, Biasi F, Leonarduzzi G, Poli G, Lembo D. 2014. Inhibition of pathogenic non-enveloped viruses by 25-hydroxycholesterol and 27-hydroxycholesterol. Sci 4, 7487.
Cleveland M, Harris N. (1987). Oxidation of cholesterol in commercially processed cow’s milk. J. Food Prot 50: 867–871.
Dasari B, Prasanthi JR, Marwarha G, Singh BB, Ghribi O. 2010. The oxysterol 27-hydroxycholesterol increases beta-amyloid and oxidative stress in retinal pigment epithelial cells. BMC Ophthalmol. 10.
Davidson S. (1990). Low Cholesterol Milk and Eggs. Rural Research 148, 27-28.
De Weille. J, Fabre C., Bakalara N., 2013. Oxysterols in cancer cell proliferation and death. Biochem Pharmacol 86:154–160.
Dehal SS, Freier T.T., Young J.W., Hartman P.A., Beitz D.C. (1991). Fat and Cholesterol Reduced Food: Technologies and Strategies, Haberstroh C, Moms C. (Eds.), Portflio Publishing Company, Woodlands, p 203-220.
Dionisi F., Golay P.A., Aeschlimann, J.M., Fay, L.B., (1998). Determination of cholesterol oxidation products in milk powders: Methods comparison and validation. J. Agric. Food Chem 46:2227-2233.
Dobarganes, C., Marquez-Ruiz G. 2003. Oxidize fat in foods. Curr Opin Clin Nutr Metab Care 6,157-162.
Duncan I.W., Culberth, P.H., Bartis, C.A., 1979. Determination of free and esterified cholesterol by high performance liquid chromatography. J. Chromatogr 162: 281-292.
DuSell, C.D., Nelson, E.R., Wang, X.J., Abdo, J., Moedder, U.I., Umetani, M., Gesty- Palmer, D., Javitt, N.B., Khosla, S., McDonnell, D.P., 2010. The endogenous selective estrogen receptor modulator 27-Hydroxycholesterol is a negative regulator of bone homeostasis. Endocrinology 151, 3675–3685
Ebringer, L., Ferencik, M., Krajcovic J. 2008.Beneficial health effects of milk and fermented dairy products – review. Folia Microbiol (Praha) 53:378–94.
Fernandez, M.L., West K.L. 2005. Mechanisms by which dietary fatty acids modulate plasma lipids. J Nutr. 135:2075–8.
Folch J., Lees M., Stanley G.H.S. (1957). A simple method for the isolation and purification of total lipides from animal tissues. J. Biol. Chem 226: 497-509.
Fuke Y., Matsuoka H. (1974). Cholesterol content and identification of foreign fats in processed cheese. Journal of Japanese Society of Food Nutrition, 27, 269.
Gamba P, Testa G, Gargiulo S, Staurenghi E, Poli G, Leonarduzzi G. 2015. Oxidized cholesterol as the driving force behind the development of Alzheimer's disease. Front. Aging Neurosci 7.
Goldstein, J.L., H.o Y.K., Basu S.K., Brown M.S. 1979. Binding site on macrophages that mediates uptake and degradation of acetylated low density lipoprotein, producing massive cholesterol deposition. Proc. Natl. Acad. Sci 76, 333–337.
Grundy S.M. 1994. Influence of stearic acid on cholesterol metabolism relative to other long chain fatty acids. Am J Clin Nutr. 60:986S–90S.
Gu Y.F., Chen Y., Hammond E.G. (1994). Use of Cyclic Anhydrides to Remove Cholesterol and Other Hydroxyl Compounds form Fats and Oils. J. Am. Oil Chem. Soc 71, 1205-1209.
Guardiola F., Bou R., Boatella J., Codony R. 2004. Analysis of sterol oxidation products in foods. J Assoc Off Anal Chem 87, 441-466.
Hara A., Radin N.S. (1978). Lipid extraction of tissues with a low-toxicity solvent. Anal. Biochem 90: 420-426.
Hayes K.C., Khosla P. 1992. Dietary fatty acid thresholds and cholesterolemia. FASEB J. 6:2600–2607.
Heck J.M., van Valenberg H.J., Dijkstra J., van Hooijdonk A.C. 2009. Seasonal variation in the Dutch bovine raw milk composition. J Dairy Sci 92:4745–55.
Higley N.A., Taylor, S.L., Herian, A.M. and Lee, K. (1986). Cholesterol Oxides in Processed Meats. Meat Sci 16:175-188.
Hunter J.E., Zhang, J., KrisEtherton P.M. 2010. Cardiovascular disease risk of dietary stearic acid compared with trans, other saturated, and unsaturated fatty acids: a systematic review. Am J Clin Nutr. 91:46–63.
Hurst W.J., Aloe M.D., Martin R.B. (1983). High performance liquid chromatographic analysis of cholesterol in milk. J. Dairy Sci 66, 21922194.
Itoh I., Tamura T., Matsumoto T. 1973. Sterol composition of 19 vegetable oils. J. Am. Oil Chem. Soc 50: 122–125.
Javitt N.B. 2008. Oxysterols: novel biologic roles for the 21st century. Steroids 73, 149–157.
Jenness R., Patton S. 1959. Principles of Dairy Chemistry. JohnWiley& Sons. 30-72 p.
Jiang, Z., Cherian G., Robinson F.E., Sim JS. 1990. Effects of feeding cholesterol to laying hens and chicks on cholesterol metabolism in pre- and post hatch chicks. Poult Sci 69: 1694-1701.
Kawakami, A., Yoshida, M. 2005. Remnant lipoproteins and atherogenesis. J Atheroscler Thromb. 12:73–6.
Kovacs M.I., Anderson W.E., Ackman R.G., 1979. A simple method for the determination of cholesterol and some plant sterols in fishery based food products. J. Food Sci 44: 1299-1305.
Lanzani A., Bondioli P, Mariani C, Folegatti L, Ventunni S, Fedeli E, Barreteau P. (1994). A New Short-Path Distillation System Applied to the Reduction of Cholesterol in Butter and Lard. Journal of American Oil Chemists’ Society, 71: 609-614.
Lebovics V.K. 2002. Determination of cholesterol oxidation products by thin-layer chromatography. In: Guardiola F, Dutta PC, Codony R, Savage GP. Cholesterol and phytosterol oxidation products: Analysis, occurrence, and biological effects, eds. Champaign, Illinois: AOCS Press. p 101-113.
Lecerf J.M. 2009. Fatty acids and cardiovascular disease. Nutr Rev. 67:273–83.
Lercker G., Rodriguez-Estrada M. (2002). Cholesterol oxidation mechanisms. In Guardiola F, Dutta PC, Codony R, Savage GP. Editors. Cholesterol and phytosterol oxidation products: Analysis, occurrence, and biological effects. Champaign, Illinois: AOCS Press. p 1-25.
Li, S., Parish E., (1998). The chemistry of waxes and sterols. In Akoh CC, Min DB. Editors. Food Lipids. New York: Dekker Inc. p89–114.
Lin C.Y., Huo C., Kuo L.K., Hiipakka R.A., Jones R.B., Lin H.P., Hung Y.W., Su L.C., Tseng JC, Kuo YY, Wang YL, Fukui Y, Kao YH, Kokontis JM, Yeh CC, Chen LY, Yang SD, Fu HH, Chen YW, Tsai KK, Chang JY, Chuu CP. 2013.
Cholestane-3 beta, 5 alpha, 6 beta-triol suppresses proliferation, migration, and invasion of human prostate cancer cells. PLoS One 8.
LindmarkMånsson H., Fondén R., Pettersson H.E. 2003. Composition of Swedish dairy milk. Int Dairy J 13:409–25.
Liu C, Yang X.V., Wu J, Kuei C., Mani N.S., Zhang L., Yu, J., Sutton S.W., Qin N., Banie H., Karlsson L., Sun S., Lovenberg T.W. 2011b. Oxysterols direct B-cell migration through EBI2. Nature 475, 519–523.
Liu Y., Wang J., Zhang R, Zhang Y., Xu Q., Zhang J. 2009. A good response to oil with medium and Long chain fatty acids in body fat and blood lipid profiles of male hypertriglyceridemic subjects. Asia Pac J Clin Nutr 18:351–8.
Luby J., Gray J., Harte B., Ryan T. 1986b. Photo oxidation of cholesterol in butter. J. Food Sci 51: 904–907.
Makwana T. (2007). Development of a method For Cholesterol Estimation in Milk Fat Using Non Enzymatic Diagnostic kit. 8-23.
Malgrange B., Varela-Nieto I., de Medina P., Paillasse M.R. 2015. Targeting cholesterol homeostasis to fight hearing loss: a new perspective. Front. Aging Neurosci. 7.
Martins I.J., Berger T., Sharman M.J., Verdile G., Fuller S.J., Martins R.N. 2009. Cholesterol metabolism and transport in the pathogenesis of Alzheimer’s disease. J. Neurochem. 111, 1275–1308.
Maxfield, F.R., Tabas, I., 2005. Role of cholesterol and lipid organization in disease. Nature 438, 612–621.
McCluskey, Devery R., (1993). Validation of Chromatographic Analysis of Cholesterol Oxides in Dried Foods. Tren. Food Sci. Technol 4, 175-178.
Mensink R.P., Zock P.L., Kester A.D., Katan M.B. 2003. Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a metaanalysis of 60 controlled trials. Am J Clin Nutr. 77:1146–55.
Micich T.J., Foglia T.A., Holsinger V.H. (1992). Polymer-Supported Saponins: An Approach to Cholesterol Removal from Butteroil. Journal of Agricultural and Food chemistry, 40, 1321-1325.
MotardBelanger A., Charest A., Grenier G, Paquin P., Chouinard Y., Lemieux S. 2008.Study of the effect of trans fatty acids from ruminants on blood lipids and other risk factors for cardiovascular disease. Am J Clin Nutr 87:593–9.
Nagao K, Yanagita T. 2010. Mediumchain fatty acids: functional lipids for the prevention and treatment of the metabolic syndrome. Pharmacol Res 61:208–12.
Nagaoka S., Kanamaru Y., Kuzuya Y., Kojima T., Kuwata T. 1992.Comparative studies on the serum cholesterol lowering action of whey protein and soyprotein in rats. Biosci Biotechnol Biochem 56:1484–5.
Nestel P.J., Chronopulos A., Cehun M. 2005. Dairy fat in cheese raises LDL cholesterol less than that in butter in mildly hypercholesterolaemic subjects. Eur J Clin Nutr 59:1059–63.
Newkirk D.R., Sheppard A.J. 1981. HPLC determination of cholesterol in foods. J Assoc Off Anal Chem 64: 54-57.
Nielsen J., Olsen C., Jensen C., Skibsted L. 1995.Cholesterol oxidation in butter and dairy spread during storage. J Dairy Res 63:159–167.
Nourooz-Zadeh J., Appelqvist L. 1988a. Cholesterol oxides in Swedish foods and food ingredients: milk powder products. J. Food Sci 53:74–79.
Oakenfull D.G., Sidhu G.S. 1991. Cholesterol reduction. Commonwealth Scientific and Industrial Research Organization, assignee. Int. Pat. No. WO 91/11114.
Oh HI, Shin TS, Chang EJ. 2001. Determination of cholesterol in milk and dairy products by high performance liquid chromatography. Asian-Australas J Anim Sci 14(10): 1465-1469.
Pal S., Ellis V., Dhaliwal S. 2010. Effects of whey protein isolate on body composition, lipids, insulin and glucose in overweight and obese individuals. Br J Nutr Apr 9:1–8. [Epub ahead of print]
Pantulu P, Murthy M. 1982. Lipid composition of skimmed milk and whey. Asian Journal of Dairy Research, 1(1):17-20.
Paradkar M.M., Irudayaraj J. 2002. Determination of cholesterol in dairy products by infrared techniques: FT-IR method. Indian J. Technol 55(3), 127-138
PerezMartinez P., Ordovas J.M., GarciaRios A, DelgadoLista J., DelgadoCasado N., CruzTeno C. 2009.Consumption of diets with different type of fat influences triacylglycerolsrich lipoproteins particle number and size during the postprandial state. Nutr Metab Cardiovasc Dis.
Pie J, Spahis K, Seillan C. 1990. Evaluation of oxidative degradation of cholesterol in food and food ingredients: identification and quantification of cholesterol oxides. J. Agric. Food Chem 38: 973–979.
Prasad R., Pandita N.N. 1987. Variations in the cholesterol content of dairy fat. J Dairy Sci 40(1), 55-57.
Punwar J.K. 1975. Gas-liquid chromatographic determination of total cholesterol in multicomponent foods. J Assoc Off Anal Chem 58(4): 804-810.
Raguz M., Mainali L, Widomska J., Subczynski W. 2011. The immiscible cholesterol bilayer domain exists as an integral part of phospholipid bilayer membranes. Biochim. Biophys. Acta 1808(4): 1072-1080.
Rantham Prabhakara J.P., Feist G., Thomasson S., Thompson A., Schommer E., Ghribi O. 2008. Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on tyrosine hydroxylase and alpha-synuclein in human neuroblastoma SH-SY5Y cells. J. Neurochem 107, 1722–1729.
Riccomini, M. A., Wick, C., Peterson, A, Jimenez-Flores, R. and Richardson, T. (1990) Cholesterol removal from cream and anhydrous milk fat using saponins. J. Dairy Sci. 73(1): 107
Rodriguez IR, Larrayoz IM. 2010. Cholesterol oxidation in the retina: implications of 7KCh formation in chronic inflammation and age-related macular degeneration. J. Lipid Res 51, 2847–2862.
Schlimme E, Kiel D. (1989). Removal of cholesterol from milk fat. European Dairy Magazine, 12-21.
Schmarr H.G., Gross H.B., Shibamoto T. 1996. Analysis of polar cholesterol oxidation products: evaluation of a new method involving trans esterification, solid phase extraction, and gas chromatography. J. Agric. Food. Chem 44, 512–517.
Singh I, Gupta M.P. 1982. Physico-chemical characteristics of ghee prepared from goat milk. Asian Journal of Dairy Research, 1: 201-205.
SiriTarino P.W., Sun Q., Hu F.B., Krauss R.M. 2010. Met analysis of prospective cohort studies evaluating the association of saturated fat with cardiovascular disease. Am J Clin Nutr 91:535–46.
Sjogren P, Rosell M, SkoglundAndersson C, Zdravkovic S, Vessby B, de Faire U. 2004. Milkderived Fatty acids are associated with a more favorable LDL particle size distribution in healthy men. J Nutr. 134:1729– 35.
Sottero B., Gamba P., Gargiulo S., Leonarduzzi G., Poli G. 2009. Cholesterol oxidation products and disease: an emerging topic of interest in medicinal chemistry. Curr. Med. Chem 16, 685–705.
Stahelin H.B., Ritzel G.1979. Effect of whey on plasma lipids. Int J Vitam Nutr Res. 49:229–30.
Stonge M.P., Farnworth E.R., Jones P.J. 2000. Consumption of fermented and no fermented dairy products: effects on cholesterol concentrations and metabolism. Am J Clin Nutr 71:674–81.
Tai C., Chen Y., Chen B. 2000. Analysis, Formation and Inhibition of Cholesterol Oxidation Products in Foods: An Overview. J FOOD DRUG ANAL 8(1), 1-15.
Tholstrup T., Ehnholm C., Jauhiainen M., Petersen M., Hoy C.E., Lund P. 2004. Effects of medium chain Fatty acids and oleic acid on blood lipids, lipoproteins, glucose, insulin, and lipid transfer protein activities. Am J Clin Nutr 79:564–9.
Tsui I.C. 1989. Rapid determination of total cholesterol in homogenized milk. J Assoc Off Anal Chem 72(3): 421-424.
Tylkin X.B., Grishina V.E., Suidovskii A. (1975). Photometric investigation of the contents of fat soluble vitamins and cholesterol in dairy products. Tovarovedenie, 8, 42. (cf. DSA 1976(38), 1879).
Ubhayasekera S., Verlryen T., Data P. 2004. Evaluation of GC-MS methods for the analysis of cholesterol oxidation products. Food Chemistry 84, 149-157.
Ulberth F., Buchgraber M. 2002. Extraction and purification of cholesterol oxidation products. In Guardiola F, Dutta PC, Codony R, Savage GP. (Eds.), Cholesterol and phytosterol oxidation products: Analysis, occurrence, and
biological effects. Champaign, Illinois: AOCS Press. p 26-49
VanElswyk M.E., Shake L.S., Hargis P.S. 1991. Research note: Evaluation of two extraction methods for the determination of egg yolk cholesterol. Poult Sci 70: 1258-1260.
Vanzetti G. 1964. Methods photometriques de dosage du cholesterol dans le serum. Clin. Chim. Acta 10: 389.
Vejux A., Lizard G. 2009. Cytotoxic effects of oxysterols associated with human diseases: induction of cell death (apoptosis and/or oncosis), oxidative and inflammatory activities, and phospholipidosis. Mol. Aspects Med 30, 153–170.
Vyshemirskii F.A., Silin V.M., Poyarkova G.S., Vergelesov V.M., Rashevskaya T. (1977). Trudy Vsessoyuzuyi Nauchnoissle-dovatel’skii Institut Maslodel’noi Syrodel’noi Promushlemmosti, 21(62) (cf. DSA 1982(42), 1170).
Windous A. 1910. Uberdie quantitative bestimmung des cholesterins undder cholesterinester in einigen normalen und pathologischen nieren. J. Physs Chem 65: 110.
Wrezel P.W., Krishnmurthy R. G., Hasenhuettl G.L. (1992). Method for Removing Cholesterol from Edible Oils, U.S. Patent No. 5128162.
Xian sheng W, Hung T.V., Drew P. G, Versteeg K. (1990). Enzymatic Degradation of Cholesterol in Milk. Aust J Dairy Technol 45(2), 50-52.
Xiang Y., Tang J.J. , Tao W.Y., Cao X.Z., Song B.L., Zhong J. 2015. Identification of cholesterol 25-Hydroxylase as a novel host restriction factor and a part of the primary innate immune responses against hepatitis C virus infection. J. Virol 89, 6805–6816.
Xu, X.H., Li R.K, Chen J., Chen P., Ling X.Y., Rao P. F. (2002). Quantification of cholesterol in foods using non-aqueous capillary electrophoresis. J. Chromatogr B 768(2), 369-373.
Yen, G.C., Tsai, L.J., (1995). Cholesterol removal from a Lard-Water Mixture with β-Cyclodextrin. J. Food Sci 60, 561-565.
Zarrouk, A, Vejux, A., Mackrill, J., O’Callaghan, Y, Hammami, M., O'Brien N., Lizard, G., 2014.
Involvement of oxysterols in age-related diseases and ageing processes. Ageing Res. Rev 18, 148–162.
Zubillaga, M.P., Maerker, G., (1991). Quantification of 3 Cholesterol Oxidation-Products in Raw Meat and Chicken. J. Food Sci 56: 1194-1196.
This work is licensed under a CC BY-SA 4.0 international