Artifact generation and monitoring in analysis of cholesterol oxide products

Analytical Biochemistry

Volumn 388, Issue 1, 2009, Pages 1-14

  Busch, T P ^a   King, A J ^b  

^a Oscar Mayer Foods Corp   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY;

CHOLESTEROL OXIDES;

CHEMISTRY;

CHOLESTEROL; CHOLESTEROL DERIVATIVE;

ARTIFACT; CHEMICAL ANALYSIS; CHEMICAL REACTION; HUMAN; LIPID ANALYSIS; LIPID OXIDATION; NONHUMAN; PRIORITY JOURNAL; REVIEW;

EID: 63149190201     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2008.12.034     Document Type: Review

References (102)

1. Smith L.L. Cholesterol Autoxidation (1981), Plenum, New York
2. Smith L.L. Cholesterol autoxidation 1981-1986. Chem. Phys. Lipids 44 (1987) 87-126
3. Smith L.L., and Johnson B.H. Biological activities of oxysterols. Free Radic. Biol. Med. 7 (1989) 285-332
4. Peng S.-K., Hu B., and Morin R.J. Effects of cholesterol oxides on atherogenesis. In: Peng S.-K., and Morin R.J. (Eds). Biological Effects of Cholesterol Oxides (1992), CRC Press, Boca Raton, FL 167-190
5. Peng S.-K., and Morin R.J. Effects of cholesterol oxides on cell membranes. In: Peng S.-K., and Morin R.J. (Eds). Biological Effects of Cholesterol Oxides (1992), CRC Press, Boca Raton, FL 125-146
6. Peng S.-K., Sevanian A., and Morin R.J. Cytotoxicity of cholesterol oxides. In: Peng S.-K., and Morin R.J. (Eds). Biological Effects of Cholesterol Oxides (1992), CRC Press, Boca Raton, FL 147-166
7. Morin R.J., Hu B., and Peng S.-K. Effects of cholesterol oxides on cholesterol metabolism. In: Peng S.-K., and Morin R.J. (Eds). Biological Effects of Cholesterol Oxides (1992), CRC Press, Boca Raton, FL 103-124
8. Morin R.J., Hu B., Peng S.-K., and Sevanian A. Cholesterol oxidation and cancer. In: Peng S.-K., and Morin R.J. (Eds). Biological Effects of Cholesterol Oxides (1992), CRC Press, Boca Raton, FL 191-202
9. Bosinger S., Luf W., and Brandl E. Oxysterols: their occurrence and biological effects. Int. Dairy J. 3 (1993) 1-33
10. Smith L.L. Review of progress in sterol oxidations: 1987-1995. Lipids 31 (1996) 453-487
11. Guardiola F., Codony R., Addis P.B., Rafecas M., and Boatella J. Biological effects of oxysterols: current status. Food Chem. Toxicol. 34 (1996) 193-211
12. Linseisen J., and Wolfram G. Origin, metabolism, and adverse health effects of cholesterol oxidation products. Fett/Lipid 100 (1988) 211-218
13. Brown A.J., and Jessup W. Oxysterols and atherosclerosis. Atherosclerosis 142 (1999) 1-28
14. Schroepfer Jr. G.J. Oxysterols: modulators of cholesterol metabolism and other processes. Physiol. Rev. 80 (2000) 361-554
15. Colles S.M., Maxson J.M., Carlson S.G., and Chisolm G.M. Oxidized LDL-induced injury and apoptosis in atherosclerosis: potential roles for oxysterols. Trends Cardiovasc. Med. 11 (2001) 131-138
16. Leonarduzzi G., Sottero B., and Poli G. Oxidized products of cholesterol: dietary and metabolic origin, and proatherosclerotic effects (review). J. Nutr. Biochem. 13 (2002) 700-710
17. Björkhem I., and Diczfalusy U. Oxysterols: friends, foes, or just fellow passengers?. Arterioscler. Thromb. Vasc. Biol. 22 (2002) 734-742
18. Park P.S.W., and Addis P.B. Cholesterol oxide content of foods. In: Peng S.-K., and Morin R.J. (Eds). Biological Effects of Cholesterol Oxides (1992), CRC Press, Boca Raton, FL 71-88
19. Paniangvait P., King A.J., Jones A.D., and German B.G. Cholesterol oxides in foods of animal origin. J. Food Sci. 60 (1995) 1159-1174
20. Appelqvist L.A. Oxidized sterols. Bull. Int. Dairy Fed. 315 (1996) 52-58
21. Yan P.S. Cholesterol oxidation products: their occurrence and detection in our foodstuffs. In: Jackson L.S., Knize M.G., and Morgan J.N. (Eds). Impact of Processing on Food Safety (1999), Kluwer Academic/Plenum, New York 79-98
22. Lercker G., and Rodriguez-Estrada M.T. Cholesterol oxidation: presence of 7-ketocholesterol in different food products. J. Food Compos. Anal. 13 (2000) 625-631
23. Savage G.P., Dutta P.C., and Rodriguez-Estrada M.T. Cholesterol oxides: their occurrence and methods to prevent their generation in foods. Asia Pac. J. Clin. Nutr. 11 (2002) 72-78
24. Guardiola F., Bou R., Boatella J., and Codony R. Analysis of sterol oxidation products in foods. J. AOAC Int. 87 (2004) 441-466
25. Dutta P.C. Accurate and reproducible methods for analysis of sterol oxidation products in foods: an overview. J. AOAC Int. 87 (2004) 439-440
26. Park P.S.W., and Addis P.B. Methods of analysis of cholesterol oxides. In: Peng S.-K., and Morin R.J. (Eds). Biological Effects of Cholesterol Oxides (1992), CRC Press, Boca Raton, FL 33-70
27. Guardiola F., Jordan A., Grau A., Garcia S., Boatella J., Rafecas M., and Codony R. Recent methodological advances in oxysterol determination. In: Pandalai S.G. (Ed). Recent Research Developments in Oil Chemistry (1998), Transworld Research Network, Trivandru 77-88
28. Bodin K., and Diczfalusy U. Analysis of cholesterol oxidation products in plasma, tissues, and food. Eur. J. Lipid Sci. Technol. 104 (2002) 435-439
29. Diczfalusy U. Analysis of cholesterol oxidation products in biological samples. J. AOAC Int. 87 (2004) 467-473
30. Kudo K., Emmons G.T., Casserly E.W., Via D.P., Smith L.C., St. Pyrek J., and Schroepfer Jr. G.J. Inhibitors of sterol synthesis. Chromatography of acetate derivatives of oxygenated sterols. J. Lipid Res. 30 (1989) 1097-1111
31. Breuer O., and Bjorkhem I. Simultaneous quantification of several cholesterol autoxidation and monohydroxylation products by isotope-dilution mass spectrometry. Steroids 55 (1990) 185-192
32. Wasilchuk B.A., Le Quesne P.W., and Vouros P. Monitoring cholesterol autoxidation processes using multideuterated cholesterol. Anal. Chem. 64 (1992) 1077-1087
33. Dzeletovic S., Breuer O., Lund E., and Diczfalusy U. Determination of cholesterol oxidation products in human plasma by isotope dilution-mass spectrometry. Anal. Biochem. 225 (1995) 73-80
34. 7]cholesterol to monitor cholesterol autoxidation artifacts. J. Agric. Food Chem. 43 (1995) 935-941
35. Park P.W., Guardiola F., Park S.H., and Addis P.B. Kinetic evaluation of 3-β-hydroxycholest-5-en-7-one (7-ketocholesterol) stability during saponification. J. Am. Oil Chem. Soc. 73 (1996) 623-629
36. Dionisi F., Golay P.A., Aeschlimann J.M., and Fay L.B. Determination of cholesterol oxidation products in milk powders: methods comparison and validation. J. Agric. Food Chem. 46 1998 (1998) 2227-2233
37. Bascoul J., Domergue N., Olle M., and Crastes de Paulet A. Autoxidation of cholesterol in tallows heated under deep frying conditions: evaluation of oxysterols by GLC and TLC-FID. Lipids 2 (1986) 383-387
38. Nourooz-Zadeh J. Determination of the autoxidation products from free or total cholesterol: a new multistep enrichment methodology including the enzymatic release of esterified cholesterol. J. Agric. Food Chem. 38 (1990) 1667-1673
39. Guardiola F., Codony R., Rafecas M., and Boatella J. Comparison of three methods for the determination of oxysterols in spray-dried egg. J. Chromatogr. A 705 (1995) 289-304
40. Garcia Regueiro J.A., and Maraschiello C. Procedure for the determination of eight cholesterol oxides in poultry meat using on-column and solvent venting capillary gas chromatography. J. Chromatogr. A 764 (1997) 279-293
41. Ulberth F., and Roessler D. Comparison of solid-phase extraction methods for the cleanup of cholesterol oxidation products. J. Agric. Food Chem. 46 (1998) 2634-2637
42. Rodriguez-Estrada M.T., Costa A., Pelillo M., Caboni M.F., and Lercker G. Comparison of cholesterol oxidation product preparation methods for subsequent gas chromatographic analysis. J. AOAC Int. 87 (2004) 474-480
43. Ubhayasekera S.J.K.A., Verleyen T., and Dutta P.C. Evaluation of GC and GC-MS methods for the analysis of cholesterol oxidation products. Food Chem. 84 (2004) 149-157
44. P.C. Dutta, M.F. Caboni, U. Diczfalusy, F. Dionisi, S. Dzeletovic, A. Grandgirard, F. Guardiola, J. Kumpulainen, V.K. Lebovics, J.M. Pihlava, M.T. Rodriguez-Estrada, F. Ulberth, Measurements of cholesterol oxides in foods: results of an interlaboratory comparison study, in: Natural Antioxidants and Anticarcinogens in Nutrition Health and Disease, Royal Society of Chemistry, Cambridge, 1999, pp. 309-315.
45. Appelqvist L.A., Addis P., Bjorkhem I., Bosset J.O., Caboni M.F., Dutta P., Grandgirard A., Guardiola F., Hau L.B., Nielsen J.H., Hugget A., Hwang L.S., Kumpulainen J., McCluskey S., Ohshima T., Przbylski R., Sevanian A., and Yan P. Harmonization of methods for analysis of cholesterol oxides in foods-the first portion of a long road toward standardization: interlaboratory study. J. AOAC Int. 87 2004 (2004) 511-519
46. Smith L.L. The oxidation of cholesterol. In: Peng S.-K., and Morin R.J. (Eds). Biological Effects of Cholesterol Oxides (1992), CRC Press, Boca Raton, FL 7-32
47. Nourooz-Zadeh J., and Appelqvist L.A. Cholesterol oxides in Swedish foods and food ingredients: fresh eggs and dehydrated egg products. J. Food Sci. 52 (1987) 57-62 67
48. Pie J.E., Spahis K., and Seillan C. Cholesterol oxidation in meat products during cooking and frozen storage. J. Agric. Food Chem. 39 (1991) 250-254
49. Dyer R.G., Hetherington C.S., Alberti K.G.M.M., and Laker M.F. Simultaneous measurement of phytosterols (campesterol and beta-sitosterol) and 7-ketocholesterol in human lipoproteins by capillary column gas chromatography. J. Chromatogr. B 663 (1995) 1-7
50. Boselli E., Velazco V., Caboni M.F., and Lercker G. Pressurized liquid extraction of lipids for the determination of oxysterols in egg-containing food. J. Chromatogr. A 917 (2001) 239-244
51. Park S.W., and Addis P.B. Identification and quantitative estimation of oxidized cholesterol derivatives in heated tallow. J. Agric. Food Chem. 34 (1986) 653-659
52. Nielsen J.H., Olsen C.E., Duedahl C., and Skibsted L.H. Isolation and quantification of cholesterol oxides in dairy products by selected ion monitoring mass spectrometry. J. Dairy Res. 62 (1995) 101-113
53. T.P. Busch, A.J. King. Artifact Generation and Monitoring in Analysis of Cholesterol Oxide Products, Ph.D. thesis, University of California, Davis, Davis, CA, 2006.
54. van de Bovenkamp P., Kosmeijer-Schuil T.G., and Katan M.B. Quantification of oxysterols in Dutch foods: egg products and mixed diets. Lipids 23 (1988) 1079-1085
55. Ibrahim N., Unklesbay N., Kapila S., and Puri R.K. Cholesterol content of restructured pork/soy hull mixture. J. Food Sci. 5 (1990) 1488-1490
56. Fletouris D.J., Botsoglou N.A., Psomas I.E., and Mantis A.I. Rapid determination of cholesterol in milk and milk products by direct saponification and capillary gas chromatography. J. Dairy Sci. 81 (1988) 2833-2840
57. Lampi A.-M., Juntunen L., Toivo J., and Piironen V. Determination of thermo-oxidation products of plant sterols. J. Chromatogr. B 777 (2002) 83-92
58. Plat J., Brzezinka H., Lutjohann D., Mensink R.P., and von Bergmann K. Oxidized plant sterols in human serum and lipid infusions as measured by combined gas-liquid chromatography-mass spectrometry. J. Lipid Res. 42 (2001) 2030-2038
59. Leoni V., Lutjohann D., and Masterman T. Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J. Lipid Res. 46 (2005) 191-195
60. Burkard I., Rentsch K.M., and von Eckardstein A. Determination of 24S- and 27-hydroxycholesterol in plasma by high-performance liquid chromatography-mass spectrometry. J. Lipid Res. 45 (2004) 776-781
61. Bortolomeazzi R., Cordaro F., Pizzale L., and Conte L.S. Presence of phytosterol oxides in crude vegetable oils and their fate during refining. J. Agric. Food Chem. 51 (2003) 2394-2401
62. Shan H., Pang J., Li S., Chiang T.B., Wilson W.K., and Schroepfer Jr. G.J. Chromatographic behavior of oxygenated derivatives of cholesterol. Steroids 68 (2003) 221-233
63. Brooks C.J.W., Henderson W., and Steel G. The use of trimethylsilyl ethers in the characterization of natural sterols and steroid diols by gas chromatography-mass spectrometry. Biochim. Biophys. Acta 29 (1973) 431-445
64. Park P.S.W., and Addis P.B. Derivatization of 5α-cholestane-3β,5,6β-triol into trimethylsilyl ether sterol for GC analysis. J. Am. Oil Chem. Soc. 66 (1989) 1632-1634
65. Guardiola F., Codony R., Rafecas M., and Boatella J. Adsorption of oxysterols on different microtube materials during silanization prior to gas chromatographic determination. J. Chromatogr. A 705 (1995) 396-399
66. Missler S.R., Wasilchuk B.A., and Merritt Jr. C. Separation and identification of cholesterol oxidation products in dried egg preparations. J. Food Sci. 50 (1985) 595-598 646
67. Pie J.E., and Seillan C. Oxysterols in cultured bovine aortic smooth muscle cells and in the monocyte-like cell line U937. Lipids 27 (1992) 270-274
68. Dzeletovic S., Babiker A., Lund E., and Diczfalusy U. Time course of oxysterol formation during in vitro oxidation of low density lipoprotein. Chem. Phys. Lipids 78 (1995) 119-228
69. Maerker G., and Unruh Jr. J. Cholesterol oxides, I, isolation and determination of some cholesterol oxidation products. J. Am. Oil Chem. Soc. 63 (1986) 767-771
70. Breuer O. Identification and quantitation of cholest-5-ene-3 beta, 4 beta-diol in rat liver and human plasma. J. Lipid Res. 36 (1995) 2275-2281
71. Björkhem I., Breuer O., Angelin B., and Wikstrom S. Assay of unesterified cholesterol-5,6-epoxide in human serum by isotope dilution mass spectrometry, Levels in the healthy state and in hyperlipoproteinemia. J. Lipid Res. 29 (1988) 1031-1038
72. Guardiola F., Garcia-Cruset S., Bou R., and Codony R. Artifactual oxidation of cholesterol during the analysis of cholesterol oxidation products: protective effect of antioxidants. J. AOAC Int. 87 (2004) 493-498
73. Frankel E.N. Lipid Oxidation (1998), The Oily Press, Dundee
74. Murakami H., Tamasawa N., Matsui J., Yasujima M., and Suda T. Plasma oxysterols and tocopherol in patients with diabetes mellitus and hyperlipidemia. Lipids 35 (2000) 333-338
75. Brown A.J., Dean R.T., and Jessup W. Free and esterified oxysterol: formation during copper-oxidation of low density lipoprotein and uptake by macrophages. J. Lipid Res. 37 (1996) 320-335
76. Hodis H.N., Crawford D.W., and Sevanian A. Cholesterol feeding increases plasma and aortic tissue cholesterol oxide levels in parallel: further evidence for the role of cholesterol oxidation in atherosclerosis. Atherosclerosis 89 (1991) 117-226
77. Kritharides L., Jessup W., Gifford J., and Dean R.T. A method for defining the stages of low-density lipoprotein oxidation by the separation of cholesterol and cholesteryl ester-oxidation products using HPLC. Anal. Biochem. 213 (1993) 79-89
78. Xu Z., Hua N., and Godber J.S. Antioxidant activity of tocopherols, tocotrienols, and gamma-oryzanol components from rice bran against cholesterol oxidation accelerated by 2,2′-azobis(2-methylpropionamidine) dihydrochloride. J. Agric. Food Chem. 49 (2001) 2077-2081
79. Addis P.B., Emanuel H.A., Bergmann S.D., and Zavoral J.H. Capillary GC quantification of cholesterol oxidation products in plasma lipoproteins of fasted humans. Free Radic. Biol. Med. (1989) 179-182
80. Zubillaga M.P., and Maerker G. Quantification of three cholesterol oxidation products in raw meat and chicken. J. Food Sci. 56 (1991) 1194-1196 1202
81. Maraschiello C., Esteve E., and Garcia Regueiro J.A. Cholesterol oxidation in meat from chickens fed alpha-tocopherol- and beta-carotene-supplemented diets with different unsaturation grades. Lipids 33 (1998) 705-713
82. Grau A., Codony R., Grimpa S., Baucells M.D., and Guardiola F. Cholesterol oxidation in frozen dark chicken meat: influence of dietary fat source, and alpha-tocopherol and ascorbic acid supplementation. Meat Sci. 57 (2001) 197-208
83. Grandgirard A., Martine L., Joffre C., Juaneda P., and Berdeaux O. Gas chromatographic separation and mass spectrometric identification of mixtures of oxyphytosterol and oxycholesterol derivatives application to a phytosterol-enriched food. J. Chromatogr. A 1040 (2004) 239-250
84. Staprans L., Pan X.-M., Rapp J.H., and Feingold K.R. Oxidized cholesterol in the diet is a source of oxidized lipoproteins in human serum. J. Lipid Res. 44 (2003) 705-715
85. Li S., Pang J., Wilson W.K., Schroepfer Jr. G.J., and synthesis S. Preparation and characterization of fluorinated and deuterated analogs of oxygenated derivatives of cholesterol. Chem. Phys. Lipids 99 (1999) 86
86. Grandgirard A., Cabaret S., Martine L., and Berdeaux O. New internal standard for quantitative determination of oxyphytosterols by gas chromatography. J. AOAC Int. 87 (2004) 481-484
87. Diestel A., Aktas O., Hackel D., Hake I., Meier S., Raine C.S., Nitsch R., Zipp F., and Ullrich O. Activation of microglial poly(ADP-ribose)-polymerase-1 by cholesterol breakdown products during neuroinflammation: a link between demyelination and neuronal damage. J. Exp. Med. 198 (2003) 1729-1740
88. Sevanian A., Seraglia R., Traldi P., Rossato P., Ursini F., and Hodis H. Analysis of plasma cholesterol oxidation products using gas- and high-performance liquid chromatography/mass spectroscopy. Free Radic. Biol. Med. 17 (1994) 397-409
89. Dyer R.G., Stewart M.W., Mitcheson J., George K., Alberti M.M., and Laker M.F. 7-Ketocholesterol, a specific indicator of lipoprotein oxidation, and malondialdehyde in non-insulin dependent diabetes and peripheral vascular disease. Clin. Chim. Acta 260 (1997) 1-13
90. Osada K., Hoshina S., Nakamura S., and Sugano M. Cholesterol oxidation in meat products and its regulation by supplementation of sodium nitrite and apple polyphenol before processing. J. Agric. Food Chem. 48 (2000) 3823-3829
91. Miwa S., Inouye M., Ohmura C., Mitsuhashi N., Onuma T., and Kawamori R. Relationship between carotid atherosclerosis and erythrocyte membrane cholesterol oxidation products in type 2 diabetic patients. Diabetes Res. Clin. Pract. 61 (2003) 81-88
92. King A.J., and Priesbe T.J. Concerns about methodology and use of 3,5,7-cholestatriene as a marker of oxidative stress. Response to relationship between carotid atherosclerosis and erythrocyte membrane cholesterol oxidation products in type 2 diabetic patients. Diabetes Res. Clin. Pract. 72 (2006) 331-334
93. Boselli E., Caboni M.F., Frega N.G., and Lercker G. Cholesterol oxidation in pasta produced with eggs of different origin. Eur. Food Res. Technol. 218 (2004) 410-414
94. Inouye M., Mio T., and Sumino K. Nilvadipine protects low-density lipoprotein cholesterol from in vivo oxidation in hypertensive patients with risk factors for atherosclerosis. Eur. J. Clin. Pharmacol. 56 (2000) 35-41
95. Miwa S., Watada H., Ohmura C., Tanaka Y., and Kawamori R. Efficacy and safety of once daily gliclazide (20 mg/day) compared with nateglinide. Endocr. J. 51 (2004) 393-398
96. Miwa S., Watada H., Omura C., Takayanagi N., Nishiyama K., Tanaka Y., Onuma T., and Kawamori R. Anti-oxidative effect of fluvastatin in hyperlipidemic type 2 diabetic patients. Endocr. J. 52 (2005) 259-264
97. Louter A.J. Determination of plant sterol oxidation products in plant sterol enriched spreads, fat blends, and plant sterol concentrates. J. AOAC Int. 87 (2004) 485-492
98. Lembcke J., Ceglarek U., Fiedler G.M., Baumann S., Leichtle A., and Thiery J. Rapid quantification of free and esterified phytosterols in human serum using APPI-LC-MS/MS. J. Lipid Res. 46 (2005) 21-26
99. Brunel J.M., Loncle C., Vidal N., Dherbomez M., and Letourneux Y. Synthesis and antifungal activity of oxygenated cholesterol derivatives. Steroids 70 (2005) 907-912
100. Wentworth Jr. P., Nieva J., Takeuchi C., Galve R., Wentworth A.D., Dilley R.B., DeLaria G.A., Saven A., Babior B.M., Janda K.D., Eschenmoser A., and Lerner R.A. Evidence for ozone formation in human atherosclerotic arteries. Science 302 (2003) 1053-1056
101. Smith L.L. Oxygen, oxysterols, ouabain, and ozone: a cautionary tale. Free Radic. Biol. Med. 37 (2004) 318-324
102. Rudzinska M., Korczak J., Gramza A., Wasowicz E., and Dutta P.C. Inhibition of stigmasterol oxidation by antioxidants in purified sunflower oil. J. AOAC Int. 87 (2004) 499-504