Identification and quantitative analysis of β-sitosterol oxides in vegetable oils by capillary gas chromatography-mass spectrometry

Steroids

Volumn 70, Issue 13, 2005, Pages 896-906

  Zhang, Xin ^a   Julien David, Diane ^a   Miesch, Michel ^a   Geoffroy, Philippe ^a   Raul, Francis ^b   Roussi, Stamatiki ^b   Aoudé Werner, Dalal ^c   Marchioni, Eric ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b IRCAD   (France)

^c Aerial   (France)

Author keywords

Sitosterol oxides; Gas chromatography mass spectrometry (GC MS); Oil; Quantification; Selected ion monitoring (SIM) mode; Thermal oxidation

Indexed keywords

5,6ALPHA EPOXYSITOSTEROL; 5,6BETA EPOXYSITOSTEROL; 5ALPHA,6BETA DIHYDROXYSITOSTEROL; 7 KETOSITOSTEROL; 7ALPHA HYDROXYSITOSTEROL; 7BETA HYDROXYSITOSTEROL; BETA SITOSTEROL OXIDE; OLIVE OIL; PHYTOSTEROL; SITOSTEROL DERIVATIVE; SUNFLOWER OIL; UNCLASSIFIED DRUG; VEGETABLE OIL;

ANALYTIC METHOD; ARTICLE; CAPILLARY GAS CHROMATOGRAPHY; HEATING; ION MONITORING; MASS SPECTROMETRY; OXIDATION; QUANTITATIVE ANALYSIS; SAPONIFICATION; SOLID PHASE EXTRACTION; SOLVENT EXTRACTION; TEMPERATURE DEPENDENCE;

GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HEAT; OXIDES; PHYTOSTEROLS; PLANT OILS; SITOSTEROLS;

HELIANTHUS;

EID: 27644542338     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.06.004     Document Type: Article

References (40)

1. A.S. Csallany, S.E. Kindom, P.B. Addis, and L.H. Lee HPLC method for quantitation of cholesterol and four of its major oxidation products in muscle and liver tissues Lipids 24 1989 645 651
2. G.G. Daly, E.T. Finocchiaro, and T. Richardson Characterization of some oxidation products of β-sitosterol J Agric Food Chem 31 1983 46 50
3. R.A. Ferrari, E. Schulte, W. Esteves, L. Bruhl, and K.D. Mukherjee Minor constituents of vegetable oils during industrial processing J Am Oil Chem Soc 73 1996 587 592
4. D. Lütjohann Sterol autoxidation: from phytosterols to oxyphytosterols Br J Nutr 91 2004 3 4
5. D.W. Russell, and K.D. Setchell Bile acid biosynthesis Biochemistry 31 1992 4737 4749
6. L.L. Smith Cholesterol autoxidation: 1981-1986 Chem Phys Lipids 44 1987 87 125
7. L.L. Smith Review of progress in sterol oxidation: 1987-1995 Lipids 31 1996 453 487
8. GJ. Schroepfer Jr. Oxysterols: modulators of cholesterol metabolism Physiol Rev 80 2000 361 554
9. F. Guardiola P.C. Dutta G.P. Savage R. Codony Cholesterol and phytosterol oxidation products in foods and biological samples: analysis, occurrence and biological effects 2002 AOCS Press Champaign, IL
10. F. Guardiola, R. Codony, P.B. Addis, M. Rafecas, and J. Boatell Biological effects of oxysterols: current status Food Chem Toxicol 34 1996 193 211
11. A.J. Brown, and W. Jessup Oxysterols and atherosclerosis Atherosclerosis 142 1999 1 28
12. W.H. Ling, and PJ.H. Jones Dietary phytosterols: a review of metabolism, benefits and side effects Life Sci 57 1995 195 206
13. V. Piironen, D.G. Lindsay, T.A. Miettinen, J. Toivo, and A.M. Lampi Plant sterols: biosynthesis, biological function and their importance to human nutrition J Sci Food Agric 80 2000 939 966
14. R.A. Moreau, B.D. Whitaker, and K.B. Hicks Phytosterol, phytostanols, and their conjugates in food: structural diversity, quantitative analysis, and health-promoting uses Prog Lipid Res 41 2002 457 500
15. C. Adcox, L. Boyd, L. Oehrl, J. Allen, and G. Fenner Comparative effects of phytosterol oxides and cholesterol oxides in cultured macrophage-derived cell lines J Agric Food Chem 49 2001 2090 2095
16. A. Grandgirard, L. Martine, and L. Demaison Oxyphytosterols are present in plasma of healthy human subjects Br J Nutr 91 2004 101 106
17. H. Shan, J. Pang, S. Li, T.B. Chiang, W.K. Wilson, and GJ. Schroepfer Jr. Chromatographic behaviour of oxygenated derivatives of cholesterol Steroids 68 2003 221 233
18. P.C. Dutta Studies on phytosterol oxides. II. Content in some vegetable oils and in French fries prepared in these oils. J Am Oil Chem Soc 74 1997 659 666
19. J. Plat, H. Brzezinka, D. Lütjohann, R.P. Mensink, and K. Bergmann 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
20. A.M. Lampi, L. Juntunen, J. Toivo, and V. Piironen Determination of thermo-oxidation products of plant sterols. J Chromatogr B 777 2002 83 92
21. L. Johnsson, and P.C. Dutta Characterisation of side-chain oxidation products of sitosterol and campesterol by chromatographic and spectroscopic methods J Am Oil Chem Soc 80 2003 767 776
22. A. Grandgirard, L. Martine, C. Joffre, P. Juaneda, and O. Berdeaux Gas chromatographic separation and mass spectrometric identification of mixtures of oxyphytosterols and oxycholesterol derivatives. Application to a phytosterol-enriched food J Chromatogr A 1040 2004 239 250
23. 2-labeled oxidation products from the phytosterols β-sitosterol and stigmasterol Anal Biochem 325 2004 107 116
24. L. Johnsson, and P.C. Dutta Separation of phytosterol oxidation products by combination of different polarity gas chromatography capillary columns J Chromatogr A 1064 2005 213 217
25. F. Guardiola, R. Bou, J. Boatella, and R. Codony Analysis of sterol oxidation products in foods J AOAC Int 87 2004 441 466
26. U. Diczfalusy Analysis of cholesterol oxidation products in biological samples J AOAC Int 87 2004 467 473
27. Regueiro JAG, and C. Maraschiello 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
28. E. Turchetto, G. Lercker, and R. Bortolomeazzi Oxysterol determination in selected coffees Toxicol Ind Health 9 1993 519 527
29. X. Zhang, P. Geoffroy, M. Miesch, D. Julien-David, F. Raul, and D. Aoudé-Werner Gram-scale chromatographic purification of β-sitosterol. Synthesis and characterization of β-sitosterol oxides Steroids 70 2005 886 895
30. R. Bortolomeazzi, M.D. Zan, L. Pizzale, and L.S. Conte Mass spectrometry characterization of the 5α, 7α, and 7β-hydroxy derivatives of β-sitosterol, campesterol, stigmasterol and brassicasterol J Agric Food Chem 47 1999 3069 3074
31. P.C. Dutta, and L.Å. Appelqvist Studies on phytosterol oxides. I. Effect of storage on the content in potato chips prepared in different vegetable oils. J Am Oil Chem Soc 74 1997 647 657
32. L. Pizzoferrato, S. Nicoli, and C. Lintas GC-MS characterization and quantification of sterols and cholesterol oxidation products Chromatographia 35 1993 269 274
33. R. Bortolomeazzi, F. Cordaro, L. Pizzale, and L.S. Conte Presence of phytosterol oxide in crude vegetable oils and their fate during refining J Agric Food Chem 51 2003 2394 2401
34. AJ.H. Louter Determination of plant sterol oxidation products in plant sterol enriched spreads, fat blend, and plant sterol concentrates J AOAC Int 87 2004 485 492
35. J.E. Pie, K. Spahis, and C. Seillan Evaluation of oxidative degradation of cholesterol in food and food ingredients: identification and quantification of cholesterol oxides J Agric Food Chem 38 1990 973 979
36. J.E. Pie, K. Spahis, and C. Seillan Cholesterol oxidation in meat products during cooking and frozen storage J Agric Food Chem 39 1991 250 254
37. S.W. Park, F. Guardiola, S.H. Park, and P.B. Addis Kinetic evaluation of 3β-hydroxycholest-5-en-7-one (7-ketocholesterol) stability during saponification J Am Oil Chem Soc 73 1996 623 629
38. S.J.K.A. Ubhayasekera, T. Verleyen, and P.C. Dutta Evaluation of GC and GC-MS methods for the analysis of cholesterol oxidation products Food Chem 84 2004 149 157
39. K. Osada, T. Kodama, K. Yamada, and M. Sugano Oxidation of cholesterol by heating J Agric Food Chem 41 1993 1198 1202
40. S.P. Kochhar Influence of processing on sterols of edible vegetable oils Prog Lipid Res 22 1983 161 188