Synthesis of 7-hydroperoxycholesterol and its separation, identification, and quantification in cholesterol heated model systems

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 18, 2010, Pages 10226-10230

  Nogueira, Gislaine C ^a   Costa, Bruna Z ^a   Crotti, Antonio E M ^b   Bragagnolo, Neura ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSIDADE DE FRANCA   (Brazil)

Author keywords

APCI LC MS; cholesterol oxides; NMR; thermal degradation

Indexed keywords

APCI-LC-MS; HIGHER TEMPERATURES; HYDROPEROXIDES; INTERMEDIATE COMPOUND; MASS SPECTRA; MODEL SYSTEM; NMR; OXIDATION MECHANISMS; ROOM TEMPERATURE; THERMAL DEGRADATION; THREE PHASIS;

DEGRADATION; MASS SPECTROMETRY; OXYGEN; PHOTOOXIDATION; REACTION INTERMEDIATES;

CHOLESTEROL;

CHOLESTEROL; CHOLESTEROL 7 HYDROPEROXIDE; CHOLESTEROL 7-HYDROPEROXIDE; DRUG DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; HEAT; ISOLATION AND PURIFICATION; KINETICS; PHOTOCHEMISTRY; SYNTHESIS;

CHOLESTEROL; HOT TEMPERATURE; KINETICS; MODELS, CHEMICAL; PHOTOCHEMICAL PROCESSES;

EID: 77956646653     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf102252r     Document Type: Article

References (22)

1. Bascoul, J.; Domergue, N.; Olle, M.; Depaulet, A. C. Autoxidation of cholesterol in tallows heated under deep frying conditions-evaluation of oxysterols by GLC and TLC-FID Lipids 1986, 21, 383-387
2. Caboni, M. F.; Boselli, E.; Messia, M. C.; Velazco, V.; Fratianni, A.; Panfili, G.; Marconi, E. Effect of processing and storage on the chemical quality markers of spray-dried whole egg Food Chem. 2005, 92, 293-303
3. Smith, L. L. Cholesterol autoxidation 1981-1986 Chem. Phys. Lipids 1987, 44, 87-125
4. Guardiola, F.; Codony, R.; Addis, P. B.; Rafecas, M.; Boatella, J. Biological effects of oxysterols: current status Food Chem. Toxicol. 1996, 34, 193-211
5. Smith, L. L. Review of progress in sterol oxidations: 1987-1995 Lipids 1996, 31, 453-487
6. Chien, J. T.; Hsu, D. J.; Chen, B. H. Kinetic model for studying the effect of quercetin on cholesterol oxidation during heating J. Agric. Food Chem. 2006, 54, 1486-1492
7. Chien, J. T.; Huang, D. Y.; Chen, B. H. Kinetic studies of cholesterol oxidation as inhibited by stearylamine during heating J. Agric. Food Chem. 2004, 52, 7132-7138
8. Chien, J. T.; Wang, H. C.; Chen, B. H. Kinetic model of the cholesterol oxidation during heating J. Agric. Food Chem. 1998, 46, 2572-2577
9. Mariutti, L. R. B.; Nogueira, G. C.; Bragagnolo, N. Optimization and validation of analytical conditions for cholesterol and cholesterol oxides extraction in chicken meat using response surface methodology J. Agric. Food Chem. 2008, 56, 2913-2918
10. Mazalli, M. R.; Sawaya, A.; Eberlin, M. N.; Bragagnolo, N. HPLC method for quantification and characterization of cholesterol and its oxidation products in eggs Lipids 2006, 41, 615-622
11. Razzazi-Fazeli, E.; Kleineisen, S.; Luf, W. Determination of cholesterol oxides in processed food using highperformance liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization J. Chromatogr., A 2000, 896, 321-334
12. Kemmo, S.; Ollilainen, V.; Lampi, A. M.; Piironen, V. Determination of stigmasterol and cholesterol oxides using atmospheric pressure chemical ionization liquid chromatography/mass spectrometry Food Chem. 2007, 101, 1438-1445
13. Raith, K.; Brenner, C.; Farwanah, H.; Muller, G.; Eder, K.; Neubert, R. H. H. A new LC/APCI-MS method for the determination of cholesterol oxidation products in food J. Chromatogr., A 2005, 1067, 207-211
14. Rossmann, B.; Thurner, K.; Luf, W. MS-MS fragmentation patterns of cholesterol oxidation products Monatsh. Chem. 2007, 138, 436-444
15. Saldanha, T.; Sawaya, A.; Eberlin, M. N.; Bragagnolo, N. HPLC separation and determination of 12 cholesterol oxidation products in fish: comparative study of RI, UV, and APCI-MS detectors J. Agric. Food Chem. 2006, 54, 4107-4113
16. Beckwith, A. L. J.; Davies, A. G.; Davison, I. G. E.; Maccoll, A.; Mruzek, M. H. The mechanisms of the rearrangements of allylic hydroperoxides: 5α-hydroperoxy-3β-hydroxycholest-6-ene and 7α-hydroperoxy- 3β-hydroxycholest-5-ene J. Chem. Soc., Perkin Trans. 2 1989, 815-824
17. Geiger, P. G.; Thomas, J. P.; Girotti, A. W. Lethal damage to murine L1210 cells by exogenous lipid hydroperoxides: protective role of glutathione-dependent selenoperoxidases Arch. Biochem. Biophys. 1991, 288, 671-680
18. Silverstein, R. M.; Webster, F. X.; Kiemle, D. J. Spectrometric Identification of Organic Compounds, 7 th ed.; Wiley: Indianapolis, IN, 2005.
19. Ponce, M. A.; Ramirez, J. A.; Galagovsky, L. R.; Gros, E. G.; Erra-Balsells, R. Singlet-oxygen ene reaction with 3-substituted stigmastanes. An alternative pathway for the classical Schenck rearrangement J. Chem. Soc., Perkin Trans. 2 2000, 2351-2358
20. McLafferty, F. W.; Turecek, F. Interpretation of Mass Spectra, 4 th ed.; University Science Books: Sausalito, CA, 1993.
21. Kim, S. K.; Nawar, W. W. Parameters influencing cholesterol oxidation Lipids 1993, 28, 917-922
22. Park, S. W.; Addis, P. B. Further investigation of oxidized cholesterol derivatives in heated fats J. Food Sci. 1986, 51, 1380-1381