Ozonation of cholesterol in the presence of ethanol: Identification of a cytotoxic ethoxyhydroperoxide molecule

Lipids

Volumn 39, Issue 3, 2004, Pages 259-264

  Tagiri_Endo, Misako ^a,b   Nakagawa, Kiyotaka ^a   Sugawara, Tatsuya ^a,c   Ono, Kaori ^a   Miyazawa, Teruo ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b Industrial Technology Institute Miyagi Prefectural Government   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMILUMINESCENCE; ETHANOL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OZONIZATION; TOXICITY;

CHOLESTEROL OZONATION; CYTOXICITY; OZONOLYSIS;

CHOLESTEROL;

7 OXOCHOLESTEROL; 7ALPHA ETHOXY 3BETA HYDROXY 5ALPHA B HOMO 6 OXACHOLESTANE 5 HYDROPEROXIDE; ALCOHOL; CHOLESTEROL; CHOLESTEROL DERIVATIVE; CYTOTOXIC AGENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMOLUMINESCENCE; CHOLESTEROL METABOLISM; ELECTROSPRAY MASS SPECTROMETRY; LUNG ADENOCARCINOMA; NUCLEAR MAGNETIC RESONANCE; OZONATION; STRUCTURE ANALYSIS;

HOMO;

EID: 2942599468     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-004-1228-0     Document Type: Article

References (25)

1. Moore, G., Griffith, C., and Peters, A. (2000) Bactericidal Properties of Ozone and Its Potential Application as a Terminal Disinfectant, J. Food Prot. 63, 1100-1106.
2. Pryor, W.A., Wang, K., and Bremudez, E. (1991) The Ozonation of Unsaturated Fatty Acids: Aldehydes and Hydrogen Peroxide as Products and Possible Mediators of Ozone Toxicity, Chem. Res. Toxicol. 4, 341-348.
3. Santrock, J., Gorski, R.A., and O'Gara, J.F. (1992) Products and Mechanism of the Reaction of Ozone with Phospholipids in Unilamellar Phospholipid Vesicles, Chem. Res. Toxicol. 5, 134-141.
4. Pryor, W.A., and Wu, M. (1992) Ozonation of Methyl Oleate in Hexane, in a Thin Film, in SDS Micelles, and in Distearoylphosphatidylcholine Liposomes: Yields and Properties of the Criegee Ozonide, Chem. Res. Toxicol. 5, 505-511.
5. Squandrito, G.L., Uppu, R.M., Cueto, R., and Pryor, W.A. (1992) Production of the Criegee Ozonide During the Ozonation of 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine Liposomes, Lipids 27, 955-958.
6. Mudd, J.B., Dawson, P.J., and Santrock, J. (1997) Ozone Does Not React with Erythrocyte Membrane Lipids, Arch. Biochem. Biophys. 341, 251-266.
7. Gumulka, J., and Smith, L.L. (1983) Ozonization of Cholesterol, J. Am. Chem. Soc. 105, 1972-1979.
8. Jaworski, K., and Smith, L.L. (1988) Ozonization of Cholesterol in Nonparticipating Solvents, J. Org. Chem. 53, 545-554.
9. Pryor, W.A., Wang, K., and Bremudez, E. (1992) Cholesterol Ozonation Products as Biomarkers for Ozone Exposure in Rats, Biochem. Biophys. Res. Commun. 188, 618-623.
10. Wang, K., Bremudez, E., and Pryor, W.A. (1993) The Ozonation of Cholesterol: Separation and Identification of 2,4-Dinitrophenylhydrazine Derivatization Products of 3β-Hydroxy-5-oxo-5,6-secocholestan-6-al, Steroids 58, 225-228.
11. Jaworski, K., and Smith, L.L. (1988) Nuclear Magnetic Resonance and Infrared Spectral Characterization of Some Peroxysterols, Magn. Reson. Chem. 26, 104-107.
12. Paryzek, Z., Martynow, J., and Swoboda, W. (1990) The Reaction of Cholesterol with Ozone and Alcohols: A Revised Mechanism and Structure of the Principal Product, J. Chem. Soc., Perkin Trans. 1, 1222-1223.
13. Smith, L.L., Ezell, E.L., and Jaworski, K. (1996) On the Ozonization of Cholesterol 3-Acyl Esters in Protic Media, Steroids 61, 401-406.
14. Paryzek, Z., and Urszula, R. (1997) Ozonolysis of Cholesterol and Other 5-Steroids in the Presence of Alcohols: A Revised Mechanism and Hydroperoxide Structure of the Solvent-Participated Product, Confirmed by X-Ray Analysis, J. Chem. Soc., Perkin Trans. 2, 2313-2318.
15. Tagiri-Endo, M., Ono, K., Nakagawa, K., Yotsu-Yamashita, M., and Miyazawa, T. (2002) Ozonation of PC in Ethanol: Separation and Identification of a Novel Ethoxyhydroperoxide, Lipids 37, 1007-1012.
16. Miyazawa, T., Suzuki, T., Fujimoto, K., and Yasuda, K. (1992) Chemiluminescent Simultaneous Determination of Phosphatidylcholine Hydroperoxide and Phosphatidylethanolamine Hydroperoxide in the Liver and Brain of the Rat, J. Lipid Res. 33, 1151-1159.
17. Miyazawa, T., Fujimoto, K., Suzuki, T., and Yasuda, K. (1994) Determination of Phospholipid Hydroperoxides Using Luminol Chemiluminescence-High-Performance Liquid Chromatography, Methods Enzymol. 233, 324-332.
18. Sladowski, D., Steer, S.J., Clothier, R.H., and Balls, M. (1993) An Improved MTT Assay, J. Immunol. Methods 157, 203-207.
19. Adachi, J., Asano, M., Naito, T., Ueno, Y., and Tatsuno, Y. (1998) Chemiluminescence Detection of Cholesterol Hydroperoxide in Human Erythrocyte Membrane, Lipids 33, 1235-1240.
20. Miyazawa, T. (1989) Determination of Phospholipid Hydroperoxides in Human Blood Plasma by a Chemiluminescence-HPLC Assay, Free Radic. Biol. Med. 7, 209-217.
21. Miyazawa, T., Yamashita, T., Fujimoto, K., and Yasuda, K. (1992) Chemiluminescence Detection of 8α-Hydroperoxy-tocopherone in Photooxidized α-Tocopherol, Lipids 27, 289-294.
22. Khono, T., Sakamoto, O., Nakamura, T., and Miyazawa, T. (1993) Determination of Human Skin Surface Lipid Peroxides by Chemiluminescence-HPLC, J. Jpn. Oil Chem. Soc. 42, 204-209.
23. Miyazawa, T., Kunika, H., Fujimoto, K., Endo, Y., and Kaneda, T. (1995) Chemiluminescence Detection of Mono-, Bis-, and Tris-hydroperoxy Triacylglycerols Present in Vegetable Oils, Lipids 30, 1001-1006.
24. Naito, S. (1989) Effect of Ozone Treatment on Elongation of Hypocotyls and Microbial Counts of Bean Sprouts (in Japanese), Nippon Shokuhin Kogyo Gakkaishi 36, 181-188.
25. Naito, S. (1990) Effect of Ozone Treatment on the Rheological Properties of Wheat Flour (in Japanese), Nippon Shokuhin Kogyo Gakkaishi 37, 810-813.