Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Ozonation of cholesterol in the presence of ethanol: identification of a cytotoxic ethoxyhydroperoxide molecule.

Literature DB >> 15233405

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

Misako Tagiri-Endo¹, Kiyotaka Nakagawa, Tatsuya Sugawara, Kaori Ono, Teruo Miyazawa.

Abstract

Cholesterol ozonation was carried out in ethanol-containing aqueous or nonaqueous solvent, and the ozonized products were analyzed by chemiluminescence detection-HPLC with on-line electrospray MS (HPLC-CL-MS) and characterized on the basis of NMR and FABMS. After the ozonolysis of cholesterol in water/ethanol (aqueous system) as well as in chloroform/ethanol (nonaqueous system), a unique ethoxyhydroperoxide molecule (7alpha-ethoxy-3beta-hydroxy-5alpha-B-homo-6-oxacholestane-5-hydroperoxide, termed "7alpha-ethoxy-5-OOH") appeared as main ozonation product. In addition to structural analysis, we confirmed the remarkable cytotoxicity of 7alpha-ethoxy-5-OOH toward human lung adenocarcinoma A549 cells and found that its cytotoxicity is superior to that of the commonly known autoxidized cholesterol (3beta-hydroxycholest-5-ene-7-one). Hence, 7alpha-ethoxy-5-OOH is a toxic molecule of primary importance, arising during cholesterol ozonation in the presence of ethanol.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2004 PMID： 15233405 DOI： 10.1007/s11745-004-1228-0

Source DB: PubMed Journal: Lipids ISSN： 0024-4201 Impact factor: 1.880

17 in total

1. On the ozonization of cholesterol 3-acyl esters in protic media.

Authors: L L Smith; E L Ezell; K Jaworski
Journal: Steroids Date: 1996-07 Impact factor: 2.668

2. Chemiluminescent determination of cholesterol hydroperoxides in human erythrocyte membrane.

Authors: J Adachi; M Asano; T Naito; Y Ueno; Y Tatsuno
Journal: Lipids Date: 1998-12 Impact factor: 1.880

3. An improved MTT assay.

Authors: D Sladowski; S J Steer; R H Clothier; M Balls
Journal: J Immunol Methods Date: 1993-01-04 Impact factor: 2.303

4. Ozone does not react with human erythrocyte membrane lipids.

Authors: J B Mudd; P J Dawson; J Santrock
Journal: Arch Biochem Biophys Date: 1997-05-15 Impact factor: 4.013

5. The ozonation of cholesterol: separation and identification of 2,4-dinitrophenylhydrazine derivatization products of 3 beta-hydroxy-5-oxo-5,6-secocholestan-6-al.

Authors: K Wang; E Bermúdez; W A Pryor
Journal: Steroids Date: 1993-05 Impact factor: 2.668

6. Chemiluminescent simultaneous determination of phosphatidylcholine hydroperoxide and phosphatidylethanolamine hydroperoxide in the liver and brain of the rat.

Authors: T Miyazawa; T Suzuki; K Fujimoto; K Yasuda
Journal: J Lipid Res Date: 1992-07 Impact factor: 5.922

7. The ozonation of unsaturated fatty acids: aldehydes and hydrogen peroxide as products and possible mediators of ozone toxicity.

Authors: W A Pryor; B Das; D F Church
Journal: Chem Res Toxicol Date: 1991 May-Jun Impact factor: 3.739

1. Studying interfacial reactions of cholesterol sulfate in an unsaturated phosphatidylglycerol layer with ozone using field induced droplet ionization mass spectrometry.

Authors: Jae Yoon Ko; Sun Mi Choi; Young Min Rhee; J L Beauchamp; Hugh I Kim
Journal: J Am Soc Mass Spectrom Date: 2011-11-09 Impact factor: 3.109

2. Lipid hydroperoxides in nutrition, health, and diseases.

Authors: Teruo Miyazawa
Journal: Proc Jpn Acad Ser B Phys Biol Sci Date: 2021 Impact factor: 3.493

2 in total