2004年3月
Ozonation of cholesterol in the presence of ethanol: Identification of a cytotoxic ethoxyhydroperoxide molecule
LIPIDS
- ,
- ,
- ,
- ,
- 巻
- 39
- 号
- 3
- 開始ページ
- 259
- 終了ページ
- 264
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1007/s11745-004-1228-0
- 出版者・発行元
- AMER OIL CHEMISTS SOC A O C S PRESS
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-13homo-6-oxacholestane-5-hydroperoxide, termed "7alpha-ethoxy-5OOH") 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.
- リンク情報
-
- DOI
- https://doi.org/10.1007/s11745-004-1228-0
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000221990700009&DestApp=WOS_CPL
- URL
- http://www.scopus.com/inward/record.url?eid=2-s2.0-2942599468&partnerID=MN8TOARS
- URL
- http://orcid.org/0000-0002-1203-5521
- ID情報
-
- DOI : 10.1007/s11745-004-1228-0
- ISSN : 0024-4201
- ORCIDのPut Code : 39432122
- SCOPUS ID : 2942599468
- Web of Science ID : WOS:000221990700009