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

Misako Tagiri_Endo, Kiyotaka Nakagawa, Tatsuya Sugawara, Kaori Ono, Teruo Miyazawa

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

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 (7α -ethoxy-3β-hydroxy-5α-B-homo-6-oxacholestane-5-hydroperoxide, termed "7α-ethoxy-5-OOH") appeared as main ozonation product. In addition to structural analysis, we confirmed the remarkable cytotoxicity of 7α-ethoxy-5-OOH toward human lung adenocarcinoma A549 cells and found that its cytotoxicity is superior to that of the commonly known autoxidized cholesterol (3β-hydroxycholest-5-ene-7-one). Hence, 7α-ethoxy-5-OOH is a toxic molecule of primary importance, arising during cholesterol ozonation in the presence of ethanol.

Original languageEnglish
Pages (from-to)259-264
Number of pages6
JournalLipids
Volume39
Issue number3
DOIs
Publication statusPublished - 2004 Jan 1

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Cell Biology

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