Ozonation of PC in ethanol: separation and identification of a novel ethoxyhydroperoxide.
The product of the ozonolysis of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine in ethanol-containing solvent was analyzed by chemiluminescence detection-HPLC with on-line electrospray MS, and characterized on the basis of NMR spectroscopy and MS in high-resolution fast atom bombardment mode. The reaction yielded a large amount of a novel ethoxyhydroperoxide compound [1-palmitoyl-2-(9-ethoxy-9-hydroperoxynonanoyl)-sn-glycero-3-phosphcholinel. In addition to a structural analysis, we speculate on the reaction pathway and discuss the possibility of ethoxyhydroperoxide as a potentially reactive ozonized lipid in food and biological materials.
Tagiri-Endo
Misako
M
Food & Biodynamic Chemistry Laboratory, Graduate School of Life Science and Agriculture, Tohoku University, Sendai, Japan.
Ono
Kaori
K
Nakagawa
Kiyotaka
K
Yotsu-Yamashita
Mari
M
Miyazawa
Teruo
T
D002851:Chromatography, High Pressure Liquid; D000431:Ethanol / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D010126:Ozone / Q000737:chemistry*; D010713:Phosphatidylcholines / Q000737:chemistry*
D010713:Phosphatidylcholines; D000431:Ethanol; D010126:Ozone; D006861:Hydrogen Peroxide