Literature DB >> 12530561

Ozonation of PC in ethanol: separation and identification of a novel ethoxyhydroperoxide.

Misako Tagiri-Endo1, Kaori Ono, Kiyotaka Nakagawa, Mari Yotsu-Yamashita, Teruo Miyazawa.   

Abstract

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.

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Year:  2002        PMID： 12530561     DOI： 10.1007/s11745-006-0993-0

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


  20 in total

1.  A new sensitive assay for the measurement of hydroperoxides.

Authors:  R L Heath; A L Tappel
Journal:  Anal Biochem       Date:  1976-11       Impact factor: 3.365

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.  O3-induced change in bronchial reactivity to methacholine and airway inflammation in humans.

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Journal:  J Appl Physiol (1985)       Date:  1986-04

4.  An enzymatic protective mechanism against lipid peroxidation damage to lungs of ozone-exposed rats.

Authors:  C K Chow; A L Tappel
Journal:  Lipids       Date:  1972-08       Impact factor: 1.880

5.  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

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.  Chemiluminescence detection of 8a-hydroperoxy-tocopherone in photooxidized alpha-tocopherol.

Authors:  T Miyazawa; T Yamashita; K Fujimoto
Journal:  Lipids       Date:  1992-04       Impact factor: 1.880

8.  Chemiluminescence detection of mono-, bis-, and tris-hydroperoxy triacylglycerols present in vegetable oils.

Authors:  T Miyazawa; H Kunika; K Fujimoto; Y Endo; T Kaneda
Journal:  Lipids       Date:  1995-11       Impact factor: 1.880

9.  Direct mass spectrometric analysis of ozonides: application to unsaturated glycerophosphocholine lipids.

Authors:  K A Harrison; R C Murphy
Journal:  Anal Chem       Date:  1996-09-15       Impact factor: 6.986

10.  Ozone exposure increases respiratory epithelial permeability in humans.

Authors:  H R Kehrl; L M Vincent; R J Kowalsky; D H Horstman; J J O'Neil; W H McCartney; P A Bromberg
Journal:  Am Rev Respir Dis       Date:  1987-05
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  3 in total

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

Authors:  Misako Tagiri-Endo; Kiyotaka Nakagawa; Tatsuya Sugawara; Kaori Ono; Teruo Miyazawa
Journal:  Lipids       Date:  2004-03       Impact factor: 1.880

Review 3.  Analytical and Structural Tools of Lipid Hydroperoxides: Present State and Future Perspectives.

Authors:  Vassiliki G Kontogianni; Ioannis P Gerothanassis
Journal:  Molecules       Date:  2022-03-25       Impact factor: 4.411
  3 in total

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