Evidence for the presence of 7-hydroperoxycholest-5-en-3β-ol in oxidized human LDL

Bruno Malavasi, Maria Francesca Rasetti, Paola Roma, Roberta Fogliatto, Pietro Allevi, Alberico Luigi Catapano, Giovanni Galli

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

Low density lipoprotein (LDL) cholesterol is known to be oxidized both in vitro and in vivo giving rise to oxygenated sterols. Conflicting results, however, have been reported concerning both the nature and the relative concentrations of these compounds in oxidized human LDL. We examined the extracts obtained from Cu2+-oxidized LDL. Thin layer chromatography analysis showed that the sterol mixture became more complex with reaction time. Analysis of the components by thin layer chromatography and mass spectrometry allowed to establish that 7α- and 7β-hydroperoxycholest-5-en-3β-ol (7αOOH and βOOH) are largely prevalent among the oxysterols at early times of oxidation. These hydroperoxy derivatives have not been previously identified in oxidized LDL. The concentration of 7-hydroperoxycholest-5-en-3β-ol decreased with oxidation time with a concomitant increase of cholest-5-en-3β,7α-diol (7αOH), cholest-5-en-3β,7β-diol (7βOH), cholesta-3,5-dien-7-one (CD) and cholest-5-en-3β-ol-7-one (7CO). After 24 h of oxidation a minor component of the LDL sterols was cholestan-3β-ol-5,6-oxide (EP).

Original languageEnglish
Pages (from-to)209-214
Number of pages6
JournalChemistry and Physics of Lipids
Volume62
Issue number3
DOIs
Publication statusPublished - 1992

Fingerprint

Sterols
LDL Lipoproteins
Thin layer chromatography
Thin Layer Chromatography
Oxidation
Cholestanol
LDL Cholesterol
Oxides
Mass spectrometry
Mass Spectrometry
Derivatives
oxidized low density lipoprotein

Keywords

  • cholesterol hydroperoxides
  • cholesterol oxidation
  • oxidized LDL
  • oxysterols

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics

Cite this

Evidence for the presence of 7-hydroperoxycholest-5-en-3β-ol in oxidized human LDL. / Malavasi, Bruno; Rasetti, Maria Francesca; Roma, Paola; Fogliatto, Roberta; Allevi, Pietro; Catapano, Alberico Luigi; Galli, Giovanni.

In: Chemistry and Physics of Lipids, Vol. 62, No. 3, 1992, p. 209-214.

Research output: Contribution to journalArticle

Malavasi, Bruno ; Rasetti, Maria Francesca ; Roma, Paola ; Fogliatto, Roberta ; Allevi, Pietro ; Catapano, Alberico Luigi ; Galli, Giovanni. / Evidence for the presence of 7-hydroperoxycholest-5-en-3β-ol in oxidized human LDL. In: Chemistry and Physics of Lipids. 1992 ; Vol. 62, No. 3. pp. 209-214.
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AB - Low density lipoprotein (LDL) cholesterol is known to be oxidized both in vitro and in vivo giving rise to oxygenated sterols. Conflicting results, however, have been reported concerning both the nature and the relative concentrations of these compounds in oxidized human LDL. We examined the extracts obtained from Cu2+-oxidized LDL. Thin layer chromatography analysis showed that the sterol mixture became more complex with reaction time. Analysis of the components by thin layer chromatography and mass spectrometry allowed to establish that 7α- and 7β-hydroperoxycholest-5-en-3β-ol (7αOOH and βOOH) are largely prevalent among the oxysterols at early times of oxidation. These hydroperoxy derivatives have not been previously identified in oxidized LDL. The concentration of 7-hydroperoxycholest-5-en-3β-ol decreased with oxidation time with a concomitant increase of cholest-5-en-3β,7α-diol (7αOH), cholest-5-en-3β,7β-diol (7βOH), cholesta-3,5-dien-7-one (CD) and cholest-5-en-3β-ol-7-one (7CO). After 24 h of oxidation a minor component of the LDL sterols was cholestan-3β-ol-5,6-oxide (EP).

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