p-Hydroxyphenylacetaldehyde, the major product of tyrosine oxidation by the activated myeloperoxidase system can act as an antioxidant in LDL

FEBS Lett. 2001 Feb 9;490(1-2):28-31. doi: 10.1016/s0014-5793(01)02131-7.

Abstract

The oxidative modification of low density lipoprotein (LDL) may play a significant role in atherogenesis. HOCl generated by the myeloperoxidase/H2O2/Cl- system of activated neutrophils may be operative in vivo making LDL atherogenic. Tyrosine has been found to be oxidized by HOCl to p-hydroxyphenylacetaldehyde (p-HA) capable of modifying phospholipid amino groups in LDL. As an amphiphatic phenolic compound, p-HA may have the potential to act as an antioxidant in the lipid phase of LDL. The present results show that (a) tyrosine exerts a protective effect on LDL modification by HOCl, (b) p-HA could act as antioxidant associated with the lipoprotein preventing cell- and transition metal ion-mediated LDL oxidation and (c) p-HA was able to scavenge free radicals.

MeSH terms

  • Acetaldehyde / analogs & derivatives*
  • Acetaldehyde / pharmacology*
  • Antioxidants / pharmacology*
  • Dose-Response Relationship, Drug
  • Electrophoresis, Agar Gel
  • Endothelium, Vascular / cytology
  • Free Radical Scavengers / metabolism
  • Humans
  • Hydrogen-Ion Concentration
  • Hypochlorous Acid / metabolism
  • Ions
  • Lipid Metabolism
  • Lipoproteins, LDL / metabolism*
  • Neutrophils / metabolism
  • Oxygen / metabolism*
  • Peroxidase / metabolism*
  • Phenol
  • Protein Binding
  • Thiobarbituric Acid Reactive Substances / metabolism
  • Time Factors
  • Tyrosine / metabolism*
  • Umbilical Veins / cytology

Substances

  • Antioxidants
  • Free Radical Scavengers
  • Ions
  • Lipoproteins, LDL
  • Thiobarbituric Acid Reactive Substances
  • Phenol
  • Tyrosine
  • Hypochlorous Acid
  • 4-hydroxyphenylacetaldehyde
  • Peroxidase
  • Acetaldehyde
  • Oxygen