Autoxidation and antioxidant activity of ubiquinol homologues in large unilamellar vesicles

Chem Phys Lipids. 1994 Jan;69(1):87-94. doi: 10.1016/0009-3084(94)90030-2.

Abstract

The antioxidant activity of ubiquinol homologues with different side-chain length such as ubiquinol-3 and ubiquinol-7 was compared with that of alpha-tocopherol when peroxidation was induced by the water-soluble initiator 2,2'-azobis-(2-amidinopropane hydrochloride). In large unilamellar vesicles containing equal amounts of alpha-tocopherol, ubiquinol-3 and ubiquinol-7 the rates of inhibition were very similar but the stoichiometric factor of quinols was approximately 1. To explain this low value, which is one-half of that found when the autoxidation was performed in apolar solvents (Chem. Phys. Lipids (1992) 61, 121-130), the oxidation of alpha-tocopherol and ubiquinol-3 initiated by the azocompound was studied both in methanol and in dimiristoyl-lecithin vesicles. The results obtained show that the ubiquinol homologues undergo a radical chain reaction taking place at the polar interface and suggest that the average preferred location of both quinol headgroups is near to the outer surface of the bilayer.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry*
  • Chemical Phenomena
  • Chemistry, Physical
  • In Vitro Techniques
  • Kinetics
  • Lipid Bilayers / chemistry*
  • Oxidation-Reduction
  • Phosphatidylcholines / chemistry
  • Ubiquinone / analogs & derivatives*
  • Ubiquinone / chemistry
  • Vitamin E / chemistry

Substances

  • Antioxidants
  • Lipid Bilayers
  • Phosphatidylcholines
  • Ubiquinone
  • Vitamin E
  • ubiquinol