Spin-labelled lutein as a new antioxidant in protection against lipid peroxidation

Free Radic Res. 2007 Sep;41(9):1053-60. doi: 10.1080/10715760701463253.

Abstract

A new potentially antioxidant compound, spin-labelled lutein (SL-lut), was synthesized and incorporated into egg yolk phosphatidylcholine (EYPC) liposome membrane. The approximate location of nitroxide free radical groups of SL-lut was determined based on electron paramagnetic resonance (EPR) spectra. Then the ability of SL-lut to protect EYPC liposomes against lipid peroxidation (LPO) was compared to the antioxidant effects of lutein and a nitroxide spin label 3-carbamoyl-2,2,5,5-tetramethylpyrrolidin-1-yloxy (3-CP). Two free radical generation systems were used - a thermal decomposition of 2,2'-azobis (2,4 dimethyl-valeronitrile) (AMVN) and a modified Fenton reaction using ferric-8-hydroxyquinoline (Fe(HQ)(3)). Determination of the amount of thiobarbituric acid reactive species (TBARS) was used as a measure of LPO. SL-lut was the most powerful antioxidant, reducing LPO by about 6-times in AMVN-treated liposomes and 7-times in Fe(HQ)(3)-treated liposomes. Lutein alone gave only a moderate protection in both systems, while 3-CP was as efficient as SL-lut in the presence of AMVN, but not efficient whatsoever in the presence of Fe(HQ)(3). The results suggest that a nitroxide part of SL-lut plays an important role in enhancing the antioxidant activity of lutein and makes SL-lut a powerful antioxidant efficient under different conditions.

MeSH terms

  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology*
  • Azo Compounds / chemistry
  • Cyclic N-Oxides / chemistry
  • Egg Yolk / chemistry
  • Electron Spin Resonance Spectroscopy
  • Free Radicals / analysis
  • Hydroxyquinolines / chemistry
  • Lipid Peroxidation / drug effects*
  • Liposomes / chemistry
  • Lutein / chemistry
  • Lutein / pharmacology
  • Malondialdehyde / analysis
  • Membranes / chemistry
  • Membranes / drug effects
  • Nitriles / chemistry
  • Phosphatidylcholines / chemistry
  • Pyrrolidines / chemistry
  • Spin Labels
  • Thiobarbituric Acid Reactive Substances / analysis

Substances

  • Antioxidants
  • Azo Compounds
  • Cyclic N-Oxides
  • Free Radicals
  • Hydroxyquinolines
  • Liposomes
  • Nitriles
  • Phosphatidylcholines
  • Pyrrolidines
  • Spin Labels
  • Thiobarbituric Acid Reactive Substances
  • 2,2'-azobis(2,4-dimethylvaleronitrile)
  • 3-carbamoyl-2,2,5,5-tetramethyl-1-pyrrolidinyl-N-oxyl
  • Malondialdehyde
  • Lutein