Synthesis of a triantioxidant compound: combination of beta-apo-8'-carotenoic acid, selenacapryloic acid and trolox in a triglyceride

Chem Phys Lipids. 2001 Jul;112(1):59-65. doi: 10.1016/s0009-3084(01)00164-5.

Abstract

Carotenoids, vitamin-E and selenium show similar or complementary physiological properties and protect against a variety of pathological processes. Mixtures of these antioxidants are found in nutritional supplements and are used to prevent several diseases. The synthetic connection of carotenoids, vitamin-E and selenium may increase the chemopreventive activity of the individual compounds. A carotenoic acid, a selena fatty acid and the vitamin-E derivative trolox were successively esterified with glycerol to 1-(beta-apo-8'carotenoyl)-2-(7-selenaoctanoyl)-3-(6-hydroxy-2,5,7,8-tetramethylchroman-2-acyl)-glycerol. This triantioxidant compound revealed, in the DPPH (1,1-diphenyl-2-picrylhydrazyl) test, an additive affect, consisting of the radical quenching activity of the carotenoid and trolox. The DPPH test was not sensitive for the Se moiety in the triantioxidant compound.

MeSH terms

  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry*
  • Caprylates / chemistry*
  • Carotenoids / chemistry*
  • Chromans / chemistry*
  • Drug Design
  • Indicators and Reagents
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism
  • Triglycerides / chemical synthesis*
  • Triglycerides / chemistry

Substances

  • Antioxidants
  • Caprylates
  • Chromans
  • Indicators and Reagents
  • Triglycerides
  • apo-8'-carotenoic acid
  • Carotenoids
  • octanoic acid
  • 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid