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

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-(β-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.