Synthesis of structured lipids and etherlipids with antioxidants: combination of a selena fatty acid and a selena fatty alcohol with a carotenoic acid in glyceride molecules.
Selenium and carotenoids show similar and complementary properties and protect against a variety of pathological processes. Mixtures of both compounds are found in nutritional supplements and are used to prevent several diseases. The synthetic connection of carotenoids with selenium in glycerols may increase the chemopreventive activity of the individual compounds. Beta-apo-8'-carotenoic acid and 7-selenacapryloic acid were esterified with glycerol to highly unsaturated stable di- and triglycerides. Intramolecular selenium:carotenoid ratios of 1:1, 2:1 and 1:2 were obtained for 1-(7-selenaoctanoyl)-3-(3beta-apo-8 -carotenoyl)-glycerol, 1,3-di-(beta-apo-8'-carotenoyl)-2-(7-selenaoctanoyl)-glycero l and 1,2-di-(7-selenaoctanoyl)-3-(beta-apo-8'-carotenoyl)-glycero l, respectively. The carotenoic acid was likewise connected to the pharmacologically interesting 11-selenalaurylglycerolether forming an alkyl-acylglyceride: 1-(11-selenadodecyl)-3-(beta-apo-8'-carotenoyl)-glycerol.
Houte
H
H
Department of Chemistry, Norwegian University of Science and Technology, Trondheim.
Partali
V
V
Sliwka
H R
HR
Quartey
E G
EG
D000975:Antioxidants / Q000138:chemical synthesis*; D002338:Carotenoids / Q000138:chemical synthesis; D005989:Glycerides / Q000138:chemical synthesis*; D005995:Glyceryl Ethers / Q000138:chemical synthesis*; D008055:Lipids / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018036:Selenium Compounds / Q000138:chemical synthesis*
D000975:Antioxidants; D005989:Glycerides; D005995:Glyceryl Ethers; D008055:Lipids; D018036:Selenium Compounds; D002338:Carotenoids