title: Novel Conjugates of 1,3-Diacylglycerol and Lipoic Acid: Synthesis, DPPH Assay, and RP-LC-MS-APCI Analysis.
abstract: 1,3-Diacylglycerol is known to reduce body weight and fat deposits in humans. α-Lipoic acid is a potent antioxidant and effective against many pathological conditions, including obesity and related metabolic syndromes. The present work is based on the hypothesis that the hybrid molecules of 1,3-diacylglycerol and lipoic acid possess synergistic and/or additive effects compared with the parent compounds against obesity, overweight, and related metabolic syndromes. Laboratory scale synthesis of 1,3-dioleoyl-2-lipoyl-sn-glycerol (yield 80%) and 1,3-dioleoyl-2-dihydrolipoyl-sn-glycerol (yield 70%) was performed for the first time and supported by NMR and MS data. Free radical scavenging capacity of the conjugates was assayed using DPPH test. A remarkably high in vitro free radical scavenging capacity was demonstrated for the 1,3-dioleoyl-2-dihydrolipoyl-sn-glycerol (EC(50) value 0.21). RP-HPLC-MS-APCI analysis showed satisfactory separation between the conjugates (R~1). Protonated molecular ion of the conjugates at m/z 809 and m/z at 811, respectively, and their characteristic fragment ions were abundant.
authors.affiliation: Department of Food Science, Uppsala BioCenter, Swedish University of Agricultural Sciences (SLU), P.O. Box 7051, 750 07 Uppsala, Sweden.
authors.forename: Samanthi R P
authors.initials: SR
authors.lastname: Madawala
authors.forename: Rolf E
authors.initials: RE
authors.lastname: Andersson
authors.forename: Jelena A
authors.initials: JA
authors.lastname: Jastrebova
authors.forename: Maria
authors.initials: M
authors.lastname: Almeida
authors.forename: Paresh C
authors.initials: PC
authors.lastname: Dutta