Novel Conjugates of 1,3-Diacylglycerol and Lipoic Acid : Synthesis, DPPH Assay, and RP-LC-MS-APCI Analysis

Abstract EN

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 (EC50 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.