Synthesis of Functional Feruloylated Lipids through Enzymatic Irreversible Transesterification Protocols

Functional feruloylated lipids, which are composed of 1(3)-feruloyl-monooleyl-glycerol (FMOG) and 1(3)-feruloyl-dioleyl-glycerol (FDOG), was prepared through the lipase-catalyzed irreversible transesterification between vinyl feruate (VF) and triolein (TO) in toluene. The nuclear magnetic resonance (NMR) and electrospray ionization-mass spectroscopy (ESI-MS) analysis confirmed the structure of VF. The influences of molar ratio of substrates, reaction time, reaction temperature, water activity and enzyme amount on the total conversion of reaction and conversion yield of FMOG and FDOG were analyzed systematically. The optimal conditions are as follows: VF:EF=1:3, 62h, 55°C, a_w 0.07, 20mg/mL Novozym 435. Under the optimal conditions, the average highest conversion of feruloylated lipids achieved was 92.29±2.13%, which was composed of FMOG 39.78±4.85% and FDOG 52.51±6.01%, respectively. It could provide an efficient approach for preparing feruloylated lipids.