Lipase-catalyzed Synthesis of Feruloylated Lysophospholipid in Toluene-Ionic Liquids and Its Antioxidant Activity

J Oleo Sci. 2021 Apr 2;70(4):531-540. doi: 10.5650/jos.ess20268. Epub 2021 Mar 10.

Abstract

In this study, Novozym 435-catalyzed interesterification of ethyl ferulate (EF) with phosphatidylcholine (PC) in a two-phase system consisting of an ionic liquid (IL) and toluene was optimized to prepare feruloylated lysophospholipids (FLPs). Optimum conditions for the interesterification process were found to be [Bmim][Tf2N]/toluene ratio of 1:1 (v/v), solvent volume of 4 mL, molecular sieves (4 Å) concentration of 80 mg/mL, reaction temperature of 55°C, substrate molar ratio of 5:1 (PC/EF), Novozym 435 concentration of 50 mg/mL. Under these conditions, two FLPs products (1-FLP and 2-FLP) with total conversion rate of 50.79% were obtained. Because the formation of 1-FLP was significantly higher than 2-FLP, 1-FLP was purified and characterized by LC-MS and NMR. In addition, 1-FLP showed DPPH scavenging activity comparable with those of EF and BHT. Therefore, this study provides a good method for transformation of ferulic acid to improve its solubility and promote its application as functional ingredient in the food and pharmaceutical industries.

Keywords: antioxidant activity; ferulic acid; ionic liquid; lipase; phospholipids.

MeSH terms

  • Antioxidants*
  • Caffeic Acids / chemistry*
  • Catalysis
  • Drug Industry
  • Enzymes, Immobilized
  • Esterification
  • Food Industry
  • Fungal Proteins
  • Ionic Liquids / chemistry*
  • Lipase / chemistry*
  • Lysophospholipids / chemical synthesis*
  • Lysophospholipids / chemistry
  • Lysophospholipids / pharmacology
  • Phosphatidylcholines / chemistry*
  • Solubility
  • Solvents / chemistry
  • Temperature
  • Toluene / chemistry*

Substances

  • Antioxidants
  • Caffeic Acids
  • Enzymes, Immobilized
  • Fungal Proteins
  • Ionic Liquids
  • Lysophospholipids
  • Phosphatidylcholines
  • Solvents
  • Toluene
  • ethyl ferulate
  • Novozyme 435
  • Lipase