Chemoenzymatic synthesis of feruloylated monoacyl- and diacyl-glycerols in ionic liquids

Biotechnol Lett. 2009 Dec;31(12):1885-9. doi: 10.1007/s10529-009-0086-2. Epub 2009 Jul 25.

Abstract

Feruloylated monoacyl- and diacyl-glycerols (FMAGs and FDAGs) are lipophilic antioxidants and potential UV absorbers. FMAGs and FDAGs were synthesized by a novel chemoenzymatic method: firstly, ferulic acid was esterified with glycerol to synthesize glyceryl ferulate, using p-toluenesulfonic acid as chemical catalyst in 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF(4)); secondly, glyceryl ferulate was esterified with oleic acid to synthesize FMAGs and FDAGs, using Novozym 435 as biocatalyst in 1-butyl-3-methylimidazolium hexafluorophosphate ([Bmim]PF(6)). The conversion of ferulic acid and yield of glyceryl ferulate in the first reaction were both 98%. The yields of FMAGs and FDAGs in the second reaction reached 34 +/- 2% and 66 +/- 3%, respectively.

MeSH terms

  • Antioxidants / metabolism*
  • Benzenesulfonates / metabolism
  • Coumaric Acids / metabolism
  • Enzymes, Immobilized
  • Fungal Proteins
  • Imidazoles / metabolism
  • Ionic Liquids / metabolism*
  • Lipase / metabolism
  • Monoglycerides / metabolism*
  • Oleic Acid / metabolism
  • Radiation-Protective Agents / metabolism*

Substances

  • 1-butyl-3-methylimidazolium hexafluorophosphate
  • 1-butyl-3-methylimidazolium tetrafluoroborate
  • Antioxidants
  • Benzenesulfonates
  • Coumaric Acids
  • Enzymes, Immobilized
  • Fungal Proteins
  • Imidazoles
  • Ionic Liquids
  • Monoglycerides
  • Radiation-Protective Agents
  • glyceryl ferulate
  • Oleic Acid
  • ferulic acid
  • Novozyme 435
  • Lipase
  • 4-toluenesulfonic acid