title: Radical scavenging activity of lipophilized products from transesterification of flaxseed oil with cinnamic acid or ferulic acid.
abstract: Lipase-catalyzed transesterification of flaxseed oil with cinnamic acid (CA) or ferulic acid (FA) using an immobilized lipase from Candida antarctica (E.C. 3.1.1.3) was conducted to evaluate whether the lipophilized products provided enhanced antioxidant activity in the oil. Lipase-catalyzed transesterification of flaxseed oil with CA or FA produced a variety of lipophilized products (identified using ESI-MS-MS) such as monocinnamoyl/feruloyl-diacylglycerol, dicinnamoyl-monoacylglycerol and monocinnamoyl-monoacylglycerol. The free radical scavenging activity of the lipophilized products of lipase-catalyzed transesterification of flaxseed oil with CA or FA toward 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.) were both examined in ethanol and ethyl acetate. The polarity of the solvents proved important in determining the radical scavenging activity of the substrates. Unesterified FA showed the highest free radical scavenging activity among all substrates tested while CA had negligible activity. The esterification of CA or FA with flaxseed oil resulted in significant increase and decrease in the radical scavenging activity compared with the native phenolic acid, respectively. Based on the ratio of a substrate to DPPH. concentration, lipophilized FA was a much more efficient free radical scavenger compared to lipophilized CA and was able to provide enhanced antioxidant activity in the flaxseed oil. Lipophilized cinnamic acid did not provide enhanced radical scavenging activity in the flaxseed oil as the presence of natural hydrophilic antioxidants in the oil had much greater radical scavenging activity.
authors.affiliation: School of Science, Monash University Sunway Campus, Jalan Lagoon Selatan, 46150 Bandar Sunway, Selangor, Malaysia.
authors.forename: Wee-Sim
authors.initials: WS
authors.lastname: Choo
authors.forename: Edward John
authors.initials: EJ
authors.lastname: Birch
authors.forename: Ian
authors.initials: I
authors.lastname: Stewart
mesh_terms: D001713:Biphenyl Compounds / Q000378:metabolism; D002175:Candida / Q000201:enzymology; D002851:Chromatography, High Pressure Liquid; D002934:Cinnamates / Q000378:metabolism / Q000494:pharmacology*; D003373:Coumaric Acids / Q000378:metabolism / Q000494:pharmacology*; D004800:Enzymes, Immobilized / Q000378:metabolism; D004951:Esterification; D016166:Free Radical Scavengers / Q000494:pharmacology*; D008043:Linseed Oil / Q000378:metabolism* / Q000494:pharmacology*; D008049:Lipase / Q000378:metabolism*; D010851:Picrates / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D001713:Biphenyl Compounds; D002934:Cinnamates; D003373:Coumaric Acids; D004800:Enzymes, Immobilized; D016166:Free Radical Scavengers; D010851:Picrates; C029010:cinnamic acid; D008043:Linseed Oil; C004999:ferulic acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D008049:Lipase