Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 3/25/2010
Publication Date: 3/25/2010
Citation: Laszlo, J.A., Evans, K.O., Compton, D.L., Appell, M.D., Vermillion, K. 2010. Lipids for health and beauty: Enzymatic modification of vegetable oil [abstract]. American Chemical Society. Presentation #100. p. 58.
Technical Abstract: Ferulic acid has been extensively investigated for its potential as a cosmetic and pharmaceutical agent. We have prepared lipophilic derivatives of ferulic acid by a simple, enzyme-catalyzed transesterification reaction of ethyl ferulate with vegetable oils. Immobilized Candida antarctica lipase B, operating under solvent-free reaction conditions, showed excellent long-term stability during pilot-scale production. The reaction produces several feruloylated mono- and diacylglycerols, but the predominant species is the mono-feruloylated diacylglycerol. Feruloyl dioleoylglycerol (FDOG) was enzymatically synthesized using this process, and then isolated from the product mixture by flash chromatography and preparative HPLC. FDOG was found to have good antioxidant capacity, as determined by the DPPH radical scavenging assay. Additional studies of FDOG incorporated in phospholipid vesicles showed that this molecule does not perturb the integrity of a model membrane system and continued to display its inherent antioxidant property. Conformational analysis demonstrated that FDOG assumes a very open conformation in the bilayer with the phenolic moiety in close proximity to the polar portion of the phospholipids.