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Title:   Author  item
                                            Laszlo, Josephitem
                                            Evans, Kervinitem
                                            Compton, David

                                                         - *Dave*item
                                            Appell, Michaelitem
                                            Vermillion, Karl
  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.Interpretive Summary:
                                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.


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