Improving the stability and antioxidant properties of sesame oil: water-soluble spray-dried emulsions from new transesterified phenolic derivatives.
Hydrosoluble sesame oil fatty acid transesters having enhanced antioxidant activities were synthesized in a two-step process. The key step involved the biocatalyzed (lipase from Candida antarctica) acylation of sesame oil methanolic ester with either vanillyl (VNA) or piperonyl benzylic alcohols, or 5-hydroxymethyl resorcinol (5-HMR). These substrates were selected to introduce phenolic or sesamol structurally related frameworks. The VNA and 5-HMR-derived transesters were obtained with 20-40% yields and retained the starting proportions of sesame oil linoleic, oleic, and saturated acids, these fatty acids also being the only constituents of the nonesterified fraction. The VNA-derived transester showed the best antioxidant capacity in standard assays and was processed as the unique lipid phase of spray-dried emulsions containing a high level of linoleic acid phenolic ester. These emulsions provided a high degree of protection to UV-irradiated fibroblasts, through the potential synergy between VNA antioxidant action and replenishment of damaged membranes by unsaturated fatty acids.
Alencar
Juliana
J
Sondes Moléculaires en Biologie, Laboratoire Chimie Provence, UMR 6264 CNRS-Universités d'Aix-Marseille, av. Escadrille Normandie-Niemen, Marseille Cedex 20, France.
Gosset
Gaëlle
G
Robin
Maxime
M
Pique
Valérie
V
Culcasi
Marcel
M
Clément
Jean-Louis
JL
Mercier
Anne
A
Pietri
Sylvia
S
D000818:Animals; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology; D004655:Emulsions / Q000737:chemistry; D004951:Esterification; D005347:Fibroblasts / Q000187:drug effects / Q000528:radiation effects; D051379:Mice; D041681:NIH 3T3 Cells; D010636:Phenols / Q000737:chemistry* / Q000494:pharmacology; D012715:Sesame Oil / Q000737:chemistry* / Q000494:pharmacology
D000975:Antioxidants; D004655:Emulsions; D010636:Phenols; D012715:Sesame Oil