Octadecyl ferulate behavior in 1,2-Dioleoylphosphocholine liposomes.
Octadecyl ferulate was prepared using solid acid catalyst, monitored using Supercritical Fluid Chromatography and purified to a 42% yield. Differential scanning calorimetry measurements determined octadecyl ferulate to have melting/solidification phase transitions at 67 and 39°C, respectively. AFM imaging shows that 5-mol% present in a lipid bilayer induced domains to form. Phase behavior measurements confirmed that octadecyl ferulate increased transition temperature of phospholipids. Fluorescence measurements demonstrated that octadecyl ferulate stabilized liposomes against leakage, maintained antioxidant capacity within liposomes, and oriented such that the feruloyl moiety remained in the hydrophilic region of the bilayer. Molecular modeling calculation indicated that antioxidant activity was mostly influenced by interactions within the bilayer.
Renewable Products Technology Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA. Electronic address: Kervin.Evans@ars.usda.gov.
Kervin O
KO
Evans
Renewable Products Technology Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA.
David L
DL
Compton
Renewable Products Technology Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA.
Nathan A
NA
Whitman
Renewable Products Technology Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA.
Joseph A
JA
Laszlo
Bacterial Foodborne Pathogens and Mycology, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA.
Michael
M
Appell
Functional Foods Research, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA.
Karl E
KE
Vermillion
Plant Polymer Research, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA.
Sanghoon
S
Kim
D000975:Antioxidants / Q000032:analysis; D002152:Calorimetry, Differential Scanning; D003373:Coumaric Acids / Q000737:chemistry*; D008051:Lipid Bilayers / Q000737:chemistry; D015227:Lipid Peroxidation; D008081:Liposomes / Q000737:chemistry*; D018625:Microscopy, Atomic Force; D008958:Models, Molecular; D008968:Molecular Conformation; D010713:Phosphatidylcholines / Q000737:chemistry*; D013696:Temperature; D013997:Time Factors
D000975:Antioxidants; D003373:Coumaric Acids; D008051:Lipid Bilayers; D008081:Liposomes; D010713:Phosphatidylcholines; C549361:octyl ferulate; C017251:1,2-oleoylphosphatidylcholine
Antioxidation; Fluorescence; Liposomes; Octadecyl ferulate; Partition coefficient