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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Renewable Product Technology Research » Research » Publications at this Location » Publication #299101

Title: Octadecyl ferulate behavior in 1,2-dioleoylphosphocholine liposomes

item Evans, Kervin
item Compton, David - Dave
item Whitman, Nathan
item Laszlo, Joseph
item Appell, Michael
item Vermillion, Karl
item Kim, Sanghoon

Submitted to: Journal of Physical Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 8/4/2015
Publication Date: 8/11/2015
Citation: Evans, K.O., Compton, D.L., Whitman, N.A., Laszlo, J.A., Appell, M., Vermillion, K.E., Kim, S. 2015. Octadecyl ferulate behavior in 1,2-dioleoylphosphocholine liposomes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 153:333-343. doi: 10.1016/j.saa.2015.08.009.

Interpretive Summary: This research highlights the production of a natural compound that has antioxidant properties useful in cosmeceutical, nutraceutical, and pharmaceutical industries. Our goal is to develop novel, value-added lipids from commodity crops. In this research, we have combined ferulic acid (a natural plant compound) with an alcohol to form octadecyl ferulate, a natural compound found in limited quantities in plants and fungi. Our work demonstrated that octadecyl ferulate readily incorporated into model cellular membranes, stabilized these membranes and provided similar antioxidant protection as other ferulated antioxidant ingredients used in skin care. These findings provide scientists with a better understanding of how similar molecules can provide antioxidation protection.

Technical Abstract: Octadecyl ferulate, a lipophilic derivative of ferulic acid having antioxidant properties, is found throughout the plant and fungi kingdoms. Octadecyl ferulate was prepared using solid acid catalyst, monitored using supercritical fluid chromatograph and purified to a 42% yield. Differential scanning calorimetry measurements determined octadecyl ferulate to have melting/solidification phase transitions at 71 and 39 °C, respectively. 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.