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United States Department of Agriculture

Agricultural Research Service

Research Project: BIOCATALYTIC FUNCTIONALIZATION OF PLANT LIPIDS

Location: Renewable Product Technology Research Unit

Title: Feruloyl Dioleoyglycerol Antioxidant Capacity in Phospholipid Vesicles

Authors
item LASZLO, JOSEPH
item EVANS, KERVIN
item VERMILLION, KARL
item APPELL, MICHAEL

Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: April 5, 2010
Publication Date: April 15, 2010
Citation: Laszlo, J.A., Evans, K.O., Vermillion, K., Appell, M.D. 2010. Feruloyl dioleoyglycerol antioxidant capacity in phospholipid vesicles. Journal of Agricultural Food and Chemistry. 58:5842-5850.

Interpretive Summary: A new vegetable oil derivative was found to have good antioxidant properties, which demonstrates that this material may have a positive influence on maintaining the health of cellular tissues. The feruloyl dioleoylglycerol (FDOG) molecule is a prominent component of a new sun care/skin care product made from soybean oil. Prior human clinical trials indicated that subjects treated with FDOG-containing cream had improved facial skin health and appearance. In the present research, we investigated how this molecule may perform on a molecular level. We observed that this molecule works well to stop the adverse chemical events that can lead to the destruction of vital structures in living cells. FDOG readily incorporates into model cellular membranes and is able to prevent oxidative damage to these highly susceptible structures. These findings provide skin care researchers with an enhanced understanding of how molecules such as FDOG may promote improved skin health.

Technical Abstract: Ferulic acid and its esters are known to be effective antioxidants. Feruloyl dioleoylglycerol was assessed for its ability to serve as an antioxidant in model membrane phospholipid vesicles. The molecule was incorporated into single-lamellar vesicles of 1,2-dioleoyl-sn-glycero-3-phosphocholine at one and five mole fraction. Employing a lipid peroxidation inhibition assay, feruloyl dioleoylglycerol was demonstrated to express an oxidation protection ratio relative to Trolox of 0.94 and 0.74 at the 1% and 5% incorporation levels, respectively. The impact of feruloyl dioleoylglycerol incorporation on vesicle integrity was examined by determining calcein—cobalt complex leakage rates. Vesicle leakage was not influenced at 22 or 37 deg C with 5% feruloyl dioleoylglycerol incorporation in comparison to vesicles lacking feruloyl dioleoylglycerol. Resonance energy transfer analysis showed that the closest approach distance between feruloyl dioleoylglycerol and 1,2-dioleoyl-sn-glycero-3-phospho-L-serine-N-(7-nitro-2-1,3-benzoxadiazol-4-yl) was approximately 31 Å, which indicated that feruloyl dioleoylglycerol was thoroughly distributed throughout the bilayer plane. Conformational analysis determined that feruloyl dioleoylglycerol has a splayed conformation in which its feruloyl moiety is not closely contacted by its oleoyl groups. Feruloyl dioleoylglycerol integrates into the bilayer with its feruloyl moiety oriented close to the hydrophilic/lipophilic interface and its oleoyl groups extended deeply in the membrane. These findings indicate feruloyl dioleoylglycerol expresses antioxidant activity by intercepting aqueous-phase free radicals as they penetrate the bilayer.

Last Modified: 9/10/2014
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