ethyl-ferulate and 1-1-diphenyl-2-picrylhydrazyl

Steryl ferulates (SFs) are a subclass of bioactive lipids contributing to the health-promoting effects of whole grains. Most related studies focus on γ-oryzanol, a SF mixture from rice, since individual steryl ferulates are not commercially available. There is little evidence that individual SFs may vary in their bioactivity. The aim of this study was to evaluate the antioxidant activity of eight individual SFs by determining their radical scavenging capacity. Additional molecular properties of the individual SFs were determined by molecular simulation in order to identify correlations with their antioxidant activities. Our study demonstrates that individual SFs exhibit 1,1-diphenyl-2-picrylhydrazyl radical, hydroxyl radical, and superoxide anion radical scavenging abilities with subtle differences that were highly dependent on the kind of reaction taking place. The grouping of SFs by principle component analysis was mainly attributed to molecular properties, not antioxidant activities. Solvation energy was significantly correlated with some experimental observations. To our knowledge, this is the first study to evaluate the antioxidant activity of eight individual steryl ferulates from different sources. Results of this work will provide better insight into the antioxidant activity of SFs and the health benefits of whole grains.

Topics: Algorithms; Antioxidants; Biphenyl Compounds; Coumaric Acids; Dietary Fiber; Edible Grain; Electron Spin Resonance Spectroscopy; Molecular Structure; Oryza; Oxidation-Reduction; Phenylpropionates; Phytosterols; Picrates; Plant Extracts

1,3-Diferuloyl-sn-glycerol is found ubiquitously throughout the plant kingdom, possessing ultraviolet adsorbing and antioxidant properties. Diferuloyl glycerol was synthesized and isolated as a byproduct in up to 5% yield from a pilot plant scale packed-bed, biocatalytic transesterification of ethyl ferulate with soybean oil or mono- and diacylglycerols from soybean oil. The yield of the diferuloyl glycerol byproduct was directly proportional to the overall water concentration of the bioreactor. The isolated diferuloyl glycerol exhibited good ultraviolet adsorbing properties, 280-360 nm with a lambda(max) 322 nm, and compared well to the efficacy of commercial sunscreen active ingredients. The antioxidant capacity of diferuloyl glycerol (0.25-2.5 mM) was determined by its ability to scavenge 2,2-diphenyl-1-picrylhydrazyl radicals and was comparable to that of ferulic acid. At current pilot plant scale production capacity, 120 kg diferuloyl glycerol byproduct could be isolated per year.

Topics: Antioxidants; Bioreactors; Biphenyl Compounds; Caffeic Acids; Coumaric Acids; Glycerol; Glycine max; Picrates; Soybean Oil; Spectrum Analysis; Sunscreening Agents; Ultraviolet Rays