campesteryl-ferulate and ferulic-acid

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

Steryl ferulates (SFs) belong to the bioactive lipids contributing to the health promoting effects of whole grains. However, their intestinal absorption remains unclear. We investigated the permeation of individual SFs using an in vitro intestinal barrier model.. An in vitro Caco-2 cell monolayer, mimicking the intestinal barrier, was used to evaluate the permeation of eight SFs from different sources. A method based on ultra-performance LC with high-resolution mass spectrometric detection was developed for their quantification. Although only a negligible amount (< 0.5%) permeated across the Caco-2 cell monolayer, some differences in the permeability coefficients were observed between individual SFs. Permeation mechanism was mainly passive diffusion.. This work indicates that the permeation of SFs across the gut is very low. Therefore, cholesterol lowering and antioxidant activity-related health benefits of SFs most likely occur in the gut independently from absorption.

Topics: Caco-2 Cells; Cell Survival; Coumaric Acids; Dietary Fiber; Esters; Humans; Intestinal Absorption; Intestines; Mass Spectrometry; Models, Biological; Permeability; Phytosterols; Whole Grains

Campesteryl ferulate (3a, 24R/α) and epi-campesteryl ferulate (3b, 24S/β), components of rice bran γ-oryzanol, were isolated by the preparative recycle HPLC system using a combination of ODS silica and cholester packed columns at over 99% purity. Their purities and structures of 3a and 3b thus obtained were confirmed by HPLC analysis and physical data (1H- and 13C-NMR, MS spectra, and X-ray crystallography).

Topics: Chemical Fractionation; Coumaric Acids; Magnetic Resonance Spectroscopy; Oryza; Phenylpropionates; Stereoisomerism