Synthesis and properties of feruloyl corn bran arabinoxylan esters

Int J Cosmet Sci. 2016 Jun;38(3):238-45. doi: 10.1111/ics.12281. Epub 2015 Nov 9.

Abstract

Objective: To enhance the antioxidant activity and UV absorption coefficient of corn bran arabinoxylan (CAX), ferulic acid (FA) with this physiological activity is used to modify CAX.

Methods: Corn bran arabinoxylan was extracted from corn bran according to alkaline hydrogen peroxide (AHP) method. FA was covalently linked to CAX by esterification in a two-step feasible synthesis to generate ferulic acid arabinoxylan esters (FA-CAX). The structure and molecular weight of FA-CAX were characterized by NMR and HPSEC, the degrees of substitution (DS) was determined by HPLC, and the ultraviolet (UV) coefficient of FA-CAX was tested by UV spectroscopy. The antioxidant activity of FA-CAX was investigated on the basis of 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical assay, and protecting ability of FA-CAX to UV-induced oxidative damage was tested using linolenic acid dispersion as stratum corneum lipid model.

Results: The results demonstrated that FA was attached to CAX successfully, and the inherent structure of CAX would not be broken during the process of the synthesis. FA-CAX-1 and FA-CAX-2 contained different amount of FA, with DS at 0.33 and 1.25, respectively, can absorb UV both at UVA and UVB. Moreover, FA-CAX-2 exhibited better antioxidant activity than FA-CAX-1 based on the two test methods.

Conclusion: Ferulic acid modified CAX had significant antioxidant ability and UV absorption coefficient. And higher amount of FA leads to higher antioxidant activity and stronger UV absorption and stability. With increasing amount of FA attached to CAX, the antioxidant activities were better and the UV absorption was stronger and more durable.

Keywords: antioxidant; arabinoxylan; chemical synthesis; corn bran; ferulic acid; ultraviolet.

MeSH terms

  • Coumaric Acids / chemistry*
  • Esters
  • Molecular Weight
  • Spectrum Analysis / methods
  • Xylans / chemistry*
  • Zea mays / chemistry*

Substances

  • Coumaric Acids
  • Esters
  • Xylans
  • arabinoxylan
  • ferulic acid