Synthesis and Antioxidant Activity of Hydroxycinnamic Acid Xylan Esters

Abstract

Naturally occurring hydroxycinnamic acids, such as ferulic and sinapic acids, are known to possess antioxidant activity. In this study, ferulic acid and sinapic acid were covalently attached to oat spelt arabinoxylan and birch wood glucuronoxylan by esterification in a two-step feasible synthesis to generate modified xylans with various degrees of substitution. The obtained derivatives were fully analyzed by FT-IR, NMR, and HPSEC experiments to confirm the esterification of xylans and the degree of substitution. The antioxidative potential of the conjugates was evaluated using the emulsion lipid oxidation test. The results demonstrate that the derivatized xylans inhibited lipid oxidation notably better than the native oat spelt and birch wood xylans. It was found that ferulic acid esters of glucuronoxylan were more efficient antioxidants than those of arabinoxylan and that sinapic acid xylan esters were more efficient than their ferulic acid counterparts.

Cleavage of Covalent Bonds in the Pyrolysis of Lignin, Cellulose, and Hemicellulose

“…The relatively large discrepancy in xylan may suggest that its structure in Figure 7 is oversimplified. It may also contain side groups, such as α-4-O-methylglucopyranosyluronic acid, α-L-arabi-nofuranosyl, xylopyranosyl moieties, or acetyl units, 35 which reduce its glucosidic bond content.…”

A review of bioactive plant polysaccharides: Biological activities, functionalization, and biomedical applications

“…(Ebringerová & Heinze, 2000;Petzold-Welcke, Schwikal, Daus, & Heinze, 2014;Pohjanlehto, Setälä, Kammiovirta, & Harlin, 2011). For example, introduction of antioxidant activity to xylans for biomedical applications could be achieved by esterification with ferulic acid and sinapic acid (Wrigstedt et al, 2010). Pentosan polysulfate, an FDA-approved oral medicine, was prepared by sulfation of beechwood xylan.…”

Synthesis and antioxidant property of hydroxycinnamoyl maltodextrin derivatives

“…The DS of VA‐g‐MD, CA‐g‐MD and FA‐g‐MD was 0.24, 0.76 and 0.81, respectively, under the same reaction conditions. Elsewhere, it was reported that the DS of ferulic acid grafted xylan was 0.86 under the optimal condition (Wrigstedt et al ., ). The similar DS of CA‐g‐MD and FA‐g‐MD in the present study may be due to the same of reaction environment and reactivity.…”

“…It was reported that feruloylated oligosaccharides, exhibiting great inhibition potential in the lipid peroxidation assay, did not perform well in the DPPH assay (Katapodis et al ., ). In addition, sinapic acid and ferulic acid have also been grafted to cellulose and xylan, and these prepared polymers displayed good antioxidant activity in inhibiting lipid peroxidation (Trombino et al ., ; Wrigstedt et al ., ). A possible explanation for the higher inhibition potential in the lipid peroxidation assay in this study might be an elevation in the solubility of the test media (Kylli et al ., ; Shimotori et al ., ).…”

“…The synthesis of ferulic acid grafted maltodextrin (FA‐ g ‐MD), vanillic acid grafted maltodextrin (VA‐ g ‐MD) and caffeic acid grafted maltodextrin (CA‐ g ‐MD) was performed referring to method described by Wrigstedt et al . () with some modifications. Briefly, the synthesis of hydroxycinnamoyl maltodextrin derivatives was carried out in two steps including the esterification of maltodextrin and deacetylation of maltodextrin hydroxycinnamic acid esters.…”