Insight into structure-activity relationships of hydroxycinnamic acids modified porous starch: The effect of phenolic hydroxy groups

Abstract

Antioxidant capacity of hydroxycinnamic acids-modified starch mainly depends on their chemical structure. Herein, cinnamic acid as well as meta-substituted and para-substituted cinnamic acid were selected for esterification with porous starch (labelled as CA@PS, m-CA@PS and p-CA@PS), with the successful formation of porous starch (labelled as PS) esters then confirmed by ¹H NMR, ¹³C solid-state NMR and FT-IR spectroscopy. Three PS esters with almost same degrees of substitution (DS) were obtained, and antioxidant assays, including DPPH radical scavenging, reducing power and hydroxyl radical scavenging tests, were subsequently used to evaluate the antioxidant activity of the esterified PS. Overall, CA@PS showed weak antioxidant activity because of the absence of phenolic hydroxy, while p-CA@PS displayed better antioxidant capacity. Because its conjugated structure offered the stronger electron-donating effect, that could enhance antioxidant capacity. Therefore, antioxidant capacity depended significantly on overall chemical structure, including numbers and substitution positions of phenolic hydroxy groups.

Keywords: Antioxidant activity; Hydroxycinnamic acids; Porous starch; Structure-activity relationships.