Gallic Acid-Dextran Conjugate: Green Synthesis of a Novel Antioxidant Molecule

Abstract

A novel derivative of dextran, dextran–gallic acid (Dex–Gal), obtained from simple conjugation with gallic acid, was synthesized by an efficient free radical-mediated method. To verify the synthesis of Dex–Gal, 1H-nuclear magnetic resonance (1H-NMR), Fourier transform infrared (FTIR) spectrometry, and high-performance size-exclusion chromatography (HPSEC) were employed. The results revealed the conjugation of gallic acid with the 15.5 kDa dextran from Leuconostoc mesenteroides. Dex–Gal had a molecular weight of 11.2 kDa, indicating that the conjugation reaction was accompanied by a minor degradation of Dex–Gal. In addition, Dex–Gal contained 36.8 ± 1.4 mg gallic acid per gram dextran. These molecules were also evaluated as antioxidants using total antioxidant capacity (TAC), reducing power, ferric chelation, and superoxide radical-scavenging assays. Both polysaccharides had no ferric chelation activity. In addition, Dex–Gal was more efficient as an antioxidant agent in TAC (13 times) and was more efficient than dextran in superoxide radical-scavenging (60 times) and reducing power (90 times) assays. These data demonstrate that Dex–Gal is a natural-compound-based antioxidant with potential applications in the pharmaceutical, cosmetic, and food industries.