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

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, a...

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Bibliographic Details
Published in:Antioxidants 2019-10, Vol.8 (10), p.478
Main Authors: Queiroz, Moacir Fernandes, Sabry, Diego Araujo, Sassaki, Guilherme Lanzi, Rocha, Hugo Alexandre Oliveira, Costa, Leandro Silva
Format: Article
Language:English
Subjects:
antioxidant polysaccharide
Antioxidants
Chelation
Dextran
Food industry
Fourier transforms
Gallic acid
gallic acid-grafted dextran
Hydrocarbons
Hydrogen bonds
leuconostoc dextran
Molecular weight
NMR
Nuclear magnetic resonance
Polymers
Polysaccharides
Potassium
Sodium
Spectrum analysis
Superoxide
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Summary: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.
ISSN:2076-3921
2076-3921
DOI:10.3390/antiox8100478