Abstract

Introduction: The aim of this study is to determine appropriate parameters in the synthesis of syringic acid onto chitooligosaccharides (COSs) with an ascorbic acid/hydrogen peroxide redox pair in order to obtain the derivative with the highest grafting degree.

Methods: In this study, syringic acid grafted COSs, catalysed by an ascorbic acid/hydrogen peroxide redox pair were investigated. The synthesis conditions were investigated, including the mass ratio between syringic acid and COSs, pH, temperature and synthesis time. Characteristics of the derivative were evaluated by Thin Layer Chromatography (TLC), Ultraviolet-Visible (UV-vis) and Fourier Transform Infrared (FT-IR) spectroscopy. The activities of COSs and derivative were evaluated by antimicrobial ability.

Results: The results showed, that the best conditions for the synthesis were the mass ratio between syringic acid and COSs at 0.5:1, pH 5, temperature 27^oC, for 6 hours with grafting degree at 32%. The TLC assay showed, that free ascorbic acid and syringic acid are not present in the product. The UV-vis and FT-IR data confirmed, that syringic acid was successfully conjugated onto COSs. Furthermore, the antibacterial assay showed that syringic acid grafted onto COSs had minimum inhibitory concentration against foodborne pathogenic bacteria at 1%.

Conclusion: The syringic acid onto chitooligosaccharides were successfully synthesized by free radical mediated grafting method with an ascorbic acid/hydrogen peroxide redox pair. The grafting degree of syringic acid onto COSs was greatly affected by many factors, including COSs, syringic acid, pH, as well as temperature and time of reaction. Moreover, the new derivative showed enhanced antibacterial capabilities, as compare to free COSs.