The evaluation of antioxidant and antifungal properties of 6-amino-6-deoxychitosan in vitro

Abstract

We synthesized 6-amino-6-deoxychitosan (NCS) through a series of reactions from chitosan (CS). The antioxidant ability of CS and NCS were investigated in vitro, including that of DPPH-radical and hydrogen peroxide, reducing power, chelating abilities and inhibition of lipid peroxidation. As expected, after the introduction of amino groups, antioxidant ability had improved significantly. Especially, scavenging effect against DPPH-radical and hydrogen peroxide of NCS were 97% and 92% at 1.6mg/mL, respectively. Moreover, inhibition of lipid peroxidation was 57% at 0.1mg/mL. And the reducing power of NCS was 0.68 at 0.8mg/mL. Meanwhile, inhibitory effects against four fungi were also tested. Antifungal activity of NCS were better than those of CS and antifungal activity had improved more than 20% at 0.5mg/mL against these four kinds of plant pathogens. Based on the above results, it was reasonable to speculate that the obtained antioxidant ability and antifungal activity of NCS might benefit from amino groups on chitosan backbone. These in vitro results suggest the possibility that NCS as antioxidant compound could be effectively alleviate oxidative stress and thus inhibit the oxidative mechanisms that lead to degenerative diseases.

Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation

“…This procedure follows one in our previous paper (Luan et al, 2018). To a 500 mL round-bottomed flask equipped with a magnetic stir bar was dissolved 6-bromo-6-deoxy-N-phthaloyl chitosan 4 (3.54 g, 10 mmol) in NMP (100 mL).…”

Synthesis of Novel Chitin Derivatives Bearing Amino Groups and Evaluation of Their Antifungal Activity

“…There was a relationship between the antibacterial or antifungal activity of polysaccharide and the free amino groups. The greater the number of amino groups in the polysaccharide derivatives, the better their antifungal activity was [ 19 , 33 ], which confirmed the crucial role of amino groups in enhancing the antifungal activity of chitin. For this reason, NCT and DNCT have more amino compared to CT, which could be expected to have a more potent antifungal activity.…”

“…It has been reported that the presence of the amino groups in polysaccharide enables distinctive biological functions, such as anticoagulant activity, antibacterial property, and antioxidant activity [ 15 , 16 , 17 ]. Meanwhile, it was found that the antifungal activity of carbohydrate derivatives against the plant pathogenic fungi increased with an increase in active amino groups substituent [ 18 , 19 ]. Inspired it, amino can be immobilized on chitin at the 3-OH and 6-OH positions to further improve the biological activities of such derivatives.…”

Synthesis and Characterization of Inulin Derivatives Bearing Urea Groups with Promising Antifungal Activity

“…Antifungal assays were performed by the following plate growth rate method described by Luan . Briefly, the compounds were dissolved in water at a concentration of 5.0 mg mL −1 .…”