Antimicrobial and Antioxidant Activities of N-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases

Abstract

N-2-hydroxypropyltrimethyl ammonium chloride chitosan (HACC), a cationic quaternary ammonium salt polymer exhibiting good solubility in water, is widely used because of its low toxicity and good biocompatibility. Herein, through ion exchange reaction, we prepared N-2-hydroxypropyltrimethyl ammonium chitosan derivatives bearing amino acid Schiff bases with good biological activities. The accuracy of the structures was verified by FT-IR and 1H NMR. The antibacterial activity, antifungal activity, and scavenging ability of DPPH radical and superoxide radical of HACC derivatives were significantly improved compared with that of HACC. In particular, HACGM (HACC-potassium 2-((2-hydroxy-3-methoxybenzylidene)amino)acetate) and HACGB (HACC-potassium 2-((5-bromo-2-hydroxybenzylidene)amino)acetate) showed good inhibitory effect on bacteria and fungi, including Staphylococcus aureus, Escherichia coli, Botrytis cinerea, and Fusarium oxysporum f. sp. cubense. The inhibition rate of HACGB on Staphylococcus aureus and Escherichia coli could reach 100% at the concentration of 0.1 mg/mL, and the inhibition rate of HACGM and HACGB on Botrytis cinerea and Fusarium oxysporum f. sp. cubense could also reach 100% at the concentration of 0.5 mg/mL. Improving antimicrobial and antioxidant activities of HACC could provide ideas and experiences for the development and utilization of chitosan derivatives.

Preparation of Vanillin-Taurine Antioxidant Compound, Characterization, and Evaluation for Improving the Post-Harvest Quality of Litchi

“…Vanillin was reported to keep the activity of defense-related enzymes constant, including POD, PPO, and phenylalanine ammonia-lyase (PAL) in tomato fruit [ 18 ], it protected the grapes from postharvest rot caused by yeast, mold, and Botrytis cinerea , and extended the post-storage quality [ 19 , 20 ]. On the other hand, an amino acid derived Schiff base attracted more attention due to its special biological activities including antioxidant, and antibacterial [ 21 , 22 , 23 ]. Taurine is a naturally occurring amino acid that is widely distributed in human tissues and organs and was used as a supplementation or additive in food.…”

Hydrophilic Chitosan Derivatives: Synthesis and Applications

“…Chitosan and its modifications have a myriad of technology relevant properties, including antimicrobial, [32,[41][42] antifungal, [2,5,43] wound healing, [7,44] antioxidant, [41,45] materials chelator [10,27,38] and more. In the next paragraphs, we will present various modification-dependent chitosan applications.…”

“…cubense reaches 100 % at 0.5 mg mL À 1 concentration (Scheme 11). [41] Hefni et al showed that increasing the number of chitosan's amino groups using l-Ala esterification on C6À OH leads to an increase in adsorption efficiency. The uptake efficacy of three heavy metals (Mn 2 + , Pb 2 + , Al 3 + ) and total organic carbon (TOC) from wastewater was studied at different concentrations, temperatures, and contact times.…”

“…Schiff base derivatives of HACC amino acids. [41] Figure 2. Adsorption kinetics of histidine-modified chitosan beads at 25 °C, pH 5, and a copper(II) nitrate concentration of 0.47 mmol L À 1 .…”

The Studies on Chitosan for Sustainable Development: A Bibliometric Analysis

“…Chitosan, with amino acid modification, is biocompatible for wound healing and tissue generation [ 8 , 9 ]. Chitosan can also be modified for antibacterial and antifungal properties to inhibit the growth of E. coli and B. cinerea [ 10 ]. Chitosan-based sprays and aerogels provide a significant reduction in bacterial growth and are good for food packaging [ 11 , 12 ].…”