Synthesis, Characterization, and Antifungal Property of Hydroxypropyltrimethyl Ammonium Chitosan Halogenated Acetates

Abstract

Hydroxypropyltrimethyl ammonium chitosan halogenated acetates were successfully synthesized from six different haloacetic acids and hydroxypropyltrimethyl ammonium chloride chitosan (HACC) with high substitution degree, which are hydroxypropyltrimethyl ammonium chitosan bromacetate (HACBA), hydroxypropyltrimethyl ammonium chitosan chloroacetate (HACCA), hydroxypropyltrimethyl ammonium chitosan dichloroacetate (HACDCA), hydroxypropyltrimethyl ammonium chitosan trichloroacetate (HACTCA), hydroxypropyltrimethyl ammonium chitosan difluoroacetate (HACDFA), and hydroxypropyltrimethyl ammonium chitosan trifluoroacetate (HACTFA). These chitosan derivatives were synthesized by two steps: first, the hydroxypropyltrimethyl ammonium chloride chitosan was synthesized by chitosan and 3-chloro-2-hydroxypropyltrimethyl ammonium chloride. Then, hydroxypropyltrimethyl ammonium chitosan halogenated acetates were synthesized via ion exchange. The structures of chitosan derivatives were characterized by Fourier transform infrared spectroscopy (FTIR), 1H Nuclear magnetic resonance spectrometer (1H NMR), 13C Nuclear magnetic resonance spectrometer (13C NMR), and elemental analysis. Their antifungal activities against Colletotrichum lagenarium, Fusarium graminearum, Botrytis cinerea, and Phomopsis asparagi were investigated by hypha measurement in vitro. The results revealed that hydroxypropyltrimethyl ammonium chitosan halogenated acetates had better antifungal activities than chitosan and HACC. In particular, the inhibitory activity decreased in the order: HACTFA > HACDFA > HACTCA > HACDCA > HACCA > HACBA > HACC > chitosan, which was consistent with the electron-withdrawing property of different halogenated acetates. This experiment provides a potential idea for the preparation of new antifungal drugs by chitosan.

Modification of Hydroxypropyltrimethyl Ammonium Chitosan with Organic Acid: Synthesis, Characterization, and Antioxidant Activity

“…There are abundant marine resources which can be developed into antioxidant alternatives. Chitosan, (1-4)-2-amino-2-deoxy-b-d-glucan, is one of the marine bioactive compounds, which can be readily prepared by the N-deacetylation from chitin [2,9,10]. In the last few years, chitosan has attracted significant attention in chemical industry, maquillage, papermaking, and food science because of its excellent physical and chemical properties such as biodegradability, non-toxicity, biocompatibility, bioactivity and other properties [11,12].…”

“…It is worth noticing that most hydroxyl acids have both carboxyl (-COOH) and hydroxyl (-OH) groups, which can easily react with chitosan. In previous studies, we used halogen compounds to modify chitosan to obtain a series of chitosan derivatives with antifungal activity [9]. So, we consider modifying chitosan with hydroxy acids.…”

Estimation of the antifungal activity of some preparations against Diaporthe eres under in vitro conditions

“…This approach is particularly common against Diaporthe neoviticola (Phomopsis viticola) because of the substantial damage this pathogen causes to grapevines and the worldwide prevalence and economic importance of this plant [5,17,[22][23][24]. However, excessive use of chemical fungicides has caused serious ecological and environmental damage [25]. Therefore, novel agents with low toxicity and strong antifungal activity are urgently needed.…”

“…There are many bioactive compounds in the environment which can be developed into fungicide alternatives [26][27][28][29]. These include chitosan and grapefruit extract [23,25,[29][30][31][32][33][34][35][36], which exhibit antibacterial activity and biodegradable, nontoxic and capable of directly limit the growth and development of various species of pathogens. These agents can be applied directly before the harvest as they have no currency and prevention date.…”

“…In addition, they also have the ability to induce a defense response against pathogenes. Due to their unique physical and chemical properties, they are used in agriculture, medicine, food science, industry, and environmental remediation [25,30,31,[37][38][39].…”