scholarly journals Synthesis, characterization, and antioxidant activity of carboxymethyl chitosan derivatives containing sulfonium salt

Author(s):  
Xueqi Sun ◽  
Jingjing Zhang ◽  
Yingqi Mi ◽  
Qin Miao ◽  
Wenqiang Tan ◽  
...  
Polymers ◽  
2019 ◽  
Vol 11 (11) ◽  
pp. 1810 ◽  
Author(s):  
Xueqi Sun ◽  
Jingjing Zhang ◽  
Yuan Chen ◽  
Yingqi Mi ◽  
Wenqiang Tan ◽  
...  

A new class of chitosan derivatives possessing thiourea salts were synthesized to improve the solubility and the antioxidant activity of chitosan. Firstly, chitosan was modified to carboxymethyl chitosan, combining carboxymethyl chitosan with thiourea salts that have different structures to form new chitosan derivatives. The chitosan and chitosan derivatives were characterized by FT-IR, 13C NMR, TGA, and elemental analyses. The new peaks of thiourea salts could be clearly observed at about 1240 cm–1 in the IR spectra, and the peak of C=S was clearly observed at around 180 ppm in the 13C NMR. IR spectra and 13C NMR of the structural units of these polymers validated the chitosan derivatives possessing thiourea salts were successfully synthesized. Their antioxidant properties were tested, including DPPH-radical scavenging ability, superoxide-radical scavenging ability, and hydroxyl-radical scavenging ability. Our results suggested the increase of thiourea salt groups in chitosan derivatives promotes the scavenging effect. The scavenging activity of 4TMCMCS, TMCMCS. 4,4DCMCS, and 4ACMCS against DPPH-radical and superoxide-radical were more than 90% at 1.6 mg/mL, respectively. In the cytotoxicity assay, no cytotoxicity was observed for the L929 cells with chitosan and its derivatives at all testing concentrations. These results demonstrated that the combination of chitosan and thiourea salt groups improved the antioxidant activity of chitosan, and the antioxidants or free radical scavengers based on natural polymers and thiourea salts showed potential applications.


Coatings ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 604
Author(s):  
Liyan Wang ◽  
Liang Lei ◽  
Kang Wan ◽  
Yuan Fu ◽  
Hewen Hu

Active films based on carboxymethyl chitosan incorporated corn peptide were developed, and the effect of the concentration of corn peptide on films was evaluated. Physicochemical properties of the films, including thickness, opacity, moisture content, color, mechanical properties, water vapor permeability, and oil resistance, were measured. Biological activities of the films, including the antioxidant and antibacterial activities, were characterized in terms of 2, 2-diphenyl-1-picrylhydrazyl free radical scavenging activity, reducing power, the total antioxidant activity, and the filter disc inhibition zone method. The results indicated that the incorporation of corn peptide caused interactions between carboxymethyl chitosan and corn peptide in Maillard reaction and gave rise to the films light yellow appearance. Compared with the Control, the degree of glycosylation, browning intensity, thickness, opacity, tensile strength, antioxidant activity, and antibacterial activity of films were increased, but the elongation, vapor permeability, and oil resistance of films were decreased. The films based on corn peptide and carboxymethyl chitosan can potentially be applied to food packaging.


Foods ◽  
2020 ◽  
Vol 9 (11) ◽  
pp. 1604
Author(s):  
Yu Xiao ◽  
Chi-Tang Ho ◽  
Yulian Chen ◽  
Yuanliang Wang ◽  
Zihao Wei ◽  
...  

Genistein is one of major isoflavones derived from soybean products and it is believed to have beneficial effects on human health. However, its low water-solubility and poor oral bioavailability severely hamper its use as a functional food ingredient or for pharmaceutical industry. In this study, zein and zein/carboxymethyl chitosan (CMCS) nanoparticles were prepared to encapsulate genistein using a combined liquid–liquid phase separation method. The physicochemical properties of fabricated nanoparticles were characterized by dynamic light scattering (DLS), atomic force microscopy (AFM), and Fourier transform infrared spectroscopy (FTIR). The results demonstrated that genistein encapsulated with zein nanoparticles significantly improved its water dispersibility, antioxidant activity in the aqueous phase, and photostability against UV light. Moreover, genistein encapsulated in zein nanoparticles showed a sustained release property. Furthermore, it was found that encapsulation efficiency of genistein was significantly enhanced after CMCS coating, and this effect was more pronounced after the complex nanoparticles cross-linked with calcium ions when compared with the use of zein as a single encapsulant. In addition, compared to zein nanoparticles without biopolymer coating, CMCS coating significantly enhanced the thermal and storage stability of the formed nanoparticles, and delayed the release of genistein. A schematic diagram of zein and zein/carboxymethyl chitosan (CMCS) nanoparticles formation mechanism for encapsulation of genistein was proposed. According to the results of the current study, it could be concluded that encapsulation of genistein in zein/CMCS nanoparticles is a promising approach to improve its water dispersibility, antioxidant activity, photostability against UV light and provide controlled release for food/pharmaceutical applications.


2019 ◽  
Vol 10 (12) ◽  
pp. 1480-1488 ◽  
Author(s):  
Qing Li ◽  
Lijie Wei ◽  
Jingjing Zhang ◽  
Guodong Gu ◽  
Zhanyong Guo

A new class of chitosan derivatives possessing coumarins was synthesized to improve the antioxidant activity of chitosan.


2005 ◽  
Vol 15 (20) ◽  
pp. 4600-4603 ◽  
Author(s):  
Zhanyong Guo ◽  
Ronge Xing ◽  
Song Liu ◽  
Huahua Yu ◽  
Pibo Wang ◽  
...  

2008 ◽  
Vol 18 (21) ◽  
pp. 5774-5776 ◽  
Author(s):  
Tao Sun ◽  
Qian Yao ◽  
Dongxiang Zhou ◽  
Fang Mao

Polymers ◽  
2018 ◽  
Vol 10 (4) ◽  
pp. 395 ◽  
Author(s):  
Fang Luan ◽  
Lijie Wei ◽  
Jingjing Zhang ◽  
Yingqi Mi ◽  
Fang Dong ◽  
...  

Polymers ◽  
2020 ◽  
Vol 12 (11) ◽  
pp. 2460
Author(s):  
Yingqi Mi ◽  
Wenqiang Tan ◽  
Jingjing Zhang ◽  
Zhanyong Guo

A novel and green method for the preparation of chitosan derivatives bearing organic acids was reported in this paper. In order to improve the antioxidant activity of chitosan, eight different hydroxypropyltrimethyl ammonium chitosan derivatives were successfully designed and synthesized via introducing of organic acids onto chitosan by mild and non-toxic ion exchange. The data of Fourier Transform Infrared (FTIR), 13C Nuclear Magnetic Resonance (NMR), 1H NMR, and elemental analysis for chitosan derivatives indicated the successful conjugation of organic acid salt with hydroxypropyltrimethyl ammonium chloride chitosan (HACC). Meanwhile, the antioxidant activity of the chitosan derivatives was evaluated in vitro. The results indicated that the chitosan derivatives possessed dramatic enhancements in DPPH-radical scavenging activity, superoxide-radical scavenging activity, hydroxyl radical scavenging ability, and reducing power. Furthermore, the cytotoxicity of the synthesized compounds was investigated in vitro on L929 cells and showed low cytotoxicity. Thus, the enhanced antioxidant property of all novel chitosan products might be a great advantage, while applied in a wide range of applications in the form of antioxidant in biomedical, food, and cosmetic industry.


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