Non-radical synthesis of amide chitosan with p-coumaric acid and caffeic acid and its application in pork preservation

Peng, Fei; Zhang, Zhigang; Wu, You‐Lin; Xiao, Liping; Zhuang, Yuanhong; Ding, Nengshui; Huang, Bingqing

doi:10.1016/j.ijbiomac.2022.09.263

Cited by 17 publications

(3 citation statements)

References 40 publications

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“…One intriguing compound that has attracted attention due to its potential synergistic effects with CS is caffeic acid (CA), a polyphenol compound. CA is well known for its antibacterial, antiviral, antioxidant, and anti-inflammatory properties, while also demonstrating promising anti-cancer effects in several studies [ 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Characterization of Chitosan Films Modified Using Caffeic Acid and a Neutralization Process

Szulc

Lewandowska

2023

Materials

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In the context of the growing interest in biopolymer-based materials for various applications, this study aimed to enhance the properties of chitosan (CS, a derivative of chitin) films by incorporating caffeic acid, a polyphenol compound known for its multiple health benefits. The objective was to improve the mechanical parameters of the resulting films, including surface roughness and elasticity. CS was combined with caffeic acid and then underwent a neutralization process. The modified films exhibited potential for use in soft tissue engineering, where increased elasticity and surface roughness are desirable characteristics. The main methods employed to evaluate the structure and properties of the films included mechanical analysis, infrared spectroscopy, scanning electron microscopy, atomic force microscopy, thermogravimetric analysis, contact angle measurement, and swelling behavior. The study’s main findings revealed significant alterations in the mechanical properties and surface morphology of the films. The main conclusions drawn from the study suggest that interactions between caffeic acid and CS hold promise for the development of advanced biomaterials in medicine, tissue engineering, and cosmetic formulations. However, a deeper understanding of these interactions is necessary to optimize the material properties and unlock their full potential.

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Section: Introductionmentioning

confidence: 99%

Characterization of Chitosan Films Modified Using Caffeic Acid and a Neutralization Process

Szulc

Lewandowska

2023

Materials

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“…Compared with CS, the introduction of phenolic acid can increase the antioxidant activity and antibacterial performance of CS, which has potential application in the food preservation. Conjugates with a high substitution were obtained and were similar to that reported in previous study (Liu et al ., 2014; Fei et al ., 2022; Huang et al ., 2022).…”

Section: Resultsmentioning

confidence: 99%

“…However, the increased antibacterial activity of CS‐g‐CA should be mainly attributed to the function of CA fraction. The antibacterial activity of CA is related to its structure with two hydroxyl groups (Fei et al ., 2022). At the same time, the molecular weight of CS‐g‐CA was obtained by increasing the grafting reaction, and forming an impermeable membrane on the outer surface of cell, thus blocking the transport of essential nutrients to cell, and ultimately leading to cell death.…”

Section: Resultsmentioning

confidence: 99%

Carbodiimide‐mediated grafting of caffeic acid on chitosan to improve its physicochemical and biological properties: used for Pompano (Trachinotus ovatus) preservation

Lan

Zhang

Liu

et al. 2023

Int J of Food Sci Tech

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SummaryChitosan‐grafted caffeic acid (CS‐g‐CA) was successfully prepared using carbodiimide‐based chemical coupling method. The results of UV–vis and FT‐MIR showed that caffeic acid (CA) was successfully grafted onto chitosan (CS). The grafting degree of CA in CS determined by Folin–Ciocalteu scheme was up to 91.26 ± 2.58 mg g−1. Compared with CS solution, CS‐g‐CA solution has lower apparent viscosity and thermal stability. The results of SEM demonstrated that the grafting treatment changed the microstructure of CS. The grafting of the CA on CS enhanced its antioxidant activity. It can be seen that the clearance rate of DPPH (82.52% ± 0.7%), ABTS+ free radicals (88.21% ± 0.26%), T‐AOC (94.91% ± 0.21%) and FRAP (13.51 ± 0.52 mmol L−1 FeSO4) of CS‐g‐CA was similar to ascorbic acid at 2.0 mg mL−1. The results of antibacterial experiments demonstrated that CS‐g‐CA had better antibacterial ability in vitro, and the diameter of inhibition zone of 20.0 mg mL−1 CS‐g‐CA against Pseudomonas fluorescens and Staphylococcus saprophyticus was 16.88 ± 0.05 mm and 19.17 ± 0.09 mm, respectively, and it was significantly higher than CS (11.25 ± 0.04 mm and 13.09 ± 0.07 mm). The texture and freshness of Control group and CS rapidly declines post‐mortem. CS‐g‐CA treatment could effectively retard the deterioration of texture and keep the better quality of Pompanos (Trachinotus ovatus). This study indicates that grafting CA onto CS alters the biological activity and physicochemical properties of CS.

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Photocrosslinkable hydrogel of ibuprofen‐chitosan methacrylate modulates inflammatory response

Guan,

Yao,

2024

J Biomedical Materials Res

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Methacrylated biopolymers are unique and attractive in preparing photocrosslinkable hydrogels in biomedical applications. Here we report a novel chitosan (CS) derivative‐based injectable hydrogel with anti‐inflammatory capacity via methacrylation modification. First, ibuprofen (IBU) was conjugated to the backbone of CS by carbodiimide chemistry to obtain IBU‐CS conjugate, which converts water‐insoluble unmodified CS into water‐soluble IBU‐CS conjugate. The IBU‐CS conjugate did not precipitate at the pH of 7, which was beneficial to subsequent chemical modification with methacrylic anhydride to prepare IBU‐CS methacrylate (IBU‐CS‐MA) with significantly higher methacrylation substitution. Photocrosslinkable in situ gel formation of injectable IBU‐CS‐MA hydrogel was verified using lithium phenyl‐2,4,6‐trimethylbenzoylphosphinate (LAP) initiator under visible light. The IBU‐CS‐MA hydrogel showed good cytocompatibility as revealed by encapsulating and in vitro culturing murine fibroblasts within hydrogels. It promoted macrophage polarization toward M2 phenotype, as well as downregulated pro‐inflammatory gene expression and upregulated anti‐inflammatory gene expression of macrophages. The hydrogel also significantly reduced the reactive oxygen specifies (ROS) and nitrogen oxide (NO) produced by lipopolysaccharides (LPS)‐stimulated macrophages. Upon subcutaneous implantation in a rat model, it significantly mitigated inflammatory responses as shown by significantly lower inflammatory cell density, less cell infiltration, and much thinner fibrous capsule compared with CS methacrylate (CS‐MA) hydrogel. This study suggests that IBU‐CS conjugate represents a feasible strategy for preparing CS‐based methacrylate hydrogels for biomedical applications.

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Non-radical synthesis of amide chitosan with p-coumaric acid and caffeic acid and its application in pork preservation

Cited by 17 publications

References 40 publications

Characterization of Chitosan Films Modified Using Caffeic Acid and a Neutralization Process

Characterization of Chitosan Films Modified Using Caffeic Acid and a Neutralization Process

Carbodiimide‐mediated grafting of caffeic acid on chitosan to improve its physicochemical and biological properties: used for Pompano (Trachinotus ovatus) preservation

Photocrosslinkable hydrogel of ibuprofen‐chitosan methacrylate modulates inflammatory response

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