Synthesis and Antioxidant Activity of Cationic 1,2,3-Triazole Functionalized Starch Derivatives

In this study, starch was chemically modified to improve its antioxidant activity. Five novel cationic 1,2,3-triazole functionalized starch derivatives were synthesized by using "click" reaction and N-alkylation. A convenient method for pre-azidation of starch was developed. The structures of the derivatives were analyzed using FTIR and H-1 NMR. The radicals scavenging abilities of the derivatives against hydroxyl radicals, DPPH radicals, and superoxide radicals were tested in vitro in order to evaluate their antioxidant activity. Results revealed that all the cationic starch derivatives (2a-2e), as well as the precursor starch derivatives (1a-1e), had significantly improved antioxidant activity compared to native starch. In particular, the scavenging ability of the derivatives against superoxide radicals was extremely strong. The improved antioxidant activity benefited from the enhanced solubility and the added positive charges. The biocompatibility of the cationic derivatives was confirmed by the low hemolytic rate (<2%). The obtained derivatives in this study have great potential as antioxidant materials that can be applied in the fields of food and biomedicine

Effect of different viscous rejuvenators on chemical and mechanical behavior of aged and recovered bitumen from RAP

© 2019 Elsevier Ltd Due to scarcity of virgin natural materials, the use of reclaimed asphalt pavement (RAP) has been promoted and encouraged in pavement engineering. However, note that the bituminous binder in RAP has been seriously aged due to long-term service exposure to the atmosphere. It is thus paramount to effectively restore properties of the RAP by adding proper rejuvenators. In this study, five rejuvenators were designed with different viscosities and applied to rejuvenate the aged binder. The changes in chemical compositions of bitumen caused by ageing and rejuvenating were evaluated by a SARA (Saturate, Aromatic, Resin and Asphaltene) analysis method. Brookfield viscosity, Dynamic Shear Rheometer (DSR) and Direct Tension (DT) were further conducted to evaluate the physical and mechanical properties of bituminous binders. Surface Free Energy test was applied to characterize the adhesion and moisture damage behavior of aged and rejuvenated binders. The experimental results showed that the ageing process increased resins and asphaltenes, which in turn improved the colloidal stability of the aged binder. The five rejuvenators designed in this research had a similar effect in restoring the rheological properties and stiffness of the aged bitumen to a similar level as that of the virgin binder. However, the viscosity level of rejuvenator has different impacts on tensile elongation at break, brittle fracture stress, adhesion property and moisture resistance of rejuvenated binders, in which the rejuvenator with an optimal viscosity may obtain the best rejuvenating performance

Novel Water Soluble Chitosan Derivatives with 1,2,3-Triazolium and Their Free Radical-Scavenging Activity

Chitosan is an abundant and renewable polysaccharide, which exhibits attractive bioactivities and natural properties. Improvement such as chemical modification of chitosan is often performed for its potential of providing high bioactivity and good water solubility. A new class of chitosan derivatives possessing 1,2,3-triazolium charged units by associating “click reaction” with efficient 1,2,3-triazole quaternization were designed and synthesized. Their free radical-scavenging activity against three free radicals was tested. The inhibitory property and water solubility of the synthesized chitosan derivatives exhibited a remarkable improvement over chitosan. It is hypothesized that triazole or triazolium groups enable the synthesized chitosan to possess obviously better radical-scavenging activity. Moreover, the scavenging activity against superoxide radical of chitosan derivatives with triazolium (IC50 &lt; 0.01 mg mL−1) was more efficient than that of derivatives with triazole and Vitamin C. In the 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl radical-scavenging assay, the same pattern were observed, which should be related to the triazolium grafted at the periphery of molecular chains

Phenolic Acid Functional Quaternized Chitooligosaccharide Derivatives: Preparation, Characterization, Antioxidant, Antibacterial, and Antifungal Activity

As a promising biological material, chitooligosaccharide (COS) has attracted increasing attention because of its unique biological activities. In this study, fourteen novel phenolic acid functional COS derivatives were successfully prepared using two facile methods. The structures of derivatives were characterized by FT-IR and 1H NMR spectra. The in vitro antioxidant activity experiment results demonstrated that the derivatives presented stronger 1,1-Diphenyl-2-picryl-hydrazyl (DPPH), superoxide, hydroxyl radical scavenging activity and reducing power, especially the N,N,N-trimethylated chitooligosaccharide gallic acid salt (GLTMC), gallic acid esterified N,N,N-trimethylated chitooligosaccharide (GL-TMC) and caffeic acid N,N,N-trimethylated chitooligosaccharide (CFTMC) derivatives. Furthermore, the antifungal assay was carried out and the results indicated that the salicylic acid esterified N,N,N-trimethylated chitooligosaccharide (SY-TMC) had much better inhibitory activity against Botrytis cinerea and Fusarium graminearum. Additionally, the results of the bacteriostasis experiment showed that the caffeic acid esterified N,N,N-trimethylated chitooligosaccharide (CF-TMC) had the potential ability to inhibit Escherichia coli and Staphylococcus aureus bacteria. Altogether, this study may provide a neoteric method to produce COS derivatives with significantly increased biological activities, which have potential use in food, medicine, and health care products and other related industries

The moisture absorption and retention abilities of carboxymethyl inulin and quaternized inulin

Two kinds of inlin derivatives, carboxymethyl inulin (CMI) and quaternized inulin (QI), were successfully synthesized. Their structural properties were characterized by FT-IR and their moisture absorption-retention ability were explored and compared with those of hyaluronic acid (HA), respectively. Carboxymethyl and quaternary ammonium salt groups are anionic and cationic groups, which are both hydrophilic Thereby, hydrogen bonds readily develop interactions between the derivatives' chains and water molecules. As a result, CMI and QI tended to hold more water molecules. Therefore, CMI and QI showed much stronger moisture absorption-retention ability than those of inulin. CMI should be further explored in cosmetic and clinical fields as HA substitute due to its more excellent moisture retention-absorption ability. &copy; 2010 IEEE

Preparation of chitosan derivatives containing aromatic five-membered heterocycles for efficient antimicrobial and antioxidant activities

In this study, nine chitosan derivatives containing aromatic five-membered heterocycles were prepared and the effects of different grafting methods on the biological activities of chitosan derivatives were investigated. The structures of all the compounds were characterized by Fourier Transform Infrared (FT-IR) spectroscopy and Nuclear Magnetic Resonance (NMR) spectroscopy, while the antioxidant, antifungal and antibacterial activities of the chitosan derivatives were tested. The experimental data suggested that the chitosan derivatives had outstanding inhibitory ability against Fusarium graminearum, Fusarium oxysporum f.sp.cucumbrum, Staphylococcus aureus and Escherichia coli. At the same time, some of the compounds showed strong scavenging ability against DPPH radical and superoxide radical. Cytotoxicity experiments have demonstrated that some chitosan derivatives are non-toxic to L929 cells. More importantly, compared to chitosan, these chitosan derivatives have good water solubility and can be used as potential polymers for antifungal and antibacterial biomaterials in agriculture

The influence of amino and hydroxyl of chitosan on hydroxyl radical scavenging activity

In order to determine the effect of the amido and hydroxyl of chitosan on antioxidant activity, a series of N-deacetylated chitosan with a degree of deacetylation (D.D.) ranging from 45% to 95% were prepared using region selective N-acetylation of chitosan. Their carboxymethyl derivatives (CMC) were also synthesized according to previous method. The antioxidant activity was evaluated on the basis of their abilities to scavenge hydroxyl radical. The results indicated that the hydroxyl radical scavenging ability depended on the degree of deacetylation and concentration. It also showed that the 2-NH 2 had a closer relation than 6-OH in hydroxyl radical scavenging activities. &copy;2009 Crown

Synthesis, Characterization, and the Antioxidant Activity of Phenolic Acid Chitooligosaccharide Derivatives

A series of phenolic acid chitooligosaccharide (COS) derivatives synthesized by two mild and green methods were illuminated in this paper. Seven phenolic acids were selected to combine two kinds of COS derivatives: the phenolic acid chitooligosaccharide salt derivatives and the phenolic-acid-acylated chitooligosaccharide derivatives. The structures of the derivatives were characterized by FT-IR and H-1 NMR spectra. The antioxidant experiment results in vitro (including DPPH-radical scavenging activity, superoxide-radical scavenging activity, hydroxyl-radical scavenging ability, and reducing power) demonstrated that the derivatives exhibited significantly enhanced antioxidant activity compared to COS. Moreover, the study showed that the phenolic acid chitooligosaccharide salts had stronger antioxidant activity than phenolic-acid-acylated chitooligosaccharide. The cytotoxicity assay of L929 cells in vitro indicated that the derivatives had low cytotoxicity and good biocompatibility. In conclusion, this study provides a possible synthetic method for developing novel and nontoxic antioxidant agents which can be used in the food and cosmetics industry

Preparation of l-Arginine Schiff Bases Modified Chitosan Derivatives and Their Antimicrobial and Antioxidant Properties

We successfully prepared a series of l-arginine Schiff bases acylated chitosan derivatives, aiming to improve the antioxidant activity and antimicrobial activity of chitosan by introducing a furan ring, pyridine ring, and l-arginine structure. The accuracy of the structures of ten compounds was characterized by FT-IR and H-1 NMR. In terms of DPPH radical scavenging activity, except for compound CR3PCA, the scavenging rate of other compounds was higher than chitosan, especially CRCF and CRBF had strong scavenging abilities. At the same time, in the superoxide-radical scavenging activity assay, CRCF, CRBF, CR3PCA, CR2C3PCA, and CR2B3PCA were comparable to positive control at 1.60 mg/mL. Simultaneously, CRFF, CRCF, and CRBF had a certain inhibitory effect on Botrytis cinerea. Furthermore, the inhibitory effect of CRFF, CRCF, and CR3PCA on Staphylococcus aureus was very well, close to the positive control at 1.00 mg/mL. CRCF and CR2B3PCA showed better inhibitory effects on Escherichia coli than other compounds. The MTT assay was used to determine the cytotoxicity of the chitosan derivatives, which proved their safety to fibroblast cells. In summary, the study indicated that some of these compounds have the potential for further development and utilization in the preparation of antioxidants and antimicrobial agents

New synthetic chitosan derivatives bearing benzenoid/heterocyclic moieties with enhanced antioxidant and antifungal activities

In this paper, several novel chitosan derivatives bearing benzenoid / heterocyclic moieties were synthesized via introducing aminobenzene and heterocyclic compounds onto carboxymethyl chitosan. The specific structures of chitosan derivatives were confirmed by FTIR, H-1 NMR, and elemental analysis. Meanwhile, the antioxidant efficiencies of chitosan derivatives were assayed in vitro. In particular, all chitosan derivatives showed significant improvement in superoxide-radical scavenging activity and DPPH radical scavenging activity. Their antifungal activities against two plant pathogenic fungi (Colletotrichum lagenarium and Phomopsis asparagi) were estimated in vitro by hyphal measurement, and all products exhibited excellent antifungal activity. Besides, the cytotoxicity of them was also measured by CCK-8 in vitro on L929 cells, and all samples showed low cytotoxicity. The good biocompatibility and enhanced biological activity of new synthetic chitosan derivatives might be obvious ad-vantages, while applied in wide range of applications as antifungal agents or antioxidants in food, medicine, cosmetics, and other fields