Synthesis of chitosan-gallic acid conjugate: Structure characterization and in vitro anti-diabetic potential

Liu, Jun; Lü, Jianfeng; Kan, Juan; Jin, Changhai

doi:10.1016/j.ijbiomac.2013.09.032

Cited by 176 publications

(131 citation statements)

References 31 publications

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“…Chitosan solution was sufficiently diluted (5 g/L) for optimum accessibility of phenolic acid monomers to the active sites of chitosan. Earlier it has been observed that with increasing viscosity of chitosan solution, grafting ratio of phenolic acids to chitosan decreases (Liu et al 2013). The yield of chitosanphenolic acid conjugates varied between 58 and 65 %.…”

Section: Resultsmentioning

confidence: 97%

“…Then the OH· abstracts hydrogen from amino and hydroxyl group of chitosan resulting in chitosan macro radicals. The corresponding phenolic acid molecules become acceptors of chitosan macro radicals, thus forming chitosan-phenolic acid conjugates (Liu et al 2013). Chitosan solution was sufficiently diluted (5 g/L) for optimum accessibility of phenolic acid monomers to the active sites of chitosan.…”

Section: Resultsmentioning

confidence: 99%

“…Grafting phenolic acids on chitosan may provide these compounds with the much needed stability and slow release. In consonance to this, recently, antidiabetic potential of chitosan gallic acid conjugate has been documented (Liu et al 2013). Vanillic acid, the oxidized form of vanillin is found at high concentrations in vanilla beans.…”

Section: Introductionmentioning

confidence: 83%

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Vanillic acid and coumaric acid grafted chitosan derivatives: improved grafting ratio and potential application in functional food

et al. 2015

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Chemically modified biofunctional chitosan derivatives may open up new applications in functional food and nutraceuticals development. Two new conjugates, namely vanillic acid and coumaric acid grafted chitosan derivatives were developed and comparative evaluation of their antioxidant and antimicrobial activities was carried out with ferulic acid and gallic acid grafted chitosan. The synthesized water soluble (1.0-4.5 mg/mL) chitosan-phenolic acid conjugates showed characteristic FTIR-spectroscopy band at around 1644 and 2933 cm −1 . Free phenolic acid was not observed in TLC plate of the chitosan-phenolic acid conjugates and UV-vis spectra showed primary absorption peak of the corresponding phenolic acids confirming the grafting reaction. Total antioxidant activity of the chitosan-phenolic acid derivatives ranged from~12 to 29 g ascorbic acid equivalent/100 g of the conjugate. Minute quantity of the derivatives (~57-162 μg and 82-109 μg respectively) could give 50 % inhibition of 2, 2′-diphenyl-1-picrylhydrazyl radical and hydroxyl free radical. Broad spectrum antibacterial activity was observed for all four derivatives against an array of foodborne pathogens and spoilage bacteria. Coumaric acid grafted chitosan showed promise as a food preservative as it inhibited the growth of several foodborne pathogens and spoilage bacteria, including Staphylococcus aureus. Among all the four derivatives, ferulic acid and gallic acid grafted chitosan had lowest minimum inhibitory concentration against Staphylococcus aureus and Pseudomonas aeruginosa respectively.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

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Vanillic acid and coumaric acid grafted chitosan derivatives: improved grafting ratio and potential application in functional food

et al. 2015

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“…Phenolic acid-functionalized chitosan has been shown to possess antioxidant, antitumor, antimicrobial, antidiabetic properties and also used as adsorptive, encapsulation, and packing materials for immobilization and delivering of drugs [23,24,25,26,27]. In addition to the above findings, the present study evaluates the antimicrobial and virulence inhibitory potential of CFA against human pathogenic bacteria.…”

Section: Discussionmentioning

confidence: 99%

Antibacterial and Biofilm Modulating Potential of Ferulic Acid-Grafted Chitosan against Human Pathogenic Bacteria

Dasagrandhi

Park

Jung

et al. 2018

IJMS

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The emergence of more virulent forms of human pathogenic bacteria with multi-drug resistance is a serious global issue and requires alternative control strategies. The current study focused on investigating the antibacterial and antibiofilm potential of ferulic acid-grafted chitosan (CFA) against Listeria monocytogenes (LM), Pseudomonas aeruginosa (PA), and Staphylococcus aureus (SA). The result showed that CFA at 64 µg/mL concentration exhibits bactericidal action against LM and SA (>4 log reduction) and bacteriostatic action against PA (<2 log colony forming units/mL reduction) within 24 h of incubation. Further studies based on propidium iodide uptake assay, measurement of material released from the cell, and electron microscopic analysis revealed that the bactericidal action of CFA was due to altered membrane integrity and permeability. CFA dose dependently inhibited biofilm formation (52–89% range), metabolic activity (30.8–75.1% range) and eradicated mature biofilms, and reduced viability (71–82% range) of the test bacteria. Also, the swarming motility of LM was differentially affected at sub-minimum inhibitory concentration (MIC) concentrations of CFA. In the present study, the ability of CFA to kill and alter the virulence production in human pathogenic bacteria will offer insights into a new scope for the application of these biomaterials in healthcare to effectively treat bacterial infections.

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“…Phenolic compounds extracted from plants, including gallic acid, catechin, caffeic acid, tannic acid, ferulic acid, and quercetin have been grafted to biomacromolecules, such as chitosan (CS) and its derivatives, gelatin, alginate, and inulin. 2,7−16 The synthesized antioxidant-polymer conjugates showed diverse bioactivities, including antioxidant, 17 anticancer, 18 and inhibitory effects on digestive enzymes, 19 β-secretase, 20 and food-borne pathogens. 21 CS, a natural copolymer of β-(1 → 4)-linked D-glucosamine and N-acetyl-D-glucosamine produced by deacetylation of chitin, is currently receiving considerable attention for its potential applications in biomedical, food, and chemical industries.…”

Section: ■ Introductionmentioning

confidence: 99%

Grafting of Gallic Acid onto Chitosan Enhances Antioxidant Activities and Alters Rheological Properties of the Copolymer

Xie

Hu²,

Wang³

et al. 2014

J. Agric. Food Chem.

282

143

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A new, simple, and effective method to graft gallic acid (GA) onto chitosan (CS) in aqueous solution in the presence of carbodiimide and hydroxybenzotriazole was developed. The grafting amount of GA reached as much as 209.9 mg/g of copolymer, which appears as the highest one among the reported literature, and the grafting degree of GA to CS was adjustable with modulation of the mass ratio of GA to CS. The covalent insertion of GA onto the polymeric backbones was confirmed by UV-vis and (1)H NMR analyses. Grafting endowed the resulting copolymer GA-grafted-CS (GA-g-CS) with both the advantages of CS and GA. The antioxidant capacity of GA-g-CS was much higher than that of the plain CS examined by assays of DPPH, superoxide, and ABTS radicals scavenging activities, reducing power, chelating power, inhibition of lipid peroxidation, ferric reducing antioxidant potential, and β-carotene-linoleic acid assays. Particularly, GA-g-CS showed significantly higher antioxidant activity than GA in β-carotene-linoleic acid assay. Furthermore, the viscosity of GA-g-CS was significantly higher than that of CS. The present study developed a novel approach to synthesize GA-g-CS that could be a potential biomaterial in food industries.

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Synthesis of chitosan-gallic acid conjugate: Structure characterization and in vitro anti-diabetic potential

Cited by 176 publications

References 31 publications

Vanillic acid and coumaric acid grafted chitosan derivatives: improved grafting ratio and potential application in functional food

Vanillic acid and coumaric acid grafted chitosan derivatives: improved grafting ratio and potential application in functional food

Antibacterial and Biofilm Modulating Potential of Ferulic Acid-Grafted Chitosan against Human Pathogenic Bacteria

Grafting of Gallic Acid onto Chitosan Enhances Antioxidant Activities and Alters Rheological Properties of the Copolymer

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