Laccase-mediated functionalization of chitosan by caffeic and gallic acids for modulating antioxidant and antimicrobial properties

Božič, Mojca; Gorgieva, Selestina; Kokol, Vanja

doi:10.1016/j.carbpol.2011.11.006

Cited by 238 publications

(87 citation statements)

References 28 publications

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“…Different synthetic approaches have been reported for grafting phenolic acids with chitosan, such as 1-ethyl-3-(3′-dimethylaminopropyl) carbodiimide (EDC) and N-hydroxysuccinimide (NHS) reaction (Pasanphan et al 2010;Yu et al 2011), laccase catalyzed polymerization (Božič et al 2012), and free radical mediated grafting (Curcio et al 2009). However in laccase catalyzed polymerization, phenolic acids are oxidized into o-quinones which further react with the primary amines of chitosan.…”

Section: Resultsmentioning

confidence: 99%

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: 99%

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

et al. 2015

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“…One of the fields in which enzymes are increasingly capturing the interest of researchers across the globe is material science. There are several interesting examples describing the functionalization of natural fibers using enzymes in order to increase antibacterial properties [12], antioxidant capacity [12][13][14], or to increase compatibility with synthetic materials [15]. Nevertheless, it is still a challenge to find suitable enzymes for the biotransformation of non-natural and polymeric substrates.…”

Section: Introductionmentioning

confidence: 99%

A New Esterase from Thermobifida halotolerans Hydrolyses Polyethylene Terephthalate (PET) and Polylactic Acid (PLA)

et al. 2012

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Abstract:A new esterase from Thermobifida halotolerans (Thh_Est) was cloned and expressed in E. coli and investigated for surface hydrolysis of polylactic acid (PLA) and polyethylene terephthalate (PET). Thh_Est is a member of the serine hydrolases superfamily containing the -GxSxG-motif with 85-87% homology to an esterase from T. alba, to an acetylxylan esterase from T. fusca and to various Thermobifida cutinases. Thh_Est hydrolyzed the PET model substrate bis(benzoyloxyethyl)terephthalate and PET releasing terephthalic acid and mono-(2-hydroxyethyl) terephthalate in comparable amounts (19.8 and 21.5 mmol/mol of enzyme) while no higher oligomers like bis-(2-hydroxyethyl) terephthalate were detected. Similarly, PLA was hydrolyzed as indicated by the release of lactic acid. Enzymatic surface hydrolysis of PET and PLA led to a strong hydrophilicity increase, as quantified with a WCA decrease from 90.8° and 75.5° to 50.4° and to a complete spread of the water drop on the surface, respectively. OPEN ACCESSPolymers 2012, 4 618

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“…Aljawish et al used Myceliophthora thermophila laccase to catalyze the graing of ferulic acid or ethyl ferulate onto CS, affording materials with improved antioxidant and antibacterial properties. 6,7 Božič et al 8 also reported that laccase from Trametes versicolor can catalyze the graing of caffeic and gallic acids onto CS. Qiu et al 9 have reported the laccase catalyzed the graing of tea catechins onto CS using laccase to prepare a novel nanoltration membrane (obtained from SigmaAldrich, fungus source).…”

Section: 4mentioning

confidence: 99%

Preparation of ferulic acid-grafted chitosan using recombinant bacterial laccase and its application in mango preservation

Yang

Sun

et al. 2018

RSC Adv.

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To improve the antioxidant and antibacterial properties of chitosan, recombinant bacterial laccase from Bacillus vallismortis fmb-103 (fmb-rL103) was used to catalyze ferulic acid grafting. The grafted chitosan was characterized using UV-vis and FT-IR techniques. DPPH free radical scavenging results indicated that the antioxidant properties of the grafted chitosan (FA-g-CS) were significantly improved. Meanwhile, the antibacterial properties against E. coli, S. aureus, B. subtilis, and M. guilliermondii were also improved.Furthermore, FA-g-CS was applied to mango preservation as a coating, which improved the sensory qualities of mango Mangifera indica L. The disease incidence of mangoes coated with FA-grafted medium and high molecular weight chitosan were 0 and 5%, respectively. The respiratory peak was delayed more than 4 days, and the titratable acidity and ascorbic acid concentration were all enhanced.POD and CAT activities in FA-g-CS coated mangoes were higher than those coated with chitosan samples with a lower H 2 O 2 concentration.

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Laccase-mediated functionalization of chitosan by caffeic and gallic acids for modulating antioxidant and antimicrobial properties

Cited by 238 publications

References 28 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

A New Esterase from Thermobifida halotolerans Hydrolyses Polyethylene Terephthalate (PET) and Polylactic Acid (PLA)

Preparation of ferulic acid-grafted chitosan using recombinant bacterial laccase and its application in mango preservation

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