Enzymatic polymerization of plant-derived phenols for material-independent and multifunctional coating

Jeon, Jong-Rok; Kim, Jaehwan; Chang, Yoon Seok

doi:10.1039/c3tb21161d

Cited by 64 publications

(67 citation statements)

References 29 publications

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“…Catechol and catechin were chosen as substrates for enzymatic polymerization because of the individual substrates' high affinity for iron (i.e., catechol log β Fe(III) = 43.76, catechin log β Fe(III) = 47.4) 49 and their reported high coating deposition efficiency. 29 The catechol/catechin polymers generated in reaction solution by laccase were relatively large with an average molecular weight of 7.88 × 10 3 Da and a polydispersity index of 1.93. Polymer molecular weight was on the order of magnitude (10 3 Da) reported for polymers produced by laccase assisted oxidative polymerization of catechin.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Retaining Oxidative Stability of Emulsified Foods by Novel Nonmigratory Polyphenol Coated Active Packaging

Roman

Decker

Goddard

2016

J. Agric. Food Chem.

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Oxidation causes lipid rancidity, discoloration, and nutrient degradation that decrease shelf life of packaged foods. Synthetic additives are effective oxidation inhibitors, but are undesirable to consumers who prefer "clean" label products. The aim of this study was to improve oxidative stability of emulsified foods by a novel nonmigratory polyphenol coated active packaging. Polyphenol coatings were applied to chitosan functionalized polypropylene (PP) by laccase assisted polymerization of catechol and catechin. Polyphenol coated PP exhibited both metal chelating (39.3 ± 2.5 nmol Fe(3+) cm(-2), pH 4.0) and radical scavenging (up to 52.9 ± 1.8 nmol Trolox eq cm(-2)) capacity, resulting in dual antioxidant functionality to inhibit lipid oxidation and lycopene degradation in emulsions. Nonmigratory polyphenol coated PP inhibited ferric iron promoted degradation better than soluble chelators, potentially by partitioning iron from the emulsion droplet interface. This work demonstrates that polyphenol coatings can be designed for advanced material chemistry solutions in active food packaging.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Retaining Oxidative Stability of Emulsified Foods by Novel Nonmigratory Polyphenol Coated Active Packaging

Roman

Decker

Goddard

2016

J. Agric. Food Chem.

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“…14 TA can be deposited onto various organic and inorganic substrates because of its inherent affinity towards surfaces. 4,[15][16][17] TA is generally recognized as safe and non-toxic to consume in small amounts by the US Food and Drug Administration. 15 The commercial extraction of TA from plant part, such as Tara pods (Caesalpinia spinosa), gallnuts from Rhus semialata or Quercus infectoria, and Sicilian Sumac leaves (Rhus coriaria), is abundant and relatively cheap.…”

Section: Introductionmentioning

confidence: 99%

“…Since the trihydroxyphenyl moieties can react with thiol-containing compounds via Michael addition,17,46 TA was also anchored onto the SS surfaces to compare the conjugation efficiency of TA and TAMA with thiol groups. The XPS core-level spectral area ratios were employed to determine the change in surface compositions during modification of the SS-TA and SS-TAMA surfaces with PFDSH.…”

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confidence: 99%

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

Pranantyo

Neoh

et al. 2016

ACS Sustainable Chem. Eng.

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Inspired by tea stains, a new surface anchor, maleimido-containing tannic acid (TAMA), was developed to introduce the maleimido functionality onto the stainless steel (SS) surfaces. The feasibility of maleimido groups to serve as anchoring sites for surface functionalization via Michael addition was explored in a model experiment using thiol-containing 1H,1H,2H,2H-perfluorodecanethiol. The surface conjugation efficiency of TAMA with the thiol-containing compounds via Michael addition was also compared to that of the surface with tannic acid (TA) only. Water-soluble thiolated carboxymethyl chitosan (CMCSSH) was then grafted on the SS surface pre-anchored with TAMA via solution immersion and spin coating.The deposition of CMCSSH was characterized by contact angle measurement, surface zeta potential, and X-ray photoelectron spectroscopy (XPS). The antifouling efficacy of the CMCSSH coatings was evaluated by protein adsorption and bacterial adhesion. The cytotoxic effect of the CMCSSH coatings on mammalian cells was evaluated using the standard 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay with 3T3 fibroblasts.

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“…While previous reports have shown material‐independent adhesion of plant‐related polyphenolics onto different kinds of solid surfaces (Jeon et al ., ; Sileika et al ., ), with the structures of these polyphenolics containing adhesion‐promoting catechol groups, our results demonstrate that material‐independent adhesion could also be achieved with hydroxyphenyl groups. Our results may have been due to the synergistic effects of the polyaromaticity and multiple hydroxyphenyl groups of poly(2,7‐DHN): the hydrophobicity of the aromatic structures may have contributed to a decrease of solubility in water, hence promoting binding to surfaces, while the functional groups may have exerted adhesive forces similar to those of polycatechols.…”

Section: Resultsmentioning

confidence: 99%

“…The adhesive action, biocompatibility and hydrophilicity of such polymeric materials can be controlled by modifying the catechol structure and hence its physicochemical properties (Yamada et al ., ; Lee et al ., ; You et al ., ; Cho et al ., ). The catechol‐containing species can also be modified with polyphenolic moieties in order to affect its binding of diverse materials (McDonald et al ., ; Jeon et al ., , , ; Sileika et al ., ). This finding strongly supports the idea that the previously reported catechol‐based adhesives, including those whose adhesive action derives from polydopamine coating and catechol conjugation, could be reproduced by materials displaying polyphenolic moieties.…”

Section: Introductionmentioning

confidence: 99%

Dihydroxynaphthalene‐based mimicry of fungal melanogenesis for multifunctional coatings

Jeon

Chang

2016

Microbial Biotechnology

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SummaryMaterial‐independent adhesive action derived from polycatechol structures has been intensively studied due to its high applicability in surface engineering. Here, we for the first time demonstrate that a dihydroxynaphthalene‐based fungal melanin mimetic, which exhibit a catechol‐free structure, can act as a coating agent for material‐independent surface modifications on the nanoscale. This mimetic was made by using laccase to catalyse the oxidative polymerization of specifically 2,7‐dihydroxynaphthalene. Analyses of the product of this reaction, using Fourier transform infrared‐attenuated total reflectance and X‐ray photoelectron spectroscopy, bactericidal action, charge‐dependent sorption behaviour, phenol content, Zeta potential measurements and free radical scavenging activity, yielded results consistent with it containing hydroxyphenyl groups. Moreover, nuclear magnetic resonance analyses of the product revealed that C‐O coupling and C‐C coupling were the main mechanisms for its synthesis, thus clearly excluding a catechol structure in the polymerization. This product, termed poly(2,7‐DHN), was successfully deposited onto a wide variety of solid surfaces, including metals, polymeric materials, ceramics, biosurfaces and mineral complexes. The melanin‐like polymerization could be used to co‐immobilize other organic molecules, forming functional surfaces. In addition, the hydroxyphenyl group contained in the coated poly(2,7‐DHN) induced secondary metal chelation/reduction and adhesion with proteins, suggesting the potential of this poly(2,7‐DHN) layer to serve as a platform material for a variety of surface engineering applications. Moreover, the novel physicochemical properties of the poly(2,7‐DHN) illuminate its potential applications as bactericidal, radical‐scavenging and pollutant‐sorbing agents.

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Enzymatic polymerization of plant-derived phenols for material-independent and multifunctional coating

Cited by 64 publications

References 29 publications

Retaining Oxidative Stability of Emulsified Foods by Novel Nonmigratory Polyphenol Coated Active Packaging

Retaining Oxidative Stability of Emulsified Foods by Novel Nonmigratory Polyphenol Coated Active Packaging

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

Dihydroxynaphthalene‐based mimicry of fungal melanogenesis for multifunctional coatings

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