Thermally Stable and Antimicrobial Active Poly(Catechin) Obtained by Reaction with a Cross-Linking Agent

Latos‐Brozio, Malgorzata; Masek, Anna; Piotrowska, Małgorzata

doi:10.3390/biom11010050

Cited by 18 publications

(38 citation statements)

References 33 publications

(43 reference statements)

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“…Ball-shaped structures (marked with red circles on Figure 4) could be characterized for the GDE agent. Similar observations were found for polymeric forms of (+)-catechin obtained by crosslinking with GDE [28]. However, the specificity of crosslinking of flavonoids may depend on the electron density and the presence of groups having an electron donation effect.…”

Section: Resultssupporting

confidence: 80%

“…where A 0 is the absorbance of the reference sample without naringenin and poly(naringenin), and A 1 is the absorbance in the presence of naringenin or the polymeric form of naringenin [28]. Absorbance was measured at 734 nm for the ABTS method and at 517 nm for the DPPH test using a UV spectrophotometer (Evolution 220, Thermo Fisher Scientific, Waltham, MA, USA).…”

Section: Inhibition Of Free Radicals (%) = [((A 0 −mentioning

confidence: 99%

“…where: A 0 is the absorbance of the reagent sample, A AR is the absorbance after reaction [28]. The absorbance was measured at 595 nm for the FRAP assay and at 450 nm for the CUPRAC determination using a UV spectrophotometer.…”

Section: Inhibition Of Free Radicals (%) = [((A 0 −mentioning

confidence: 99%

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Novel Polymeric Biomaterial Based on Naringenin

2021

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Biomaterials prepared based on raw plant materials are becoming more and more popular due to their specific properties and environmental friendliness. Naringenin is a flavonoid naturally occurring in citrus fruit with antioxidant and pharmacological activity. Polymeric materials based on flavonoids may have favorable properties in comparison to monomeric polyphenols, such as stronger antioxidant and antimicrobial properties. One of the methods of obtaining the polymeric form of flavonoids is polymerization with a cross-linking compound. This method has already been used to obtain poly(quercetin) and poly(rutin) from a flavonol group as well as poly(catechin) from the flavan-3-ol group of flavonoids. However, to date, no polymeric forms of flavanones have been prepared in a cross-linking reaction; the aim of this study was to obtain poly(naringenin) by reaction with a cross-linking compound using glycerol diglycide ether GDE. The degree of conversion of naringenin to poly(naringenin) determined by FTIR spectroscopy was 85%. In addition, the thermal, antioxidant and antimicrobial properties of poly(naringenin) were analyzed. Poly(naringenin) was characterized by greater resistance to oxidation and better thermal stability than monomeric naringenin. Moreover, polymeric naringenin also had a better ability to scavenge ABTS and DPPH free-radicals. In contrast to monomeric form, poly(naringenin) had antimicrobial activity against Candida albicans. Polymeric biomaterial based on naringenin could potentially be used as a natural stabilizer and antimicrobial additive for polymer compositions, as well as pro-ecological materials.

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Section: Resultssupporting

confidence: 80%

Section: Inhibition Of Free Radicals (%) = [((A 0 −mentioning

confidence: 99%

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Novel Polymeric Biomaterial Based on Naringenin

2021

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“…As reported previously, polymeric compounds of catechin can be obtained by various reaction pathways, such as enzymatic polymerization [92][93][94], photopolymerization [11,86], HCl-catalyzed polymerization [95], polycondensation with aldehydes in the presence of acid catalysts [96][97][98], and cross-linking reactions of catechin with glycerol diglycidyl ether [99]. A study also reported that the complex condensed aromatic compounds of natural tannins result in high thermal resistance [100].…”

Section: Application Of Catechin Photolysismentioning

confidence: 84%

“…Latos-Brozio and Masek reported that a polymeric catechin complex is generated when catechin is placed in a phosphate-buffered solution, subjected to BLI, and dried at 55 • C. This process produces (+)-catechin photo-polymerization, and the polymeric catechin complex exhibits better thermal stability and a better ability to reduce transition metal ions compared with catechin [86,99]. A polymeric complex of catechin can potentially be used as a pro-ecological stabilizing agent, in addition to being applied as a functional additive for polymeric materials, and as a dressing material in medicine [86,99].…”

Section: Application Of Catechin Photolysismentioning

confidence: 99%

A Study of Catechin Photostability Using Photolytic Processing

et al. 2021

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Catechin exhibits numerous physiological characteristics. In this study, we determined the photosensitivity of catechin to various lights under alkaline conditions, and the mechanisms by which catechin generates free radical species and polymerizes via a photoreaction. In addition to this, the application of catechin photolysis was investigated. A solution of catechin is transparent, but turns yellowish under blue light illumination (BLI) in neutral or weak alkaline solutions. When catechin is subjected to BLI, a dimeric catechin (proanthocyanidin) and a superoxide anion radical (O2•−) are generated in a photolytic reaction. When ascorbic acid or gallic acid is added to catechin and the mixture is subjected to BLI at alkaline pH, fewer catechin dimers and less O2•− are produced, because both acids inhibit the photosensitive oxidation of catechin. When AlCl3 is added to catechin and the mixture is subjected to BLI at pH 8, a photolytic reaction is suppressed by AlCl3, and AlCl3 acts as a catalyst for the disconnection of proanthocyanidin during photolysis. Under alkaline conditions, catechin generates O2•− via photosensitive oxidation, which suppresses the growth of Acinetobacter baumannii (A. baumannii) by at least 4 logs, and deactivates its multi-drug-resistant strain. This study shows that catechin photolysis is a process of oxidation, and that it can be safely applied as a tool for environmental applications.

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Effect of enzymatic polymerization on the thermal stability of flavonoids

Latos‐Brozio

Masek

Piotrowska

2023

J Therm Anal Calorim

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The mechanisms of the enzymatic polymerization of flavonoids, including quercetin, rutin and catechins, have been fairly well researched, but the properties of polymeric forms of flavonoids still require in-depth analysis. The products of enzymatic polymerization are oligomeric flavonoids. The antioxidant and antimicrobial properties of many oligomeric flavonoids have been described in the literature. However, data on the thermal properties of oligomeric flavonoids are lacking and the supplementing of these deficiencies is a scientific novelty of this work. The aim of this study is to determine the effect of enzymatic polymerization on thermal stability of oligomeric flavonoids. As part of the work, oligomeric quercetin, rutin and catechin were prepared by the enzymatic polymerization reaction with laccase and horseradish peroxidase enzymes. The oligomeric structure of the flavonoids was confirmed by spectroscopic (Fourier transform infrared spectroscopy (FTIR) and UV–visible spectroscopy (UV–Vis)) as well as chromatographic (ultra-performance liquid chromatography (UPLC) and gel permeation chromatography (GPC)) methods. Thermal properties of oligomeric flavonoids were investigated using differential scanning calorimetry (DSC) and thermogravimetry (TG). Moreover, the antioxidant and antimicrobial properties of oligomeric forms of selected polyphenols were investigated. Based on DSC analysis, it was found that the common feature of all oligomeric flavonoids was a higher final oxidation temperature and a higher oxidation enthalpy than the reference flavonoids. Thermogravimetric analysis showed that oligomeric poly(flavonoids)-laccase had better thermal stability, which correlated with higher molar mass.

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Thermally Stable and Antimicrobial Active Poly(Catechin) Obtained by Reaction with a Cross-Linking Agent

Cited by 18 publications

References 33 publications

Novel Polymeric Biomaterial Based on Naringenin

Novel Polymeric Biomaterial Based on Naringenin

A Study of Catechin Photostability Using Photolytic Processing

Effect of enzymatic polymerization on the thermal stability of flavonoids

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