Inspired by nature: Fiber networks functionalized with tannic acid and condensed tannin-rich extracts of Norway spruce bark show antimicrobial efficacy

Jyske, Tuula; Liimatainen, Jaana; Tienaho, Jenni; Brännström, Hanna; Aoki, Dan; Kuroda, Katsushi; Reshamwala, Dhanik; Kunnas, Susan; Halmemies, Eelis; Nakayama, Eiko; Kilpeläinen, Petri; Ora, Ari; Kaseva, Janne; Hellström, Jarkko; Marjomäki, Varpu; Karonen, Maarit; Fukushima, Kazuhiko

doi:10.3389/fbioe.2023.1171908

Cited by 9 publications

(9 citation statements)

References 50 publications

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“…Also, TA containing nanoparticles have been shown to induce antiviral activity ( Orłowski et al, 2018 ). Furthermore, in our previous study, TA also showed efficacy against CVB3 when it was bound to handsheets using a dip coating method without any additional binding polymers or chemicals ( Jyske et al, 2023 ). Although in that study, TA was not strongly bound to the surface and probably efficacy was based on easily leaching TA from the surface, TA showed its promise also against the stable enteroviruses.…”

Section: Discussionmentioning

confidence: 99%

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Antiviral functionalization of cellulose using tannic acid and tannin-rich extracts

Haapakoski,

Emelianov,

Reshamwala

et al. 2023

Front. Microbiol.

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Due to seasonally appearing viruses and several outbreaks and present pandemic, we are surrounded by viruses in our everyday life. In order to reduce viral transmission, functionalized surfaces that inactivate viruses are in large demand. Here the endeavor was to functionalize cellulose-based materials with tannic acid (TA) and tannin-rich extracts by using different binding polymers to prevent viral infectivity of both non-enveloped coxsackievirus B3 (CVB3) and enveloped human coronavirus OC43 (HCoV-OC43). Direct antiviral efficacy of TA and spruce bark extract in solution was measured: EC50 for CVB3 was 0.12 and 8.41 μg/ml and for HCoV-OC43, 78.16 and 95.49 μg/ml, respectively. TA also led to an excellent 5.8- to 7-log reduction of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) virus infectivity. TA functionalized materials reduced infectivity already after 5-min treatment at room temperature. All the tested methods to bind TA showed efficacy on paperboard with 0.1 to 1% (w/v) TA concentrations against CVB3 whereas material hydrophobicity decreased activities. Specific signatures for TA and HCoV-OC43 were discovered by Raman spectroscopy and showed clear co-localization on the material. qPCR study suggested efficient binding of CVB3 to the TA functionalized cellulose whereas HCoV-OC43 was flushed out from the surfaces more readily. In conclusion, the produced TA-materials showed efficient and broadly acting antiviral efficacy. Additionally, the co-localization of TA and HCoV-OC43 and strong binding of CVB3 to the functionalized cellulose demonstrates an interaction with the surfaces. The produced antiviral surfaces thus show promise for future use to increase biosafety and biosecurity by reducing pathogen persistence.

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Section: Discussionmentioning

confidence: 99%

“…Industrial Norway spruce [ P. abies (L.) Karst.] bark from a sawmill was retrieved and extracted as described previously ( Jyske et al, 2023 ). Willow (Salix spp.)…”

Section: Methodsmentioning

confidence: 99%

Antiviral functionalization of cellulose using tannic acid and tannin-rich extracts

Haapakoski,

Emelianov,

Reshamwala

et al. 2023

Front. Microbiol.

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“…19 Spruce tannin, supplied by LUKE (Helsinki, Finland), was obtained by hot water extraction of spruce bark followed by purification using the XAD7HP adsorbent. 28,29 The spruce tannin was referred to as crude tannin. Comprehensive information regarding the manufacturing, purification, and fractionation processes of lignin and tannin is available in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Laccase-Catalyzed Copolymerization of Tannin and Technical Lignin: Polymerization Kinetics and Enhanced Properties of Polyphenols

Lu,

Tienaho,

Kilpeläinen

et al. 2024

ACS Sustainable Chem. Eng.

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Polymerization of lignin has garnered significant interest due to its potential to unlock innovative and value-added applications for lignin to replace petroleum-based phenolic synthetics in future polymeric materials. However, conventional strategies for lignin polymerization often adopt complex cross-linking reactions with large amounts of unsustainable chemicals, which may impose environmental and ecological concerns. Herein, a green method for polyphenol polymerization is developed, in which tannin-rich extracts serve as building blocks to facilitate lignin polymerization under laccase-catalyzed oxidation. The molar mass and chemical structure of polymerized lignin, tannin, and their mixture and polymerization kinetics are comprehensively studied. Results show that the incorporation of tannin can increase the polymerization degree and rate of lignin and preserve more phenolic–OH groups after laccase incubation compared with self-polymerized lignin or tannin. Moreover, the possible polymerization mechanisms for lignin and tannin samples are proposed based on NMR and FTIR spectrum analysis. The polymerized lignin–tannin samples have superior or similar physicochemical properties compared to self-polymerized lignin or tannin in terms of UV shielding, thermal stability, and antimicrobial properties. Overall, this study offers novel insights into the copolymerization of lignin and tannin catalyzed by laccase and underpins further applications of upgraded polyphenols as polymers.

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“…The authors also reported that their coatings must be developed to ensure a long-term antibacterial effect since the noncovalent bonds were the driving force between TA and the handsheet substrate. 30 As a result, the durability of zwitterionic polymer-based coating is a challenge during large-scale application, even when the polymer was covalently linked to TA. 31 In this work, we report a simple one-pot dip-coating process for depositing TA and zwitterionic copolymers containing amine groups under oxidizing conditions to form covalent conjugation between the quinone and amino groups via the Michael addition reaction.…”

Section: Introductionmentioning

confidence: 99%

“…coli, and Enterovirus coxsackievirus. The authors also reported that their coatings must be developed to ensure a long-term antibacterial effect since the noncovalent bonds were the driving force between TA and the handsheet substrate . As a result, the durability of zwitterionic polymer-based coating is a challenge during large-scale application, even when the polymer was covalently linked to TA …”

Section: Introductionmentioning

confidence: 99%

Tannic Acid-Based Coatings Containing Zwitterionic Copolymers for Improved Antifouling and Antibacterial Properties

Imbia,

Ounkaew,

Mao

et al. 2024

Langmuir

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The prevention of biofilm formation on medical devices has become highly challenging in recent years due to its resistance to bactericidal agents and antibiotics, ultimately resulting in chronic infections to medical devices. Therefore, developing inexpensive, biocompatible, and covalently bonded coatings to combat biofilm formation is in high demand. Herein, we report a coating fabricated from tannic acid (TA) as an adhesive and a reducing agent to graft the zwitterionic polymer covalently in a one-step method. Subsequently, silver nanoparticles (AgNPs) are generated in situ to develop a coating with antifouling and antibacterial properties. To enhance the antifouling property and biocompatibility of the coating, the bioinspired zwitterionic 2methacryloyloxyethyl phosphorylcholine (MPC) was copolymerized with 2-aminoethyl methacrylamide hydrochloride (AEMA) using conventional free-radical polymerization. AEMA moieties containing amino groups were used to facilitate the conjugation of the copolymer with quinone groups on TA through the Michael addition reaction. Three copolymers with different ratios of monomers were synthesized to understand their impacts on fouling resistance: PMPC 100 , p(MPC 80 -st-AEMA 20 ), and p(MPC 90 -st-AEMA 10 ). To impart antibacterial properties to the surface, AgNPs were formed in situ, utilizing the unreacted quinone groups on TA, which can reduce the silver ions. The successful coating of TA and copolymer onto the surfaces was confirmed by attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectroscopy, and its excellent wettability was verified by the water contact angle (CA). Furthermore, the functionalized coatings showed antibacterial properties against E. coli and S. aureus and remarkably decreased the adhesion of the BSA protein. The surfaces can also prevent the adhesion of bacteria cells, as confirmed by the inhibition zone test. In addition, they showed negligible cytotoxicity to normal human lung fibroblast cells (MRC-5). The as-prepared coatings are potentially valuable for biomedical applications.

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Inspired by nature: Fiber networks functionalized with tannic acid and condensed tannin-rich extracts of Norway spruce bark show antimicrobial efficacy

Cited by 9 publications

References 50 publications

Antiviral functionalization of cellulose using tannic acid and tannin-rich extracts

Antiviral functionalization of cellulose using tannic acid and tannin-rich extracts

Laccase-Catalyzed Copolymerization of Tannin and Technical Lignin: Polymerization Kinetics and Enhanced Properties of Polyphenols

Tannic Acid-Based Coatings Containing Zwitterionic Copolymers for Improved Antifouling and Antibacterial Properties

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