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Antioxidants
Special Issues
Phenolic Polymers and Redox-Active Films
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Phenolic Polymers and Redox-Active Films

A special issue of Antioxidants (ISSN 2076-3921).

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 7954

Special Issue Editors

Dr. Maria Laura Alfieri

E-Mail Website
Guest Editor
Department of Chemical Sciences, University of Naples “Federico II”, Via Cintia 4, I-80126 Naples, Italy
Interests: polyphenols; antioxidants; melanins; bioinspired phenolic polymers; biocompatible materials; polydopamine; coatings
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Vincent Ball

E-Mail Website
Guest Editor
1. Faculté de Chirurgie Dentaire, Université de Strasbourg, Strasbourg, France
2. Institut National de la Santé et de la Recherche Médicale, Unité mixte de rechere 1121, CEDEX, Strasbourg, France
Interests: polydopamine coatings; electrodeposition; surface characterization
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Phenolic compounds are widespread in nature and are attracting growing interest in view of their diverse biological roles, e.g., as physiological mediators and messenger molecules in the nervous system (dopamine and other catecholamines); structural components (e.g., lignins); photoprotective pigments (e.g., melanins); and reactive components in adhesive organisms (e.g., dopa residues in mussel byssus proteins), and their potential applications, e.g., as antioxidants and free radical scavengers (plant polyphenols). Catechol systems, especially, are the focus of intensive research because of their peculiar redox reactivity. Upon conversion to semiquinone and o-quinone derivatives, catechols can turn into free radical intermediates and highly electrophilic species, respectively, becoming available for efficient coupling processes and nucleophilic attack, allowing for efficient crosslinking reactions and coupling even under mild biologically relevant conditions, oxidative polymerization, strong metal chelating properties and the ability to interact with a variety of functional groups and surfaces.

We invite you to submit your latest research findings or a review article to this Special Issue, which will gather current research concerning the elucidation of the structure–property–function relationships of catechols, with particular attention paid to redox-based properties (e.g., antioxidant, pro-oxidant, and radical scavenging activities). This research can also include characterization methods available to probe the redox properties of catechol-functionalized materials.

We look forward to your contribution.

Dr. Maria Laura Alfieri
Prof. Dr. Vincent Ball
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Antioxidants is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • catechols
  • polyphenols
  • antioxidants
  • redox-active films

Published Papers (5 papers)

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Research

18 pages, 3590 KiB  
Article
A High-Performance Food Package Material Prepared by the Synergistic Crosslinking of Gelatin with Polyphenol–Titanium Complexes
by Wanqin Zhang, Jiaman Liu, Tao Zhang and Bo Teng
Antioxidants 2024, 13(2), 167; https://doi.org/10.3390/antiox13020167 - 29 Jan 2024
Cited by 2 | Viewed by 848
Abstract
This study aims to enhance gelatin film performance in the food industry by incorporating polyphenol–titanium complexes (PTCs) as crosslinkers. PTCs introduce multiple linkages with gelatin, including coordination and hydrogen bonds, resulting in synergistic crosslinking effects. This leads to an increased hydrodynamic volume, particle [...] Read more.
This study aims to enhance gelatin film performance in the food industry by incorporating polyphenol–titanium complexes (PTCs) as crosslinkers. PTCs introduce multiple linkages with gelatin, including coordination and hydrogen bonds, resulting in synergistic crosslinking effects. This leads to an increased hydrodynamic volume, particle size, and thermal stability of the gelatin films. Compared to films crosslinked solely by polyphenols or titanium, PTC-crosslinked gelatin films exhibit significant improvements. They show enhanced mechanical properties with a tensile strength that is 1.7 to 2.6 times higher than neat gelatin films. Moreover, these films effectively shield UV light (from 82% to 99%), providing better protection for light-sensitive food ingredients and preserving lutein content (from 74.2% to 78.1%) under light exposure. The incorporation of PTCs also improves film hydrophobicity, as indicated by water contact angles ranging from 115.3° to 131.9° and a water solubility ranging from 31.5% to 33.6%. Additionally, PTC-enhanced films demonstrate a superior antioxidant ability, with a prolonged polyphenol release (up to 18 days in immersed water) and a higher free radical scavenging ability (from 22% to 25.2%). Overall, the improved characteristics of gelatin films enabled by PTCs enhance their performance, making them suitable for various food packaging applications. Full article
(This article belongs to the Special Issue Phenolic Polymers and Redox-Active Films)
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15 pages, 2381 KiB  
Article
Enhancement of the Physical and Functional Properties of Chitosan Films by Incorporating Galla chinensis Extract
by Ran Tao, Xiuxia Zheng, Bei Fan, Xuemei He, Jian Sun, Yufeng Sun and Fengzhong Wang
Antioxidants 2024, 13(1), 69; https://doi.org/10.3390/antiox13010069 - 2 Jan 2024
Viewed by 965
Abstract
Composite films based on chitosan (CS) incorporating Galla chinensis extract (GCNE) at different CS/GCNE weight ratios, which are both biodegradable and multifunctional, were fabricated using the solution-casting method. The FTIR analyses indicated that a good interaction was presented among the GCNE and CS [...] Read more.
Composite films based on chitosan (CS) incorporating Galla chinensis extract (GCNE) at different CS/GCNE weight ratios, which are both biodegradable and multifunctional, were fabricated using the solution-casting method. The FTIR analyses indicated that a good interaction was presented among the GCNE and CS through an intermolecular hydrogen bond. The incorporation of the GCNE improved the films’ elongation at break, UV-light blocking, and decreased the moisture regain (from 16.68% to 10.69%) and water absorption (from 80.65% to 54.74%). Moreover, the CS/GCNE films exhibited a strong antioxidant activity (from 57.11% to 70.37% of DPPH and from 35.53% to 46.73% of ABTS scavenging activities) mainly due to the high content of phenolic compounds in the incorporated GCNE. The CS/GCNE film-forming solution coatings demonstrated their effectiveness in preserving the quality of postharvest mangoes, specifically by minimizing the change in the firmness, weight loss, titratable acidity, and total phenolic and ascorbic acids. These findings suggest that the multifunctional composite films possess a high application potential to preserve postharvest fruits. Full article
(This article belongs to the Special Issue Phenolic Polymers and Redox-Active Films)
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12 pages, 4304 KiB  
Article
Strongly Metal-Adhesive and Self-Healing Gelatin@Polydopamine-Based Hydrogels with Long-Term Antioxidant Activity
by Jordana Hirtzel, Guillaume Leks, Julie Favre, Benoît Frisch, Isabelle Talon and Vincent Ball
Antioxidants 2023, 12(9), 1764; https://doi.org/10.3390/antiox12091764 - 14 Sep 2023
Viewed by 1225
Abstract
Bioinspired adhesives have been increasingly developed, especially towards a biomedical application. Therefore, in this study, dopamine (DA) was oxidized into polydopamine (PDA) in a gelatin mixture via titration with NaIO4 as a strong oxidant to easily obtain an adhesive antioxidant and self-healing [...] Read more.
Bioinspired adhesives have been increasingly developed, especially towards a biomedical application. Therefore, in this study, dopamine (DA) was oxidized into polydopamine (PDA) in a gelatin mixture via titration with NaIO4 as a strong oxidant to easily obtain an adhesive antioxidant and self-healing PDA–gelatin hydrogel. Rheology experiments show a stiffness in the order of kPa and a thermal resistance above 50 °C, much above the gel–sol transition temperature of pristine gelatin. After heating at 55 °C, the gel is self-healing. In addition, just after formulation, it shows strong peeling-rate-dependent adhesion to steel with a tensile work per unit area (W) of up to 100 ± 39 J/m2, which is 2.5 times higher than that of the same gel without PDA at a peeling rate of 1000 µm/s. The increase in W between peeling rates of 10 and 1000 µm/s was studied and interpreted in terms of the gels’ viscoelasticity. Moreover, this hydrogel offers significant antioxidant activity (measured by DPPH scavenging) that lasts with storage for at least over 15 days, this being then prolonged for 2 additional days, which seems particularly relevant considering the importance of reactive oxygen species (ROS) in wound healing. To summarize, PDA–gelatin gel is a promising strong and antioxidant adhesive. Full article
(This article belongs to the Special Issue Phenolic Polymers and Redox-Active Films)
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18 pages, 2962 KiB  
Article
Potent Antioxidant and Anti-Tyrosinase Activity of Butein and Homobutein Probed by Molecular Kinetic and Mechanistic Studies
by Wenkai Pan, Ilaria Giovanardi, Tomiris Sagynova, Alice Cariola, Veronica Bresciani, Matteo Masetti and Luca Valgimigli
Antioxidants 2023, 12(9), 1763; https://doi.org/10.3390/antiox12091763 - 14 Sep 2023
Cited by 1 | Viewed by 1555
Abstract
Butein (BU) and homobutein (HB) are bioactive polyhydroxylated chalcones widespread in dietary plants, whose antioxidant properties require mechanistic definition. They were investigated by inhibited autoxidation kinetic studies of methyl linoleate in Triton™ X-100 micelles at pH 7.4, 37 °C. Butein had kinh [...] Read more.
Butein (BU) and homobutein (HB) are bioactive polyhydroxylated chalcones widespread in dietary plants, whose antioxidant properties require mechanistic definition. They were investigated by inhibited autoxidation kinetic studies of methyl linoleate in Triton™ X-100 micelles at pH 7.4, 37 °C. Butein had kinh = (3.0 ± 0.9) × 104 M−1s−1 showing a chain-breaking mechanism with higher antioxidant activity than reference α-tocopherol (kinh = (2.2 ± 0.6) × 104 M−1s−1), particularly concerning the stoichiometry or peroxyl radical trapping n = 3.7 ± 1.1 vs. 2.0 for tocopherol. Homobutein had kinh = (2.8 ± 0.9) × 103 M−1s−1, pairing the relative BDEOH measured by radical equilibration EPR as 78.4 ± 0.2 kcal/mol for BU and estimated as 82.6 kcal/mol for HB. The inhibition of mushroom tyrosinase (mTYR) by HB and BU was also investigated. BU gives a reversible uncompetitive inhibition of monophenolase reaction with KI′ = 9.95 ± 2.69 µM and mixed-type diphenolase inhibition with KI = 3.30 ± 0.75 µM and KI′ = 18.75 ± 5.15 µM, while HB was nearly competitive toward both mono- and diphenolase with respective KI of 2.76 ± 0.70 µM and 2.50 ± 1.56 µM. IC50 values (monophenolase/diphenolase at 1 mM substrate) were 10.88 ± 2.19 µM/15.20 ± 1.25 µM, 14.78 ± 1.05 µM/12.36 ± 2.00 µM, and 33.14 ± 5.03 µM/18.27 ± 3.42 µM, respectively, for BU, HB, and reference kojic acid. Molecular docking studies confirmed the mechanism. Results indicate very potent antioxidant activity for BU and potent anti-tyrosinase activity for both chalcones, which is discussed in relation to bioactivity toward protection from skin disorders and food oxidative spoilage. Full article
(This article belongs to the Special Issue Phenolic Polymers and Redox-Active Films)
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13 pages, 2023 KiB  
Article
Insight into the Antioxidant Activity of 1,8-Dihydroxynaphthalene Allomelanin Nanoparticles
by Alexandra Mavridi-Printezi, Fabio Mollica, Rosa Lucernati, Marco Montalti and Riccardo Amorati
Antioxidants 2023, 12(8), 1511; https://doi.org/10.3390/antiox12081511 - 28 Jul 2023
Viewed by 2878
Abstract
Melanins are stable and non-toxic pigments with great potential as chemopreventive agents against oxidative stress for medical and cosmetic applications. Allomelanin is a class of nitrogen-free melanin often found in fungi. The artificial allomelanin obtained by the polymerization of 1,8-dihydroxynaphthalene (DHN), poly-DHN (PDHN), [...] Read more.
Melanins are stable and non-toxic pigments with great potential as chemopreventive agents against oxidative stress for medical and cosmetic applications. Allomelanin is a class of nitrogen-free melanin often found in fungi. The artificial allomelanin obtained by the polymerization of 1,8-dihydroxynaphthalene (DHN), poly-DHN (PDHN), has been recently indicated as a better radical quencher than polydopamine (PDA), a melanin model obtained by the polymerization of dopamine (DA); however, the chemical mechanisms underlying this difference are unclear. Here we investigate, by experimental and theoretical methods, the ability of PDHN nanoparticles (PDHN-NP), in comparison to PDA-NP, to trap alkylperoxyl (ROO•) and hydroperoxyl (HOO•) radicals that are involved in the propagation of peroxidation in real conditions. Our results demonstrate that PDHN-NP present a higher antioxidant efficiency with respect to PDA-NP against ROO• in water at pH 7.4 and against mixed ROO• and HOO• in acetonitrile, showing catalytic cross-termination activity. The antioxidant capacity of PDHN-NP in water is 0.8 mmol/g (ROO• radicals quenched by 1 g of PDHN-NP), with a rate constant of 3 × 105 M−1 s−1 for each reactive moiety. Quantum-mechanical calculations revealed that, thanks to the formation of a H-bond network, the quinones in PDHN-NP have a high affinity for H-atoms, thus justifying the high reactivity of PDHN-NP with HOO• observed experimentally. Full article
(This article belongs to the Special Issue Phenolic Polymers and Redox-Active Films)
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