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Open AccessArticle

Chemical Structure–Antioxidant Activity Relationship of Water–Based Enzymatic Polymerized Rutin and Its Wound Healing Potential

1
Laboratory for Characterization and Processing of Polymers (LCPP), Faculty of Mechanical Engineering, University of Maribor, Smetanova 17, 2000 Maribor, Slovenia
2
Institute of Paper, Pulp and Fibre Technology (IPZ) Graz University of Technology, Inffeldgasse 23, 8010 Graz, Austria
3
Institute for Biomedical Sciences, Faculty of Medicine, University of Maribor, Taborska 8, 2000 Maribor, Slovenia
4
Department of Pharmacology, Faculty of Medicine, University of Maribor, Taborska 8, 2000 Maribor, Slovenia
5
Department of Polymer Chemistry and Technology, National Institute of Chemistry Slovenia, Hajdrihova 19, 1000 Ljubljana, Slovenia
6
Graz University of Technology, Stremayrgasse 9, 8010 Graz, Austria
*
Author to whom correspondence should be addressed.
Polymers 2019, 11(10), 1566; https://doi.org/10.3390/polym11101566
Received: 1 July 2019 / Revised: 16 September 2019 / Accepted: 25 September 2019 / Published: 26 September 2019
(This article belongs to the Special Issue Enzymatic Synthesis of Polymers)
The flavonoid rutin (RU) is a known antioxidant substance of plant origin. Its potential application in pharmaceutical and cosmetic fields is, however, limited, due to its low water solubility. This limitation can be overcome by polymerization of the phenolic RU into polyrutin (PR). In this work, an enzymatic polymerization of RU was performed in water, without the addition of organic solvents. Further, the chemical structure of PR was investigated using 1H NMR, and FTIR spectroscopy. Size-exclusion chromatography (SEC) was used to determine the molecular weight of PR, while its acid/base character was studied by potentiometric charge titrations. Additionally, this work investigated the antioxidant and free radical scavenging potential of PR with respect to its chemical structure, based on its ability to (i) scavenge non biological stable free radicals (ABTS), (ii) scavenge biologically important oxidants, such as O2•, NO•, and OH•, and (iii) chelate Fe2+. The influence of PR on fibroblast and HaCaT cell viability was evaluated to confirm the applicability of water soluble PR for wound healing application. View Full-Text
Keywords: rutin; polyrutin; aqueous enzymatic polymerization; chemical structure; antioxidant activity rutin; polyrutin; aqueous enzymatic polymerization; chemical structure; antioxidant activity
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MDPI and ACS Style

Pivec, T.; Kargl, R.; Maver, U.; Bračič, M.; Elschner, T.; Žagar, E.; Gradišnik, L.; Stana Kleinschek, K. Chemical Structure–Antioxidant Activity Relationship of Water–Based Enzymatic Polymerized Rutin and Its Wound Healing Potential. Polymers 2019, 11, 1566.

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