Mexia, N., Benohoud, M., Rayner, C.M. et al. (1 more author) (2023) Chemo- and regio-selective enzymatic lipophilisation of rutin, and physicochemical and antioxidant properties of rutin ester derivatives. RSC Advances, 13 (50). pp. 35216-35230. ISSN 2046-2069
Abstract
Enzymes are one of the most powerful tools in organic Green Chemistry and enzymatic reactions offer numerous advantages like regio- and enantio-selectivity along with their eco-friendly and sustainable nature. More specifically, lipases can catalyse both ester hydrolysis and formation depending on the nature of the substrate and water content. Herein, the focus is on the development of an enzymatically catalysed lipophilisation of natural compounds using lipases of microbial origin and the investigation of the optimal reaction conditions, aiming ultimately to ameliorate the compounds' properties. The flavonoid disaccharide rutin (quercetin-3-O-rutinoside) was the model compound on which the acylation protocol was built, allowing an efficient procedure to be established, while simultaneously offering the possibility of developing rapid, clear and robust methodologies, using state-of-the-art techniques, for analysis and purification of the synthesized compounds. An optimal 72 h reaction at 55 °C, using Candida antarctica lipase B immobilized on acrylic resin, combined with silicon dioxide as dehydrating agent, followed by product purification, achieved conversion ratios up to 50%. Full characterization and evaluation of the physicochemical and antioxidant properties of the esterified compounds was obtained. The lipophilicity of the rutin esters produced increased with increasing alkyl chain length, yet antioxidant properties were unaffected in comparison with the parent compound. A preparatively useful acylation protocol was established, allowing full investigation into the properties of the acylated compounds. It is also applicable for use on mixtures of compounds as most natural products are found in nature in mixtures and such a development greatly enhances the potential of this method for future commercial applications.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2023 The Author(s). This is an open access article under the terms of the Creative Commons Attribution License (CC-BY 4.0), which permits unrestricted use, distribution and reproduction in any medium, provided the original work is properly cited. |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Arts, Humanities and Cultures (Leeds) > School of Design (Leeds) |
Funding Information: | Funder Grant number BBSRC (Biotechnology & Biological Sciences Research Council) PoC17_07 BBSRC (Biotechnology & Biological Sciences Research Council) BB/S005013/1 |
Depositing User: | Symplectic Publications |
Date Deposited: | 05 Dec 2023 15:43 |
Last Modified: | 05 Dec 2023 15:44 |
Status: | Published |
Publisher: | Royal Society of Chemistry |
Identification Number: | 10.1039/D3RA06333J |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:206175 |