Chemo- and regio-selective enzymatic lipophilisation of rutin, and physicochemical and antioxidant properties of rutin ester derivatives.

Autor:	Mexia N; Leeds Institute of Textiles and Colour, School of Design, University of Leeds Leeds LS2 9JT UK r.s.blackburn@leeds.ac.uk.; School of Chemistry, University of Leeds Leeds LS2 9JT UK., Benohoud M; Keracol Limited Nexus, Discovery Way Leeds LS2 3AA UK., Rayner CM; School of Chemistry, University of Leeds Leeds LS2 9JT UK.; Keracol Limited Nexus, Discovery Way Leeds LS2 3AA UK., Blackburn RS; Leeds Institute of Textiles and Colour, School of Design, University of Leeds Leeds LS2 9JT UK r.s.blackburn@leeds.ac.uk.; Keracol Limited Nexus, Discovery Way Leeds LS2 3AA UK.
Jazyk:	angličtina
Zdroj:	RSC advances [RSC Adv] 2023 Dec 04; Vol. 13 (50), pp. 35216-35230. Date of Electronic Publication: 2023 Dec 04 (Print Publication: 2023).
DOI:	10.1039/d3ra06333j
Abstrakt:	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. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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