Abstract
The immobilization of Thermomyces lanuginosus lipase on polydopamine-functionalized Fe3O4 magnetic nanoparticles (Fe3O4@PDA-TLL) as a nanobiocatalyst was successfully performed for the first time, and the Fe3O4@PDA-TLL was used for regioselective acylation of natural hyperoside with vinyl decanoate. The effects of several crucial factors, such as the reaction solvent, substrate molar ratio, temperature, and immobilized enzyme dosage, were investigated. Under optimum conditions, the reaction rate, 6″-regioselectivity, and maximum substrate conversion were as high as 12.6 mM/h, 100%, and 100%, respectively. An operational stability study demonstrated that the immobilized enzyme could maintain 90.1% of its initial maximum conversion even after reusing it five times. In addition, further investigations on the kinetic parameters, like Vmax, Km, Vmax/Km, and Ea, also revealed that the biocompatible Fe3O4@PDA could act as an alternative carrier for the immobilization of different enzymes.
Highlights
Hyperoside, a type of flavonoid-O-glycoside, is the major pharmacological component of many traditional medicinal plants, such as Hyperin perforatum L., Geranium carolinianum L., Zanthoxylum bungeanum, Crataegus pinnatifida Bunge, and so forth (Pei et al, 2017)
Warnakulasuriya and Sudan have reported that quercetin-3-O-glucoside derivatives with long aliphatic chains could significantly reduce the primary hepatocytes’ injury and improve inhibition of hepatocellular carcinoma cells compared to quercetin-3-Oglucoside itself (Sudan and Rupasinghe, 2015; Warnakulasuriya and Rupasinghe, 2016)
As a result of this, in this study, for the first time, the immobilized Fe3O4@PDA-Thermomyces lanuginosus lipase (Fe3O4@PDA-TLL) was selected as the promising nanobiocatalyst to identify its kinetic behavior in nonaqueous enzymatic systems, in which the model reaction was the regioselective acylation of hyperoside with vinyl decanoate (Scheme 1)
Summary
Hyperoside ( known as quercetin-3-O-galactoside or 3-O-β-D-galactopyranosyl quercetin), a type of flavonoid-O-glycoside, is the major pharmacological component of many traditional medicinal plants, such as Hyperin perforatum L., Geranium carolinianum L., Zanthoxylum bungeanum, Crataegus pinnatifida Bunge, and so forth (Pei et al, 2017). Flavonoid glycoside and their analogs usually exhibit the physicochemical properties of unsatisfactory lipid solubility, poor stability, and low bioavailability, owing to their exiting active natural polyphenol-rich structures, which limits their applications in lipophilic systems (Newman and Cragg, 2016; Yang et al, 2018). Over the past few years, structural modifications by employing enzymatic methodology have clearly become an important topic in carbohydrate chemistry This has been described as the preferred method, possessing a short synthetic route, impressive selectivity, and environmental friendliness compared to the multistep chemical approaches (de Araújo et al, 2017; Dunbar et al, 2017). As a result of this, in this study, for the first time, the immobilized Fe3O4@PDA-Thermomyces lanuginosus lipase (Fe3O4@PDA-TLL) was selected as the promising nanobiocatalyst to identify its kinetic behavior in nonaqueous enzymatic systems, in which the model reaction was the regioselective acylation of hyperoside with vinyl decanoate (Scheme 1)
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