Microfluidic reactor for lipase-catalyzed regioselective synthesis of neohesperidin ester derivatives and their antimicrobial activity research

Du, Lingling; Jiang, Zhipeng; Xu, Liangliang; Zhou, Nani; Shen, Jia-Hong; Dong, Zhen Rong; Shen, Le; Wang, Hong; Luo, Xubiao

doi:10.1016/j.carres.2017.11.008

Cited by 21 publications

(9 citation statements)

References 32 publications

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“…In addition, MMC values were >400 µg/mL for all evaluated strains, thus indicating that the ester shows bacteriostatic and fungistatic action. These results could be due to its high hydrophobicity, thus improving its ability to interact with cell membranes and/or to penetrate through the cell membrane of these pathogens [58]. These results are in accordance with a previous study regarding the use of solketal-based esters as potential antimicrobial agents [5].…”

Section: In Vitro Antimicrobial Activity Studysupporting

confidence: 91%

Sustainable Enzymatic Synthesis of a Solketal Ester—Process Optimization and Evaluation of Its Antimicrobial Activity

et al. 2020

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The present study aims the enzymatic synthesis of solketal palmitate by esterification between solketal and palmitic acid using heptane as solvent. Lipases from Thermomyces lanuginosus (TLL), Candida rugosa type VII (CRL), and Pseudomonas fluorescens (PFL) were immobilized via interfacial activation on rice husk silica functionalized with triethoxy(octyl)silane (Octyl–SiO2) and used as biocatalysts. A loading of 20–22 mg of lipase/g of support was immobilized independently of the studied enzyme. TLL–Octyl–SiO2 was the most active biocatalyst in oil hydrolysis (656.0 ± 23.9 U/g) and ester synthesis (productivity of 6.8 mmol/min.gbiocat), and it has been chosen for further ester synthesis optimization. The effect of some important parameters such as biocatalyst concentration, reaction temperature and acid:alcohol molar ratio on the reaction has been evaluated using a central composite rotatable design at fixed mechanical stirring (240 rpm) and reaction time (15 min). Subsequently, the effect of reactants concentration and molecular sieve concentration has also been examined. Under optimal conditions (56 °C, acid:alcohol molar ratio of 1:3 with a palmitic acid concentration of 1 M, and 20% wt. of TLL–Octyl–SiO2 per volume of reaction mixture), 83% acid conversion was obtained after 150 min of reaction. The biocatalyst retained 87% of its initial activity after seven successive reaction batches. The product was identified by nuclear magnetic resonance analysis. Antimicrobial activity studies showed that the synthesized ester demonstrated antifungal activity against Candida albicans and Candida parapsilosis, with minimum inhibitory concentration (MIC) between 200 and 400 µg/mL, and bacteriostatic/fungistatic action—minimum microbicial concentration (MMC) > 400 µg/mL.

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Section: In Vitro Antimicrobial Activity Studysupporting

confidence: 91%

Sustainable Enzymatic Synthesis of a Solketal Ester—Process Optimization and Evaluation of Its Antimicrobial Activity

et al. 2020

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“…14 With numerous beneficial pharmacological properties, NH gradually became a new therapy to various disorders. 15 For instance, NH has been found to suppress the development of colorectal cancer through affecting intestinal flora; 15 NH exerts inhibitory effects on gram-negative and grampositive bacteria 16 and HCl/ethanol-induced gastric lesions, therefore might be useful for the protection of gastritis; 17 also NH could inhibit osteoclast differentiation and bone resorption. 18 However, the effect of NH on the differentiation of BMSCs still remained unknown.…”

Section: Introductionmentioning

confidence: 99%

<p>Neohesperidin Ameliorates Steroid-Induced Osteonecrosis of the Femoral Head by Inhibiting the Histone Modification of lncRNA HOTAIR</p>

Yuan¹,

Zhang²,

Zhu³

et al. 2020

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“…There are many examples of homo-multifunctional substrates that are modified using biocatalytic approaches, such as polyhydroxy [117][118][119][120][121][122][123][124][125][126][127][128], polycarboxylic [129][130][131], and polyamine Effect of the product inhibition on the reaction courses using two hypothetic enzymes, one with a very high initial activity but showing a strong inhibition by the product, the other with a lower activity but without product inhibition.…”

Section: Modification Of Multifunctional Substratesmentioning

confidence: 99%

One Pot Use of Combilipases for Full Modification of Oils and Fats: Multifunctional and Heterogeneous Substrates

et al. 2020

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Lipases are among the most utilized enzymes in biocatalysis. In many instances, the main reason for their use is their high specificity or selectivity. However, when full modification of a multifunctional and heterogeneous substrate is pursued, enzyme selectivity and specificity become a problem. This is the case of hydrolysis of oils and fats to produce free fatty acids or their alcoholysis to produce biodiesel, which can be considered cascade reactions. In these cases, to the original heterogeneity of the substrate, the presence of intermediate products, such as diglycerides or monoglycerides, can be an additional drawback. Using these heterogeneous substrates, enzyme specificity can promote that some substrates (initial substrates or intermediate products) may not be recognized as such (in the worst case scenario they may be acting as inhibitors) by the enzyme, causing yields and reaction rates to drop. To solve this situation, a mixture of lipases with different specificity, selectivity and differently affected by the reaction conditions can offer much better results than the use of a single lipase exhibiting a very high initial activity or even the best global reaction course. This mixture of lipases from different sources has been called “combilipases” and is becoming increasingly popular. They include the use of liquid lipase formulations or immobilized lipases. In some instances, the lipases have been coimmobilized. Some discussion is offered regarding the problems that this coimmobilization may give rise to, and some strategies to solve some of these problems are proposed. The use of combilipases in the future may be extended to other processes and enzymes.

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Microfluidic reactor for lipase-catalyzed regioselective synthesis of neohesperidin ester derivatives and their antimicrobial activity research

Cited by 21 publications

References 32 publications

Sustainable Enzymatic Synthesis of a Solketal Ester—Process Optimization and Evaluation of Its Antimicrobial Activity

Sustainable Enzymatic Synthesis of a Solketal Ester—Process Optimization and Evaluation of Its Antimicrobial Activity

<p>Neohesperidin Ameliorates Steroid-Induced Osteonecrosis of the Femoral Head by Inhibiting the Histone Modification of lncRNA HOTAIR</p>

One Pot Use of Combilipases for Full Modification of Oils and Fats: Multifunctional and Heterogeneous Substrates

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