Lipase-catalyzed acylation of levoglucosan in continuous flow: antibacterial and biosurfactant studies

Nascimento, Marcelo A. do; Vargas, Juan P. C.; Rodrigues, José G. A.; Leão, Raquel A. C.; Moura, Patrícia Homobono Brito de; Leal, Ivana Correa Ramos; Bassut, Jonathan; Souza, Rodrigo O. M. A. de; Wojcieszak, Robert; Itabaiana, Ivaldo

doi:10.1039/d1ra08111j

Cited by 7 publications

(4 citation statements)

References 51 publications

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“…These antibacterial activities may be due to the presence of several compounds which have antimicrobial activity. These compounds include 2-furancarboxaldehyde; 5-(hydroxymethyl)- [28]; 1,6-anhydro-β-D-glucopyranose [29]; hexadecanoic acid; methyl ester; 9-octadecenoic acid; methyl ester [52]; heptadecanoic acid; 16-methyl ester [35]; phthalic acid; bis(7-methyloctyl) ester [41]; hordenine [61]; fraxetin [62]; piperine [63]; stearamide [64]; and erucamide [65]. Wahab et al reported the antibacterial activity against some Gram-positive and Gram-negative bacterial strains.…”

Section: Discussionmentioning

confidence: 99%

Chemical Characterisation, Antidiabetic, Antibacterial, and In Silico Studies for Different Extracts of Haloxylon stocksii (Boiss.) Benth: A Promising Halophyte

et al. 2023

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The objective of the study is to evaluate the chemical characterisation, and biological and in silico potential of Haloxylon stocksii (Boiss.) Benth, an important halophyte commonly used in traditional medicine. The research focuses on the roots and aerial parts of the plant and extracts them using two solvents: methanol and dichloromethane. Chemical characterisation of the extracts was carried out using total phenolic contents quantification, GC-MS analysis, and LC-MS screening. The results exhibited that the aerial parts of the plant have significantly higher total phenolic content than the roots. The GC-MS and LC-MS analysis of the plant extracts revealed the identification of 18 bioactive compounds in each. The biological evaluation was performed using antioxidant, antibacterial, and in vitro antidiabetic assays. The results exhibited that the aerial parts of the plant have higher antioxidant and in vitro antidiabetic activity than the roots. Additionally, the aerial parts of the plant were most effective against Gram-positive bacteria. Molecular docking was done to evaluate the binding affinity (BA) of the bioactive compounds characterised by GC-MS with diabetic enzymes used in the in vitro assay. The results showed that the BA of γ-sitosterol was better than that of acarbose, which is used as a standard in the in vitro assay. Overall, this study suggests that the extract from aerial parts of H. stocksii using methanol as a solvent have better potential as a new medicinal plant and can provide a new aspect to develop more potent medications. The research findings contribute to the scientific data of the medicinal properties of Haloxylon stocksii and provide a basis for further evaluation of its potential as a natural remedy.

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Section: Discussionmentioning

confidence: 99%

Chemical Characterisation, Antidiabetic, Antibacterial, and In Silico Studies for Different Extracts of Haloxylon stocksii (Boiss.) Benth: A Promising Halophyte

et al. 2023

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“…Cyanidin glycoside from trueno fruits ( Ligustrum japonicum ) was subjected to transesterification with vinyl cinnamate and cyanidin-3- O -(4‴-cinnamoyl)rutinoside ( Figure 2 e) and was synthesized at a 45.5% conversion yield [ 14 ]. The usage of vinyl esters in the enzymatic reactions is a well-known way to increase the conversion yield due to the shifting of the equilibrium state towards the formation of the product because of the tautomerization of vinyl alcohol to acetaldehyde [ 22 ].…”

Section: Lipophilization Of Extracts From Fruitsmentioning

confidence: 99%

Mini-Review on the Enzymatic Lipophilization of Phenolics Present in Plant Extracts with the Special Emphasis on Anthocyanins

et al. 2022

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Different plant extracts have the potential to be important sources of phenolic compounds. Their antibacterial, antifungal and antioxidant properties are of interest to researchers due to various possibilities for use in the pharmacy, cosmetic and food industries. Unfortunately, the direct application of phenolics in food is limited because of their hydrophilic nature and low solubility. The review is devoted to the recent advances in the methods of lipophilization of phenolic extracts along with the use of enzymes. The concept of extract modification instead of single compound modification is based on the expected synergistic effect of many phenolic compounds. The main focus is on the phenolic compounds found in fruits, flowers and leaves of different common and underutilized as well as medicinal, folk-medicinal or endemic plants. The compiled papers point to the great interest in the modification of anthocyanins, highly active but often unstable phenolics. Some examples of other flavonoids are also outlined. The possible applications of the lipophilized plant extracts are presented for improving the stability of edible oils, decreasing the content of acrylamide, exhibiting higher color stability in thermal processing and increasing the nutritional value.

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“…As extensively described in the literature, the spatial arrangement of the hydroxyl groups and consequent stabilization by intramolecular hydrogen bonds (Scheme ) hinder chemical and enzymatic transformations of LGA, leading to time-consuming reactions. , Enzymatically, the high polarity of LGA is also a disadvantage, restricting the scope of solvents suitable for use to a handful of polar solvents, which in general inhibit enzyme activity . Our research group has recently reported the high regioselectivity of Novozym 435 (N435, Candida antarctica lipase B immobilized on acrylic resin) toward C2 and C4 hydroxyl moieties during acetylation using long-chain aliphatic esters, while other lipases showed an increased preference for the OH at C4 at higher temperatures. , These findings have led to the possibility of synthesizing LGA-based linear polymers, possessing the rigid structure from LGA with pending hydroxyl moieties available for post-polymerization modifications.…”

Section: Introductionmentioning

confidence: 98%

“…In this context, levoglucosan (1,6-anhydro-β- d -glucopyranose; LGA) has been identified as an attractive chemical platform. − LGA is an anhydrous sugar obtained from the fast pyrolysis of cellulosethe major component of lignocellulosic biomass and has a rigid structure, with three hydroxyl groups disposed in trans -positions on a pyranose ring. It was already subjected to different reactions to produce diverse high-added value products, such as levoglucosenone, 5-hydroxymethylfurfural, furfural, glucose-6-phosphate, gluconic acid, sorbitol, and it was even tested for the production of biosurfactants and in antibacterial assays. − …”

Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Synthesis of Biobased Polyesters Containing Levoglucosan Units

Bassut

Nasr

Stoclet

et al. 2022

ACS Sustainable Chem. Eng.

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Levoglucosan (LGA) is an anhydrous pyrolytic sugar that has gained increasing attention in recent years. The highest focus on the conversion of LGA and other anhydro carbohydrates obtained from cellulose aims at the valorization of these molecules and their application in multiple fields such as chemical and pharmaceutical industries. LGA presents a rigid structure with three hydroxyl groups on a pyranose ring, making it a promising building block for the synthesis of bio-based thermoplastic polymers with pending OH groups as soon as a regioselective polymerization is reached. In this work, a lipase-catalyzed series of LGA-containing terpolymers were synthesized for the first time via regioselective transesterification in two-stage polymerization. LGA was reacted with diethyl adipate/sebacate and α,ω-diols to give terpolymers with up to 35% of LGA content (related to the α,ω-diol content), number-average molecular weights (M n) of up to 7900 g·mol–1, and up to 94% yield. It was observed that the amount of LGA in the polymer structure affects the crystallinity, hydrophilicity, and melting point of the polymers. We also evaluated the effect of LGA loading and the comonomer’s size on yields, molecular weight, and the incorporation of LGA in the polymer structure. High loads of LGA lead to a decrease in the yield, but a higher molecular weight and higher extent of LGA incorporation in the polymer can be obtained.

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Lipase-catalyzed acylation of levoglucosan in continuous flow: antibacterial and biosurfactant studies

Abstract: Ipase-catalyzed transesterification of LG under continuous flow conditions.

Cited by 7 publications

References 51 publications

Chemical Characterisation, Antidiabetic, Antibacterial, and In Silico Studies for Different Extracts of Haloxylon stocksii (Boiss.) Benth: A Promising Halophyte

Chemical Characterisation, Antidiabetic, Antibacterial, and In Silico Studies for Different Extracts of Haloxylon stocksii (Boiss.) Benth: A Promising Halophyte

Mini-Review on the Enzymatic Lipophilization of Phenolics Present in Plant Extracts with the Special Emphasis on Anthocyanins

Lipase-Catalyzed Synthesis of Biobased Polyesters Containing Levoglucosan Units

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