Bioreduction of 4′-Hydroxychalcone in Deep Eutectic Solvents: Optimization and Efficacy with Various Yeast Strains
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PROVIDER: S-EPMC11241015 | biostudies-literature | 2024 Jun
REPOSITORIES: biostudies-literature
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Project description:Glycolipids are considered an alternative to petrochemically based surfactants because they are non-toxic, biodegradable, and less harmful to the environment while having comparable surface-active properties. They can be produced chemically or enzymatically in organic solvents or in deep eutectic solvents (DES) from renewable resources. DES are non-flammable, non-volatile, biodegradable, and almost non-toxic. Unlike organic solvents, sugars are easily soluble in hydrophilic DES. However, DES are highly viscous systems and restricted mass transfer is likely to be a major limiting factor for their application. Limiting factors for glycolipid synthesis in DES are not generally well understood. Therefore, the influence of external mass transfer, fatty acid concentration, and distribution on initial reaction velocity in two hydrophilic DES (choline:urea and choline:glucose) was investigated. At agitation speeds of and higher than 60 rpm, the viscosity of both DES did not limit external mass transfer. Fatty acid concentration of 0.5 M resulted in highest initial reaction velocity while higher concentrations had negative effects. Fatty acid accessibility was identified as a limiting factor for glycolipid synthesis in hydrophilic DES. Mean droplet sizes of fatty acid-DES emulsions can be significantly decreased by ultrasonic pretreatment resulting in significantly increased initial reaction velocity and yield (from 0.15 ± 0.03 μmol glucose monodecanoate/g DES to 0.57 ± 0.03 μmol/g) in the choline: urea DES. The study clearly indicates that fatty acid accessibility is a limiting factor in enzymatic glycolipid synthesis in DES. Furthermore, it was shown that physical pretreatment of fatty acid-DES emulsions is mandatory to improve the availability of fatty acids.
| S-EPMC7214929 | biostudies-literature
Project description:Chitin is the most abundant marine biopolymer, being recovered during the shell biorefining of crustacean shell waste. In its native form, chitin displays a poor reactivity and solubility in most solvents due to its extensive hydrogen bonding. This can be overcome by deacetylation. However, this process requires a high concentration of acids or bases at high temperatures, forming large amounts of toxic waste. Herein, we report on the first deacetylation with deep eutectic solvents (DESs) as an environmentally friendly alternative, requiring only mild reaction conditions. Biocompatible DESs are efficient in disturbing the native hydrogen-bonding network of chitin, readily dissolving it. First, quantum chemical calculations have been performed to evaluate the feasibility of different DESs to perform chitin deacetylation by studying their mechanism. Comparing these with the calculated barriers for garden-variety alkaline/acidic hydrolysis, which are known to proceed, prospective DESs were identified with barriers around 25 kcal·mol-1 or lower. Based on density functional theory results, an experimental screening of 10 distinct DESs for chitin deacetylation followed. The most promising DESs were identified as K2CO3:glycerol (K2CO3:G), choline chloride:acetic acid ([Ch]Cl:AA), and choline chloride:malic acid ([Ch]Cl:MA) and were subjected to further optimization with respect to the water content, process duration, and temperature. Ultimately, [Ch]Cl:MA showed the best results, yielding a degree of deacetylation (DDA) of 40% after 24 h of reaction at 120 °C, which falls slightly behind the threshold value (50%) for chitin to be considered chitosan. Further quantum chemical calculations were performed to elucidate the mechanism. Upon the removal of 40% N-acetyl groups from the chitin structure, its reactivity was considerably improved.
| S-EPMC8025712 | biostudies-literature
Project description:Deep eutectic solvents (DESs) are eutectic mixtures of salts and hydrogen bond donors with melting points low enough to be used as solvents. DESs have proved to be a good alternative to traditional organic solvents and ionic liquids (ILs) in many biocatalytic processes. Apart from the benign characteristics similar to those of ILs (e.g., low volatility, low inflammability and low melting point), DESs have their unique merits of easy preparation and low cost owing to their renewable and available raw materials. To better apply such solvents in green and sustainable chemistry, this review firstly describes some basic properties, mainly the toxicity and biodegradability of DESs. Secondly, it presents several valuable applications of DES as solvent/co-solvent in biocatalytic reactions, such as lipase-catalyzed transesterification and ester hydrolysis reactions. The roles, serving as extractive reagent for an enzymatic product and pretreatment solvent of enzymatic biomass hydrolysis, are also discussed. Further understanding how DESs affect biocatalytic reaction will facilitate the design of novel solvents and contribute to the discovery of new reactions in these solvents.
| S-EPMC5522511 | biostudies-other
Project description:The sustainable extraction of natural compounds has recently attracted significant attention. The extraction of high-quality natural vanillin in active form is crucial for its efficient use in various industries, but conventional solvents are not suitable for this purpose. The flammability, volatility, and toxicity of organic solvents can harm extraction personnel, and their waste liquid can cause environmental pollution. Natural deep eutectic solvents (NADES) are cost-effective, environmentally friendly, biodegradable, and non-toxic organic alternative to conventional solvents. In this study, 20 different NADES were tested for the sustainable extraction of natural vanillin. Among these, a DES system composed of choline chloride: 1,4-butanediol: lactic acid exhibited the highest extraction rate (15.9 mg/g). Employing response surface methodology (RSM), optimal extraction conditions were determined, yielding a vanillin content 18.5 mg/g with water content of 33.9%, extraction temperature of 64.6°C, extraction time of 32.3 min, and a solid-liquid ratio of 44.9 mg/mL. Subsequently, the optimized NADES system was then assessed for reusability in extracting vanillin from vanilla pods and kraft lignin over three cycles, retaining 43% of its extraction efficiency and demonstrating potential for waste reduction. Purification of vanillin was achieved through chromatography using a non-polar resin SP700, with ethanol as a desorption eluent and a feed solution pH of 4.0, resulting in the highest vanillin purity. HPLC and GC-MS analyses confirmed purity, while antioxidant activity assays (DPPH and ABTS) showcased significant antioxidant activity of the purified vanillin. Moreover, vanillin exhibited notable antimicrobial activity against a panel of food-borne bacteria. This study introduces an environmentally friendly approach to vanillin extraction highlights using NADES, emphasizing the potential for producing high-quality bioactive vanillin with reduced environmental impact. The applicability of NADES systems extends beyond vanillin, offering a versatile method for extracting diverse natural compounds.
| S-EPMC10875998 | biostudies-literature
Project description:Deep eutectic solvents (DESs) are an emerging class of modern, often "green" solvents with unique properties. Recently, a deep eutectic system based on amphiphilic surfactant N-alkyl-N,N-dimethyl-3-ammonio-1-propanesulfonate (C12 & C14 sulfobetaine) and (1S)-(+)-10-camphor-sulfonic acid in the molar ratio 1:1.5 has been reported. Nanostructuring can be expected in this DES due to the nature of the components. In this work, we have investigated the native nanostructure in the DES comprising C12-C18 alkyl chain sulfobetaines with camphor sulfonic acid and how it interacts with polar and nonpolar species, water and dodecane, respectively, using small angle neutron scattering. By using contrast variation to highlight the relative position of the solvent components and additives, we can resolve the structure of the solvent and how it changes upon interaction with water and dodecane. Scattering from the neat DES shows structures corresponding to the self-assembly of sulfobetaines; the size of the structure increases as the alkyl chain length of the sulfobetaines increases. Water and dodecane interact, respectively, with the hydrophilic and hydrophobic moieties in the DES structure, primarily the sulfobetaine, thereby swelling and solvating the entire structure. The extent of the shift of the peak position, and the swelling, depend on concentration of the additive. The solution phase organization and the interaction of polar and nonpolar species as observed here, have the potential to affect the ordering of inorganic or polymeric materials grown in such solvents, paving new avenues for templating applications.
| S-EPMC10688184 | biostudies-literature
Project description:Having been introduced in 2003, Deep Eutectic Solvents (DESs) make up a most recent category of green solvents. Due to their unique characteristics, and also their tunable physical properties, DESs have shown high potentials for use in various applications. One of the investigated applications is CO2 absorption. The thermodynamic modeling of CO2 solubility in DESs has been pursued by a number of researchers to estimate the capacity and capability of DESs for such tasks. Among the advanced equations of state (EoSs), the Perturbed Chain-Statistical Associating Fluid Theory (PC-SAFT) is a well-known EoS. In this study, the performance of the PC-SAFT EoS for estimating CO2 solubility in various DESs, within wide ranges of temperatures and pressures, was investigated. A large data bank, including 2542 CO2 solubility data in 109 various-natured DESs was developed and used for this study. This is currently the most comprehensive study in the open literature on CO2 solubility in DESs using an EoS. For modeling, the DES was considered as a pseudo-component with a 2B association scheme. CO2 was considered as both an inert and a 2B-component and the results of each association scheme were compared. Considering the very challenging task of modeling a complex hydrogen bonding mixture with gases, the results of AARD% being lower than 10% for both of the investigated association schemes of CO2, showed that PC-SAFT is a suitable model for estimating CO2 solubilities in various DESs. Also, by proposing generalized correlations to predict the PC-SAFT parameters, covering different families of DESs, the developed model provides a global technique to estimate CO2 solubilities in new and upcoming DESs, avoiding the necessity of further experimental work. This can be most valuable for screening and feasibility studies to select potential DESs from the innumerable options available.
| S-EPMC9395712 | biostudies-literature
Project description:The urgency of advancing green chemistry from labs and computers into the industries is well-known. The Deep Eutectic Solvents (DESs) are a promising category of novel green solvents which simultaneously have the best advantages of liquids and solids. Furthermore, they can be designed or engineered to have the characteristics desired for a given application. However, since they are rather new, there are no general models available to predict the properties of DESs without requiring other properties as input. This is particularly a setback when screening is required for feasibility studies, since a vast number of DESs are envisioned. For the first time, this study presents five group contribution (GC) and five atomic contribution (AC) models for densities, refractive indices, heat capacities, speeds of sound, and surface tensions of DESs. The models, developed using the most up-to-date databank of various types of DESs, simply decompose the molecular structure into a number of predefined groups or atoms. The resulting AARD% of densities, refractive indices, heat capacities, speeds of sound and surface tensions were, respectively, 1.44, 0.37, 3.26, 1.62, and 7.59% for the GC models, and 2.49, 1.03, 9.93, 4.52 and 7.80% for the AC models. Perhaps, even more importantly for designer solvents, is the predictive capability of the models, which was also shown to be highly reliable. Accordingly, very simple, yet highly accurate models are provided that are global for DESs and needless of any physical property information, making them useful predictive tools for a category of green solvents, which is only starting to show its potentials in green technology.
| S-EPMC7988013 | biostudies-literature
Project description:As functional liquid media, natural deep eutectic solvent (NADES) species can dissolve natural or synthetic chemicals of low water solubility. Moreover, the special properties of NADES, such as biodegradability and biocompatibility, suggest that they are alternative candidates for concepts and applications involving some organic solvents and ionic liquids. Owing to the growing comprehension of the eutectic mechanisms and the advancing interest in the natural eutectic phenomenon, many NADES applications have been developed in the past several years. However, unlike organic solvents, the basic structural unit of NADES media primarily depends on the intermolecular interactions among their components. This makes NADES matrices readily influenced by various factors, such as water content, temperature, and component ratio and, thus, extends the metabolomic challenge of natural products (NPs). To enhance the understanding of the importance of NADES in biological systems, this review focuses on NADES properties and applications in NP research. The present thorough chronological and statistical analysis of existing report adds to the recognition of the distinctiveness of (NA)DES, involves a discussion of NADES-related observations in NP research, and reportes applications of these eutectic mixtures. The work identifies potential areas for future studies of (NA)DES by evaluating relevant applications, including their use as extraction and chromatographic media as well as their biomedical relevance. The chemical diversity of natural metabolites that generate or participate in NADES formation highlights the growing insight that biosynthetically primordial metabolites (PRIMs) are as essential to the biological function and bioactivity of unrefined natural products as the biosynthetically more highly evolutionary metabolites (HEVOs) that can be isolated from crude mixtures.
| S-EPMC5913660 | biostudies-literature
Project description:This article provides an overview of a deep eutectic mixture based on the application of lithium nitrate (V) and acetamide as an electrolyte in a carbon-based electrochemical capacitor. This type of electrolyte is intended to be applied in devices designed for operation under critical conditions (e. g., extreme temperatures). In contrast to water- and common organic-based formulations, the proposed electrolyte ensures good device performance at 100 °C. To describe the chemistry of the proposed mixture, infrared and Raman spectroscopy, differential scanning calorimetry, and gas chromatography with mass spectrometry were used. Electrochemical analysis includes the verification of system ageing, self-discharge monitoring, leakage current measuring, and fundamental testing related to determining the specific capacitance or maximum voltage. Additionally, comprehensive analysis of the lithium nitrate salt and organic solvent addition to the operating system was carried out, including the replacement of lithium ions with sodium or potassium.
| S-EPMC8596588 | biostudies-literature
Project description:Deep eutectic solvents (DESs) are considered as efficient and green solvents for the extraction of bioactive compounds from medicinal plants. In this work, a novel method of DES-based ultrasound-assisted extraction of bioactive compounds from Baphicacanthus cusia leaves (BCL) was established. Systematic screening and the morphology of the original and treated BCL were observed with scanning electron microscopy to determine the extraction efficiency of different solvents. The extraction conditions were optimized by Box-Behnken design (BBD) tests and the optimal extraction conditions were as follows: lactic acid/L-menthol ratio of 5: 2 (mol/mol), solid-liquid ratio of 80.0 mL/g and temperature of 60.5 °C. The extraction yields of tryptanthrin, indigo and indirubin reached 0.356, 1.744 and 0.562 mg/g, respectively. The results of a 2,2-diphenyl-1-picrylhydrazy (DPPH) radical scavenging activity test indicated the feasibility of DESs in the extraction of bioactive compounds. This study indicated that L-menthol/lactic acid was a green and efficient solvent for the extraction of bioactive compounds from BCL, and DES-based ultrasound-assisted extraction could be used as an effective application strategy for the extraction of bioactive compounds from medicinal plants.
| S-EPMC8003621 | biostudies-literature