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1.
Nat Commun ; 15(1): 7151, 2024 Aug 21.
Article de Anglais | MEDLINE | ID: mdl-39169043

RÉSUMÉ

Separations are core processes in the chemical and pharmaceutical industries. Several steps of fractionation and purification of multicomponent mixtures are required. Membrane technology can operate at fair temperatures, saving energy and processing sensitive compounds. However, breakthroughs require high stability and selectivity beyond those available today. Here, we propose membranes constituted by fully crosslinked crown ethers using interfacial polymerization. The 24 nm-thick nanofilms on robust porous supports exhibit up to 90% higher selectivity than commercially available membranes, with a 90% increase in solvent permeance. The membranes are tested with a complex mixture of structurally diverse solutes containing active pharmaceutical ingredients. The membranes are effective for the total retention and concentration of active pharmaceutical ingredients with molecular weights around 800 g mol-1. The ability to distinguish between smaller molecules in the range between 100 and 370 g mol-1 is confirmed with high separation factors, which could provide a significant advance for the pharmaceutical industry.


Sujet(s)
Membrane artificielle , Solvants , Solvants/composition chimique , Préparations pharmaceutiques/composition chimique , Préparations pharmaceutiques/isolement et purification , Porosité , Éthers couronnes/composition chimique , Composés macrocycliques/composition chimique , Polymérisation , Masse moléculaire
2.
Proc Natl Acad Sci U S A ; 121(35): e2408554121, 2024 Aug 27.
Article de Anglais | MEDLINE | ID: mdl-39172789

RÉSUMÉ

Biomolecules can be sequestered into membrane-less compartments, referred to as biomolecular condensates. Experimental and computational methods have helped define the physical-chemical properties of condensates. Less is known about how the high macromolecule concentrations in condensed phases contribute "solvent" interactions that can remodel the free-energy landscape of other condensate-resident proteins, altering thermally accessible conformations and, in turn, modulating function. Here, we use solution NMR spectroscopy to obtain atomic resolution insights into the interactions between the immature form of superoxide dismutase 1 (SOD1), which can mislocalize and aggregate in stress granules, and the RNA-binding protein CAPRIN1, a component of stress granules. NMR studies of CAPRIN1:SOD1 interactions, focused on both unfolded and folded SOD1 states in mixed phase and demixed CAPRIN1-based condensates, establish that CAPRIN1 shifts the SOD1 folding equilibrium toward the unfolded state through preferential interactions with the unfolded ensemble, with little change to the structure of the folded conformation. Key contacts between CAPRIN1 and the H80-H120 region of unfolded SOD1 are identified, as well as SOD1 interaction sites near both the arginine-rich and aromatic-rich regions of CAPRIN1. Unfolding of immature SOD1 in the CAPRIN1 condensed phase is shown to be coupled to aggregation, while a more stable zinc-bound, dimeric form of SOD1 is less susceptible to unfolding when solvated by CAPRIN1. Our work underscores the impact of the condensate solvent environment on the conformational states of resident proteins and supports the hypothesis that ALS mutations that decrease metal binding or dimerization function as drivers of aggregation in condensates.


Sujet(s)
Solvants , Superoxide dismutase-1 , Superoxide dismutase-1/composition chimique , Superoxide dismutase-1/métabolisme , Superoxide dismutase-1/génétique , Humains , Solvants/composition chimique , Dépliement des protéines , Liaison aux protéines , Pliage des protéines , Modèles moléculaires , Granules de stress/métabolisme , Granules de stress/composition chimique , Protéines de liaison à l'ARN/métabolisme , Protéines de liaison à l'ARN/composition chimique , Conformation des protéines , Spectroscopie par résonance magnétique
3.
Article de Anglais | MEDLINE | ID: mdl-39147448

RÉSUMÉ

In the present study, we investigated the genotoxicity of the active products formed from N-nitrosoproline (NPRO) dissolved in oleic acid following ultraviolet A (UVA) irradiation, bypassing the need for metabolic activation. We previously demonstrated the photomutagenicity of NPRO dissolved in a phosphate-buffered solution. It has been suggested that the association of the nitrosamine group with acid ions facilitates rapid photodissociation and photoactivation. We hypothesized that NPRO's inherent carboxyl group may mimic an acid, inducing photodissociation and photomutagenicity, even in a non-aqueous solvent lacking acidic ions. Following UVA irradiation, NPRO dissolved in oleic acid exhibited a dose-dependent mutagenic activity. Similar results were obtained when NPRO was dissolved in linoleic acid and triolein. Nitric oxide formation, which is dependent on NPRO concentration, is accompanied by mutagenic activity. The mutagenicity spectrum obtained in response to NPRO irradiation followed the absorption curve of NPRO dissolved in oleic acid. Irradiated NPRO in oleic acid displayed relative stability, retaining approximately 18, 36, and 63 % of initial mutagenicity after 10 days of storage at 25, 4, and -20 °C, respectively. Thus NPRO stored in a fatty environment undergoes photoactivation upon irradiation, leading to genotoxicity.


Sujet(s)
Tests de mutagénicité , Acide oléique , Solvants , Rayons ultraviolets , Acide oléique/composition chimique , Solvants/composition chimique , Mutagènes/composition chimique , Mutagènes/toxicité , Monoxyde d'azote/composition chimique , Monoxyde d'azote/métabolisme , Salmonella typhimurium/effets des médicaments et des substances chimiques , Salmonella typhimurium/génétique , Salmonella typhimurium/effets des radiations
4.
Pharmazie ; 79(7): 146-150, 2024 Aug 01.
Article de Anglais | MEDLINE | ID: mdl-39152556

RÉSUMÉ

The principal aim of this study was to optimize analytical methodology based on mass spectrometry for the evaluation of the quality of recombinant human insulin and its analogs. In this study ESI-MS was used to assess the quality of human insulin, short acting insulin analogs, insulin lispro, insulin aspart and insulin glulisine and long acting analogs including insulin glargine, insulin degludec, and insulin detemir, in respective pharmaceutical formulations. In this study, with the aimed to optimize analytical conditions, different factors influencing the analytical performance such as pH, ionic strength, sample dilution, organic solvent addition were addressed. The study results demonstrated that MS is a suitable technique for the analysis of biotechnological compounds like insulin and its analogs. Although the obtained results provide an important information regarding this methodology, further studies are needed to validate this analytical approach and check for its suitability to be used in the regulatory environment.


Sujet(s)
Insuline , Spectrométrie de masse ESI , Spectrométrie de masse ESI/méthodes , Insuline/composition chimique , Insuline/analyse , Insuline/analogues et dérivés , Contrôle de qualité , Concentration en ions d'hydrogène , Humains , Concentration osmolaire , Hypoglycémiants/composition chimique , Hypoglycémiants/analyse , Insuline à longue durée d'action/composition chimique , Chimie pharmaceutique/méthodes , Solvants/composition chimique
5.
J Environ Manage ; 367: 121969, 2024 Sep.
Article de Anglais | MEDLINE | ID: mdl-39098073

RÉSUMÉ

This study proposes liquid-liquid extraction (LLE) for the recovery of phenolic acids from winery wastewater replacing common volatile organic compounds (VOCs) with environmentally friendly solvents. On one hand, terpenes (α-pinene and p-cymene) and terpenoids (eucalyptol and linalool) were selected as green solvents and compared to common VOCs (ethyl acetate or 1-butanol). On the other hand, gallic acid (GA), vanillic acid (VA), syringic acid (SA) and caffeic acid (CA) were selected as phenolic acids to be recovered. The extraction performance was evaluated under different operation conditions: solvent-to-feed ratio, initial concentration of phenolic acids and temperature. This work also evaluated the back-extraction whole process global recovery and solvent regeneration, by means of aqueous NaOH solution. Eucalyptol has shown the highest overall global extraction performance (21.07 % for GA, 93.21 % for VA, 78.79 % for SA, and 80.57 % for CA) and lower water solubility compared to the best performing VOC solvent (1-butanol). Therefore, eucalyptol can be a potential eco-friendly solvent to replace VOCs for sustainable phenolic acid recovery from winery wastewater. Finally, to ensure a clean water stream after the LLE, the traces of solvent were completely removed by electrooxidation with boron-doped diamond anode at a current density of 422.54 A/m2.


Sujet(s)
Hydroxybenzoates , Extraction liquide-liquide , Solvants , Eaux usées , Eaux usées/composition chimique , Extraction liquide-liquide/méthodes , Solvants/composition chimique , Hydroxybenzoates/composition chimique , Composés organiques volatils/composition chimique , Vin
6.
Anal Chem ; 96(32): 13166-13173, 2024 Aug 13.
Article de Anglais | MEDLINE | ID: mdl-39092810

RÉSUMÉ

For the approval of a drug, the stability data must be submitted to regulatory authorities. Such analyses are often time-consuming and cost-intensive. Forced degradation studies are mainly carried out under harsh conditions in the dissolved state, often leading to extraneous degradation profiles for a solid drug. Oxidative mechanochemical degradation offers the possibility of generating realistic degradation profiles. In this study, a sustainable mechanochemical procedure is presented for the degradation of five active pharmaceutical ingredients (APIs) from the sartan family: losartan potassium, irbesartan, valsartan, olmesartan medoxomil, and telmisartan. High-resolution mass spectrometry enabled the detection of impurities already present in untreated APIs and allowed the elucidation of degradation products. Significant degradation profiles could already be obtained after 15-60 min of ball milling time. Many of the identified degradation products are described in the literature and pharmacopoeias, emphasizing the significance of our results and the applicability of this approach to predict degradation profiles for drugs in the solid state.


Sujet(s)
Benzimidazoles , Dérivés du biphényle , Losartan , Telmisartan , Tétrazoles , Valsartan , Benzimidazoles/composition chimique , Benzimidazoles/analyse , Tétrazoles/composition chimique , Telmisartan/composition chimique , Valsartan/composition chimique , Losartan/composition chimique , Losartan/analyse , Dérivés du biphényle/composition chimique , Irbésartan/composition chimique , Irbésartan/analyse , Imidazoles/composition chimique , Benzoates/composition chimique , Valine/composition chimique , Valine/analyse , Solvants/composition chimique , Stabilité de médicament
7.
Biomed Mater ; 19(5)2024 Aug 13.
Article de Anglais | MEDLINE | ID: mdl-39094613

RÉSUMÉ

The design of three-dimensional (3D) scaffolds should focus on creating highly porous, 3D structures with an interconnected pore network that supports cell growth. The scaffold's pore interconnectivity is directly linked to vascularization, cell seeding, guided cell migration, and transportation of nutrients and metabolic waste. In this study, different types of food flavors including monosodium glutamate, sugar, and sodium chloride were used as the porogens along with PCL/PVP blend polymer for solvent casting/particulate leaching method. The morphology, porosity, interconnectivity, chemical composition, water absorption, and mechanical properties of the fabricated scaffolds are carefully characterized. The scaffolds are biocompatible in bothin vitroandin vivoexperiments and do not trigger any inflammatory response while enhancing new bone formation and vascularization in rabbit calvaria critical-sized defects. The new bone merges and becomes denser along with the experiment timeline. The results indicate that the 3D PCL/PVP scaffolds, using monosodium glutamate as porogen, exhibited suitable biological performance and held promise for bone tissue engineering in oral and maxillofacial surgery.


Sujet(s)
Matériaux biocompatibles , Glutamate de sodium , Solvants , Ingénierie tissulaire , Structures d'échafaudage tissulaires , Animaux , Structures d'échafaudage tissulaires/composition chimique , Lapins , Ingénierie tissulaire/méthodes , Porosité , Solvants/composition chimique , Matériaux biocompatibles/composition chimique , Matériaux biocompatibles/pharmacologie , Polyesters/composition chimique , Test de matériaux , Crâne/effets des médicaments et des substances chimiques , Polyvinyles/composition chimique , Régénération osseuse/effets des médicaments et des substances chimiques , Ostéogenèse/effets des médicaments et des substances chimiques , Substituts osseux/composition chimique , Substituts osseux/pharmacologie , Os et tissu osseux/métabolisme
8.
AAPS J ; 26(5): 89, 2024 Aug 02.
Article de Anglais | MEDLINE | ID: mdl-39150583

RÉSUMÉ

A non-invasive capacitance instrument was embedded in the base of a vacuum-drying tray to monitor continuously the residual amount of solvent left in a pharmaceutical powder. Proof of concept was validated with Microcrystalline Cellulose laced with water, as well as water/acetone mixtures absorbed in a spray-dried Copovidone powder. To illustrate the role of impermeability of the base, we derive a model of vapor sorption that reveals the existence of a kinetic limit when solids are thinly spread, and a diffusion limit with greatly diminished effective diffusivity at large powder thickness. By monitoring the residual solvent content of powders, this new in situ technique offers advantages over indirect methods like mass spectrometry of vapor effluents, but without complications associated with probe fouling. To prescribe design guidelines and interpret signals, we model the electric field shed by the probe when a powder holds variable solvent mass fraction in the vertical direction.


Sujet(s)
Cellulose , Poudres , Solvants , Solvants/composition chimique , Vide , Cellulose/composition chimique , Cellulose/analyse , Pyrrolidines/composition chimique , Pyrrolidines/analyse , Composés vinyliques/composition chimique , Eau/composition chimique , Dessiccation/méthodes , Acétone/analyse , Acétone/composition chimique , Diffusion , Cinétique
9.
J Pharm Biomed Anal ; 249: 116327, 2024 Oct 15.
Article de Anglais | MEDLINE | ID: mdl-39089199

RÉSUMÉ

Pharmaceutical manufacturing utilizes solvents at different stages of production. Some of the harmful solvent residuals may be retained in the final product; therefore, they need to be monitored for quality control and to meet the regulation requirement. Here, a novel method capable of rapidly analyzing residual solvents in pharmaceutical products was developed using a compact-portable gas chromatography with a photoionization detector (GC-PID). The method consists of modified Tedlar® bag sampling, online pre-concentration, separation of volatiles by miniaturized GC, and micro-PID detection. The method detection limits of selected residual solvents were in the range of 26.00 - 52.03 pg/mL which is much lower than the pharmaceutical compliance concentration limits. Limits of detection > 520 pg of analyte per grams of sample was also determined for the over-the-counter drugs. The method performance showed rapid speed (5 min), linear calibration (r2 < 0.99), and repeatable retention time (RSD < 0.4 %). Direct analysis of residual solvents in solid samples was conducted without the need for complex sample preparation. The method validation using over-the-counter pharmaceutical products yielded excellent accuracy (recovery > 91.2 %) and precision (RSD < 6.5 %) for the selected residual solvents, including 1,4-dioxane, benzene, chlorobenzene, cyclohexane, xylenes, and toluene. This portable and rapid method could be deployed during the pharmaceutical drug manufacturing processes for quality control.


Sujet(s)
Limite de détection , Solvants , Solvants/composition chimique , Solvants/analyse , Chromatographie en phase gazeuse/méthodes , Chromatographie en phase gazeuse/instrumentation , Contamination de médicament/prévention et contrôle , Préparations pharmaceutiques/analyse , Contrôle de qualité , Reproductibilité des résultats , Calibrage
10.
J Sep Sci ; 47(15): e2400275, 2024 Aug.
Article de Anglais | MEDLINE | ID: mdl-39091185

RÉSUMÉ

In this study, we propose a novel strategy utilizing deep eutectic solvents (DESs) as both the extraction solvent and dispersing liquid, with nanometer zinc oxide (ZnO) serving as the adsorbent. This method incorporates ultrasound-assisted matrix solid phase dispersion (UA-MSPD) for the extraction of six active components (salidroside, echinacoside, acteoside, specnuezhenide, nuezhenoside G13, and oleanolic acid) from Ligustri Lucidi Fructus samples. The extracts were then analyzed using high-performance liquid chromatography equipped with a diode array detector. The effects of various parameters such as dispersant dosage, DESs volume, grinding time, ultrasonication duration, and eluent volume on extraction recovery were investigated and optimized using a central composite design under response surface methodology. The optimized conditions yielded detection limits ranging from 0.003 to 0.01 mg/g and relative standard deviations of 8.7% or lower. Extraction recoveries varied between 93% and 98%. The method demonstrated excellent linearity for the analytes (R2 ≥ 0.9997). The simple, green, and efficient DESs/ZnO-UA-MSPD technique proved to be rapid, accurate, and reliable for extracting and analyzing the six active ingredients in Ligustri Lucidi Fructus samples.


Sujet(s)
Ligustrum , Extraction en phase solide , Ondes ultrasonores , Oxyde de zinc , Extraction en phase solide/méthodes , Oxyde de zinc/composition chimique , Ligustrum/composition chimique , Solvants eutectiques profonds/composition chimique , Chromatographie en phase liquide à haute performance , Fruit/composition chimique , Extraits de plantes/composition chimique , Extraits de plantes/analyse , Taille de particule , Solvants/composition chimique
11.
Commun Biol ; 7(1): 968, 2024 Aug 09.
Article de Anglais | MEDLINE | ID: mdl-39122990

RÉSUMÉ

Aggregation-prone-motifs (APRs) of proteins are short segments, which - as isolated peptides - form diverse amyloid-like crystals. We introduce two APRs - designed variants of the incretin mimetic Exendin-4 - that both display crystal-phase polymorphism. Crystallographic and spectroscopic analysis revealed that a single amino-acid substitution can greatly reduce topological variability: while LYIQWL can form both parallel and anti-parallel ß-sheets, LYIQNL selects only the former. We also found that the parallel/anti-parallel switch of LYIQWL can be induced by simply changing the crystallization temperature. One crystal form of LYIQNL was found to belong to the class 3 topology, an arrangement previously not encountered among proteinogenic systems. We also show that subtle environmental changes lead to crystalline assemblies with different topologies, but similar interfaces. Spectroscopic measurements showed that polymorphism is already apparent in the solution state. Our results suggest that the temperature-, sequence- and environmental sensitivity of physiological amyloids is reflected in assemblies of the APR segments, which, complete with the new class 3 crystal form, effectively sample all the originally proposed basic topologies of amyloid-like aggregates.


Sujet(s)
Amyloïde , Solvants , Amyloïde/composition chimique , Amyloïde/génétique , Amyloïde/métabolisme , Solvants/composition chimique
12.
Int J Mol Sci ; 25(15)2024 Jul 28.
Article de Anglais | MEDLINE | ID: mdl-39125824

RÉSUMÉ

The study presents a thorough and detailed analysis of bicalutamide's structural and conformational properties. Quantum chemical calculations were employed to explore the conformational properties of the molecule, identifying significant energy differences between conformers. Analysis revealed that hydrogen bonds stabilise the conformers, with notable variations in torsion angles. Conformers were classified into 'closed' and 'open' types based on the relative orientation of the cyclic fragments. NOE spectroscopy in different solvents (CDCl3 and DMSO-d6) was used to study the conformational preferences of the molecule. NOESY experiments provided the predominance of 'closed' conformers in non-polar solvents and a significant presence of 'open' conformers in polar solvents. The proportions of open conformers were 22.7 ± 3.7% in CDCl3 and 59.8 ± 6.2% in DMSO-d6, while closed conformers accounted for 77.3 ± 3.7% and 40.2 ± 6.2%, respectively. This comprehensive study underscores the solvent environment's impact on its structural behaviour. The findings significantly contribute to a deeper understanding of conformational dynamics, stimulating further exploration in drug development.


Sujet(s)
Anilides , Liaison hydrogène , Spectroscopie par résonance magnétique , Conformation moléculaire , Nitriles , Solvants , Composés tosyliques , Anilides/composition chimique , Composés tosyliques/composition chimique , Solvants/composition chimique , Nitriles/composition chimique , Spectroscopie par résonance magnétique/méthodes , Théorie quantique , Modèles moléculaires , Solutions
13.
Int J Mol Sci ; 25(15)2024 Jul 29.
Article de Anglais | MEDLINE | ID: mdl-39125847

RÉSUMÉ

Lignin, the second most abundant natural polymer, is a by-product of the biorefinery and pulp and paper industries. This study was undertaken to evaluate the properties and estimate the prospects of using lignin as a by-product of the pretreatment of common reed straw (Phragmites australis) with deep eutectic solvents (DESs) of various compositions: choline chloride/oxalic acid (ChCl/OA), choline chloride/lactic acid (ChCl/LA), and choline chloride/monoethanol amine (ChCl/EA). The lignin samples, hereinafter referred to as Lig-OA, Lig-LA, and Lig-EA, were obtained as by-products after optimizing the conditions of reed straw pretreatment with DESs in order to improve the efficiency of subsequent enzymatic hydrolysis. The lignin was studied using gel penetration chromatography, UV-vis, ATR-FTIR, and 1H and 13C NMR spectroscopy; its antioxidant activity was assessed, and the UV-shielding properties of lignin/polyvinyl alcohol composite films were estimated. The DES composition had a significant impact on the structure and properties of the extracted lignin. The lignin's ability to scavenge ABTS+• and DPPH• radicals, as well as the efficiency of UV radiation shielding, decreased as follows: Lig-OA > Lig-LA > Lig-EA. The PVA/Lig-OA and PVA/Lig-LA films with a lignin content of 4% of the weight of PVA block UV radiation in the UVA range by 96% and 87%, respectively, and completely block UV radiation in the UVB range.


Sujet(s)
Antioxydants , Solvants eutectiques profonds , Lignine , Poaceae , Rayons ultraviolets , Lignine/composition chimique , Antioxydants/composition chimique , Antioxydants/pharmacologie , Solvants eutectiques profonds/composition chimique , Poaceae/composition chimique , Technologie de la chimie verte/méthodes , Solvants/composition chimique
14.
Luminescence ; 39(8): e4868, 2024 Aug.
Article de Anglais | MEDLINE | ID: mdl-39143679

RÉSUMÉ

A pair of 1,8-naphthalimides (NPIs) were designed and successfully synthesized through embellishing amino-containing NPI with 4-diethylaminosalicyladehyde and 4-diethylaminobenzaldehyde, respectively. Their structures were fully confirmed by 1H/13C NMR, HR-MS and FT-IR spectroscopic studies. Their photophysical properties were systematically investigated in different solvents of varied polarity, in THF/water mixtures with varying water fractions (fw), and in THF solvent with varying concentrations of NPIs. It inferred that the distinct differences in emission between two NPIs during self-assembled process could be ascribed that the hydroxyl-containing NPI allowed the excited-state intramolecular proton transfer process between -OH and CH=N units in the aggregation state. Interestingly, the solid of 4-diethylaminosalicyladehyde-functionalized NPI exhibited multi-stimuli-responsive fluorescence changes involving mechanofluorochromism and HCl/NH3 vapor stimulus-induced conversion. However, no remarkable change was observed in the photoluminescence (PL) spectra for the solid of 4-diethylaminobenzaldehyde-functionalized NPI under the stimuli of mechanical force and organic solvent.


Sujet(s)
Dérivés de la benzo[de]isoquinoléine-1,3-dione , Dérivés de la benzo[de]isoquinoléine-1,3-dione/composition chimique , Colorants fluorescents/composition chimique , Colorants fluorescents/synthèse chimique , Structure moléculaire , Solvants/composition chimique , Spectrométrie de fluorescence , Fluorescence
15.
Molecules ; 29(15)2024 Jul 25.
Article de Anglais | MEDLINE | ID: mdl-39124900

RÉSUMÉ

Cellulose and lignin, sourced from biomass, hold potential for innovative bioprocesses and biomaterials. However, traditional fractionation and purification methods often rely on harmful chemicals and high temperatures, making these processes both hazardous and costly. This study introduces a sustainable approach for fractionating acacia wood, focusing on both cellulose and lignin extraction using a deep eutectic solvent (DES) composed of choline chloride (ChCl) and levulinic acid (LA). A design of experiment was employed for the optimization of the most relevant fractionation parameters: time and temperature. In the case of the lignin, both parameters were found to be significant variables in the fractionation process (p-values of 0.0128 and 0.0319 for time and temperature, respectively), with a positive influence. Likewise, in the cellulose case, time and temperature also demonstrated a positive effect, with p-values of 0.0103 and 0.028, respectively. An optimization study was finally conducted to determine the maximum fractionation yield of lignin and cellulose. The optimized conditions were found to be 15% (w/v) of the wood sample in 1:3 ChCl:LA under a treatment temperature of 160 °C for 8 h. The developed method was validated through repeatability and intermediate precision studies, which yielded a coefficient of variation lower than 5%. The recovery and reuse of DES were successfully evaluated, revealing remarkable fractionation yields even after five cycles. This work demonstrates the feasibility of selectively extracting lignin and cellulose from woody biomass using a sustainable solvent, thus paving the way for valorization of invasive species biomass.


Sujet(s)
Acacia , Cellulose , Fractionnement chimique , Solvants eutectiques profonds , Lignine , Bois , Lignine/composition chimique , Lignine/isolement et purification , Cellulose/composition chimique , Acacia/composition chimique , Bois/composition chimique , Fractionnement chimique/méthodes , Solvants eutectiques profonds/composition chimique , Solvants/composition chimique , Température , Biomasse
16.
Molecules ; 29(15)2024 Aug 02.
Article de Anglais | MEDLINE | ID: mdl-39125062

RÉSUMÉ

This study aims to extract phenolic-enriched compounds, specifically oleuropein, luteoloside, and hydroxytyrosol, from olive leaves using ball milling-assisted extraction (BMAE). Response surface methodology (RSM) and the Box-Behnken design (BBD) were used to evaluate the effects of the temperature, solvent-to-solid ratio, and milling speed on extraction recovery. The contents of the extract were determined by ultra-high-performance liquid chromatography-mass spectrometry (UPLC-MS) and converted to recoveries to evaluate the extraction efficiency. The optimal extraction conditions for oleuropein, luteoloside, and hydroxytyrosol were identified. Oleuropein had a recovery of 79.0% ± 0.9% at a temperature of 56.4 °C, a solvent-to-solid ratio of 39.1 mL/g, and a milling speed of 429 rpm. Luteoloside's recovery was 74.6% ± 1.2% at 58.4 °C, 31.3 mL/g, and 328 rpm. Hydroxytyrosol achieved 43.1% ± 1.3% recovery at 51.5 °C, 32.7 mL/g, and 317 rpm. The reason for the high recoveries might be that high energy ball milling could reduce the sample size further, breaking down the cell walls of olive leaves, to enhance the mass transfer of these components from the cell to solvent. BMAE is displayed to be an efficient approach to extracting oleuropein, luteoloside, and hydroxytyrosol from olive leaves, which is easy to extend to industrial production.


Sujet(s)
Glucosides d'iridoïdes , Olea , Phénols , Extraits de plantes , Feuilles de plante , Olea/composition chimique , Feuilles de plante/composition chimique , Phénols/composition chimique , Phénols/isolement et purification , Phénols/analyse , Extraits de plantes/composition chimique , Glucosides d'iridoïdes/composition chimique , Chromatographie en phase liquide à haute performance/méthodes , Alcool phénéthylique/analogues et dérivés , Alcool phénéthylique/composition chimique , Alcool phénéthylique/isolement et purification , Iridoïdes/composition chimique , Iridoïdes/isolement et purification , Spectrométrie de masse , Solvants/composition chimique
17.
Molecules ; 29(15)2024 Aug 02.
Article de Anglais | MEDLINE | ID: mdl-39125075

RÉSUMÉ

Banana peels, comprising about 35% of the fruit's weight, are often discarded, posing environmental and economic issues. This research focuses on recycling banana peel waste by optimizing advanced extraction techniques, specifically microwave-assisted (MAE) and ultrasound-assisted extraction (UAE), for the isolation of phenolic compounds. A choline chloride-based deep eutectic solvent (DES) with glycerol in a 1:3 ratio with a water content of 30% (w/w) was compared to 30% ethanol. Parameters, including sample-to-solvent ratio (SSR), extraction time, and temperature for MAE or amplitude for UAE, were varied. Extracts were analyzed for hydroxycinnamic acid (HCA) and flavonoid content, and antioxidant activity using FRAP and ABTS assays. DES outperformed ethanol, with HCA content ranging from 180.80 to 765.92 mg/100 g and flavonoid content from 96.70 to 531.08 mg/100 g, accompanied by higher antioxidant activity. Optimal MAE conditions with DES were an SSR of 1:50, a temperature of 60 °C, and a time of 10 min, whereas an SSR of 1:60, time of 5 min, and 75% amplitude were optimal for UAE. The polyphenolic profile of optimized extracts comprised 19 individual compounds belonging to the class of flavonols, flavan-3-ols, and phenolic acids. This study concluded that DESs, with their superior extraction efficiency and environmental benefits, are promising solvents for the extraction of high-value bioactive compounds from banana peels and offer significant potential for the food and pharmaceutical industries.


Sujet(s)
Antioxydants , Solvants eutectiques profonds , Musa , Phénols , Extraits de plantes , Musa/composition chimique , Phénols/composition chimique , Phénols/isolement et purification , Phénols/analyse , Antioxydants/composition chimique , Antioxydants/isolement et purification , Extraits de plantes/composition chimique , Extraits de plantes/isolement et purification , Solvants eutectiques profonds/composition chimique , Flavonoïdes/composition chimique , Flavonoïdes/isolement et purification , Fruit/composition chimique , Micro-ondes , Technologie de la chimie verte/méthodes , Solvants/composition chimique
18.
Chem Pharm Bull (Tokyo) ; 72(7): 648-657, 2024.
Article de Anglais | MEDLINE | ID: mdl-38972722

RÉSUMÉ

Butin and butein are significant bioactive flavanones derived from plants, existing as tautomers of each other. However, their physicochemical attributes, such as their spectral profiles under varying experimental conditions in aqueous solutions and established chromatographic methods for distinguishing between them, remain undetermined. In this study, we determined the basic properties of butin and butein using conventional spectroscopic, reversed-phase, and chiral HPLC analyses. The spectra of the synthesized butin and butein were analyzed using a UV-Vis spectrophotometer in several solvents with different polarities as well as in aqueous solutions at various pH values. Furthermore, the behavior of the measured spectra was reproduced by calculations to reveal the effects of the solvent and pH on the spectra of butin and butein in organic and aqueous solutions. Subsequently, we assessed the structural stability of butin and butein using reversed-phase HPLC, which revealed that butein is unstable compared with butin in a general culture medium. The synthesized butin was effectively separated into R- and S-isomers with positive and negative Cotton effects, respectively, via HPLC using a chiral column. These findings will aid in uncovering the individual properties of both butin and butein that may have been concealed by their tautomerism and enable the synthesis of S-butin, which is typically challenging and time-consuming to isolate.


Sujet(s)
Chalcones , Chromatographie en phase liquide à haute performance , Chalcones/composition chimique , Chalcones/synthèse chimique , Spectrophotométrie UV , Structure moléculaire , Concentration en ions d'hydrogène , Flavanones/composition chimique , Flavanones/synthèse chimique , Flavanones/analyse , Stéréoisomérie , Solvants/composition chimique
19.
Sci Data ; 11(1): 742, 2024 Jul 07.
Article de Anglais | MEDLINE | ID: mdl-38972891

RÉSUMÉ

We here introduce the Aquamarine (AQM) dataset, an extensive quantum-mechanical (QM) dataset that contains the structural and electronic information of 59,783 low-and high-energy conformers of 1,653 molecules with a total number of atoms ranging from 2 to 92 (mean: 50.9), and containing up to 54 (mean: 28.2) non-hydrogen atoms. To gain insights into the solvent effects as well as collective dispersion interactions for drug-like molecules, we have performed QM calculations supplemented with a treatment of many-body dispersion (MBD) interactions of structures and properties in the gas phase and implicit water. Thus, AQM contains over 40 global and local physicochemical properties (including ground-state and response properties) per conformer computed at the tightly converged PBE0+MBD level of theory for gas-phase molecules, whereas PBE0+MBD with the modified Poisson-Boltzmann (MPB) model of water was used for solvated molecules. By addressing both molecule-solvent and dispersion interactions, AQM dataset can serve as a challenging benchmark for state-of-the-art machine learning methods for property modeling and de novo generation of large (solvated) molecules with pharmaceutical and biological relevance.


Sujet(s)
Théorie quantique , Solvants , Solvants/composition chimique , Préparations pharmaceutiques/composition chimique , Eau/composition chimique , Conformation moléculaire
20.
Water Environ Res ; 96(7): e11081, 2024 Jul.
Article de Anglais | MEDLINE | ID: mdl-39023047

RÉSUMÉ

Powdered activated carbon (PAC) has better adsorption performance than granular activated carbon (GAC) and is widely used in water purification. In most cases, PAC is dosed into water directly, then precipitated as sludge, and landfilled. In this study, PAC was mixed with a polymer and dissolved in dimethylformamide (DMF) solvent to form a PAC-loaded membrane, which was then tested for chloroform removal. The chloroform adsorption capacity of the PAC membrane increased with increasing membrane thickness because of higher carbon loading. However, regardless of membrane thickness, the flux of the PAC membranes was similar since flux resistance predominantly occurred at the top dense polymer surface. This dense surface can be removed by sandpaper polishing, where the adsorption capacity of the polished PAC membranes was 20% higher than the unpolished membranes because of more even distribution of feed water on the polished surface. Removal of the dense surface via polishing increased the flux by 97% to 130%, exceeding the flux of typical household carbon block filters. Using DMF to regenerate the membrane recovered 48% to 66% of the initial adsorption capacity. Thermal regeneration of the exhausted PAC membrane at 250°C was more effective than DMF regeneration (both in terms of cost and performance), with 83% to 94% PAC membrane regeneration efficiency over four regeneration recycles. After four thermal regeneration cycles, flux increased by 300% and the membrane became brittle because of thermal aging of the polymer, indicating that a total of 6 h of regeneration time (equivalent to three cycles in this study) was the limit for effective PAC membrane performance. PRACTITIONER POINTS: Powdered activated carbon was immobilized on a membrane to remove chloroform from water. Thicker membranes increased adsorption capacity but did not impact flux. Flux and capacity increased using polishing to remove the dense polymer surface and more evenly distribute flow across the membrane. Thermal regeneration of the membrane at 250°C was effective for up to three cycles and outperformed solvent-based regeneration. PAC-loaded filters are relevant for applications such as household carbon block filtration.


Sujet(s)
Charbon de bois , Chloroforme , Membrane artificielle , Polymères , Solvants , Polluants chimiques de l'eau , Purification de l'eau , Chloroforme/composition chimique , Purification de l'eau/méthodes , Charbon de bois/composition chimique , Solvants/composition chimique , Polymères/composition chimique , Polluants chimiques de l'eau/composition chimique , Adsorption
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