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1.
Int J Biol Macromol ; 268(Pt 2): 131942, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38685546

RESUMO

The interaction of monoglycerides and phytosterols in olive- and coconut oil on the structuring of oleogels was analyzed. Specifically, bigels with gelatin hydrogel in different ratios (40:60 and 60:40 w/w) were formed. The physicochemical and microstructural attributes of these systems were assessed. The olive oil to coconut oil ratio (0-100 w/w) and the added oleogelators affected the crystal structure and the mechanical properties of the oleogels. Polarized light microscopy revealed that the addition of coconut oil created a denser triglycerides crystal network and the presence of phytosterols created more needle-like crystals, enhancing the textural properties of the oleogels and of the resulting bigels. The hardness of the oleogels ranged from 0.50 N to 1.24 N and for bigels was 5.96-36.75 N. Bigels hardness decreased as the oleogel ratio in the bigel increased. Microscopy and FTIR revealed that the addition of coconut oil in oleogels hampered the formation of a distinct crystalline monoglycerides network. Also, the absence of new peaks in the bigels indicated that the two structured phases interact with each other mostly physically, without the formation of new chemical bonds. Consequently, the oleogels and bigels developed, comprise a promising hard fat substitute with improved nutritional profile.


Assuntos
Óleo de Coco , Azeite de Oliva , Compostos Orgânicos , Compostos Orgânicos/química , Óleo de Coco/química , Azeite de Oliva/química , Monoglicerídeos/química , Gelatina/química , Fenômenos Mecânicos , Triglicerídeos/química , Fitosteróis/química , Dureza , Espectroscopia de Infravermelho com Transformada de Fourier
2.
Ultrason Sonochem ; 102: 106729, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38103368

RESUMO

In this study, we compared the quality of iron walnut oil (IWO) oleogels prepared with different oleogelators, including γ-oryzanol/ß-sitosterol (OZ-PS), γ-oryzanol/triglyceride (OZ-TC), monoglycerides (MGS), beeswax (BW), beeswax-monoglycerides (BW-MGS), and carnauba wax (CW). The physicochemical and component properties, rheological and textural parameters, macroscopic morphologies, and antioxidant capacities of the resulting oleogels were analyzed. In addition, their microscopic properties were analyzed using Fourier-transform infrared (FTIR), X-ray powder diffraction (XRD) spectroscopy, and polarized light microscopy (PLM). The results showed that the gel structures produced by different oleogelators did not change the fatty acid composition of IWO. In addition, the IWO oleogel prepared with OZ-PS had a more stable network structure, excellent hardness at 4℃ (1116.51 g), better antioxidant capacity (766.50 µmol TE/kg) and higher total phenolic content (14.98 mg/kg) than any other experimental IWO oleogels. Moreover, comprehensive ranking by principal component analysis of numerous characteristics showed that the OZ-PS oleogel (2.533) ranked first among the six oleogels studied. Therefore, the IWO oleogel prepared with OZ-PS is a promising product, and our results provide guidance for the preparation of IWO oleogels, such as to increase their applications in the food industry.


Assuntos
Juglans , Monoglicerídeos , Fenilpropionatos , Monoglicerídeos/química , Antioxidantes , Compostos Orgânicos
3.
Food Chem ; 397: 133767, 2022 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-35905623

RESUMO

In this study, soybean oil-based oleogels were prepared using soy-protein isolate (SPI) and glycerol monolaurate (GML) in an emulsion-template approach. The rheological, texture, microstructure, and oil-retention properties of the obtained oleogels were analyzed. Results showed that the soy oil-based oleogel prepared with 6 wt% GML exhibited high oil loss, low-hardness, and needle-like morphology compared to the soy-oil/SPI-based oleogel. On the other hand, soy oil-based /SPI-based oleogels structured by 3 or 6 wt% GML presented moderate thermal-stability and lowest oil loss than those prepared without GML. Furthermore, SPI-based oleogel containing 6 wt% GML showed highest free fatty acids release (62.07%) with significantly improved elastic modulus and apparent viscosity. Additionally, the obtained oleogels displayed the occurrence of van der Waals interactions and intermolecular hydrogen bonds, presenting enhanced thermal stability. These results contribute to a better understanding of oleogelation-based emulsions for formulating trans-free and low-saturated foodstuffs with desired physical and functional properties.


Assuntos
Monoglicerídeos , Óleo de Soja , Emulsões/química , Lauratos , Monoglicerídeos/química , Compostos Orgânicos , Óleo de Soja/química , Proteínas de Soja/química
4.
Int J Biol Macromol ; 209(Pt A): 180-187, 2022 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-35395279

RESUMO

Edible double network oleogels were prepared by hydroxypropyl methylcellulose (HPMC) and glyceryl monostearate (GMS) by the cryogel-templated method. Hot GMS soybean oil solutions were absorbed by HPMC cryogels, which were further homogenized and cooled to form oleogels containing both the HPMC network and GMS network. The crystal network constructed by GMS crystal clusters significantly enhanced the mechanical and rheological attributes of oleogels. Both the HPMC network and the GMS network were built up due to hydrogen bonds. According to the normalization analysis of FTIR and the deepening of the shift of the absorption peak, hydrogen bonds could also be formed between HPMC and GMS to connect the two independent networks. Double network oleogels were further used to fabricate cookies and cakes, assessed by the texture profile analysis. The combination of the HPMC network and GMS network in preparing oleogels will promote the application of oleogels as the fat replacer.


Assuntos
Monoglicerídeos , Compostos Orgânicos , Derivados da Hipromelose/química , Monoglicerídeos/química , Compostos Orgânicos/química , Reologia
5.
Compr Rev Food Sci Food Saf ; 21(3): 2587-2614, 2022 05.
Artigo em Inglês | MEDLINE | ID: mdl-35279942

RESUMO

Monoglyceride (MG)-based oleogelation is an effective strategy to create soft matter structures with the functionality of fats, but with a nutritional profile similar to edible oils. MG oleogels are mainly studied to replace or reduce trans and saturated fats as well as to develop novel products with improved physical and organoleptic properties. The process consists of direct dispersion of MGs into the oil at temperatures above the melting point. This is followed by a cooling period in which the gelator network is formed, entrapping the oil in a crystalline structure. MG composition and concentration, oil type, process temperatures, stirring speed, shear rate during cooling, and storage time play a role in the kinetics of MG crystallization within an MG-oil system, which leads to the formation of lipid materials with different properties. A deep understanding of MG oleogelation processing parameters allows for the tailoring of oleogel properties to meet desirable characteristics as solid fat replacers. This review provides insight regarding manipulating physical process parameters to engineer structures with specific functionality. Furthermore, ultrasound technologies and optimization methodologies are discussed as tools for the production of oleogels with specific properties based on their potential use as well as the development of bi- and multi-gelators oleogels using MGs. Finally, the food applications in which MG oleogels have been tested are summarized in addition to the identified gaps that require further research.


Assuntos
Monoglicerídeos , Compostos Orgânicos , Cristalização , Monoglicerídeos/química , Compostos Orgânicos/química , Transição de Fase
6.
Food Res Int ; 154: 110997, 2022 04.
Artigo em Inglês | MEDLINE | ID: mdl-35337588

RESUMO

The use of multicomponent oleogels combined with a physical process such as high-intensity ultrasound (HIU) has become an interesting alternative to overcome nutritional and technological issues in fat-based foods. This is because the combination can add technological properties without changing the total amount of gelators, improving sensory acceptance and clean label claim. In this context, the study aims to evaluate the structuration power and physical properties of oleogels formed by monoglycerides (MG), fully hydrogenated rapessed oil (FHRO), and lecithin (LE) in rapeseed oil, with and without HIU. All samples were analyzed according to their microstructure, melting behavior, rheology, texture, polymorphism, and oil binding capacity. In mono-structured oleogels, only MG was able to form gels that did not flow. Three synergic combinations that produced 99% oil binding capacity oleogels were found: MG: FHRO, FHRO:LE, and MG:FHRO:LE. These combinations showed improved physical properties like hardness, elastic modulus, and oil loss when sonicated, which was attributed to the induced secondary crystallization of the FHRO promoted by HIU.


Assuntos
Monoglicerídeos , Compostos Orgânicos , Cristalização , Dureza , Monoglicerídeos/química , Compostos Orgânicos/química
7.
J Oleo Sci ; 70(8): 1059-1068, 2021 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-34248093

RESUMO

Vitamin C (VC)-loaded oleogel (VCOG) with corn oil and monoglyceride stearate was used to replace lipid phase of margarine completely. The oxidative stability of VCOG was evaluated at 60±1°C in a lightproof oven for 18 days and the result showed that VCOG peroxide (> 6 days) and p-anisidine value (> 4 days) was significantly lower than that of bulk oil and VC-free oleogel (p < 0.05). Then, the margarine containing 79.70% VCOG (VCOGM) was in comparison with four commercial butter in sensory and physical characteristic. Results showed that firmness, solid fat content and trans fatty acid of VCOGM were in the lowest values while unsaturated fatty acid and adhesiveness of VCOGM was in the highest values. Furthermore, VCOGM presented the similar springiness, cohesiveness, gumminess, score appearance, texture, taste and overall impression to some/all commercial butters selected in this research (p > 0.05). These results implied that VC-loaded oleogel was an excellent alternative of lipid phase in margarine which confirmed by 55% "definitely buy" and 25% "try once-then decide".


Assuntos
Ácido Ascórbico/química , Óleo de Milho/química , Ácidos Graxos Insaturados/química , Margarina , Monoglicerídeos/química , Estearatos/química , Manteiga , Comportamento do Consumidor , Ácidos Graxos Insaturados/análise , Humanos , Compostos Orgânicos/química , Oxirredução , Paladar , Triglicerídeos/análise , Triglicerídeos/química
8.
Molecules ; 26(11)2021 May 30.
Artigo em Inglês | MEDLINE | ID: mdl-34070869

RESUMO

Monoacylglycerol lipase (MAGL) is a key enzyme in the human endocannabinoid system. It is also the main enzyme responsible for the conversion of 2-arachidonoyl glycerol (2-AG) to arachidonic acid (AA), a precursor of prostaglandin synthesis. The inhibition of MAGL activity would be beneficial for the treatment of a wide range of diseases, such as inflammation, neurodegeneration, metabolic disorders and cancer. Here, the author reports the pharmacological evaluation of new disulfiram derivatives as potent inhibitors of MAGL. These analogues displayed high inhibition selectivity over fatty acid amide hydrolase (FAAH), another endocannabinoid-hydrolyzing enzyme. In particular, compound 2i inhibited MAGL in the low micromolar range. However, it did not show any inhibitory activity against FAAH.


Assuntos
Dissulfiram/farmacologia , Monoacilglicerol Lipases/antagonistas & inibidores , Monoacilglicerol Lipases/química , Amidoidrolases/química , Ácidos Araquidônicos/química , Carbamatos/farmacologia , Dissulfiram/análogos & derivados , Endocanabinoides/química , Endocanabinoides/metabolismo , Inibidores Enzimáticos/farmacologia , Glicerídeos/química , Humanos , Hidrólise , Monoglicerídeos/química , Relação Estrutura-Atividade
9.
Methods Mol Biol ; 2306: 77-91, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33954941

RESUMO

Phospholipids play important roles in biological process even at a very low level. For example, bis(monoacylglycerol)phosphate (BMP) is involved in the pathogenesis of lysosomal storage diseases, and polyphosphoinositides (PPI) play critical roles in cellular signaling and functions. Phosphatidylglycerol (PG), a structural isomer of BMP, mediates lipid-protein and lipid-lipid interactions, and inhibits platelet activating factor and phosphatidylcholine transferring. However, due to their low abundance, the analysis of these phospholipids from biological samples is technically challenging. Therefore, the cellular function and metabolism of these phospholipids are still elusive. This chapter overviews a novel method of shotgun lipidomics after methylation with trimethylsilyl-diazomethane (TMS-D) for accurate and comprehensive analysis of these phospholipid species in biological samples. Firstly, a modified Bligh and Dyer procedure is performed to extract tissue lipids for PPI analysis, whereas modified methyl-tert-butylether (MTBE) extraction and modified Folch extraction methods are described to extract tissue lipids for PPI analysis. Secondly, TMS-D methylation is performed to derivatize PG/BMP and PPI, respectively. Then, we described the shotgun lipidomics strategies that can be used as cost-effective and relatively high-throughput methods to determine BMP, PG, and PPI species and isomers with different phosphate position(s) and fatty acyl chains. The described method of shotgun lipidomics after methylation achieves feasible and reliable quantitative analysis of low-abundance lipid classes. The application of this novel method should enable us to reveal the metabolism and functions of these phospholipids in healthy and disease states.


Assuntos
Lipidômica/métodos , Lisofosfolipídeos/análise , Monoglicerídeos/análise , Fosfatidilgliceróis/análise , Fosfatos de Fosfatidilinositol/análise , Animais , Diazometano/análogos & derivados , Diazometano/química , Ensaios de Triagem em Larga Escala , Humanos , Isomerismo , Lisofosfolipídeos/química , Metilação , Camundongos , Monoglicerídeos/química , Fosfatidilgliceróis/química , Fosfatos de Fosfatidilinositol/química , Espectrometria de Massas por Ionização por Electrospray , Compostos de Trimetilsilil/química
10.
J Mater Sci Mater Med ; 32(4): 39, 2021 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-33792773

RESUMO

Biomaterials used in tissue regeneration processes represent a promising option for the versatility of its physical and chemical characteristics, allowing for assisting or speeding up the repair process stages. This research has characterized a polyurethane produced from castor oil monoacylglyceride (Ricinus communis L) and tested its effect on reconstructing bone defects in rat calvaria, comparing it with commercial castor oil polyurethane. The characterizations of the synthesized polyurethane have been performed by spectroscopy in the infrared region with Fourier transform (FTIR); thermogravimetric analysis (TG/DTG); X-ray diffraction (XRD) and Scanning Electron Microscopy (SEM). For the in vivo test, 24 animals have been used, divided into 3 groups: untreated group (UG); control group treated with Poliquil® castor polyurethane (PCP) and another group treated with castor polyurethane from the Federal University of Piauí - UFPI (CPU). Sixteen weeks after surgery, samples of the defects were collected for histological and histomorphometric analysis. FTIR analysis has shown the formation of monoacylglyceride and polyurethane. TG and DTG have indicated thermal stability of around 125 °C. XRD has determined the semi-crystallinity of the material. The polyurethane SEM has shown a smooth morphology with areas of recesses. Histological and histomorphometric analyzes have indicated that neither CPU nor PCP induced a significant inflammatory process, and CPU has shown, statistically, better performance in bone formation. The data obtained shows that CPU can be used in the future for bone reconstruction in the medical field.


Assuntos
Fraturas Ósseas/cirurgia , Monoglicerídeos/química , Poliuretanos/química , Ricinus/química , Animais , Materiais Biocompatíveis/química , Regeneração Óssea/efeitos dos fármacos , Substitutos Ósseos/farmacologia , Osso e Ossos/metabolismo , Óleo de Rícino/química , Consolidação da Fratura , Inflamação , Masculino , Teste de Materiais , Microscopia Eletrônica de Varredura , Osteogênese/efeitos dos fármacos , Ratos , Espectroscopia de Infravermelho com Transformada de Fourier , Temperatura , Difração de Raios X
11.
Appl Biochem Biotechnol ; 193(9): 2781-2792, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-33871767

RESUMO

Here, we developed an efficient strategy for the production of lauric acid-enriched monoacylglycerol (MAG) via enzymatic glycerolysis using black soldier fly (Hermetia illucens) larvae (BSFL) oil. The effects of the substrate molar ratio, reaction temperature, type of immobilized lipase, and organic solvent on the MAG content and conversion degree of BSFL oil were optimized. The maximum substrate conversion rate (97.88%) and MAG content (70.84%) were obtained in a tert-butanol system at 50 °C with a glycerol/BSFL oil molar ratio of 4:1 by using immobilized MAS1 lipase as a catalyst. The MAG content in the purified product reached 97.7%, with lauric acid accounting for 50.2%. Improved oxidation stability was observed after glycerolysis. Overall, this study provides a new strategy for the preparation of lauric acid-enriched MAG from BSFL oil.


Assuntos
Misturas Complexas/química , Dípteros/química , Proteínas de Insetos/química , Ácidos Láuricos/química , Lipase/química , Monoglicerídeos/síntese química , Animais , Larva/química , Monoglicerídeos/química
12.
Food Chem ; 356: 129667, 2021 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-33831829

RESUMO

In this paper, different types of oleogels were prepared by five gelators including hydroxypropyl methyl cellulose (HPMC), monoacylglycerol (MAG), sodium stearyl lactate (SSL), rice bran wax (RBW) and beeswax (BW), and their applications in cookies were compared. Texture, microstructure, and colour results showed that MAG, RBW and shortening based cookies had similar hardness, porous structure, and L*, a*, b*. MAG and RBW exhibited excellent rheological properties similar to shortening. Regarding the consumer sensory evaluation of cookies, RBW, MAG and shortening had similar scores of 3.9, 4.3 and 4.1, respectively. For wax-based oleogels, the higher the content of ß' crystal and solid fat content (SFC), the lower the hardness of cookies, but the cookies hardness of emulsifier based oleogels do not depend on ß' content and SFC. This paper confirmed the best gelators for cookies, and provided a reference for developing the oleogels to match the quality of shortening in cookies.


Assuntos
Doces/análise , Varredura Diferencial de Calorimetria , Culinária/métodos , Dureza , Derivados da Hipromelose/química , Monoglicerídeos/química , Compostos Orgânicos/química , Reologia , Estearatos/química , Ceras/química
13.
Food Chem ; 354: 129534, 2021 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-33752116

RESUMO

The effect of using highly unsaturated 2-monoglycerides as oleogelators on the properties of soybean oil oleogels designed to eliminate saturated and trans fatty acids was investigated in this study. We adopted a novel two-step synthesis aiming to increase the yield of the 2-monoglycerides. The optimal synthesis conditions were a substrate weight ratio of 2:1 (w/w), 10% Lipozyme 435 (w/w total reactants), and 4 h of reaction time at room temperature. Under these conditions, the 2-monoglyceride yield (40.69%) increased by 10% compared to that of the conventional synthesis route. Additionally, soybean oil oleogels prepared using 10% 2-monoglycerides with or without rice bran wax were systematically characterized by polarized light microscopy, a texture analyzer, XRD spectroscopy, and rheometry. Comparative studies indicated that a combination of rice bran wax and 2-monoglycerides had synergistic effects on gel properties. A mixture of 4% rice bran wax and 6% 2-monoglycerides was found to provide better oleogels.


Assuntos
Ácidos Graxos Insaturados/química , Monoglicerídeos/química , Isomerismo , Compostos Orgânicos/química , Óleo de Soja/química
14.
J Food Sci ; 86(2): 343-356, 2021 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-33448022

RESUMO

Oleogels and oleogelation routes have been extensively studied in the past decade; however, the industry has not yet implemented this technique due to price, availability, and clean label. The objective of this study was to evaluate the synergism of binary oleogels structured by monoglycerides (MG) and high melting point triacylglycerols (HF) with and without high-intensity ultrasound (HIU) according to their physical properties. MG:HF (0:6, 1:5, 2:4, 3:3, 4:2, 5:1, and 6:0) oleogels were produced by mixing at 70 °C with a stirring of 350 rpm for 5 min, followed by a cooling and storage at 20 °C for 24 hr. A 20-kHz HIU was applied for 10s, 30s, or 10s using three pulses (10sON/10sOFF) during the cooling step via a macro tip (12.7 mm) and 50% amplitude (56 W) in the presence of few -crystals. Samples were evaluated according to their hardness, oil-binding capacity (OBC), microstructure, melting behavior, viscoelasticity, and flow behavior. The best physical properties were found in the MG6:HF0 oleogel, with a hardness of 1.2 N, elasticity of 5.5 kPa, viscosity of 99 Pa⋅s and 99% OBC. These properties were reduced with the decrease of MG in the blend. The sonication did not improve the MG6:HF0, instead it affected its properties negatively. However, sonication showed a positive effect on the blends of MG and HF. The hardness was improved at least threefold and OBC around 20%, these effects were already observed using only 10s sonication. Sonocrystallization induced secondary nucleation and changed the crystalline material only in blends containing HF indicating the better effect of the sonocrystallization on oleogels in the presence of high-melting points triacylglycerols. PRACTICAL APPLICATION: Oleogels are a valuable alternative in food industry to replace trans and reduce saturated fatty acids content in many food products. The combination of a binary structuration and use of high-intensity ultrasound that is a physical green technology will give the food industry information on how to improve the physical properties of oleogels without increasing the amount of oleogelators, giving a future alternative to clean label and sensory claims of oleogels applications.


Assuntos
Tecnologia de Alimentos/métodos , Monoglicerídeos/química , Sonicação/métodos , Triglicerídeos/química , Cristalização , Elasticidade , Ácidos Graxos/química , Dureza , Compostos Orgânicos/química , Transição de Fase , Temperatura de Transição , Viscosidade
15.
Sci Rep ; 10(1): 19305, 2020 11 09.
Artigo em Inglês | MEDLINE | ID: mdl-33168855

RESUMO

In meso crystallization of membrane proteins relies on the use of lipids capable of forming a lipidic cubic phase (LCP). However, almost all previous crystallization trials have used monoacylglycerols, with 1-(cis-9-octadecanoyl)-rac-glycerol (MO) being the most widely used lipid. We now report that EROCOC17+4 mixed with 10% (w/w) cholesterol (Fig. 1) serves as a new matrix for crystallization and a crystal delivery medium in the serial femtosecond crystallography of Adenosine A2A receptor (A2AR). The structures of EROCOC17+4-matrix grown A2AR crystals were determined at 2.0 Å resolution by serial synchrotron rotation crystallography at a cryogenic temperature, and at 1.8 Å by LCP-serial femtosecond crystallography, using an X-ray free-electron laser at 4 and 20 °C sample temperatures, and are comparable to the structure of the MO-matrix grown A2AR crystal (PDB ID: 4EIY). Moreover, X-ray scattering measurements indicated that the EROCOC17+4/water system did not form the crystalline LC phase at least down to - 20 °C, in marked contrast to the equilibrium MO/water system, which transforms into the crystalline LC phase below about 17 °C. As the LC phase formation within the LCP-matrix causes difficulties in protein crystallography experiments in meso, this feature of EROCOC17+4 will expand the utility of the in meso method.


Assuntos
Cristalografia por Raios X/instrumentação , Lipídeos/química , Monoglicerídeos/química , Terpenos/química , Animais , Colesterol/química , Cristalização , Escherichia coli , Proteínas de Membrana/química , Receptores A2 de Adenosina/química , Células Sf9 , Spodoptera , Síncrotrons , Temperatura , Raios X
16.
BMC Res Notes ; 13(1): 527, 2020 Nov 11.
Artigo em Inglês | MEDLINE | ID: mdl-33176880

RESUMO

OBJECTIVES: The aim of this study was to use Ligand-based pharmacophore modelling approach for four established antiviral drugs, namely remdesivir, lopinavir, ritonavir and hydroxychloroquine for COVID-19 inhibitors as training sets. In this study Twenty vanillin derivatives together with monolaurin and tetrodotoxin were used as test sets to evaluate as potential SARS-CoV-2 inhibitors. The Structure-based pharmacophore modelling approach was also performed using 5RE6, 5REX and 5RFZ in order to analyse the binding site and ligand-protein complex interactions. RESULTS: The pharmacophore modelling mode of 5RE6 displayed two Hydrogen Bond Acceptors (HBA) and one Hydrophobic (HY) interaction. Besides, the pharmacophore model of 5REX showed two HBA and two HY interactions. Finally, the pharmacophore model of 5RFZ showed three HBA and one HY interaction. Based on ligand-based approach, 20 Schiff-based vanillin derivatives, showed strong MPro inhibition activity. This was due to their good alignment and common features to PDB-5RE6. Similarly, monolaurin and tetrodotoxin displayed some significant activity against SARS-CoV-2. From structure-based approach, vanillin derivatives (1) to (12) displayed some potent MPro inhibition against SARS-CoV-2. Favipiravir, chloroquine and hydroxychloroquine also showed some significant MPro inhibition.


Assuntos
Antivirais/farmacologia , Betacoronavirus/efeitos dos fármacos , Cloroquina/farmacologia , Inibidores de Cisteína Proteinase/farmacologia , Proteínas não Estruturais Virais/antagonistas & inibidores , Amidas/química , Amidas/farmacologia , Antivirais/química , Benzaldeídos/química , Cloroquina/química , Simulação por Computador , Proteases 3C de Coronavírus , Cisteína Endopeptidases , Inibidores de Cisteína Proteinase/química , Humanos , Hidroxicloroquina/química , Hidroxicloroquina/farmacologia , Lauratos/química , Lauratos/farmacologia , Testes de Sensibilidade Microbiana , Modelos Moleculares , Monoglicerídeos/química , Monoglicerídeos/farmacologia , Pirazinas/química , Pirazinas/farmacologia , SARS-CoV-2 , Relação Estrutura-Atividade , Tetrodotoxina/química , Tetrodotoxina/farmacologia
17.
Biochimie ; 178: 26-38, 2020 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-32659447

RESUMO

Bis(monoacylglycero)phosphate (BMP), also known as lysobisphosphatidic acid (LBPA), is a phospholipid specifically enriched in the late endosome-lysosome compartment playing a crucial role for the fate of endocytosed components. Due to its presence in extracellular fluids during diseases associated with endolysosomal dysfunction, it is considered as a possible biomarker of disorders such as genetic lysosomal storage diseases and cationic amphiphilic drug-induced phospholipidosis. However, there is no true validation of this biomarker in human studies, nor a clear identification of the carrier of this endolysosome-specific lipid in biofluids. The present study demonstrates that in absence of any sign of renal failure, BMP, especially all docosahexaenoyl containing species, are significantly increased in the urine of patients treated with the antiarrhythmic drug amiodarone. Such urinary BMP increase could reflect a generalized drug-induced perturbation of the endolysosome compartment as observed in vitro with amiodarone-treated human macrophages. Noteworthy, BMP was associated with extracellular vesicles (EVs) isolated from human urines and extracellular medium of human embryonic kidney HEK293 cells and co-localizing with classical EV protein markers CD63 and ALIX. In the context of drug-induced endolysosomal dysfunction, increased BMP-rich EV release could be useful to remove excess of undigested material. This first human pilot study not only reveals BMP as a urinary biomarker of amiodarone-induced endolysosomal dysfunction, but also highlights its utility to prove the endosomal origin of EVs, also named as exosomes. This peculiar lipid already known as a canonical late endosome-lysosome marker, may be thus considered as a new lipid marker of urinary exosomes.


Assuntos
Endossomos/química , Endossomos/metabolismo , Vesículas Extracelulares/química , Vesículas Extracelulares/metabolismo , Lisofosfolipídeos/metabolismo , Monoglicerídeos/metabolismo , Idoso , Amiodarona/efeitos adversos , Animais , Antiarrítmicos/efeitos adversos , Biomarcadores/urina , Endossomos/efeitos dos fármacos , Vesículas Extracelulares/efeitos dos fármacos , Feminino , Células HEK293 , Humanos , Nefropatias/induzido quimicamente , Lisofosfolipídeos/química , Lisossomos/efeitos dos fármacos , Lisossomos/metabolismo , Macrófagos/química , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Masculino , Pessoa de Meia-Idade , Monoglicerídeos/química , Projetos Piloto , Ratos , Células THP-1
18.
Food Funct ; 11(3): 2498-2508, 2020 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-32134421

RESUMO

The objective of this research was to fabricate crude soybean oil oleogels (CSO) using ß-sitosterol (BS) and/or monoacylglycerol (MAG) and compare their role with that of refined soybean oil oleogels (RSO) in cookie making. Both crude and refined soybean oil oleogels were formed with BS or MAG, or the combination of both (1 : 1) at a fixed concentration of 10 wt%. The thermal behavior of the oleogels was measured using differential scanning calorimetry (DSC). The crystal structure and morphology of the oleogels were characterized using X-ray diffraction (XRD) and polarized light microscopy (PLM). The hardness of the oleogel and commercial vegetable shortening was compared using a texture analyzer. The characteristics of cookies made with the oleogels were compared with those of cookies made with commercial vegetable shortening. Overall, the incorporation of BS and/or MAG into crude and refined soybean oil can produce oleogels with solid-like properties. Refined soybean oil formed stronger and firmer oleogels as compared to crude soybean oil. RSO structured by BS presented branched fiber-like, elongated plate-like, and needle-like crystals while the same oil gelled by MAG contained spherulite crystals. RSO made with the combination of BS and MAG displayed crystal morphologies from both BS and MAG. The same crystal morphologies were observed in CSO with lower quantities. Comparing the quality of cookies made with the oleogels and commercial vegetable shortening, equal or better performance of both RSO and CSO in terms of weight, thickness, width, spread ratio, and hardness of cookies than that of commercial vegetable shortening was observed. By combining the results of the physical characterization and cookie making performance, it can be concluded that both crude and refined soybean oleogels could resemble commercial shortening, which offers the possibility of using oleogels to replace shortening in the baking industry.


Assuntos
Culinária , Monoglicerídeos/química , Sitosteroides/química , Óleo de Soja/química , Compostos Orgânicos/química
19.
Int J Mol Sci ; 21(4)2020 Feb 20.
Artigo em Inglês | MEDLINE | ID: mdl-32093358

RESUMO

In this work, we developed a solid lipid nanoparticle (SLN) formulation with (+)-limonene 1,2-epoxide and glycerol monostearate (Lim-SLNs), stabilized with Poloxamer® 188 in aqueous dispersion to modify the release profile of the loaded monoterpene derivative. We also evaluated the role of SLNs in lipid peroxidation and cytotoxicity in a spontaneously transformed aneuploid immortal keratinocyte cell line from adult human skin (the HaCaT cell line). For the cell viability assay, the colorimetric 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay was used. Lim-SLNs with a loading capacity and encapsulation efficiency of 0.39% and 63%, respectively, were produced by high pressure homogenization. A mean particle size of 194 ± 3.4 nm and polydispersity index of 0.244 were recorded for the loaded Lim-SLNs, as compared to 203 ± 1.5 nm (PI 0.213) for the non-loaded (blank) SLNs. The loading of the monoterpene derivative into glycerol monostearate SLNs fitted into the zero-order kinetics, and ameliorated both lipid peroxidation and cytotoxicity in a keratinocyte cell line. A promising formulation for antioxidant and anti-tumoral activities is here proposed.


Assuntos
Antioxidantes , Monoterpenos Cicloexânicos , Queratinócitos/metabolismo , Peroxidação de Lipídeos/efeitos dos fármacos , Monoglicerídeos , Nanopartículas/química , Poloxâmero , Antioxidantes/química , Antioxidantes/farmacocinética , Antioxidantes/farmacologia , Linhagem Celular , Monoterpenos Cicloexânicos/química , Monoterpenos Cicloexânicos/farmacocinética , Monoterpenos Cicloexânicos/farmacologia , Preparações de Ação Retardada/química , Preparações de Ação Retardada/farmacocinética , Preparações de Ação Retardada/farmacologia , Humanos , Monoglicerídeos/química , Monoglicerídeos/farmacocinética , Monoglicerídeos/farmacologia , Poloxâmero/química , Poloxâmero/farmacocinética , Poloxâmero/farmacologia
20.
Food Chem ; 314: 126146, 2020 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-31954944

RESUMO

Sunflower oil enriched with curcuminoid compounds (CUs) was gelled by adding 5% (w/w) saturated monoglycerides (MG), rice bran waxes (RW) or a mixture of ß-sitosterol and γ-oryzanol (PS). The resulting oleogels differed for rheological properties and firmness due to the difference in gel network structure. PS oleogel was the firmest sample followed by RW and MG ones. Upon in vitro digestion, fatty acid release as a function of digestion time was greatly affected by oleogel structure: the extent of lipolysis decreased as oleogel strength increased (PS < RW < MG). On the other hand, the nature of the oleogelator affected CUs bioaccessibility, which was lower in oleogels containing crystalline particles (MG and RW). These findings appear interesting in the attempt to develop oleogels able to control lipid digestion as well as to deliver bioactive molecules in food systems.


Assuntos
Diarileptanoides/farmacocinética , Lipólise , Óleo de Girassol/farmacocinética , Disponibilidade Biológica , Diarileptanoides/química , Digestão , Ácidos Graxos/farmacocinética , Humanos , Monoglicerídeos/química , Compostos Orgânicos/química , Compostos Orgânicos/farmacocinética , Tamanho da Partícula , Fenilpropionatos/química , Reologia , Sitosteroides/química , Óleo de Girassol/química
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