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1.
J Agric Food Chem ; 68(1): 426-438, 2020 Jan 08.
Artigo em Inglês | MEDLINE | ID: mdl-31855429

RESUMO

Modern peanut contains fatty acid desaturase 2 (FAD2) mutation, which is capable of producing high oleic acid for human health. However, the dynamic changes of the lipidome regarding fad2 remain elusive in peanut seed. In the present study, 547 lipid features were identified in high- and normal-oleic peanut seeds by utilizing the mass spectrometric approach. The fad2-induced differently expressed lipids (DELs) were polarly distributed at early and maturation stages during high-oleic acid (OA) seed development. Subsequently, integration of previously published proteomic data and lipidomic data revealed that 21 proteins and 149 DELs were annotated into the triacylglycerol assembly map, of which nine enzymes and 31 lipid species shared similar variation tendencies. Additionally, the variation tendencies of 17 acyl fatty acids were described in a hypothetical biosynthetic pathway. Collectively, the understanding of the lipid composition correlated with fad2 established a foundation for future high-OA peanut breeding based on lipidomic data.


Assuntos
Arachis/química , Lipídeos/química , Ácido Oleico/química , Proteínas de Plantas/química , Arachis/genética , Arachis/crescimento & desenvolvimento , Arachis/metabolismo , Ácidos Graxos Dessaturases/genética , Ácidos Graxos Dessaturases/metabolismo , Metabolismo dos Lipídeos , Mutação , Ácido Oleico/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Proteômica , Sementes/química , Sementes/genética , Sementes/crescimento & desenvolvimento , Sementes/metabolismo
2.
Soft Matter ; 15(44): 9011-9017, 2019 Nov 28.
Artigo em Inglês | MEDLINE | ID: mdl-31687734

RESUMO

A kind of lyotropic liquid crystal nanoparticle (LLC NPs) has been designed and prepared. LLC NPs are dSMO/OA/ß-casein/water quaternary systems, and their cubic or hexagonal microstructures have been characterized by cryogenic transmission electron microscopy (cryo-TEM) and small angle X-ray scattering (SAXS). The phase transition of LLC NPs takes place with ratio and pH adjustments. The properties, such as cytotoxicity, stability, drug encapsulation and release ability, have been investigated with MTT assay, cryo-TEM and UV-Vis spectroscopy. The results showed that LLC NPs were nontoxic to cells and stable to enzymatic degradation. Hydrophilic drug doxorubicin hydrochloride (DOX·HCl) could be effectively encapsulated in LLC NPs and its release rate could be regulated by pH. It was concluded that LLC NPs are potential nanocarriers in nanomedicine technologies. We hope that this work provides new guidelines for the rational design of LLC NP systems with lipopeptides for biomedical applications.


Assuntos
Caseínas/química , Doxorrubicina/química , Portadores de Fármacos/química , Lipopeptídeos/química , Cristais Líquidos/química , Nanopartículas/química , Sobrevivência Celular , Doxorrubicina/farmacologia , Liberação Controlada de Fármacos , Estabilidade de Medicamentos , Células HEK293 , Células HeLa , Humanos , Concentração de Íons de Hidrogênio , Interações Hidrofóbicas e Hidrofílicas , Ácido Oleico/química , Transição de Fase
3.
J Oleo Sci ; 68(11): 1149-1155, 2019 Nov 07.
Artigo em Inglês | MEDLINE | ID: mdl-31611519

RESUMO

The absorption efficacies and catabolic rates of fatty acids are affected by their binding position on triacylglycerol (TAG). However, the kind of effect calcium treatment has on the catabolism of fatty acids is unclear. In this study, the catabolic rates of 13C-labeled palmitic acid, oleic acid, and linoleic acid bound to sn-1, 3 (α) and sn-2 (ß) position of TAG in the presence of calcium were compared using isotope ratio mass spectrometry. The catabolic rates of 13C-labeled fatty acids were evaluated using the ratio of 13C to 12C in the carbon dioxide expired by mice. The catabolic rate of palmitic acid bound to the α position was significantly lower than that of palmitic acid bound to the ß position of TAG. The rates of 13CO2 formation from palmitic acid at the ß position remained higher for a long time. In contrast, oleic and linoleic acids at the α position were as well catabolized as those at the ß position. These results indicate that in the presence of calcium, the saturated fatty acid bound to the ß position is highly catabolized, whereas that bound to the α position is not well catabolized. Saturated fatty acid at the α position is hydrolyzed by pancreatic lipase to promptly form insoluble complexes with calcium, which are excreted from the body, and thereby reducing the catabolic rate of these fatty acids.


Assuntos
Cálcio/farmacologia , Ácidos Graxos/química , Ácidos Graxos/metabolismo , Triglicerídeos/metabolismo , Animais , Sítios de Ligação , Cálcio/administração & dosagem , Dióxido de Carbono/metabolismo , Isótopos de Carbono , Marcação por Isótopo , Ácido Linoleico/química , Ácido Linoleico/metabolismo , Masculino , Camundongos Endogâmicos , Ácido Oleico/química , Ácido Oleico/metabolismo , Ácido Palmítico/química , Ácido Palmítico/metabolismo
4.
J Agric Food Chem ; 67(43): 12072-12083, 2019 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-31577433

RESUMO

Phytostanyl fatty acid esters, which are being added to a variety of foods owing to their cholesterol-lowering properties, are susceptible to thermally induced oxidation reactions. Using sitostanyl oleate as an example, we, in this study, aimed at developing strategies for the detection and the quantitation of acyl chain oxidation products (ACOPs). The elaborated ultra high performance liquid chromatography-mass spectrometry MS/MS-based approach involves (i) derivatizations of hydroxy and oxo groups, (ii) combined use of atmospheric pressure chemical ionization and electrospray ionization as ionization techniques, and (iii) establishment of selective multireaction monitoring transitions. These strategies allow the identification of a broad spectrum of nonpolar short-chain as well as polar short- and long-chain hydroxy, epoxy, and oxo ACOPs. Semiquantitative assessments showed that sitostanyl 9,10-epoxystearate was the predominating ACOP resulting from thermo-oxidation of sitostanyl oleate at 180 °C for 30 min. The elaborated analytical approach paves the way to narrow the existing knowledge gap on the fate of phytostanyl fatty acid esters upon heat treatments.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Ácido Oleico/química , Espectrometria de Massas em Tandem/métodos , Temperatura Alta , Estrutura Molecular , Oxirredução
5.
Chemistry ; 25(69): 15863-15870, 2019 Dec 10.
Artigo em Inglês | MEDLINE | ID: mdl-31596001

RESUMO

Sustainability in chemistry heavily relies on heterogeneous catalysis. Enzymes, the main catalyst for biochemical reactions in nature, are an elegant choice to catalyze reactions due to their high activity and selectivity, although they usually suffer from lack of robustness. To overcome this drawback, enzyme-decorated nanoporous heterogeneous catalysts were developed. Three different approaches for Candida antarctica lipase B (CAL-B) immobilization on a covalent organic framework (PPF-2) were employed: physical adsorption on the surface, covalent attachment of the enzyme in functional groups on the surface and covalent attachment into a linker added post-synthesis. The influence of the immobilization strategy on the enzyme uptake, specific activity, thermal stability, and the possibility of its use through multiple cycles was explored. High specific activities were observed for PPF-2-supported CAL-B in the esterification of oleic acid with ethanol, ranging from 58 to 283 U mg-1 , which was 2.6 to 12.7 times greater than the observed for the commercial Novozyme 435.


Assuntos
Enzimas Imobilizadas/química , Proteínas Fúngicas/química , Lipase/química , Estruturas Metalorgânicas/química , Adsorção , Biocatálise , Candida/enzimologia , Esterificação , Modelos Moleculares , Nanoporos/ultraestrutura , Ácido Oleico/química
6.
Int J Nanomedicine ; 14: 6539-6553, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31496699

RESUMO

Aim: This paper reports on the incorporation of oleic acid (OA) within nanostructured lipid carriers (OA-NLC) to improve the anti-inflammatory effects in the presence of albumin. Materials and methods: NLCs produced via hot high-shear homogenization/ultrasonication were characterized in terms of particle size, zeta potential, and toxicity. We examined the effects of OA-NLC on neutrophil activities. Dermatologic therapeutic potential was also elucidated by using a murine model of leukotriene B4-induced skin inflammation. Results: In the presence of albumin, OA-NLC but not free OA inhibited superoxide generation and elastase release. Topical administration of OA-NLC alleviated neutrophil infiltration and severity of skin inflammation. Conclusion: OA incorporated within NLC can overcome the interference of albumin, which would undermine the anti-inflammatory effects of OA. OA-NLC has potential therapeutic effects in topical ointments.


Assuntos
Portadores de Fármacos/química , Inflamação/patologia , Lipídeos/química , Nanoestruturas/química , Neutrófilos/fisiologia , Ácido Oleico/química , Soroalbumina Bovina/farmacologia , Pele/patologia , Administração Tópica , Adulto , Animais , Cálcio/metabolismo , Bovinos , Morte Celular/efeitos dos fármacos , Portadores de Fármacos/administração & dosagem , Humanos , Leucotrieno B4 , Lipídeos/toxicidade , Masculino , Camundongos Endogâmicos BALB C , Nanoestruturas/administração & dosagem , Nanoestruturas/toxicidade , Nanoestruturas/ultraestrutura , Ativação de Neutrófilo/efeitos dos fármacos , Neutrófilos/efeitos dos fármacos , Ácido Oleico/toxicidade , Elastase Pancreática/metabolismo , Superóxidos/metabolismo , Adulto Jovem
7.
Mar Drugs ; 17(9)2019 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-31480614

RESUMO

Chitosan oleate (CS-OA), a chitosan salt with amphiphilic properties, has demonstrated the ability to self-assemble in aqueous environment to give polymeric micelles useful to load poorly soluble drugs. More recently, CS-OA was proposed to stabilize nanoemulsions during the preparation by emulsification and solvent evaporation of poly lactic-glycolic acid (PLGA) nanoparticles (NPs) loaded with curcumin. Positive mucoadhesive behavior and internalization properties were demonstrated for these NPs attributable to the presence of positive charge at the NP surface. In the present paper, two CS-OA-based nanosystems, micelles and PLGA NPs, were compared with the aim of elucidating their physico-chemical characteristics, and especially their interaction with cell substrates. The two systems were loaded with resveratrol (RSV), a hydrophobic polyphenol endowed with anti-cancerogenic, anti-inflammatory, and heart/brain protective effects, but with low bioavailability mainly due to poor aqueous solubility. Calorimetric analysis and X-ray spectra demonstrated amorphization of RSV, confirming its affinity for hydrophobic domains of polymeric micelles and PLGA core of NPs. TGA decomposition patterns suggest higher stability of PLGA-NPs compared with polymeric micelles, that anyway resulted more stable than expected, considering the RSV release profiles, and the cell line interaction results.


Assuntos
Quitosana/química , Glicolatos/química , Nanopartículas/química , Ácido Oleico/química , Copolímero de Ácido Poliláctico e Ácido Poliglicólico/química , Polímeros/química , Resveratrol/química , Disponibilidade Biológica , Células CACO-2 , Linhagem Celular Tumoral , Curcumina/química , Portadores de Fármacos/química , Sistemas de Liberação de Medicamentos/métodos , Glicóis/química , Células HeLa , Humanos , Interações Hidrofóbicas e Hidrofílicas , Micelas , Tamanho da Partícula , Solubilidade/efeitos dos fármacos , Propriedades de Superfície
8.
J Dairy Sci ; 102(11): 9749-9762, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31495617

RESUMO

One of the main challenges in the food industry is to design strategies for the successful incorporation of natural sources of bioactive compounds. Recently, yogurts and other fermented dairy beverages have been proposed as ideal carriers of such bioactive compounds such as fatty acids and antioxidants that could improve consumers' health. However, the incorporation of new ingredients causes functional and structural modifications that may affect the consumers' preferences. In this work, a dairy beverage model supplemented with oleic acid has been designed by partial substitution of milk by Candida utilis single-cell protein extract. The changes in the structural properties of this new beverage were evaluated by following the fermentation process, pH, aggregate size, microstructure, and changes in rheological properties. Furthermore, molecular dynamics simulations were carried out to analyze the interaction between its main components. Our data revealed that samples with a percentage of milk substitution of 30% showed a higher viscosity as compared with the other percentages and less viscosity than the control (no substitution). These samples were then selected for fortification by incorporating oleic acid microcapsules. A concentration of 1.5 g/100 g was shown to be the optimal quantity of microcapsules for oleic acid supplementation. Molecular dynamic simulations revealed glutathione as an important component of the micro-gel structure. The present study forms the basis for novel studies where Candida utilis single-cell protein and microencapsulated essential oils could be used to design innovative bioproducts.


Assuntos
Bebidas/análise , Candida/química , Proteínas na Dieta/química , Ácido Oleico/química , Animais , Antioxidantes/análise , Suplementos Nutricionais , Ácidos Graxos/análise , Fermentação , Glutationa/metabolismo , Concentração de Íons de Hidrogênio , Leite/química , Óleos Voláteis/química , Reologia , Viscosidade
9.
Molecules ; 24(17)2019 Aug 29.
Artigo em Inglês | MEDLINE | ID: mdl-31470517

RESUMO

Global incidence of superficial fungal infections caused by dermatophytes is high and affects around 40 million people. It is the fourth most common cause of infection. Clotrimazole, a broad spectrum imidazole antifungal agent is widely used to treat fungal infections. Conventional topical formulations of clotrimazole are intended to treat infections by effective penetration of drugs into the stratum corneum. However, drawbacks such as poor dermal bioavailability, poor penetration, and variable drug levels limit the efficiency. The present study aims to load clotrimazole into ufosomes and evaluate its topical bioavailability. Clotrimazole loaded ufosomes were prepared using cholesterol and sodium oleate by thin film hydration technique and evaluated for size, polydispersity index, and entrapment efficiency to obtain optimized formulation. Optimized formulation was characterized using scanning electron microscopy (SEM), X-ray diffraction (XRD), and differential scanning calorimetry (DSC). Skin diffusion studies and tape-stripping were performed using human skin to determine the amount of clotrimazole accumulated in different layers of the skin. Results showed that the optimized formulation had vesicle size <250 nm with ~84% entrapment efficiency. XRD and DSC confirmed the entrapment of clotrimazole into ufosomes. No permeation was observed through the skin up to 24 h following the permeation studies. Tape-stripping revealed that ufosomes led to accumulation of more clotrimazole in the skin compared to marketed formulation (Perrigo). Overall, results revealed the capability of ufosomes in improving the skin bioavailability of clotrimazole.


Assuntos
Antifúngicos/metabolismo , Clotrimazol/metabolismo , Preparações de Ação Retardada/química , Composição de Medicamentos/métodos , Lipossomos/química , Administração Cutânea , Antifúngicos/química , Cadáver , Colesterol/química , Clotrimazol/química , Cultura em Câmaras de Difusão , Humanos , Cinética , Ácido Oleico/química , Tamanho da Partícula , Permeabilidade , Pele/metabolismo
10.
J Agric Food Chem ; 67(41): 11420-11427, 2019 Oct 16.
Artigo em Inglês | MEDLINE | ID: mdl-31545039

RESUMO

Experimental and clinical findings suggest that olive oil has a protective effect, whereas oleic acid consumption induces colorectal cancer (CRC). Considering this apparent contradiction and that olive oil is a complex mix of fatty acids, mainly oleic acid and minor compounds such as phenolic compounds, lignans, hydrocarbons, and triterpenes, we study its effects on intestinal epithelial cell growth. Our results show that oleic acid (1-100 µM) but not elaidic acid induced DNA synthesis and Caco-2 cell growth (2-fold higher than cells without growth factors, p < 0.05). These effects were inhibited by 5-lipoxygenase inhibitors as well as the leukotriene antagonist (p < 0.05), suggesting the implication of this pathway in this mitogenic action. Hydroxytyrosol, oleuropein, pinoresinol, squalene, and maslinic acid (0.1-10 µM) reverted DNA synthesis and Caco-2 cell growth induced by oleic acid. These effects were not the consequence of the cell cycle arrest or the impairment of cell viability with the exception of hydroxytyrosol and maslinic acid that induced cell detachment and apoptosis (35.6 ± 2.3 and 43.2 ± 2.4%, respectively) at the higher concentration assayed. Oleuropein effects can be related with hydroxytyrosol release as a consequence of oleuropein hydrolysis by Caco-2 cells (up to 25%). Furthermore, hydroxytyrosol modulates the arachidonic acid cascade, and this event can be associated with its antimitogenic action. In conclusion, oleic acid and oleic acid in the presence of olive oil representative minor components have opposite effects, suggesting that the consumption of seed oils, high oleic acid seed oils, or olive oil will probably have different effects on CRC.


Assuntos
Neoplasias do Colo/fisiopatologia , Mitógenos/metabolismo , Ácido Oleico/metabolismo , Azeite de Oliva/metabolismo , Apoptose , Células CACO-2 , Pontos de Checagem do Ciclo Celular , Proliferação de Células , Neoplasias do Colo/dietoterapia , Neoplasias do Colo/metabolismo , Humanos , Ácido Oleico/química , Ácidos Oleicos/química , Ácidos Oleicos/metabolismo , Azeite de Oliva/química
11.
Pharm Res ; 36(10): 147, 2019 Aug 14.
Artigo em Inglês | MEDLINE | ID: mdl-31414240

RESUMO

PURPOSE: The aim was to design and thoroughly characterize monodisperse Fe3O4@SiO2-Ag nanoparticles with strong antibacterial properties, which makes them a candidate for targeting bacterial infections. METHODS: The monodisperse Fe3O4 nanoparticles were prepared by oleic acid-stabilized thermal decomposition of Fe(III) oleate; the particles were coated with silica shell using a water-in-oil reverse microemulsion, involving hydrolysis and condensation of tetramethyl orthosilicate. Resulting Fe3O4@SiO2 particles were modified by (3-mercaptopropyl)trimethoxysilane to introduce 1.1 mmol SH/g. Finally, the Fe3O4@SiO2-SH nanoparticles were decorated with silver nanoclusters formed by reduction of silver nitrate with NaBH4. The particles were analyzed by FTIR, X-ray photoelectron and atomic absorption spectroscopy, dynamic light scattering and vibrating sample magnetometry. The antibacterial activity of the Fe3O4@SiO2 and Fe3O4@SiO2-Ag nanoparticles was tested against Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli bacteria cultivated on Luria agar plates or in Luria broth. RESULTS: The superparamagnetic Fe3O4@SiO2-Ag nanoparticles (21 nm in diameter; saturation magnetization 26 A∙m2/kg) were successfully obtained and characterized. Inhibitory and toxic effects against bacteria were documented by incubation of the Fe3O4@SiO2-Ag nanoparticles with Staphylococcus aureus and Escherichia coli. CONCLUSIONS: The combination of magnetic properties together with bactericidal effects is suitable for the disinfection of medical instruments, water purification, food packaging, etc.


Assuntos
Antibacterianos/química , Nanopartículas de Magnetita/química , Prata/química , Antibacterianos/farmacologia , Escherichia coli/efeitos dos fármacos , Ácido Oleico/química , Tamanho da Partícula , Silanos/química , Dióxido de Silício/química , Prata/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Propriedades de Superfície
12.
Int J Biol Macromol ; 138: 966-974, 2019 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-31356941

RESUMO

In the present study, we investigated the effects of complexing temperatures (75 °C and 95 °C) and oleic acid (OA) content (2%, 6%, 10% and 14%, w/w, dry basis of starch) on the structure and in vitro digestibility of maize starch-OA complexes. The resistant starch content, complexing index, thermal transition temperatures, enthalpy change and relative crystallinity of the complexes prepared at 75 °C were higher than those of corresponding complexes prepared at 95 °C. Additionally, starch-10% OA complexes prepared at 75 °C had the highest resistant starch content (18.82%), complexing index (78.83%) and relative crystallinity (14.62%). Fourier transform infrared spectroscopy revealed that the intermolecular interactions between starch and OA were affected by the complexing temperatures and OA content. Raman spectroscopy indicated that the starch-10% OA complexes prepared at 75 °Ð¡ had a greater short-range molecular order than other complexes. The V-type complexes were further confirmed as V6III polymorph structures according to the spectra obtained by nuclear magnetic resonance spectroscopy. Therefore, we conclude that complexing temperatures and OA content greatly changed the fine structure of the complexes, which further affected their digestibility.


Assuntos
Ácido Oleico/química , Amido/química , Temperatura Ambiente , Digestão , Hidrólise , Análise Espectral
13.
Plant Physiol Biochem ; 141: 423-430, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31233983

RESUMO

The effect of salinity on physiological traits, fatty acid composition and desaturase genes expression in fruit mesocarp of olive cultivar Leccino was investigated. Significant reduction of shoot elongation (-12%) during salt treatments (80 mM NaCl) was associated with the translocation of Na in the aerial part. After 75 days of treatment, fruits from each plant were subdivided into four maturation groups (MG0, MG1, MG2, MG3) according to ripening degrees. Na accumulation increased in each MG under salinity, reaching the highest values in MG1 fruits (2654 mg kg-1 DW). Salinity caused an acceleration of the ripening process, increased fruit number and decreased total fatty acids content in MG3. An increase in oleic acid at MG1 (53%) was detected, with consequent increase in the oleic/linoleic (41%) and decrease in the polyunsaturated/monounsaturated ratios (30%). Those variations could be explained by the synergic up-regulation of OeSAD1, together with the down-regulation of OeFAD6 transcript levels.


Assuntos
Ácidos Graxos Dessaturases/genética , Ácidos Graxos/química , Frutas/enzimologia , Olea/enzimologia , Sais/química , Irrigação Agrícola , Expressão Gênica , Ácido Linoleico/química , Ácido Oleico/química , Fenótipo , Fotossíntese , Óleos Vegetais/química , Sódio/química , Regulação para Cima
14.
Food Chem ; 295: 588-598, 2019 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-31174800

RESUMO

The encapsulation of eugenol (E) by spray-drying using whey protein (WP) or soy lecithin (LE) and maltodextrin in combination with oleic acid (OA) and chitosan (CH) was analysed in order to obtain antioxidant and antimicrobial powders for food applications. Formulations with only WP or LE showed higher encapsulation efficiencies (EE) (95-98%) and antibacterial effect against E. coli and L. innocua due to their greater E load. Incorporation of OA or CH promoted lower EE, which negatively affected the antimicrobial and antioxidant activities of the powders. Furthermore, the addition of CH implied less thermal protection against the E losses. The eugenol release was not notably affected by pH or polarity of the food simulant, but the release rate significantly decreased when incorporating OA and CH. The E-LE formulations better retained the eugenol than E-WP powders when heated above 200 °C, this being relevant for the powder inclusion in thermally treated products.


Assuntos
Anti-Infecciosos/química , Antioxidantes/química , Dessecação/métodos , Eugenol/química , Lecitinas/química , Proteínas do Soro do Leite/química , Anti-Infecciosos/farmacologia , Quitosana/química , Composição de Medicamentos , Escherichia coli/efeitos dos fármacos , Cinética , Listeria/efeitos dos fármacos , Ácido Oleico/química , Polissacarídeos/química
15.
Food Funct ; 10(6): 3142-3149, 2019 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-31157352

RESUMO

In this work, Candida antarctica lipase A was applied to selectively remove saturated fatty acids from palm oil to prepare palm oil acylglycerol concentrate (POAC), where palmitic acid decreased from 40.0 to 28.7% and oleic acid increased from 40.0 to 50.5% after 3 h of hydrolysis. Lipozyme RMIM from Rhizomucor miehei was then used to incorporate either alpha linolenic acid (ALA) or eicosapentaenoic acid (EPA) into the resulting POAC. Optimum omega-3 incorporation was achieved when POAC to omega-3 ratio was 6 : 3, reaction temperature was 40 °C and reaction time was 18 h. Under these conditions, the ALA content in the separated ALA incorporated structured lipid (POAC-ALA) was 27.1%, and the EPA content in the EPA incorporated structured lipids (POAC-EPA) was 30.9%. The formed structured lipids had lower levels of saturated fatty acids, and significantly lower melting points, in both cases below 8 °C. The enzymatic process developed produces new structured lipids, with lower saturated fat and higher omega-3, with potential as a healthy palm oil derived lipid ingredient.


Assuntos
Ácidos Graxos Ômega-3/química , Proteínas Fúngicas/química , Lipase/química , Óleo de Palmeira/química , Biocatálise , Candida/enzimologia , Ácido Oleico/química , Ácido Palmítico/química , Rhizomucor/enzimologia
16.
Talanta ; 202: 526-530, 2019 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-31171217

RESUMO

In this study, ferrofluid of magnetic nanoparticles, oleic acid (OA), combined with hydrophobic deep eutectic solvent (Fe3O4 [iron oxide]-OA-DES) was prepared and coupled with vortex-assisted liquid phase microextraction, to pre-concentrate and determine mefenamic acid (MFA) in urine samples, following high performance liquid chromatography (HPLC). With regard to Fe3O4 nanoparticles, all sorbents were identified by SEM, TEM, and XRD. In addition, the influence of different parameters such as pH, ferrofluid volume, ionic strong (NaCl concentration %), and vortex time was investigated and optimized by response surface methodology (RSM) and central composite design (CCD). Maximum MFA extraction predicted by RSM (97.66) was achieved at pH 4.0, 60 µL of ferrofluid, 3%w/v NaCl, and 7 min vortex time with desirability of 1.0. Under the optimized conditions, the limits of detection (LOD) and the limit of quantification (LOQ) were 1.351 ng mL-1 and 4.575 ng mL-1, respectively. The intra-day and inter-day precision (RSD [relative standard deviation]%) in the concentrations of 50, 300, and 700 ng mL-1 of MFA were less than 3.6% and 4.2%, respectively. The method developed in our study could successfully determine MFA in urine samples. The MFA microextraction in urine samples were between 80.25 and 97.44% with RSD% less than 4.60%. Inclusion of ferrofluid in a miniaturized method for sample preparation is proportional to the achievement of high microextraction percentage using green analytical method.


Assuntos
Compostos Férricos/química , Nanopartículas de Magnetita/química , Ácido Mefenâmico/urina , Ácido Oleico/química , Cromatografia Líquida de Alta Pressão , Portadores de Fármacos/química , Desenho de Equipamento , Humanos , Interações Hidrofóbicas e Hidrofílicas , Solventes/química
17.
Adv Exp Med Biol ; 1127: 169-179, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31140178

RESUMO

α-Synuclein (α-syn) represents the main component of the amyloid aggregates present in Parkinson's disease and other neurodegenerative disorders, collectively named synucleinopathies. Although α-syn is considered a natively unfolded protein, it shows great structural flexibility which allows the protein to adopt highly rich beta-sheet structures like protofibrils, oligomers and fibrils. In addition, this protein can adopt alpha-helix rich structures when interacts with fatty acids or acidic phospholipid vesicle membranes. When analyzing the toxicity of α-syn, protein oligomers are thought to be the main neurotoxic species by mechanisms that involve modification of intracellular calcium levels, mitochondrial and lysosomal function. Extracellular fibrillar α-syn promotes intracellular protein aggregation and shows many toxic effects as well. Nitro-fatty acids (nitroalkenes) represent novel pleiotropic anti-inflammatory signaling mediators that could interact with α-syn to exert unraveling actions. Herein, we demonstrated that nitro-oleic acid (NO2-OA) nitroalkylate α-syn, forming a covalent adduct at histidine-50. The nitroalkylated-α-syn exhibited strong affinity for phospholipid vesicles, moving the protein to the membrane compartment independent of composition of the membrane phospholipids. Moreover, NO2-OA-modified α-syn showed a reduced capacity to induce α-syn fibrillization compared to the non-nitrated oleic acid. From this data we hypothesize that nitroalkenes, in particular NO2-OA, may inhibit α-syn fibril formation exerting protective actions in Parkinson's disease.


Assuntos
Ácido Oleico/química , Doença de Parkinson/patologia , alfa-Sinucleína/química , Amiloide , Humanos , Doenças Neurodegenerativas/patologia , Fosfolipídeos
18.
Int J Biol Macromol ; 134: 604-612, 2019 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-31100395

RESUMO

In the present research the effect of incorporating cinnamon essential oil (CEO), oleic acid (OA) and glutaraldehyde (GL) on antimicrobial, antioxidant, mechanical, physical and morphological properties of chitosan-carboxymethyl cellulose composite films were investigated. Cross-linking effect of GL (as determined by FTIR analysis) significantly resulted in higher mechanical strength and lower water vapor permeability (WVP). Cross-linked films incorporated with CEO revealed higher and steady state antioxidant activity as well as in vitro antimicrobial properties against Listeria monocytogenes and Pseudomonas aeruginosa. Thickness, elongation at break (EAB) and WVP increased by including OA; however, water solubility significantly decreased. Color properties and microstructure of composite films were significantly affected by the additives as confirmed by SEM analyses. We showed that the antimicrobial, antioxidant, mechanical and physical properties of chitosan-carboxymethyl cellulose composite films could be improved via incorporating CEO and GL to the film matrix.


Assuntos
Quitosana/análogos & derivados , Quitosana/química , Cinnamomum zeylanicum/química , Glutaral/química , Óleos Voláteis/química , Ácido Oleico/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Fenômenos Químicos , Fenômenos Mecânicos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Solubilidade , Análise Espectral
19.
Parasitol Res ; 118(7): 2295-2304, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31093751

RESUMO

Acanthamoeba castellanii belonging to the T4 genotype is an opportunistic pathogen which is associated with blinding eye keratitis and rare but fatal central nervous system infection. A. castellanii pose serious challenges in antimicrobial chemotherapy due to its ability to convert into resistant, hardy shell-protected cyst form that leads to infection recurrence. The fatty acid composition of A. castellanii trophozoites is known to be most abundant in oleic acid which chemically is an unsaturated cis-9-Octadecanoic acid and naturally found in animal and vegetable fats and oils. This study was designed to evaluate antiacanthamoebic effects of oleic acid against trophozoites, cysts as well as parasite-mediated host cell cytotoxicity. Moreover, oleic acid-conjugated silver nanoparticles (AgNPs) were also synthesized and tested against A. castellanii. Oleic acid-AgNPs were synthesized by chemical reduction method and characterized by ultraviolet-visible spectrophotometry, atomic force microscopy, dynamic light scattering analysis, and Fourier transform infrared spectroscopy. Viability, growth inhibition, encystation, and excystation assays were performed with 10 and 5 µM concentration of oleic acid alone and oleic acid-conjugated AgNPs. Bioassays revealed that oleic acid alone and oleic acid-conjugated AgNPs exhibited significant antiamoebic properties, whereas nanoparticle conjugation further enhanced the efficacy of oleic acid. Phenotype differentiation assays also showed significant inhibition of encystation and excystation at 5 µM. Furthermore, oleic acid and oleic acid-conjugated AgNPs also inhibited amoebae-mediated host cell cytotoxicity as determined by lactate dehydrogenase release. These findings for the first time suggest that oleic acid-conjugated AgNPs exhibit antiacanthamoebic activity that hold potential for therapeutic applications against A. castellanii.


Assuntos
Ceratite por Acanthamoeba/tratamento farmacológico , Acanthamoeba castellanii/efeitos dos fármacos , Amebicidas/farmacologia , Nanopartículas Metálicas/química , Ácido Oleico/farmacologia , Ceratite por Acanthamoeba/parasitologia , Amebicidas/química , Animais , Olho/parasitologia , Humanos , Microscopia de Força Atômica , Ácido Oleico/química , Prata/química , Espectrofotometria Ultravioleta , Trofozoítos/efeitos dos fármacos
20.
J Oleo Sci ; 68(6): 567-572, 2019 Jun 06.
Artigo em Inglês | MEDLINE | ID: mdl-31092796

RESUMO

We characterized the friction and adsorption properties of an oleic acid-based gemini amphiphile having two carboxylic acid headgroups. We employed silica as a solid material, and diethyl sebacate and bis (2-ethylhexyl) sebacate as polar ester oils. Oleic acid and stearic acid were used as comparative amphiphilic materials. These amphiphiles were soluble in the ester oils, and the solubility of the gemini amphiphile was lower than that of the other two amphiphiles. Quartz crystal microbalance with dissipation monitoring measurements suggested that the gemini amphiphile had greater adsorption capability than the two comparative amphiphiles. The greater adsorption density of the gemini amphiphile resulted in the formation of a rigid interfacial film, as suggested by the normal force curves obtained by atomic force microscopy (AFM). We assessed the friction property of these systems using a ball-on-plate-type friction analyzer and by friction-mode AFM (friction force curve). These measurements confirmed that the gemini amphiphile had a smaller kinetic friction coefficient than that of the other two amphiphiles. These results suggest the potential of the gemini amphiphile as a friction modifier in polar oils.


Assuntos
Adsorção , Calcitriol/análogos & derivados , Ácidos Decanoicos/química , Fricção , Ácido Oleico/química , Dióxido de Silício/química , Ácidos Esteáricos/química , Tensoativos/química , Calcitriol/química , Ácidos Carboxílicos , Solubilidade
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