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1.
J Agric Food Chem ; 67(41): 11518-11526, 2019 Oct 16.
Artigo em Inglês | MEDLINE | ID: mdl-31513385

RESUMO

In this work, the effects of α-linolenic acid (ALA) loaded in oil-in-water (O/W) and water-in-oil-in-water (W/O/W) microemulsions on cell viability, lactic dehydrogenase (LDH) viability, and reactive oxygen species (ROS) levels were examined using Cell Counting Kit-8 (CCK-8), an LDH assay kit, and a fluorescence microscope, respectively. The CCK-8 assay demonstrated that ALA inhibited MDA-MB-231 human breast cancer cell proliferation in a dose-dependent manner. Further, the results of LDH activity and ROS levels revealed that ALA-induced cancer cell damage was closely related to oxidative stress. Under the irradiation of ultraviolet light, the microemulsion without any added fluorescent dye would emit bright blue fluorescence, and the fluorescent images of the cells treated with ALA-loaded O/W and W/O/W microemulsions at different incubation times were taken, which exhibited long-term photostability and biocompatibility. In addition, the fluorescence mechanism of the microemulsion was explained by immobilizing surfactant molecules with aggregation-induced emission (AIE) properties at the water-oil interface through the microemulsion with a self-assembled structure. These findings showed the potential application of O/W and W/O/W microemulsions as the label-free delivery carriers in long-term imaging of living cells and real-time release monitoring of nutrients.


Assuntos
Proliferação de Células/efeitos dos fármacos , Ácido alfa-Linoleico/química , Ácido alfa-Linoleico/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Portadores de Fármacos/química , Emulsões/química , Emulsões/farmacologia , Fluorescência , Humanos , Óleos/química , Espécies Reativas de Oxigênio/metabolismo , Água/química
2.
J Food Sci ; 84(7): 1966-1978, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31206695

RESUMO

The evolution of volatile aldehydes and the conversion of oxygenated ityß-unsaturated aldehydes (OαßUAs) into furans were compared in four vegetable oils (soybean oil, olive oil [OVO], peanut oil [PO], and perilla oil [PAO]) thermally oxidized at temperatures of 150, 180, and 210 °C for 10 hr/day over a 3-day period. Results showed that 2 alkyl furans and 23 volatile aldehydes including 4 toxic OdßUAs were detected by GC-MS. The original fatty acid compositions of the oils played a key role in the type and concentration of those volatile compounds. 4-Hydroxy-2-hexenal (HHE) and ethyl furan were only detected in PAO with a high content of linolenic acid, while the greatest level of pentyl furan was detected in PO with abundant linoleic acid. Greater amounts of 4-hydroxy-(E)-2-nonenal (HNE) and 4-oxo-(E)-2-nonenal (ONE) were formed in the OVO with abundant oleic acid. The close relativity of HHE and ethyl furan was also demonstrated. With principal component analysis, these vegetable oils could be discriminated based on their fatty acids and volatile compounds. The loading plot confirmed that HHE and ethyl furan were derived from the linolenic acid oxidation and degradation. PRACTICAL APPLICATION: The chemometric results showed that the formation of the volatile components during heating in different vegetable oils has close correlation with the original fatty acids composition of vegetable oils. Our research has also confirmed the presence of toxic OɑßUAs in oils after heating. Considering that they are proven to generate lots of degenerative diseases, further studies are needed to establish the risk level of using certain oils in frying and seek effective methods to inhibit their formation.


Assuntos
Aldeídos/química , Furanos/química , Azeite de Oliva/química , Óleo de Amendoim/química , Óleo de Soja/química , Ácido alfa-Linoleico/química , Ácidos Graxos/química , Cromatografia Gasosa-Espectrometria de Massas , Temperatura Alta , Oxirredução , Óleos Vegetais/química
3.
Food Chem ; 294: 56-59, 2019 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-31126500

RESUMO

Perilla oil is abundant in α-linolenic acid, which is metabolized to long-chain n-3 fatty acids. This study aimed to determine thermal stability and bioavailability of perilla oil that was powdered by inclusion complexation with γ-cyclodextrin. Fatty acid analysis revealed that the relative abundance of α-linolenic and linoleic acids in the complexes was not affected by heating at 40 °C for six days but decreased after heating at 60 °C for three days. No adverse events occurred in rats fed with an experimental diet containing the complexes for two weeks. Plasma α-linolenic and eicosapentaenoic acids in rats fed with diets containing complexes and liquid perilla oil were equally high, indicating the preserved bioavailability of perilla oil in the complexes. Plasma arachidonic acid decreased only in rats fed with a diet containing the complexes. Results suggest that the complexes have potential as a useful source of α-linolenic acid to increase plasma n-3 fatty acids.


Assuntos
Ácido alfa-Linoleico/química , gama-Ciclodextrinas/química , Animais , Disponibilidade Biológica , Cromatografia Líquida de Alta Pressão , Dieta , Ácidos Graxos/sangue , Cromatografia Gasosa-Espectrometria de Massas , Ácidos Linoleicos/sangue , Masculino , Óleos Vegetais/química , Óleos Vegetais/metabolismo , Ratos , Ratos Wistar , Espectrometria de Massas por Ionização por Electrospray , Temperatura Ambiente , Ácido alfa-Linoleico/metabolismo , gama-Ciclodextrinas/metabolismo
4.
J Sep Sci ; 42(14): 2360-2370, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31066188

RESUMO

α-Linolenic acid is an essential omega-3 fatty acid needed for human health. However, the isolation of high-purity α-linolenic acid from plant resources is challenging. The preparative separation methods of α-linolenic acid by both conventional and pH-zone refining counter current chromatography were firstly established in this work. The successful separation of α-linolenic acid by conventional counter current chromatography was achieved by the optimized solvent system n-heptane/methanol/ water/acetic acid (10:9:1:0.04, v/v), producing 466 mg of 98.98% α-linolenic acid from 900 mg free fatty acid sample prepared from perilla seed oil with linoleic acid and oleic acid as by-products. The scaled-up separation in 45× is efficient without loss of resolution and extension of separation time. The separation of α-linolenic acid by pH-zone refining counter current chromatography was also satisfactory by the solvent system n-hexane/methanol/water (10:5:5, v/v) and the optimized concentration of trifluoroacetic acid 30 mM and NH4 OH 10 mM. The separation can be scaled up in 180× producing 9676.7 mg of 92.79% α-linolenic acid from 18 000 mg free fatty acid sample. pH-zone refining counter current chromatography exhibits a great advantage over conventional counter current chromatography with 20× sample loading capacity on the same column.


Assuntos
Extratos Vegetais/isolamento & purificação , Ácido alfa-Linoleico/isolamento & purificação , Distribuição Contracorrente , Concentração de Íons de Hidrogênio , Extratos Vegetais/química , Óleos Vegetais/química , Ácido alfa-Linoleico/química
5.
Poult Sci ; 98(7): 3059-3066, 2019 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-30877751

RESUMO

The potential use of an oil in water (o/w) emulsion made from perilla and canola oil in chicken sausage as an animal fat replacer was assessed. The (o/w) emulsion was made from 50% (wt/wt) perilla-canola oil mixture in a 30:70 ratio, 3.20% (wt/wt) polyglycerol polyricinoleate, 4.48% (wt/wt) soy protein isolate, 14% (wt/wt) inulin, and 28.32% (wt/wt) water. The sausages were manufactured with 60% (wt/wt) ground chicken breast, 20% (wt/wt) fat (beef tallow as a control), and 20% (wt/wt) ice water. Full replacement of animal fat with a perilla-canola oil (o/w) emulsion reduced the fat content and estimated calories but increased the moisture, protein, ash, and carbohydrate content. The proportion of α-linolenic acid (C18:3n3) was increased when animal fat was replaced with either a perilla-canola oil mixture or pre-emulsified perilla-canola oil, resulting in a lower n6 to n3 polyunsaturated fatty acid ratio than the control. The perilla-canola oil (o/w) emulsion improved emulsion stability and minimized cooking loss during sausage manufacturing. Higher L* value (lightness) and whiteness were observed in the sausages formulated with the perilla-canola oil mixture, followed by the pre-emulsified perilla-canola oil and the control. The perilla-canola oil (o/w) emulsion also increased the hardness but maintained an acceptable appearance, flavor, and overall impression similar to the control. The shelf life could be extended by vacuum packing and storing the cooked sausages formulated with a perilla-canola oil (o/w) emulsion for 30 D at 2 ± 1°C. Pre-emulsified perilla-canola oil could be used to replace animal fat in reduced-fat chicken sausage manufacture.


Assuntos
Produtos da Carne/análise , Óleo de Brassica napus/química , Ácido alfa-Linoleico/química , Animais , Bovinos , Galinhas , Substitutos da Gordura , Ácidos Graxos/análise , Manipulação de Alimentos/métodos , Armazenamento de Alimentos , Humanos , Óleos Vegetais/química , Paladar
6.
Food Chem ; 286: 584-591, 2019 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-30827650

RESUMO

This study reports the blending at different levels (25, 30, 35, 40 and 45%) of Perilla seed oil (PO) with extra virgin olive oil (EVOO). Pure oils and blends were evaluated in terms of free acidity, peroxide value, fatty acid composition, sterols, tocopherols and biophenols content, oxidation stability, sensory acceptability and food pairing. Blends with high content of ω - 3 and ω - 6 fatty acids, biophenols, tocopherols, sterols and satisfying oxidation stability were obtained, representing products with improved nutritional properties. All blends resulted acceptable by consumers. Two groups of consumers with opposite preferences for samples with low (25-35%) and high (40-45%) levels of PO were identified. Blends containing 40-45% of PO were mainly paired to strong-flavour and cooked foods, while blends with less PO were preferably matched with raw meat and vegetables. Consequently, PO and EVOO blends showed promising potential as innovative vegetable oils with improved nutritional properties and versatile gastronomic use.


Assuntos
Azeite de Oliva/química , Ácido alfa-Linoleico/química , Adolescente , Adulto , Comportamento do Consumidor , Ácidos Graxos/análise , Feminino , Humanos , Itália , Masculino , Pessoa de Meia-Idade , Oxirredução , Peróxidos/análise , Fenóis/análise , Óleos Vegetais/química , Esteróis/análise , Paladar , Tocoferóis/análise
7.
Molecules ; 24(3)2019 Feb 02.
Artigo em Inglês | MEDLINE | ID: mdl-30717326

RESUMO

Although many investigations on phytochemicals in rice plant parts and root exudates have been conducted, information on the chemical profile of essential oil (EO) and potent biological activities has been limited. In this study, chemical compositions of rice leaf EO and in vitro biological activities were investigated. From 1.5 kg of fresh rice leaves, an amount of 20 mg EO was obtained by distillation and analyzed by gas chromatography-mass spectrometry (GC-MS), electrospray ionization (ESI), and atmospheric pressure chemical ionization (APCI) to reveal the presence of twelve volatile constituents, of which methyl ricinoleate (27.86%) was the principal compound, followed by palmitic acid (17.34%), and linolenic acid (11.16%), while 2-pentadecanone was the least (2.13%). Two phytoalexin momilactones A and B were first time identified in EO using ultra-performance liquid chromatography coupled with electrospray mass spectrometry (UPLC/ESI-MS) (9.80 and 4.93 ng/g fresh weight, respectively), which accounted for 7.35% and 3.70% of the EO, respectively. The assays of DPPH (IC50 = 73.1 µg/mL), ABTS (IC50 = 198.3 µg/mL), FRAP (IC50 = 700.8 µg/mL) and ß-carotene oxidation (LPI = 79%) revealed that EO possessed an excellent antioxidant activity. The xanthine oxidase assay indicated that the anti-hyperuricemia potential was in a moderate level (IC50 = 526 µg/mL) as compared with the standard allopurinol. The EO exerted potent inhibition on growth of Raphanus sativus, Lactuca sativa, and two noxious weeds Echinochloa crus-galli, and Bidens pilosa, but in contrast, the growth of rice seedlings was promoted. Among the examined plants, the growth of the E. crus-galli root was the most inhibited, proposing that constituents found in EO may have potential for the control of the problematic paddy weed E. crus-galli. It was found that the EO of rice leaves contained rich phytochemicals, which were potent in antioxidants and gout treatment, as well as weed management. Findings of this study highlighted the potential value of rice leaves, which may provide extra benefits for rice farmers.


Assuntos
Antioxidantes/química , Óleos Voláteis/química , Oryza/química , Compostos Fitoquímicos/química , Cromatografia Gasosa-Espectrometria de Massas , Alface/efeitos dos fármacos , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Raízes de Plantas/química , Raphanus/efeitos dos fármacos , Ácidos Ricinoleicos/química , Plântula/efeitos dos fármacos , Espectrometria de Massas por Ionização por Electrospray , Xantina Oxidase/química , Ácido alfa-Linoleico/química
8.
Lipids Health Dis ; 18(1): 53, 2019 Feb 14.
Artigo em Inglês | MEDLINE | ID: mdl-30764880

RESUMO

BACKGROUND: Supplemented fatty acids can incorporate into cardiolipin (CL) and affect its remodeling. The change in CL species may alter the mitochondrial membrane composition, potentially disturbing the mitochondrial structure and function during inflammation. METHOD: To investigate the effect of the unsaturation of fatty acids on CL, we supplemented macrophage-like RAW264.7 cells with 18-carbon unsaturated fatty acids including oleic acid (OA, 18:1), linoleic acid (LA, 18:2), α-linolenic acid (ALA, 18:3), γ-linolenic acid (GLA, 18:3), and stearidonic acid (SDA, 18:4). Mitochondrial changes in CL were measured through mass spectrometry. RESULT: Our data indicated that OA(18:1) was the most efficient fatty acid that incorporated into CL, forming symmetrical CL without fatty acid elongation and desaturation. In addition, LA(18:2) and ALA(18:3) were further elongated before incorporation, significantly increasing the number of double bonds and the chain length of CL. GLA and SDA were not optimal substrates for remodeling enzymes. The findings of RT-qPCR experiments revealed that none of these changes in CL occurred through the regulation of CL remodeling- or synthesis-related genes. The fatty acid desaturase and transportation genes-Fads2 and Cpt1a, respectively-were differentially regulated by the supplementation of five unsaturated 18-carbon fatty acids. CONCLUSIONS: The process of fatty acid incorporation to CL was regulated by the fatty acid desaturation and transportation into mitochondria in macrophage. The double bonds of fatty acids significantly affect the incorporation process and preference. Intact OA(18:1) was incorporated to CL; LA(18:2) and ALA(18:3) were desaturated and elongated to long chain fatty acid before the incorporation; GLA(18:3) and SDA(18:4) were unfavorable for the CL incorporation.


Assuntos
Cardiolipinas/biossíntese , Ácidos Graxos Ômega-3/farmacologia , Ácido Linoleico/farmacologia , Membranas Mitocondriais/efeitos dos fármacos , Ácido Oleico/farmacologia , Ácido alfa-Linoleico/farmacologia , Ácido gama-Linolênico/farmacologia , Animais , Transporte Biológico , Carnitina O-Palmitoiltransferase/genética , Carnitina O-Palmitoiltransferase/metabolismo , Ácidos Graxos Dessaturases/genética , Ácidos Graxos Dessaturases/metabolismo , Ácidos Graxos Ômega-3/química , Ácidos Graxos Ômega-3/metabolismo , Perfilação da Expressão Gênica , Regulação da Expressão Gênica , Ácido Linoleico/química , Ácido Linoleico/metabolismo , Camundongos , Mitocôndrias/química , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Membranas Mitocondriais/química , Membranas Mitocondriais/metabolismo , Ácido Oleico/química , Ácido Oleico/metabolismo , Células RAW 264.7 , Relação Estrutura-Atividade , Ácido alfa-Linoleico/química , Ácido alfa-Linoleico/metabolismo , Ácido gama-Linolênico/química , Ácido gama-Linolênico/metabolismo
9.
Food Chem ; 280: 286-293, 2019 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-30642499

RESUMO

As a major sterol in edible mushroom, ergosterol has gained much attention owing to its potential bioactivities. However, ergosterol has a high melting point, poor oil solubility and stability, which restrict its scope of application. In this study, an ergosterol ester of α-linolenic acid was successfully and efficiently prepared using Candida sp. 99-125 lipase as a biocatalyst. The desired product was confirmed to be ergosterol linolenate using MS, FT-IR, and NMR analyses. Using Candida sp. 99-125 lipase, the product conversion exceeded 92% in 12 h under the following optimized parameters: 75 mmol/L ergosterol, 40 g/L lipase, 1:1.25 ergosterol-to-α-linolenic acid molar ratio, and 45 °C. The results confirmed that Candida sp. 99-125 lipase has good reusability and stability and is also relatively low cost, suggesting its great potential for large-scale production of ergosterol ester. Most importantly, the physiochemical properties (oil solubility and melting point) of ergosterol significantly improved after esterification with α-linolenic acid, thus facilitating its application in oil-based systems.


Assuntos
Candida/enzimologia , Ergosterol/metabolismo , Lipase/metabolismo , Ácido alfa-Linoleico/metabolismo , Biocatálise , Enzimas Imobilizadas/química , Enzimas Imobilizadas/metabolismo , Ergosterol/química , Esterificação , Lipase/química , Espectroscopia de Ressonância Magnética , Óleos Voláteis/química , Óleos Voláteis/metabolismo , Solubilidade , Temperatura Ambiente , Ácido alfa-Linoleico/química
10.
Microb Pathog ; 126: 56-62, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30393116

RESUMO

This study aimed to investigate the total phenolic content (TPC), the identification of the common compounds by HPLC-ESI-MS and HPLC-ESI-MS-TOF and the inhibitory effects against class A-type ß-lactamase (GES-22 variant, produced recombinantly) in methanolic extracts (MEs) of four Algerian seaweeds [Ulva intestinalis, Codium tomentosum, Dictyota dichotoma and Halopteris scoparia]. The TPC varied among the four species, ranging between 0.93 ±â€¯0.65 and 2.66 ±â€¯1.33 mg GAEs/g DW. C.tomentosum had higher total phenol content than other seaweeds while, all of them inhibited uncompetitively GES-22 activity in a dose-dependent manner. Nitrocefin was used as chromogenic substrate to evaluate the inhibitory effect on GES-22. The methanolic extract of D.dichotoma exhibited significant inhibitory effect on GES-22 (IC50 = 13.01 ±â€¯0.046 µg/mL) more than clavulanate, sulbactam and tazobactam (classical ß-lactam inhibitors) (IC50 = 68.38 ±â€¯0.17 µg/mL, 52.68 ±â€¯0.64 µg/mL, and 29.94 ±â€¯0.01 µg/mL, respectively). IC50 of the other ME of U.intestinalis, C.tomentosum, and H.scoparia were 16.87 ±â€¯0.10 µg/mL, 16.54 ±â€¯0.048 µg/mL, and 25.72 ±â€¯0.15 µg/mL, respectively. Except H. scoparia, other three seaweed extracts showed almost two times or more inhibition on GES-22. Furthermore, four common compounds in these MEs were identified, α-linolenic acid (C18:3ω3), linoleic acid (C18:2ω6), oleic acid (C18:1ω9), the eicosanoid precursors ''arachidonic acid'' (C20:4ω6). Baicalein (C15H10O5) was identified in U.intestinalis and D.dichotoma seaweeds. The fact that all seaweed extracts inhibited the GES-22 better than commercial samples makes these seaweeds candidate for discovering new inhibitors against ß-lactamases. Besides that, they contain important components with potential health benefits.


Assuntos
Extratos Vegetais/antagonistas & inibidores , Alga Marinha/química , beta-Lactamases/efeitos dos fármacos , Argélia , Ácido Araquidônico/química , Clorófitas/química , Ensaios Enzimáticos , Flavanonas/química , Mar Mediterrâneo , Metanol , Ácido Oleico/química , Feófitas/química , Fenóis/química , Ácido alfa-Linoleico/química
11.
J Dairy Sci ; 102(2): 1213-1223, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30580947

RESUMO

The basis for marine lipid-induced milk fat depression (MFD) has not been established yet, but recent reports suggest the putative contribution of shifts in the ruminal metabolism of α-linolenic acid (ALA). To test this hypothesis, an isotopic tracer approach was used in batch cultures of rumen microorganisms with inoculum collected from cannulated ewes fed either a total mixed ration without lipid supplementation (control inoculum) or the same diet supplemented with 2% of fish oil, which is known to cause MFD in lactating sheep (FO-MFD inoculum). The [1-13C]ALA was added at a dose of 1% of incubated dry matter and the proportions of 13C-labeled fatty acids (FA) were examined after 24 h of incubation, using complementary gas chromatography and gas chromatography-combustion isotope ratio mass spectrometry (GC-C-IRMS) analyses. Expected differences in FA profiles were confirmed between control and FO-MFD inocula (e.g., large decreases in 18:0 and increases in most 18:1 and 18:2 intermediates, particularly trans isomers, to fish oil supply). The biohydrogenation of 13ALA was extensive and yielded multiple metabolites, with a total of 48 chromatographic peaks showing 13C enrichment, regardless of the inoculum type. However, although ALA was biohydrogenated through common pathways under standard or MFD conditions, large changes in the accumulation of 13C-labeled FA suggest important differences in the relative contribution of each specific route. First, increased accumulation of trans-11-containing FA in FO-MFD incubations was accompanied by a general repression of the trans-13/14 pathway (supported by lower trans-13+14 18:1 or trans-11,trans-13 18:2 proportions), together with a lower production of cis FA (e.g., cis-9, -12, and -15 18:1 and some cis,cis 18:2). Results also downplayed the relevance of the trans-11 to trans-10 shift as an effective marker of diet-induced MFD in sheep, and challenged the involvement of some trans-10 intermediates (e.g., trans-10 18:1 and trans-10,cis-15 18:2) in the low-fat milk syndrome in this species. Conversely, increased abundance of most 18:3 intermediates (including some unidentified isomers) might be representative of ruminal alterations related to fish oil supplementation in ewes. Further research is necessary to examine the potential association between these findings and MFD in lactating animals.


Assuntos
Gorduras/química , Leite/metabolismo , Rúmen/metabolismo , Ovinos/metabolismo , Ácido alfa-Linoleico/metabolismo , Animais , Isótopos de Carbono/química , Isótopos de Carbono/metabolismo , Dieta/veterinária , Suplementos Nutricionais/análise , Gorduras/metabolismo , Ácidos Graxos/química , Ácidos Graxos/metabolismo , Feminino , Óleos de Peixe/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Leite/química , Ácido alfa-Linoleico/química
12.
Food Chem ; 278: 119-126, 2019 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-30583352

RESUMO

In the western diet there is an oversupply of n-6 fatty acids. This adverse trend can be balanced by the consumption of rapeseed and flaxseed oils rich in α-linolenic acid (n-3). However, the high share of this fatty acid contributes to low oxidative stability of oil. Oxidation decreases n-3 fatty acid and other bioactive compounds contents, which adversely affects oil nutritional value. In this study, the impact of ferulic and sinapic acids vinyl derivatives on the fatty acids and oil terpenoids (sterols, tocols, carotenoids, squalene) retention at the end of induction period during accelerated oxidation of rapeseed and flaxseed cold-pressed oils was investigated. It was found that the use of 4-vinylsyringol (4-VS) or 4-vinylquaiacol (4-VQ) increased the retention of intact sterols and carotenoids (at least 2-fold) and squalene (at least 4-fold). The 4-VQ addition also inhibited the α-linolenic acid loss. Unfortunately, both phenolic derivatives favoured α-tocopherol decay in rapeseed oil.


Assuntos
Ácidos Graxos/química , Óleo de Semente do Linho/química , Pirogalol/análogos & derivados , Óleo de Brassica napus/química , Terpenos/química , Carotenoides/análise , Carotenoides/química , Ácidos Cumáricos/química , Ácidos Graxos/análise , Manipulação de Alimentos/métodos , Óleo de Semente do Linho/análise , Oxirredução , Pirogalol/química , Óleo de Brassica napus/análise , Terpenos/análise , Ácido alfa-Linoleico/química
13.
J Agric Food Chem ; 66(49): 13020-13030, 2018 Dec 12.
Artigo em Inglês | MEDLINE | ID: mdl-30507107

RESUMO

Our previous work has demonstrated that α-linolenic acid (ALA)-loaded oil-in-water (O/W) microemulsion could enhance ALA antioxidant capacity. Meanwhile, we also observed that synthesized microemulsion itself had fluorescence. In this work, we have prepared a multiple water-in-oil-in-water (W/O/W) microemulsion to further enhance ALA antioxidant capacity and activate this delivery carrier application potential with a free label. The compositions of primary water-in-oil (W/O) microemulsion were obtained using pseudo-ternary phase diagrams, and then W/O/W microemulsion was prepared adopting the "two-step heterotherm method". The conductivity of W/O/W microemulsion was measured to lie between 250.0 and 350.0 µs/cm. The spherical droplets with a mean particle diameter of 10.0-20.0 nm were confirmed by transmission electron microscopy and dynamic light scattering. Nuclear magnetic resonance confirmed that ALA diffused to the multiple water-oily interface simultaneously. In addition, the in vitro release and antioxidant capacity measurements of ALA-loaded W/O/W microemulsion concluded the sustained-release effect and excellent antioxidant capacity. The fluorescent intensity of W/O/W microemulsion was markedly increased in comparison to O/W microemulsion. The synthesized microemulsion could lead to important applications and have advantages of a label-free fluorescent carrier for optical imaging purposes.


Assuntos
Emulsões/química , Ácido alfa-Linoleico/administração & dosagem , Ácido alfa-Linoleico/química , Antioxidantes , Sistemas de Liberação de Medicamentos , Condutividade Elétrica , Fluorescência , Tamanho da Partícula , Pentanóis/química , Espectrometria de Fluorescência/métodos , Tensoativos , Água/química
14.
Molecules ; 23(12)2018 Dec 06.
Artigo em Inglês | MEDLINE | ID: mdl-30563201

RESUMO

The purpose of this research was to investigate the chemical profile, nutritional quality, antioxidant and hypolipidemic effects of Mexican chia seed oil (CSO) in vitro. Chemical characterization of CSO indicated the content of α-linolenic acid (63.64% of total fatty acids) to be the highest, followed by linoleic acid (19.84%), and saturated fatty acid (less than 11%). Trilinolenin content (53.44% of total triacylglycerols (TAGs)) was found to be the highest among seven TAGs in CSO. The antioxidant capacity of CSO, evaluated with ABTS•+ and DPPH• methods, showed mild antioxidant capacity when compared with Tocopherol and Catechin. In addition, CSO was found to lower triglyceride (TG) and low-density lipoprotein-cholesterol (LDL-C) levels by 25.8% and 72.9%respectively in a HepG2 lipid accumulation model. As CSO exhibits these chemical and biological characteristics, it is a potential resource of essential fatty acids for human use.


Assuntos
Compostos Fitoquímicos/química , Óleos Vegetais/química , Salvia/química , Antioxidantes/química , Ácidos Graxos/química , Células Hep G2 , Humanos , Compostos Fitoquímicos/metabolismo , Óleos Vegetais/metabolismo , Sementes/química , Triglicerídeos , Ácido alfa-Linoleico/química
15.
Mol Nutr Food Res ; 62(24): e1800299, 2018 12.
Artigo em Inglês | MEDLINE | ID: mdl-30358922

RESUMO

SCOPE: The aim of this study is to examine whether perilla oil supplementation improves glucolipid metabolism and modulates gut microbiota in diabetic KKAy mice. METHODS AND RESULTS: The successfully established diabetic KKAy mice are randomized into four groups: diabetic model (DM), low-dose perilla oil (LPO), middle-dose perilla oil (MPO), and high-dose perilla oil (HPO). C57BL/6J mice are fed a chow diet as normal control (NC). At the end of 12 weeks, mice are euthanized and glucolipid indications are analyzed. Gut microbiota analysis is carried out based on the sequencing results on V4 region of 16S rRNA. Although serum glucose, insulin, total cholesterol, low-density lipoprotein cholesterol, high-density lipoprotein cholesterol, abundance-based coverage estimator, and shannon are unchanged, serum triglyceride significantly decreases in LPO compared with DM. The histopathological changes of hepatocellular macrovesicular steatosis and adipocyte hypertrophy are ameliorated by perilla oil supplementation. Blautia is significantly decreased in LPO, MPO, and HPO, compared with DM. Nonmetric multidimensional scaling analysis shows NC and LPO are relatively coherent. CONCLUSION: These findings indicate that dietary supplementation with perilla oil can improve hypertriglyceridemia and gut dysbiosis in diabetic KKAy mice, which can be associated with potential benefits to human health.


Assuntos
Disbiose/dietoterapia , Microbioma Gastrointestinal/efeitos dos fármacos , Hipertrigliceridemia/dietoterapia , Ácido alfa-Linoleico/farmacologia , Tecido Adiposo/efeitos dos fármacos , Tecido Adiposo/patologia , Animais , Diabetes Mellitus Experimental/dietoterapia , Suplementos Nutricionais , Ácidos Graxos Ômega-3/farmacologia , Microbioma Gastrointestinal/genética , Hipertrigliceridemia/sangue , Insulina/sangue , Lipídeos/sangue , Fígado/efeitos dos fármacos , Fígado/patologia , Masculino , Camundongos Endogâmicos C57BL , Camundongos Endogâmicos , Óleos Vegetais/administração & dosagem , Óleos Vegetais/química , Óleos Vegetais/farmacologia , RNA Ribossômico 16S , Ácido alfa-Linoleico/administração & dosagem , Ácido alfa-Linoleico/química
16.
Molecules ; 23(10)2018 Oct 21.
Artigo em Inglês | MEDLINE | ID: mdl-30347888

RESUMO

Soybeans are low in saturated fat and a rich source of protein, dietary fiber, and isoflavone; however, their nutritional shelf life is yet to be established. This study evaluated the change in the stability and quality of fatty acids in raw and roasted soybean flour under different storage temperatures and durations. In both types of soybean flour, the fatty-acid content was the highest in the order of linoleic acid (18-carbon chain with two double bonds; C18:2), oleic acid (C18:1), palmitic acid (C16:0), linolenic acid (18:3), and stearic acid (C18:0), which represented 47%, 26%, 12%, 9%, and 4% of the total fatty-acid content, respectively. The major unsaturated fatty acids of raw soybean flour-oleic acid, linoleic acid, and linolenic acid-decreased by 30.0%, 94.4%, and 97.7%, and 38.0%, 94.8%, and 98.0% when stored in polyethylene and polypropylene film, respectively, after 48 weeks of storage under high-temperature conditions. These values were later increased due to hydrolysis. This study presents the changes in composition and content of two soybean flour types and the changes in quality and stability of fatty acids in response to storage temperature and duration. This study shows the influence of storage conditions and temperature on the nutritional quality which is least affected by packing material.


Assuntos
Ração Animal , Ácidos Graxos/química , Farinha/análise , Soja/química , Ácidos Graxos/classificação , Ácidos Graxos/isolamento & purificação , Temperatura Alta , Ácido Linoleico/química , Ácido Linoleico/isolamento & purificação , Valor Nutritivo , Ácido Oleico/química , Ácido Oleico/isolamento & purificação , Ácido Palmítico/química , Ácido Palmítico/isolamento & purificação , Ácidos Esteáricos/química , Ácidos Esteáricos/isolamento & purificação , Temperatura Ambiente , Ácido alfa-Linoleico/química , Ácido alfa-Linoleico/isolamento & purificação
17.
J Agric Food Chem ; 66(41): 10729-10740, 2018 Oct 17.
Artigo em Inglês | MEDLINE | ID: mdl-30145885

RESUMO

Increasing evidence has demonstrated the benefits of α-linolenic acid-rich flaxseed oil (ALA-FO) against lipid metabolism abnormality in both rodent models and humans. However, the metabolic response of FO to insulin resistance and type 2 diabetes is still inconsistent. This study aimed to explore the effect of FO on chronic high fat diet (HFD)-induced hepatic steatosis, insulin resistance, and inflammation, mainly focusing on hepatic n-3 fatty acid remodeling and endoplasmic reticulum (ER) unfolded protein response. The results showed that lard-based HFD feeding for 16 weeks (60% fat-derived calories) induced whole-body insulin resistance, lipid profile abnormality, and inflammation in mice, which was alleviated by FO in a dose-dependent manner. Moreover, FO effectively improved hepatic steatosis and insulin resistance in mice by modulating the specific location of ALA and its long-chain n-3 fatty acids across hepatic lipid fractions and enhancing insulin-stimulated phosphorylation of hepatic insulin receptor subtract-1 (IRS-1) tyrosine 632 and protein kinase B (AKT) ( p < 0.05). Importantly, the differential depositions of ALA and its long-chain n-3 fatty acids in plasma and ER membranes were observed, concomitant with the rescued ER unfolded protein response and Jun N-terminal kinase (JNK) signaling in mice liver.


Assuntos
Estresse do Retículo Endoplasmático/efeitos dos fármacos , Fígado Gorduroso/tratamento farmacológico , Resistência à Insulina/fisiologia , Óleo de Semente do Linho/química , Ácido alfa-Linoleico/química , Animais , Diabetes Mellitus Tipo 2/metabolismo , Dieta Hiperlipídica/efeitos adversos , Ácidos Graxos/metabolismo , Humanos , Inflamação/tratamento farmacológico , Proteínas Substratos do Receptor de Insulina/metabolismo , Óleo de Semente do Linho/uso terapêutico , Metabolismo dos Lipídeos/efeitos dos fármacos , Fígado/metabolismo , MAP Quinase Quinase 4/metabolismo , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Proteínas Proto-Oncogênicas c-akt/metabolismo , Transdução de Sinais/efeitos dos fármacos , Resposta a Proteínas não Dobradas/efeitos dos fármacos , Ácido alfa-Linoleico/uso terapêutico
18.
Int J Parasitol ; 48(11): 833-844, 2018 09.
Artigo em Inglês | MEDLINE | ID: mdl-30031002

RESUMO

Parasitic helminths continue to pose problems in human and veterinary medicine, as well as in agriculture. Resistance to current anthelmintics has prompted the search for new drugs. Anthelmintic metabolites from medicinal plants could be good anthelmintic drug candidates. However, the compounds active against nematodes have not been identified in most medicinal plants with anthelmintic activity. In this study, we aimed to identify the active compounds against helminths in Warburgia ugandensis Sprague subspecies ugandensis (Canellaceae) and study the underlying mechanism of action. A bioassay-guided isolation of anthelmintic compounds from the plant was performed using a Caenorhabditis elegans (C. elegans) test model with a WMicrotracker instrument to monitor motility. Three active compounds were purified and identified by nuclear magnetic resonance and high resolution MS: warburganal (IC50: 28.2 ±â€¯8.6 µM), polygodial (IC50: 13.1 ±â€¯5.3 µM) and alpha-linolenic acid (ALA, IC50: 70.1 ±â€¯17.5 µM). A checkerboard assay for warburganal and ALA as well as polygodial and ALA showed a fractional inhibitory concentration index of 0.41 and 0.37, respectively, suggesting that polygodial and ALA, as well as warburganal and ALA, have a synergistic effect against nematodes. A preliminary structure-activity relationship study for polygodial showed that the α,ß-unsaturated 1,4-dialdehyde structural motif is essential for the potent activity. None of a panel of C. elegans mutant strains, resistant against major anthelmintic drug classes, showed significant resistance to polygodial, implying that polygodial may block C. elegans motility through a mechanism which differs from that of currently marketed drugs. Further measurements showed that polygodial inhibits mitochondrial ATP synthesis of C. elegans in a dose-dependent manner (IC50: 1.8 ±â€¯1.0 µM). Therefore, we believe that the underlying mechanism of action of polygodial is probably inhibition of mitochondrial ATP synthesis. In conclusion, polygodial could be a promising anthelmintic drug candidate worth considering for further development.


Assuntos
Anti-Helmínticos/farmacologia , Bioensaio/métodos , Caenorhabditis elegans/efeitos dos fármacos , Magnoliopsida/química , Extratos Vegetais/química , Sesquiterpenos/farmacologia , Animais , Anti-Helmínticos/química , Caenorhabditis elegans/ultraestrutura , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Células HEK293 , Humanos , Concentração Inibidora 50 , Camundongos , Estrutura Molecular , Células RAW 264.7 , Sesquiterpenos/química , Relação Estrutura-Atividade , Ácido alfa-Linoleico/química , Ácido alfa-Linoleico/farmacologia
19.
Eur J Pharm Biopharm ; 130: 66-70, 2018 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-29913272

RESUMO

Therapies for the treatment of Chronic Myeloid Leukemia and other leukemias are still limited for patients at advanced stages, which allow development of point mutations in the BCR-ABL fusion gene that render CML cells insensitive to therapies. An effective non-viral delivery system based on lipopolymers is described in this study to deliver specific siRNAs to CML cells for therapeutic gene silencing. The lipopolymer, based on the lipid α-linolenic acid (αLA) substitution on low molecular weight polyethyleneimine (PEI), was used to deliver siRNA against the BCR-ABL gene and, the resultant therapeutic effect was evaluated in in vitro and in vivo CML models. The study concluded that siRNA/PEI-αLA nanoparticles enabled silencing of the BCR-ABL gene and BCR-ABL protein, which consequently reduced growth on CML K562 cells in vitro and arrested the growth of localized tumors in a localized CML mouse model. The results from this study confirmed the potential use of lipopolymers as delivery systems and are encouraging for the future design of non-viral delivery systems for the treatment of CML and other hematological malignancies resulting from gene fusions.


Assuntos
Proteínas de Fusão bcr-abl/genética , Leucemia Mielogênica Crônica BCR-ABL Positiva/genética , Nanopartículas , RNA Interferente Pequeno/administração & dosagem , Animais , Inativação Gênica , Humanos , Células K562 , Leucemia Mielogênica Crônica BCR-ABL Positiva/terapia , Camundongos , Camundongos Nus , Mutação Puntual , Polietilenoimina/química , Polímeros/química , Interferência de RNA , Ensaios Antitumorais Modelo de Xenoenxerto , Ácido alfa-Linoleico/química
20.
J Agric Food Chem ; 66(26): 6917-6925, 2018 Jul 05.
Artigo em Inglês | MEDLINE | ID: mdl-29932339

RESUMO

Various active ingredients play a crucial role in providing and supplementing the nutritional requirements of organisms. In this work, we attempted to chemically manipulate the interfacial microstructure of oil-water microemulsions (ME) with carbon dots (CDs), concentrating on substantially enhancing the antioxidant capacity of α-linolenic acid (ALA). To this end, CDs were synthesized and introduced into an ME. The molecular interaction of surfactant with CDs was investigated by Fourier-transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR). The microstructure of the ME was monitored by transmission electron microscopy (TEM) and cryo-electron microscopy (cryo-EM). The cryo-EM result showed the oil-water interface in the ME was better defined after the CDs were loaded, and 1H NMR proved the CDs were distributed mainly at the interface. On the basis of these results, interfacial models were proposed. Final evaluation results demonstrated the stabilizing effect and oxidation-inhibition ability of the ALA-loaded ME was substantially enhanced after the introduction of the CDs, indicating a "turn off" effect of the interface. Interestingly, CDs do not affect the in vitro release of ALA, indicating a "turn on" effect of the interface. This work provided a successful interface manipulation with a nanocarrier that can be used for a large diversity of food nutraceuticals.


Assuntos
Antioxidantes/química , Óleos/química , Ácido alfa-Linoleico/química , Carbono/química , Emulsões/química , Espectroscopia de Ressonância Magnética , Espectroscopia de Infravermelho com Transformada de Fourier , Água/química
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