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1.
Food Funct ; 12(5): 2171-2188, 2021 Mar 07.
Artigo em Inglês | MEDLINE | ID: mdl-33566044

RESUMO

The present study was designed to explore the beneficial mitochondrial effects and anti-oxidative activities of plant sterol ester of α-linolenic acid (PS-ALA) through AMP-activated protein kinase (AMPK) signaling in the treatment of nonalcoholic fatty liver disease (NAFLD) using in vivo and in vitro models. The mitochondrial function was evaluated and the oxidative stress index was measured. The protein expression was analyzed by immunohistochemical, immunofluorescence, and western blotting methods. The results showed that PS-ALA significantly suppressed NAFLD and alleviated steatosis in HepG2 cells induced by oleic acid (OA). In addition, PS-ALA promoted mitochondrial biogenesis, enhanced mitochondrial fatty acid oxidation capacity, improved mitochondrial dynamics, and restored mitochondrial membrane potential. Moreover, PS-ALA reduced reactive oxygen species production both in the liver tissue of HFD-fed mice and OA-loaded HepG2 cells. At the molecular level, PS-ALA accelerated the phosphorylation of AMPK and increased the protein expression of peroxisome proliferator-activated receptor-γ co-activator 1α (PGC-1α) and nuclear NF-E2-related factor 2 (Nrf2). Furthermore, the stimulating effects of PS-ALA on the PGC-1α/Nrf1/Tfam pathway and Nrf2/HO-1 pathway as well as its mitochondrial biogenesis promotion effects and anti-oxidative activities were abrogated by the AMPK inhibitor in OA-treated HepG2 cells. In conclusion, the protective effects of PS-ALA on NAFLD appear to be associated with improving mitochondrial function and oxidative stress via activating AMPK signaling.


Assuntos
Proteínas Quinases Ativadas por AMP/metabolismo , Ésteres/uso terapêutico , Hepatopatia Gordurosa não Alcoólica/tratamento farmacológico , Estresse Oxidativo/efeitos dos fármacos , Fitosteróis/uso terapêutico , Ácido alfa-Linoleico/química , Animais , Dieta Hiperlipídica , Ativação Enzimática/efeitos dos fármacos , Ésteres/química , Células Hep G2 , Humanos , Fígado/química , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Mitocôndrias Hepáticas/efeitos dos fármacos , Mitocôndrias Hepáticas/fisiologia , Mitocôndrias Hepáticas/ultraestrutura , Hepatopatia Gordurosa não Alcoólica/etiologia , Hepatopatia Gordurosa não Alcoólica/fisiopatologia , Fosforilação , Fitosteróis/química , Espécies Reativas de Oxigênio/análise , Transdução de Sinais/efeitos dos fármacos
2.
Molecules ; 26(1)2020 Dec 28.
Artigo em Inglês | MEDLINE | ID: mdl-33379293

RESUMO

Olives affected by active and damaging infestation (olive fruit fly Bactrocera oleae (Rossi)) were assayed for their chemical composition. Biophenols were determined by HPLC, sterols, triterpenic dialcohols, and fatty acids by gas chromatography analysis. The acquired data were statistically analyzed. Oils produced from "Istrska belica" fruit affected by active infestation compared to the oils made from fruit affected by damaging infestation showed higher amounts of total oleuropein biofenols (377.3 versus (vs.) 106.6 mg/kg), total biophenols (755 vs. 377 mg/kg), lignans (85.3 vs. 32.9 mg/kg), the dialdehydic form of decarboxymethyl oleuropein aglycone (DMO-Agl-dA) (148.3 vs. 49.0 mg/kg), its oxidized form (DMO-Agl-dA)ox (35.2 vs. 8.5 mg/kg), the dialdehydic form of oleuropein aglycone (O-Agl-dA) (61.1 vs. 8.0 mg/kg), the dialdehydic form of ligstroside aglycone (L-Agl-dA) (63.5 vs. 28.0 mg/kg), the aldehydic form of oleuropein aglycone (O-Agl-A) (40.6 vs. 8.4 mg/kg), and lower amounts of tyrosol (Tyr) (6.0 vs. 13. 9 mg/kg) and the aldehydic form of ligstroside aglycone (L-Agl-A) (13.8 vs. 40.3 mg/kg). Higher values of stigmasterol (2.99%) and lower values of campesterol (2.25%) were determined in oils affected by damaging infestation; an increase in triterpenic dialcohols was also observed (3.04% for damaging and 1.62% for active infestation). Oils affected by damaging infestation, compared to active infestation, showed lower amounts of oleic acid (73.89 vs. 75.15%) and higher amounts of myristic (0.013 vs. 0.011%), linoleic (7.27 vs. 6.48%), and linolenic (0.74 vs. 0.61%) acids.


Assuntos
Infecções/metabolismo , Olea/química , Olea/metabolismo , Olea/parasitologia , Azeite de Oliva/química , Azeite de Oliva/metabolismo , Tephritidae/fisiologia , Animais , Infecções/parasitologia , Ácido Linoleico/química , Ácido Mirístico/química , Ácido Oleico/química , Fenóis/química , Ácido alfa-Linoleico/química
3.
J Food Sci ; 85(4): 1160-1166, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-32125697

RESUMO

The effect of chemical refining process on the bioactive composition, in vitro antioxidant capacity, and their correlation of perilla seed oil (PSO) were investigated. In this paper, seven samples corresponding to each step of the refining process (degumming, neutralization, bleaching, deodorization, winterization, crude, and refined oils) were studied. The results showed that phenolic compounds and tocopherols were removed from PSO to a degree of 19.4% and 5.4%, respectively. In addition, the carotenoid content of PSO decreased during the refining process. The main carotenoid of PSO was found to be lutein, and the compound was lost completely during the bleaching step of the refining process. In this paper, we analyzed the variation of carotenoid content in PSO during the refining process for the first time. Neutralization affected the contents of phytosterols the most, followed by the effects of degumming and bleaching. The demonstrated results of Pearson product-moment correlation indicated that total tocopherols were significantly correlated with the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and oxygen radical absorption capacity (ORAC) values, whereas carotenoids were significantly correlated with the DPPH value. However, phenolic compounds and phytosterols have no significant difference with DPPH, 2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt, ORAC, and ferric reducing antioxidant power values. The collected information can be applied to seeking out optimum factors needed to suffice the fundamental requirements for PSO production and minimize micronutrient losses to enhance its market value. PRACTICAL APPLICATION: The present study aimed to determine influence of chemical refining in the bioactive composition of perilla seed oil (PSO) as well as its antioxidant capacity in vitro. Moreover, we also intend to find the correlation between them. Results indicated that this study supplies a good reference for the industrial parameters of the refining process to minimize micronutrient losses and further obtain high-quality PSO products for consumers.


Assuntos
Antioxidantes/química , Manipulação de Alimentos/métodos , Perilla/química , Ácido alfa-Linoleico/química , Carotenoides/química , Micronutrientes/química , Fenóis/análise , Fitosteróis/química , Óleos Vegetais/química , Sementes/química , Tocoferóis/química
4.
Mar Drugs ; 18(2)2020 Feb 12.
Artigo em Inglês | MEDLINE | ID: mdl-32059424

RESUMO

One of the essential fatty acids with therapeutic impacts on human health is known to be omega-3 polyunsaturated fatty acids (PUFA). More lately, ionic liquids (ILs) have received significant attention among scientists in overcoming the disadvantages of traditional solvents in biomass lipid extraction. However, the large pool of cations and anions possibly accessible will lead to a growing number of innovatively synthesized ILs. Nevertheless, the exhaustive measurement of all these systems is economically impractical. The conductive screening model for real solvents (COSMO-RS) is considered a precious approach with the availability of a few models to predict the characteristics of ILs. This work introduces the estimate of capacity values at infinite dilution for a range of ILs using COSMO-RS software as part of solid-liquid extraction. This favorable outcome presented that the capacity values of the IL molecules are extremely dependent on both anions and cations. Among the 352 combinations of cation/anion tested, short alkyl chain cations coupled with inorganic anions were found to be most efficient and therefore superior in the extraction method. Sulphate-, chloride-, and bromide-based ILs were found to have higher extraction capacities in contrast with the remainders, while propanoate revealed an extraordinary capacity when combined with ethyl-based cations. Eventually, the predicted results from COSMO-RS were validated through the experimentally calculated extraction yield of alpha-linolenic acid (ALA) compound from Nannochloropsis sp. microalgae. Three selected ILs namely [EMIM][Cl], [TMAm][Cl], and [EMPyrro][Br] were selected from COSMO-RS for empirical extraction purpose and the validation results pinpointed the good prediction capability of COSMO-RS.


Assuntos
Líquidos Iônicos/química , Microalgas/química , Ácido alfa-Linoleico/química , Ânions/química , Cátions/química , Química Computacional , Íons/química , Modelos Moleculares , Estrutura Molecular , Temperatura , Termodinâmica
5.
Enzyme Microb Technol ; 132: 109388, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31731951

RESUMO

Conjugated linolenic acid (CLA) has important health effects, and their phospholipids forms (PL) are advantageous vehicles of this bioactive agent. Acidolysis of soybean phosphatidylcholine (PC) with conjugated linolenic acid (CLA) catalyzed by Lecitase® Ultra immobilized on Duolite A658 was studied. This reaction is typically limited by hydrolysis, producing 60-90 % of lyso- and glycero-PC and yielding low the process efficiency. Drying the amphiphilic PC material was found the key factor for maximal diacylglycerol phosphatidylcholines (PC) production and different drying approaches were studied to maximize the formation of PC rich in CLA in a solvent free process. PC lyophilization for 24 h getting dry solid appearance (PC; 783 ±â€¯11 mg water/Kg PC) or other standard protocols to reduce water content/activity of reaction medium, did not improve the reaction performance. However, adding 4 extra days to the second step of lyophilization at high vacuum (1 Pa) and moderate temperature (20 °C), followed by further PC dehydration with molecular sieves, drastically reduced the hydrolysis process by achieving a extensive PC dehydration (279 ±â€¯4 mg water/Kg PC), obtaining for the first time >99% molar yield of diacyl-PC product. After 24 h of reaction, a diacyl-PC product with 72.3% CLA content was obtained. PC molecules containing two CLA were the major species formed.


Assuntos
Enzimas Imobilizadas/química , Liofilização/métodos , Fosfolipases/química , Fosfolipídeos/química , Catálise , Hidrólise , Fosfatidilcolinas/química , Pró-Fármacos , Ácido alfa-Linoleico/química
6.
J Chromatogr A ; 1610: 460540, 2020 Jan 11.
Artigo em Inglês | MEDLINE | ID: mdl-31543337

RESUMO

Silver magnetic amino silicone adhesive (Fe3O4@SiO2@NH2@Ag) particles were prepared for the purification of α-linolenic acid from tree peony seed oil under applied magnetic field. First, Fe3O4@SiO2@NH2@Ag particles were prepared and physicochemically characterized, including XRD, TG, FTIR, SEM, magnetic hysteresis curves and elemental analysis. The static process for the purification of α-linolenic acid using Fe3O4@SiO2@NH2@Ag particles was investigated, including adsorption curve, desorption curve, elution solvent composition and adsorption isotherm. The result indicated that 0-1-4% acetone-n-hexane elution solvent was selected for the gradient elution process, 2 h and 60 min were the time required to reach adsorption and desorption equilibrium, 20 °C was selected as the adsorption temperature, Langmuir model was suitable to fit and explain the equilibrium data, and the adsorption process was spontaneous and exothermic. Under applied magnetic field, the dynamic process for the purification of α-linolenic acid using Fe3O4@SiO2@NH2@Ag particles was investigated, and the optimum conditions were 20:1 µL/g loading amount, 0.5 mL/min flow rate and 51.73 Oe magnetic field intensity. After purification, the purity and recovery ratio of α-linolenic acid were calculated to be 94% and 74%, respectively. Furthermore, the recycled Fe3O4@SiO2@NH2@Ag particles still achieved better purification result. Therefore, the developed method shows a good application prospect in the field of separation and purification of α-linolenic acid.


Assuntos
Nanopartículas de Magnetita/química , Paeonia/química , Silicones/química , Prata/química , Ácido alfa-Linoleico , Adesivos , Campos Magnéticos , Óleos Vegetais/química , Sementes/química , Ácido alfa-Linoleico/análise , Ácido alfa-Linoleico/química , Ácido alfa-Linoleico/isolamento & purificação , Ácido alfa-Linoleico/metabolismo
7.
J Chromatogr A ; 1609: 460461, 2020 Jan 04.
Artigo em Inglês | MEDLINE | ID: mdl-31445805

RESUMO

α-Linolenic acid (ALA) and its most important positional isomer γ-linolenic acid (GLA), are essential fatty acids (vitamin F). Therefore, ALA- and GLA-rich edible oils hold great potential in human and animal nutrition, as well as in nutraceutics and cosmetics. Quality control and nutritional validation of oil products is thus of increasing importance. In the present study, the cellulose tris(3,5-dichlorophenylcarbamate)-based chiral stationary phase was successfully used for separation of ALA and GLA, a major challenge in the liquid chromatography of these isomers. The chromatographic conditions were firstly optimized on a HPLC system with UV detection, and the use of a reversed-phase eluent system made up of aqueous 10 mM ammonium acetate/acetonitrile (40/60, v/v; wspH6.0) with a 25 °C column temperature resulted optimal for the simultaneous discrimination of the two isomers at a 0.5 mL/min flow rate (α = 1.10; RS = 1.21). The method was then optimized for LC-MS/MS implementation. The proposed innovative separation method holds a great potential for the quantification of ALA and GLA in food and biological matrices, thus opening the way to further investigations involving the two positional isomers.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Ácido alfa-Linoleico/isolamento & purificação , Ácido gama-Linolênico/isolamento & purificação , Celulose/análogos & derivados , Celulose/química , Cromatografia Líquida de Alta Pressão/instrumentação , Humanos , Isomerismo , Fenilcarbamatos/química , Espectrometria de Massas em Tandem , Temperatura , Ácido alfa-Linoleico/química , Ácido gama-Linolênico/química
8.
Sci Rep ; 9(1): 14296, 2019 10 04.
Artigo em Inglês | MEDLINE | ID: mdl-31586098

RESUMO

Hevea brasiliensis remains the primary crop commercially exploited to obtain latex, which is produced from the articulated secondary laticifer. Here, we described the transcriptional events related to jasmonic acid (JA)- and linolenic acid (LA)-induced secondary laticifer differentiation (SLD) in H. brasiliensis clone RRIM 600 based on RNA-seq approach. Histochemical approach proved that JA- and LA-treated samples resulted in SLD in H. brasiliensis when compared to ethephon and untreated control. RNA-seq data resulted in 86,614 unigenes, of which 2,664 genes were differentially expressed in JA and LA-induced secondary laticifer harvested from H. brasiliensis bark samples. Among these, 450 genes were unique to JA and LA as they were not differentially expressed in ethephon-treated samples compared with the untreated samples. Most transcription factors from the JA- and LA-specific dataset were classified under MYB, APETALA2/ethylene response factor (AP2/ERF), and basic-helix-loop-helix (bHLH) gene families that were involved in tissue developmental pathways, and we proposed that Bel5-GA2 oxidase 1-KNOTTED-like homeobox complex are likely involved in JA- and LA-induced SLD in H. brasiliensis. We also discovered alternative spliced transcripts, putative novel transcripts, and cis-natural antisense transcript pairs related to SLD event. This study has advanced understanding on the transcriptional regulatory network of SLD in H. brasiliensis.


Assuntos
Hevea/metabolismo , Látex/metabolismo , Proteínas de Plantas/metabolismo , Fatores de Transcrição/metabolismo , Ciclopentanos/química , Regulação da Expressão Gênica de Plantas , Genes de Plantas , Hevea/genética , Compostos Organofosforados/química , Oxilipinas/química , Proteínas de Plantas/genética , Fatores de Transcrição/genética , Ácido alfa-Linoleico/química
9.
Future Med Chem ; 11(20): 2647-2662, 2019 10.
Artigo em Inglês | MEDLINE | ID: mdl-31621420

RESUMO

Aim: To encapsulate amphotericin B (AmB) with reduced toxicity and comparable activity. Results & methodology: The α-linolenic acid (ALA)-modified monomethoxy polyethylene glycol-g-PEI-g-ALA conjugate was employed to prepare AmB-loaded micelles (AmB-M). In vitro activity and release behavior of AmB-M were investigated. AmB-M enhanced AmB's water-solubility to 1.2 mg/ml, showing good storage stability. AmB-M could achieve a sustained and slow release of AmB, low hemolysis activity and negligible kidney toxicity when compared with commercial AmB injection. Antifungal activity and biofilm inhibition experiments confirmed that the antifungal activity of AmB-M against Candida albicans was similar to that of AmB injection. Conclusion: Monomethoxy polyethylene glycol-g-PEI-g-ALA micelles could be a preferable choice to treat systemic fungal infections as an efficient drug delivery system.


Assuntos
Anfotericina B/química , Antifúngicos/química , Composição de Medicamentos , Micelas , Polietilenoglicóis/química , Ácido alfa-Linoleico/química , Anfotericina B/efeitos adversos , Anfotericina B/farmacologia , Animais , Antifúngicos/efeitos adversos , Antifúngicos/farmacologia , Biofilmes/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Hemólise/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana
10.
Int J Mol Sci ; 20(21)2019 Oct 28.
Artigo em Inglês | MEDLINE | ID: mdl-31661847

RESUMO

Grain number per panicle is an important component of grain yield in sorghum (Sorghum bicolor (L.)) and other cereal crops. Previously, we reported that mutations in multi-seeded 1 (MSD1) and MSD2 genes result in a two-fold increase in grain number per panicle due to the restoration of the fertility of the pedicellate spikelets, which invariably abort in natural sorghum accessions. Here, we report the identification of another gene, MSD3, which is also involved in the regulation of grain numbers in sorghum. Four bulked F2 populations from crosses between BTx623 and each of the independent msd mutants p6, p14, p21, and p24 were sequenced to 20× coverage of the whole genome on a HiSeq 2000 system. Bioinformatic analyses of the sequence data showed that one gene, Sorbi_3001G407600, harbored homozygous mutations in all four populations. This gene encodes a plastidial ω-3 fatty acid desaturase that catalyzes the conversion of linoleic acid (18:2) to linolenic acid (18:3), a substrate for jasmonic acid (JA) biosynthesis. The msd3 mutants had reduced levels of linolenic acid in both leaves and developing panicles that in turn decreased the levels of JA. Furthermore, the msd3 panicle phenotype was reversed by treatment with methyl-JA (MeJA). Our characterization of MSD1, MSD2, and now MSD3 demonstrates that JA-regulated processes are critical to the msd phenotype. The identification of the MSD3 gene reveals a new target that could be manipulated to increase grain number per panicle in sorghum, and potentially other cereal crops, through the genomic editing of MSD3 functional orthologs.


Assuntos
Produtos Agrícolas/enzimologia , Ciclopentanos/metabolismo , Ácidos Graxos Dessaturases/genética , Ácidos Graxos Dessaturases/metabolismo , Oxilipinas/metabolismo , Sorghum/enzimologia , Alelos , Produtos Agrícolas/efeitos dos fármacos , Produtos Agrícolas/genética , Produtos Agrícolas/crescimento & desenvolvimento , Ciclopentanos/farmacologia , Grão Comestível/efeitos dos fármacos , Grão Comestível/genética , Grão Comestível/crescimento & desenvolvimento , Sequenciamento de Nucleotídeos em Larga Escala , Ácido Linoleico/química , Ácido Linoleico/metabolismo , Mutação , Oxilipinas/farmacologia , Fenótipo , Sementes/efeitos dos fármacos , Sementes/genética , Sementes/crescimento & desenvolvimento , Sorghum/genética , Sorghum/metabolismo , Ácido alfa-Linoleico/biossíntese , Ácido alfa-Linoleico/química
11.
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
12.
J Control Release ; 310: 141-154, 2019 09 28.
Artigo em Inglês | MEDLINE | ID: mdl-31430499

RESUMO

Despite development of effective tyrosine kinase inhibitors for treatment of chronic myeloid leukemia (CML), some patients do not effectively respond to the therapy and can display resistance in response to the drug therapy. To develop an alternative approach to CML therapy, we are exploring siRNA mediated silencing of the primary CML oncogene, BCR-ABL, by using non-viral (polymeric) delivery systems. In this study, a group of lipopolymers derived from low molecular PEIs substituted with linoleic acid (LA), α-linolenic acid (αLA) and cholesterol (Chol) was investigated for the first time for siRNA delivery to CML primary samples. The delivery efficiency in primary cells was equivalent to CML K562 cell line, and the lipopolymers gave effective internalization of siRNA depending on the nature of lipid substituent. The PEI-αLA (2.5 αLA/PEI), PEI-Chol (2.2 Chol/PEI), and PEI-LA (2.6 LA/PEI) lipopolymers used as BCR-ABL siRNA carriers (at 60 nM siRNA) reduced the BCR-ABL mRNA expression by 17% to 45%, and inhibited the formation of colonies by 24% to 41% in comparison with control siRNA in mononuclear cells. BCR-ABL siRNA treatment reduced the BCR-ABL mRNA expression by 50% in one of two CD34+ samples tested, and combination of BCR-ABL siRNA with imatinib (IM) treatment decreased the colony formation by 65% in one of two samples evaluated. The fact that no single polymer was universally effective in all patient samples may suggest patient-to-patient variability in terms of therapeutic responses to siRNA therapy. These results showed that a low dose of BCR-ABL siRNA could be used with lipopolymers to reduce BCR-ABL mRNA expression, CML cell survival and colony formation. This proof of principle study in CML primary cells can be applied to silencing of other therapeutic targets besides BCR-ABL and a study with larger patient samples is warranted for better identification of effective siRNA carriers.


Assuntos
Portadores de Fármacos/química , Proteínas de Fusão bcr-abl/genética , Inativação Gênica , Leucemia Mielogênica Crônica BCR-ABL Positiva/terapia , Lipídeos/química , Polietilenoimina/química , RNA Interferente Pequeno , Técnicas de Cultura de Células , Linhagem Celular Tumoral , Colesterol/química , Feminino , Humanos , Células K562 , Leucemia Mielogênica Crônica BCR-ABL Positiva/genética , Leucemia Mielogênica Crônica BCR-ABL Positiva/patologia , Masculino , Microscopia Confocal , RNA Interferente Pequeno/administração & dosagem , RNA Interferente Pequeno/genética , Ácido alfa-Linoleico/química
13.
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
14.
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 , Ácido alfa-Linoleico/metabolismo , gama-Ciclodextrinas/metabolismo
15.
Microbiology (Reading) ; 165(7): 772-778, 2019 07.
Artigo em Inglês | MEDLINE | ID: mdl-31100055

RESUMO

To investigate the metabolism of 18:2n-6 and 18:3n-3 by pure cultures of Sharpea azabuensis, two different strains (RL 1 and ST18) were each incubated in the presence of 40 µg ml-1 18:2n-6 or 18:3n-3. Pure cultures of Butyrivibriofibrisolvens D1 and Butyrivibrio proteoclasticus P18 were included as control treatments. Similar to the metabolism of B. fibrisolvens, both S. azabuensis strains converted 18:2n-6 or 18:3n-3 to cis-9, trans-11 CLA or cis-9, trans-11, cis-15 CLnA, after which it was further reduced to trans-11 18:1 or trans-11, cis-15 18:2, respectively. B. proteoclasticus additionally reduced trans-11 18:1 to 18:0. Trans-11, cis-15 18:2 was also further metabolized by B. proteoclasticus, although trans-11 18:1 did not accumulate, and only minor amounts of 18:0 were formed. The time frame of 18:2n-6 and 18:3n-3 biohydrogenation by S. azabuensis was comparable with B. fibrisolvens, indicating that S. azabuensis and B. fibrisolvens might be alternative biohydrogenators of 18:2n-6 and 18:3n-3 in the rumen.


Assuntos
Lactobacillaceae/metabolismo , Ácido Linoleico/metabolismo , Rúmen/microbiologia , Ácido alfa-Linoleico/metabolismo , Animais , Butyrivibrio/química , Butyrivibrio/genética , Butyrivibrio/metabolismo , Bovinos/microbiologia , Cavalos/microbiologia , Lactobacillaceae/química , Lactobacillaceae/genética , Ácido Linoleico/química , Estrutura Molecular , Ácido alfa-Linoleico/química
16.
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
17.
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
18.
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
19.
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
20.
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
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