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1.
Molecules ; 26(3)2021 Jan 21.
Artículo en Inglés | MEDLINE | ID: mdl-33494317

RESUMEN

Obesity is a major risk factor for some metabolic disorders including type 2 diabetes. Enhancement of peroxisome proliferator-activated receptor (PPAR) γ, a master regulator of adipocyte differentiation, is known to increase insulin-sensitive small adipocytes. In contrast, decreased PPARγ activity is also reported to improve insulin resistance. We have previously identified erucic acid as a novel natural component suppressing PPARγ transcriptional activity. In this study, we investigated the effect of erucic acid-rich yellow mustard oil (YMO) on obese/diabetic KK-Ay mice. An in vitro luciferase reporter assay and mesenchymal stem cell (MSC) differentiation assay revealed that 25 µg/mL YMO significantly inhibited PPARγ transcriptional activity and differentiation of MSCs into adipocytes but promoted their differentiation into osteoblasts. In KK-Ay mice, dietary intake of 7.0% (w/w) YMO significantly decreased the surrogate indexes for insulin resistance and the infiltration of macrophages into adipose tissue. Furthermore, 7.0% YMO increased bone mineral density. These results suggest that YMO can ameliorate obesity-induced metabolic disorders.


Asunto(s)
Diferenciación Celular/efectos de los fármacos , Ácidos Erucicos , Resistencia a la Insulina , Células Madre Mesenquimatosas/metabolismo , Planta de la Mostaza/química , Aceites de Plantas/química , Tejido Adiposo/metabolismo , Animales , Línea Celular , Ácidos Erucicos/química , Ácidos Erucicos/farmacología , Haplorrinos , Macrófagos/metabolismo , Masculino , Ratones , Ratones Obesos
2.
Nat Prod Res ; 35(3): 413-420, 2021 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-31311318

RESUMEN

Tadehagi triquetrum (L.) H.Ohashi, also known as Desmodium triquetrum (Fabaceae) is the most important plant in the herbal remedies. The present study focus on the isolation, in-silico and in-vitro studies of the two alkaloids C1 (5-(4-[(methylcarbamoyl) amino]-2-oxopyrimidin-1(2H)-yl) tetrahydrofuran-2-yl) methyl methyl carbamate is novel alkaloid and C2 13-Docosenamide is a known alkaloid. The chemical structures of compounds have been elucidated based on comprehensive techniques like GCMS, IR and NMR. In order to know the molecular mechanisms for the two compounds, in silico molecular docking study has been performed. Both compounds have shown perfect binding affinity to the enzymes TNF α, IL-4, IL-13 and 5 LOX Enzyme. The compounds also exhibited comparable G-scores and Glide energy values in comparison with the standard dexamethasone. In addition both the compounds have been tested for in vitro antioxidant assay by using ABTS and DPPH method and the results were compared with standard ascorbic acid.


Asunto(s)
Alcaloides/química , Alcaloides/metabolismo , Fabaceae/química , Alcaloides/farmacología , Antioxidantes/química , Antioxidantes/farmacología , Simulación por Computador , Ácidos Erucicos/química , Ácidos Erucicos/farmacología , Cromatografía de Gases y Espectrometría de Masas , Interleucina-13/química , Interleucina-13/metabolismo , Interleucina-4/química , Interleucina-4/metabolismo , Espectroscopía de Resonancia Magnética , Simulación del Acoplamiento Molecular , Estructura Molecular , Extractos Vegetales/química , Raíces de Plantas/química , Pirimidinas/química , Factor de Necrosis Tumoral alfa/química , Factor de Necrosis Tumoral alfa/metabolismo
3.
Food Chem ; 330: 127265, 2020 Nov 15.
Artículo en Inglés | MEDLINE | ID: mdl-32540525

RESUMEN

Camelina oil is increasingly popular as consumption as oil. Erucic acid is an unwanted fatty acid in oil. First studies on several genotypes have shown that this oil contains varying amounts of eriuc acid. The aim of the study was to analyses content of eriuc acid in all genotypes camelina. Hypothesis was that the content of erucic acid in winter forms is lower than in spring ones. A field experiment with 65 spring genotypes and 9 winter genotypes of camelina was conducted in Poland from 2016 to 2018. The analyses based on two chromatographic methods, i.e. UPLC-DAD and GC-MS, showed no differences in the results for the camelina samples. The average percentage content of the erucic acid in the spring genotypes was 3.432%, and in the winter genotypes was 0.1%. Our three-year research shows that some winter varieties can be used as low erucic acid forms.


Asunto(s)
Brassicaceae/química , Aceites de Plantas/química , Brassicaceae/genética , Ácidos Erucicos/química , Genotipo , Polonia , Estaciones del Año , Semillas/química , Semillas/genética
4.
Curr Drug Deliv ; 17(4): 292-302, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-32039684

RESUMEN

BACKGROUND: Liposomes are mostly known to be prepared from phospholipids and lipids and have a remarkable capacity to encapsulate both lipophobic and lipophilic molecules. However, there is little research on developing fatty acid liposomes for chemotherapy. OBJECTIVE: We have successfully prepared mixed fatty acid liposomes from two monounsaturated fatty acids, namely oleic acid and erucic acid, which stabilised by DOPEPEG2000. The Critical Vesicular Concentration (CVC) of liposomes was found to be within 0.09 to 0.21 mmol dm-3, with an average particle size of 400 nm. METHODS: Encapsulation of various anticancer drugs such as folinic acid, methotrexate, doxorubicin, or irinotecan resulted in Encapsulation Efficiency (%EE) of up to 90%. Using a 3-(4, 5-dimethylthiazol-2- yl)-2,5-diphenyltetrazolium bromide (MTT) assay, the median Inhibitory Concentration (IC50) values of mixed oleic acid-erucic acid encapsulating hydrophilic drugs was remarkably reduced at the end of 24 hours of incubation with the human lung carcinoma cell line A549. RESULTS: The results suggest that mixed oleic acid-erucic acid liposomes are a potential new approach to further develop as an alternative vehicle of various drugs for cancer treatment.


Asunto(s)
Antineoplásicos/farmacología , Ácidos Erucicos/química , Liposomas/química , Ácido Oléico/química , Células A549 , Antineoplásicos/química , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Doxorrubicina/química , Doxorrubicina/farmacología , Portadores de Fármacos/química , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Irinotecán/química , Irinotecán/farmacología , Leucovorina/química , Leucovorina/farmacología , Metotrexato/química , Metotrexato/farmacología , Tamaño de la Partícula , Propiedades de Superficie
5.
Plant Biotechnol J ; 18(4): 983-991, 2020 04.
Artículo en Inglés | MEDLINE | ID: mdl-31553825

RESUMEN

Oilseed rape (Brassica napus) is the third largest source of vegetable oil globally. In addition to food uses, there are industrial applications that exploit the ability of the species to accumulate the very-long-chain fatty acid (VLCFA) erucic acid in its seed oil, controlled by orthologues of FATTY ACID ELONGASE 1 (Bna.FAE1.A8 and Bna.FAE1.C3). The proportion of polyunsaturated fatty acids (PUFAs) in rapeseed oil is predicted to affect its thermal stability and is controlled by orthologues of FATTY ACID DESATURASE 2, particularly Bna.FAD2.C5. Our aim was to develop rapeseed lines combining high erucic and low PUFA characters and to assess the impact on thermal stability of the oil they produce. The new type of rapeseed oil (high erucic low polyunsaturate; HELP) contained a substantially greater proportion of erucic acid (54%) compared with high erucic rapeseed oil (46%). Although the total VLCFA content was greater in oil from HELP lines (64%) than from high erucic rapeseed (57%), analysis of triacylglycerol composition showed negligible incorporation of VLCFAs into the sn-2 position. Rancimat analysis showed that the thermal stability of rapeseed oil was improved greatly as a consequence of reduction of PUFA content, from 3.8 and 4.2 h in conventional low erucic and high erucic rapeseed oils, respectively, to 11.3 and 16.4 h in high oleic low PUFA (HOLP) and HELP oils, respectively. Our results demonstrate that engineering of the lipid biosynthetic pathway of rapeseed, using traditional approaches, enables the production of renewable industrial oils with novel composition and properties.


Asunto(s)
Brassica napus/química , Ácidos Erucicos/química , Aceite de Brassica napus/química , Calor
6.
Int J Pharm ; 560: 205-218, 2019 Apr 05.
Artículo en Inglés | MEDLINE | ID: mdl-30742985

RESUMEN

There is an increasing demand for new lipidic biocompatible and safe materials for self-microemulsifying drug delivery system (SMEDDS). The present work reports the synthesis, characterization, oral mucosal irritation study, and application of novel erucic acid ester of G0-PETIM dendron based bicephalous heterolipid (BHL) as an oil phase in SMEDDS using Efavirenz (EFA), a BCS class II drug with poor water solubility and poor bioavailability. Studies were conducted to optimize EFA SMEDDS using different ratios of the BHL as oil phase and surfactant: co-surfactant weight ratios (Km). At Km (1.5), the microemulsion was spontaneously formed in water with mean globule size of 22.78 ±â€¯0.25 nm and polydispersity index (PDI) of 0.23 ±â€¯0.031 with high drug loading efficiency of 80.35 ±â€¯3.1%. Standard stability tests were performed on EFA SMEDDS and the results indicated it to be highly stable. The in vitro dissolution profile of EFA SMEDDS showed >95% of the drug release within an hour and expectedly substantial enhancement in in vivo bioavailability was observed; almost 6-fold increase in bioavailability with parameters Cmax 5.2 µg/mL, Tmax 3 h, and AUC(0-∞) 23.48 µg/h/mL respectively as compared the plain suspension of the drug. In conclusion, the BHL can be used effectively as an oil phase in SMEDDS to enhance solubility and bioavailability of BCS Class II drugs. Further, it holds, in general, a great promise as a new excipient for solubility and bioavailability enhancements.


Asunto(s)
Benzoxazinas/administración & dosificación , Sistemas de Liberación de Medicamentos , Excipientes/química , Lípidos/química , Alquinos , Animales , Área Bajo la Curva , Benzoxazinas/química , Benzoxazinas/farmacocinética , Disponibilidad Biológica , Química Farmacéutica/métodos , Ciclopropanos , Dendrímeros/química , Liberación de Fármacos , Emulsiones , Ácidos Erucicos/química , Masculino , Tamaño de la Partícula , Ratas , Ratas Wistar , Inhibidores de la Transcriptasa Inversa/administración & dosificación , Inhibidores de la Transcriptasa Inversa/química , Inhibidores de la Transcriptasa Inversa/farmacocinética , Solubilidad , Tensoactivos/química
7.
Chem Biol Interact ; 294: 107-117, 2018 Oct 01.
Artículo en Inglés | MEDLINE | ID: mdl-30142312

RESUMEN

BACKGROUND: PPAR-δ is a transcription factor which has crucial roles in stimulating oligodendroglial differentiation and myelination and its activation was also shown to differentiate malignant C6 glioma cells into oligodendrocytes. OBJECTIVE: One of the ligands of PPAR-δ is erucic acid (EA), an edible omega-9 fatty acid consumed more by Asian populations and exists highly in Chinese womens milk. There exist epidemiological evidence that pediatric brain tumor incidence is among the lowest in the Chinese population. EA is also an ingredient of Lorenzo's oil used against adrenoleukodystrophy, a pediatric demyelinating disease. EA was inappropriately assumed as a strong cardiotoxin based on Spanish oil syndrome, caused by toxic-aniline dye refined rapeseed oil. In this study, we studied whether EA is capable to block growth of C6 glioma cells and modify cardiotoxicity of doxorubicin. MATERIALS AND METHODS: We studied effects of EA on the 3-dimensional appearance of the adherent cells, soft agar colony formation and S-phase in the 3-dimensional spheroids in C6 glioma cell cultures. We also investigated the effects of EA on hepatic and cardiac toxicity of doxorubicin. RESULTS: EA decreased in vitro growth of C6 glioma cells at therapeutically achievable concentrations. EA effects were more prominent in 3D-assays (soft agar colonies and spheroids) and induced cell fusions in monolayer cultures. EA decreased S-phase inhibitory potency of doxorubicin (DOX), yet augmented its efficacy to induce a senescent morphology (as assessed by scanning electron microscopy) in monolayer and to increase iNOS and eNOS expression in spheroids. In our study, EA reduced DOX-induced necrosis in mice heart and liver and induced healthier morphology of heart mitochondria (as assessed by transmission electron microscopy); yet intercalated disks (ID) were more disturbed with DOX + EA. CONCLUSIONS: Both the antitumor and cardiac effects of EA may associate with the cell-to-cell contact mechanisms. Combining systemic EA with intrathecal DOX-chemotherapy via Ommaya reservoirs may reduce DOX concentrations in systemic circulation, hinder toxic interactions with EA and induce selective kill of glioma cells.


Asunto(s)
Proliferación Celular/efectos de los fármacos , Doxorrubicina/toxicidad , Ácidos Erucicos/farmacología , PPAR delta/metabolismo , Trioleína/química , Animales , Neoplasias Encefálicas/metabolismo , Neoplasias Encefálicas/patología , Línea Celular Tumoral , Combinación de Medicamentos , Ácidos Erucicos/química , Glioma/metabolismo , Glioma/patología , Corazón/efectos de los fármacos , Humanos , Hígado/efectos de los fármacos , Hígado/metabolismo , Hígado/patología , Masculino , Ratones , Ratones Endogámicos BALB C , Miocardio/metabolismo , Miocardio/patología , Óxido Nítrico Sintasa de Tipo II/metabolismo , Óxido Nítrico Sintasa de Tipo III/metabolismo , PPAR delta/química , Puntos de Control de la Fase S del Ciclo Celular/efectos de los fármacos , Esferoides Celulares/citología , Esferoides Celulares/efectos de los fármacos , Esferoides Celulares/metabolismo
8.
Appl Microbiol Biotechnol ; 101(19): 7271-7280, 2017 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-28812146

RESUMEN

Erucic acid (cis-docosa-13-enoic acid, C22:1∆13) and nervonic acid (cis-tetracosa-15-enoic acid, C24:1 ∆15) are important renewable feedstocks in plastic, cosmetic, nylon, and lubricant industries. Furthermore, nervonic acid is also applied to the treatment of some neurological diseases. However, the production of these two very long-chain fatty acids (VLCFA) is very limited as both are not present in the main vegetable oils (e.g., soybean, rapeseed, sunflower, and palm). Ectopic integration and heterologous expression of fatty acid elongases (3-ketoacyl-CoA synthases, KCS) from different plants in Rhodosporidium toruloides resulted in the de novo synthesis of erucic acid and nervonic acid in this oleaginous yeast. Increasing KCS gene copy number or the use of a push/pull strategy based on the expression of elongases with complementary substrate preferences increased significantly the amount of these two fatty acids in the microbial oils. Oil titers in 7-L bioreactors were above 50 g/L, and these two VLCFA represented 20-30% of the total fatty acids. This is the first time that microbial production of these types of oils is reported.


Asunto(s)
Ácidos Grasos Monoinsaturados/metabolismo , Microorganismos Modificados Genéticamente , Rhodotorula/metabolismo , Acetiltransferasas/genética , Acetiltransferasas/metabolismo , Reactores Biológicos , Ácidos Erucicos/química , Elongasas de Ácidos Grasos , Ácidos Grasos Monoinsaturados/química , Dosificación de Gen , Aceite de Palma/química , Aceites de Plantas/química , Aceite de Brassica napus/química , Rhodotorula/genética , Aceite de Soja/química , Aceite de Girasol/química
9.
Food Chem ; 173: 31-7, 2015 Apr 15.
Artículo en Inglés | MEDLINE | ID: mdl-25465991

RESUMEN

Overconsumption of erucic acid has been shown to cause heart damage in animals. The aim of this study is to evaluate the binding behaviour between erucic acid and bovine serum albumin using multi-spectroscopic methods and a molecular docking technique under physiological conditions. We find that erucic acid can quench the intrinsic fluorescence of BSA by dynamic quenching and there is a single class of binding site on BSA. In addition, the thermodynamic functions ΔH and ΔS are 119.14 kJ mol(-1) and 488.89 J mol(-1) K(-1), indicating that the hydrophobic force is a main acting force. Furthermore, the protein secondary structure changes with an increase in the content of α-helix, measured using synchronous fluorescence, circular dichroism and Fourier transform infrared spectroscopies. The molecular docking results illustrate that erucic acid can bind with the subdomain IIA of the BSA, and hydrogen bonding is also an acting force.


Asunto(s)
Ácidos Erucicos/química , Albúmina Sérica Bovina/química , Animales , Bovinos , Dicroismo Circular , Simulación del Acoplamiento Molecular/métodos , Unión Proteica , Espectroscopía Infrarroja por Transformada de Fourier/métodos
10.
Phys Chem Chem Phys ; 16(9): 4350-60, 2014 Mar 07.
Artículo en Inglés | MEDLINE | ID: mdl-24457621

RESUMEN

The ozone initiated heterogeneous oxidation of erucic acid (EA) thin film was investigated using a flow system combined with attenuated total reflection infrared spectroscopy (ATR-IR) over wide ranges of ozone concentrations (0.25-60 ppm), thin film thickness (0.1-1.0 µm), temperatures (263-298 K), and relative humidities (0-80% RH) for the first time. Pseudo-first-order rate constants, kapp, and overall reactive uptake coefficients, γ, were obtained through changes in the absorbance of C[double bond, length as m-dash]O stretching bands at 1695 cm(-1), which is assigned to the carbonyl group in carboxylic acid. Results showed that the reaction followed the Langmuir-Hinshelwood mechanism and kapp was largely dominated by surface reaction over bulk phase reaction. In addition, both the kapp and the γ values showed very strong temperature dependences (∼two orders of magnitude) over the temperature range; in contrast, they only slightly increased with increasing RH values from 0-80%. According to the kapp values as a function of temperature, the activation energy for the heterogeneous reaction was estimated to be 80.6 kJ mol(-1). Our results have suggested that heterogeneous reactions between ozone and unsaturated solid surfaces likely have a substantially greater temperature dependence than liquid ones. Moreover, the hygroscopic properties of EA thin films before and after exposure to ozone were also studied by measurement of water uptake. Based on the hygroscopicity data, the insignificant RH effect on reaction kinetics was probably due to the relatively weak water uptake by the unreacted and reacted EA thin films.


Asunto(s)
Ácidos Erucicos/química , Ozono/química , Cinética , Espectrofotometría Infrarroja , Temperatura , Agua/química , Humectabilidad
11.
Eur J Pharmacol ; 721(1-3): 208-14, 2013 Dec 05.
Artículo en Inglés | MEDLINE | ID: mdl-24076185

RESUMEN

Multidrug resistance (MDR) is a key element in the failure of chemotherapies, and development of agents to overcome MDR is crucial to improving cancer treatments. The overexpression of glutathione-S-transferases (GSTs) is one of the major mechanisms of MDR. Because some agents used in traditional Chinese medicine have strong antitumor effects coupled with low toxicity; we investigated the ability of N,N-bis(2-chloroethyl)docos-13-enamide (compound J), the synthesized analog of a highly unsaturated fatty acid from Isatis tinctoria L., to reverse the MDR induced by adriamycin (ADM) in TCA8113/ADM cells. We found that compound J significantly increased the cytotoxicity of ADM in TCA8113/ADM cells, with a reversal fold of 2.461. Analysis of the mechanisms through which compound J reversed MDR indicated that compound J significantly decreased the activity of GSTs and enhanced the depletion of GSH in TCA8113/ADM cells, but did not affect the P-glycoprotein (P-gp) efflux. Taken together, our data suggested that compound J was an excellent candidate for reversing MDR in cancer therapy.


Asunto(s)
Antineoplásicos/farmacología , Resistencia a Múltiples Medicamentos/efectos de los fármacos , Ácidos Erucicos/química , Ácidos Erucicos/farmacología , Ácidos Grasos/farmacología , Neoplasias de la Lengua/patología , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Doxorrubicina/farmacología , Glutatión/metabolismo , Glutatión Transferasa/metabolismo , Humanos
12.
Biochimie ; 95(1): 86-90, 2013 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-23009927

RESUMEN

Oxidative damage has been reported in Rett syndrome (RTT), a pervasive development disorder mainly caused up to 95% of cases by mutations in the X-linked methyl-CpG binding protein 2 (MeCP2) gene. We have recently synthesized F(2)-Dihomo-isoprostanes (F(2)-Dihomo-IsoP), peroxidation products from adrenic acid (C22:4 n - 6, AdA), a known component of myelin, and tested the potential value of F(2)-Dihomo-IsoPs as a novel disease marker and its relationship with clinical presentation, and disease progression. F(2)-Dihomo-IsoPs were determined by a gas chromatography/negative ion chemical ionization tandem mass spectrometry. The ent-7(RS)-F(2t)-Dihomo-IsoP and 17-F(2t)-Dihomo-IsoP were used as reference standards. The measured ions were the product ions at m/z 327 derived from the [M - 181](-) precursor ions (m/z 597) produced from both the derivatized ent-7(RS)-F(2t)-Dihomo-IsoP and 17-F(2t)-Dihomo-IsoP. Average plasma F(2)-Dihomo-IsoP levels in RTT were about 1 order of magnitude higher than in healthy controls, being higher in typical RTT as compared to RTT variants, with a remarkable increase of about 2 orders of magnitude in patients at the earliest stage of the disease followed by a steady decrease during the natural clinical progression. These data indicate for the first time that quantification of F(2)-Dihomo-IsoPs in plasma represents an early marker of the disease and may provide a better understanding of the pathogenic mechanisms behind the neurological regression in patients with RTT.


Asunto(s)
Biomarcadores/sangre , Encéfalo , F2-Isoprostanos , Proteína 2 de Unión a Metil-CpG , Síndrome de Rett , Encéfalo/efectos de los fármacos , Encéfalo/metabolismo , Encéfalo/patología , Ácidos Erucicos/química , Ácidos Erucicos/metabolismo , F2-Isoprostanos/administración & dosificación , F2-Isoprostanos/sangre , F2-Isoprostanos/síntesis química , F2-Isoprostanos/farmacocinética , Ácidos Grasos Insaturados , Humanos , Leucoencefalopatías/tratamiento farmacológico , Leucoencefalopatías/metabolismo , Leucoencefalopatías/patología , Peroxidación de Lípido/efectos de los fármacos , Proteína 2 de Unión a Metil-CpG/genética , Proteína 2 de Unión a Metil-CpG/metabolismo , Vaina de Mielina/química , Vaina de Mielina/patología , Estrés Oxidativo , Síndrome de Rett/sangre , Síndrome de Rett/diagnóstico , Síndrome de Rett/patología
13.
Biotechnol Bioeng ; 110(1): 78-86, 2013 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-22811287

RESUMEN

The enzymatic conversion of mixtures of multiple substrates was studied quantitatively, based on established methodology used for the enzymatic kinetic resolution of racemic mixtures, involving the use of competitive factors: ratios of specificity constants (k(cat)/K(M)) of substrate pairs. The competitive factors of the substrates were defined in relation to a reference substrate. These competitive factors were used to predict the composition of the reaction mixture as a function of the degree of conversion of the reaction. The methodology was evaluated using three different lipases to hydrolyze a model mixture of four fatty acid methyl esters and for the esterification of a mixture of the same fatty acids in free form with ethanol. In most cases, the competitive factors determined from the initial phase of the reactions predicted the product composition during the rest of the reaction very well. The slowest reacting fatty acid was erucic acid (both in free form and as methyl ester), which was thus enriched in the remaining substrate fraction, while the other fatty acids: lauric acid, palmitic acid and oleic acid were converted faster. Simulations of the compositions of reaction mixtures with different values of the competitive factors were carried out to provide an overview of what could be achieved using enzymatic enrichment. Possible applications include reactions involving homologous substrates and mixtures of multiple isomers. The analysis presented provides guidelines that can be useful in the screening and development of enzymes for enzymatic enrichment applications.


Asunto(s)
Ácidos Grasos/metabolismo , Lipasa/metabolismo , Biocatálisis , Biotecnología , Simulación por Computador , Ácidos Erucicos/química , Ácidos Erucicos/metabolismo , Ésteres/química , Ésteres/metabolismo , Ácidos Grasos/análisis , Hidrólisis , Cinética , Lipasa/química , Especificidad por Sustrato , Biología de Sistemas
14.
Macromol Rapid Commun ; 34(1): 47-50, 2013 Jan 11.
Artículo en Inglés | MEDLINE | ID: mdl-23161497

RESUMEN

Self-metathesis of erucic acid by [(PCy(3))(η-C-C(3)H(4)N(2)Mes(2))Cl(2)Ru = CHPh] (Grubbs second- generation catalyst) followed by catalytic hydrogenation and purification via the ester yields 1,26-hexacosanedioate (>99% purity). Polyesterification with 1,26-hexacosanediol, generated from the diester, affords polyester-26,26, which features a T(m) of 114 °C (T(c) = 92 °C, ΔH(m) = 160 J g(-1)). Ultralong-chain model polyesters-38,23 (T(m) = 109 °C) and -44,23 (T(m) = 111 °C), generated via multistep procedures including acyclic diene metathesis polymerization, underline that melting points of such aliphatic polyesters do not gradually increase with methylene sequence chain length. Available data suggest that to mimic linear polyethylenes thermal properties, even longer sequences, amounting to at least four times a fatty acid chain, fully incorporated in a linear fashion are required.


Asunto(s)
Poliésteres/química , Polietileno/química , Ácidos Erucicos/química , Hidrogenación , Modelos Químicos , Poliésteres/síntesis química , Polietileno/síntesis química , Polimerizacion , Temperatura de Transición
15.
Yao Xue Xue Bao ; 47(9): 1252-6, 2012 Sep.
Artículo en Chino | MEDLINE | ID: mdl-23227559

RESUMEN

This study is to observe preventive effect of (Z)-N-(2-hydroxyethyl) docos-13-enamide on hyperlipidemia and fatty liver of golden hamsters. Hyperlipidemic golden hamsters fed with high-fat diet was administered orally with (Z)-N-(2-hydroxyethyl) docos-13-enamide (10, 20 and 40 mg x kg(-1)) for 5 weeks. Levels of serum and hepatic lipid content, liver histology, hepatic MDA and SOD levels, serum ALT and AST levels were evaluated in golden hamsters. (Z)-N-(2-Hydroxyethyl) docos-13-enamide has a hypolipidemic effect, and could reduce hepatic lipid content, serum ALT and AST levels, hepatic MDA level, increase hepatic SOD activity. (Z)-N-(2-Hydroxyethyl) docos-13-enamide plays an important role in reducing serum lipid, restraining hepatic fatty deposition and protecting liver to get rid of peroxidation injury of hyperlipidemic golden hamsters. The exact lipid-lowering mechanism of (Z)-N-(2-hydroxyethyl) docos-13-enamide needs further investigation.


Asunto(s)
Ácidos Erucicos/farmacología , Hígado Graso , Hiperlipidemias , Hipolipemiantes/farmacología , Hígado , Alanina Transaminasa/sangre , Animales , Aspartato Aminotransferasas/sangre , Colesterol/sangre , Colesterol/metabolismo , HDL-Colesterol/sangre , LDL-Colesterol/sangre , Cricetinae , Ácidos Erucicos/química , Hígado Graso/sangre , Hígado Graso/metabolismo , Hígado Graso/patología , Hiperlipidemias/sangre , Hiperlipidemias/metabolismo , Hiperlipidemias/patología , Hipolipemiantes/química , Hígado/metabolismo , Hígado/patología , Masculino , Malondialdehído/metabolismo , Mesocricetus , Distribución Aleatoria , Superóxido Dismutasa/metabolismo , Triglicéridos/sangre , Triglicéridos/metabolismo
16.
J Oleo Sci ; 61(8): 421-6, 2012.
Artículo en Inglés | MEDLINE | ID: mdl-22864512

RESUMEN

Gas chromatography (GC) of docosenoic acid (22:1) has been performed for the separation of positional isomers on the novel SLB-IL100 column with a highly polar ionic liquid stationary phase. A test mixture of 22:1 methyl esters prepared from total lipids of flounder was subjected to GC on a 60 m×0.32 mm i.d. column at an isothermal temperature of 150°C-180°C. On this column, all five positional isomers separated in the elution order of 22:1n-15, 22:1n-13, 22:1n-11, 22:1n-9, and 22:1n-7. The positional isomers, 22:1n-15, 22:1n-13, and 22:1n-11, unresolvable on conventional polar polymer phase columns, were almost completely separated from each other within 24 min at 170°C. The equivalent chain length values of 22:1n-11 to 22:1n-7 were parallel to those on polyethylene glycol and cyanopropyl polysiloxane columns, whereas 22:1n-15 and 22:1n-13 were relatively lower and closer to saturated 22:0 acid. Similar findings were also obtained for co-injected 20:1n-15 to 20:1n-11 isomers. Analysis of fish 22:1 revealed that 22:1n-13 is not always a minor isomer, as previously reported for several samples. The results of this study confirm the view that SLB-IL100 is a powerful tool for GC analysis of monounsaturated fatty acids.


Asunto(s)
Ácidos Erucicos/química , Ácidos Erucicos/aislamiento & purificación , Cromatografía de Gases y Espectrometría de Masas/métodos , Líquidos Iónicos/química , Animales , Disulfuros/química , Ésteres/aislamiento & purificación , Aceites de Pescado/química , Isomerismo , Polímeros/química , Reproducibilidad de los Resultados
17.
Zhong Yao Cai ; 35(8): 1257-9, 2012 Aug.
Artículo en Chino | MEDLINE | ID: mdl-23320358

RESUMEN

OBJECTIVE: To study the chemical constituents from Patrinia scabra Bunge. METHODS: Chemical constituents were isolated and purified by silica gel and Sephadex LH-20 column chromatography. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. RESULTS: Seven compounds were isolated and purified. Their structures were identified as villosol (I), patriscabrol (II), protocatechuic acid (III), beta-daucosterol (IV), oleic acid (V), beta-sitosterol (VI), erucic acid (VII). CONCLUSION: Compounds I, III, V, VII are isolated from this plant for the first time.


Asunto(s)
Hidroxibenzoatos/química , Lactonas/aislamiento & purificación , Ácido Oléico/aislamiento & purificación , Patrinia/química , Plantas Medicinales/química , Ácidos Erucicos/química , Ácidos Erucicos/aislamiento & purificación , Hidroxibenzoatos/aislamiento & purificación , Lactonas/química , Estructura Molecular , Ácido Oléico/química , Raíces de Plantas/química , Rizoma/química , Solventes/química
18.
J Cell Biochem ; 112(5): 1329-36, 2011 May.
Artículo en Inglés | MEDLINE | ID: mdl-21312242

RESUMEN

In this research, a lipid-cationic polymer (LCP) containing the side-chain branching of brassidic acid was synthesized using chemical methods. As a gene vector for small interfering ribonucleic acid (siRNA) transfection, the efficiency and biosafety of LCP were preliminarily evaluated to investigate its possible application on tumor gene therapy. The toxicity, side-effects, and biosafety of LCP were investigated in animals based on the results of in vitro experiments. The siRNA against cyclooxygenase-2 (COX-2) was transfected by LCP to interfere with the COX-2 expression in nude-transplanted tumors. Hematoxylin and eosin stains, immunohistochemistry, reverse transcription-polymerase chain reaction, and Western blot were performed to evaluate the efficiency of LCP for siRNA transfection. The animal toxicity experiment showed that a high concentration of LCP had a low toxic effect on animals and did not induce allergic or pyrogenic reactions. The results from the in vivo transfection indicated that LCP could efficiently transfect siRNA and silence the target gene expression. The LCP gene vector for siRNA transfection is highly efficient during in vivo transfection and had low toxicity. From all aspects of tumor gene therapy and basic research, LCP is valuable for scientific research and medical applications.


Asunto(s)
Terapia Genética/métodos , Vectores Genéticos/efectos adversos , Lipopéptidos/efectos adversos , Nanopartículas/efectos adversos , Neoplasias/terapia , ARN Interferente Pequeño/genética , Animales , Ciclooxigenasa 2/genética , Ácidos Erucicos/efectos adversos , Ácidos Erucicos/química , Silenciador del Gen , Vectores Genéticos/química , Cobayas , Células HeLa , Humanos , Lipopéptidos/química , Masculino , Ratones , Ratones Desnudos , Nanopartículas/química , Neoplasias/enzimología , Conejos , Transfección
19.
Int J Biol Macromol ; 48(1): 137-45, 2011 Jan 01.
Artículo en Inglés | MEDLINE | ID: mdl-21035502

RESUMEN

Pseudomonas aeruginosa produced medium chain length poly(3-hydroxyalkanoates) (mcl-PHAs) when grown on substrates containing very long chain fatty acids (VLCFA, C>20). Looking for low cost carbon sources, we tested Brassica carinata oil (erucic acid content 35-48%) as an intact triglyceride containing VLCFA. Oleic (C18:1), erucic (C22:1), and nervonic (C24:1) acids were also employed for mcl-PHA production as model substrates. The polymers obtained were analyzed by GC of methanolyzed samples, GPC, 1H and 13C NMR, ESI MS of partially pyrolyzed samples, and DSC. The repeating units of such polymers were saturated and unsaturated, with a higher content of the latter in the case of the PHA obtained from B. carinata oil. Statistical analysis of the ion intensity in the ESI mass spectra showed that the PHAs from pure fatty acids are random copolymers, while the PHA from B. carinata oil is either a pure polymer or a mixture of polymers. Weight-average molecular weight varied from ca. 56,000 g/mol for the PHA from B. carinata oil and oleic acid, to about 120,000 g/mol for those from erucic and nervonic acids. The PHAs from erucic and nervonic acids were partially crystalline, with rubbery characteristics and a melting point (Tm) of 50°C, while the PHAs from oleic acid and from B. carinata oil afforded totally amorphous materials, with glass transition temperatures (Tg) of -52°C and -47°C, respectively.


Asunto(s)
Brassica/química , Ácidos Erucicos/metabolismo , Ácidos Grasos/metabolismo , Aceites de Plantas/química , Polihidroxialcanoatos/biosíntesis , Ácidos Erucicos/química , Ácidos Grasos Monoinsaturados/química , Ácidos Grasos Monoinsaturados/metabolismo , Hidrólisis , Espectroscopía de Resonancia Magnética , Polihidroxialcanoatos/química , Polihidroxialcanoatos/aislamiento & purificación , Pseudomonas aeruginosa/metabolismo , Espectrometría de Masa por Ionización de Electrospray , Temperatura
20.
Theor Appl Genet ; 122(6): 1091-103, 2011 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-21188349

RESUMEN

Oil content and oil quality fractions (viz., oleic, linoleic and linolenic acid) are strongly influenced by the erucic acid pathway in oilseed Brassicas. Low levels of erucic acid in seed oil increases oleic acid content to nutritionally desirable levels, but also increases the linoleic and linolenic acid fractions and reduces oil content in Indian mustard (Brassica juncea). Analysis of phenotypic variability for oil quality fractions among a high-erucic Indian variety (Varuna), a low-erucic east-European variety (Heera) and a zero-erucic Indian variety (ZE-Varuna) developed by backcross breeding in this study indicated that lower levels of linoleic and linolenic acid in Varuna are due to substrate limitation caused by an active erucic acid pathway and not due to weaker alleles or enzyme limitation. To identify compensatory loci that could be used to increase oil content and maintain desirable levels of oil quality fractions under zero-erucic conditions, we performed Quantitative Trait Loci (QTL) mapping for the above traits on two independent F1 doubled haploid (F1DH) mapping populations developed from a cross between Varuna and Heera. One of the populations comprised plants segregating for erucic acid content (SE) and was used earlier for construction of a linkage map and QTL mapping of several yield-influencing traits in B. juncea. The second population consisted of zero-erucic acid individuals (ZE) for which, an Amplified Fragment Length Polymorphism (AFLP)-based framework linkage map was constructed in the present study. By QTL mapping for oil quality fractions and oil content in the ZE population, we detected novel loci contributing to the above traits. These loci did not co-localize with mapped locations of the fatty acid desaturase 2 (FAD2), fatty acid desaturase 3 (FAD3) or fatty acid elongase (FAE) genes unlike those of the SE population wherein major QTL were found to coincide with mapped locations of the FAE genes. Some of the new loci identified in the ZE population could be detected as 'weak' contributors (with LOD < 2.5) in the SE population in which their contribution to the traits was "masked" due to pleiotropic effects of erucic acid genes. The novel loci identified in this study could now be used to improve oil quality parameters and oil content in B. juncea under zero-erucic conditions.


Asunto(s)
Ácidos Erucicos/química , Planta de la Mostaza/química , Planta de la Mostaza/genética , Aceites de Plantas/química , Sitios de Carácter Cuantitativo , Mapeo Cromosómico , Cromosomas de las Plantas , Cruzamientos Genéticos , Ligamiento Genético
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