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1.
BMC Biotechnol ; 24(1): 39, 2024 Jun 07.
Artículo en Inglés | MEDLINE | ID: mdl-38849803

RESUMEN

BACKGROUND: Melia azedarach is known as a medicinal plant that has wide biological activities such as analgesic, antibacterial, and antifungal effects and is used to treat a wide range of diseases such as diarrhea, malaria, and various skin diseases. However, optimizing the extraction of valuable secondary metabolites of M. azedarach using alternative extraction methods has not been investigated. This research aims to develop an effective, fast, and environmentally friendly extraction method using Ultrasound-assisted extraction, methanol and temperature to optimize the extraction of two secondary metabolites, lupeol and stigmasterol, from young roots of M. azedarach using the response surface methodology. METHODS: Box-behnken design was applied to optimize different factors (solvent, temperature, and ultrasonication time). The amounts of lupeol and stigmasterol in the root of M. azedarach were detected by the HPLC-DAD. The required time for the analysis of each sample by the HPLC-DAD system was considered to be 8 min. RESULTS: The results indicated that the highest amount of lupeol (7.82 mg/g DW) and stigmasterol (6.76 mg/g DW) was obtained using 50% methanol at 45 °C and ultrasonication for 30 min, and 50% methanol in 35 °C, and ultrasonication for 30 min, respectively. Using the response surface methodology, the predicted conditions for lupeol and stigmasterol from root of M. azedarach were as follows; lupeol: 100% methanol, temperature 45 °C and ultrasonication time 40 min (14.540 mg/g DW) and stigmasterol 43.75% methanol, temperature 34.4 °C and ultrasonication time 25.3 min (5.832 mg/g DW). CONCLUSIONS: The results showed that the amount of secondary metabolites lupeol and stigmasterol in the root of M. azedarach could be improved by optimizing the extraction process utilizing response surface methodology.


Asunto(s)
Melia azedarach , Triterpenos Pentacíclicos , Estigmasterol , Triterpenos Pentacíclicos/metabolismo , Estigmasterol/metabolismo , Estigmasterol/aislamiento & purificación , Estigmasterol/química , Melia azedarach/química , Cromatografía Líquida de Alta Presión , Raíces de Plantas/química , Raíces de Plantas/metabolismo , Extractos Vegetales/química , Temperatura , Solventes/química , Lupanos
2.
Comput Biol Chem ; 110: 108037, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38460436

RESUMEN

Cancer is the most prevalent disease globally, which presents a significant challenge to the healthcare industry, with breast and lung cancer being predominant malignancies. This study used RNA-seq data from the TCGA database to identify potential biomarkers for lung and breast cancer. Tumor Necrosis Factor (TNFAIP8) and Sulfite Oxidase (SUOX) showed significant expression variation and were selected for further study using structure-based drug discovery (SBDD). Compounds derived from the Euphorbia ammak plant were selected for in-silico study with both TNFAIP8 and SUOX. Stigmasterol had the greatest binding scores (normalized scores of -8.53 kcal/mol and -9.69 kcal/mol) with both proteins, indicating strong stability in their binding pockets throughout the molecular dynamics' simulation. Although Stigmasterol first changed its initial conformation (RMSD = 0.5 nm with the starting conformation) in SUOX, it eventually reached a stable conformation (RMSD of 1.5 nm). The compound on TNFAIP8 showed a persistent shape (RMSD of 0.35 nm), indicating strong protein stability. The binding free energy of the complex was calculated using the MM/GBSA technique; TNFAIP8 had a ΔGTOTAL of -24.98 kcal/mol, with TYR160 being the most significant residue, contributing -2.52 kcal/mol. On the other hand, the SUOX complex had a binding free energy of -16.87 kcal/mol, with LEU151 being the primary contributor (-1.17 kcal/mol). Analysis of the complexes' free energy landscape unveiled several states with minimum free energy, indicating robust interactions between the protein and ligand. In its conclusion, this work emphasises the favourable ability of Stigmasterol to bind with prospective targets for lung and breast cancer, indicating the need for more experimental study.


Asunto(s)
Neoplasias de la Mama , Euphorbia , Neoplasias Pulmonares , Estigmasterol , Euphorbia/química , Neoplasias de la Mama/tratamiento farmacológico , Neoplasias de la Mama/metabolismo , Humanos , Neoplasias Pulmonares/tratamiento farmacológico , Neoplasias Pulmonares/metabolismo , Estigmasterol/química , Estigmasterol/farmacología , Estigmasterol/análogos & derivados , Estigmasterol/aislamiento & purificación , Femenino , Simulación de Dinámica Molecular , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Estructura Molecular , Termodinámica , Simulación del Acoplamiento Molecular
3.
Drug Des Devel Ther ; 15: 4043-4052, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-34588765

RESUMEN

INTRODUCTION: Synergy is defined as an interaction of some substances that cooperate to give rise to the combined effect greater than the sum of their individual effects. It is a natural strategy that has evolved by nature to more efficacy with low cost. METHODS: This study is designed to evaluate the chemopreventive effect of a combined drug sample which is prepared by mixing an equal portion of stigmasterol and palmatine isolated from Azadirachta indica and Tinospora cordifolia respectively at a concentration of 100 mg/kg and 200 mg/kg body weight during the whole concentration. RESULTS: At the end of the study, it was found that this combined drug sample decreased the number of tumors and their size. This drug significantly reduced the serum level of glutamate pyruvate transaminase, alkaline phosphatase, glutamate oxalate transaminase, and bilirubin and enhanced the level of oxidative enzyme level of glutathione, superoxide dismutase, and catalase, and inhibit the level of lipid peroxides. DISCUSSION: The result suggests that combined drug samples exhibit a chemopreventive effect which is better than the effect of individual drugs (stigmasterol and palmatine).


Asunto(s)
Azadirachta/química , Alcaloides de Berberina/farmacología , Estigmasterol/farmacología , Tinospora/química , Animales , Anticarcinógenos/administración & dosificación , Anticarcinógenos/aislamiento & purificación , Anticarcinógenos/farmacología , Alcaloides de Berberina/administración & dosificación , Alcaloides de Berberina/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Combinación de Medicamentos , Sinergismo Farmacológico , Femenino , Masculino , Ratones , Estigmasterol/administración & dosificación , Estigmasterol/aislamiento & purificación
4.
Nutrients ; 13(7)2021 Jul 10.
Artículo en Inglés | MEDLINE | ID: mdl-34371875

RESUMEN

Polycyclic aromatic hydrocarbons (PAHs) have been recognized to cause neurobehavioral dysfunctions and disorder of cognition and behavioral patterns in childhood. Momordica charantia L. (MC) has been widely known for its nutraceutical and health-promoting properties. To date, the effect of MC for the prevention and handling of PAHs-induced neurotoxicity has not been reported. In the current study, the neuroprotective effects of MC and its underlying mechanisms were investigated in mouse hippocampal neuronal cell line (HT22); moreover, in silico analysis was performed with the phytochemicals MC to decipher their potential function as neuroprotectants. MC was demonstrated to possess neuroprotective effect by reducing reactive oxygen species' (ROS') production and down-regulating cyclin D1, p53, and p38 mitogen-activated protein kinase (MAPK) protein expressions, resulting in the inhibition of cell apoptosis and the normalization of cell cycle progression. Additionally, 28 phytochemicals of MC and their competence on inhibiting cytochrome P450 (CYP: CYP1A1, CYP1A2, and CYP1B1) functions were resolved. In silico analysis of vitamin E and stigmasterol revealed that their binding to either CYP1A1 or CYP1A2 was more efficient than the binding of each positive control (alizarin or purpurin). Together, MC is potentially an interesting neuroprotectant including vitamin E and stigmasterol as probable active components for the prevention for PAHs-induced neurotoxicity.


Asunto(s)
Hipocampo/efectos de los fármacos , Momordica charantia , Neuronas/efectos de los fármacos , Fármacos Neuroprotectores/farmacología , Extractos Vegetales/farmacología , Hidrocarburos Policíclicos Aromáticos/toxicidad , Estigmasterol/farmacología , Vitamina E/farmacología , Animales , Apoptosis/efectos de los fármacos , Proteínas Reguladoras de la Apoptosis/metabolismo , Ciclo Celular/efectos de los fármacos , Proteínas de Ciclo Celular/metabolismo , Línea Celular , Citocromo P-450 CYP1A1/metabolismo , Citocromo P-450 CYP1A2/metabolismo , Hipocampo/metabolismo , Hipocampo/patología , Ratones , Momordica charantia/química , Neuronas/metabolismo , Neuronas/patología , Estrés Oxidativo/efectos de los fármacos , Extractos Vegetales/aislamiento & purificación , Unión Proteica , Especies Reactivas de Oxígeno/metabolismo , Estigmasterol/aislamiento & purificación , Vitamina E/aislamiento & purificación
5.
Food Chem ; 345: 128717, 2021 May 30.
Artículo en Inglés | MEDLINE | ID: mdl-33307430

RESUMEN

Charantin, a steroidal glycoside, exists as a mixture of stigmasterol glucoside (STG) and ß-sitosterol glucoside (BSG) in the fruits of Momordica charantia. Charantin has anti-diabetic activity comparable to insulin. The present work discusses a method for separation of components of charantin namely STG and BSG by simple extraction technique followed by preparative HPLC. The identity of separated components was established by chromatographic as well as spectral techniques. Also reversed phase HPLC-DAD method was developed and validated for estimation of STG and BSG present in fruits of Momordica charantia. The method used C18 column (75 mm × 4.6 mm, 3.5 µm) as stationary phase and methanol: water (98:02, v/v) as mobile phase. Retention times of STG and BSG were found to be 10.707 min and 11.870 min, respectively. The validated method was applied to evaluate content of these components in different extracts and some commercial herbal formulations containing fruits of Momordica charantia.


Asunto(s)
Cromatografía Líquida de Alta Presión/métodos , Frutas/química , Glucósidos/análisis , Glucósidos/aislamiento & purificación , Momordica charantia/química , Sitoesteroles/análisis , Sitoesteroles/aislamiento & purificación , Estigmasterol/análogos & derivados , Estigmasterol/análisis , Estigmasterol/aislamiento & purificación
6.
Mar Drugs ; 18(12)2020 Dec 09.
Artículo en Inglés | MEDLINE | ID: mdl-33317054

RESUMEN

Fucosterol is a phytosterol that is abundant in marine brown algae and is a renowned secondary metabolite. However, its ability to protect macrophages against particulate matter (PM) has not been clarified with regard to inflammation; thus, this study aimed to illustrate the above. Padina boryana, a brown algae that is widespread in Indo-Pacific waters, was applied in the isolation of fucosterol. Isolation was conducted using silica open columns, while identification was assisted with gas chromatography-mass spectroscopy (GC-MS) and NMR. Elevated levels of PM led the research objectives toward the implementation of it as a stimulant. Both inflammation and oxidative stress were caused due the fact of its effect. RAW 264.7 macrophages were used as a model system to evaluate the process. It was apparent that the increased NO production levels, due to the PM, were mediated through the inflammatory mediators, such as inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) and pro-inflammatory cytokines (i.e., interleukin-6 (IL-6), interleukin-1 (IL-1ß) and tumor necrosis factor-α (TNF-α), including prostaglandin E2 (PGE2)). Further, investigations provided solid evidence regarding the involvement of NF-κB and mitogen-activated protein kinases (MAPKs) in the process. Oxidative stress/inflammation which are inseparable components of the cellular homeostasis were intersected through the Nrf2/HO-1 pathway. Conclusively, fucosterol is a potent protector against PM-induced inflammation in macrophages and hence be utilized as natural product secondary metabolite in a sustainable manner.


Asunto(s)
Antiinflamatorios/farmacología , Antioxidantes/farmacología , Hemo-Oxigenasa 1/metabolismo , Macrófagos/efectos de los fármacos , Proteínas de la Membrana/metabolismo , Proteínas Quinasas Activadas por Mitógenos/metabolismo , Factor 2 Relacionado con NF-E2/metabolismo , FN-kappa B/metabolismo , Phaeophyceae , Estigmasterol/análogos & derivados , Animales , Antiinflamatorios/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Citocinas/genética , Citocinas/metabolismo , Mediadores de Inflamación/metabolismo , Macrófagos/enzimología , Ratones , Estrés Oxidativo/efectos de los fármacos , Material Particulado/toxicidad , Phaeophyceae/química , Fosforilación , Células RAW 264.7 , Transducción de Señal , Estigmasterol/aislamiento & purificación , Estigmasterol/farmacología
7.
Molecules ; 25(9)2020 May 07.
Artículo en Inglés | MEDLINE | ID: mdl-32392823

RESUMEN

Brevicoryne brassicae is a problematic pest in cabbage and other field crops. Synthetic pesticides are used to control this pest, but they are injurious for human health and the environment. The present study aimed to purify and identify the active compounds from Citrullus colocynthis leaves with an appraisal of their efficacy against B. brassicae. Separation and purification were performed via different chromatographic techniques. Molecular analysis and chemical structures were recognized by mass spectrum (MS) and nuclear magnetic resonance (NMR), respectively. Moreover, in vitro and in vivo aphicidal activity was assessed using various concentrations, i.e., 6.25, 12.5, 25 and 50 µg/mL at 12, 24, 48 and 72 h exposure. The outcome shows that mass spectrum analyses of the purified compounds suggested the molecular formulae are C30H50O and C29H50O, C29H48O. The compounds were characterized as fernenol and a mixture of spinasterol, 22,23-dihydrospinasterol by 1H-NMR and 13C-NMR spectrum analysis. The toxicity results showed that the mixture of spinasterol and 22,23-dihydrospinasterol showed LC50 values of 32.36, 44.49 and 37.50 µg/mL by contact, residual and greenhouse assay at 72 h exposure, respectively. In contrast, fernenol recorded LC50 values as 47.99, 57.46 and 58.67 µg/mL, respectively. On the other hand, spinasterol, 22,23-dihydrospinasterol showed the highest mortality, i.e., 66.67%, 53.33% and 60% while, 30%, 23.33% and 25% mortality was recorded by fernenol after 72 h at 50 µg/mL by contact, residual and greenhouse assay, respectively. This study suggests that spinasterol, 22,23-dihydrospinasterol are more effective against B. brassicae which may be introduced as an effective and suitable substitute of synthetic chemical pesticides.


Asunto(s)
Áfidos/efectos de los fármacos , Citrullus colocynthis/química , Insecticidas/toxicidad , Hojas de la Planta/química , Sitoesteroles/toxicidad , Estigmasterol/análogos & derivados , Triterpenos/toxicidad , Animales , Insecticidas/análisis , Insecticidas/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/toxicidad , Sitoesteroles/análisis , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Estigmasterol/análisis , Estigmasterol/química , Estigmasterol/aislamiento & purificación , Estigmasterol/toxicidad , Triterpenos/análisis , Triterpenos/química , Triterpenos/aislamiento & purificación
8.
Molecules ; 25(10)2020 May 21.
Artículo en Inglés | MEDLINE | ID: mdl-32455580

RESUMEN

Water extract of Acacia seyal bark is used traditionally by the population in Djibouti for its anti-infectious activity. The evaluation of in vitro antibacterial, antioxidant activities and cytotoxicity as well as chemical characterization of Acacia seyal bark water and methanolic extracts were presented. The water extract has a toxicity against the MRC-5 cells at 256 µg/mL while the methanolic extract has a weak toxicity at the same concentration. The methanolic extract has a strong antioxidant activity with half maximal inhibitory concentration (IC50) of 150 ± 2.2 µg/mL using 1-diphenyl-2-picrylhydrazyl (DPPH) and IC50 of 27 ± 1.3 µg/mL using 2,2'-azino-bis 3-ethylbenzthiazoline-6-sulphonic acid (ABTS) radical methods. For ferric reducing/antioxidant power (FRAP) assay, the result is 45.74 ± 5.96 µg Vitamin C Equivalent (VCE)/g of dry weight (DW). The precipitation of tannins from methanol crude extract decreases the MIC from 64 µg/mL to 32 µg/mL against Staphylococcus aureus and Corynebacterium urealyticum. However, the antioxidant activity is higher before tannins precipitation than after (IC50 = 150 µg/mL for methanolic crude extract and 250 µg/mL after tannins precipitation determined by DPPH method). By matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analysis, the results showed that the condensed tannins consist of two types of catechin and gallocatechin-based oligomers. The fractionation led to the identification of three pure compounds: two flavanols catechin and epicatechin; one triterpene as lupeol; and a mixture of three steroids and one fatty acid: campesterol, stigmasterol, clionasterol, and oleamide.


Asunto(s)
Acacia/química , Antibacterianos/química , Antioxidantes/química , Extractos Vegetales/química , Antibacterianos/farmacología , Antioxidantes/farmacología , Benzotiazoles/química , Compuestos de Bifenilo/química , Colesterol/análogos & derivados , Colesterol/química , Colesterol/aislamiento & purificación , Corynebacterium/efectos de los fármacos , Ácidos Oléicos/química , Ácidos Oléicos/aislamiento & purificación , Fitosteroles/química , Fitosteroles/aislamiento & purificación , Picratos/química , Corteza de la Planta/química , Extractos Vegetales/farmacología , Polifenoles/química , Polifenoles/farmacología , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Espectrometría de Masa por Láser de Matriz Asistida de Ionización Desorción , Estigmasterol/química , Estigmasterol/aislamiento & purificación , Ácidos Sulfónicos/química , Taninos/química
9.
Food Chem ; 315: 126217, 2020 Jun 15.
Artículo en Inglés | MEDLINE | ID: mdl-32007812

RESUMEN

This study investigated the direct citric acid hydrolysis extraction method to optimize phytosterols extraction from hickory husk. Single factor experiments followed by a three-level three-factor Box-Behnken experiments were performed. The optimal extraction parameters were determined as: pH of 2.0, liquid-to-solid ratio of 17.12: 1 mL/g, and temperature of 55.81 °C. Practical experiments were carried out in triplicate, and subsequently yielded phytosterols of 912.452 ± 17.452 µg/g DW, in good consistence with the predicted extraction yield of 902.874 µg/g DW. The conductivity of the extract was also found to play effective role under direct citric acid hydrolysis and recorded 36.30 ± 1.08 µs/cm at optimum extraction condition. ß-Sitosterol stigmasterol, campsterol, ergosterol and lupeol were detected as main PSs and triterpenoids in hickory husk using UPLC-Triple-TOF/MS. Finally, the comparison between direct hydrolysis extraction and traditional solvent extraction showed that this new method was more effective and eco-friendlier to extract both free and conjugated phytosterols.


Asunto(s)
Carya/química , Modelos Teóricos , Fitosteroles/aislamiento & purificación , Triterpenos/aislamiento & purificación , Ácido Cítrico/química , Ergosterol/química , Ergosterol/aislamiento & purificación , Concentración de Iones de Hidrógeno , Hidrólisis , Triterpenos Pentacíclicos/química , Triterpenos Pentacíclicos/aislamiento & purificación , Fitosteroles/química , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Estigmasterol/química , Estigmasterol/aislamiento & purificación , Triterpenos/química
10.
Nat Prod Res ; 34(10): 1404-1408, 2020 May.
Artículo en Inglés | MEDLINE | ID: mdl-30417674

RESUMEN

Chemical examination of Chinese mangrove Ceriops tagal endophytic Cytospora sp., yielded a new biscyclic sesquiterpene seiricardine D (1), and eight known metabolites, xylariterpenoid A (2a), xylariterpenoid B (2b) and regiolone (3) 4-hydroxyphenethyl alcohol (4), (22E, 24R)5, 8-epidioxy-5α, 8α-ergosta-6,22E-dien-3ß-ol (5), (22E, 24R)5, 8-epidioxy-5α, 8α-ergosta-6,9(11), 22-trien-3 ß-ol (6), ß-sitosterol (7) and stigmast-4-en-3-one (8). These structures were unambiguously elucidated on the basis of extensive NMR spectroscopic and mass spectrometric analyses. The antimicrobial activities of compounds 1-8 and their effects on a panel of plant and human pathogens were evaluated.


Asunto(s)
Antiinfecciosos/aislamiento & purificación , Ascomicetos/química , Rhizophoraceae/microbiología , Sesquiterpenos/aislamiento & purificación , Antibacterianos , Antiinfecciosos/química , Antiinfecciosos/farmacología , Humanos , Estructura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacología , Sitoesteroles/aislamiento & purificación , Análisis Espectral/métodos , Estigmasterol/análogos & derivados , Estigmasterol/aislamiento & purificación
11.
Nat Prod Res ; 34(4): 474-481, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-30295511

RESUMEN

A new peroxy fatty acid, tagetnoic acid (5) [4-((3S,6S)-6-((3E,8E)-octadeca-3,8-dien-1-yl)-3,6-dihydro-1,2-dioxin-3-yl)butanoic acid] and four known metabolites: ecliptal (5-formyl-α-terthiophene) (1), 5-(4-hydroxybut-1-ynyl)-2,2'-bithiophene (2), 22,23-dihydrospinasterone (3), and stigmasterol (4) were separated from the n-hexane fraction of the aerial parts of Tagetes minuta L. (Asteraceae). Their chemical structures were verified using IR, UV, 2D and 1D NMR, and HRMS. Compounds 3-5 displayed potent lipoxygenase inhibitory potential with IC50s 2.26, 1.83, and 1.17 µM, respectively compared to indomethacin (IC50 0.89 µM). Moreover, molecular docking study revealed that the potent activity of 5 is due to H-bonding and hydrophobic interaction. The results of this study suggested that Tagetes minuta dietary consumption would be useful for the individuals at risk of acute and chronic inflammatory disorders.


Asunto(s)
Ácidos Grasos/aislamiento & purificación , Inhibidores de la Lipooxigenasa/aislamiento & purificación , Extractos Vegetales/química , Tagetes/química , Ácidos Grasos/farmacología , Humanos , Inflamación/tratamiento farmacológico , Inhibidores de la Lipooxigenasa/metabolismo , Inhibidores de la Lipooxigenasa/farmacología , Simulación del Acoplamiento Molecular , Extractos Vegetales/farmacología , Unión Proteica , Arabia Saudita , Estigmasterol/aislamiento & purificación , Tiofenos/aislamiento & purificación
12.
Mar Drugs ; 17(12)2019 Dec 09.
Artículo en Inglés | MEDLINE | ID: mdl-31818004

RESUMEN

Sargassum horneri, a sargassaceae brown alga, is one of the main species in the subtidal seaweeds flora extensively distributed in the Yellow and East China Sea. It has been proven that the phytosterols are an important class of bioactive substances in S. horneri. In this work, a counter-current chromatography approach is proposed for preparative separation of phytol and two analogue sterols from a crude extract of S. horneri. A two-phase solvent system composed of n-hexane-acetonitrile-methanol (5:5:6, v/v) was selected and optimized. The effects of rotary speed and flow rate on the retention of the stationary phase were carefully studied. Under the optimum conditions, phytol and two analogue sterols, fucosterol and saringosterol, were baseline separated, producing 19.8 mg phytol, 23.7 mg fucosterol, and 3.1 mg saringosterol from 300 mg of crude S. horneri extract in one-step separation. The purities of three target compounds were all above 85%. The structures of phytol and two sterols were identified by nuclear magnetic resonance spectroscopy.


Asunto(s)
Distribución en Contracorriente/métodos , Fitosteroles/aislamiento & purificación , Sargassum/química , Espectroscopía de Resonancia Magnética , Fitol/química , Fitol/aislamiento & purificación , Fitosteroles/química , Solventes/química , Estigmasterol/análogos & derivados , Estigmasterol/química , Estigmasterol/aislamiento & purificación
13.
Molecules ; 24(15)2019 Jul 31.
Artículo en Inglés | MEDLINE | ID: mdl-31370334

RESUMEN

Hyperpigmentation is considered by many to be a beauty problem and is responsible for photoaging. To treat this skin condition, medicinal cosmetics containing tyrosinase inhibitors are used, resulting in skin whitening. In this study, taraxerol methyl ether (1), spinasterol (2), 6-hydroxyflavanone (3), (+)-dihydrokaempferol (4), 3,4-dihydroxybenzoic acid (5), taraxerol (6), taraxerone (7), and lupeol acetate (8) were isolated from Manilkara zapota bark. Their chemical structures were elucidated by analysis of their nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS) data, and by comparing them with data found in the literature. The in vitro antityrosinase, antioxidant, and cytotoxic activities of the isolated compounds (1-8) were evaluated. (+)-Dihydrokaempferol (4) exhibited higher monophenolase inhibitory activity than both kojic acid and α-arbutin. However, it showed diphenolase inhibitory activity similar to kojic acid. (+)-Dihydrokaempferol (4) was a competitive inhibitor of both monophenolase and diphenolase activities. It exhibited the strongest 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), and ferric reducing antioxidant power (FRAP) activities of the isolated compounds. Furthermore, (+)-dihydrokaempferol (4) also demonstrated potent cytotoxicity in breast carcinoma cell line (BT474), lung bronchus carcinoma cell line (Chago-K1), liver carcinoma cell line (HepG2), gastric carcinoma cell line (KATO-III), and colon carcinoma cell line (SW620). These results suggest that M. zapota bark might be a good potential source of antioxidants and tyrosinase inhibitors for applications in cosmeceutical products.


Asunto(s)
Manilkara/química , Monofenol Monooxigenasa/antagonistas & inhibidores , Neoplasias/tratamiento farmacológico , Fitoquímicos/farmacología , Antioxidantes/química , Antioxidantes/farmacología , Arbutina/química , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Flavonoides/química , Flavonoides/aislamiento & purificación , Humanos , Hidroxibenzoatos/química , Hidroxibenzoatos/aislamiento & purificación , Monofenol Monooxigenasa/química , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/química , Ácido Oleanólico/aislamiento & purificación , Fitoquímicos/química , Pironas/química , Estigmasterol/análogos & derivados , Estigmasterol/química , Estigmasterol/aislamiento & purificación
14.
Pak J Pharm Sci ; 32(2): 661-667, 2019 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-31081780

RESUMEN

The work presented in this paper illustrates the isolation and structure elucidation of secondary metabolites of Hyoscyamus albus. Two new natural source and three known compounds were isolated from the Hyoscyamus albus. Among the isolated compounds, grivilloside H (1) and betulaplatoside (2) were isolated for the first time while scopolamine (3), ß-sitosterol (4) and stigmasterol (5) have been reported previously from the same plant. The structures of all the isolated compounds were established by using modern spectroscopic technique (UV, IR, NMR, and EI-MS) and by comparing with those available in literature.


Asunto(s)
Hyoscyamus/metabolismo , Fitoquímicos/química , Plantas Medicinales/metabolismo , Glucósidos/química , Glucósidos/aislamiento & purificación , Glucósidos/metabolismo , Hyoscyamus/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/metabolismo , Plantas Medicinales/química , Escopolamina/química , Escopolamina/aislamiento & purificación , Escopolamina/metabolismo , Metabolismo Secundario , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Sitoesteroles/metabolismo , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , Estigmasterol/química , Estigmasterol/aislamiento & purificación , Estigmasterol/metabolismo
15.
Food Chem ; 289: 313-319, 2019 Aug 15.
Artículo en Inglés | MEDLINE | ID: mdl-30955618

RESUMEN

A method was developed to simultaneously determine eight bioactive compounds in edible oil based on ultrasound-assisted saponification, liquid-liquid extraction and liquid chromatography coupled with tandem mass spectrometry. Central composite design was employed to optimize ultrasonic temperature and time of saponification. Sample treatment was conducted by ultrasound-assisted saponification at temperature of 75 °C for 40 min. Limits of detection and limits of quantification ranged from 2.0 to 3.2 and from 6.1 to 10.0 ng/mL, respectively. Linear correlations were obtained (R2 > 0.99) and the recoveries at three spiked levels were between 81.7% and 112.0%. This method was employed to determine eight compounds in camellia oils and olive oils. As results, the contents of stigmasterol, δ-tocopherol, γ-tocopherol, ß-carotene and lutein in camellia oils were significantly higher than those in olive oils (p < 0.05). The proposed method can be successfully used to determination of these eight active compounds in camellia oil and other edible oils.


Asunto(s)
Carotenoides/análisis , Fitosteroles/análisis , Aceites de Plantas/química , Espectrometría de Masas en Tándem/métodos , Tocoferoles/análisis , Camellia/química , Camellia/metabolismo , Carotenoides/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Límite de Detección , Extracción Líquido-Líquido , Fitosteroles/aislamiento & purificación , Sonicación , Estigmasterol/análisis , Estigmasterol/aislamiento & purificación , Tocoferoles/aislamiento & purificación
16.
Chem Biodivers ; 16(6): e1900092, 2019 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-31002745

RESUMEN

Investigation of yellow flower extract of Tagetes patula L. led to the identification of an aggregate of five phytoceramides. Among them, (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]icosanamide, (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]heneicosanamide, (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]docosanamide, and (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]tricosanamide were identified as new compounds and termed as tagetceramides, whereas (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]tetracosanamide was a known ceramide. A steroid (ß-sitosterol glucoside) was also isolated from the subsequent fraction. The structures of these compounds were determined on the basis of spectroscopic analyses, as well as chemical method. Several other compounds were also identified by GC/MS analysis. The fractions and some commercial products, a ceramide HFA, ß-sitosterol, and stigmasterol were evaluated against an economically important cyst nematode, Heterodera zeae. Ceramide HFA showed 100 % mortality, whereas, ß-sitosterol and stigmasterol were 40-50 % active, at 1 % concentration after 24 h of exposure time, while ß-sitosterol glucoside revealed no activity against the nematode.


Asunto(s)
Antinematodos/química , Ceramidas/química , Tagetes/química , Animales , Antinematodos/aislamiento & purificación , Antinematodos/farmacología , Ceramidas/aislamiento & purificación , Ceramidas/farmacología , Flores/química , Flores/metabolismo , Cromatografía de Gases y Espectrometría de Masas , Conformación Molecular , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Sitoesteroles/farmacología , Estigmasterol/química , Estigmasterol/aislamiento & purificación , Estigmasterol/farmacología , Tagetes/metabolismo , Tylenchoidea/efectos de los fármacos
17.
Sci Rep ; 9(1): 4908, 2019 03 20.
Artículo en Inglés | MEDLINE | ID: mdl-30894635

RESUMEN

Activation of liver X receptors (LXRs) by synthetic agonists was found to improve cognition in Alzheimer's disease (AD) mice. However, these LXR agonists induce hypertriglyceridemia and hepatic steatosis, hampering their use in the clinic. We hypothesized that phytosterols as LXR agonists enhance cognition in AD without affecting plasma and hepatic triglycerides. Phytosterols previously reported to activate LXRs were tested in a luciferase-based LXR reporter assay. Using this assay, we found that phytosterols commonly present in a Western type diet in physiological concentrations do not activate LXRs. However, a lipid extract of the 24(S)-Saringosterol-containing seaweed Sargassum fusiforme did potently activate LXRß. Dietary supplementation of crude Sargassum fusiforme or a Sargassum fusiforme-derived lipid extract to AD mice significantly improved short-term memory and reduced hippocampal Aß plaque load by 81%. Notably, none of the side effects typically induced by full synthetic LXR agonists were observed. In contrast, administration of the synthetic LXRα activator, AZ876, did not improve cognition and resulted in the accumulation of lipid droplets in the liver. Administration of Sargassum fusiforme-derived 24(S)-Saringosterol to cultured neurons reduced the secretion of Aß42. Moreover, conditioned medium from 24(S)-Saringosterol-treated astrocytes added to microglia increased phagocytosis of Aß. Our data show that Sargassum fusiforme improves cognition and alleviates AD pathology. This may be explained at least partly by 24(S)-Saringosterol-mediated LXRß activation.


Asunto(s)
Enfermedad de Alzheimer/tratamiento farmacológico , Péptidos beta-Amiloides/genética , Receptores X del Hígado/genética , Fármacos Neuroprotectores/farmacología , Fragmentos de Péptidos/genética , Placa Amiloide/tratamiento farmacológico , Sargassum/química , Estigmasterol/análogos & derivados , Enfermedad de Alzheimer/genética , Enfermedad de Alzheimer/metabolismo , Enfermedad de Alzheimer/fisiopatología , Péptidos beta-Amiloides/antagonistas & inhibidores , Péptidos beta-Amiloides/metabolismo , Compuestos de Anilina/farmacología , Animales , Astrocitos/citología , Astrocitos/efectos de los fármacos , Astrocitos/metabolismo , Cognición/efectos de los fármacos , Cognición/fisiología , Medios de Cultivo Condicionados/farmacología , Modelos Animales de Enfermedad , Regulación de la Expresión Génica , Genes Reporteros , Hipocampo/efectos de los fármacos , Hipocampo/metabolismo , Hipocampo/patología , Humanos , Receptores X del Hígado/agonistas , Receptores X del Hígado/metabolismo , Luciferasas/genética , Luciferasas/metabolismo , Masculino , Memoria a Corto Plazo/efectos de los fármacos , Memoria a Corto Plazo/fisiología , Ratones , Ratones Transgénicos , Microglía/citología , Microglía/efectos de los fármacos , Microglía/metabolismo , Fármacos Neuroprotectores/aislamiento & purificación , Fragmentos de Péptidos/antagonistas & inhibidores , Fragmentos de Péptidos/metabolismo , Placa Amiloide/genética , Placa Amiloide/metabolismo , Placa Amiloide/fisiopatología , Transducción de Señal , Estigmasterol/aislamiento & purificación , Estigmasterol/farmacología , Tiazoles/farmacología
18.
Nat Prod Res ; 33(5): 708-714, 2019 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-29183159

RESUMEN

Two new monoterpene Ducrosin A (1) and sesquiterpene Ducrosin B (2) were isolated along with three known compounds, stigmasterol (3) and two furanocoumarins (4 and 5), from the dichloromethane extract of the seeds of Ducrosia anethifolia (DC.) Boiss. Their structures were determined using extensive 1D and 2D NMR, (ES)-HRMS and IR spectroscopic analyses and by comparison with literature data. Gas chromatography analysis of the fatty acids (FAs) of D. anethifolia seed oils (DAOs) showed high percentages of elaidic acid (C18:1 Δ9t) 65% and oleic acid (C18:1 Δ9c) 15%. The total tocopherol (tocols) content in DAOs was found to be 164 mg/100 g. The cytotoxic effect of the isolates was also evaluated using the MTT assay against the HCT-116 and SKOV-3 cell lines. The results showed that compound 2 was the most cytotoxic agent followed by compounds 1 and 4, which has an epoxide moiety that most likely contributes to its activity.


Asunto(s)
Apiaceae/química , Ácidos Grasos/química , Aceites de Plantas/química , Sesquiterpenos/farmacología , Tocoferoles/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Cromatografía de Gases , Ácidos Grasos/aislamiento & purificación , Furocumarinas/aislamiento & purificación , Furocumarinas/farmacología , Humanos , Estructura Molecular , Monoterpenos/aislamiento & purificación , Monoterpenos/farmacología , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales/química , Semillas/química , Sesquiterpenos/aislamiento & purificación , Estigmasterol/aislamiento & purificación , Estigmasterol/farmacología , Tocoferoles/aislamiento & purificación , Vitamina E
19.
Nat Prod Res ; 33(2): 196-203, 2019 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-29502449

RESUMEN

Two new tetranorterpenoid derivatives named rubescins I (1) and J (2), were isolated along with six known compounds including rubescin D (3), lichexanthone (4), scopoletin (5), scopoletin O-glycoside (6), ß-sitosterol (7) and stigmasterol (8) from the stem bark of Trichilia rubescens (Meliaceae). The structures of the compounds were determined by means of MS, different NMR and by comparison with related data reported in the literature.


Asunto(s)
Limoninas/química , Meliaceae/química , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Estructura Molecular , Corteza de la Planta/química , Extractos Vegetales/química , Escopoletina/química , Escopoletina/aislamiento & purificación , Estigmasterol/química , Estigmasterol/aislamiento & purificación
20.
Nat Prod Res ; 33(10): 1495-1499, 2019 May.
Artículo en Inglés | MEDLINE | ID: mdl-29281898

RESUMEN

The aim of the study was to isolate digestive enzymes inhibitors from Mimosa pudica through a bioassay-guided fractionation approach. Repeated silica gel and sephadex LH 20 column chromatographies of bioactive fractions afforded stigmasterol, quercetin and avicularin as digestive enzymes inhibitors whose IC50 values as compared to acarbose (351.02 ± 1.46 µg mL-1) were found to be as 91.08 ± 1.54, 75.16 ± 0.92 and 481.7 ± 0.703 µg mL-1, respectively. In conclusion, M. pudica could be a good and safe source of digestive enzymes inhibitors for the management of diabetes in future.


Asunto(s)
Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/farmacología , Mimosa/química , Acarbosa/farmacología , Cromatografía Liquida/instrumentación , Cromatografía Liquida/métodos , Evaluación Preclínica de Medicamentos/métodos , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Inhibidores de Glicósido Hidrolasas/química , Hipoglucemiantes/química , Hipoglucemiantes/aislamiento & purificación , Hipoglucemiantes/farmacología , Extractos Vegetales/análisis , Extractos Vegetales/química , Quercetina/aislamiento & purificación , Quercetina/farmacología , Estigmasterol/aislamiento & purificación , Estigmasterol/farmacología , alfa-Glucosidasas/metabolismo
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