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1.
Int J Med Mushrooms ; 26(8): 75-83, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38967212

RESUMEN

Edible mushrooms, both wild and cultivated, can be seen as healthy functional food. More and more valuable compounds are obtained from mycelia of macromycetes. However, there was limited report about the medicinal fungus Laetiporus versisporus (Lloyd) Imazeki. Herein, L. versisporus was fermented on rice media and the secondary metabolites of mycelia were investigated. In this study, two-step method was used to obtain fermented products, silica gel column chromatography, recrystallization, medium pressure column chromatography, preparative thin-layer chromatography were applied to separate the chemical constituents. Nine chemical compounds (1-9) including one new triterpenoid acid versisponic acid F were identified by NMR (nuclear magnetic resonance) spectroscopy and MS (mass spectrometry). Seven compounds including monolinoleoyl glycerol, linoleic acid, ergosta-5, 7, 22-triene-3ß-ol, ß-sitosterol, daucosterol, versisponic acid F were isolated for the first time from L. versisporus.


Asunto(s)
Fermentación , Micelio , Micelio/química , Espectroscopía de Resonancia Magnética , Triterpenos/química , Cromatografía en Capa Delgada , Espectrometría de Masas , Ácido Linoleico/metabolismo , Estructura Molecular , Agaricales/química , Agaricales/metabolismo , Oryza/química , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación
2.
Comb Chem High Throughput Screen ; 27(11): 1676-1699, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38305397

RESUMEN

AIM: To evaluate the antidiabetic potential of ß-sitosterol from Zingiber roseum. BACKGROUND: Diabetes mellitus is a cluster of metabolic disorders, and 90% of diabetic patients are affected with Type II diabetes (DM2). For the treatment of DM2, thiazolidinedione drugs (TZDs) were proposed, but recent studies have shown that TZDs have several detrimental effects, such as weight gain, kidney enlargement (hypertrophy), fluid retention, increased risk of bone fractures, and potential harm to the liver (hepatotoxicity). That is why a new molecule is needed to treat DM2. OBJECTIVE: The current research aimed to assess the efficacy of ß-Sitosterol from methanolic extract of Zingiber roseum in managing diabetes via PPARγ modulation. METHODS: Zingiber roseum was extracted using methanol, and GC-MS was employed to analyze the extract. Through homology modeling, PPARγ structure was predicted. Molecular docking, MD simulation, free binding energies, QSAR, ADMET, and bioactivity and toxicity scores were all used during the in-depth computer-based research. RESULTS: Clinically, agonists of synthetic thiazolidinedione (TZDs) have been used therapeutically to treat DM2, but these TZDs are associated with significant risks. Hence, GC-MS identified phytochemicals to search for a new PPAR-γ agonist. Based on the in-silico investigation, ß-sitosterol was found to have a higher binding affinity (-8.9 kcal/mol) than standard drugs. MD simulations and MMGBSA analysis also demonstrated that ß-sitosterol bound to the PPAR-γ active site stably. CONCLUSION: It can be concluded that ß-sitosterol from Z. roseum attenuates Type-II diabetes by modulating PPARγ activity.


Asunto(s)
Hipoglucemiantes , Simulación del Acoplamiento Molecular , PPAR gamma , Sitoesteroles , PPAR gamma/metabolismo , Sitoesteroles/farmacología , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Humanos , Diabetes Mellitus Tipo 2/tratamiento farmacológico , Diabetes Mellitus Tipo 2/metabolismo , Extractos Vegetales/química , Extractos Vegetales/farmacología
3.
Molecules ; 26(23)2021 Nov 27.
Artículo en Inglés | MEDLINE | ID: mdl-34885777

RESUMEN

Phytochemical investigation of chloroform fraction (DBC) and ethyl acetate fraction (DBE) of D. bupleuroides (Acanthaceae) resulted in the isolation of ß-sitosterol (1) from DBC and vanillic acid (2) from DBE, which were first to be isolated from D. bupleuroides. ß-Sitosterol (1) exhibited substantial antioxidant activity (IC50 = 198.87 µg/mL), whereas vanillic acid (2) showed significant antioxidant power (IC50 = 92.68 µg/mL) employing 1,1-diphenyl-2-picrylhydrazyl (DPPH*) radical scavenging capacity assay. Both compounds showed pronounced antimicrobial activity using the agar disc diffusion method, particularly against fungi showing MIC values of 0.182 and 0.02 concerning Candida albicans, respectively, and 0.001 mg/mL regarding Penicillium notatum. They revealed considerable antibacterial activity with MIC values ranging between 0.467 and 0.809 mg/mL. Vanillic acid (2) exhibited substantial anticancer potential displaying 48.67% cell viability at a concentration of 100 µg/mL using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-Diphenyl-2H-Tetrazolium Bromide) assay concerning HepG2 cell lines. These results were further consolidated by in silico studies on different enzymes, where vanillic acid displayed a high fitting score in the active pockets of DNA-gyrase, dihydrofolate reductase, aminoglycoside nucleotidyltransferase, and ß-lactamase. It also inhibited human cyclin-dependent kinase 2 (CDK-2) and DNA topoisomerase II, as revealed by the in silico studies. ADME/TOPKAT (absorption, distribution, metabolism, excretion, and toxicity) prediction showed that vanillic acid exhibited reasonable pharmacodynamic, pharmacokinetic, and toxicity properties and, thus, could perfectly together with D. bupleuroides crude extract be incorporated in pharmaceutical preparations to counteract cancer and microbial invasion, as well as oxidative stress. Thus, it is concluded that D. bupleroides could be a potential source of therapeutically active compounds, which would be helpful for the discovery of clinically effective and safe drugs.


Asunto(s)
Acanthaceae/química , Antiinfecciosos/farmacología , Antineoplásicos/farmacología , Antioxidantes/farmacología , Simulación por Computador , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Bacterias/efectos de los fármacos , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Hongos/efectos de los fármacos , Humanos , Pruebas de Sensibilidad Microbiana , Sitoesteroles/aislamiento & purificación , Sitoesteroles/farmacología , Termodinámica , Ácido Vanílico/aislamiento & purificación , Ácido Vanílico/farmacología
4.
J Sep Sci ; 44(21): 3924-3932, 2021 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-34459118

RESUMEN

ß-Sitosterol is a major bioactive constituent in plants with potent anticancer effects against many human cancer cells, but its bioavailability and therapeutic efficacy are limited by its poor solubility in water. In this study, C6 -imidazole chitosan, C6 -1-methylimidazole chitosan, C6 -1-ethylimidazole chitosan, C6 -1-vinylimidazole chitosan, C6 -1-allylimidazole chitosan, and C6 -1-butylimidazole chitosan were prepared to extract ß-sitosterol from edible oil samples via ultrasonic-assisted solid liquid extraction. The structures and properties of the newly synthesized products were characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, and elemental analysis. The extraction abilities of the derivatives were tested in the experiment with high-performance liquid chromatography (limit of detection 0.21 µg/g and limit of quantification 0.67 µg/g), and the % relative standard deviation (<3.25%) and recovery values of the prepared chitosan derivatives toward ß-sitosterol (average: 100.20%) were acceptable. The spiked interday and intraday recoveries of ß-sitosterol were 102.60 ± 2.78 and 103.90 ± 3.04%, respectively. The actual amounts of ß-sitosterol extracted from three real samples using C6 -imidazole chitosan according to the solid phase extraction method were 3302.40, 901.70, and 2045.60 mg/kg for corn oil, olive oil, and pea oil, respectively.


Asunto(s)
Quitosano/química , Imidazoles/química , Aceites de Plantas/química , Sitoesteroles/aislamiento & purificación , Extracción en Fase Sólida/métodos , Cromatografía Líquida de Alta Presión , Límite de Detección , Modelos Lineales , Microondas , Reproducibilidad de los Resultados , Sitoesteroles/análisis , Sitoesteroles/química
5.
Bioorg Med Chem Lett ; 48: 128248, 2021 09 15.
Artículo en Inglés | MEDLINE | ID: mdl-34252548

RESUMEN

The observation of a dog eating the roots of Odontonema strictum in 2008 in Lubumbashi (DR. Congo) was the starting point of this research which later led to the isolation of ß-sitosterol (BSL), a known phytosterol, isolated for the first time from the leaves of this tropical plant which has a large range of medicinal properties including anti-inflammation, anti-hypertension and antibacterial. The analysis of the 1H NMR spectrum showed that the active compound contains 60% of BSL and 40% of stigmasterol. With a melting point (m.p.) of 134-136 °C and the Rf value 0.55 in EtOAc-hexane (1:3) on silica gel TLC, the active compound was confirmed to be BSL. Here, we determined the minimal inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) of BSL on Staphylococcus aureus by the broth dilution method. The MIC and MBC were found to be 1.24 mg/mL and 2.208 mg/mL, respectively. For the crude extract, the MIC and MBC were 4.33 mg/mL and the MBC was 7.66 mg/mL, respectively. The Total antibacterial activity underlined the fact that the crude extract from 1 g of plant materials could be diluted 65 times and still retains the ability to inhibit the growth of S. aureus. This is the first report of the antibacterial activity of BSL from this plant.


Asunto(s)
Acanthaceae/química , Antibacterianos/farmacología , Sitoesteroles/farmacología , Staphylococcus aureus/efectos de los fármacos , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Hojas de la Planta/química , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Relación Estructura-Actividad
6.
J Oleo Sci ; 70(1): 51-58, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-33431772

RESUMEN

In this study, important physicochemical properties, fatty acid and sterol compositions of olive oils from the olives which harvested from Mersin (Buyuk Topak Ulak, Gemlik, Sari Ulak), Adana (Gemlik), Osmaniye (Gemlik) and Hatay (Gemlik, Kargaburun, Hasebi, Halhali) in the Eastern Mediterranean region of Turkey have been investigated. Ripening index and oil yield analysis of the olives and free fatty acids, peroxide value, UV absorbance (K232, K270), fatty acid composition, sterol composition, erythrodiol+uvaol content, and total sterol analysis of the olive oil samples were carried out. The levels of free acidity in the olive oil samples ranged from 0.39% (Hatay Gemlik: HG3) to 2.23% (Mersin Gemlik: MG). Peroxide value ranged from 8.87 to 18.87 meq O2/kg. As K232 values in the oils fluctuated between 1.4370 and 2.3970, K270 values varied between 0.1270 and 0.1990. The results showed that all ΔK values were lower than the maximum legal limit of 0.01. The main fatty acid in all oil samples was oleic acid, ranging from 58.72% (Hatay Hasebi: HHs) to 74.54% (Hatay Gemlik: HG2). Palmitic acid values were within the percentage of 12.83% (Hatay Kargaburun: HK) to 18.50% (HHs). Total sterol content varied from 720.41 mg/kg (Hatay Kargaburun: HK) to 4519.17 mg/kg (Buyuk Topak Ulak: BTU). The ß-sitosterol percentage of olive oils ranged from 76.12% (Adana Gemlik: AG) to 94.23% (Buyuk Topak Ulak: BTU). The results of this study indicated that variety significantly affect the quality indices, fatty acid and sterol compositions of olive oils significantly varied among varieties.


Asunto(s)
Ácidos Grasos/análisis , Análisis de los Alimentos , Calidad de los Alimentos , Aceite de Oliva/análisis , Aceite de Oliva/química , Esteroles/análisis , Fenómenos Químicos , Región Mediterránea , Ácido Oléico/análisis , Ácido Oléico/aislamiento & purificación , Aceite de Oliva/clasificación , Ácido Palmítico/análisis , Ácido Palmítico/aislamiento & purificación , Sitoesteroles/análisis , Sitoesteroles/aislamiento & purificación , Turquía
7.
Nat Prod Res ; 35(8): 1357-1363, 2021 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-31397595

RESUMEN

A new steroidal ester bearing n-nonadecanoyl moiety (1) and a mixture of isomeric cerebrosides (2) along with two known compounds were isolated from the methanol extract of the stem-bark of Anacardium occidentale. The structure of the new steroidal ester was determined as 3-n-nonadecanoyl-ß-sitosterol on the basis of modern spectroscopic techniques (IR, ESI-MS, HR-ESIMS, 1D and 2D NMR) and chemical degradation studies. The structures of the known compounds were identified as gallic acid and tanacetene by comparison of the spectroscopic data with those of reported data. The mixture of cerebrosides was confirmed based on the analysis of 1D and 2D NMR. These compounds were evaluated for cytotoxicity against human cancer cell lines A549, SCOV3 and rat normal cell line NRK49f.


Asunto(s)
Anacardium/química , Corteza de la Planta/química , Tallos de la Planta/química , Sitoesteroles/aislamiento & purificación , Animales , Espectroscopía de Resonancia Magnética con Carbono-13 , Línea Celular Tumoral , Humanos , Concentración 50 Inhibidora , Extractos Vegetales/química , Espectroscopía de Protones por Resonancia Magnética , Ratas , Sitoesteroles/farmacología
8.
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
9.
Sci Rep ; 10(1): 20440, 2020 11 24.
Artículo en Inglés | MEDLINE | ID: mdl-33235245

RESUMEN

Leishmaniasis, a major neglected tropical disease, affects millions of individuals worldwide. Among the various clinical forms, visceral leishmaniasis (VL) is the deadliest. Current antileishmanial drugs exhibit toxicity- and resistance-related issues. Therefore, advanced chemotherapeutic alternatives are in demand, and currently, plant sources are considered preferable choices. Our previous report has shown that the chloroform extract of Corchorus capsularis L. leaves exhibits a significant effect against Leishmania donovani promastigotes. In the current study, bioassay-guided fractionation results for Corchorus capsularis L. leaf-derived ß-sitosterol (ß-sitosterolCCL) were observed by spectroscopic analysis (FTIR, 1H NMR, 13C NMR and GC-MS). The inhibitory efficacy of this ß-sitosterolCCL against L. donovani promastigotes was measured (IC50 = 17.7 ± 0.43 µg/ml). ß-SitosterolCCL significantly disrupts the redox balance via intracellular ROS production, which triggers various apoptotic events, such as structural alteration, increased storage of lipid bodies, mitochondrial membrane depolarization, externalization of phosphatidylserine and non-protein thiol depletion, in promastigotes. Additionally, the antileishmanial activity of ß-sitosterolCCL was validated by enzyme inhibition and an in silico study in which ß-sitosterolCCL was found to inhibit Leishmania donovani trypanothione reductase (LdTryR). Overall, ß-sitosterolCCL appears to be a novel inhibitor of LdTryR and might represent a successful approach for treatment of VL in the future.


Asunto(s)
Antiprotozoarios/farmacología , Corchorus/química , Leishmania donovani/enzimología , NADH NADPH Oxidorreductasas/metabolismo , Sitoesteroles/farmacología , Antiprotozoarios/química , Antiprotozoarios/aislamiento & purificación , Sitios de Unión/efectos de los fármacos , Fraccionamiento Químico , Leishmania donovani/efectos de los fármacos , Membranas Mitocondriales , Modelos Moleculares , Simulación del Acoplamiento Molecular , NADH NADPH Oxidorreductasas/química , Extractos Vegetales/química , Hojas de la Planta/química , Conformación Proteica , Proteínas Protozoarias/antagonistas & inhibidores , Especies Reactivas de Oxígeno/metabolismo , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación
10.
Molecules ; 25(13)2020 Jul 02.
Artículo en Inglés | MEDLINE | ID: mdl-32630623

RESUMEN

Indigofera zollingeriana Miq (I. zollingeriana) is a widely grown tree in Vietnam. It is used to cure various illnesses. The purpose of this study was to investigate the chemical constituents of an I. zollingeriana extract and test its anticancer activity on hepatocellular cells (Huh7 and HepG2). The experimental results of the analysis of the bioactive compounds revealed that ß-sitosterol (ß-S) and ß-sitosterol-glucoside (ß-SG) were the main ingredients of the I. zollingeriana extract. Regarding anticancer activity, the ß-S and ß-SG of I. zollingeriana were found to exhibit cytotoxic effects against HepG2 and Huh7 cells, but not against normal human primary fibroblasts. The ß-S was able to inhibit the proliferation of HepG2 and Huh7 cells in a dose-dependent manner with half-maximal inhibitory concentration (IC50) values of 6.85 ± 0.61 µg/mL and 8.71 ± 0.21 µg/mL, respectively (p < 0.01), whereas the ß-SG IC50 values were 4.64 ± 0.48 µg/mL for HepG2 and 5.25 ± 0.14 µg/mL for Huh7 cells (p < 0.01). Remarkably, our study also indicated that ß-S and ß-SG exhibited cytotoxic activities via inducing apoptosis and activating caspase-3 and -9 in these cells. These findings demonstrated that ß-S and ß-SG from I. zollingeriana could potentially be developed into promising therapeutic agents to treat liver cancer.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Indigofera/química , Neoplasias Hepáticas/tratamiento farmacológico , Sitoesteroles/farmacología , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Apoptosis/efectos de los fármacos , Caspasa 3/metabolismo , Caspasa 9/metabolismo , Proliferación Celular/efectos de los fármacos , Fragmentación del ADN/efectos de los fármacos , Fibroblastos/efectos de los fármacos , Células Hep G2 , Humanos , Neoplasias Hepáticas/patología , Espectroscopía de Resonancia Magnética , Plantas Medicinales/química , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Vietnam
11.
Environ Toxicol ; 35(10): 1125-1136, 2020 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-32449848

RESUMEN

This study aimed to evaluate the in vivo anticancer effects of daucosterol which was earlier reported to possess in vitro anticancer effects. Breast tumor was induced in 30 rats using the environmental carcinogen 7,12-dimethylbenz(a)anthracene (DMBA) while 6 control rats received olive oil (NOR). Animals with palpable tumors were randomized into five groups (n = 6) each as follows: negative control group treated with the vehicle (DMBA); positive control group treated with 5 mg/kg BW doxorubicin (DOXO + DMBA); three groups treated with daucosterol at doses of 2.5, 5, and 10 mg/kg BW (DAU + DMBA). Treatment lasted 28 days afterward, tumor (mass, volume, cancer antigen [CA] 15-3 level and histoarchitecture), hematological and toxicological parameters were examined. The tumor volume gradually increased in the DMBA group during the 28 days, with a tumor volume gain of ∼390 cm3 . Daucosterol at all doses reduced tumor volume (∼133.7 cm3 at 10 mg/kg) as well as protein, malondialdehyde (MDA), and CA 15-3 levels compared to DMBA rats. Tumor sections in daucosterol-treated rats showed a lower proliferation of mammary ducts with mild (5 and 10 mg/kg) to moderate (2.5 mg/kg) inflammatory responses. Moreover, it exhibited an antioxidant effect, evidenced by a significant and dose-dependent decreased in MDA levels, as well as an increase in catalase activity compared to the DMBA group. Daucosterol showed for the first time in vivo antitumor effects that corroborate its previous in vitro effects.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Capparaceae/química , Neoplasias Mamarias Experimentales/tratamiento farmacológico , Sitoesteroles/farmacología , 9,10-Dimetil-1,2-benzantraceno/toxicidad , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/uso terapéutico , Antioxidantes/metabolismo , Carcinógenos/toxicidad , Relación Dosis-Respuesta a Droga , Femenino , Neoplasias Mamarias Experimentales/inducido químicamente , Neoplasias Mamarias Experimentales/metabolismo , Neoplasias Mamarias Experimentales/patología , Estructura Molecular , Corteza de la Planta/química , Ratas , Ratas Wistar , Sitoesteroles/aislamiento & purificación , Sitoesteroles/uso terapéutico
12.
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
13.
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
14.
J Leukoc Biol ; 108(2): 509-517, 2020 08.
Artículo en Inglés | MEDLINE | ID: mdl-32392637

RESUMEN

Rheumatoid arthritis (RA) is a chronic disease with complex molecular network of pathophysiology, single drug is usually not full satisfactory because it is almost impossible to target the whole molecular network of the disease. Drug combinations that act synergistically with each another is an effective strategy in RA therapy. In this study, we aimed to establish a new strategy to search effective synergized compounds from Chinese herbal medicine (CHM) used in RA. Based on multi-information integrative approaches, imperatorin (IMP) and ß-sitosterol (STO) were predicted as the most effective pair for RA therapy. Further animal experiments demonstrated that IMP+STO treatment ameliorated arthritis severity of collagen-induced arthritis (CIA) rats in a synergistic manner, whereas IMP or STO administration separately had no such effect. RNA sequencing and IPA analysis revealed that the synergistic mechanism of IMP+STO treatment was related to its regulatory effect on 5 canonical signaling pathways, which were not found when IMP or STO used alone. Moreover, LTA, CD83, and SREBF1 were 3 important targets for synergistic mechanism of IMP+STO treatment. The levels of these 3 genes were significantly up-regulated in IMP+STO group compared to model group, whereas IMP or STO administration separately had no effect on them. In conclusion, this study found that IMP and STO were 2 synergistic compounds from the CHM in RA therapy, whose synergistic mechanism was closely related to regulate the levels of LTA, CD83, and SREBF1.


Asunto(s)
Artritis Experimental/tratamiento farmacológico , Furocumarinas/farmacología , Sitoesteroles/farmacología , Animales , Artritis Experimental/etiología , Artritis Experimental/metabolismo , Artritis Experimental/patología , Artritis Reumatoide/tratamiento farmacológico , Artritis Reumatoide/etiología , Artritis Reumatoide/metabolismo , Linfocitos T CD4-Positivos/inmunología , Linfocitos T CD4-Positivos/metabolismo , Biología Computacional/métodos , Modelos Animales de Enfermedad , Sinergismo Farmacológico , Medicamentos Herbarios Chinos , Furocumarinas/aislamiento & purificación , Furocumarinas/uso terapéutico , Masculino , Fitoterapia , Ratas , Índice de Severidad de la Enfermedad , Transducción de Señal , Sitoesteroles/aislamiento & purificación , Sitoesteroles/uso terapéutico
15.
Molecules ; 25(7)2020 Mar 29.
Artículo en Inglés | MEDLINE | ID: mdl-32235298

RESUMEN

Girardinia diversifolia, also known as Himalayan nettle, is a perennial herb used in Nepal to make fiber as well as in traditional medicine for the treatment of several diseases. To date, phytochemical studies and biological assays on this plant are scarce. Thus, in the present work, the G. diversifolia extracts have been evaluated for their potential pharmaceutical, cosmetic and nutraceutical uses. For this purpose, detailed phytochemical analyses were performed, evidencing the presence of phytosterols, fatty acids, carotenoids, polyphenols and saponins. The most abundant secondary metabolites were ß- and γ-sitosterol (11 and 9% dw, respectively), and trans syringin (0.5 mg/g) was the most abundant phenolic. Fatty acids with an abundant portion of unsaturated derivatives (linoleic and linolenic acid at 22.0 and 9.7 mg/g respectively), vitamin C (2.9 mg/g) and vitamin B2 (0.12 mg/g) were also present. The antioxidant activity was moderate while a significant ability to inhibit acetylcholinesterase (AChE), butyrilcholinesterase (BuChE), tyrosinase, α-amylase and α-glucosidase was observed. A cytotoxic effect was observed on human ovarian, pancreatic and hepatic cancer cell lines. The effect in hepatocarcinoma cells was associated to a downregulation of the low-density lipoprotein receptor (LDLR), a pivotal regulator of cellular cholesterol homeostasis. These data show the potential usefulness of this species for possible applications in pharmaceuticals, nutraceuticals and cosmetics.


Asunto(s)
Anticolesterolemiantes/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Citotoxinas/aislamiento & purificación , Inhibidores Enzimáticos/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Urticaceae/química , Anticolesterolemiantes/farmacología , Antioxidantes/farmacología , Ácido Ascórbico/aislamiento & purificación , Ácido Ascórbico/farmacología , Carotenoides/aislamiento & purificación , Carotenoides/farmacología , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Citotoxinas/farmacología , Inhibidores Enzimáticos/farmacología , Ácidos Grasos/aislamiento & purificación , Ácidos Grasos/farmacología , Glucósidos/aislamiento & purificación , Glucósidos/farmacología , Humanos , Fenilpropionatos/aislamiento & purificación , Fenilpropionatos/farmacología , Fitoquímicos/farmacología , Fitosteroles/aislamiento & purificación , Fitosteroles/farmacología , Extractos Vegetales/química , Polifenoles/aislamiento & purificación , Polifenoles/farmacología , Receptores de LDL/antagonistas & inhibidores , Receptores de LDL/genética , Receptores de LDL/metabolismo , Riboflavina/aislamiento & purificación , Riboflavina/farmacología , Saponinas/aislamiento & purificación , Saponinas/farmacología , Sitoesteroles/aislamiento & purificación , Sitoesteroles/farmacología
16.
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
17.
Biomolecules ; 10(1)2020 01 02.
Artículo en Inglés | MEDLINE | ID: mdl-31906487

RESUMEN

The phytochemical investigation of Fraxinus hupehensis led to the isolation and characterization of ten compounds which were identified as fraxin (1), fraxetin (2), esculetin (3), cichoriin (4), euphorbetin (5), kaempferol-3-O-ß-rutinoside (6), oleuropein (7), linoleic acid (8), methyl linoleate (9), and ß-sitosterol (10). Structures of the isolated constituents were characterized by 1H NMR, 13C NMR and HRMS. All the compounds, except compounds 3 and 4, were isolated for the first time from this plant. Further, this was the first report for the occurrence of compound 5 in the Fraxinus species. Antifungal activity evaluation showed that compound 2 exhibited significant inhibitory effects against Bipolaris maydis, Sclerotium rolfsii, and Alternaria solani with EC50 values of 0.31 ± 0.01 mmol/L, 10.50 ± 0.02 mmol/L, and 0.40 ± 0.02 mmol/L respectively, compared to the positive control, Carbendazim, with its EC50 values of 0.74 ± 0.01 mmol/L, 1.78 ± 0.01 mmol/L and 1.41 ± 0.00 mmol/L. Herbicidal activity tests showed that compounds 8-10 had strong inhibitory effects against the roots of Echinochloa crus-galli with EC50 values of 1.16 ± 0.23 mmol/L, 1.28 ± 0.58 mmol/L and 1.33 ± 0.35 mmol/L respectively, more potently active than that of the positive control, Cyanazine, with its EC50 values of 1.56 ± 0.44 mmol/L. However, none of the compounds proved to be active against the tested bacteria (Erwinia carotovora, Pseudomonas syringae, and Ralstonia solanacearum).


Asunto(s)
Fraxinus/química , Fraxinus/metabolismo , Extractos Vegetales/aislamiento & purificación , Antifúngicos/farmacología , Benzopiranos/aislamiento & purificación , Cumarinas/aislamiento & purificación , Glucósidos/aislamiento & purificación , Herbicidas/química , Glucósidos Iridoides , Iridoides/aislamiento & purificación , Quempferoles/aislamiento & purificación , Ácido Linoleico/aislamiento & purificación , Ácidos Linoleicos/aislamiento & purificación , Extractos Vegetales/metabolismo , Raíces de Plantas , Sitoesteroles/aislamiento & purificación , Umbeliferonas/aislamiento & purificación
18.
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
19.
Nat Prod Res ; 34(16): 2315-2318, 2020 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-30587037

RESUMEN

The present work deals with the biological and phytochemical studies on Capparis decidua (Forssk) Edgew from Cholistan desert of Pakistan. Aerial and floral parts of C. decidua were collected and dried under shade. Powdered materials of each part of C. decidua were extracted with methanol separately, followed by phytochemical studies. Hexane fraction of aerial parts of the C. decidua obtained after solvent-solvent extraction was purified through repeated column chromatography by increasing order of polarity. Four compounds were purified and identified as simiarenol (1), lupeol (2), taraxerol (3) and ß-sitosterol (4). Simiarenol and lupeol were isolated for the first time from genus Capparis. The structures of these compounds were established by comparing the spectroscopic data (1H NMR, 13C NMR, IR, UV & Mass spectrometry) reported in literature. The structure of 1 was further confirmed by XRD analysis. Anti-bacterial activities of crude methanolic extracts were determined against 13 bacterial strains (MIC 250-1000 µg/mL). α-Glucosidase and urease inhibitory activities of pure compounds were also determined. Compounds 1, 2 and 4 showed α-glucosidase inhibition with IC50 at 96.12 ± 0.12, 65.28 ± 0.13 and 128.14 ± 0.17 µM, respectively.


Asunto(s)
Capparis/química , Fitoquímicos/aislamiento & purificación , Extractos Vegetales/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Clima Desértico , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/farmacología , Estructura Molecular , Pakistán , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación
20.
Food Chem ; 311: 125890, 2020 May 01.
Artículo en Inglés | MEDLINE | ID: mdl-31757493

RESUMEN

The recovery of α-tocopherol and ß-sitosterol from the deodorizer distillate of sunflower oil using solid phase extraction is reported. Performance of the silicon-rich and inexpensive zeolite, ZSM-5, and its modified versions were compared as adsorbents. Modifications of the zeolite frame were performed under both acidic and basic conditions to desilicate and dealuminate the parent ZSM-5. Base treatment resulted in hierarchical porosity and increased mesoporosity in the structure, which made the desilicated material as the best adsorbent of the study. Optimization of the solid phase extraction conditions was also studied and high recoveries of α-tocopherol and ß-sitosterol, up to 99.20% and 97.32%, respectively, were achieved. The preparation and characterisation of the reported sorbents, as high-performance adsorbents, were not only proved to be economically promising, due to recycling of nutritious products, but also improves the ecological credentials of the process through reduction in waste.


Asunto(s)
Sitoesteroles/aislamiento & purificación , Aceite de Girasol/química , Zeolitas/química , alfa-Tocoferol/aislamiento & purificación , Adsorción , Cromatografía Líquida de Alta Presión , Porosidad , Sitoesteroles/análisis , Extracción en Fase Sólida , alfa-Tocoferol/análisis
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