RESUMO
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.
Assuntos
Acanthaceae/química , Anti-Infecciosos/farmacologia , Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Simulação por Computador , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Bactérias/efeitos dos fármacos , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Fungos/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologia , Termodinâmica , Ácido Vanílico/isolamento & purificação , Ácido Vanílico/farmacologiaRESUMO
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.
Assuntos
Quitosana/química , Imidazóis/química , Óleos de Plantas/química , Sitosteroides/isolamento & purificação , Extração em Fase Sólida/métodos , Cromatografia Líquida de Alta Pressão , Limite de Detecção , Modelos Lineares , Micro-Ondas , Reprodutibilidade dos Testes , Sitosteroides/análise , Sitosteroides/químicaRESUMO
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.
Assuntos
Anacardium/química , Casca de Planta/química , Caules de Planta/química , Sitosteroides/isolamento & purificação , Animais , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Linhagem Celular Tumoral , Humanos , Concentração Inibidora 50 , Extratos Vegetais/química , Espectroscopia de Prótons por Ressonância Magnética , Ratos , Sitosteroides/farmacologiaRESUMO
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.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Indigofera/química , Neoplasias Hepáticas/tratamento farmacológico , Sitosteroides/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Apoptose/efeitos dos fármacos , Caspase 3/metabolismo , Caspase 9/metabolismo , Proliferação de Células/efeitos dos fármacos , Fragmentação do DNA/efeitos dos fármacos , Fibroblastos/efeitos dos fármacos , Células Hep G2 , Humanos , Neoplasias Hepáticas/patologia , Espectroscopia de Ressonância Magnética , Plantas Medicinais/química , Sitosteroides/química , Sitosteroides/isolamento & purificação , VietnãRESUMO
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 â¼390 cm3 . Daucosterol at all doses reduced tumor volume (â¼133.7 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.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Capparaceae/química , Neoplasias Mamárias Experimentais/tratamento farmacológico , Sitosteroides/farmacologia , 9,10-Dimetil-1,2-benzantraceno/toxicidade , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/uso terapêutico , Antioxidantes/metabolismo , Carcinógenos/toxicidade , Relação Dose-Resposta a Droga , Feminino , Neoplasias Mamárias Experimentais/induzido quimicamente , Neoplasias Mamárias Experimentais/metabolismo , Neoplasias Mamárias Experimentais/patologia , Estrutura Molecular , Casca de Planta/química , Ratos , Ratos Wistar , Sitosteroides/isolamento & purificação , Sitosteroides/uso terapêuticoRESUMO
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.
Assuntos
Acacia/química , Antibacterianos/química , Antioxidantes/química , Extratos Vegetais/química , Antibacterianos/farmacologia , Antioxidantes/farmacologia , Benzotiazóis/química , Compostos de Bifenilo/química , Colesterol/análogos & derivados , Colesterol/química , Colesterol/isolamento & purificação , Corynebacterium/efeitos dos fármacos , Ácidos Oleicos/química , Ácidos Oleicos/isolamento & purificação , Fitosteróis/química , Fitosteróis/isolamento & purificação , Picratos/química , Casca de Planta/química , Extratos Vegetais/farmacologia , Polifenóis/química , Polifenóis/farmacologia , Sitosteroides/química , Sitosteroides/isolamento & purificação , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz , Estigmasterol/química , Estigmasterol/isolamento & purificação , Ácidos Sulfônicos/química , Taninos/químicaRESUMO
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.
Assuntos
Anticolesterolemiantes/isolamento & purificação , Antioxidantes/isolamento & purificação , Citotoxinas/isolamento & purificação , Inibidores Enzimáticos/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Urticaceae/química , Anticolesterolemiantes/farmacologia , Antioxidantes/farmacologia , Ácido Ascórbico/isolamento & purificação , Ácido Ascórbico/farmacologia , Carotenoides/isolamento & purificação , Carotenoides/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Citotoxinas/farmacologia , Inibidores Enzimáticos/farmacologia , Ácidos Graxos/isolamento & purificação , Ácidos Graxos/farmacologia , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Humanos , Fenilpropionatos/isolamento & purificação , Fenilpropionatos/farmacologia , Compostos Fitoquímicos/farmacologia , Fitosteróis/isolamento & purificação , Fitosteróis/farmacologia , Extratos Vegetais/química , Polifenóis/isolamento & purificação , Polifenóis/farmacologia , Receptores de LDL/antagonistas & inibidores , Receptores de LDL/genética , Receptores de LDL/metabolismo , Riboflavina/isolamento & purificação , Riboflavina/farmacologia , Saponinas/isolamento & purificação , Saponinas/farmacologia , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologiaRESUMO
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.
Assuntos
Carya/química , Modelos Teóricos , Fitosteróis/isolamento & purificação , Triterpenos/isolamento & purificação , Ácido Cítrico/química , Ergosterol/química , Ergosterol/isolamento & purificação , Concentração de Íons de Hidrogênio , Hidrólise , Triterpenos Pentacíclicos/química , Triterpenos Pentacíclicos/isolamento & purificação , Fitosteróis/química , Sitosteroides/química , Sitosteroides/isolamento & purificação , Estigmasterol/química , Estigmasterol/isolamento & purificação , Triterpenos/químicaRESUMO
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.
Assuntos
Sitosteroides/isolamento & purificação , Óleo de Girassol/química , Zeolitas/química , alfa-Tocoferol/isolamento & purificação , Adsorção , Cromatografia Líquida de Alta Pressão , Porosidade , Sitosteroides/análise , Extração em Fase Sólida , alfa-Tocoferol/análiseRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Crateva adansonii DC (Capparaceae) is a shrub used to treat tumors in Cameroon. In our previous reports, a Crateva adansonii dichloromethane-methanol (DCM/MeOH) extract was shown to prevent chemically induced tumors in Wistar rats. AIM OF STUDY: To determine the bioactive principle of Crateva adansonii extract and to elucidate its underlying mechanism. MATERIALS AND METHODS: An activity-guided fractionation was realized using MTT assay. To investigate if the bioactive compound daucosterol (CA2) accounted for the previously observed anticancer effects of the C. adansonii extract, it was tested on cell growth, cell proliferation, cell cycle, cell death mechanism and cell migration. In addition, cell cycle- and apoptosis-regulating proteins were assessed by Western blotting. RESULTS: Daucosterol (CA2), a steroid saponin, was identified as major anticancer principle of the C. adansonii extract. Daucosterol significantly inhibited LNCaP, DU145 and PC3 prostate carcinoma cell growth and proliferation at the optimal concentration of 1⯵g/mL. It also significantly increased the number of late apoptotic (DU145) and apoptotic (PC3) cells. The number of cells in S phase increased in DU145, while the number of G0/G1 cells decreased. Cell cycle proteins (cdk1, pcdk1, cyclin A and B) were down-regulated in DU145 and PC3 cells, whereas only cdk2 was down-regulated in PC3 cells. Moreover, the anti-apoptotic Akt, pAKT and Bcl-2 proteins were down-regulated, while the pro-apoptotic protein Bax was up-regulated. CA2 induced anti-metastatic effects by decreasing chemotaxis and cell migration, while it increased cell adhesion to fibronectin and collagen matrix. CONCLUSION: These results suggest that daucosterol is the major active principle responsible at least in part for the anticancer effect of the extract of Crateva adansonii.
Assuntos
Capparaceae/química , Extratos Vegetais/farmacologia , Neoplasias da Próstata/tratamento farmacológico , Sitosteroides/farmacologia , Apoptose/efeitos dos fármacos , Bioensaio , Camarões , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Fracionamento Químico , Quimiotaxia/efeitos dos fármacos , Regulação para Baixo/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Masculino , Medicinas Tradicionais Africanas/métodos , Invasividade Neoplásica/prevenção & controle , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Neoplasias da Próstata/patologia , Proteínas Proto-Oncogênicas c-akt/metabolismo , Proteínas Proto-Oncogênicas c-bcl-2/metabolismo , Sitosteroides/isolamento & purificação , Regulação para Cima/efeitos dos fármacosRESUMO
BACKGROUND: Benign prostatic hyperplasia (BPH) is a pathological condition affecting older men. BPH complications often lead to deterioration in the quality of life. Serenoa repens (Saw Palmetto) is used for treating lower urinary tract infections in traditional medicine. METHODS: This study was performed to compare the efficacy of ß-sitosterol enriched saw palmetto oil (VISPO) and conventional saw palmetto oil (SPO) extracted using supercritical fluid extraction, in alleviating the BPH complications using testosterone-induced BPH model rats. The animals received testosterone (5 mg/kg s.c.) with or without SPO and VISPO (200 and 400 mg/kg b.w.) or Finasteride (1 mg/kg b.w.) p.o. for 28 days. At the end of the experiment, overnight fasted animals were euthanized, blood samples collected for serum analysis of testosterone. Prostate tissue histomorphology was examined by hematoxylin and eosin (H&E) staining. Western blot analysis was performed using prostate tissue homogenates. RESULTS: VISPO exhibited superior efficacy compared to SPO as evident from the significant decrease in prostate weight to body weight ratio, serum testosterone level and increase in growth inhibition of prostate tissue compared to BPH group (p < 0.001). Histological examination of prostate tissue samples showed that VISPO treatment was comparatively better than SPO in improving the hyperplastic patterns. Further, VISPO significantly regulated the expression of inflammatory and apoptotic marker proteins in BPH rats. CONCLUSION: Our data provide experimental evidence that ß-sitosterol enriched saw palmetto oil could be higher efficacious in treating the BPH complications compared to the conventional saw palmetto oil preparations.
Assuntos
Fitosteróis/administração & dosagem , Extratos Vegetais/administração & dosagem , Hiperplasia Prostática/tratamento farmacológico , Proteínas Proto-Oncogênicas c-bcl-2/genética , Proteína X Associada a bcl-2/genética , Animais , Cromatografia com Fluido Supercrítico , Humanos , Masculino , Fitosteróis/isolamento & purificação , Fitoterapia , Extratos Vegetais/isolamento & purificação , Próstata/efeitos dos fármacos , Próstata/imunologia , Hiperplasia Prostática/sangue , Hiperplasia Prostática/induzido quimicamente , Hiperplasia Prostática/imunologia , Proteínas Proto-Oncogênicas c-bcl-2/imunologia , Ratos , Ratos Wistar , Serenoa/química , Sitosteroides/administração & dosagem , Sitosteroides/isolamento & purificação , Testosterona/efeitos adversos , Testosterona/sangue , Proteína X Associada a bcl-2/imunologiaRESUMO
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 24â h of exposure time, while ß-sitosterol glucoside revealed no activity against the nematode.
Assuntos
Antinematódeos/química , Ceramidas/química , Tagetes/química , Animais , Antinematódeos/isolamento & purificação , Antinematódeos/farmacologia , Ceramidas/isolamento & purificação , Ceramidas/farmacologia , Flores/química , Flores/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Conformação Molecular , Sitosteroides/química , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologia , Estigmasterol/química , Estigmasterol/isolamento & purificação , Estigmasterol/farmacologia , Tagetes/metabolismo , Tylenchoidea/efeitos dos fármacosRESUMO
α-glucosidase is responsible for the hydrolysis of complex carbohydrates into simple absorbable glucose and causes postprandial hyperglycemia. α-glucosidase inhibition is thus the ideal target to prevent postprandial hyperglycemia. The present study was therefore designed to analyze the effects of various compounds isolated from Dryopteris cycadina against α-glucosidase including ß-Sitosterol 1, ß-Sitosterol3-O-ß-d-glucopyranoside 2, 3, 5, 7-trihydroxy-2-(p-tolyl) chorman-4-one 3, Quercetin-3-0-ß-d-glucopyranoside (3/â0-3///)- ß-d- Quercetin -3-0- ß â»d-galactopyranoside 4 and 5, 7, 4/-Trihydroxyflavon-3-glucopyranoid 5. The in vitro spectrophotometric method was used for the analysis of test compounds against possible inhibition. Similarly, molecular docking studies were performed using the MOE software. These compounds showed concentration-dependent inhibition on α-glucosidase, and compounds 1 (IC50: 143 ± 0.47 µM), 3 (IC50:133 ± 6.90 µM) and 5 (IC50: 146 ± 1.93 µM) were more potent than the standard drug, acarbose (IC50: 290 ± 0.54 µM). Computational studies of these compounds strongly supported the in vitro studies and showed strong binding receptor sensitivity. In short, the secondary metabolites isolated from D. cycadina demonstrated potent α-glucosidase inhibition that were supported by molecular docking with a high docking score.
Assuntos
Dryopteris/química , Inibidores de Glicosídeo Hidrolases/química , Acarbose/química , Acarbose/isolamento & purificação , Galactose/química , Galactose/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Simulação de Acoplamento Molecular , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Ligação Proteica , Quercetina/química , Quercetina/isolamento & purificação , Metabolismo Secundário , Sitosteroides/química , Sitosteroides/isolamento & purificação , Relação Estrutura-Atividade , alfa-Glucosidases/metabolismoRESUMO
A novel monolithic column was prepared by in-situ free radical polymerization using N-methylolacrylamide (NMA) and N,N-diethylacrylamide (DEA) as co-monomers. The monolith was characterized by scanning electron microscopy (SEM) and its nitrogen adsorption-desorption isotherm, and it was used as a solid phase extraction (SPE) absorbent for the online enrichment of ß-sitosterol by high performance liquid chromatography. The optimized method had good linearity, and the linear regression coefficient was 0.998. The limit of detection (LOD) and the limit of quantification (LOQ) were 0.006â¯mg/mL and 0.02â¯mg/mL, respectively. The interday and intraday accuracies were less than 7.28%. The spiked recoveries of ß-sitosterol in the six plant oil were 90.96-103.56%. The maximum amount of ß-sitosterol adsorbed on the monolithic column was 12.69â¯mg/g, and the enrichment factor of ß-sitosterol was 78. The results showed that the monolith could be used as an online SPE absorbent for the determination of ß-sitosterol in plant oil samples.
Assuntos
Óleos de Plantas/química , Polímeros/química , Sitosteroides/análise , Adsorção , Cromatografia Líquida de Alta Pressão , Limite de Detecção , Reprodutibilidade dos Testes , Sitosteroides/isolamento & purificação , Extração em Fase SólidaRESUMO
Anethum sowa L. has been used as a spice herb in the Asian and European culinary systems to add flavour and taste. The studied plant has diverse folkloric medicinal value. Present study was designed to isolate phytochemicals from the hexane, chloroform and ethyl acetate extracts of the roots by various chromatographic techniques. Based on spectral analysis (IR, LC-MS, NMR) the isolated compounds were identified as physcione (1), ß-sitosterol (2), stigmasterol (3), 2-oxo-3-propyl-2H-chromene-7-carboxylic acid (4), bergapten (5), 3-ethyl-7-hydroxy-2H-chromen-2-one (6) and graveolone (7). The mentioned compounds have been isolated for the first time from the roots part of the plant. Based on extensive literature review, physcione and bergapten were inferred to exhibit crucial bioactivities including inhibitory efficacy against various forms of cancer. Accordingly, in the present research approach molecular docking investigations of the isolated phytochemicals have been robustly executed with different oncogenes that have been reported to be actively involved in various forms of carcinoma. In silico investigations encompassing molecular docking analysis and drug-likeness profiling was executed to estimate the potential therapeutic tendencies of the phytochemicals targeted towards effective cancer therapy. Current investigation offers meaningful know-how pertaining to potential anticancer activities of the phytochemicals extracted from the roots of Anethum sowa L. and might open up new revenues towards effective drug development against cancer.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apiaceae/química , Simulação de Acoplamento Molecular , Extratos Vegetais/farmacologia , Raízes de Plantas/química , 5-Metoxipsoraleno/química , 5-Metoxipsoraleno/isolamento & purificação , 5-Metoxipsoraleno/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Benzopiranos/química , Benzopiranos/isolamento & purificação , Benzopiranos/farmacologia , Ácidos Carboxílicos/química , Ácidos Carboxílicos/isolamento & purificação , Ácidos Carboxílicos/farmacologia , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Metoxaleno/análogos & derivados , Metoxaleno/química , Metoxaleno/isolamento & purificação , Metoxaleno/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Sitosteroides/química , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologia , Estigmasterol/química , Estigmasterol/isolamento & purificação , Estigmasterol/farmacologiaRESUMO
ß-Sitosterol is a well known phytosterol in plants, but owing to its poor solubility in typical media, determining its cellular mechanisms has been proven to be difficult. In this study, we investigated the anti-inflammatory activity of ß-sitosterol (BSS) isolated from Moringa oleifera in two cell lines. Over a dose range of 7.5 to 30 µM, BSS dispersed well in the medium as nanoparticles with diameters of 50 ± 5 nm and suppressed the secretion of inflammatory factors from keratinocytes and macrophages induced by PGN, TNF-α, or LPS, such as TNF-α, IL-1ß, IL-6, IL-8, and ROS, separately. In addition, BSS significantly reduced the expression of NLRP3, a key component of NLRP3 inflammasomes, and inhibited the activation of caspase-1. There was partial inhibition of NF-κB in macrophages. This is the first study to report an increase in the solubility of nearly water-insoluble phytosterols via the formation of nanoparticles and to delineate the formulation's capacity to inhibit the signal transduction pathways of inflammation in macrophages.
Assuntos
Anti-Inflamatórios/química , Moringa oleifera/química , Nanopartículas/química , Sitosteroides/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/uso terapêutico , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/uso terapêutico , Caspase 1/metabolismo , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Citocinas/metabolismo , Composição de Medicamentos , Humanos , Queratinócitos/metabolismo , Macrófagos/metabolismo , Camundongos , Tamanho da Partícula , Transdução de Sinais/efeitos dos fármacos , Sitosteroides/isolamento & purificação , Sitosteroides/uso terapêutico , Solubilidade , Propriedades de SuperfícieRESUMO
Ichnocarpus frutescens, a climber plant, is distributed all over India. As its different parts are used as anti-inflammatory agent, so we re-investigated the roots to isolate compounds and evaluate its biological efficacy. Also, in-silico molecular docking was carried out to elucidate the structure activity relationship (SAR) of isolated compounds toward identifies the drug target enzyme with validation, which was further supported by anti-inflammatory in-vitro and in-vivo experimental models. The compounds have been undertaken mainly to investigate the anti-inflammatory and analgesic efficacy along with molecular docking investigation followed by anti-proteinase, anti-denaturation and cyclooxygenase (COX) inhibition studies. Inflammatory cytokines like TNF-α and IL-6 were assayed from lipopolysaccharides (LPS) and Concavallin (CON A) stimulated human PBMC derived macrophages by Enyme linked immune sorbent assay (ELISA) method. The purity index of the lead compound was determined by HPLC. The compounds were illustrated as 2-hydroxy tricosanoic acid (1), stigmasterol glucoside (2), stigmasterol (3), ß-sitosterol (4) and ß-sitosterol glucoside (5). The test molecules showed significant anti-denaturation, anti-proteinase and analgesic effect validated with docking study. Compounds exhibited anti-inflammatory and pain killing action due to dexamethasone like phytosterol property. Promising anti-denaturation and anti-proteinase activity offered by the compound 5, may hold its promise to fight against arthritis by rejuvenating the osteoblast cells and destroying the bone-resorpting complex of hydrated protein, bone minerals by secreting the acid and an enzyme collagenase along with pain management. The lead bioactive compound i.e. ß-sitosterol glucoside (compound 5) demonstrated considerable anti-inflammatory activity showing more than 90% protection against the inflammatory cytokines at 50⯵M dose. The anti-denaturation and COX-2 inhibition shown by the compound 5 was also noteworthy with the significant IC50 (ranging from 0.25 to 2.56⯵M) that also supporting its future promise for developing as anti-inflammatory agent. Since the most bio-active compound (5) elicit promising acute anti-inflammatory action and peripheral anti-nociceptive pain killing action with a significant ED50 dose of 3.95 & 2.84â¯mg/kg i.p. respectively in the in-vivo animal model. It could suggest its potentiality as a good in-vivo bio available agent to be an emerging anti-inflammatory drug regimen scaffold in the future. It also establishes significant in-vitro and in-vivo result co-relation. Therefore, the compound 5 could be believed as a potent lead for designing anti-inflammatory, anti-arthritic drug or pain killer without showing any untoward effect.
Assuntos
Apocynaceae/química , Inflamação/tratamento farmacológico , Dor Nociceptiva/tratamento farmacológico , Esteroides/administração & dosagem , Analgésicos/farmacologia , Anti-Inflamatórios/farmacologia , Citocinas/metabolismo , Ácidos Graxos Insaturados/química , Ácidos Graxos Insaturados/isolamento & purificação , Glucosídeos/química , Glucosídeos/isolamento & purificação , Humanos , Inflamação/patologia , Interleucina-6/genética , Leucócitos Mononucleares/efeitos dos fármacos , Lipopolissacarídeos/química , Macrófagos/efeitos dos fármacos , Simulação de Acoplamento Molecular , Dor Nociceptiva/patologia , Percepção da Dor/efeitos dos fármacos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Sitosteroides/química , Sitosteroides/isolamento & purificação , Esteroides/química , Esteroides/isolamento & purificação , Estigmasterol/análogos & derivados , Estigmasterol/química , Estigmasterol/isolamento & purificação , Fator de Necrose Tumoral alfa/genéticaRESUMO
The present work is to study the chemical constituents from petroleum ether fraction of Tibetan medicine Swertia chirayita by column chromatography and recrystallization. The structures were identified by physical and chemical properties and spectral data as swerchirin (1), decussatin (2), 1,8-dihydroxy-3,5,7-trimethoxyxanthone (3), 1-hydroxy-3,5,7,8-tetramethoxyxanthone (4), bellidifolin (5), 1-hydroxy-3, 7-dimethoxyxanthone (6), methylswertianin (7), 1-hydroxy-3,5-dimethoxyxanthone (8), erythrodiol (9), oleanolic acid (10), gnetiolactone (11), scopoletin (12), sinapaldehyde (13), syringaldehyde (14), and ß-sitosterol (15). Compounds 3, 4, 9, 11-14 were isolated from S. chirayita for the first time. Compounds 9 and 12 were firstly isolated from the genus Swertia. The cytotoxic activities of compounds 1, 2, 5, 7 and 8 against human pancreatic cancer cell lines SW1990 and BxPC-3,and the protective effects of these compounds against hydrogen peroxide (H2O2)-induced oxidative stress in human endothelium-derived EA.hy926 were investigated in vitro. The results showed no obvious effect at the high concentration of 50 µmolâ¢L⻹.
Assuntos
Medicamentos de Ervas Chinesas/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Swertia/química , Acroleína/análogos & derivados , Acroleína/isolamento & purificação , Alcanos , Benzaldeídos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Peróxido de Hidrogênio , Ácido Oleanólico/isolamento & purificação , Estresse Oxidativo/efeitos dos fármacos , Escopoletina/isolamento & purificação , Sitosteroides/isolamento & purificação , Xantonas/isolamento & purificaçãoRESUMO
Antrodia camphorata is a rare and precious traditional food and medicine for improving health-related conditions in Taiwan. The phytochemical research of the mushroom led to the isolation of a new naphthalenecarboxaldehyde, named as 1-Naphthalenecarboxaldehyde,3,4,4a,5,6,7,8,8a-octahydro-2-(hydroxymethyl)-5,5,8a-trimethyl (1). Meanwhile, seven other known compounds of nerolidol (2), cadinol (3), herbarulide (4), 3ß-Hydroxy-5a,8a-epidioxyergosta-6,22-diene (5), ergosta-7,22-diene-3,6-dione (6) 2,3-dimethoxy-5-methyl-p-benzoquinone (7) and ß-sitosterol (8) were also obtained from A. camphorata for the first time except compound (8). The new compound was elucidated by 2D NMR techniques (COSY, HMBC, HSQC, NOESY) and HRMS while those known compounds deduced by comparing 1H NMR and 13C NMR data with other literatures. Then, the hepG2 cell toxicity screening was conducted and the results demonstrated that only compound 7 and 8 exhibited significant toxicity to hepG2 cell at the concentration of 50 µg/mL.
Assuntos
Antrodia/química , Técnicas de Cultura/métodos , Benzoquinonas/química , Benzoquinonas/farmacologia , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Sitosteroides/química , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologia , Taiwan , Terpenos/química , Terpenos/isolamento & purificaçãoRESUMO
The aim of this study examined the characterization of extra virgin olive oil samples from the main cultivar Chemlali, grown in five olive orchards with different soil type (Sandy, Clay, Stony, Brown, Limestone and Gypsum). Volatile compounds were studied using headspace-solid phase micro-extraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS) technics. Moreover, the sterol profile was established using gas chromatography-mass spectrometry. 35 different volatile compounds were identified: alcohols, esters, aldehydes, ketones and hydrocarbons. The chemical composition of the volatile fraction was characterized by the preeminence of 2-hexenal (32.75%) and 1-hexanol (31.88%). Three sterols were identified and characterized. For all olive oil samples, ß-sitosterol (302.25 mg/kg) was the most abundant sterol. Interestingly, our results showed significant qualitative and quantitative differences in the levels of the volatile compounds and sterols from oils obtained from olive trees grown in different soil type.