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1.
Nutrients ; 13(7)2021 Jul 10.
Artigo em Inglês | MEDLINE | ID: mdl-34371875

RESUMO

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.


Assuntos
Hipocampo/efeitos dos fármacos , Momordica charantia , Neurônios/efeitos dos fármacos , Fármacos Neuroprotetores/farmacologia , Extratos Vegetais/farmacologia , Hidrocarbonetos Policíclicos Aromáticos/toxicidade , Estigmasterol/farmacologia , Vitamina E/farmacologia , Animais , Apoptose/efeitos dos fármacos , Proteínas Reguladoras de Apoptose/metabolismo , Ciclo Celular/efeitos dos fármacos , Proteínas de Ciclo Celular/metabolismo , Linhagem Celular , Citocromo P-450 CYP1A1/metabolismo , Citocromo P-450 CYP1A2/metabolismo , Hipocampo/metabolismo , Hipocampo/patologia , Camundongos , Momordica charantia/química , Neurônios/metabolismo , Neurônios/patologia , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/isolamento & purificação , Ligação Proteica , Espécies Reativas de Oxigênio/metabolismo , Estigmasterol/isolamento & purificação , Vitamina E/isolamento & purificação
2.
Molecules ; 25(9)2020 May 07.
Artigo em Inglês | MEDLINE | ID: mdl-32392823

RESUMO

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.


Assuntos
Afídeos/efeitos dos fármacos , Citrullus colocynthis/química , Inseticidas/toxicidade , Folhas de Planta/química , Sitosteroides/toxicidade , Estigmasterol/análogos & derivados , Triterpenos/toxicidade , Animais , Inseticidas/análise , Inseticidas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Sitosteroides/análise , Sitosteroides/química , Sitosteroides/isolamento & purificação , Estigmasterol/análise , Estigmasterol/química , Estigmasterol/isolamento & purificação , Estigmasterol/toxicidade , Triterpenos/análise , Triterpenos/química , Triterpenos/isolamento & purificação
3.
Molecules ; 25(10)2020 May 21.
Artigo em Inglês | MEDLINE | ID: mdl-32455580

RESUMO

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/química
4.
Nat Prod Res ; 34(4): 474-481, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30295511

RESUMO

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.


Assuntos
Ácidos Graxos/isolamento & purificação , Inibidores de Lipoxigenase/isolamento & purificação , Extratos Vegetais/química , Tagetes/química , Ácidos Graxos/farmacologia , Humanos , Inflamação/tratamento farmacológico , Inibidores de Lipoxigenase/metabolismo , Inibidores de Lipoxigenase/farmacologia , Simulação de Acoplamento Molecular , Extratos Vegetais/farmacologia , Ligação Proteica , Arábia Saudita , Estigmasterol/isolamento & purificação , Tiofenos/isolamento & purificação
5.
Pak J Pharm Sci ; 32(2): 661-667, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31081780

RESUMO

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.


Assuntos
Hyoscyamus/metabolismo , Compostos Fitoquímicos/química , Plantas Medicinais/metabolismo , Glucosídeos/química , Glucosídeos/isolamento & purificação , Glucosídeos/metabolismo , Hyoscyamus/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/metabolismo , Plantas Medicinais/química , Escopolamina/química , Escopolamina/isolamento & purificação , Escopolamina/metabolismo , Metabolismo Secundário , Sitosteroides/química , Sitosteroides/isolamento & purificação , Sitosteroides/metabolismo , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Estigmasterol/química , Estigmasterol/isolamento & purificação , Estigmasterol/metabolismo
6.
Food Chem ; 289: 313-319, 2019 Aug 15.
Artigo em Inglês | MEDLINE | ID: mdl-30955618

RESUMO

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.


Assuntos
Carotenoides/análise , Fitosteróis/análise , Óleos de Plantas/química , Espectrometria de Massas em Tandem/métodos , Tocoferóis/análise , Camellia/química , Camellia/metabolismo , Carotenoides/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Limite de Detecção , Extração Líquido-Líquido , Fitosteróis/isolamento & purificação , Sonicação , Estigmasterol/análise , Estigmasterol/isolamento & purificação , Tocoferóis/isolamento & purificação
7.
Chem Biodivers ; 16(6): e1900092, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31002745

RESUMO

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.


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 fármacos
8.
Nat Prod Res ; 33(2): 196-203, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29502449

RESUMO

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.


Assuntos
Limoninas/química , Meliaceae/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Casca de Planta/química , Extratos Vegetais/química , Escopoletina/química , Escopoletina/isolamento & purificação , Estigmasterol/química , Estigmasterol/isolamento & purificação
9.
Nat Prod Res ; 33(10): 1495-1499, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-29281898

RESUMO

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.


Assuntos
Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/farmacologia , Mimosa/química , Acarbose/farmacologia , Cromatografia Líquida/instrumentação , Cromatografia Líquida/métodos , Avaliação Pré-Clínica de Medicamentos/métodos , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Inibidores de Glicosídeo Hidrolases/química , Hipoglicemiantes/química , Hipoglicemiantes/isolamento & purificação , Hipoglicemiantes/farmacologia , Extratos Vegetais/análise , Extratos Vegetais/química , Quercetina/isolamento & purificação , Quercetina/farmacologia , Estigmasterol/isolamento & purificação , Estigmasterol/farmacologia , alfa-Glucosidases/metabolismo
10.
Nat Prod Res ; 33(5): 708-714, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-29183159

RESUMO

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.


Assuntos
Apiaceae/química , Ácidos Graxos/química , Óleos de Plantas/química , Sesquiterpenos/farmacologia , Tocoferóis/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Cromatografia Gasosa , Ácidos Graxos/isolamento & purificação , Furocumarinas/isolamento & purificação , Furocumarinas/farmacologia , Humanos , Estrutura Molecular , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Sementes/química , Sesquiterpenos/isolamento & purificação , Estigmasterol/isolamento & purificação , Estigmasterol/farmacologia , Tocoferóis/isolamento & purificação , Vitamina E
11.
Comput Biol Chem ; 78: 242-259, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30584950

RESUMO

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/farmacologia
12.
Steroids ; 139: 18-27, 2018 11.
Artigo em Inglês | MEDLINE | ID: mdl-30217788

RESUMO

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 µM 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 µM) 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 & 2.84 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/genética
13.
Nat Prod Res ; 32(21): 2565-2570, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-29355031

RESUMO

A phytochemical study carried out on the plant, Calophyllum wallichianum has led to the isolation of a new coumarin, wallimarin T (1) and a known coumarin, calanolide E (2) along with two common triterpenes, friedelin (3) and stigmasterol (4). The structures of these compounds were elucidated with the aid of spectroscopic analyses such as FT-IR, GC-MS, and NMR. MIC assay against the Bacillus bacteria were conducted on the extracts and this gave MIC values ranging from 0.313 to 1.25 mg/mL. Compound 2 was weakly inhibitory towards the Bacilli strains with MIC values ranging from 0.25-0.50 mg/mL. Wallimarin T (1) was not active towards all four bacteria. Overall, the extracts exhibited weak bactericidal properties whereas compound 2 was not bactericidal on the tested bacteria. The hexane and chloroform extracts of the plant were found to be inhibitors to the growth of Bacillus megaterium, Bacillus cereus, Bacillus pumilus and Bacillus subtilis.


Assuntos
Calophyllum/química , Cumarínicos/farmacologia , Casca de Planta/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Bacillus/efeitos dos fármacos , Cumarínicos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Malásia , Testes de Sensibilidade Microbiana , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Espectroscopia de Infravermelho com Transformada de Fourier , Estigmasterol/isolamento & purificação , Triterpenos/isolamento & purificação
14.
Med Chem ; 14(6): 556-562, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-29332591

RESUMO

BACKGROUND: Chagas disease is caused by the protozoan parasite Trypanosoma cruzi. This illness is found mainly in 21 Latin American countries and an estimated 8 million people are infected worldwide. The unsatisfactory chemotherapy provokes severe toxicity and resistant strains. Medicinal plants constitute a promising source of new drugs and remedies against all kinds of disorders, mainly infectious diseases arousing interest worldwide. OBJECTIVE: The aim of this study is the isolation, structural identification and evaluation of the trypanocidal activity of samples present in the Excoecaria lucida Sw. leaves. METHODS: Total extract (TE) of E. lucida Sw. leaves was obtained by ethanol extract therefore fractionated sequentially with hexane, ethyl acetate and n-butanol, to obtain three phases: Hex, EA and But, respectively. Ellagic acid (EL1) was purified from both EA and But phases, while EL2; a 1:1 stigmasterol-3-O-ß-D-glucopyranoside plus sitosterol-3-O-ß-D-glucopyranoside mixture was obtained from the Hex phase. Activity assays were performed using bloodstream and intracellular forms of T. cruzi and cytotoxicity assays using L929 fibroblasts. RESULTS: The EL1 and EL2 samples were more active against bloodstream trypomastigote forms with EC50 of 53.0±3.6 and 58.2±29.0 µg/mL, respectively; at 100 µg/mL. These samples also showed 70% of inhibition of L929 cells infection. Toxicity assays demonstrated that after 96 h of treatment only the fractions Hex and EA presented detectable cytotoxicity. CONCLUSION: Ellagic acid, stigmasterol-3-O-ß-D-glucopyranoside and sitosterol-3-O-ß-Dglucopyranoside are reported for the first time in E. lucida Sw. leaves as well as their biological activity studies supporting further investigations for Chagas disease treatment.


Assuntos
Extratos Vegetais/farmacologia , Tripanossomicidas/farmacologia , 1-Butanol/química , Acetatos/química , Animais , Ácido Elágico/isolamento & purificação , Ácido Elágico/farmacologia , Ácido Elágico/toxicidade , Euphorbiaceae/química , Fibroblastos/efeitos dos fármacos , Fibroblastos/microbiologia , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Glucosídeos/toxicidade , Hexanos/química , Camundongos , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Folhas de Planta/química , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologia , Sitosteroides/toxicidade , Estigmasterol/análogos & derivados , Estigmasterol/isolamento & purificação , Estigmasterol/farmacologia , Estigmasterol/toxicidade , Tripanossomicidas/isolamento & purificação , Tripanossomicidas/toxicidade , Trypanosoma cruzi/efeitos dos fármacos
15.
BMC Res Notes ; 10(1): 245, 2017 Jul 06.
Artigo em Inglês | MEDLINE | ID: mdl-28683831

RESUMO

BACKGROUND: Oleanolic acid (NZ-15), 7 α, 28-olean diol (NZ-38) and Stigmasterol (NZ-14) were isolated from the ethanolic extracts of the roots of Leea macrophylla (Family: Leeaceae) by using chromatographic analysis. This is the first report of isolation of these compounds from this plant. Their structures were constructed by spectroscopic analysis and by comparing the data with the published one. Subsequently the ethanolic extract was fractionated with two organic solvents and all the fractions were studied to evaluate their in vitro antioxidant property. METHODS: The ethanolic extract was fractionated with two organic solvents and all the fractions were studied to evaluate their in vitro antioxidant property by DPPH free radical scavenging assay, superoxide anion radical scavenging assay, nitric oxide radical scavenging assay, and reducing power assay. RESULTS: In the DPPH free radical scavenging assay and superoxide radical scavenging assay, the ethyl acetate soluble fraction of ethanolic extract revealed the highest free radical scavenging activity with IC50 value of 2.65 and 155.62 µg/ml, respectively as compared to standard ascorbic acid (IC50 value of 5.8 and 99.66 µg/ml). Ethyl acetate fraction also possessed highest reducing power activity with an EC50 value of 15.27 µg/ml compared to ascorbic acid (EC50 0.91 µg/ml). On the other hand, the carbon tetrachloride fraction exhibited most significant NO scavenging activity with IC50 value of 277.8 µg/ml that was even higher than that of standard ascorbic acid (IC50 value 356.04 µg/ml). In addition, the total phenolic contents of these extract and fractions were evaluated using Folin-Ciocalteu reagent and varied from 7.93 to 50.21 mg/g dry weight expressed as gallic acid equivalents (GAE). CONCLUSIONS: This study showed that different extracts of roots of L. macrophylla possess potential DPPH, superoxide, and NO free radical scavenging activities. The antioxidant activities of the plant extracts might be due to the presence of oleanolic acid, oleanolic acid derivative 7 α, 28-olean diol and stigmasterol.


Assuntos
Antioxidantes , Ácido Oleanólico/isolamento & purificação , Raízes de Plantas , Estigmasterol/isolamento & purificação , Vitaceae
16.
Int J Med Mushrooms ; 19(3): 257-265, 2017.
Artigo em Inglês | MEDLINE | ID: mdl-28605341

RESUMO

Piptoporus betulinus has been used in folk medicine for millennia. However, no data currently exist regarding its potential cardiovascular activity. In this work, the crude ethanolic extract and fractions (hexane, ethyl acetate, and water) with increased polarity from the partitioning process, as well as stigmasterol (the major metabolite isolated from P. betulinus), were administered orally at different doses to normotensive male Wistar rats an hour before recording mean arterial pressure, heart rate, renal blood flow, renal vascular conductance, arterial blood flow, and arterial vascular conductance. The acute oral administration of crude ethanolic extract and all fractions did not alter mean arterial pressure when compared with the control group, which received a vehicle. In addition, subchronic (14 days) oral administration of crude ethanolic extract, fractions, and stigmasterol did not alter cardiovascular parameters. In conclusion, our findings demonstrate that oral administration of organic extracts of P. betulinus did not induce cardiovascular alterations.


Assuntos
Sistema Cardiovascular/efeitos dos fármacos , Misturas Complexas/administração & dosagem , Polyporales/química , Estigmasterol/administração & dosagem , Administração Oral , Animais , Misturas Complexas/isolamento & purificação , Masculino , Ratos Wistar , Estigmasterol/isolamento & purificação
17.
Nat Prod Res ; 31(19): 2312-2315, 2017 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-28278621

RESUMO

Activity-guided fractionation for complement inhibitors led to the isolation of 22 known compounds from Viola kunawarensis. Chemical types include six sterol compounds, three coumarin compounds, five megastigmane compounds, two triterpenoid compounds, two phenylpropanoid compounds, one chlorophyll, one amide, and two lipid compounds. Among which, two sterols (stigmasta-4-ene-3ß,6ß-diol and saringosterone), one amide (aurantiamide acetate) and a norsesquiterpenoid (solalyratin B) exhibited better anti-complementary effects with CH50 values ranging from 0.02 to 0.08 mM, which are plausible candidates for developing potent anti-complementary agents.


Assuntos
Inativadores do Complemento/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Viola/química , Fracionamento Químico , Cumarínicos/isolamento & purificação , Glicosídeos/isolamento & purificação , Extratos Vegetais/química , Plantas Medicinais/química , Espirostanos/isolamento & purificação , Esteróis/química , Esteróis/isolamento & purificação , Estigmasterol/análogos & derivados , Estigmasterol/isolamento & purificação , Triterpenos/isolamento & purificação
18.
Pharm Biol ; 55(1): 1375-1379, 2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-28317412

RESUMO

CONTEXT: Despite several phytochemical studies of Premna serratifolia Linn. (Verbenaceae), the isolation of active constituents of this plant remains to be explored. OBJECTIVE: The study isolates cytotoxic terpenoids and steroids from the leaves of Premna serratifolia. MATERIALS AND METHODS: Unsaponifiable matter of hexane soluble fraction obtained from methanol extract was subjected to isolation by column chromatography and preparative TLC. Three compounds PS-01 A, PS-01B and PS-02 A were isolated. PS-01 A and PS-01B were identified by comparative TLC with authentic marker compounds followed by NMR analysis. Further PS-01B was analyzed by HR-GCMS. PS-02 A was subjected to HR-LCMS. All isolated compounds/fractions were evaluated for cytotoxic activity by BSL bioassay and using cell lines A549, HepG2 and L6. RESULTS: Three compounds were isolated from the leaf extract by bioactivity-guided fractionation. Two of which, namely, PS-01 A (oleanolic acid) and PS-02 A (unknown) were found to be terpenoids and PS-01B was identified as steroid (stigmasterol). PS-02 A compound is to be purified and characterized further. All three compounds PS-01 A, PS-01B, PS-02 A showed cytotoxicity by BSL bioassay (LC50 value of 54.49, 30.83, 16.32 ppm, respectively) and by cell line study where isolate PS-02 A has shown more cytotoxicity with LC50 values of 66.77 and 53.72 µg/mL with A549 and HepG2 cells, respectively, when compared with other isolates. CONCLUSION: Bioactivity guided fractionation of Premna serratifolia leaves succeeded into isolation of two terpenoids and one steroid compound with significant cytotoxic activity. Here we report the isolation of these cytotoxic terpenoids/steroids from this plant for the first time which could be developed as anticancer agents.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Neoplasias Hepáticas/tratamento farmacológico , Neoplasias Pulmonares/tratamento farmacológico , Ácido Oleanólico/farmacologia , Extratos Vegetais/farmacologia , Estigmasterol/farmacologia , Verbenaceae/química , Células A549 , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/toxicidade , Sobrevivência Celular/efeitos dos fármacos , Cromatografia em Camada Fina , Relação Dose-Resposta a Droga , Cromatografia Gasosa-Espectrometria de Massas , Células Hep G2 , Hexanos/química , Humanos , Concentração Inibidora 50 , Neoplasias Hepáticas/patologia , Neoplasias Pulmonares/patologia , Espectroscopia de Ressonância Magnética , Metanol/química , Fibras Musculares Esqueléticas/efeitos dos fármacos , Fibras Musculares Esqueléticas/patologia , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/toxicidade , Fitoterapia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Folhas de Planta/química , Plantas Medicinais , Ratos , Solventes/química , Estigmasterol/isolamento & purificação , Estigmasterol/toxicidade
19.
Nat Prod Res ; 31(19): 2321-2324, 2017 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-28288517

RESUMO

The project was intended to the phytochemical characterisation from the rudimentary methanolic extract of Chenopodium ambrosioides Linn., which escorts to the isolation of stigmasterol (1), ß-sitosterol (2), octadecanoic acid (3), scopoletin (4) and 1-piperoylpiperidine (5). Literature validates the medicinal authentication of these compounds extorted from other sources, while our previous findings regarding microbial activities of different solvent systems fractions are favouring the presence of medicinally important compounds in this species. Herein, however, we report these natural products for the first time from this species.


Assuntos
Chenopodium ambrosioides/química , Extratos Vegetais/química , Plantas Medicinais/química , Alcaloides/isolamento & purificação , Benzodioxóis/isolamento & purificação , Metanol/química , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/isolamento & purificação , Piperidinas/isolamento & purificação , Alcamidas Poli-Insaturadas/isolamento & purificação , Sitosteroides/isolamento & purificação , Solventes/química , Estigmasterol/isolamento & purificação
20.
Mar Biotechnol (NY) ; 19(1): 65-75, 2017 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-28138935

RESUMO

Hizikia fusiforme, a brown seaweed, has been utilized as a health food and in traditional medicine. In this study, we investigated whether enzyme-modified H. fusiforme extracts (EH) have immunological effects compared with normal H. fusiforme extracts (NH). The effects of NH and EH on immune responses were investigated by assessing nitric oxide (NO) production, phagocytosis, and cytokine secretion in RAW 264.7 murine macrophages and mice. Also, fucosterol was evaluated to find the active component of NH and EH by addressing cytotoxicity test and NO production. Both of NH and EH significantly increased cell viability and NO synthesis. Tumor necrosis factor-α (TNF-α) expression was more induced by EH with LPS treatment. Phagocytic activity, as the primary function of macrophages, was markedly induced by EH treatment. Additionally, EH encouraged splenocyte proliferation and recovered the levels of cytokines IL-1ß, IL-6, and TNF-α in mice. Finally, fucosterol increased NO production with no cytotoxicity, which means that fucosterol is an active component of EH. In conclusion, EH has the potential to modulate immune function and could offer positive therapeutic effect for immune system diseases.


Assuntos
Fatores Imunológicos/farmacologia , Linfócitos/efeitos dos fármacos , Phaeophyceae/química , Fagocitose/efeitos dos fármacos , Alga Marinha/química , Estigmasterol/análogos & derivados , Animais , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Expressão Gênica , Fatores Imunológicos/isolamento & purificação , Interleucina-1beta/genética , Interleucina-1beta/imunologia , Interleucina-6/genética , Interleucina-6/imunologia , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Linfócitos/citologia , Linfócitos/imunologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Camundongos , Óxido Nítrico/agonistas , Óxido Nítrico/biossíntese , Cultura Primária de Células , Estigmasterol/isolamento & purificação , Estigmasterol/farmacologia , Fator de Necrose Tumoral alfa/genética , Fator de Necrose Tumoral alfa/imunologia
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