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1.
Ecotoxicol Environ Saf ; 205: 111342, 2020 Dec 01.
Artigo em Inglês | MEDLINE | ID: mdl-32971455

RESUMO

Radix aconiti lateralis (Fuzi) is widely used in China as a traditional Chinese medicine for the treatment of asthenia, pain and inflammation. However, its toxic alkaloids often lead to adverse reactions. Currently, most of the toxicity studies on Fuzi are focused on the heart and nervous system, and more comprehensive toxicity studies are needed. In this study, based on the previous reports of Fuzi hepatotoxicity, serum pharmacochemistry and network toxicology were used to screen the potential toxic components of Heishunpian(HSP), a processed product of Fuzi, and to explore the possible mechanism of HSP-induced hepatotoxicity. The results obtained are expressed based on the toxicological evidence chain (TEC). It was found that 22 potential toxic components screened can affect Th17 cell differentiation, Jak-STAT signaling pathway, glutathione metabolism, and other related pathways by regulating AKT1, IL2, F2, GSR, EGFR and other related targets, which induces oxidative stress, metabolic disorders, cell apoptosis, immune response, and excessive release of inflammatory factors, eventually inducing liver damage in rats. This is the first study on HSP-induced hepatotoxicity based on the TEC concept, providing references for further studies on the toxicity mechanism of Fuzi.


Assuntos
Aconitum/química , Alcaloides/toxicidade , Doença Hepática Induzida por Substâncias e Drogas/patologia , Medicamentos de Ervas Chinesas/toxicidade , Modelos Biológicos , Alcaloides/sangue , Alcaloides/isolamento & purificação , Animais , Apoptose/efeitos dos fármacos , Doença Hepática Induzida por Substâncias e Drogas/sangue , Doença Hepática Induzida por Substâncias e Drogas/metabolismo , China , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacocinética , Masculino , Medicina Tradicional Chinesa , Estresse Oxidativo/efeitos dos fármacos , Ratos , Ratos Wistar
2.
J Chromatogr A ; 1626: 461359, 2020 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-32797838

RESUMO

The enantiomeric determination of chiral drugs in the environment is of emerging concern since their enantiomers often exhibit stereoselectivity in environmental occurrence, fate and toxicity. In this study a method based on solid-phase extraction followed by chiral liquid chromatography and high-resolution mass spectrometry has been developed for the enantiomeric determination of a group of cathinones in river water and effluent wastewater. The enantioseparation was carried out using a Chiralpak CBH column in reversed-phase mode, and optimised by evaluating the effects of flow rate, buffer concentration and organic modifier. Under optimal conditions, good enantioseparations (Rs ≥1.2) were achieved for all the analytes. Two mixed-mode cation-exchange sorbents (Oasis WCX and Oasis MCX) in solid-phase extraction were evaluated in river water. Oasis MCX sorbent showed better performance with apparent recoveries ranging from 57 to 91% and matrix effect ranging from -10 to 15%. It is worth noting that a shifting of retention times and loss of enantioresolutions in environmental water samples was observed for all the analytes when the Oasis WCX sorbent was used. The method was validated with river water and effluent wastewater samples and its overall performance was satisfactory. The method quantification limits for all the analyte enantiomers ranged from 1.0 to 2.9 ng/L in river water, and from 2.3 to 6.0 ng/L in effluent wastewater. The repeatability and reproducibility values, expressed as% relative standard deviation (n = 5) were less than 15%. The method was then applied to the analysis of river water and effluent wastewater. The racemic methylone and methedrone (EF=0.49 and 0.46, respectively) were detected at low ng/L in some of the river water samples.


Assuntos
Alcaloides/análise , Cromatografia Líquida/métodos , Espectrometria de Massas/métodos , Alcaloides/química , Alcaloides/isolamento & purificação , Reprodutibilidade dos Testes , Rios/química , Extração em Fase Sólida/métodos , Estereoisomerismo , Águas Residuárias/química , Poluentes Químicos da Água/análise , Poluentes Químicos da Água/química , Poluentes Químicos da Água/isolamento & purificação
3.
J Chromatogr A ; 1625: 461286, 2020 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-32709336

RESUMO

In the past two decades, supercritical fluid chromatography has evolved from a niche application to a comprehensive technology and a fully-fledged alternative to conventional high-performance liquid chromatography. In this study, we have focused on chiral separation of synthetic cathinones in gradient supercritical fluid chromatography coupled to mass spectrometry using an inverse gradient of a make-up solvent. Synthetic cathinones possess an amphetamine-like effect and, therefore, are frequently being offered on the Internet as a replacement for illicit drugs. Cathinones are chiral compounds, however, they are usually marketed and used as racemic mixtures. Since the effect of individual enantiomers can significantly vary, there is a need for the development of enantioseparation methods enabling to study the biological effects of individual enantiomers. Since cathinones are basic molecules, they are easily protonated (positively charged) under weakly acidic mobile phase conditions, which is a typical feature of supercritical mobile phases with an alcohol as an organic modifier. The positively charged species represent ideal analytes for ion exchangers, such as chiral zwitterion ion exchangers Chiralpak ZWIX (+) and Chiralpak ZWIX (-), which possess a positively and negatively charged unit in the molecular structure of the selectors. The presence of the positive charge in the selector's structure, functioning as a counter-ion for the positively charged analytes, significantly reduces the required amount of a buffer, which is plausible for hyphenation of such a separation system with mass spectrometry. For mass spectrometry hyphenated to supercritical fluid chromatography, the use of a make-up solvent is required to avoid analyte precipitation when using a low concentration of an organic co-solvent (modifier) in the super-/subcritical mobile phase. Hereby, we introduce a unique approach, which is based on the gradient introduction of the make-up to the post-column effluent. Using this approach, it is possible to keep constant the overall amount of the organic solvent (modifier and make-up) introduced into the mass spectrometer when using a gradient of the organic modifier. We show that the developed gradient elution method facilitates the chiral separation of all employed analytes, while the mobile-phase gradient compensation by the inverse make-up gradient enables their detection with high signal intensities.


Assuntos
Alcaloides/química , Alcaloides/isolamento & purificação , Cromatografia com Fluido Supercrítico/métodos , Espectrometria de Massas/métodos , Reologia , Solventes/química , Alcaloides/síntese química , Cromatografia Líquida de Alta Pressão , Pressão , Estereoisomerismo , Temperatura
4.
Chem Biol Interact ; 327: 109146, 2020 Aug 25.
Artigo em Inglês | MEDLINE | ID: mdl-32561335

RESUMO

Evodiae Fructus (EF), the dried nearly mature scented fruit of Tetradium ruticarpum (A.Juss.) T.G.Hartley, was typically used to treat headache, abdominal pain, hernias, and menorrhagia for thousands of years. It had been reported to be a mild toxic herb through metabolic activation mainly by CYP3A but was barely explained from pharmacokinetic interaction. The aim of the study was to investigate the role of CYP3A inducer/inhibitor in pharmacokinetics of five alkaloids (evodiamine (EVOD), rutaecarpine (RUTA), 1-methyl-2-undecyl-4(1H)-quinolone (MUDQ), 1-methyl-2-nonyl-4(1H)-quinolone (MNNQ) and evocarpine (EVOC)) associated with hepatotoxicity of EF in Sprague Dawley (SD) rats. The results demonstrated that the metabolism of the five alkaloids of EF were inhibited in presence of CYP3A inhibitor whereas the metabolism of the five alkaloids of EF were promoted in presence of CYP3A inducer. Therefore, the dose is required attention when EF is taken in conjunction with CYP3A inducer as there is an enhancement in drug metabolism, which might lead to toxicity.


Assuntos
Alcaloides/farmacocinética , Indutores do Citocromo P-450 CYP3A/farmacologia , Inibidores do Citocromo P-450 CYP3A/farmacologia , Evodia/química , Alcaloides/sangue , Alcaloides/isolamento & purificação , Animais , Cromatografia Líquida de Alta Pressão , Dexametasona/farmacologia , Meia-Vida , Cetoconazol/farmacologia , Masculino , Ratos , Ratos Sprague-Dawley , Espectrometria de Massas em Tandem
5.
Exp Parasitol ; 213: 107902, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32353376

RESUMO

Natural compounds played an important role for prevention and treatment of the disease as well as are the important compounds for the design of the new bioactive compounds. In this study, eight tropolone alkaloids were isolated from Colchicum kurdicum including colchicoside, 2-demethyl colchicine, 3-demethyl colchicine, demecolcine, colchifoline, N-deacetyl-N-formyl colchicine, colchicine and cornigerine by column and preparative thin layer chromatography. The chemical structures were identified by 1H NMR and 13C NMR spectroscopy. Moreover, the antileishmanial activity on Leishmania major, anti-inflammatory activity, iron chelating activity and toxicity studies including hemolytic activity, brine shrimp toxicity, cytotoxicity and acute toxicity and docking study of all isolated bioactive compounds were evaluated. As result, colchicoside and colchicine had potent leishmanicidal effects and N-deacetyl-N-formyl colchicine and cornigerine had the highest anti-inflammatory effects. All compounds had the significant iron chelating activity. According to toxicity studies, isolated compounds showed the low hemolytic activity and cytotoxicity, high LC50, LC90 and LD50. In the molecular docking study, colchicoside had the high dockscore. According to the study, with future studies all isolated compounds could be used for design the novel antileishmanial drugs.


Assuntos
Alcaloides/farmacologia , Colchicum/química , Leishmania major/efeitos dos fármacos , Extratos Vegetais/farmacologia , Tripanossomicidas/farmacologia , Alcaloides/química , Alcaloides/isolamento & purificação , Simulação de Acoplamento Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Tropolona/química , Tripanossomicidas/química , Tripanossomicidas/isolamento & purificação
6.
Psychopharmacology (Berl) ; 237(7): 2111-2124, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32363440

RESUMO

INTRODUCTION: Gelsemine is a natural alkaloid extracted from Gelsemium elegans Benth., a traditional Chinese medicinal herb. Gelsemine has been shown to penetrate the brain, and could produce neurological activities, such as anxiolytic and neuralgia-alleviating effects, suggesting that this natural compound might be used for treating nervous system diseases. RESULTS: In this study, we have found, for the first time, that gelsemine at low concentrations (5-10 µg/kg) significantly alleviated cognitive impairments induced by ß-amyloid (Aß) oligomer, a main neurotoxin of Alzheimer's disease (AD). In addition, gelsemine substantially prevented Aß oligomer-induced over-activation of microglia and astrocytes, indicating that gelsemine might reduce AD-related gliosis. Consistently, gelsemine inhibited the over-expression of pro-inflammatory cytokines, including interleukin-1ß (IL-1ß), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α), in the brain of mice. Moreover, gelsemine largely increased the expression of pSer9-glycogen synthase kinase-3ß (GSK3ß), and decreased the hyper-phosphorylation of tau protein as evidenced by Western blotting analysis. Furthermore, gelsemine prevented Aß oligomer-induced reduction of PSD-95, a representative post-synaptic protein. CONCLUSION: All these results directly demonstrated the anti-Aß oligomer neuroprotective properties of gelsemine, opening a novel perspective for the development of gelsemine-based therapeutics against Aß-associated neurodegeneration disorders, including AD in particular.


Assuntos
Alcaloides/uso terapêutico , Peptídeos beta-Amiloides/toxicidade , Disfunção Cognitiva/tratamento farmacológico , Medicamentos de Ervas Chinesas/uso terapêutico , Gelsemium , Mediadores da Inflamação/antagonistas & inibidores , Fragmentos de Peptídeos/toxicidade , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Doença de Alzheimer/induzido quimicamente , Doença de Alzheimer/tratamento farmacológico , Doença de Alzheimer/metabolismo , Animais , Encéfalo/efeitos dos fármacos , Encéfalo/metabolismo , Disfunção Cognitiva/induzido quimicamente , Disfunção Cognitiva/metabolismo , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Mediadores da Inflamação/metabolismo , Masculino , Camundongos , Camundongos Endogâmicos ICR
7.
Zhongguo Zhong Yao Za Zhi ; 45(6): 1393-1398, 2020 Mar.
Artigo em Chinês | MEDLINE | ID: mdl-32281353

RESUMO

An UPLC method was established for the direct determination of six major bioactive isosteroidal alkaloids, namely peimisine, imperialine, sipeimine-3-D-glucoside, verticinone, verticine and hupehenine from the bulbus of Fritillaria(Beimu), a commonly used antitussive traditional Chinese medicinal(TCM) herb. An Acquity UPLC~(TM) CSH C_(18) column(2.1 mm×100 mm, 1.7 µm) was used for all analysis. The investigated six compounds were all separated with gradient mobile phase consisting of 0.02% diethylamine-water-methanol at a flow rate of 0.3 mL·min~(-1). The temperature of sample manager was set at 20 ℃. Drift tube temperature was 45 ℃, and spray parameter was 40% with injection volume of 1 µL. Then, the further quality assessment of Beimu was carried out by cluster analysis(CA) and principal component analysis(PCA). The investigated all had good linearity(r≥0.998 9) over the tested ranges. The method is simple, accurate and reproducible, and can be used for determining the content of six major bioactive isosteroidal alkaloids.


Assuntos
Alcaloides/análise , Medicamentos de Ervas Chinesas/química , Fritillaria/química , Alcaloides/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/isolamento & purificação , Raízes de Plantas/química
8.
J Chromatogr A ; 1621: 461045, 2020 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-32201036

RESUMO

New zwitterionic (ZIC) stationary phases (SPs) are synthesized with the click and conventional bonding of tyrosine to silica gel. Infrared spectra and elemental analysis demonstrate the successful click and conventional bonding of this ZIC group on silica particles by the surface coverage including 2.36 and 0.75 µm m-2, respectively. Given the above-mentioned explanation, the present study evaluated the retention mechanism and chromatographic manners of polar compounds on these new materials under hydrophilic interaction liquid chromatography (HILIC) conditions. Based on the results, the Click-Tyrosine Stationary Phase provided good HILIC characteristics when it was applied to separate phenolic compounds, amino acids, alkaloids, and nucleobases compared to bare silica gel SP and even conventional tyrosine SPs. Further, this new Click-Tyrosine-SP represented appropriate HILIC features and column efficiency (the theoretical plate number was up to 50,000 plates m-1 for thebaine). Furthermore, the study investigated the effect of solute polarity (the number of the hydroxyl group of phenolic compounds) and hydrophobicity (the number of the side chain of aliphatic amino acids) on retention behaviors. Finally, some important factors were studied as the potential variables for guiding the retention behavior of the polar compound in HILIC condition including solvent composition, salt concentration, and the buffer pH of the mobile phase.


Assuntos
Cromatografia Líquida/métodos , Tirosina/química , Alcaloides/análise , Alcaloides/isolamento & purificação , Aminoácidos/análise , Aminoácidos/isolamento & purificação , Química Click , Interações Hidrofóbicas e Hidrofílicas , Fenóis/análise , Fenóis/isolamento & purificação , Sílica Gel/química
9.
Am J Chin Med ; 48(2): 407-428, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32138533

RESUMO

Chemotherapy-induced peripheral neuropathy (CIPN) is a common complication of cisplatin, which is characterized by intolerable paresthesia, burning, and hyperalgesia, and severely impacts the life quality of patients. However, no clearly potent drug has been found for clinical medication due to its undefined mechanism. Corydalis Saxicola Bunting, a traditional Chinese medicine, has been proven to work well in anti-inflammation, blood circulations improvement, hemostasis, and analgesia. This study was designed to observe the effects of Corydalis saxicola Bunting total alkaloids (CSBTA) on cisplatin-induced neuropathic pain and to explore its potential mechanisms. In this study, the rats received intraperitoneal injection of 2mg/kg cisplatin twice a week for five weeks. Meanwhile, oral administration of low (30mg/kg)-, medium (60mg/kg)- and high (120mg/kg)-dose CSBTA were given daily for five weeks. By using Von-frey hair, heat radiant and -80∘C cold acetone, we found that CSBTA could obviously relieve cisplatin-induced mechanical, heat, and cold hyperalgesia. It has been verified that cisplatin-induced peripheral neuropathy is related to intraepidermal nerve fibers loss and activation of inflammation downstream. Our research found that Tumor necrosis factor-alpha (TNF-α), Interleukin-1beta (IL-1ß), and Prostaglandin E2 (PGE2) were significantly increased by 10 intraperitoneal injections of cisplatin, and such pro-inflammation cytokines could be reduced via CSBTA administration. Besides, in the cisplatin model group, the neuronal structures of dorsal root ganglia (DRG) were severely damaged and the loss of intraepidermal nerve fibers occurred; but in the CSBTA administration groups, all above pathological changes were improved. Moreover, CSBTA could normalize the overexpression levels of p-p38 and Transient receptor potential vanilloid receptor (TRPV1) induced by cisplatin in DRG, trigeminal ganglion (TG), spinal cord, and foot of rats. In summary, we considered that CSBTA exerted its therapeutic effects by ameliorating neuronal damages, improving intraepidermal nerve fiber (IENF) loss, and inhibiting inflammation-induced p38 phosphorylation to block TRPV1 activation. These findings were the first to confirm the analgesic effect of CSBTA on CIPN and suggested a novel strategy for treating CIPN in clinic.


Assuntos
Alcaloides/farmacologia , Alcaloides/uso terapêutico , Analgésicos , Cisplatino/efeitos adversos , Corydalis/química , Neuralgia/induzido quimicamente , Neuralgia/genética , Fitoterapia , Canais de Cátion TRPV/metabolismo , Alcaloides/isolamento & purificação , Animais , Neuralgia/tratamento farmacológico , Ratos
11.
Alkaloids Chem Biol ; 83: 1-112, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32098648

RESUMO

Lamellarins are marine alkaloids containing fused 14-phenyl-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinoline or non-fused 3,4-diarylpyrrole-2-carboxylate ring systems. To date, more than 50 lamellarins have been isolated from a variety of marine organisms, such as mollusks, tunicates, and sponges. Many of them, especially fused type I lamellarins, exhibit impressive biological activity, such as potent cytotoxicity, topoisomerase I inhibition, protein kinases inhibition, and anti-HIV-1 activity. Due to their useful biological activity and limited availability from natural sources, a number of synthetic methods have been developed. In this chapter, we present an updated and comprehensive review on lamellarin alkaloids summarizing their isolation, synthesis, and biological activity.


Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Fármacos Anti-HIV/farmacologia , Antineoplásicos/farmacologia , Inibidores de Proteínas Quinases/farmacologia , Pirróis/isolamento & purificação , Pirróis/farmacologia , Inibidores da Topoisomerase I/farmacologia , Alcaloides/síntese química , Alcaloides/química , Animais , Fármacos Anti-HIV/síntese química , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Antineoplásicos/síntese química , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Humanos , Inibidores de Proteínas Quinases/síntese química , Inibidores de Proteínas Quinases/química , Inibidores de Proteínas Quinases/isolamento & purificação , Pirróis/síntese química , Pirróis/química , Inibidores da Topoisomerase I/síntese química , Inibidores da Topoisomerase I/química , Inibidores da Topoisomerase I/isolamento & purificação
12.
Molecules ; 25(2)2020 Jan 17.
Artigo em Inglês | MEDLINE | ID: mdl-31963595

RESUMO

Citrus is a globally consumed fruit with great popularity. Mandarin (Citrus reticulata cv. 'Shatangju') is a local variety, and its planting area and yield are the greatest regarding fruit tree planting in Guangdong Province, China. However, its resistance to Huanglongbing (HLB) is weak. After infection by HLB, the fruits cannot develop normally. In this study, four kinds of fruits were classified as HBG, XQG, ZQG, and DHG, according to the color of their peels. The metabolomes of the three abnormally colored groups (HBG, XQG, and ZQG) and the normally colored group (DHG) were compared using a UPLC-QQQ-MS-based metabolomics approach. In total, 913 metabolites were identified and classified into 23 different categories, including phenylpropanoids and flavonoids; among them, 215 (HBG, 177; XQG, 124; and ZQG, 62) metabolites showed differential accumulation in the three comparison groups (HBG/XQG/ZQG versus DHG). A total of 2 unique metabolites, O-caffeoyl maltotriose and myricetin were detected only in DHG samples. When comparing HBG with DHG, there were 109 decreased and 68 increased metabolites; comparing XQG with DHG, there were 88 decreased and 36 increased metabolites; comparing ZQG with DHG, 41 metabolites were decreased, and 21 metabolites were increased. Metabolic pathway enrichment analysis of these differential metabolites showed significant enrichment of the "phenylpropanoid biosynthesis" pathway in all comparison groups. The hierarchical cluster analysis of the differential metabolites of the four groups showed a clear grouping patterns. The relative contents of three phenylpropanoids, four flavonoids, two alkaloids, one anthocyanin, and two other metabolites were significantly different between each comparison group. This study might provide fundamental insight for the isolation and identification of functional compounds from the peels of citrus fruit infected with HLB and for in-depth research on the effect of HLB on the formation of fruits pigment and the development of HLB-resistant citrus varieties.


Assuntos
Citrus/química , Metabolômica/métodos , Rhizobiaceae/patogenicidade , Alcaloides/isolamento & purificação , Antocianinas/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Citrus/microbiologia , Análise por Conglomerados , Resistência à Doença , Flavonoides/isolamento & purificação , Frutas/química , Frutas/microbiologia , Espectrometria de Massas , Redes e Vias Metabólicas , Propanóis/isolamento & purificação
13.
Curr Pharm Biotechnol ; 21(7): 613-625, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-31914910

RESUMO

AIMS: The present study aims to determine the antimicrobial efficacy of Alphonsea madraspatana leaves extract against selected uropathogens. BACKGROUND: The plant Alphonsea madraspatana is an endangered species, reported to exhibit high antimicrobial activity due to the presence of phenolic compounds. Prevalence of high UTI infection and increased cases of bacterial resistance directed for alternative approach to meet the challenge of drug resistance. OBJECTIVE: Our objective is to determine antimicrobial efficacy of Alphonsea madraspatana leaves extract against selected uropathogens and subsequent in-silico analysis to predict the underlying mechanism. METHODS: Phytochemicals extraction from the dried leaves of Alphonsea madraspatana was performed using solvent gradient technique. All the extracts were subjected to preliminary phytochemical screening using liquid chromatography-mass spectrometry. Antimicrobial activity of the prepared extract was determined against the selected uropathogens using agar diffusion method. Finally, molecular docking study of the selected bio-actives was performed against a representative bacterial resistance enzyme ''DNA Gyrase". RESULTS: Methanolic extract exhibits relatively higher antimicrobial activity against the selected strains with Minimum Inhibitory Concentration (MIC) and minimum bactericidal concentration (MBC) of 1.56 ± 1 ug/mL and 6.25 ± 2 ug/mL, respectively. Phytochemical screening showed the presence of 3 flavonoids compounds such as Luteolin-7-O-glucoside, Kaempferol-3-O- rotinoside-7-O-rhamnoside and Genestein-7-O-glucoside. The results of molecular docking shows Luteolin-7-O-glucoside has best docking scores of -8.5 kcal/mol than other ligand molecules. Experimental simulation in presence of DNA Gyrase inhibitors showed lowest MIC and MBC value for E. Coli, which was found to be 1.56 ±1 ug/mL and 6.25±2 ug/mL respectively, support the docking outcomes. CONCLUSION: Outcomes of this study suggested that the methanolic extract of this plant shows good anti-microbial potential against resistant uropathogens.


Assuntos
Alcaloides/farmacologia , Annonaceae/química , Antibacterianos/farmacologia , Flavonoides/farmacologia , Extratos Vegetais/farmacologia , Escherichia coli Uropatogênica/efeitos dos fármacos , Alcaloides/isolamento & purificação , Antibacterianos/isolamento & purificação , DNA Girase/metabolismo , Flavonoides/isolamento & purificação , Testes de Sensibilidade Microbiana , Simulação de Acoplamento Molecular , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Escherichia coli Uropatogênica/enzimologia
14.
Fitoterapia ; 140: 104434, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31760067

RESUMO

Fritillaria cirrhosa bulbus is a Chinese folk herb famous for its antitussive, expectorant, anti-asthma and anti-inflammatory properties, and is widely used to treat respiratory diseases. However, the impacts of F. cirrhosa bulbus on oxidative stress are still unkown. In the present study, we investigated the potential effect and mechanism of six isosteroid alkaloids with different chemical structures from F. cirrhosa bulbus on protection against cigarette smoke-induced oxidative stress in RAW264.7 macrophages. The results showed that six isosteroid alkaloids reduced reactive oxygen species (ROS) production, elevated glutathione (GSH) level and promoted heme oxygenase (HO-1) expression, which is in association with induction of NF-E2-related factor 2 (Nrf2) nuclear translocation and up-regulation of Nrf2 expression. Among these alkaloids, verticinone, verticine, imperialine-3-ß-D-glucoside, delavine and peimisine exhibited more potent effect against CSE-induced oxidative stress than that of imperialine. These findings for the first time demonstrated that F. cirrhosa bulbus may play a protective role in cellular oxidative stress by activating Nrf2-mediated antioxidant pathway. Furthermore, the differences in antioxidant effects of these alkaloids were compared, as well as the corresponding structure-activity relationships were preliminarily elucidated. This suggested that F. cirrhosa bulbus might be a promising therapeutic treatment for the prevent of oxidative stress-related diseases.


Assuntos
Alcaloides/farmacologia , Fritillaria/química , Estresse Oxidativo/efeitos dos fármacos , Fumaça/efeitos adversos , Alcaloides/isolamento & purificação , Animais , Glutationa/metabolismo , Heme Oxigenase-1/metabolismo , Proteínas de Membrana/metabolismo , Camundongos , Estrutura Molecular , Fator 2 Relacionado a NF-E2/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Plantas Medicinais/química , Células RAW 264.7 , Espécies Reativas de Oxigênio/metabolismo , Relação Estrutura-Atividade , Produtos do Tabaco
15.
Chem Biodivers ; 17(1): e1900600, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31793197

RESUMO

Four new hetisine-type C20 -diterpenoid alkaloids, named as coreanines A-D (1-4), were isolated from the roots of Aconitum coreanum, together with thirteen known alkaloids (5-17). Their structures were elucidated by extensive spectroscopic methods including IR, HR-ESI-MS and NMR techniques. All the isolated compounds were screened for the acetylcholinesterase (AChE) inhibitory effects, and none of them showed considerable inhibitory activity.


Assuntos
Acetilcolinesterase/metabolismo , Aconitum/química , Alcaloides/farmacologia , Inibidores da Colinesterase/farmacologia , Diterpenos/farmacologia , Raízes de Plantas/química , Alcaloides/química , Alcaloides/isolamento & purificação , Animais , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Electrophorus , Estrutura Molecular
16.
Fitoterapia ; 140: 104406, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31698061

RESUMO

One new quinoline alkaloid (1), two new bisabolane-type sesquiterpene derivatives (2 and 3), and a new natural product (4) along with ten known compounds (514) were isolated from the deep sea-derived fungus Aspergillus sp. SCSIO06786 which cultured on solid rice medium. Three new structures were elucidated by analysis of 1D/2D NMR data and HR-ESI-MS. The absolute configurations of 2 and 3 were established by comparison of the experimental and reported ECD values. Compounds 11-13 exhibited moderate selective inhibitory activities against the tested pathogenic bacteria with MIC values among 3.13-12.5 µg/mL.


Assuntos
Alcaloides/isolamento & purificação , Aspergillus/química , Sesquiterpenos Monocíclicos/isolamento & purificação , Quinolinas/isolamento & purificação , Água do Mar/microbiologia , Sesquiterpenos/isolamento & purificação , Alcaloides/farmacologia , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Sedimentos Geológicos/microbiologia , Oceano Índico , Testes de Sensibilidade Microbiana , Estrutura Molecular , Sesquiterpenos Monocíclicos/farmacologia , Quinolinas/farmacologia , Sesquiterpenos/farmacologia
17.
Phytochemistry ; 170: 112186, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31731240

RESUMO

Chemical investigation of the traditional Chinese medicine, Murraya kwangsiensis, led to the isolation of 16 undescribed biscarbazole alkaloids, kwangsines A-M, two undescribed natural products, (+/-)-bispyrayafoline C, and 19 known monomeric analogues. (±)-Bispyrayafoline C and (±)-kwangsines A-C are four pairs of biscarbazole atropisomers, and they were separated by chiral HPLC to obtain the optically pure compounds. The structures of the undescribed compounds were elucidated on the basis of HRESIMS and NMR data analysis. Their absolute configurations were assigned via comparison of the specific rotation, ECD exciton coupling method, as well as comparison of experimental and calculated ECD data. A compound showed significant inhibition on NO production in lipopolysaccharide-stimulated BV-2 microglial cells, and four compounds exhibited moderate cytotoxicities against HepG2 cells, with IC50 values less than 20 µM.


Assuntos
Alcaloides/farmacologia , Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Carbazóis/farmacologia , Murraya/química , Compostos Fitoquímicos/farmacologia , Alcaloides/química , Alcaloides/isolamento & purificação , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Carbazóis/química , Carbazóis/isolamento & purificação , Linhagem Celular , Proliferação de Células/efeitos dos fármacos , Teoria da Densidade Funcional , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células Hep G2 , Humanos , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Relação Estrutura-Atividade
18.
J Chromatogr A ; 1612: 460659, 2020 Feb 08.
Artigo em Inglês | MEDLINE | ID: mdl-31708214

RESUMO

In this work, multilayer zirconia-coated silica (ZrO2/SiO2-n) microspheres were successfully produced by a straightforward hydrothermal procedure with a low concentration of Zr4+ (5 mM) under low potential of hydrogen (pH) conditions (pH = =2). The obtained ZrO2/SiO2-n materials exhibited favorable characteristics for high-performance liquid chromatography (HPLC) separation, including high surface area and pore volume, good pore structure, narrow particle size, and pore size distribution. In addition, the zirconia coverage in the mesopores was confirmed by soaking the material in 1 M NaOH solution, with the particles showing strong resistance to the basic solution. The obtained ZrO2/SiO2-n stationary phases were packed into a fused-silica capillary tubing for the separation of alkaloids in hydrophilic interaction chromatography (HILIC) mode, and a column efficiency of 47,800 plates/m was obtained for berberine on a ZrO2/SiO2-6 micro column. The ZrO2/SiO2-6 microspheres were further modified by dodecylphosphonic acid (C12P-2-ZrO2/SiO2-6); the C12P-2-ZrO2/SiO2-6 material showed great potential for application in reversed-phase liquid chromatography (RPLC) mode. The C12P-2-ZrO2/SiO2-6 micro column showed a column efficiency of 55,000 plates/m for naphthalene and 51,300 plates/m for benzene.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Hidrogênio/química , Microesferas , Ácidos Fosforosos/química , Dióxido de Silício/química , Zircônio/química , Alcaloides/análise , Alcaloides/isolamento & purificação , Cromatografia de Fase Reversa , Interações Hidrofóbicas e Hidrofílicas , Tamanho da Partícula , Porosidade , Reprodutibilidade dos Testes
19.
Phytochemistry ; 170: 112220, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31812107

RESUMO

Four previously undescribed erythrinan alkaloids, 8α-acetonylerythristemine, 8α-acetonylerysotrine, 10ß-hydroxy-11ß-methoxyerysotramidine and 3-epierysotrine, one undescribed pyrrolidine derivative, S-1-(4-hydroxy-3-methoxyphenethyl)-5-hydroxy pyrrolidin-2-one, and one undescribed amide, N-(3-hydroxy-4-methoxyphenethyl)-4-hydroxylbutanamide, along with thirteen known alkaloids were isolated from the stem barks of Erythrina strica Roxb. (Leguminosae). Their structures were identified by extensive analysis of physical, spectroscopic and spectrometric data. It's very interesting that the coexistence of 3-methoxytyramine, erythrinarbine, S-1-(4-hydroxy-3-methoxyphenethyl)-5-hydroxy pyrrolidin-2-one and N-(3-hydroxy-4-methoxyphenethyl)-4-hydroxylbutanamide that may be closely related in biosynthesis, supports the hypothetical biogenetic pathway of pyrrolo [2,1-a]isoquinoline alkaloids.


Assuntos
Alcaloides/isolamento & purificação , Erythrina/química , Compostos Fitoquímicos/isolamento & purificação , Casca de Planta/química , Extratos Vegetais/isolamento & purificação , Alcaloides/química , Compostos Fitoquímicos/química , Extratos Vegetais/química
20.
Nat Prod Res ; 34(7): 1037-1040, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30602319

RESUMO

Seven tetracyclic spiro-alkaloids, i.e. glucoerysodine (1), erysodine (2), epi-erythratidine (3), erysovine (4), erythratidine (5), erysotrine (6) and erythraline (7) were isolated from the seeds of Erythrina latissima by means of conventional separation methods and HPLC-DAD-SPE-NMR. Their structures were elucidated by spectroscopic means. This is the first report on the isolation of compounds 3, 5 and 6 from this plant. Antiplasmodial activity against the chloroquine-resistant strain Plasmodium falciparum K1 and cytotoxicity against MRC-5 cells (human fetal lung fibroblast cells) was assessed in vitro. Erysodine (2) and erysovine (4) showed moderate activity (IC50 6.53 µM and 4.05 µM, respectively), compared with the standard chloroquine (IC50 = 0.14 µM). No cytotoxicity was observed in a concentration up to 64.0 µM.


Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antimaláricos/isolamento & purificação , Erythrina/química , Extratos Vegetais/química , Alcaloides/química , Antimaláricos/química , Linhagem Celular , Cloroquina/farmacologia , Cromatografia Líquida de Alta Pressão , Di-Hidro-beta-Eritroidina/análogos & derivados , Resistência a Medicamentos , Humanos , Alcaloides Indólicos , Espectroscopia de Ressonância Magnética , Extratos Vegetais/análise , Extratos Vegetais/farmacologia , Plasmodium falciparum/efeitos dos fármacos , Sementes/química
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