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1.
J Tradit Chin Med ; 40(2): 340-342, 2020 04.
Artigo em Inglês | MEDLINE | ID: mdl-32242401

RESUMO

The management of dilated cardiomyopathy (DCM) is well established. However, a subset of patients does not have recovery from or have recurrences of left ventricular (LV) dysfunction despite receiving optimal medical therapy. Coronary microvascular dysfunction (CMD) can result from structural and functional abnormalities at the intramural and small coronary vessel level affecting coronary blood flow autoregulation and consequently leading to impaired coronary flow reserve. Dilated myocardial phenotype may be responsible for CMD in DCM. Anisodamine can exert a significant effect on relieving microvascular spasm, and improving and dredging the coronary microcirculation. However, whether CMD can be potentially improved with anisodamine to make DCM better remains incompletely understood.


Assuntos
Cardiomiopatia Dilatada/tratamento farmacológico , Doença das Coronárias/complicações , Medicamentos de Ervas Chinesas/administração & dosagem , Alcaloides de Solanáceas/administração & dosagem , Adulto , Idoso , Cardiomiopatia Dilatada/etiologia , Cardiomiopatia Dilatada/fisiopatologia , Feminino , Seguimentos , Humanos , Masculino , Microcirculação/efeitos dos fármacos , Pessoa de Meia-Idade , Scopolia/química , Função Ventricular Esquerda/efeitos dos fármacos
2.
J Sep Sci ; 42(6): 1163-1173, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30637960

RESUMO

Scopolia tangutica is a traditional Chinese medicine used for antispasmodic, anesthesia, analgesia, and sedation. Its medicinal activity is associated to alkaloid constituents, including tropane and cinnamamide types. Low content of alkaloids in plant makes them difficult to be isolated and identified. The present work developed an effective method to quickly characterize alkaloids from Scopolia tangutica by high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. Thirteen reference compounds were studied for their fragmentation pathways, including five tropane alkaloids and eight cinnamamide ones. Alkaloid constituent was analyzed by an optimized high-performance liquid chromatography method and mass spectrometry analysis to achieve systematic characterization of alkaloids from Scopolia tangutica. As a result, 53 compounds were identified, including 21 tropane alkaloids (eight new ones), 18 caffeoyl ones (ten new ones) and 14 dicaffeoyl ones (seven new ones). It was important to provide rich information in phytochemical study and structure-guided isolation of important compounds from this plant.


Assuntos
Alcaloides/isolamento & purificação , Cinamatos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Scopolia/química , Tropanos/isolamento & purificação , Alcaloides/química , Cromatografia Líquida de Alta Pressão , Cinamatos/química , Medicamentos de Ervas Chinesas/química , Medicina Tradicional Chinesa , Extratos Vegetais/química , Espectrometria de Massas em Tandem , Fatores de Tempo , Tropanos/química
3.
Artigo em Inglês | MEDLINE | ID: mdl-30594825

RESUMO

Since the content of alkaloids is usually low in plants and they are easily co-eluted with other constituents, enrichment of alkaloids is essential in the discovery of bioactive lead compounds from natural products. In this paper, an easy SPE enrichment method was developed in a buffer-free solvent system based on electrostatic repulsion mechanism. The feasibility of the new method was verified by successful enrichment of alkaloids from Scopolia tangutica (S. tangutica) with an optimized eluting condition. Then this developed method was applied to other representative plants in different families, including Przewalskia tangutica and Peganum harmala L, Lycoris radiata and Menispermum dauricum DC, which enlarged the scope of applicability. Additionally, the new SPE procedure avoided possible structural change destruction caused by pH change. Simple solvent system, including formic acid (FA) and methanol, would benefit subsequent mass analysis, quantity determination and bioactivity screening, and so on.


Assuntos
Alcaloides/química , Alcaloides/isolamento & purificação , Extratos Vegetais/química , Alcaloides/análise , Cromatografia por Troca Iônica/métodos , Cromatografia de Fase Reversa/métodos , Scopolia/química , Eletricidade Estática
4.
Artigo em Inglês | MEDLINE | ID: mdl-29136553

RESUMO

Current Chinese Pharmacopoeia (ChP) standards apply liquid extraction combined with one dimensional liquid chromatography (1DLC) method for determining alkaloids in herbal medicines. The complex pretreatments lead to a low analytical efficiency and possible component loss. In this study, a heart cutting reversed phase - strong cation exchange two dimensional liquid chromatography (RP - SCX 2DLC) approach was optimized for simultaneously quantifying tropane alkaloids (anisodine, scopolamine and hyoscyamine) in herbal medicines and herbal medicine tablets without further treatment of the filtered extract. The chromatographic conditions were systematically optimized in terms of column type, mobile phase composition and flow rate. To improve peak capacity and obtain symmetric peak shape of alkaloids, a polar group embedded C18 column combined with chaotropic salts was used in the first dimension. To remove the disturbance of non-alkaloids, achieve unique selectivity and acquire symmetric peak shape of alkaloids, an SCX column combined with phosphate buffer was used in the second dimension. Method validation was performed in terms of linearity, precision (0.54-0.82%), recovery (94.1-105.2%), limit of detection (LOD) and limit of quantification (LOQ) of the three analytes varied between 0.067-0.115mgL-1 and 0.195-0.268mgL-1, respectively. The method demonstrated superiority over 1DLC method in respect of resolution (less alkaloid co-eluted), sample preparation (no pretreatment procedure) and transfer rate (minimum component loss). The optimized RP - SCX 2DLC approach was subsequently applied to quantify target alkaloids in five herbal medicines and herbal medicine tablets from three different manufactures. The results demonstrated that the developed heart cutting RP - SCX 2DLC approach represented a new, strategically significant methodology for the quality evaluation of tropane alkaloid in related herbal medicines that involve complex chemical matrix.


Assuntos
Alcaloides/análise , Cromatografia por Troca Iônica/métodos , Cromatografia de Fase Reversa/métodos , Tropanos/análise , Alcaloides/isolamento & purificação , Cátions , Limite de Detecção , Modelos Lineares , Extratos Vegetais/química , Reprodutibilidade dos Testes , Scopolia/química , Tropanos/isolamento & purificação
5.
Sci Rep ; 7: 46067, 2017 04 07.
Artigo em Inglês | MEDLINE | ID: mdl-28387362

RESUMO

Scopolia tangutica (S. tangutica) is a traditional Chinese medicinal plant used for antispasmodics, anesthesia, analgesia and sedation. Its pharmacological activities are mostly associated with the antagonistic activity at muscarinic acetylcholine receptors (mAchRs) of several known alkaloids such as atropine and scopolamine. With our recent identification of four hydroxycinnamic acid amides from S. tangutica, we hypothesized that this plant may contain previously unidentified alkaloids that may also contribute to its in vivo effect. Herein, we used a bioassay-guided multi-dimension separation strategy to discover novel mAchR antagonists from S. tangutica. The core of this approach is to use label-free cell phenotypic assay to first identify active fractions, and then to guide purification of active ligands. Besides four tropanes and six cinnamic acid amides that have been previously isolated from S. tangutica, we recently identified two new tropanes, one new cinnamic acid amide, and nine other compounds. Six tropane compounds purified from S. tangutica for the first time were confirmed to be competitive antagonists of muscarinic receptor 3 (M3), including the two new ones 8 and 12 with IC50 values of 1.97 µM and 4.47 µM, respectively. Furthermore, the cinnamic acid amide 17 displayed 15-fold selectivity for M1 over M3 receptors. These findings will be useful in designing lead compounds for mAchRs and elucidating mechanisms of action of S. tangutica.


Assuntos
Antagonistas Colinérgicos/farmacologia , Descoberta de Drogas , Antagonistas Muscarínicos/farmacologia , Scopolia/química , Células A549 , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Amidas/farmacologia , Animais , Células CHO , Antagonistas Colinérgicos/química , Cricetinae , Cricetulus , Células HT29 , Humanos , Antagonistas Muscarínicos/química , Fenótipo , Receptor Muscarínico M3/antagonistas & inibidores , Receptor Muscarínico M3/metabolismo
6.
Fitoterapia ; 108: 9-12, 2016 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-26586621

RESUMO

Scopolia tangutica Maxim (S. tangutica) extracts have been traditionally used as antispasmodic, sedative, and analgesic agents in Tibet and in the Qinghai province of China. Their active compositions are however poorly understood. We have recently isolated five new hydroxycinnamic acid (HCA) amides along with two known HCA amides, one cinnamic acid amide from these extracts. In this study, we evaluate their abilities to inhibit carbacol-induced activity of M1 muscarinic acetylcholine receptor along with the crude extracts. Chinese hamster ovary cells stably expressing the recombinant human M1 receptor (CHO-M1 cells) were employed to evaluate the anticholinergic potentials. Intracellular Ca(2+) changes were monitored using the FLIPR system. Five HCA amides as well as the crude S. tangutica extract displayed dose-dependent inhibitory effects against M1 receptor. These findings demonstrate that HCA amides are part of the M1 receptor-inhibiting principles of S. tangutica. Since blockade of parasympathetic nerve impulse transmission through the inhibition of the M1 receptor lessens smooth muscle spasms, our findings provided a molecular explanation for the traditional use of S. tangutica against spasm.


Assuntos
Ácidos Cumáricos/farmacologia , Antagonistas Muscarínicos/farmacologia , Extratos Vegetais/química , Receptor Muscarínico M1/antagonistas & inibidores , Scopolia/química , Animais , Células CHO , Cricetulus , Medicamentos de Ervas Chinesas/química , Humanos , Estrutura Molecular , Raízes de Plantas/química , Proteínas Recombinantes
7.
Planta Med ; 80(13): 1124-30, 2014 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-25127021

RESUMO

Four new hydroxycinnamic acid amides, scotanamines A-D (1-4), and seven known alkaloids, including N (1),N (10)-di-dihydrocaffeoylspermidine (5), scopolamine (6), anisodamine (7), hyoscyamine (8), anisodine (9), caffeoylputrescine (10), and N (1)-caffeoyl-N (3)-dihydrocaffeoylspermidine (11), were obtained from the roots of Scopolia tangutica. The present study represents the first recognition of hydroxycinnamic acid amides containing putrescine or spermidine in S. tangutica. Compound 1, in particular, contains a moiety resulting from the condensation of nortropinone and putrescine. Compound 2 exhibited moderate agonist activity at the µ-opioid receptor (EC50=7.3 µM). Compound 2 was tested in vivo and induced analgesia in mice. The analgesic effect was recorded using the tail-flick assay and was reversed by naloxone.


Assuntos
Alcaloides/farmacologia , Analgésicos/farmacologia , Scopolia/química , Alcaloides/química , Alcaloides/isolamento & purificação , Analgésicos/química , Analgésicos/isolamento & purificação , Animais , Células Cultivadas , Masculino , Camundongos , Extratos Vegetais/química , Raízes de Plantas/química , Receptores Opioides mu/química
8.
Analyst ; 137(6): 1451-7, 2012 Mar 21.
Artigo em Inglês | MEDLINE | ID: mdl-22299130

RESUMO

A non-aqueous solid phase extraction (SPE) method utilizing silica based strong cation exchange (SCX) was developed and optimized for the enrichment of alkaloids. In this method, silica based SCX SPE columns were used for the elimination of non-alkaloid compounds and the preconcentration of alkaloids from the extracts. Mass spectrometry was employed to analyze the alkaloid-enriched fraction, and results showed that the SPE method developed in this study was effective for the removal of non-alkaloids. Then, this pretreatment method was combined with high performance liquid chromatography for the quantification of scopolamine and hyoscyamine from Scopolia tangutica Maxim. The recoveries of scopolamine and (-)-hyoscyamine were 98.51% and 91.12%, respectively. Relative standard deviation values were 1.4% for scopolamine and 1.6% for (-)-hyoscyamine. The linearity was good in the 0.01-0.8 mg mL(-1) range for hyoscyamine and 0.01-0.4 mg mL(-1) range for scopolamine.


Assuntos
Alcaloides/química , Atropina/análise , Escopolamina/análise , Extração em Fase Sólida/métodos , Cromatografia Líquida de Alta Pressão/métodos , Espectrometria de Massas/métodos , Extratos Vegetais/química , Scopolia/química , Extração em Fase Sólida/instrumentação
9.
J Nat Med ; 65(2): 395-9, 2011 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-21076881

RESUMO

A rapid method that does not require a complicated preparation was developed for determining by HPLC the content of atropine (At) and scopolamine (Sc) in a sample of scopolia extract powder. The sample solution for HPLC was extracted using 0.1 mol/L HCl/methanol (8:2). At and Sc were separated using a pentafluorophenylpropyl column and detected at a wavelength of 210 nm. Acetonitrile-10 mmol/L ammonium acetate adjusted to pH 5.0 (8:2, v/v) was used as the mobile phase. The linearity was good in the 5.0-500 µg/mL range for At and 0.5-500 µg/mL range for Sc. The specificity for both At and Sc was satisfactory. The quantitation limits were 5.0 µg/mL for At and 0.5 µg/mL for Sc. The quantitative values of total alkaloid calculated using this method were higher (1.3-3.7%) than those obtained using the Japanese Pharmacopoeia Fifteenth Edition (JP15) method. The precision of this method, measured as the standard deviation, was found to be satisfactory and comparable to that of the JP15 method, determined by an analysis of 3 commercial scopolia extract powder samples.


Assuntos
Atropina/química , Cromatografia Líquida de Alta Pressão/métodos , Extratos Vegetais/química , Escopolamina/química , Scopolia/química , Reprodutibilidade dos Testes
10.
Acta Pol Pharm ; 64(3): 241-6, 2007.
Artigo em Inglês | MEDLINE | ID: mdl-17695147

RESUMO

The qualitative and quantitative determinations of coumarins, phenolic acids and flavonoids in the leaves and underground parts of Scopolia caucasica using paper chromatography and HPLC methods were described. From the leaves of this plant, kaempferol 3-O-(2-glucosyl)-galactoside-7-O-glucoside, kaempferol 3-O-(2-glucosyl)-galactoside and quercetin 3-O-glucoside were isolated and identified by spectroscopic methods (UV, 1H- and 13C-NMR).


Assuntos
Cumarínicos/isolamento & purificação , Flavonoides/isolamento & purificação , Fenóis/isolamento & purificação , Extratos Vegetais/química , Scopolia/química , Cromatografia Líquida de Alta Pressão , Cromatografia em Papel , Flavonoides/química , Fenóis/química , Folhas de Planta/química , Raízes de Plantas/química , Polifenóis
11.
J Pharm Biomed Anal ; 37(2): 231-7, 2005 Feb 23.
Artigo em Inglês | MEDLINE | ID: mdl-15708662

RESUMO

A uniformly sized molecularly imprinted polymer (MIP) for atropine has been prepared. The MIP was prepared using 2-(trifluoromethyl) acrylic acid and ethylene glycol dimethacrylate as a functional monomer and cross-linker, respectively, by a multi-step swelling and thermal polymerization method. The selectivity factor, which is defined as the ratio of the retention factors (k) on the molecularly imprinted and non-imprinted polymers, k(imprinted)/k(non-imprinted), was 2.2 for atropine on the MIP. The obtained MIP was applied for the determination of tropane alkaloids (atropine and scopolamine) in a commercial gastrointestinal drug by a column-switching HPLC system, consisting of an MIP material as a pre-column, and a conventional cation-exchange analytical column. An interference peak was observed at the retention time of atropine derived from pre-column. However, since the peak area was less than 0.5% the peak area of atropine of a standard solution under the analytical conditions of this study (0.2 microg of atropine was loaded), this interference was negligible in the determination of atropine. On the other hand, no interference peak was observed at the retention time of scopolamine. Calibration curves of atropine and scopolamine showed good linearity in the range of 0.02-0.9 microg/ml (r=0.9999) and 0.003-0.09 microg/ml (r=0.9998), respectively. The mean recoveries of atropine and scopolamine from a placebo pharmaceutical preparation sample were 98.9 and 99.9%, respectively. The intra-day precision (measured by relative standard deviation, R.S.D. (%)) of both ingredients was less than 2.0%. The optimized column-switching system was applied successfully to the determination of atropine and scopolamine in a commercial gastrointestinal drug.


Assuntos
Atropina/isolamento & purificação , Fármacos Gastrointestinais/química , Polímeros/química , Escopolamina/isolamento & purificação , Scopolia/química , Acrilatos/química , Calibragem , Cromatografia Líquida de Alta Pressão/instrumentação , Cromatografia Líquida de Alta Pressão/métodos , Reagentes de Ligações Cruzadas/química , Metacrilatos/química , Extratos Vegetais/química , Padrões de Referência , Sensibilidade e Especificidade
13.
Acta Pol Pharm ; 59(4): 275-80, 2002.
Artigo em Inglês | MEDLINE | ID: mdl-12403302

RESUMO

Kaempferol 3-O-(2-glucosyl)-galactoside-7-O-glucoside was isolated from the leaves of Scopolia carniolica Jacq. and S. sinensis Hemsl. From the latter taxon as well as kaempferol 3-O-galactoside and 3-O-(2-glucosyl)-galactoside, kaempferol and quercetin 3-O-robinobiosides and quercetin 3-O-sophoroside have been obtained. Moreover, from the leaves of S lurida Dun. kaempferol and quercetin 3-O-glucosides and 3-O-rutinosides were isolated. The structures of compounds have been determined by means of chemical and spectral methods (UV, LSI MS, 1H and 13C NMR, 1H-1H COSY NMR).


Assuntos
Flavonoides/análise , Scopolia , Flavonoides/química , Flavonoides/isolamento & purificação , Extratos Vegetais/análise , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Scopolia/química , Sementes/química
14.
Vet Hum Toxicol ; 44(4): 222-3, 2002 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-12136971

RESUMO

Scopolia extract (SE) contains hyoscyamine and scopolamine, which are both anticholinergic. It is usually used as a patent medicine to treat gastrointestinal disorders, to relieve spasmotic discomfort, or to decrease the secretion of gastric acid. Poisoning by SE presents similar symptoms and signs as other types of anticholinergic poisoning. We report a case of severe anticholinergic poisoning after accidentally drinking 8 ml of SE. The patient presented with acute delirium and was successfully treated with physostigmine.


Assuntos
Antagonistas Colinérgicos/intoxicação , Delírio/induzido quimicamente , Extratos Vegetais/intoxicação , Scopolia/química , Administração Oral , Antagonistas Colinérgicos/administração & dosagem , Inibidores da Colinesterase/uso terapêutico , Overdose de Drogas , Humanos , Masculino , Pessoa de Meia-Idade , Fisostigmina/uso terapêutico , Extratos Vegetais/administração & dosagem
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