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1.
J Chromatogr A ; 1602: 188-198, 2019 Sep 27.
Artigo em Inglês | MEDLINE | ID: mdl-31147156

RESUMO

A liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS)-based dereplicative method was developed for identifying oplopane- and bisabolane-type sesquiterpenoids from buds of Tussilago farfara L. The analysis of these chemical analogues, sesquiterpene esters, is challenging by MS-based nontargeted metabolomic approaches because of their in-source fragmentation and structural diversity. To profile these sesquiterpenoids, four diagnostic ions (m/z 215.143, 217.158, 229.123, and 231.138) were suggested in the positive ion mode and the developed method utilized two sequential MS/MS scan modes to identify common skeletons and investigate the fragmentation patterns of their parent molecules. Precursor ion scan by triple quadrupole MS/MS provided the parent molecular ions from their diagnostic ions, and product ion scan by quadrupole time-of-flight MS/MS confirmed their fragmentation behaviors. Under the optimized UHPLC-MS/MS method, 74 sesquiterpenoids were characterized from the Farfarae Flos and 11 compounds were isolated for the method validation. Among those compounds, three sesquiterpenoids were newly separated from the Farfarae Flos. Furthermore, the diagnostic ions and the MS/MS fragment behaviors were applied to the accurate quantification of the 8 isolated sesquiterpenoids. Therefore, the developed LC-MS/MS-based method highlighted the chemical composition of the Farfarae Flos and could be extended to the screening and quantification of other sesquiterpene esters.


Assuntos
Técnicas de Química Analítica/métodos , Espectrometria de Massas , Sesquiterpenos/química , Tussilago/química , Cromatografia Líquida , Íons/química , Sesquiterpenos/isolamento & purificação
2.
Molecules ; 24(3)2019 Feb 08.
Artigo em Inglês | MEDLINE | ID: mdl-30743985

RESUMO

The purpose of this study was to establish a rapid, reliable, and sensitive ultra-performance liquid chromatography with triple-quadrupole tandem mass spectrometry coupled with chemometric method to measure and evaluate the differences between thirteen compounds in raw and processed Tussilago farfara L. from different sources. This assay method was validated, and the results indicated that the calibration curves for the thirteen compounds had good linearity (R² > 0.9990). The limits of detection and limits of quantification of the thirteen compounds ranged from 0.0012 to 0.0095 µg/mL and from 0.0038 to 0.0316 µg/mL, respectively. The relative standard deviations (RSD) of the intra- and inter-day precisions and stability ranged from 1.06 to 2.00%, 0.26 to 1.99%, and 0.75 to 1.97%, respectively. The sample recovery rates of the thirteen compounds with different concentrations were 94.47⁻104.06%. The chemometric results, including principal component analysis, hierarchical clustering analysis, three-dimensional analysis, and box plot analysis, indicated that there are significance differences in raw and processed Tussilago farfara L. The results of this study confirm that the proposed method is the first reported method that has been successfully applied for simultaneous determination and discovery of the difference between thirteen compounds of raw and processed Tussilago farfara L. Thus, this method could be a helpful tool for the detection and confirmation of the quality of traditional Chinese medicines and provide a basis for future pharmacological studies.


Assuntos
Cromatografia Líquida de Alta Pressão , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Espectrometria de Massas em Tandem , Tussilago/química , Extração Líquido-Líquido , Estrutura Molecular , Reprodutibilidade dos Testes , Sensibilidade e Especificidade
3.
Chem Biodivers ; 16(3): e1800581, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30600902

RESUMO

Fourteen chromane derivatives of seven pairs of enantiomers (1-14) have been obtained from the ethanolic extract of the flower buds of Tussilago farfara L. Their structures with absolute configurations have been elucidated by detailed spectroscopic analyses, chemical methods, and particularly comparison of experimental ECD spectra with theoretically computed ones. Biological evaluations revealed that they did not show cytoprotective, antimicrobial, and α-glucosidase inhibitory activities.


Assuntos
Cromanos/química , Flores/química , Extratos Vegetais/química , Raízes de Plantas/química , Tussilago/química , Cromanos/isolamento & purificação , Teoria da Densidade Funcional , Humanos , Conformação Molecular , Extratos Vegetais/isolamento & purificação , Estereoisomerismo , Células Tumorais Cultivadas
4.
Chem Biol Interact ; 294: 74-80, 2018 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-30142311

RESUMO

Inflammatory bowel disease (IBD) is a chronically relapsing inflammatory disorder of the gastrointestinal tract. Current IBD treatments are associated with poor tolerability and insufficient therapeutic efficacy, prompting the need for alternative therapeutic approaches. Recent advances suggest promising interventions based on a number of phytochemicals. Herein, we explored the beneficial effects of tussilagone, a major component of Tussilago farfara, in mice subjected to acute colitis induced by dextran sulfate sodium (DSS). Treatment with tussilagone resulted in a significant protective effect against DSS-induced acute colitis in mice via amelioration of weight loss, and attenuation of colonic inflammatory damage. Additionally, the expression of tumor necrosis factor-α and interleukin-6 and the activity of myeloperoxidase in colonic tissues were significantly reduced in tussilagone-treated mice. Furthermore, immunohistochemical analysis revealed that tussilagone treatment reduced the numbers of nuclear factor-kappa B (NF-κB) and increased the numbers of nuclear factor erythroid 2-related factor 2 (Nrf2) in nuclei of colonic tissues. Taken together, tussilagone treatment attenuated DSS-induced colitis in mice through inhibiting the activation of NF-κB and inducing Nrf2 pathways, indicating that tussilagone is a potent therapeutic candidate for treatment of intestinal inflammation.


Assuntos
Colite/prevenção & controle , Sesquiterpenos/uso terapêutico , Tussilago/química , Animais , Colite/induzido quimicamente , Colite/patologia , Colo/efeitos dos fármacos , Colo/metabolismo , Sulfato de Dextrana/toxicidade , Modelos Animais de Doenças , Heme Oxigenase-1/metabolismo , Interleucina-6/genética , Interleucina-6/metabolismo , Camundongos , Camundongos Endogâmicos BALB C , Fator 2 Relacionado a NF-E2/metabolismo , NF-kappa B/metabolismo , Óxido Nítrico Sintase Tipo II/genética , Óxido Nítrico Sintase Tipo II/metabolismo , Peroxidase/metabolismo , Sesquiterpenos/farmacologia , Fator de Necrose Tumoral alfa/genética , Fator de Necrose Tumoral alfa/metabolismo , Tussilago/metabolismo
5.
Redox Biol ; 18: 6-15, 2018 09.
Artigo em Inglês | MEDLINE | ID: mdl-29890337

RESUMO

Oxidative stress plays a key role in neurodegenerative diseases such as Alzheimer's and Parkinson's diseases. Therefore, the nuclear factor-E2-related factor 2 (Nrf2), a key regulator of the antioxidative response, is considered to be important as a therapeutic target for neurodegenerative diseases. We investigated the underlying mechanism of Nrf2-mediated neuroprotective effects against oxidative stress in the PC12 cell line by 7ß-(3-ethyl-cis-crotonoyloxy)-1α-(2-methylbutyryloxy)-3,14-dehydro-Z-notonipetranone (ECN), one of the sesquiterpenoids in Farfarae Flos. Pretreatment of PC12 cells with ECN had a protective effect against hydrogen peroxide (H2O2)- or 6-hydroxydopamine (6-OHDA)-induced cytotoxicity. ECN upregulated the ARE-luciferase activity and induced the mRNA expression of Nrf2 and antioxidant enzyme heme oxygenase-1 (HO-1). Knockdown of Nrf2 by small, interfering RNA (siRNA) abrogated the upregulation of HO-1, indicating that ECN had induced HO-1 via the Nrf2 pathway. Pretreatment with the thiol reducing agents, N-acetylcysteine (NAC) or dithiothreitol (DTT), attenuated Nrf2 activation and HO-1 expression. However, the non-thiol reducing antioxidant, Trolox, failed to inhibit HO-1 induction by ECN. These results suggest that ECN may directly interact with Kelch-like ECH-associated protein 1 (Keap1) and modify critical cysteine thiols present in the proteins responsible for Nrf2-mediated upregulation of HO-1. In a 6-OHDA-induced mouse model of PD, administration of ECN ameliorated motor impairments and dopaminergic neuronal damage. Taken together, ECN exerts neuroprotective effects by activating the Nrf2/HO-1 signaling pathway in both PC12 cells and mice. Thus, ECN, as an Nrf2 activator, could be an attractive therapeutic candidate for the neuroprotection or treatment of neurodegenerative diseases.


Assuntos
Fator 2 Relacionado a NF-E2/metabolismo , Neuroproteção/efeitos dos fármacos , Fármacos Neuroprotetores/farmacologia , Oxidopamina/efeitos adversos , Sesquiterpenos/farmacologia , Transdução de Sinais/efeitos dos fármacos , Tussilago/química , Animais , Peróxido de Hidrogênio/efeitos adversos , Masculino , Camundongos , Camundongos Endogâmicos ICR , Fármacos Neuroprotetores/química , Células PC12 , Ratos , Sesquiterpenos/química
6.
J Pharm Biomed Anal ; 156: 349-357, 2018 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-29753281

RESUMO

This study aimed to clarify the difference between the effective compounds of raw and processed Farfarae flos using a network pharmacology-integrated metabolomics strategy. First, metabolomics data were obtained by ultra high-performance liquid chromatography-quadrupole-time of flight mass spectrometry (UHPLC-Q-TOF/MS). Then, metabolomics analysis was developed to screen for the influential compounds that were different between raw and processed Farfarae flos. Finally, a network pharmacology approach was applied to verify the activity of the screened compounds. As a result, 4 compounds (chlorogenic acid, caffeic acid, rutin and isoquercitrin) were successfully screened, identified, quantified and verified as the most influential effective compounds. They may synergistically inhibit the p38, JNK and ERK-mediated pathways, which would induce the inhibition of the expression of the IFA virus. The results revealed that the proposed network pharmacology-integrated metabolomics strategy was a powerful tool for discovering the effective compounds that were responsible for the difference between raw and processed Chinese herbs.


Assuntos
Descoberta de Drogas/métodos , Medicamentos de Ervas Chinesas/análise , Vírus da Influenza A/efeitos dos fármacos , Influenza Humana/tratamento farmacológico , Tussilago/química , Ácidos Cafeicos/análise , Ácidos Cafeicos/farmacologia , Ácido Clorogênico/análise , Ácido Clorogênico/farmacologia , Cromatografia Líquida de Alta Pressão/métodos , Sinergismo Farmacológico , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Flores/química , Humanos , Vírus da Influenza A/fisiologia , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Metabolômica/métodos , Quercetina/análogos & derivados , Quercetina/análise , Quercetina/farmacologia , Rutina/análise , Rutina/farmacologia , Biologia de Sistemas/métodos , Espectrometria de Massas em Tandem/métodos
7.
Int J Biol Macromol ; 113: 849-858, 2018 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-29505876

RESUMO

In present study, we purified a polysaccharide, TFPB1, from the flower buds of Tussilago farfara using DEAE-cellulose 52 anion-exchange and Sephacryl S-300 HR gel filtration chromatography. TFPB1 was a homogeneous polysaccharide with a molecular weight of 37.8kDa and composed of rhamnose, galacturonic acid, glucose, galactose, and arabinose, in a ratio of 13:13:1:7:12. Methylation and NMR results demonstrated that TFPB1 contained a rhamnogalacturonan I backbone consisting of a repeat disaccharide unit →4)-α-D-GalAp-(1→2)-α-L-Rhap-(1→, substituted by various type II arabinogalactan branches including terminal galactose, (1→3)-ß-D-galactan and (1→5)-α-L-arabinan, attached to the O-4 of (1→2)-α-L-Rhap. TFPB1 was found to inhibit cell proliferation of A549 cells and induce cell apoptosis in vitro. Furthermore, TFPB1 downregulated the phosphorylation of Akt, and upregulated caspase-3, Fas, FasL, and Bax expression, but downregulated Bcl-2 expression. Therefore, TFPB1 exhibited anti-proliferative and anti-apoptotic effect partly depending on the suppression of Akt signaling pathway. These findings provided us a potential chemotherapeutic strategy for the treatment of human non-small cell lung cancer.


Assuntos
Apoptose/efeitos dos fármacos , Carcinoma Pulmonar de Células não Pequenas/patologia , Flores/química , Neoplasias Pulmonares/patologia , Polissacarídeos/química , Polissacarídeos/farmacologia , Tussilago/química , Células A549 , Antineoplásicos/química , Antineoplásicos/farmacologia , Ciclo Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Humanos , Peso Molecular , Fosfatidilinositol 3-Quinases/metabolismo , Proteínas Proto-Oncogênicas c-akt/metabolismo , Transdução de Sinais/efeitos dos fármacos
8.
Food Chem Toxicol ; 108(Pt A): 120-127, 2017 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-28733231

RESUMO

Tussilagonone is a compound derived from the medicinal plant Tussilago farfara L., which is used as a traditional medicine for respiratory diseases, including asthma and pneumonia. Recent reports suggest that tussilagonone exhibits anti-inflammatory effects; however, the scope of protective functions has not been elucidated yet. In this study, we demonstrate that tussilagonone enhances cellular detoxification by increasing quinone reductase activity in Hepa1c1c7 cells. In addition, tussilagonone decreased tert-butyl hydroperoxide(t-BHP)-induced ROS production and cell death, suggesting that it also acts as a potent antioxidant. To verify the molecular mechanism underlying tussilagonone activity, we examined the expression of nuclear factor erythroid 2-related factor 2(Nrf2)-a transcription factor that regulates antioxidant protein expression-in HepG2 cells. Significantly, these results showed that tussilagonone induces Nrf2 activation and nuclear accumulation, resulting in the upregulation of the detoxifying enzymes NAD(P)H quinone dehydrogenase 1(NQO1) and heme oxygenase-1(HO-1) that protect cells from oxidative stress. Further molecular analyses revealed that tussilagonone-induced Nrf2 activation was mediated by ERK1/2 in HepG2 cells. Collectively, these data indicate that tussilagonone attenuates t-BHP-induced ROS and activates quinone reductase activity via Nrf2 pathway activation and target gene expression, and thereby acts as an antioxidant that protects HepG2 cells from oxidative stress and associated damage.


Assuntos
Regulação da Expressão Gênica/efeitos dos fármacos , Fator 2 Relacionado a NF-E2/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Ácidos Pentanoicos/farmacologia , Sesquiterpenos/farmacologia , Tussilago/química , Elementos de Resposta Antioxidante , Antioxidantes/metabolismo , Sobrevivência Celular , Células Hep G2 , Humanos , Fator 2 Relacionado a NF-E2/genética , Ácidos Pentanoicos/química , Interferência de RNA , RNA Interferente Pequeno , Espécies Reativas de Oxigênio , Sesquiterpenos/química , Regulação para Cima
9.
J Chromatogr A ; 1489: 107-114, 2017 Mar 17.
Artigo em Inglês | MEDLINE | ID: mdl-28215402

RESUMO

A novel application of counter-current chromatography (CCC) to enrich plant extracts using direct and continuous injection (CCC-DCI) was developed to fractionate sesquiterpenoids from the buds of Tussilago farfara L. In this study, an n-hexane-acetonitrile-water (HAcW) solvent system was separately pumped into the CCC column, and an extraction solution (45% acetonitrile) was directly and continuously injected into the CCC column. Since the extraction solution was used as a mobile phase in this method, solvent consumption could be greatly reduced. To enrich the extraction solution (315.9g/5.4L), only 4.2L water, 4.6L acetonitrile, and 1.2L n-hexane were used, including the extraction step. Finally, 6.8g of a sesquiterpenoid-enriched (STE) fraction was obtained from the crude extract (315.9g) of Tussilago farfara (1kg) in a single CCC run with a separation time of 8.5h. The sample injection capacity of CCC-DCI was greater than 300g; this amount of sample could not be handled in conventional CCC or other fractionation methods with the same column volume. Moreover, three major sesquiterpenoids (1: tussilagone, 2: 14-acetoxy-7ß-(3'-ethyl cis-crotonoyloxy)-1α-(2'-methylburyryloxy)-notonipetranone, and 3: 7ß-(3'-ethyl cis-crotonoyloxy)-1α-(2'-methylburyryloxy)-3, 14-dehydro-Z-notonipetranone) were purified from the STE fraction by CCC, and their chemical structures were elucidated by 1H NMR and 13C NMR. A quantification study was conducted, and the contents of compounds 1-3 in the CCC-DCI fraction were higher than those of conventional multi-step fractionations performed in series: solvent partitioning and open column chromatography. Furthermore, the average CCC-DCI recoveries were 96.1% (1), 96.9% (2), and 94.6% (3), whereas the open column chromatography recoveries were 77.7% (1), 66.5% (2), and 58.4% (3). The developed method demonstrates that CCC is a useful technique for enriching target components from natural products.


Assuntos
Distribuição Contracorrente/métodos , Sesquiterpenos/isolamento & purificação , Tussilago/química , Acetonitrilos/química , Hexanos/química , Extratos Vegetais/química , Solventes/química , Água/química
10.
J Sep Sci ; 39(21): 4243-4250, 2016 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-27673325

RESUMO

Pyrrolizidine alkaloids are the toxic components in Tussilago farfara L. Due to the lack of standard substances for quantitative analysis and traces of pyrrolizidine alkaloids in total alkaloids, the full quality control of Tussilago farfara L has been limited. In this study, we aimed to solve the difficulty of determination of pyrrolizidine alkaloids and identify more components in the total alkaloids. An on-line preconcentration method has been applied to improve determining sensitivity of pyrrolizidine alkaloids in Tussilago farfara L. in which included field-amplified sample stacking and sweeping in micellar electrokinetic capillary chromatography. The main parameters that affected separation and stacking efficiency were investigated in details. Under the optimal conditions, the sensitivity enhancement factors obtained by the developed method for the analytes were from 15- to 12-fold, the limits of detection of senkirkine and senecionine were 2∼5 µg/L. Senkirkine and senecionine have been detected in alkaloids (c) of Tussilago farfara L, along ferulic acid methyl ester and methyl caffeate. The developed method was also applied to the analysis of acid extraction (a) of Tussilago farfara L, and senkirkine could be detected directly. The results indicated that the developed method is feasible for the analysis of pyrrolizidine alkaloids in Tussilago farfara L with good recoveries.


Assuntos
Cromatografia Capilar Eletrocinética Micelar , Alcaloides de Pirrolizidina/análise , Tussilago/química , Micelas
11.
Arch Pharm Res ; 39(4): 474-480, 2016 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-26983826

RESUMO

A new cytoprotective compound, 1-[(4S)-3,4-dihydro-4-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl]-ethanone (1) was isolated from the flower buds of Tussilago farfara L. (Compositae), together with eight known compounds, 3,4-dicaffeoyl isoquinic acid (2), trans-cinnamic acid (3), 4-hydroxyacetophenone (4), 4,5-dicaffeoylquinic acid methyl ester (5), 3,5-dicaffeoylquinic acid methyl ester (6), 4-hydroxybenzoic acid (7), isoquercetrin (8), and ligucyperonol (9). Compounds 2-4 were found in this plant for the first time. The isolates 1-9, were tested for their cytoprotective activities against glucose oxidase-induced oxidative stress in mouse fibroblast NIH3T3 cells and human keratinocyte HaCaT cells. Among them, 1 and 3 showed significant cytoprotective activities as determined by MTT assay and lactate dehydrogenase leakage, indicating their possibility as the potent cytoprotective agents. The structure of 1 was determined by spectroscopic data analysis including 1D- and 2D-NMR experiments, and its absolute configuration was elucidated by a circular dichroism.


Assuntos
Benzopiranos/isolamento & purificação , Benzopiranos/farmacologia , Citoproteção/efeitos dos fármacos , Flores/química , Glucose Oxidase/toxicidade , Queratinócitos/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Tussilago/química , Animais , Sobrevivência Celular/efeitos dos fármacos , Humanos , Queratinócitos/metabolismo , Camundongos , Estrutura Molecular , Células NIH 3T3
12.
Pharm Biol ; 54(7): 1117-24, 2016 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-26439905

RESUMO

CONTEXT: The flower bud of Tussilago farfara L. (Compositae) (FTF) is one of the traditional Chinese medicinal herbs used to treat cough, phlegm, bronchitic, and asthmatic conditions. OBJECTIVE: The objective of this study is to isolate four caffeoylquinic acids from the ethyl acetate extract (EtE) of FTF and to evaluate their antitussive, expectorant, and anti-inflammatory activities. MATERIALS AND METHODS: The structures of compounds 1-4 isolated from EtE were determined by spectral analysis. Mice were orally treated with these compounds and their mixture (in a ratio of 5:28:41:26 as in EtE) at doses of 10 and 20 mg/kg once daily for 3 d. The antitussive and expectorant activities were evaluated separately with the ammonia liquor-induced model and the phenol red secretion model. The anti-inflammation activity was evaluated using leukocyte count in the bronchoalveolar lavage fluid after ammonia liquor-induced acute airway inflammation. RESULTS: The four compounds were identified as chlorogenic acid (1), 3,5-dicaffeoylquinic acid (2), 3,4-dicaffeoylquinic acid (3), and 4,5-dicaffeoylquinic acid (4). All compounds, especially compound 4 (58.0% inhibition in cough frequency), showed a significant antitussive effect. However, the mixture was the most effective to inhibit the cough frequency by 61.7%. All compounds also showed a significant expectorant effect, while compound 2 was the most potent to enhance the phenol red secretion by 35.7%. All compounds significantly alleviated inflammation, but compound 4 showed the strongest effect to inhibit the leukocytosis by 49.7%. DISCUSSION AND CONCLUSION: The caffeoylquinic acids and their mixture, exhibiting significant antitussive, expectorant, and anti-inflammatory effects, could be considered as the main effective ingredients of FTF, and they may act in a collective and synergistic way.


Assuntos
Antitussígenos/farmacologia , Tosse/prevenção & controle , Expectorantes/farmacologia , Extratos Vegetais/farmacologia , Pneumonia/prevenção & controle , Ácido Quínico/análogos & derivados , Acetatos/química , Amônia , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antitussígenos/isolamento & purificação , Tosse/induzido quimicamente , Tosse/imunologia , Modelos Animais de Doenças , Expectorantes/isolamento & purificação , Flores , Leucocitose/induzido quimicamente , Leucocitose/prevenção & controle , Camundongos Endogâmicos ICR , Fenolsulfonaftaleína , Fitoterapia , Extratos Vegetais/isolamento & purificação , Plantas Medicinais , Pneumonia/induzido quimicamente , Pneumonia/imunologia , Ácido Quínico/isolamento & purificação , Ácido Quínico/farmacologia , Solventes/química , Tussilago/química
13.
Yao Xue Xue Bao ; 50(5): 599-604, 2015 May.
Artigo em Chinês | MEDLINE | ID: mdl-26234144

RESUMO

1H NMR-based metabolomic approach combined with multivariate statistical analysis was used to evaluate the quality of 21 Farfarae Flos (FF) samples from different growth regions. Principal component analysis showed that wild and cultivated FF could be separated clearly, suggesting a big chemical difference existed between them. Supervised PLS-DA analysis indicated that the wild samples showed higher levels of secondary metabolites, such as bauer-7-ene-3ß, 16α-diol, chlorogenic acid, rutin, 7-(3'-ethylcrotonoyloxy)-1α-(2'-methyl-butyryloxy)-3, 14-dehydro-Z-notonipetranone (EMDNT), tussilagone, ß-sitosterol and sitosterone. This is consistent with traditional experience that the quality of wild samples are better than that of cultivated ones. The content of pyrrolizidine alkaloids senkirkine also differed greatly among samples from different habitats. The Pearson correlation analysis showed that senkirkine is positively correlated with 4, 5-O-dicaffeoylquinic acid, 3,5-O-dicaffeoylquinic acid, 3,4-O-dicaffeoylquinic acid, rutin, kampferol analogues, to a statistically significant extent. The correlation between the toxic compounds and the bioactive components in FF should be further studied.


Assuntos
Medicamentos de Ervas Chinesas/química , Flores/química , Metabolômica , Tussilago/química , Ácido Clorogênico , Imagem por Ressonância Magnética , Espectroscopia de Ressonância Magnética , Ácido Quínico/análogos & derivados , Rutina , Sitosteroides
14.
Chem Pharm Bull (Tokyo) ; 63(7): 546-53, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25971744

RESUMO

The flower bud of Tussilago farfara L., called Farfarae Flos, has traditionally been used in Oriental medicine for the treatment of bronchitis and asthma. To establish a standard for quality control as well as the reliable identification of Farfarae Flos, the contents of five standards, rutin (1), isoquercetin (2), 3,5-dicaffeoylquinic acid (3), tussilagone (4), and tussilagonone (5), were determined by quantitative high-performance liquid chromatography (HPLC)/photodiode array (PDA) analysis. The five standards were separated on a YoungJinBioChrom Aegispak C18-L (250-mm×4.6-mm, 5-µm) column by gradient elution using 0.03% trifluoroacetic acid in water (A), with acetonitrile (B) as the mobile phase. The flow rate was 1.0 mL/min, and the UV detector wavelength was set at 220 nm. The method was successfully used in the analysis of Farfarae Flos from different geographic origins with relatively simple conditions and procedures, and the results demonstrated satisfactory linearity, recovery, precision, accuracy, stability, and robustness. The HPLC analytical method for pattern recognition analysis was validated by repeated analysis of 62 Farfarae Flos samples. This result indicated that the established HPLC/PDA method is suitable for quantitation and pattern recognition analyses for the quality evaluation of Farfarae Flos.


Assuntos
Cromatografia Líquida de Alta Pressão , Extratos Vegetais/análise , Tussilago/química , Cromatografia Líquida de Alta Pressão/normas , Análise por Conglomerados , Flores/química , Flores/metabolismo , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Controle de Qualidade , Tussilago/metabolismo
15.
J Enzyme Inhib Med Chem ; 30(5): 852-6, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25291008

RESUMO

We have isolated four sesquiterpenoids from Tussilago farfara, a traditional herbal medicine in Korea and China, and investigated the protective effects on LPS-induced neuronal cell death. Four sesquiterpenoids inhibited the production of nitric oxide, prostaglandin E2 and tumor necrosis factor-α in LPS-treated BV-2 cells through the inhibition of NF-κB pathway. These sesquiterpenoids also inhibited reactive oxygen species (ROS) generation in LPS-treated BV-2 cells. Furthermore, they inhibited LPS-induced neuronal cell death in co-culture system through the inhibition of NF-κB pathway and scavenging of ROS. These results indicated that sesquiterpenoids from Tussilago farfara may have beneficial therapeutic potential for the treatment of neurodegenerative diseases through inhibition of microglial activation.


Assuntos
Flores/química , Neurônios/efeitos dos fármacos , Fármacos Neuroprotetores/farmacologia , Sesquiterpenos/farmacologia , Tussilago/química , Animais , Morte Celular/efeitos dos fármacos , Diferenciação Celular/efeitos dos fármacos , Células Cultivadas , Relação Dose-Resposta a Droga , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , NF-kappa B/antagonistas & inibidores , NF-kappa B/metabolismo , Neurônios/metabolismo , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Células PC12 , Ratos , Espécies Reativas de Oxigênio/antagonistas & inibidores , Espécies Reativas de Oxigênio/metabolismo , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade
16.
J Ethnopharmacol ; 155(1): 796-800, 2014 Aug 08.
Artigo em Inglês | MEDLINE | ID: mdl-24955560

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Arctium lappa and Tussilago farfara (Asteraceae) are two plant species used traditionally as antitubercular remedies. The aim of this study was (i) to screen Arctium lappa and Tussilago farfara extracts for activity against Mycobacterium tuberculosis and (ii) to isolate and identify the compound(s) responsible for this reputed anti-TB effect. MATERIALS AND METHODS: The activity of extracts and isolated compounds was determined against Mycobacterium tuberculosis H37Rv using a high throughput spot culture growth inhibition (HT-SPOTi) assay. RESULTS: The n-hexane extracts of both plants, the ethyl acetate extract of Tussilago farfara and the dichloromethane phase derived from the methanol extract of Arctium lappa displayed antitubercular activity (MIC 62.5 µg/mL). Further chemical investigation of Arctium lappa led to the isolation of n-nonacosane (1), taraxasterol acetate (2), taraxasterol (3), a (1:1) mixture of ß sitosterol/stigmasterol (4), isololiolide (5), melitensin (6), trans-caffeic acid (7), kaempferol (8), quercetin (9), kaempferol-3-O-glucoside (10). Compounds isolated from Tussilago farfara were identified as a (1:1) mixture of ß sitosterol/stigmasterol (4), trans-caffeic acid (7), kaempferol (8), quercetin (9), kaempferol-3-O-glucoside (10), loliolide (11), a (4:1) mixture of p-coumaric acid/4-hydroxybenzoic acid (12), p-coumaric acid (13). All compounds were identified following analyses of their physicochemical and spectroscopic data (MS, (1)H and (13)C-NMR) and by comparison with published data. This is the first report of the isolation of n-nonacosane (1), isololiolide (5), melitensin (6) and kaempferol-3-O-glucoside (10) from Arctium lappa, and of loliolide (11) from Tussilago farfara. Amongst the isolated compounds, the best activity was observed for p-coumaric acid (13) (MIC 31.3 µg/mL or 190.9 µM) alone and in mixture with 4-hydroxybenzoic acid (12) (MIC 62.5 µg/mL). CONCLUSIONS: The above results provide for the first time some scientific evidence to support, to some extent, the ethno-medicinal use of Arctium lappa and Tussilago farfara as traditional antitubercular remedies.


Assuntos
Antituberculosos/farmacologia , Arctium/química , Extratos Vegetais/farmacologia , Tussilago/química , Antituberculosos/isolamento & purificação , Etnofarmacologia , Espectroscopia de Ressonância Magnética/métodos , Espectrometria de Massas/métodos , Medicina Tradicional , Testes de Sensibilidade Microbiana , Mycobacterium tuberculosis/efeitos dos fármacos
17.
Oncol Rep ; 32(3): 1117-23, 2014 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-24969837

RESUMO

Induction of apoptosis through activation of the TRAIL pathway is considered to be a promising anticancer strategy due to its ability to selectively induce apoptosis in cancer cells. However, the ability of cancer cells to acquire TRAIL resistance has limited the clinical translation of this approach. We previously reported that the TOR signaling pathway regulator-like (TIPRL) protein contributes to the resistance to TRAIL-induced apoptosis by inhibiting the MKK7-c-Jun N-terminal kinase (JNK) pathway via MKK7­TIPRL interaction. In the present study, we identified Tussilago farfara L. (TF) as a novel TRAIL sensitizer among 500 natural products using an ELISA system that specifically detects the MKK7-TIPRL interaction, and we validated candidates by GST-pull down assay. Co-treatment of Huh7 cells with TF and TRAIL induced apoptosis via inhibition of the MKK7-TIPRL interaction and an increase in MKK7/JNK phosphorylation. This is the first report to describe TF as a novel TRAIL sensitizer, unveiling a potentially novel therapeutic strategy in cancer therapy.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Carcinoma Hepatocelular/metabolismo , Peptídeos e Proteínas de Sinalização Intracelular/metabolismo , Neoplasias Hepáticas/metabolismo , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Extratos Vegetais/farmacologia , Tussilago/química , Apoptose , Carcinoma Hepatocelular/tratamento farmacológico , Carcinoma Hepatocelular/patologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Células HEK293 , Humanos , Peptídeos e Proteínas de Sinalização Intracelular/genética , Neoplasias Hepáticas/tratamento farmacológico , Neoplasias Hepáticas/patologia
18.
Planta Med ; 80(8-9): 703-9, 2014 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-24963619

RESUMO

Tussilagone (TSL) and its allied sesquiterpenoids were considered as the main active principles of the flower buds of Tussilago farfara, which has been widely used in China as an antitussive herbal medicine. Six new bisabolane-type sesquiterpenoids, tussfararins A-F (1-6), along with 12 known sesquiterpenoids, were isolated from the flower buds of T. farfara. Structures of the new compounds were elucidated by extensive spectroscopic analysis. The biological analysis showed that compounds 1, 3, 6, and 7 inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells with IC50 values of 13.6-24.4 µM.


Assuntos
Antitussígenos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Lipopolissacarídeos/efeitos adversos , Óxido Nítrico/metabolismo , Sesquiterpenos/isolamento & purificação , Tussilago/química , Animais , Antitussígenos/química , Antitussígenos/farmacologia , Linhagem Celular Tumoral , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Flores/química , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Plantas Medicinais , Sesquiterpenos/química , Sesquiterpenos/farmacologia
19.
Pharmazie ; 69(4): 311-5, 2014 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-24791598

RESUMO

In this work, ultrasound technology was used for the extraction of total flavonoids from Tussilago farfara L. Response surface methodology (RSM), based on a Box-Behnken design (BBD), was used to optimize the effects of processing parameters on total flavonoids yields. The parameters were ultrasonic frequency (X1), extraction time (X2) and ratio of liquid to solid (X3). The statistical analysis indicated that the parameters of ultrasonic power and ratio of liquid to solid, and the square effects among them had significant effects on the yield of flavonoids from Tussilago farfara L. The interaction between ultrasonic power and extraction time, and ultrasonic power and ratio of liquid to solid also caused significant effects on the yields. The optimum extraction conditions were determined as follows: ultrasonic power 420 W, extraction time 30 min, ratio of liquid to solid 25 mL/g. Under these conditions, the experimental yield 6.59 +/- 0.061% agreed closely with the predicted yield (6.64%).


Assuntos
Flavonoides/química , Tussilago/química , Ultrassom/métodos , Algoritmos , Interpretação Estatística de Dados , Flavonoides/isolamento & purificação , Indicadores e Reagentes , Modelos Estatísticos , Extratos Vegetais/química , Análise de Regressão , Reprodutibilidade dos Testes
20.
J Pharm Biomed Anal ; 75: 158-64, 2013 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-23261808

RESUMO

This study aims to find metabolites responsible for antitussive and expectorant activities of Tussilago farfara L. by metabolomic approach. Different parts (roots, flower buds, and leaves) of the title plant were analyzed systematically. The in vivo study revealed that the leaves and flower buds had strong antitussive and expectorant effects. Then ¹H NMR spectrometry together with principal component analysis (PCA) and partial least squares discriminant (PLS-DA) analysis were used to investigate the compounds responsible for the bioactivities. PCA was used to find the differential metabolites, while PLS-DA confirmed a strong correlation between the observed effects and the metabolic profiles of the plant. The result revealed that chlorogenic acid, 3,5-dicaffeoylquinic acid, and rutin may be closely related with the antitussive and expectorant activities. The overall results of this study confirm the benefits of using metabolic profiling for screening active principles in medicinal plants.


Assuntos
Antitussígenos/análise , Descoberta de Drogas , Medicamentos de Ervas Chinesas/química , Expectorantes/análise , Tussilago/química , Animais , Antitussígenos/farmacologia , Antitussígenos/uso terapêutico , Ácido Clorogênico/análogos & derivados , Ácido Clorogênico/análise , Ácido Clorogênico/farmacologia , Ácido Clorogênico/uso terapêutico , Medicamentos de Ervas Chinesas/farmacologia , Medicamentos de Ervas Chinesas/uso terapêutico , Etnofarmacologia , Expectorantes/farmacologia , Expectorantes/uso terapêutico , Feminino , Flores/química , Flores/crescimento & desenvolvimento , Flores/metabolismo , Espectroscopia de Ressonância Magnética , Masculino , Metabolômica/métodos , Camundongos , Camundongos Endogâmicos ICR , Folhas de Planta/química , Folhas de Planta/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Distribuição Aleatória , Rutina/análise , Rutina/farmacologia , Rutina/uso terapêutico , Estatística como Assunto , Tussilago/crescimento & desenvolvimento , Tussilago/metabolismo
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