Polyhydroxylated eudesmane sesquiterpenoids and sesquiterpenoid glucoside from the flower buds of Tussilago farfara / 中国天然药物

Chemical fractionation of the n-BuOH partition, which was generated from the EtOH extract of the flower buds of Tussilago farfara, afforded a series of polar constituents including four new sesquiterpenoids (1-4), one new sesquiterpenoid glucoside (5) and one known analogue (6) of the eudesmane type, as well as five known quinic acid derivatives (7-11). Structures of the new compounds were unambiguously characterized by detailed spectroscopic analyses, with their absolute configurations being established by X-ray crystallography, electronic circular dichroism (ECD) calculation and induced ECD experiments. The inhibitory effect of all the isolates against LPS-induced NO production in murine RAW264.7 macrophages was evaluated, with isochlorogenic acid A (7) showing significant inhibitory activity.

Tussilagone suppressed the production and gene expression of MUC5AC mucin via regulating nuclear factor-kappa B signaling pathway in airway epithelial cells

In the present study, we investigated whether tussilagone, a natural product derived from Tussilago farfara, significantly affects the production and gene expression of airway MUC5AC mucin. Confluent NCI-H292 cells were pretreated with tussilagone for 30 min and then stimulated with EGF (epidermal growth factor) or PMA (phorbol 12-myristate 13-acetate) for 24 h or the indicated periods. The MUC5AC mucin gene expression was measured by RT-PCR. Production of MUC5AC mucin protein was measured by ELISA. To elucidate the action mechanism of tussilagone, effect of tussilagone on PMA-induced NF-κB signaling pathway was investigated by western blot analysis. Tussilagone significantly inhibited the production of MUC5AC mucin protein and down-regulated the expression of MUC5AC mucin gene, induced by EGF or PMA. Tussilagone inhibited PMA-induced activation (phosphorylation) of inhibitory kappa B kinase (IKK), and thus phosphorylation and degradation of inhibitory kappa Ba (IκBα). Tussilagone inhibited PMA-induced phosphorylation and nuclear translocation of nuclear factor kappa B (NF-κB) p65. This, in turn, led to the down-regulation of MUC5AC protein production in NCI-H292 cells. These results suggest that tussilagone can regulate the production and gene expression of mucin by acting on airway epithelial cells through regulation of NF-κB signaling pathway.

Chemical comparison of different Farfarae Flos by NMR-based metabolomic approaches / 药学学报

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-3β, 16α-diol, chlorogenic acid, rutin, 7-(3'-ethylcrotonoyloxy)-1α-(2'-methyl-butyryloxy)-3, 14-dehydro-Z-notonipetranone (EMDNT), tussilagone, β-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.

Monitoring of chemical components with different color traits of Tussilago farfara using NMR-based metabolomics / 药学学报

The quality and grade of traditional Chinese medicinal herbs were assessed by their characteristics traditionally. According to traditional experience, the quality of the purple Flos Farfarae is better than that of yellow buds. NMR-based metabolomic approach combined with significant analysis of microarray (SAM) and Spearman rank correlation analysis were used to investigate the different metabolites of the Flos Farfarae with different color feature. Principal component analysis (PCA) showed clear distinction between the purple and yellow flower buds of Tussilago farfara. The S-plot of orthogonal PLS-DA (OPLS-DA) and t test revealed that the levels of threonine, proline, phosphatidylcholine, creatinine, 4, 5-dicaffeoylquinic acid, rutin, caffeic acid, kaempferol analogues, and tussilagone were higher in the purple flower buds than that in the yellow buds, in agreement with the results of SAM and Spearman rank correlation analysis. The results confirmed the traditional medication experience that "purple flower bud is better than the yellow ones", and provide a scientific basis for assessing the quality of Flos Farfarae by the color features.

Metabolomic study of flower buds of Tussilago farfara in different development stages by GC-MS / 中国中药杂志

<p><b>OBJECTIVE</b>Plant metabolomics combined with GC-MS was used to investigate metabolic fingerprinting of Tussilago farfara at different growth stages.</p><p><b>METHOD</b>Dried Samples were extracted by two-phase solvent system to obtain polar and nonpolar parts, which were subjected to GC-MS analysis. Metabolites were identified by NIST data base search and comparison with the authentic standards. The data were introduced into SIMCA-P 11.0 software package for multivariate analysis after pretreatment.</p><p><b>RESULT</b>Fifty-four metabolites were identified, including 35 polar metabolites and 19 nonpolar compounds. The score plot for PCA showed clear separation of the different development stages of flower buds of T. farfara, showing a trend of gradual change. Samples of October, November, December were in close proximity on the plot, indicating that the metabolome of these three periods was similar, samples from September (early development) and March (after flowering) were far away, showing big chemical differences. Content comparison results of some representative metabolites reveals that, the content of proline, lysine and linoleic acid increased gradually to the highest in the medium term, but sharply decreased to the lowest after flowering; the content of malic acid and citric acid were the lowest in the medium term; sucrose content decreased gradually, and then reached the lowest level after blooming.</p><p><b>CONCLUSION</b>It is obvious that metabolites of the early development and flowering stage were quite different with those of the traditional harvest time, suggesting that they can not be used as traditional medicine. This study will provide a research basis for harvest time determination and bioactive compounds of T. farfara.</p>

Flavonoids and phenolic acid derivatives from flos farfarae / 中国中药杂志

<p><b>OBJECTIVE</b>To investigate the chemical constituents of the flower buds of Tussilago farfara.</p><p><b>METHOD</b>The chemical constituents were isolated by silica gel and Sephadex LH-20 column chromatography, and structurally elucidated by spectral evidence together with physiochemical properties.</p><p><b>RESULT</b>Seven flavonoids, quercetin (1), quercetin-3-O-beta-D-glucopyranoside (2), quercetin-4'-O-beta-D-glucopyranoside (3), hyperoside (4), rutin (5), kaempferol (6), kaempferol-3-O-alpha-L-rhamnopyranosyl-(1-6)-beta-D-glucopyranoside (7), together with eight phenolic acid derivatives, caffeic acid (8), methyl caffeate (9), ethyl caffeate (10), (E)-2,5-dihydroxycinnamic acid (11), 3,4-di-O-caffeoylquinic acid (12), 4,5-di-O-caffeoylquinic acid (13), methyl4,5-di-O-caffeoylquinate (14) and chlorogenic acid (15) were isolated from the flower buds of Tussilago farfara.</p><p><b>CONCLUSION</b>Compounds 7, 9-14 are isolated from this plant, also from this genus, for the first time.</p>

Simultaneous determination of rutin, isoquercitrin and chlorogenic acid in Farfarae Flos by HPLC / 中国中药杂志

<p><b>OBJECTIVE</b>To develop an HPLC method for simultaneous determination of rutin, isoquercitrin and chlorogenic acid in Farfarae Flos.</p><p><b>METHOD</b>The analysis was carried out on a Phenomenex Synergi POLAR-RP 80A column (4.6 mm x 250 mm, 4 microm) with gradient elution using methanol-acetonitrile-water (adjusted to pH 2.5 with formic acid) as mobile phase. The flow rate was 1.2 mL x min(-1) and the detection wavelength was at 255 nm.</p><p><b>RESULT</b>The calibration curves were linear over the range of 0.2-2 000 microg x L(-1) for rutin and isoquercitrin, 10-2 000 microg x L(-1) for chlorogenic acid, respectively. The average recoveries were 99.5% for rutin, 100.1% for isoquercitrin and 99.4% for chlorogenic acid, respectively, with RSD not more than 3.0%.</p><p><b>CONCLUSION</b>The described method is reliable and could be used for the quality control of Farfarae Flos.</p>

HPLC fingerprint of chemical constituents of Flos Farfarae / 药学学报

This paper is aimed to establish the method of fingerprint analysis of chemical constituents by reversed-phase high-performance liquid chromatographic (HPLC) with diode array detector (DAD) for the quality control of the flower buds of Tussilago farfara L. (Flos Farfarae). The method was performed on a Dikma Diamonsil C18 column (250 mm x 4.6 mm ID, 5 gim) with a mixed mobile phase of 0.03% trifluoroacetic acid solution and acetonitrile in a gradient mode. The flow rate was 1.0 mL x min(-1) and the wavelength of measurement was 240 nm. Ten batches of the Flos Farfarae were determined. The HPLC chromatographic fingerprint of chemical constituents was established from the 10 batches of the Flos Farfarae and showed 25 characteristic common peaks, among which 16 peaks were recognized and 18 compounds (adenosine, uridine, gallic acid, 3-O-caffeoylquinic acid, p-hydroxybenzoic acid, trans-caffeic acid, phthalic acid, rutin, hyperoside, 3,5-O-dicaffeoylquinic acid, kaempferol-3-O-beta-D-glucopyranoside, isoferulic acid, ferulic acid, quercetin, 2,2-dimethyl-6-acetyl chromanone, dibutylphthalate, tussilagone, 7beta-(3'-ethylcrotonoyloxy)-1alpha-(2'-methyl-butyryloxy)-3,14-dehydro-E-notonipetranone) were determined by comparison with chromatographic behaviors and UV spectra of the authentic compounds. The 10 batches of samples were classified as 2 clusters by cluster analysis and 6 samples were confirmed to establish the mutual model. The samples' quality was assessed by Similarity Evaluation System for Chromatographic Fingerprint of TCM (2004 B version). The convenient and high specific method can be used to identify and evaluate the quality of the Flos Farfarae.

Studies on chemical constituents in the buds of Tussilago farfara / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents in the buds of Tussilago farfara.</p><p><b>METHOD</b>The chemical constituents were isolated by various column chromatographic methods and structurally elucidated by NMR and MS evidences.</p><p><b>RESULT</b>Eleven compounds were obtained and identified as methyl 3, 4-O-dicaffeoylquinate (1), methyl 3, 5-O-dicaffeoylquinate (2), methyl 4, 5-O-dicaffeoylquinate (3), 3, 5-O-dicaffeoylquinic acid (4), methyl 3-O-caffeoylquinate (5), 3-O-caffeoylquinic acid (6), hyperoside (7), rutin (8), kaempferol 3-O-beta-D-glucopyranoside (9), quercetin (10), and kaempferol (11).</p><p><b>CONCLUSION</b>Compounds 2-5 were isolated from the genus for the first time.</p>

Phytochemical and pharmacological research progress in Tussilago farfara / 中国中药杂志

Tussilago farfara contained the chemical constitutents including terpenes, flavonoids, and alkanoids. It has been used for the relief of coughs and as an expectorant, blood pressure raiser, platelet activating factor inhibitor and anti-inflammatory agents. This paper reviewed the phytochemical and pharmacological research progress in T. farfara, including the chemical ingredients, the pharmaceutical activities and the security evaluation aiming at its toxicity. The problems at present and the reseach direction for the future on T. farfara have been put forward.