• Archives of Pharmacal Research
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• v.27 no.9
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• pp.923-929
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• 2004

Stylopine is a major component of the leaf of Chelidonium majus L. (Papaveraceae), which has been used for the removal of warts, papillomas and condylomas, as well as the treatment of liver disease, in oriental countries. Stylopine per se had no cytotoxic effect in unstimulated RAW 264.7 cells, but concentration-dependently reduced nitric oxide (NO), prostaglandin E$_2$ (PGE$_2$), tumor necrosis factor-a (TNF-$\alpha$) and interleukin-1$\beta$(IL-1$\beta$), and the IL-6 production and cyclooxygenase-2 (COX-2) activity caused by the LPS stimulation. The levels of inducible nitric oxide synthase (iNOS) and COX-2 protein expressions were markedly suppressed by stylopine in a concentration dependent manner. These results suggest that stylopine suppress the NO and PGE$_2$ production in macrophages by inhibiting the iNOS and COX-2 expressions. These biological activities of stylopine may contribute to the anti-inflammatory activity of Cheli-donium majus.

• Korean Journal of Pharmacognosy
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• v.32 no.1 s.124
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• pp.10-14
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• 2001

Three alkaloids, (-)-stylopine (I), (+)-chelidonine (II), oxysanguinarine (III) and two triterpenoids, $6{\alpha}-hydroxy-A-neo-germacer-22(29)-en-30-oic\;acid$ (IV) and hop-22(29)-en-30-oic acid (V), were isolated from the methanol extract of of Chelidonium majus var. asiaticum, and their cytotoxicity were tested against five cultured human tumor cell lines.

• Journal of Applied Biological Chemistry
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• v.48 no.4
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• pp.198-201
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• 2005

Two known isoquinoline alkaloids, (+)-chelidonine (1) and (-)-stylopine (2), were isolated from $CHCl_3$-soluble fraction of whole plants of Chelidonium majus L. var. asiaticum, and their structures were identified by spectroscopic methods and X-ray crystallographic analysis. Two isolates (1 and 2) were examined for their in vitro cytotoxic activities against five human cancer cell lines including DU-145 (prostate), MCF (breast), A549 (lung), HePG2 (liver), and HT-29 (colon) by sulphorhodamine B (SRB) assay.

• Journal of Microbiology and Biotechnology
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• v.28 no.2
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• pp.262-266
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• 2018

Phytochemicals have been considered as alternatives for synthetic fungicides because of their biodegradability and low toxicity. In this study, we found that the methanolic extract of Corydalis ternata suppressed the development of plant diseases caused by Puccinia triticina and Colletotrichum coccodes. As the antifungal substance, three isoquinoline alkaloids (dehydrocorydaline, stylopine, and corydaline) were isolated from C. ternata. These active compounds also exhibited in vivo antifungal activity against P. triticina and C. coccodes. Taken together, our results suggest that C. ternata and its active compounds can be used to control plant diseases.

• Natural Product Sciences
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• v.4 no.4
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• pp.257-262
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• 1998

The extract of the aerial parts of Fumaria bastardii Bor. afforded 12 alkaloids belonging to the skeletally six different groups of the isoquinoline alkaloids. In this publication, the isolation and identification of protopine (1), corydaldine (2), oxyhydrastinine (3), (-)-fumaritine (4), (+)-fumariline (5), (-)-O-methylfumarophycine (12), (+)-bicuculline (10), $(-)-{\beta}-hydrastine$ (7), (-)-corlumine (11), (+)-tetrahydropalmatine (8), (-)-stylopine (6), and (+)-juziphine (9) are described. Their structures have been determined by using extensive spectroscopic techniques. This is the first report of the occurrence of these alkaloids in Fumaria bastardii of Turkish origin.

• Analytical Science and Technology
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• v.30 no.6
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• pp.379-389
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• 2017

In this study, we set up an analytical method that can be used for rapid and accurate determination of representative isoquinoline alkaloids in medicinal plants using UPLC-ESI-Q-TOF MS (ultra pressure liquid chromatography-electrospray ionization-quadrupole-time-of-flight mass spectrometry). The compounds were eluted on a C18 column with 0.1 % formic acid and acetonitrile, and separated with good resolution within 13 min. Each of the separated components was characterized by precursor ions (generated by ESI-Q-TOF) and fragment ions (produced by collision-induced dissociation, CID), which were used as a reliable database. We also performed method validation: analytes showed excellent linearity ($R^2$, 0.9971-0.9996), LOD (5-25 ng/mL), LOQ (17-82 ng/mL), accuracy (91.6-97.4 %) as well as intra- and inter-day precisions (RSD, 1.8-3.2 %). In the analysis of Chelidonium majus L., magnoflorine, coptisine, sanguinarine, berberine and palmatine were detected by matching retention times and characteristic fragment ion patterns of reference standards. We also confirmed that, among the quantified components, coptisine was present in the highest quantity. Furthermore, alkaloid profiling was carried out by analyzing the fragment ion patterns corresponding to peaks of unknown components. In this manner, protopine, chelidonine, stylopine, dihydroberberine, canadine, and nitidine were tentatively identified. We also proposed the molecular structure of the fragment ions that appear in the mass spectrum. Therefore, we concluded that our suggested method for the determination of major isoquinoline alkaloids by UPLC-Q-TOF can be useful not only for quality control, but also for rapid and accurate investigation of phytochemical constituents of medicinal plants.

• Journal of Applied Biological Chemistry
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• v.58 no.3
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• pp.281-285
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• 2015

Human neutrophil elastase (HNE) represents a good therapeutic target for the treatment of inflammatory diseases as well as invasion of microorganism. The methanol extract of a aerial part of Chelidonium majus L. showed high activity against the neutrophil elastase with an $IC_{50}$ value of $100{\mu}g/mL$. Due to its potency, subsequent bioactivity-guided fractionation of methanol extract led to six alkaloids (1-6), which were identified as dihydrosanguinarine (1), (s)-stylopine (2), arnottianamide (3), (+)-chelidonine (4), spallidamine (5), and N-trans-feruloyltyramine (6). Among of them, three alkaloids (2, 5, and 6) inhibited HNE in a dose-dependent manner with $IC_{50}$ ranging between 11.6 and $51.0{\mu}M$. Lineweaver-Burk and Dixon plots, and their secondary replots showed that alkaloids (2, 5, and 6) were mixed inhibitors of HNE. The analysis of $K_I$ and $K_{IS}$ value proved that all inhibitors (2, 5, and 6) had reversible mixed type I mechanism.