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Facile synthesis of tetrahydroprotoberberine and protoberberine alkaloids from protopines and study on their antibacterial activities

A series of isoquinoline alkaloids including tetrahydroprotoberberines, N-methyl tetrahydroprotoberberines and protoberberines were facile synthesised with protopines as the starting material. All compounds were evaluated for their antibacterial activities against four pathogenic bacteria Escherichia coli, Staphyloccocus aureus, Staphylococcus gallinarum and Salmonella choleraesuis. Experimental results indicated that protoberberines were the most active compounds to the target bacteria among the tested alkaloids. It was suggested that planar molecule with high aromatisation level (e.g. coptisine 5 and berberine 6) or a positive charge of the molecules (e.g. N-methyl tetrahydroprotoberberines 11 and 12) had a positive influence on the antibacterial effects.

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A new tetrahydroprotoberberine N-oxide alkaloid and anti-platelet aggregation constituents of Corydalis tashiroi

A new tetrahydroprotoberberine N-oxide alkaloid, (-)-cis-isocorypalmine N-oxide (1), together with two known compounds, 6-methoxydihydrosanguinarine (2) and norjuziphine (3), were isolated in continuing studies of the entire Formosan Corydalis tashiroi plant. The structures of these three compounds were determined through spectral analyses. In addition, compounds 1, 2, 3 and the seven alkaloids previously reported: (-)-cis-corydalmine N-oxide, (-)-trans-corydalmine N-oxide, (-)-trans-isocorypalmine N-oxide, scoulerine, protopine, oxysanguinarine and corydalmine, were found to possess anti-platelet aggregation activity.

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 1081-17-0, name is 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione, introducing its new discovery. name: 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione

Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum

Two ethanolic dry extracts from the herb Chelidonium majus L. with a defined content of the main alkaloids (chelidonine, protopine, and coptisisine) and the alkaloids themselves were studied in three different antispasmodic test models on isolated ileum of guinea-pigs. In the BaCl2- stimulated ileum, chelidonine and protopine exhibited the known papaverine- like musculotropic action, whereas coptisine (up to 3.0 x 10-5 g/ml) was ineffective in this model. Both extracts were active with 53.5% and 49.0% relaxation at 5 x 10-4 g/ml. The carbachol and the electric field stimulated contractions were antagonized by all three alkaloids. Coptisine showed competitive antagonist behaviour with a pA2 value of 5.95. Chelidonine and protopine exhibited a certain degree of non-competitive antagonism. In the electric field the antagonist activities decreased in the order protopine > coptisine > chelidonine. The concentrations of the chelidonium herb extracts for 50% inhibition of the carbachol and electrical field induced spasms were in the range of 2.5 to 5 x 10-4g/ml.

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Protopine isolated from Nandina domestica induces apoptosis and autophagy in colon cancer cells by stabilizing p53

The tumor suppressor p53 plays essential roles in cellular protection mechanisms against a variety of stress stimuli and its activation induces apoptosis or autophagy in certain cancer cells. Here, we identified protopine, an isoquinoline alkaloid isolated from Nandina domestica, as an activator of the p53 pathway from cell-based natural compound screening based on p53-responsive transcription. Protopine increased the p53-mediated transcriptional activity and promoted p53 phosphorylation at the Ser15 residue, resulting in stabilization of p53 protein. Moreover, protopine up-regulated the expression of p21WAF1/CIP1 and BAX, downstream genes of p53, and inhibited the proliferation of HCT116 colon cancer cells. Apoptosis was elicited by protopine as indicated by caspase-3/7 activation, poly ADP ribose polymerase cleavage, and increased population of Annexin V-FITC-positive cells. Furthermore, protopine induced the formation of microtubule-associated protein 1 light chain 3 (LC3) puncta and LC3-II turnover, typical biochemical markers of autophagy, in HCT116 cells. Our findings suggest that protopine exerts its antiproliferative activity by stimulating the p53 pathway and may have potential as a chemopreventive agent for human colon cancer.

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One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, Application In Synthesis of 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 1081-17-0, Name is 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione, molecular formula is C11H9NO3

A summer inanimate object alkali process for preparation of monomer (by machine translation)

The invention discloses a method for preparing biological alkali monomer, comprising the following steps: the use of a high-speed centrifugal distribution chromatography to extract-free separation and purification of the summer, to obtain. The preparation method of this invention is capable of large scale preparation of the alkaloid monomer, gram level quantity preparation maximum can be achieved, and the prepared monomer has high purity, up to 98% or more; the cost is low, high separation efficiency, high recovery rate, the purity of the product is high, a biphenylene resin. (by machine translation)

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Application In Synthesis of 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 1081-17-0, in my other articles.

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Inhibitory effect of isoquinoline alkaloids on movement of second-stage larvae of Toxocara canis.

To find new anthelmintics against parasites living in host tissues, we used an in vitro assay to screen isoquinoline alkaloids for nematocidal activity on the larva of dog roundworm, Toxocara canis. To evaluate the efficacy of anthelmintics in vitro, Tsuda et al. previously introduced the concept of Relative Mobility (RM) of Toxocara larvae. After improvement of the assay system using image data processing, we generated a new index, RM(50), the concentration at which RM=50%. However, except for pyrantel, the RM(50) of most existing anthelmintics could not be calculated because of low activity. Of the isoquinoline alkaloids tested, emetine, sanguinarine, 6-methoxydihydrosanguinarine (6-MS), chelerythrine and berberine showed strong nematocidal activities. However, these compounds were highly cytotoxic; thus, the prospect of their direct application is low. We then tested the cytotoxicity (IC(50)) of other isoquinoline alkaloids in HL60 tissue-culture cells. We continued our search for new anthelmintics by examining in detail the relationship between RM(50) and IC(50). We determined that an ideal target compound would exhibit a low RM(50)/IC(50) ratio. Allocryptopine, dehydrocorydaline and papaverine were identified as potentially effective anthelmintics.

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ALKALOIDS FROM Papaver pinnatifidum Moris

Oripavine (Ia) was isolated from Papaver pinnatifidum Moris (tetraploid, 2n = 28) of the section Rhoeadium Spach as the major alkaloid.In a low yield, protopine and (+)-isocorydine were obtained together with a novel levorotatory alkaloid PP 1 of the composition C17H19NO3 and m.p. 179 deg C, probably of a normorphinane type.Small amounts of thebaine, allocryptopine, scoulerine, isoboldine, and papaverrubines A, C, and D, berberine, and corytuberine were also detected by thin layer chromatography.

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We¡¯ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of 1081-17-0, and how the biochemistry of the body works.category: pyrrolines

In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 1081-17-0, name is 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione, introducing its new discovery. category: pyrrolines

Dereplication study on Glaucium aleppicum Boiss. in Jordan

The secondary metabolite constituents of Glaucium aleppicum Boiss. et Hausskn. ex Boiass. (Papaveraceae) were investigated using an in-house developed Ultra Performance Liquid Chromatography-Photodiode Array-High Resolution Tandem Mass Spectrometry (UPLC-PDA-HRMS-MS/MS) method. In this study the powerful resolution and short analysis time afforded by UPLC coupled to the outstanding mass accuracy of an Orbitrap mass spectrometer was used to develop a rapid and effective dereplication method to identify secondary metabolite constituents of G. aleppicum in crude extracts. In addition, HCD MS/MS and UV (photodiode array) spectra were used as an integral part of the strategy. This methodology was applied on a small amount of extract (? 1 mg) of G. aleppicum to dereplicate twelve compounds. Five of which have been isolated previously from G. aleppicum: allocryptopine, protopine, corydine, isocorydine, and norchelidonine. Seven were new to the species, these include: dehydroglaucine, norisocorydine, chelerythrine, norsanguinarine, dihydrochelerythrine, corytuberine, and fumaflorine methyl ester. In addition to one more compound that was unidentified and thus considered new.

We¡¯ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of 1081-17-0, and how the biochemistry of the body works.category: pyrrolines

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Extracurricular laboratory:new discovery of 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione

The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 1081-17-0 is helpful to your research. Electric Literature of 1081-17-0

Electric Literature of 1081-17-0, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 1081-17-0, molcular formula is C11H9NO3, introducing its new discovery.

FLUORESCENCE PROPERTIES OF SOME ISOQUINOLINE ALKALOIDS

The fluorescence properties of 28 isoquinoline alkaloids have been investigated.In most of them the chromophore responsible for fluorescence was the benzene ring with electron-donor substituents containing oxygen.The long-wave excitation peak practically coincides with the long-wave absorption peak of these substances, covering the region from 284 to 293 nm, the maximum emission being in the range 320 – 332 nm.With alkaloids having a number of conjugated rings, both excitation and emission were observed at higher wavelengths.Only protoberberine alkaloids behaved as hydrophobic probes, i.e. transfer of these compounds into a less polar medium produced a marked hypsochromic shift and a higher intensity of emission.The effect of polarity on the behaviour of tetrahydroprotoberberines, protopines, pavinanes, aporphines and benzophenanthridines was not so pronounced.Changes of pH manifested themselves most markedly in compounds with dissociable hydroxyl groups; the majority of phenolates did not fluoresce.The phenol group pK values of these compounds in the excited state were lower than in the ground state (which ranged between 8.4 and 10.4).The relations between the apparent pK, determined from fluorescence data, and the pK’s of these compounds in the ground and the excited states are discussed.

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ALKALOIDS OF Papaver nudicaule SUBSP. xanthopetalum (TRAUTV.) FEDDE AND P. nudicaule SUBSP. album (REGEL) FEDDE FROM THE SECTION Scapiflora REICHB.

The alkaloidal composition in the two taxa differs only quantitatively.Both contain amurine as the main alkaloid.P. nudicaule ssp. xanthopetalum contains muramine, protopine and alkaloid PN1 (probably identical with (+/-)-nudaurine (Ia)) as dominant alkaloids; further were isolated amurensine, epialpinine, cryptopine, mecambridine and alpinigenine.Allocryptopine, papaverrubines A, B, D and G, palmatine and coptisine were detected chromatographically.The quaternary alkaloid fraction afforded cis-N-methylstylopinium hydroxide (as the iodide II) which was isolated for the first time from P. nudicaule.In P. nudicaule ssp. album the alkaloid PN1, epialpinine, amurensine and muramine represented the dominant alkaloids, accompanied with mecambridine, protopine, cryptopine, allocryptopine and alpinigenine.Among the quaternary alkaloids N-methylstylopinium hydroxide was found.

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