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Journal articles on the topic 'Bulbocapnine'

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Published: 29 July 2024

Last updated: 30 July 2024

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1

Ribár, B., C. Mèszáros, O. Gašić, I. Kanyó, and P. Engel. "Structure of bulbocapnine." Acta Crystallographica Section C Crystal Structure Communications 47, no. 12 (December 15, 1991): 2612–14. http://dx.doi.org/10.1107/s0108270191006480.

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2

Parvin, Mst, Marcel Hrubša, Jaka Fadraersada, Alejandro Carazo, Jana Karlíčková, Lucie Cahlíková, Jakub Chlebek, Kateřina Macáková, and Přemysl Mladěnka. "Can Isoquinoline Alkaloids Affect Platelet Aggregation in Whole Human Blood?" Toxins 14, no. 7 (July 15, 2022): 491. http://dx.doi.org/10.3390/toxins14070491.

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Isoquinoline alkaloids have multiple biological activities, which might be associated with positive pharmacological effects as well as negative adverse reactions. As bleeding was suggested to be a side effect of the isoquinoline alkaloid berberine, we decided to ascertain if different isoquinoline alkaloids could influence hemocoagulation through the inhibition of either platelet aggregation or blood coagulation. Initially, a total of 14 compounds were screened for antiplatelet activity in whole human blood by impedance aggregometry. Eight of them demonstrated an antiplatelet effect against arachidonic acid-induced aggregation. Papaverine and bulbocapnine were the most potent compounds with biologically relevant IC50 values of 26.9 ± 12.2 μM and 30.7 ± 5.4 μM, respectively. Further testing with the same approach confirmed their antiplatelet effects by employing the most physiologically relevant inducer of platelet aggregation, collagen, and demonstrated that bulbocapnine acted at the level of thromboxane receptors. None of the alkaloids tested had an effect on blood coagulation measured by a mechanical coagulometer. In conclusion, the observed antiplatelet effects of isoquinoline alkaloids were found mostly at quite high concentrations, which means that their clinical impact is most likely low. Bulbocapnine was an exception. It proved to be a promising antiplatelet molecule, which may have biologically relevant effects.

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3

RIBAR, B., C. MESZAROS, O. GASIC, I. KANYO, and P. ENGEL. "ChemInform Abstract: Structure of Bulbocapnine." ChemInform 23, no. 14 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199214302.

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4

Zhang, Yong, Jung Shin, Sang Lee, So Kim, and Myung Lee. "Inhibition of Tyrosine Hydroxylase by Bulbocapnine." Planta Medica 63, no. 04 (August 1997): 362–63. http://dx.doi.org/10.1055/s-2006-957702.

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5

Shafiee, Abbas, Katayoun Morteza-Semnani, and Mohsen Amini. "(+)-Bulbocapnine-β-N-oxide fromGlaucium fimbrilligerum." Journal of Natural Products 61, no. 12 (December 1998): 1564–65. http://dx.doi.org/10.1021/np9801920.

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6

Slavík, Jiří, Ladislav Dolejš, and Leonora Slavíková. "Alkaloids from Corydalis solida (L.) SW. mass spectrometry of quaternary benzylisoquinoline alkaloids." Collection of Czechoslovak Chemical Communications 50, no. 10 (1985): 2299–309. http://dx.doi.org/10.1135/cccc19852299.

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From the strongly polar fraction from the tubers of Corydalis solida (L.) SW., a new quaternary alkaloid, (+)-N-methyllaudanidinium iodide, was isolated after conversion to iodides. Mass spectrometric behaviour of this type of quaternary alkaloids is described. In the tubers (0.37% of alkaloids) the main alkaloid component is (+)- and (±)-tetrahydropalmatine; other dominant alkaloids include protopine, (+)-corydaline, allocryptopine, dehydrocorydaline and jatrorrhizine. (±)-Corybulbine, (+)-corypalmine, (-)-isocorypalmine, (-)-scoulerine, (-)-stylopine, corysamine, palmatine, (+)-N-methyllaudanidinium hydroxide, (-)-cis-N-methylcanadinium hydroxide and cis-N-methylstylopinium hydroxide represent minor alkaloids. The last three mentioned were isolated in the form of iodides. Bulbocapnine, coptisine, berberine and columbamine were detected in trace amounts. The main alkaloid of the aerial parts of the plant (0.35% of alkaloids) is berberine, accompanied by coptisine, (-)- and (±)-canadine, (-)-stylopine, isoboldine, protopine, columbamine and (-)-cis-N-methylcanadinium hydroxide (isolated in the form of iodide) as significant components. Among minor alkaloids allocryptopine, (-)-isocorypalmine, (+)-corypalmine, (±)- and (-)-tetrahydropalmatine, corysamine, dehydrothalictricavine, palmatine and cis-N-methylstylopinium hydroxide (as iodide) were isolated and trace amounts of jatrorrhizine and bulbocapnine were detected.

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7

Kohli, Jai D., Dana Glock, and Leon I. Goldberg. "Bulbocapnine is not a selective DA1 receptor antagonist." Journal of Pharmacy and Pharmacology 38, no. 5 (May 1986): 401–2. http://dx.doi.org/10.1111/j.2042-7158.1986.tb04599.x.

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8

Sourkes, Theodore L. ""Rational hope" in the early treatment of Parkinson's disease." Canadian Journal of Physiology and Pharmacology 77, no. 6 (July 1, 1999): 375–82. http://dx.doi.org/10.1139/y99-049.

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The drug treatment of Parkinson's disease since the original description of the malady in 1817 is described. Consideration is given to the historic use of alkaloids of the belladonna, harmala, and aporphine families, and of amphetamine. The introduction of the L-dopa treatment is described. The modes of action of the various drugs employed in the past as well as those in current use are described in the context of knowledge of the functioning of the nigrostriatal tract.Key words: anticholinergic drugs, apomorphine, bulbocapnine, L-dopa, harmine.

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9

Shin, Jung Soo, Kyong Tai Kim, and Myung Koo Lee. "Inhibitory effects of bulbocapnine on dopamine biosynthesis in PC12 cells." Neuroscience Letters 244, no. 3 (March 1998): 161–64. http://dx.doi.org/10.1016/s0304-3940(98)00148-7.

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10

Kaya, G. Irem, Nehir Unver, Belkıs Gözler, and Jaume Bastida. "(−)-Capnoidine and (+)-bulbocapnine from an Amaryllidaceae species, Galanthus nivalis subsp. cilicicus." Biochemical Systematics and Ecology 32, no. 11 (November 2004): 1059–62. http://dx.doi.org/10.1016/j.bse.2004.03.006.

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11

Chlebek, Jakub, Kateřina Macáková, Lucie Cahlíková, Milan Kurfürst, Jiří Kuneš, and Lubomír Opletal. "Acetylcholinesterase and Butyrylcholinesterase Inhibitory Compounds from Corydalis Cava (Fumariaceae)." Natural Product Communications 6, no. 5 (May 2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600507.

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Tubers of Corydalis cava were extracted with ethanol and fractionated using n-hexane, chloroform and ethanol. Repeated column chromatography, preparative TLC and crystallization led to the isolation of fifteen isoquinoline alkaloids. The chemical structures of the isolated compounds were determined on the basis of spectroscopic techniques and by comparison with literature data. All isolated compounds were tested for human blood acetylcholinesterase (HuAChE) and human plasma butyrylcholinesterase (HuBuChE) inhibitory activity. (+)-Canadaline inhibited acetylcholinesterase as well as butyrylcholinesterase in a dose-dependent manner with IC50 values of 20.1 ± 1.1 μM and 85.2 ± 3.2 μM, respectively. (+)-Canadine, with an IC50 value of 12.4 ± 0.9 μM, was the most potent inhibitor of acetylcholinesterase, whilst (±)-corycavidine and (+)-bulbocapnine were effective inhibitors of butyrylcholinesterase with IC50 values of 46.2 ± 2.4 uM and 67.0 ± 2.1 μM, respectively. The other isolated alkaloids were considered inactive (IC50 > 100 μM).

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12

Wada, Juhn A. "BEHAVIORAL AND ELECTROGRAPHIC EFFECTS OF INTRAVENTRICULAR INJECTION OF BULBOCAPNINE AND OTHER SUBSTANCES IN FREELY MOVING MONKEYS *†." Annals of the New York Academy of Sciences 96, no. 1 (December 15, 2006): 227–50. http://dx.doi.org/10.1111/j.1749-6632.1962.tb50119.x.

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13

Platella, Chiara, Francesca Ghirga, Pasquale Zizza, Luca Pompili, Simona Marzano, Bruno Pagano, Deborah Quaglio, et al. "Identification of Effective Anticancer G-Quadruplex-Targeting Chemotypes through the Exploration of a High Diversity Library of Natural Compounds." Pharmaceutics 13, no. 10 (October 3, 2021): 1611. http://dx.doi.org/10.3390/pharmaceutics13101611.

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In the quest for selective G-quadruplex (G4)-targeting chemotypes, natural compounds have been thus far poorly explored, though representing appealing candidates due to the high structural diversity of their scaffolds. In this regard, a unique high diversity in-house library composed of ca. one thousand individual natural products was investigated. The combination of molecular docking-based virtual screening and the G4-CPG experimental screening assay proved to be useful to quickly and effectively identify—out of many natural compounds—five hit binders of telomeric and oncogenic G4s, i.e., Bulbocapnine, Chelidonine, Ibogaine, Rotenone and Vomicine. Biophysical studies unambiguously demonstrated the selective interaction of these compounds with G4s compared to duplex DNA. The rationale behind the G4 selective recognition was suggested by molecular dynamics simulations. Indeed, the selected ligands proved to specifically interact with G4 structures due to peculiar interaction patterns, while they were unable to firmly bind to a DNA duplex. From biological assays, Chelidonine and Rotenone emerged as the most active compounds of the series against cancer cells, also showing good selectivity over normal cells. Notably, the anticancer activity correlated well with the ability of the two compounds to target telomeric G4s.

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14

Slavík, Jiří, and Leonora Slavíková. "Alkaloids from Corydalis nobilis (L.) PERS. and C. intermedia (L.) MÉRAT." Collection of Czechoslovak Chemical Communications 54, no. 7 (1989): 2009–20. http://dx.doi.org/10.1135/cccc19892009.

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Rhizomes of Corydalis nobilis (L.) PERS. (3% of alkaloids) contain (+)-tetrahydropalmatine, (+)-bicuculline and (+)-corytuberine as the main constituents of the tertiary alkaloid fraction. Protopine, (+)-corypalmine and (+)-stylopine, which also belong to the dominant alkaloids, were isolated in lesser amounts. As minor alkaloids were isolated (±)-tetrahydropalmatine, (+)-corydaline, allocryptopine, cryptopine, (-)-scoulerine, (+)-adlumidine, (+)-sinactine, (±)-corlumine, isoboldine, (+)-corybulbine, (±)-stylopine and (-)-isocorypalmine. The fraction of quaternary protoberberine alkaloids afforded coptisine dehydrocorydaline, palmatine, corysamine jatrorrhizine and cis-N-methylstylopinium hydroxide. Aobamidine (Z-adlumidiceine enol lactone), isolated as the principal alkaloid of aerial parts (0.3% of alkaloids), is obviously an artifact arising from bicuculline N-metho salt during the isolation process. Further dominant alkaloids of the tertiary fraction were adlumidine, bicuculline, protopine, (±)-tetrahydropalmatine and (±)-corlumine; as minor alkaloids were isolated corytuberine, scoulerine, corypalmine, cryptopine, isocorypalmine, corybulbine, (+)-corydalizine, and unidentified alkaloids CN 1 (C23H25NO5, m.p. 211 °C) and CN 2 (m.p. 261 °C). Quaternary protoberberine fraction afforded coptisine and palmatine. Nineteen of the mentioned alkaloids were isolated from this species for the first time. Tubers of C. intermedia (L.) MÉRAT (0.70% of alkaloids) afforded protopine, tetrahydropalmatine and corydaline as the main alkaloids and allocryptopine, canadine stylopine, palmatine, dehydrocorydaline, berberine, coptisine as minor alkaloids, together with traces of bicuculline and magnoflorine. Dominant alkaloids of the aerial part (0.73% of alkaloids) were bicuculline, bulbocapnine, protopine, stylopine and an unidentified phenolic base, m.p. 258 °C. Isoboldine, scoulerine, allocryptopine, corydaline, canadine, coptisine, palmatine and berberine were identified as the minor alkaloids.

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15

Soicke, Hartwig, Gabriele Al-Hassan, Ursula Frenzel, and Klaus Görler. "Versuche zur photochemischen Synthese von Bulbocapnin." Archiv der Pharmazie 321, no. 3 (1988): 149–52. http://dx.doi.org/10.1002/ardp.19883210308.

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16

Danilkiewicz, Maria. "Microscopic parasitic fungi of Chmielinne nature reserve." Acta Mycologica 18, no. 2 (August 20, 2014): 203–12. http://dx.doi.org/10.5586/am.1982.016.

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The microscopic parasitic fungi occurring in vegetal complex of Chmielinne nature reserve were investigate in the years 1976-1978. 85 species of fungi were gatherd on 71 specier of hosts. There are species among them which occur rarely in Polands flora: <i>Plasmopara ribicola, Peronospora agrimoniae, P. bulbocapni</i> and <i>P. corydalis</i>.

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17

Erdogan Orhan, Ilkay, F. Sezer Senol Deniz, Ramin Ekhteiari Salmas, Esra Emerce, and Bilge Sener. "Cholinesterase Inhibitory and In Silico Toxicity Assessment of Thirty-Four Isoquinoline Alkaloids – Berberine as the Lead Compound." CNS & Neurological Disorders - Drug Targets 22 (April 17, 2023). http://dx.doi.org/10.2174/1871527322666230417083053.

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Background:: Cholinesterase (ChE) inhibitors used currently in clinics for the treatment of Alzheimer’s disease (AD) are the most prescribed drug class with nitrogen-containing chemical formula. Galanthamine, the latest generation anti-ChE drug, contains an isoquinoline structure Objective:: The aim of the current study was to investigate the inhibitory potential of thirty-four isoquinoline alkaloids, e.g. (-)-adlumidine, β-allocryptopine, berberine, (+)-bicuculline, (-)-bicuculline, (+)-bulbocapnine, (-)-canadine, (±)-chelidimerine, corydaldine, (±)-corydalidzine, (-)-corydalmine, (+)-cularicine, dehydrocavidine, (+)-fumariline, (-)-fumarophycine, (+)-α-hydrastine, (+)-isoboldine, 13-methylcolumbamine, (-)-norjuziphine, norsanguinarine, (-)-ophiocarpine, (-)-ophiocarpine-N-oxide, oxocularine, oxosarcocapnine, palmatine, (+)-parfumine, protopine, (+)-reticuline, sanguinarine, (+)-scoulerine, (±)-sibiricine, (±)-sibiricine acetate, (-)-sinactine, and (-)-stylopine isolated from several Fumaria (fumitory) and Corydalis species towards acetyl- (AChE) and butyrylcholinesterase (BChE) by microtiter plate assays. The alkaloids with strong ChE inhibition were proceeded to molecular docking simulations as well as in silico toxicity screening for their mutagenic capacity through VEGA QSAR (AMES test) consensus model and VEGA platform as statistical approaches. The inputs were evaluated in a simplified molecular input-line entry system (SMILES). Results:: ChE inhibition assays indicated that the highest AChE inhibition was caused by berberine (IC50: 0.72 ± 0.04 µg/mL), palmatine (IC50: 6.29 ± 0.61 µg/mL), β-allocryptopine (IC50: 10.62 ± 0.45 µg/mL), (-)-sinactine (IC50: 11.94 ± 0.44 µg/mL), and dehydrocavidine (IC50: 15.01 ± 1.87 µg/mL) as compared to that of galanthamine (IC50: 0.74 ± 0.01 µg/mL), the reference drug with isoquinoline skeleton. Less number of the tested alkaloids exhibited notable BChE inhibition. Among them, berberine (IC50: 7.67 ± 0.36 µg/mL) and (-)-corydalmine (IC50: 7.78 ± 0.38 µg/mL) displayed a stronger inhibition than that of galanthamine (IC50: 12.02 ± 0.25 µg/mL). The mutagenic activity was shown for β-allocryptopine, (+)- and (-)-bicuculline, (±)-corydalidzine, (-)-corydalmine, (+)-cularicine, (-)-fumarophycine, (-)-norjuziphine, (-)-ophiocarpine-N-oxide, (+)-scoulerine, (-)-sinactine, and (-)-stylopine by means of in silico experiments. The results obtained by molecular docking simulations of berberine, palmatine, and (-)-corydalmine suggested that the estimated free ligand-binding energies of these compounds inside the binding domains of their targets are reasonable to make them capable of establishing strong polar and nonpolar bonds with the atoms of the active site amino acids. method: The alkaloids with strong inhibition were proceeded to molecular docking simulations as well as in silico toxicity screening for their mutagenic capacity through VEGA QSAR (AMES test) consensus model and VEGA platform as statistical approaches. The inputs were evaluated in a simplified molecular input-line entry system &#40;SMILES&#41;. Conclusion:: Our findings revealed that berberine, palmatin, and (-)-corydalmine stand out as the most promising isoquinoline alkaloids in terms of ChE inhibition. Among them, berberine has displayed a robust dual inhibition against both ChEs and could be evaluated further as a lead compound for AD. other: -

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