Introduction：Basic information about CAS 1358-76-5|Koumine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Koumine |
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| CAS Number | 1358-76-5 | Molecular Weight | 306.401 |
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| Density | 1.4±0.1 g/cm3 | Boiling Point | 436.5±45.0 °C at 760 mmHg |
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| Molecular Formula | C20H22N2O | Melting Point | 168℃ |
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| MSDS | / | Flash Point | 217.8±28.7 °C |
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Names
| Name | Koumine |
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| Synonym | More Synonyms |
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Koumine BiologicalActivity
| Description | Koumine is an alkaloid separated from Gelsemium elegans, shows potent anti-tumor activity. Koumine up-regulates the Bax/Bcl-2 ratio and caspase-3 expression in human breast cancer cells[1]. Koumine has anxiolytic, antistress, antipsoriatic, and analgesic activities[3], protects against the development of arthritis in Rheumatoid arthritis (RA) animal models[2]. |
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| Related Catalog | Signaling Pathways >>Others >>OthersResearch Areas >>CancerNatural Products >>AlkaloidResearch Areas >>Inflammation/Immunology |
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| In Vitro | Koumine (0.5, 1 and 2 mg/mL) dose- and time-dependently inhibits the proliferation of MCF-7 cells, with an IC50 of 124 µg/mL at 72 h. Koumine induces apoptosis, causes cell cycle arrest at G2/M phase[1]. Koumine (0.5, 1 and 2 mg/mL) up-regulates the Bax/Bcl-2 ratio and caspase-3 expression in a dose-dependent manner in MCF-7 Cells[1]. Koumine (25, 50, 100, and 200 μM) decreases the protein and mRNA levels of microglia M1 polarization factors in LPS-induced BV2 cells[3]. |
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| In Vivo | Koumine is less toxic, with the median lethal dose (LD50) of 300.0 mg/kg on Wistar rats. Koumine (0.6, 3, or 15 mg/kg/per, p.o.) exhibits antirheumatic properties in rats with adjuvant-induced arthritis (AIA) and collagen-induced arthritis (CIA)[2]. Koumine inhibits the increase in cytokines in joint tissue and TNF-α level in serum at 15 mg/kg, and suppresses the increase in the serum level of IL-1β at 3 and 15 mg/kg[2]. Koumine (0.28, 7 mg/kg, s.c.) significantly reduces neuropathic pain after nerve injury. Koumine suppresses the increased Iba-1 protein level[3]. |
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| References | [1]. Zhang X, et al. Apoptotic Effect of Koumine on Human Breast Cancer Cells and the Mechanism Involved. Cell Biochem Biophys. 2015 Jun;72(2):411-6. [2]. Yang J, et al. Effects of Koumine on Adjuvant- and Collagen-Induced Arthritis in Rats. J Nat Prod. 2016 Oct 28;79(10):2635-2643. [3]. Jin GL, et al. Koumine Attenuates Neuroglia Activation and Inflammatory Response to Neuropathic Pain. Neural Plast. 2018 Mar 25;2018:9347696. |
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Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
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| Boiling Point | 436.5±45.0 °C at 760 mmHg |
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| Melting Point | 168℃ |
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| Molecular Formula | C20H22N2O |
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| Molecular Weight | 306.401 |
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| Flash Point | 217.8±28.7 °C |
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| Exact Mass | 306.173218 |
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| PSA | 24.83000 |
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| LogP | 2.18 |
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| Vapour Pressure | 0.0±1.0 mmHg at 25°C |
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| Index of Refraction | 1.763 |
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| InChIKey | VTLYEMHGPMGUOT-NUBFMYDXSA-N |
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| SMILES | C=CC12CN(C)C3CC14C(=Nc1ccccc14)C1CC2C3CO1 |
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| Storage condition | 2-8C |
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Synonyms
| 13-Methyl-15-vinyl-19-oxa-3,13-diazahexacyclo[14.3.1.0.0.0.0]icosa-2,4,6,8-tetraene |
| 6,4-(Epoxymethano)-3,11b-methano-11bH-pyrido[4,3-c]carbazole, 11c-ethenyl-1,2,3,4,4a,5,6,11c-octahydro-2-methyl-, (3S,4R,4aR,6R,11cS)- |
| (1R,12S,15S,16R,17R)-13-Methyl-15-vinyl-19-oxa-3,13-diazahexacyclo[14.3.1.0.0.0.0]icosa-2,4,6,8-tetraene |
| 6,4-(Epoxymethano)-3,11b-methano-11bH-pyrido[4,3-c]carbazole, 11c-ethenyl-1,2,3,4,4a,5,6,11c-octahydro-2-methyl- |
