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koumine

$240

  • Brand : BIOFRON

  • Catalogue Number : BD-D1306

  • Specification : 98%(HPLC)

  • CAS number : 1358-76-5

  • Formula : C20H22N2O2

  • Molecular Weight : 306.407

  • PUBCHEM ID : 91895267

  • Volume : 20MG

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Catalogue Number

BD-D1306

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8℃

Molecular Weight

306.407

Appearance

White crystalline powder

Botanical Source

Gelsemium elegans

Structure Type

Indoles/Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN1CC2(C3CC4C5=NC6=CC=CC=C6C52CC1C3CO4)C=C

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-

IUPAC Name

(1R,10R,12S,15S,16R,17S)-15-ethenyl-13-methyl-19-oxa-3,13-diazahexacyclo[14.3.1.02,10.04,9.010,15.012,17]icosa-2,4,6,8-tetraene

Applications

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].

Density

1.4±0.1 g/cm3

Solubility

Methanol; Chloroform; Acetone

Flash Point

217.8±28.7 °C

Boiling Point

436.5±45.0 °C at 760 mmHg

Melting Point

168℃

InChl

InChI=1S/C20H22N2O/c1-3-19-11-22(2)16-9-20(19)13-6-4-5-7-15(13)21-18(20)17-8-14(19)12(16)10-23-17/h3-7,12,14,16-17H,1,8-11H2,2H3/t12-,14+,16-,17+,19-,20+/m0/s1

InChl Key

VTLYEMHGPMGUOT-FXWNUWCSSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:1358-76-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29770147

Abstract

Despite decades of studies, the currently available drugs largely fail to control neuropathic pain. Koumine-an alkaloidal constituent derived from the medicinal plant Gelsemium elegans Benth.-has been shown to possess analgesic and anti-inflammatory properties; however, the underlying mechanisms remain unclear. In this study, we aimed to investigate the analgesic and anti-inflammatory effects and the possible underlying mechanisms of koumine. The analgesic and anti-inflammatory effects of koumine were explored by using chronic constriction injury of the sciatic nerve (CCI) neuropathic pain model in vivo and LPS-induced injury in microglia BV2 cells in vitro. Immunofluorescence staining and Western blot analysis were used to assess the modulator effect of koumine on microglia and astrocyte activation after CCI surgery. Enzyme-linked immunosorbent assay (ELISA) was used to evaluate the levels of proinflammatory cytokines. Western blot analysis and quantitative real-time polymerase chain reaction (qPCR) were used to examine the modulator effect of koumine on microglial M1 polarization. We found that single or repeated treatment of koumine can significantly reduce neuropathic pain after nerve injury. Moreover, koumine showed inhibitory effects on CCI-evoked microglia and astrocyte activation and reduced proinflammatory cytokine production in the spinal cord in rat CCI models. In BV2 cells, koumine significantly inhibited microglia M1 polarization. Furthermore, the analgesic effect of koumine was inhibited by a TSPO antagonist PK11195. These findings suggest that the analgesic effects of koumine on CCI-induced neuropathic pain may result from the inhibition of microglia activation and M1 polarization as well as the activation of astrocytes while sparing the anti-inflammatory responses to neuropathic pain.

Title

Koumine Attenuates Neuroglia Activation and Inflammatory Response to Neuropathic Pain

Author

Gui-Lin Jin 1 2 , Sai-Di He 1 , Shao-Mei Lin 1 3 , Li-Mian Hong 1 , Wan-Qing Chen 1 , Ying Xu 1 2 , Jian Yang 1 2 , Su-Ping Li 1 , Chang-Xi Yu 1 2

Publish date

2018 Mar 25

PMID

30214411

Abstract

Koumine, an indole alkaloid, is a major bioactive component of Gelsemium elegans. Previous studies have demonstrated that koumine has noticeable anti-inflammatory and analgesic effects in inflammatory and neuropathic pain (NP) models, but the mechanisms involved are not well understood. This study was designed to explore the analgesic effect of koumine on chronic constriction injury (CCI)-induced NP in rats and the underlying mechanisms, including astrocyte autophagy and apoptosis in the spinal cord. Rats with CCI-induced NP were used to evaluate the analgesic and anti-inflammatory effects of koumine. Lipopolysaccharide (LPS)-induced inflammation in rat primary astrocytes was also used to evaluate the anti-inflammatory effect of koumine. We found that repeated treatment with koumine significantly reduced and inhibited CCI-evoked astrocyte activation as well as the levels of pro-inflammatory cytokines. Meanwhile, we found that koumine promoted autophagy in the spinal cord of CCI rats, as reflected by decreases in the LC3-II/I ratio and P62 expression. Double immunofluorescence staining showed a high level of colocalization between LC3 and GFAP-positive glia cells, which could be decreased by koumine. Intrathecal injection of an autophagy inhibitor (chloroquine) reversed the analgesic effect of koumine, as well as the inhibitory effect of koumine on astrocyte activation in the spinal cord. In addition, TUNEL staining suggested that CCI-induced apoptosis was inhibited by koumine, and this inhibition could be abolished by chloroquine. Western blot analysis revealed that koumine significantly increased the level of Bcl-xl while inhibiting Bax expression and decreasing cleaved caspase-3. In addition, we found that koumine could decrease astrocyte-mediated neuroinflammation and enhance autophagy in primary cultured astrocytes. These results suggest that the analgesic effects of koumine on CCI-induced NP may involve inhibition of astrocyte activation and pro-inflammatory cytokine release, which may relate to the promotion of astrocyte autophagy and the inhibition for apoptosis in the spinal cord.

KEYWORDS

apoptosis; astrocyte; autophagy; koumine; neuropathic pain; rats.

Title

Koumine Decreases Astrocyte-Mediated Neuroinflammation and Enhances Autophagy, Contributing to Neuropathic Pain From Chronic Constriction Injury in Rats

Author

Gui-Lin Jin 1 2 , Rong-Cai Yue 1 , Sai-di He 1 , Li-Mian Hong 1 , Ying Xu 1 2 , Chang-Xi Yu 1 2 Affiliations Expand

Publish date

2018 Aug 30

PMID

28105568

Abstract

Koumine, an active alkaloid of neurotoxic plant Gelsemium, has been focused on its therapeutic uses, especially in central nervous system. Nevertheless, less is known about the neurological effects of koumine, which hampers its potential therapeutic exploitation. Moreover, as the anxiolytic potential of Gelsemium has raised many critical issues, its active principles on the anxiolytic and other neurological effects need to be further investigated. Here, we used functional observation battery (FOB) of mice to systematically measure the neurological effects of koumine at the effective doses, and then further confirmed its anxiolytic properties in open-field test (OFT) of mice and Vogel conflict test (VCT) of rats. Koumine exhibited anxiolytic-like activities but did not affect other autonomic, neurological and physical functions in FOB. Furthermore, koumine released anxiolytic responses and anti-punishment action in a manner similar to diazepam in OFT and VCT, respectively. The results constitutes solid set of fundamental data further demonstrating anxiolytic properties of koumine at the therapeutic doses without inducing adverse neurological effects, which supports the perspectives for the development of safe and effective koumine medicine against pathological anxiety.

KEYWORDS

Anxiety; Functional observation battery; Gelsemium; Koumine; Open field test; Vogel conflict test.

Title

Koumine Exhibits Anxiolytic Properties Without Inducing Adverse Neurological Effects on Functional Observation Battery, Open-Field and Vogel Conflict Tests in Rodents

Author

Chao-Jie Chen 1 , Zhi-Feng Zhong 2 , Zhi-Ming Xin 1 , Long-Hui Hong 1 , Yan-Ping Su 3 , Chang-Xi Yu 4 5

Publish date

2017 Apr