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Gelsemine

$250

  • Brand : BIOFRON

  • Catalogue Number : BF-G4004

  • Specification : 98%(HPLC)

  • CAS number : 509-15-9

  • Formula : C20H22N2O2

  • Molecular Weight : 322.4

  • PUBCHEM ID : 5390854

  • Volume : 25mg

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Catalogue Number

BF-G4004

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

322.4

Appearance

White crystal

Botanical Source

Gelsemium elegans

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN1CC2(C3CC4C5(C2C1C3CO4)C6=CC=CC=C6NC5=O)C=C

Synonyms

GELSAMINE/8abeta,9s*,10s*))-8alph/GESEMINE/(2'S,3S,5'S,6'R,8'R,11'S)-4'-Methyl-2'-vinylspiro[indole-3,7'-[9]oxa[4]azatetracyclo[6.3.1.0.0]dodecan]-2(1H)-one/gelsemine free base/Gelsemin

IUPAC Name

(1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-4'-methylspiro[1H-indole-3,7'-9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane]-2-one

Density

1.3±0.1 g/cm3

Solubility

Methanol; Chloroform; Acetone

Flash Point

252.2±28.7 °C

Boiling Point

493.4±45.0 °C at 760 mmHg

Melting Point

181-183ºC

InChl

InChI=1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11?,13?,15?,16?,17-,19-,20-/m0/s1

InChl Key

NFYYATWFXNPTRM-ZIWPNRSCSA-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#:509-15-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30581679

Abstract

Gelsemine is an important toxic substance extracted from Gelsemium elegans, which has a lot of biological functions in cells and organisms, but its toxicity has been rarely reported in Tetrahymena thermophila. In this study, we used the protozoan T. thermophila as an experimental model to investigate the potential toxicity-induced mechanism of gelsemine in the unicellular eukaryote. Our results clearly showed gelsemine inhibited T. thermophila growth in a dose-dependent manner. This exposure also resulted in oxidative stress on T. thermophila cells and antioxidant enzyme levels were significantly altered at high gelsemine levels (p < 0.05). Gelsemine produced a slight apoptotic effect at the highest (0.8 mg/mL) gelsemine level used here (p < 0.05). Furthermore, the toxin-induced DNA damage in a dose-dependent manner. The ultrastructural analysis also revealed mitophagic vacuoles at 0.4 and 0.8 mg/mL levels of gelsemine exposure. Moreover, expressions of oxidative stress-related and MAP kinase genes were significantly changed after exposure to 0.8 mg/mL level of gelsemine (p < 0.05). Altogether, our results clearly show that gelsemine from G. elegans can inhibit the growth via inducing oxidative stress and DNA damage in T. thermophila cells.

KEYWORDS

DNA damage; Gelsemine; Gene expression; Oxidative stress; T. thermophila

Title

Effects of gelsemine on oxidative stress and DNA damage responses of Tetrahymena thermophila.

Author

Ye Q1,2, Feng Y1,2, Wang Z1,2, Jiang W1,2, Qu Y1,2, Zhang C1,2, Zhou A1,2, Xie S1,2, Zou J1,2.

Publish date

2018 Dec 10

PMID

30668937

Abstract

Gelsemine, the principal active alkaloid from Gelsemium sempervirens Ait., and koumine, the most dominant alkaloids from Gelsemium elegans Benth., produced antinociception in a variety of rodent models of painful hypersensitivity. The present study explored the molecular mechanisms underlying gelsemine- and koumine-induced mechanical antiallodynia in neuropathic pain. The radioligand binding and displacement assays indicated that gelsemine and koumine, like glycine, were reversible and orthosteric agonists of glycine receptors with full efficacy and probably acted on same binding site as the glycine receptor antagonist strychnine. Treatment with gelsemine, koumine and glycine in primary cultures of spinal neurons (but not microglia or astrocytes) concentration dependently increased 3α-hydroxysteroid oxidoreductase (3α-HSOR) mRNA expression, which was inhibited by pretreatment with strychnine but not the glial inhibitor minocycline. Intrathecal injection of gelsemine, koumine and glycine stimulated 3α-HSOR mRNA expression in the spinal cords of neuropathic rats and produced mechanical antiallodynia. Their spinal mechanical antiallodynia was completely blocked by strychnine, the selective 3α-HSOR inhibitor medroxyprogesterone acetate (MPA), 3α-HSOR gene silencer siRNA/3α-HSOR and specific GABAA receptor antagonist isoallopregnanolone, but not minocycline. All the results taken together uncovered that gelsemine and koumine are orthosteric agonists of glycine receptors, and produce mechanical antiallodynia through neuronal glycine receptor/3α-HSOR/allopregnanolone/GABAA receptor pathway.

Copyright © 2019. Published by Elsevier Inc.

KEYWORDS

3α-HSOR; Allopregnanolone; Gelsemine; Glycine receptor; Koumine

Title

Gelsemine and koumine, principal active ingredients of Gelsemium, exhibit mechanical antiallodynia via spinal glycine receptor activation-induced allopregnanolone biosynthesis.

Author

Shoaib RM1, Zhang JY1, Mao XF1, Wang YX2.

Publish date

2019 Mar

PMID

26388157

Abstract

AIM:
Gelsemine, an alkaloid from the Chinese herb Gelsemium elegans (Gardn & Champ) Benth., is effective in mitigating chronic pain in rats. In the present study we investigated whether the alkaloid improved sleep disturbance, the most common comorbid symptoms of chronic pain, in a mouse model of neuropathic pain.

METHODS:
Mice were subjected to partial sciatic nerve ligation (PSNL). After the mice were injected with gelsemine or pregabalin (the positive control) intraperitoneally, mechanical allodynia and thermal hyperalgesia were assessed, and electroencephalogram (EEG)/electromyogram (EMG) recording was performed. Motor performance of the mice was assessed using rota-rod test. c-Fos expression in the brain was analyzed with immunohistochemical staining.

RESULTS:
In PSNL mice, gelsemine (2 and 4 mg/kg) increased the mechanical threshold for 4 h and prolonged the thermal latencies for 3 h. Furthermore, gelsemine (4 mg/kg, administered at 6:30 AM) increased non-rapid eye movement (non-REM, NREM) sleep, decreased wakefulness, but did not affect REM sleep during the first 3 h in PSNL mice. Sleep architecture analysis showed that gelsemine decreased the mean duration of wakefulness and increased the total number of episodes of NREM sleep during the first 3 h after the dosing. Gelsemine (4 mg/kg) did not impair motor coordination in PSNL mice. Immunohistochemical study showed that PSNL increased c-Fos expression in the neurons of the anterior cingulate cortex, and gelsemine (4 mg/kg) decreased c-Fos expression by 58%. Gelsemine (4 mg/kg, administered at either 6:30 AM or 8:30 PM) did not produce hypnotic effect in normal mice. Pregabalin produced similar antinociceptive and hypnotic effects, but impaired motor coordination in PSNL mice.

CONCLUSION:
Gelsemine is an effective agent for treatment of both neuropathic pain and sleep disturbance in PSNL mice; anterior cingulate cortex might play a role in the hypnotic effects of gelsemine.

Title

Gelsemine alleviates both neuropathic pain and sleep disturbance in partial sciatic nerve ligation mice.

Author

Wu YE1,2, Li YD2, Luo YJ2, Wang TX2, Wang HJ2, Chen SN2, Qu WM2,3, Huang ZL1,2,3.

Publish date

2015 Nov


Description :

Gelsemine, an alkaloid from the Chinese herb Gelsemium elegans, is effective in mitigating chronic pain. Antinociceptive and hypnotic effects.