Gelsemine

CAS# 509-15-9

Gelsemine

Catalog No. BCN5804----Order now to get a substantial discount!

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Gelsemine: 5mg $127 In Stock
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Quality Control of Gelsemine

Number of papers citing our products

Chemical structure

Gelsemine

3D structure

Chemical Properties of Gelsemine

Cas No. 509-15-9 SDF Download SDF
PubChem ID 6713959 Appearance White powder
Formula C20H22N2O2 M.Wt 322.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility DMSO : ≥ 125 mg/mL (387.72 mM)
*"≥" means soluble, but saturation unknown.
SMILES CN1CC2(C3CC4C5(C2C1C3CO4)C6=CC=CC=C6NC5=O)C=C
Standard InChIKey NFYYATWFXNPTRM-ZIWPNRSCSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Gelsemine

The root of Gelsemium elegans (Gardn. et Champ.) Benth.

Biological Activity of Gelsemine

DescriptionGelsemine is a highly toxic compound and may be a glycine receptor agonist. Gelsemine has antitumor, anti-hyperlipidemic,anti-oxidative activities,it also has marked antinociception in inflammatory, neuropathic and bone cancer pains without inducing antinociceptive tolerance.
TargetsLDL
In vitro

Antitumor activity of two gelsemine metabolites in rat liver microsomes.[Pubmed: 20839118]

J Asian Nat Prod Res. 2010 Sep;12(9):731-9.

Gelsemine is one of the major alkaloids from Gelsemium elegans Benth., which has been used as an antitumor remedy in clinic.
METHODS AND RESULTS:
In this paper, metabolism of Gelsemine has been investigated in vitro in phenobarbital-treated rat liver microsomes. The metabolites of Gelsemine were separated and evaluated using the flash silica gel column, preparative HPLC, using NMR and MS methods. According to the spectral data, two metabolites, M1 and M2, were identified as 4-N-demethylGelsemine and 21-oxoGelsemine, respectively. By the MTT method in vitro, the antitumor activities between Gelsemine and its metabolites were compared in the HepG2 and HeLa cell lines. Moreover, the main metabolic pathway was further proposed.

In vivo

Anti-hyperlipidemic and anti-oxidative effects of gelsemine in high-fat-diet-fed rabbits.[Pubmed: 25213292]

Cell Biochem Biophys. 2015 Jan;71(1):337-44.

The present study investigated the anti-hyperlipidemic proprieties of a natural alkaloid, Gelsemine, in a high-fat-fed rabbit model.
METHODS AND RESULTS:
Animals were randomly divided into five groups and fed normal diet, hypercholesterolemic diet (1% cholesterol), or hypercholesterolemic diet (1% cholesterol) supplemented with Gelsemine (1, 5, or 25 mg/kg). After 60 days, serum concentrations of total cholesterol (TC), LDL-C, HDL-C, triglycerides, apolipoproteins A and B, SGOT, SGPT, glucose, and insulin were measured in all experimental groups. Hypercholesterolemic diet resulted in significantly elevated levels of TC, TG, LDL-C, SGOT, and SGPT, and reduced HDL-C compared to the normocholesterolemic diet group. Gelsemine treatment significantly improved lipid profile parameters, affected by hyperlipidemia, while having no effect on the levels of apolipoproteins, glucose, and insulin. Furthermore, Gelsemine treatment decreased hyperlipidemia-induced oxidative stress in a dose-dependent manner, as indicated by the increased activity of superoxide dismutase and catalase, and reduction in serum nitric oxide, and malondialdehyde concentrations in hyperlipidemic animals that received Gelsemine supplementation.
CONCLUSIONS:
Dietary supplementation with Gelsemine may, therefore, reverse the effect of the lipogenic diet on lipid profile and hepatic enzymes in hyperlipidemic rabbits, and protect tissues from oxidative stress, caused by high-fat diet.

Protocol of Gelsemine

Structure Identification
Org Lett. 2008 Nov 6;10(21):4747-50.

A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy.[Pubmed: 18837555]

A tricyclic core structure 2 related to Gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.

Gelsemine Dilution Calculator

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Gelsemine Molarity Calculator

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Preparing Stock Solutions of Gelsemine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1017 mL 15.5087 mL 31.0174 mL 62.0347 mL 77.5434 mL
5 mM 0.6203 mL 3.1017 mL 6.2035 mL 12.4069 mL 15.5087 mL
10 mM 0.3102 mL 1.5509 mL 3.1017 mL 6.2035 mL 7.7543 mL
50 mM 0.062 mL 0.3102 mL 0.6203 mL 1.2407 mL 1.5509 mL
100 mM 0.031 mL 0.1551 mL 0.3102 mL 0.6203 mL 0.7754 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Gelsemine

Antitumor activity of two gelsemine metabolites in rat liver microsomes.[Pubmed:20839118]

J Asian Nat Prod Res. 2010 Sep;12(9):731-9.

Gelsemine is one of the major alkaloids from Gelsemium elegans Benth., which has been used as an antitumor remedy in clinic. In this paper, metabolism of Gelsemine has been investigated in vitro in phenobarbital-treated rat liver microsomes. The metabolites of Gelsemine were separated and evaluated using the flash silica gel column, preparative HPLC, using NMR and MS methods. According to the spectral data, two metabolites, M1 and M2, were identified as 4-N-demethylGelsemine and 21-oxoGelsemine, respectively. By the MTT method in vitro, the antitumor activities between Gelsemine and its metabolites were compared in the HepG2 and HeLa cell lines. Moreover, the main metabolic pathway was further proposed.

A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy.[Pubmed:18837555]

Org Lett. 2008 Nov 6;10(21):4747-50.

A tricyclic core structure 2 related to Gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.

Anti-hyperlipidemic and anti-oxidative effects of gelsemine in high-fat-diet-fed rabbits.[Pubmed:25213292]

Cell Biochem Biophys. 2015 Jan;71(1):337-44.

The present study investigated the anti-hyperlipidemic proprieties of a natural alkaloid, Gelsemine, in a high-fat-fed rabbit model. Animals were randomly divided into five groups and fed normal diet, hypercholesterolemic diet (1% cholesterol), or hypercholesterolemic diet (1% cholesterol) supplemented with Gelsemine (1, 5, or 25 mg/kg). After 60 days, serum concentrations of total cholesterol (TC), LDL-C, HDL-C, triglycerides, apolipoproteins A and B, SGOT, SGPT, glucose, and insulin were measured in all experimental groups. Hypercholesterolemic diet resulted in significantly elevated levels of TC, TG, LDL-C, SGOT, and SGPT, and reduced HDL-C compared to the normocholesterolemic diet group. Gelsemine treatment significantly improved lipid profile parameters, affected by hyperlipidemia, while having no effect on the levels of apolipoproteins, glucose, and insulin. Furthermore, Gelsemine treatment decreased hyperlipidemia-induced oxidative stress in a dose-dependent manner, as indicated by the increased activity of superoxide dismutase and catalase, and reduction in serum nitric oxide, and malondialdehyde concentrations in hyperlipidemic animals that received Gelsemine supplementation. Dietary supplementation with Gelsemine may, therefore, reverse the effect of the lipogenic diet on lipid profile and hepatic enzymes in hyperlipidemic rabbits, and protect tissues from oxidative stress, caused by high-fat diet.

Description

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

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