Vomicine

CAS# 125-15-5

Vomicine

2D Structure

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3D structure

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Vomicine

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Chemical Properties of Vomicine

Cas No. 125-15-5 SDF Download SDF
PubChem ID 101595 Appearance Powder
Formula C22H24N2O4 M.Wt 380.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Strychnicine
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CN1CCC23C4C5C(CC2=O)C(=CCOC5CC(=O)N4C6=C3C=CC=C6O)C1
Standard InChIKey ZMTYENXGROJCEA-LNKPQSDASA-N
Standard InChI InChI=1S/C22H24N2O4/c1-23-7-6-22-14-3-2-4-15(25)20(14)24-18(27)10-16-19(21(22)24)13(9-17(22)26)12(11-23)5-8-28-16/h2-5,13,16,19,21,25H,6-11H2,1H3/t13-,16-,19-,21-,22+/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 Vomicine

The seeds of Strychnos nux-vomica

Biological Activity of Vomicine

DescriptionVomicine is a natural product from Strychnos nux-vomica, the S. nux-vomica extracts show antihyperglycemic activity in experimental animals.
In vitro

New antimalarial and cytotoxic sungucine derivatives from Strychnos icaja roots.[Pubmed: 10821054]

Planta Med. 2000 Apr;66(3):262-9.


METHODS AND RESULTS:
Reinvestigation of Strychnos icaja Baillon resulted in the isolation of Vomicine, isostrychnine and of three new sungucine derivatives, named isosungucine (8), 18-hydroxy-sungucine (9) and 18-hydroxy-isosungucine (10). They were identified by detailed spectroscopic methods. The complete 1H- and 13C-NMR study of sungucine was also realized. Some of these compounds were highly active against Plasmodium falciparum in vitro and more particularly against the chloroquine-resistant strain.
CONCLUSIONS:
Compound 10 showed a selective antiplasmodial activity, with > 100-fold greater toxicity towards Plasmodium falciparum, relative to cultured human cancer cells (KB and HeLa lines) or fibroblasts (WI38).

Antiplasmodial alkaloids from the stem bark of Strychnos malacoclados.[Pubmed: 22193980 ]

Planta Med. 2012 Mar;78(4):377-82.

From the stem bark of Strychnos malacoclados, one new bisindole alkaloid, 3-hydroxylongicaudatine Y (1), was isolated along with the known alkaloids Vomicine (2), bisnordihydrotoxiferine (3), divarine (4), longicaudatine (5), longicaudatine Y (6), and longicaudatine F (7).
METHODS AND RESULTS:
All the compounds were tested for their antimalarial activity against the chloroquine-sensitive 3D7 and -resistant W2 strains of Plasmodium falciparum. Longicaudatine was the most active compound with IC₅₀ values of 0.682 and 0.573 µM, respectively. The activity of compounds 1, 3, 4, 6, and 7 against the two strains ranged from 1.191 to 6.220 µM and 0.573 to 21.848 µM, respectively. Vomicine (2), the only monomer isolated, was inactive. The alkaloids of the longicaudatine-type ( 1, 5-7) were more active than those of the caracurine-type (3- 4). The presence of the ether bridge in the molecule seems to increase the antiplasmodial activity. Compounds 1, 5, and 7 were tested against the WI-38 human fibroblast cell line. Longicaudatine was the most cytotoxic compound with an IC₅₀ of 2.721 µM.
CONCLUSIONS:
Longicaudatine F was 40-46 times more active against the two strains of P. falciparum than against the human fibroblasts and was thus considered as the more selective alkaloid. The structures of the compounds were determined based on the analysis of their spectral data.

In vivo

Strychnos nux-vomica seeds: Pharmacognostical standardization, extraction, and antidiabetic activity.[Pubmed: 22707864 ]

J Ayurveda Integr Med. 2012 Apr;3(2):80-4.

Strychnos nux-vomica, commonly known as kuchla, contains strychnine and brucine as main constituents. Minor alkaloids present in the seeds are protostrychnine, Vomicine, n-oxystrychnine, pseudostrychnine, isostrychnine, chlorogenic acid, and a glycoside. Seeds are used traditionally to treat diabetes, asthma, aphrodisiac and to improve appetite.The present study was aimed to evaluate the various pharmacognostical characters and antidiabetic activity of S. nux-vomica seed.
METHODS AND RESULTS:
Pharmacognostical characters were performed as per the WHO guideline. Extraction was carried out in petroleum ether, chloroform, alcohol, hydroalcoholic, aqueous, and phytochemical constituents present in extracts were detected by different chemical tests. Among these extracts hydroalcoholic, aqueous extracts were evaluated for antidiabetic activity on the basis of extractive yield and phytoconstituents, in alloxan-induced diabetic rats using gliclazide as standard. Various analytical values of S. nux-vomica extract were established. Phytoconstituents present in S. nux-vomica extracts were detected.
CONCLUSIONS:
S. nux-vomica extracts show antihyperglycemic activity in experimental animals.

Vomicine Dilution Calculator

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Preparing Stock Solutions of Vomicine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6288 mL 13.1441 mL 26.2881 mL 52.5762 mL 65.7203 mL
5 mM 0.5258 mL 2.6288 mL 5.2576 mL 10.5152 mL 13.1441 mL
10 mM 0.2629 mL 1.3144 mL 2.6288 mL 5.2576 mL 6.572 mL
50 mM 0.0526 mL 0.2629 mL 0.5258 mL 1.0515 mL 1.3144 mL
100 mM 0.0263 mL 0.1314 mL 0.2629 mL 0.5258 mL 0.6572 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 Vomicine

Antiplasmodial alkaloids from the stem bark of Strychnos malacoclados.[Pubmed:22193980]

Planta Med. 2012 Mar;78(4):377-82.

From the stem bark of Strychnos malacoclados, one new bisindole alkaloid, 3-hydroxylongicaudatine Y (1), was isolated along with the known alkaloids Vomicine (2), bisnordihydrotoxiferine (3), divarine (4), longicaudatine (5), longicaudatine Y (6), and longicaudatine F (7). All the compounds were tested for their antimalarial activity against the chloroquine-sensitive 3D7 and -resistant W2 strains of Plasmodium falciparum. Longicaudatine was the most active compound with IC(5)(0) values of 0.682 and 0.573 microM, respectively. The activity of compounds 1, 3, 4, 6, and 7 against the two strains ranged from 1.191 to 6.220 microM and 0.573 to 21.848 microM, respectively. Vomicine (2), the only monomer isolated, was inactive. The alkaloids of the longicaudatine-type ( 1, 5-7) were more active than those of the caracurine-type (3- 4). The presence of the ether bridge in the molecule seems to increase the antiplasmodial activity. Compounds 1, 5, and 7 were tested against the WI-38 human fibroblast cell line. Longicaudatine was the most cytotoxic compound with an IC(5)(0) of 2.721 microM. Longicaudatine F was 40-46 times more active against the two strains of P. falciparum than against the human fibroblasts and was thus considered as the more selective alkaloid. The structures of the compounds were determined based on the analysis of their spectral data.

Strychnos nux-vomica seeds: Pharmacognostical standardization, extraction, and antidiabetic activity.[Pubmed:22707864]

J Ayurveda Integr Med. 2012 Apr;3(2):80-4.

BACKGROUND: Strychnos nux-vomica, commonly known as kuchla, contains strychnine and brucine as main constituents. Minor alkaloids present in the seeds are protostrychnine, Vomicine, n-oxystrychnine, pseudostrychnine, isostrychnine, chlorogenic acid, and a glycoside. Seeds are used traditionally to treat diabetes, asthma, aphrodisiac and to improve appetite. OBJECTIVE: The present study was aimed to evaluate the various pharmacognostical characters and antidiabetic activity of S. nux-vomica seed. MATERIALS AND METHODS: Pharmacognostical characters were performed as per the WHO guideline. Extraction was carried out in petroleum ether, chloroform, alcohol, hydroalcoholic, aqueous, and phytochemical constituents present in extracts were detected by different chemical tests. Among these extracts hydroalcoholic, aqueous extracts were evaluated for antidiabetic activity on the basis of extractive yield and phytoconstituents, in alloxan-induced diabetic rats using gliclazide as standard. RESULTS: Various analytical values of S. nux-vomica extract were established. Phytoconstituents present in S. nux-vomica extracts were detected. CONCLUSION: S. nux-vomica extracts show antihyperglycemic activity in experimental animals.

New antimalarial and cytotoxic sungucine derivatives from Strychnos icaja roots.[Pubmed:10821054]

Planta Med. 2000 Apr;66(3):262-9.

Reinvestigation of Strychnos icaja Baillon resulted in the isolation of Vomicine, isostrychnine and of three new sungucine derivatives, named isosungucine (8), 18-hydroxy-sungucine (9) and 18-hydroxy-isosungucine (10). They were identified by detailed spectroscopic methods. The complete 1H- and 13C-NMR study of sungucine was also realized. Some of these compounds were highly active against Plasmodium falciparum in vitro and more particularly against the chloroquine-resistant strain. Compound 10 showed a selective antiplasmodial activity, with > 100-fold greater toxicity towards Plasmodium falciparum, relative to cultured human cancer cells (KB and HeLa lines) or fibroblasts (WI38).

Description

Vomicine, an alkaloid isolated from seeds of S. nux-vomica, shows antidiabetic activity.

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