Vasicinol

CAS# 5081-51-6

Vasicinol

Catalog No. BCN5812----Order now to get a substantial discount!

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Quality Control of Vasicinol

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Chemical structure

Vasicinol

3D structure

Chemical Properties of Vasicinol

Cas No. 5081-51-6 SDF Download SDF
PubChem ID 442934 Appearance Powder
Formula C11H12N2O2 M.Wt 204.2
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline-3,7-diol
SMILES C1CN2CC3=C(C=CC(=C3)O)N=C2C1O
Standard InChIKey WEFMOGRHGUPGMA-JTQLQIEISA-N
Standard InChI InChI=1S/C11H12N2O2/c14-8-1-2-9-7(5-8)6-13-4-3-10(15)11(13)12-9/h1-2,5,10,14-15H,3-4,6H2/t10-/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 Vasicinol

The leaves of Adhatoda vasica Nees

Biological Activity of Vasicinol

Description1. Vasicinol shows a high sucrase inhibitory activity, and the IC50 values was 250 μM.vasicinol could be an useful treatment for metabolic disorders.
2. Vasicinol and vasicinone severe antifertility effects are exhibited by vasicinol against Dysdercus skoenigii and Tribolium castaneum due to blocking of oocytes in the oviduct.

Vasicinol Dilution Calculator

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Vasicinol Molarity Calculator

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Preparing Stock Solutions of Vasicinol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.8972 mL 24.4858 mL 48.9716 mL 97.9432 mL 122.429 mL
5 mM 0.9794 mL 4.8972 mL 9.7943 mL 19.5886 mL 24.4858 mL
10 mM 0.4897 mL 2.4486 mL 4.8972 mL 9.7943 mL 12.2429 mL
50 mM 0.0979 mL 0.4897 mL 0.9794 mL 1.9589 mL 2.4486 mL
100 mM 0.049 mL 0.2449 mL 0.4897 mL 0.9794 mL 1.2243 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 Vasicinol

In vitro and in vivo metabolism and inhibitory activities of vasicine, a potent acetylcholinesterase and butyrylcholinesterase inhibitor.[Pubmed:25849329]

PLoS One. 2015 Apr 7;10(4):e0122366.

Vasicine (VAS), a potential natural cholinesterase inhibitor, exhibited promising anticholinesterase activity in preclinical models and has been in development for treatment of Alzheimer's disease. This study systematically investigated the in vitro and in vivo metabolism of VAS in rat using ultra performance liquid chromatography combined with electrospray ionization quadrupole time-of-flight mass spectrometry. A total of 72 metabolites were found based on a detailed analysis of their 1H- NMR and 13C NMR data. Six key metabolites were isolated from rat urine and elucidated as vasicinone, Vasicinol, Vasicinolone, 1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-3-yl hydrogen sulfate, 9-oxo-1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-3-yl hydrogen sulfate, and 1,2,3,9-tetrahydropyrrolo [2,1-b] quinazolin-3-beta-D-glucuronide. The metabolic pathway of VAS in vivo and in vitro mainly involved monohydroxylation, dihydroxylation, trihydroxylation, oxidation, desaturation, sulfation, and glucuronidation. The main metabolic soft spots in the chemical structure of VAS were the 3-hydroxyl group and the C-9 site. All 72 metabolites were found in the urine sample, and 15, 25, 45, 18, and 11 metabolites were identified from rat feces, plasma, bile, rat liver microsomes, and rat primary hepatocyte incubations, respectively. Results indicated that renal clearance was the major excretion pathway of VAS. The acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of VAS and its main metabolites were also evaluated. The results indicated that although most metabolites maintained potential inhibitory activity against AChE and BChE, but weaker than that of VAS. VAS undergoes metabolic inactivation process in vivo in respect to cholinesterase inhibitory activity.

3-Hydr-oxy-1,2,3,9-tetra-hydro-pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro-chloride dihydrate from Peganum harmala L.[Pubmed:21582144]

Acta Crystallogr Sect E Struct Rep Online. 2009 Feb 6;65(Pt 3):o474-5.

The title compound, C(11)H(13)N(2)O(+).Cl(-).2H(2)O, the dihydrate of (+)-Vasicinol hydro-chloride, is a pyrrolidinoquinazoline alkaloid. It was isolated from the ethyl acetate fraction of the leaves of Peganum harmala L. The pyrrolidine ring has an envelope conformation with the C atom at position 2 acting as the flap and the C atom at position 3, carrying the hydroxyl substituent, has an S configuration. The absolute configuration was determined as a result of the anomalous scattering of the Cl atom. In the crystal structure, mol-ecules stack along the a axis, connected to one another via inter-molecular O-Hcdots, three dots, centeredCl and N-Hcdots, three dots, centeredCl hydrogen bonds, forming approximately triangular-shaped R(2) (1)(7) rings, and O-Hcdots, three dots, centeredCl and O-Hcdots, three dots, centeredO hydrogen bonds, forming penta-gonal-shaped R(5) (4)(10) rings. The overall effect is a ribbon-like arrangement running parallel to the a axis.

Inhibitory effect on alpha-glucosidase by Adhatoda vasica Nees.[Pubmed:26065759]

Food Chem. 2008 Jun 1;108(3):965-72.

Methanolic extracts from the medicinal parts of 40 traditional Chinese herbs were tested in screening experiments for rat intestinal alpha-glucosidase. The methanolic extract from the leaves of Adhatoda vasica Nees (Acanthaceae) showed the highest sucrase inhibitory activity with sucrose as a substrate. Enzyme assay-guided fractionation of this extract afforded vasicine (1) and Vasicinol (2), and the structures of these compounds were elucidated on the basis of MS and NMR analysis. Compounds 1 and 2 showed a high sucrase inhibitory activity, and the IC50 values were 125muM and 250muM, respectively. Both 1 and 2 were shown to be reversible inhibitors of sucrase. Kinetic data revealed that compounds 1 and 2 inhibited sucrose-hydrolysing activity of rat intestinal alpha-glucosidase competitively with Ki values of 82muM and 183muM, respectively. This is the first report on the mammalian alpha-glucosidase inhibition of A. vasica and the inhibitory effect on sucrase by 1 and 2 from this herb species. These results suggest a use of the extract of A. vasica as an antidiabetic agent and show a possibility that compounds 1 and 2 could be an useful treatment for metabolic disorders.

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