Tabersonine

CAS# 4429-63-4

Tabersonine

Catalog No. BCN5496----Order now to get a substantial discount!

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Quality Control of Tabersonine

Number of papers citing our products

Chemical structure

Tabersonine

3D structure

Chemical Properties of Tabersonine

Cas No. 4429-63-4 SDF Download SDF
PubChem ID 20485 Appearance Yellow powder
Formula C21H24N2O2 M.Wt 336.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CCC12CC(=C3C4(C1N(CC4)CC=C2)C5=CC=CC=C5N3)C(=O)OC
Standard InChIKey FNGGIPWAZSFKCN-ACRUOGEOSA-N
Standard InChI InChI=1S/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/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 Tabersonine

The root bark of Voacanga africana Stapf

Biological Activity of Tabersonine

Description1. Tabersonine is a precursor for vincristine used in cancer chemotherapy, the biocompatibility and small size essential for permeating the blood-brain barrier make it a potential therapeutic drug candidate for treating AD.
TargetsBeta Amyloid | P450 (e.g. CYP17)

Tabersonine Dilution Calculator

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Tabersonine Molarity Calculator

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Preparing Stock Solutions of Tabersonine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9727 mL 14.8633 mL 29.7265 mL 59.453 mL 74.3163 mL
5 mM 0.5945 mL 2.9727 mL 5.9453 mL 11.8906 mL 14.8633 mL
10 mM 0.2973 mL 1.4863 mL 2.9727 mL 5.9453 mL 7.4316 mL
50 mM 0.0595 mL 0.2973 mL 0.5945 mL 1.1891 mL 1.4863 mL
100 mM 0.0297 mL 0.1486 mL 0.2973 mL 0.5945 mL 0.7432 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 Tabersonine

Tabersonine inhibits amyloid fibril formation and cytotoxicity of Abeta(1-42).[Pubmed:25874995]

ACS Chem Neurosci. 2015 Jun 17;6(6):879-88.

The misfolding and aggregation of amyloid beta (Abeta) peptides into amyloid fibrils are key events in the amyloid cascade hypothesis for the etiology of Alzheimer's disease (AD). Using thioflavin-T (ThT) fluorescence assay, atomic force microscopy, circular dichroism, size exclusion chromatography, surface plasmon resonance (SPR), and cytotoxicity tests, we demonstrate that Tabersonine, an ingredient extracted from the bean of Voacanga africana, disrupts Abeta(1-42) aggregation and ameliorates Abeta aggregate-induced cytotoxicity. A small amount of Tabersonine (e.g., 10 muM) can effectively inhibit the formation of Abeta(1-42) (e.g., 80 muM) fibrils or convert mature fibrils into largely innocuous amorphous aggregates. SPR results indicate that Tabersonine binds to Abeta(1-42) oligomers in a dose-dependent way. Molecular dynamics (MD) simulations further confirm that Tabersonine can bind to oligomers such as the pentamer of Abeta(1-42). Tabersonine preferentially interact with the beta-sheet grooves of Abeta(1-42) containing aromatic and hydrophobic residues. The various binding sites and modes explain the diverse inhibitory effects of Tabersonine on Abeta aggregation. Given that Tabersonine is a natural product and a precursor for vincristine used in cancer chemotherapy, the biocompatibility and small size essential for permeating the blood-brain barrier make it a potential therapeutic drug candidate for treating AD.

Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast.[Pubmed:25918424]

Proc Natl Acad Sci U S A. 2015 May 12;112(19):6224-9.

Antitumor substances related to vinblastine and vincristine are exclusively found in the Catharanthus roseus (Madagascar periwinkle), a member of the Apocynaceae plant family, and continue to be extensively used in cancer chemotherapy. Although in high demand, these valuable compounds only accumulate in trace amounts in C. roseus leaves. Vinblastine and vincristine are condensed from the monoterpenoid indole alkaloid (MIA) precursors catharanthine and vindoline. Although catharanthine biosynthesis remains poorly characterized, the biosynthesis of vindoline from the MIA precursor Tabersonine is well understood at the molecular and biochemical levels. This study uses virus-induced gene silencing (VIGS) to identify a cytochrome P450 [CYP71D1V2; Tabersonine 3-oxygenase (T3O)] and an alcohol dehydrogenase [ADHL1; Tabersonine 3-reductase (T3R)] as candidate genes involved in the conversion of Tabersonine or 16-methoxyTabersonine to 3-hydroxy-2,3-dihydroTabersonine or 3-hydroxy-16-methoxy-2,3-dihydroTabersonine, which are intermediates in the vindorosine and vindoline pathways, respectively. Biochemical assays with recombinant enzymes confirm that product formation is only possible by the coupled action of T3O and T3R, as the reaction product of T3O is an epoxide that is not used as a substrate by T3R. The T3O and T3R transcripts were identified in a C. roseus database representing genes preferentially expressed in leaf epidermis and suggest that the subsequent reaction products are transported from the leaf epidermis to specialized leaf mesophyll idioblast and laticifer cells to complete the biosynthesis of these MIAs. With these two genes, the complete seven-gene pathway was engineered in yeast to produce vindoline from Tabersonine.

Jasmonate-induced epoxidation of tabersonine by a cytochrome P-450 in hairy root cultures of Catharanthus roseus.[Pubmed:12943756]

Phytochemistry. 2003 Sep;64(2):401-9.

Methyl jasmonate, a chemical inducer of secondary metabolism, was shown to promote Tabersonine 2 biosynthesis in hairy root cultures of Catharanthus roseus. Tabersonine 6,7-epoxidase activity was detected in total protein extract of jasmonate-induced hairy root cultures using labeled 14C-Tabersonine 2. This enzyme converted Tabersonine 2 to lochnericine 3 by selective epoxidation at positions 6 and 7 via a reaction dependent on NADPH and molecular oxygen. Carbon monoxide, clotrimazole, miconazole, and cytochrome C were shown to be strong inhibitors of the enzyme. The activity was found in microsomes, indicating that Tabersonine 6,7-epoxidase was a cytochrome P-450-dependent monooxygenase.

Description

Tabersonine is an indole alkaloid mainly isolated from Catharanthus roseus. Tabersonine disrupts Aβ(1-42) aggregation and ameliorates Aβ aggregate-induced cytotoxicity. Tabersonine has anti-inflammatory activities and acts as a potential therapeutic candidate for the treatment of ALI/ARDS.

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