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Taccalonolide B

CAS# 108885-69-4

Taccalonolide B

Catalog No. BCN2743----Order now to get a substantial discount!

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Quality Control of Taccalonolide B

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Chemical structure

Taccalonolide B

3D structure

Chemical Properties of Taccalonolide B

Cas No. 108885-69-4 SDF Download SDF
PubChem ID 56662029 Appearance Powder
Formula C34H44O13 M.Wt 660.71
Type of Compound Steroids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC1C=C2C(C3C1C4(C(C3O)C5C(C(C4OC(=O)C)OC(=O)C)C6(C(CC7C(C6OC(=O)C)O7)C(=O)C5O)C)C)(C(C(=O)O2)(C)O)C
Standard InChIKey FFQOXBQSZPYHSA-MPOUNFKCSA-N
Standard InChI InChI=1S/C34H44O13/c1-11-9-17-33(7,34(8,42)30(41)47-17)22-19(11)32(6)20(25(22)40)18-21(27(43-12(2)35)29(32)45-14(4)37)31(5)15(23(38)24(18)39)10-16-26(46-16)28(31)44-13(3)36/h9,11,15-16,18-22,24-29,39-40,42H,10H2,1-8H3/t11-,15-,16+,18+,19+,20-,21-,22+,24-,25-,26+,27+,28+,29+,31+,32-,33+,34-/m1/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 Taccalonolide B

The rhizomes of Schizocapsa plantaginea Hance

Biological Activity of Taccalonolide B

DescriptionTaccalonolide B displays microtubule stabilizing activity.Several taccalonolides have in vitro antitrypanosomal activity against Trypanosoma brucei brucei and EC50 values for the isolated compounds were from 0.79 ug/mL.
TargetsAntifection
In vitro

Potent Taccalonolides, AF and AJ, Inform Significant Structure–Activity Relationships and Tubulin as the Binding Site of These Microtubule Stabilizers[Reference: WebLink]

J. Am. Chem. Soc., 2011, 133 (47), pp 19064–19067

The taccalonolides are a class of microtubule stabilizing agents isolated from plants of the genus Tacca. In efforts to define their structure–activity relationships, we isolated five new taccalonolides, AC–AF and H2, from one fraction of an ethanol extract of Tacca plantaginea.
METHODS AND RESULTS:
The structures were elucidated using a combination of spectroscopic methods, including 1D and 2D NMR and HR-ESI-MS. Taccalonolide AJ, an epoxidation product of Taccalonolide B, was generated by semisynthesis. Five of these taccalonolides demonstrated cellular microtubule-stabilizing activities and antiproliferative actions against cancer cells, with taccalonolide AJ exhibiting the highest potency with an IC50 value of 4.2 nM. The range of potencies of these compounds, from 4.2 nM to >50 μM, for the first time provides the opportunity to identify specific structural moieties crucial for potent biological activities as well as those that impede optimal cellular effects. In mechanistic assays, taccalonolides AF and AJ stimulated the polymerization of purified tubulin, an activity that had not previously been observed for taccalonolides A and B, providing the first evidence that this class of microtubule stabilizers can interact directly with tubulin/microtubules. Taccalonolides AF and AJ were able to enhance tubulin polymerization to the same extent as paclitaxel but exhibited a distinct kinetic profile, suggesting a distinct binding mode or the possibility of a new binding site.
CONCLUSIONS:
The potencies of taccalonolides AF and AJ and their direct interaction with tubulin, together with the previous excellent in vivo antitumor activity of this class, reveal the potential of the taccalonolides as new anticancer agents.

Taccalonolide B Dilution Calculator

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Taccalonolide B Molarity Calculator

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Preparing Stock Solutions of Taccalonolide B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.5135 mL 7.5676 mL 15.1352 mL 30.2705 mL 37.8381 mL
5 mM 0.3027 mL 1.5135 mL 3.027 mL 6.0541 mL 7.5676 mL
10 mM 0.1514 mL 0.7568 mL 1.5135 mL 3.027 mL 3.7838 mL
50 mM 0.0303 mL 0.1514 mL 0.3027 mL 0.6054 mL 0.7568 mL
100 mM 0.0151 mL 0.0757 mL 0.1514 mL 0.3027 mL 0.3784 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 Taccalonolide B

Hydrolysis reactions of the taccalonolides reveal structure-activity relationships.[Pubmed:23855953]

J Nat Prod. 2013 Jul 26;76(7):1369-75.

The taccalonolides are microtubule stabilizers isolated from plants of the genus Tacca that show potent in vivo antitumor activity and the ability to overcome multiple mechanisms of drug resistance. The most potent taccalonolide identified to date, AJ, is a semisynthetic product generated from the major plant metabolite taccalonolide A in a two-step reaction. The first step involves hydrolysis of taccalonolide A to generate Taccalonolide B, and then this product is oxidized to generate an epoxide group at C-22-C-23. To generate sufficient taccalonolide AJ for in vivo antitumor efficacy studies, the hydrolysis conditions for the conversion of taccalonolide A to B were optimized. During purification of the hydrolysis products, we identified the new taccalonolide AO (1) along with taccalonolide I. When the same hydrolysis reaction was performed on a taccalonolide E-enriched fraction, four new taccalonolides, assigned as AK, AL, AM, and AN (2-5), were obtained in addition to the expected product taccalonolide N. Biological assays were performed on each of the purified taccalonolides, which allowed for increased refinement of the structure-activity relationship of this class of compounds.

Potent taccalonolides, AF and AJ, inform significant structure-activity relationships and tubulin as the binding site of these microtubule stabilizers.[Pubmed:22040100]

J Am Chem Soc. 2011 Nov 30;133(47):19064-7.

The taccalonolides are a class of microtubule stabilizing agents isolated from plants of the genus Tacca. In efforts to define their structure-activity relationships, we isolated five new taccalonolides, AC-AF and H2, from one fraction of an ethanol extract of Tacca plantaginea. The structures were elucidated using a combination of spectroscopic methods, including 1D and 2D NMR and HR-ESI-MS. Taccalonolide AJ, an epoxidation product of Taccalonolide B, was generated by semisynthesis. Five of these taccalonolides demonstrated cellular microtubule-stabilizing activities and antiproliferative actions against cancer cells, with taccalonolide AJ exhibiting the highest potency with an IC(50) value of 4.2 nM. The range of potencies of these compounds, from 4.2 nM to >50 muM, for the first time provides the opportunity to identify specific structural moieties crucial for potent biological activities as well as those that impede optimal cellular effects. In mechanistic assays, taccalonolides AF and AJ stimulated the polymerization of purified tubulin, an activity that had not previously been observed for taccalonolides A and B, providing the first evidence that this class of microtubule stabilizers can interact directly with tubulin/microtubules. Taccalonolides AF and AJ were able to enhance tubulin polymerization to the same extent as paclitaxel but exhibited a distinct kinetic profile, suggesting a distinct binding mode or the possibility of a new binding site. The potencies of taccalonolides AF and AJ and their direct interaction with tubulin, together with the previous excellent in vivo antitumor activity of this class, reveal the potential of the taccalonolides as new anticancer agents.

Description

Taccalonolide B is microtubule stabilizer isolated from Tacca plantaginea, with antitumor activity. Taccalonolide B is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug-resistance protein (MRP7). Taccalonolide B inhibits growth of SK-OV-3 cells with an IC50 of 208 nM.

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