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Isocucurbitacin B

CAS# 17278-28-3

Isocucurbitacin B

2D Structure

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Isocucurbitacin B

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Chemical Properties of Isocucurbitacin B

Cas No. 17278-28-3 SDF Download SDF
PubChem ID 5352014 Appearance Powder
Formula C32H46O8 M.Wt 558.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(E,6R)-6-[(3S,8S,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-4,4,9,13,14-pentamethyl-2,11-dioxo-3,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
SMILES CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(=O)C(C4(C)C)O)C)C)C)O)O
Standard InChIKey WTBZNVRBNJWSPF-DZEACCAPSA-N
Standard InChI InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19,21-22,25-26,35,38-39H,11,14-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,26-,29+,30-,31+,32+/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 Isocucurbitacin B

The herbs of Cucumis melo

Biological Activity of Isocucurbitacin B

Description1. Isocucurbitacin B has significantly activities against HeLa and HT-29 human cancer cells with IC50 values ranging from 0.93 to 9.73uM.

Isocucurbitacin B Dilution Calculator

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Isocucurbitacin B Molarity Calculator

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Preparing Stock Solutions of Isocucurbitacin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7899 mL 8.9493 mL 17.8987 mL 35.7974 mL 44.7467 mL
5 mM 0.358 mL 1.7899 mL 3.5797 mL 7.1595 mL 8.9493 mL
10 mM 0.179 mL 0.8949 mL 1.7899 mL 3.5797 mL 4.4747 mL
50 mM 0.0358 mL 0.179 mL 0.358 mL 0.7159 mL 0.8949 mL
100 mM 0.0179 mL 0.0895 mL 0.179 mL 0.358 mL 0.4475 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 Isocucurbitacin B

Bioassay-guided isolation and identification of cytotoxic compounds from Bolbostemma paniculatum.[Pubmed:25882313]

J Ethnopharmacol. 2015 Jul 1;169:18-23.

ETHNOPHARMACOLOGICAL RELEVANCE: Bolbostemma paniculatum (Maxim.) Franquet (B. paniculatum), also named "Tu-bei-mu" in Chinese folk medicines, has been described in application for the treatment of tumors, warts, inflammation and toxication in traditional Chinese medicinal books. The major constituents in B. paniculatum are triterpenoid saponins, which have been proved to possess dramatically cytotoxic activity and antivirus activity. The aim of this study is to isolate and identify the active triterpenoid saponin from the bulb of B. paniculatum by a bioassay-guided method. MATERIALS AND METHODS: Four cucurbitacine triterpenoid sapogenins and 11 triterpenoid saponins were isolated from the active EtOAc and n-BuOH extract of B. paniculatum by using bioassay-guided screening. Their structures were elucidated based on the spectroscopic methods and compared with published data. Cytotoxic activities of isolated compounds were determined by MTT assay. RESULTS: Four cucurbitacine triterpenoid sapogenins, Isocucurbitacin B(1), 23,24-dihydroIsocucurbitacin B(2), cucurbitacin E(3), 23,24-dihydrocucurbitacin E(4), and 11 triterpenoid saponins, tubeimosideI(5), tubeimoside III(6), tubeimoside V(7), dexylosyltubeimoside III(8), lobatoside C(9), tubeimoside A(10), tumeimoside B(11), lobatoside A(12), tubeimoside C(13), tubeimoside IV(14), 7beta,18,20,26-tetrahydroxy-(20S)-dammar-24E-en-3-O-alpha-L-(4-acetyl)arabinopyra nosyl-(1-->2)-beta-D-glucopyranoside(15) were isolated from the active EtOAc and n-BuOH extracts. Of them, compounds 2, 4, 9 and 12 were firstly isolated from the Bolbostemma genus. MTT assay revealed that compounds 1, 3 and 4 had significantly activities against HeLa and HT-29 human cancer cells with IC50 values ranging from 0.93 to 9.73muM. It is worth mentioning that compound 4s activities against the two cell lines are 12- and 8-fold that of the positive control drug (5-Fu). Whereas, the cyclic bisdesmosides 5-9 exerted significantly activities on BGC-823, HeLa, HT-29 and MCF-7 cancer cells with IC50 values ranging from 1.30 to 15.64muM. And 6s activities against the four cell lines are 6-, 3-, 10- and 16-fold that of 5-Fu and 8s activities against the four cell lines are 5-, 3-, 14- and 9-fold that of 5-Fu. CONCLUSION: The cytotoxic activity of the bulbs of B. paniculatum is mainly ascribable to cucurbitacine triterpenoid sapogenins (1-4) and the cyclic bisdesmosides (5-9). The cyclic bisdesmosides are the main anti-cancer active compounds of B. paniculatum. The above results provide scientific evidence to support, to some extent, the ethnomedicinal use of B. paniculatum as anticancer remedies in traditional Chinese medicine.

Description

Isocucurbitacin B is a potent cytotoxic compound isolated from Helicteres rswa L. (Sterculiaceae). Isocucurbitacin B possesses anti-tumor acticity.

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