| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
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Purity: ≥98%
Cucurbitacin B, a naturally occurring triterpene analog and a potential cancer chemotherapeutic agent, could repress cancer cell progression. Cucurbitacin B is a plant-derived triterpene that has the classic four-ring structure of mammalian steroids. Cucurbitacin B suppresses metastasis mediated by reactive oxygen species (ROS) via focal adhesion kinase (FAK) in breast cancer MDA-MB-231 cells. Cucurbitacin B induces inhibitory effects via CIP2A/PP2A/Akt pathway in glioblastoma multiforme. Cucurbitacin B acts a potential insect growth regulator by antagonizing 20-hydroxyecdysone activity.
| ln Vitro |
Cucurbitacin B slows cell growth in CCA cell lines and prevents the cell purifying cycle process in the G2/M phase at concentrations up to 40 μM, lasting 12–48 hours [2]. In BY4741 yeast cells, cucurbitacin B (0.1, 0.3, and 1 μM) decreased the levels of reactive oxygen species (ROS) and malondialdehyde (MDA) while increasing the levels of SOD-1 and total superoxide dismutase (T-SOD) [3].
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| ln Vivo |
Cucurbitacin B (5 mg/kg, abdominal, 10 days) prevents gunitis caused by gold carrageenan [4]. Cucurbitacin B (20–50 mg/kg, intraperitoneal injection, 28 days) can improve memory function, prevent STZ-ICV toxicity to neuronal scaffolds, and lessen AD-like symptoms [5].
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| Cell Assay |
Cell Viability Assay [2]
Cell Types: CCA Cell Line Tested Concentrations: 0.1, 1 0.5, 1,5, 10, 20, 40 μM Incubation Duration: 24 and 48 hrs (hours) Experimental Results: Cell viability diminished in a dose-dependent and time-dependent manner , IC50 value is 13: 44 μM at 24 hrs (hours) and 1.55 at 48 hrs (hours). Cell cycle analysis[2] Cell Types: CCA Cell Line Tested Concentrations: 0.1, 1, 10 μM Incubation Duration: 24 hrs (hours) Experimental Results: Cell cycle progression is arrested in G2/M phase. Western Blot Analysis[2] Cell Types: CCA Cell line Tested Concentrations: 0.1, 1 0.5, 1,5, 10, 20, 40 μM Incubation Duration: 12 and 24 h Experimental Results: The expression of Cyclin A, Cyclin D1, Cdc25A diminished but increased reached the level of p21. |
| Animal Protocol |
Animal/Disease Models: Carrageenan-induced prostatic inflammation in rats [4]
Doses: 5mg/kg/day, 10 days Route of Administration: Oral Experimental Results:Reduce TNF-α, IL-1b, COX-2 and iNOS levels. Animal/Disease Models: STZ-ICV AD-like dementia rat prototype [5] Doses: 20, 50mg/kg/day for 28 days Route of Administration: intraperitoneal (ip) injection Experimental Results: TNF-α, IL-1β, MPO, iNOS , acetylcholinesterase and glutamate levels, but not gamma-aminobutyric acid. Increased density of viable neurons in rat cortex and hippocampus. |
| References |
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| Additional Infomation |
Cucurbitacin B is a cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23; a hydroxy function at C-25 is acetylated. It is a cucurbitacin, a secondary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It derives from a hydride of a lanostane.
Cucurbitacin B has been reported in Trichosanthes hupehensis, Trichosanthes tricuspidata, and other organisms with data available. Mechanism of Action THE BINDING OF CUCURBITACINS TO GLUCOCORTICOID RECEPTORS IN HELA CELL-FREE SYSTEMS & IN INTACT CELLS WAS STUDIED BY COMPETITION WITH (3)H-CORTISOL. CUCURBITACINS DIMINISHED THE (3)H-CORTISOL BINDING. THE DIFFERENCE IN BINDING AFFINITY AT TWO TEMPERATURES SUGGEST THAT CUCURBITACINS ARE METABOLIZED UNDER PHYSIOLOGICAL CONDITIONS. A LINEAR CORRELATION WAS OBSERVED BETWEEN LOGARITHMS OF RELATIVE BINDING AFFINITIES & OF CYTOTOXIC ACTIVITIES OF CUCURBITACINS. HENCE, THE CUCURBITACIN BINDING TO GLUCOCORTICOID RECEPTORS SEEMS TO BE A NECESSARY STEP FOR CYTOTOXIC ACTION OF THESE COMPD. EIGHT BIOLOGICALLY ACTIVE CUCURBITACINS ISOLATED FROM ROOTS OF BRYONIA ALBA, INCLUDING CUCURBITACIN B, WERE CYTOTOXIC IN TISSUE CULTURES OF KB & HELA CELLS. CUCURBITACIN B WAS EFFECTIVE ON TRANSPLANTABLE SARCOMA 180 & EHRLICH ASCITES CARCINOMA IN MICE. IN RATS WITH IM WALKER CARCINOSARCOMA 256 & IN MICE WITH LEWIS LUNG CARCINOMA, ADMIN OF CUCURBITACIN B 0.8-1.6 MG/KG INHIBITED TUMOR DEVELOPMENT BUT THE LOW MARGIN BETWEEN ACTIVE & TOXIC DOSES RENDERED THE MATERIAL UNPROMISING AS A THERAPEUTIC AGENT. |
| Molecular Formula |
C32H46O8
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|---|---|
| Molecular Weight |
558.7029
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| Exact Mass |
558.319
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| CAS # |
6199-67-3
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| Related CAS # |
Cucurbitacin E;18444-66-1;Cucurbitacin I;2222-07-3
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| PubChem CID |
5281316
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
699.3±55.0 °C at 760 mmHg
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| Melting Point |
184-186ºC
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| Flash Point |
218.8±25.0 °C
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| Vapour Pressure |
0.0±5.0 mmHg at 25°C
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| Index of Refraction |
1.568
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| LogP |
2.31
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
40
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| Complexity |
1210
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| Defined Atom Stereocenter Count |
9
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| SMILES |
CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O)C)C)C)O)O
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| InChi Key |
IXQKXEUSCPEQRD-DKRGWESNSA-N
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| InChi Code |
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/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1
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| Chemical Name |
(R,E)-6-((2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
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| Synonyms |
Cucurbitacin B; Cuc B; NSC 49451; NSC 144154.
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~178.99 mM)
H2O : ~1 mg/mL (~1.79 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.47 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.47 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7899 mL | 8.9493 mL | 17.8987 mL | |
| 5 mM | 0.3580 mL | 1.7899 mL | 3.5797 mL | |
| 10 mM | 0.1790 mL | 0.8949 mL | 1.7899 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
 The proliferative inhibition effects of CuB on human lung cancer A549 cells.
Effect of CuB on the activity of caspase-3 and -9 in CuB-induced apoptosis.Mol Med Rep. 2014 Dec;10(6):2905-11. |
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 Flow cytometric cell cycle analysis.
Flow cytometric quantification of apoptotic cells.
CuB induces disruption of ΔΨm.Mol Med Rep. 2014 Dec;10(6):2905-11. |
 Cell apoptosis observed by Hoechst 33258 staining.
Transmission electron micrographs of A549 control cells and cells treated with CuB (1.0 μmol/l) for 24 h.
CuB induces the release of mitochondrial cytochrome C.Mol Med Rep. 2014 Dec;10(6):2905-11. |
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