Cucurbitacin B

Alias: Cucurbitacin B; Cuc B; NSC 49451; NSC 144154.
Cat No.:V4970 Purity: ≥98%
Cucurbitacin B, a naturally occurring triterpene analog and a potential cancer chemotherapeutic agent, could repress cancer cell progression.
Cucurbitacin B Chemical Structure CAS No.: 6199-67-3
Product category: Integrin
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Cucurbitacin B:

  • Cucurbitacin E
  • Cucurbitacin I
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

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.

Biological Activity I Assay Protocols (From Reference)
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].
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].
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
[1]. Dai S, , et al. Cucurbitacin B: A review of its pharmacology, toxicity, and pharmacokinetics. Pharmacol Res. 2023;187:106587.
[2]. Klungsaeng, et al. Targeted Modulation of FAK/PI3K/PDK1/AKT and FAK/p53 Pathways by Cucurbitacin B for the Antiproliferation Effect Against Human Cholangiocarcinoma Cells. Am J Chin Med. 2020;48(6):1475-1489.
[3]. Lin Y, et al. Cucurbitacin B Exerts Antiaging Effects in Yeast by Regulating Autophagy and Oxidative Stress. Oxid Med Cell Longev. 2019;2019:4517091.
[4]. Aljohani OS. Phytochemical evaluation of Cucumis prophetarum: protective effects against carrageenan-induced prostatitis in rats. Drug Chem Toxicol. 2022;45(4):1461-1469.
[5]. Liu Z, Kumar M, Kabra A. Cucurbitacin B exerts neuroprotection in a murine Alzheimer's disease model by modulating oxidative stress, inflammation, and neurotransmitter levels. Front Biosci (Landmark Ed). 2022;27(2):71.
[6]. Shang Y, et al. Cucurbitacin-B inhibits neuroblastoma cell proliferation through up-regulation of PTEN. Eur Rev Med Pharmacol Sci. 2014;18(21):3297-303.
[7]. Zhang M, et al. Cucurbitacin B inhibits proliferation and induces apoptosis via STAT3 pathway inhibition in A549 lung cancer cells. Mol Med Rep. 2014 Dec;10(6):2905-11.
[8]. Guo J, et al. Cucurbitacin B induced ATM-mediated DNA damage causes G2/M cell cycle arrest in a ROS-dependent manner. PLoS One. 2014 Feb 4;9(2):e88140.
[9]. Gupta P, et al. Inhibition of Integrin-HER2 signaling by Cucurbitacin B leads to in vitro and in vivo breast tumor growth suppression. Oncotarget. 2014 Apr 15;5(7):1812-28.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C32H46O8
Molecular Weight
558.7029
CAS #
6199-67-3
Related CAS #
Cucurbitacin E;18444-66-1;Cucurbitacin I;2222-07-3
SMILES
O[C@@H]1C(C(C)(C)C2=CC[C@]([C@@](C[C@@H](O)[C@]3([H])[C@](O)(C)C(/C=C/C(C)(C)OC(C)=O)=O)(C)[C@]3(C)CC4=O)([H])[C@]4(C)[C@]2([H])C1)=O
InChi Key
IXQKXEUSCPEQRD-DKRGWESNSA-N
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
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
Synonyms
Cucurbitacin B; Cuc B; NSC 49451; NSC 144154.
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)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~178.99 mM)
H2O : ~1 mg/mL (~1.79 mM)
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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

Biological Data
  • Cucurbitacin B


    The proliferative inhibition effects of CuB on human lung cancer A549 cells.

    Cucurbitacin B

    Effect of CuB on the activity of caspase-3 and -9 in CuB-induced apoptosis.Mol Med Rep. 2014 Dec;10(6):2905-11.

  • Cucurbitacin B


    Flow cytometric cell cycle analysis.

    Cucurbitacin B

    Flow cytometric quantification of apoptotic cells.

    Cucurbitacin B

    CuB induces disruption of ΔΨm.Mol Med Rep. 2014 Dec;10(6):2905-11.

  • Cucurbitacin B


    Cell apoptosis observed by Hoechst 33258 staining.

    Cucurbitacin B

    Transmission electron micrographs of A549 control cells and cells treated with CuB (1.0 μmol/l) for 24 h.

    Cucurbitacin B

    CuB induces the release of mitochondrial cytochrome C.Mol Med Rep. 2014 Dec;10(6):2905-11.

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