A natural triterpene
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Cucurbitacin B

Item No. 14820

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2β,9β,10α,16α,23E)-25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-5,23-diene-3,11,22-trione
CAS Number
6199-67-3
Synonyms
  • NSC 49451
  • NSC 144154
Molecular Formula
C32H46O8
Formula Weight
558.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleDichloromethane: SolubleEthyl Acetate: Soluble
λmax
226 nm
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 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
InChi Key
IXQKXEUSCPEQRD-DKRGWESNSA-N
Origin
Plant/Cucumis melo L.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $157

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    10 mg

    $293

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    25 mg

    $583

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    Product Description

    Cucurbitacin B is a plant-derived triterpene that has the classic four-ring structure of mammalian steroids. It has diverse effects on mammalian cells, most notably inducing cell cycle arrest or apoptosis in a range of cancer cell lines.1,2,3 Cucurbitacin B inhibits the growth of several breast cancer cell lines (IC50s = 18-50 nM).4 It suppresses the growth of tumors developed from MDA-MB-231 and 4T-1 breast cancer cells in mice.4 Cucurbitacin B blocks the inflammatory response of macrophages treated with lipopolysaccharide.5 In Drosophila, it serves as an ecdysteroid receptor antagonist (Kd = 5 µM).6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Duangmano, S., Sae-lim, P., Suksamrarn, A., et al. Cucurbitacin B inhibits human breast cancer cell proliferation through disruption of microtubule polymerization and nucleophosmin/B23 translocation. BMC Complement. Altern. Med. 12, 185 (2012).

    2. Dakeng, S., Duangmano, S., Jiratchariyakul, W., et al. Inhibition of Wnt signaling by cucurbitacin B in breast cancer cells: Reduction of Wnt associated proteins and reduced translocation of falectin-3-mediated ß-catenin to the nucleus. J. Cell. Biochem. 113(1), 49-60 (2012).

    3. Zhang, M., Bian, Z.G., Zhang, Y., et al. Cucurbitacin B inhibits proliferation and induces apoptosis via STAT3 pathway inhibition in A549 lung cancer cells. Mol. Med. Rep. 10(6), 2905-2911 (2014).

    4. Gupta, P., and Srivastava, S.K. Inhibition of Integrin-HER2 signaling by Cucurbitacin B leads to in vitro and in vivo breast tumor growth suppression. Oncotarget 5(7), 1812-1828 (2014).

    5. Kim, M., Park, S.Y., Jin, M.L., et al. Cucurbitacin B inhibits immunomodulatory function and the inflammatory response in macrophages. Immunopharmacol. Immunotoxicol. 37(5), 473-480 (2015).

    6. Dinan, L., Whiting, P., Girault, J.P., et al. Cucurbitacins are insect steroid hormone antagonists acting at the ecdysteroid recepto. Biochem. J. 327( Pt 3)(Pt 3), 643-650 (1997).