Cucurbitacin B

Specifications / Handling

More Information
Product Details
Synonyms	Cuc B; 1,2-Dihydro-α-elaterin; Amarine; NSC 49451; NSC 144154
Product Type	Chemical
Properties
Formula	C₃₂H₄₆O₈
MW	558.7
CAS	6199-67-3
Source/Host Chemicals	Isolated from Cucumis melo L.
Purity Chemicals	≥98% (HPLC)
Appearance	Off-white powder.
Solubility	Soluble in DMSO.
Identity	Determined by ¹H-NMR.
InChi Key	IXQKXEUSCPEQRD-DKRGWESNSA-N
Smiles	[H][C@@]1([C@H](O)C[C@@]2(C)[C@]3([H])CC=C4[C@@]([H])(C[C@H](O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C)[C@@](C)(O)C(=O)\C=C\C(C)(C)OC(C)=O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Microtubule polymerization inhibitor. Disrupts F-actin and induces nucleophosmin/B23 translocation.
Immunomodulator with antimicrobial, anti-inflammatory and antitumorigenic properties.
Induces apoptosis, autophagy and cell cycle arrest at G2/M phase in a range of cancer cell lines.
Shown to inhibit STAT 3 phosphorylation and expression levels and blocks JAK2 activity, as well as the transcriptional activity of HIF1α and NF-κB.
Antioxidant.
Serves as an ecdysteroid receptor antagonist in Drosophila.

Product References

Cucurbitacins are insect steroid hormone antagonists acting at the ecdysteroid receptor: L. Dinan, et al.; Biochem. J. 327, 643 (1997)
Cucurbitacin glucosides: antioxidant and free-radical scavenging activities: T. Tannin-Spitz, et al.; BBRC 364, 181 (2007)
Cucurbitacin B induces differentiation, cell cycle arrest, and actin cytoskeletal alterations in myeloid leukemia cells: T. Haritunians, et al.; Leuk. Res. 32, 1366 (2008)
Cucurbitacin B markedly inhibits growth and rapidly affects the cytoskeleton in glioblastoma multiforme: D. Yin, et al.; Int. J. Cancer 123, 1364 (2008)
Cucurbitacin B has a potent antiproliferative effect on breast cancer cells in vitro and in vivo: N. Wakimoto, et al.; Cancer Sci. 99, 1793 (2008)
Cucurbitacin B inhibits STAT3 and the Raf/MEK/ERK pathway in leukemia cell line K562: K.T. Chan, et al.; Cancer Lett. 289, 46 (2010)
Cucurbitacin B induces rapid depletion of the G-actin pool through reactive oxygen species-dependent actin aggregation in melanoma cells: Y. Zhang, et al.; Acta Biochim. Biophys. Sin. (Shanghai) 43, 556 (2011)
Inhibition of Wnt signaling by cucurbitacin B in breast cancer cells: reduction of Wnt-associated proteins and reduced translocation of galectin-3-mediated β-catenin to the nucleus: S. Dakeng, et al.; J. Cell Biochem. 113, 49 (2012)
Cucurbitacin induces autophagy through mitochondrial ROS production which counteracts to limit caspase-dependent apoptosis: T. Zhang, et al.; Autophagy 8, 559 (2012)
Cucurbitacin B inhibits human breast cancer cell proliferation through disruption of microtubule polymerization and nucleophosmin/B23 translocation: S. Duangmano, et al.; BMC Complement. Altern. Med. 12, 185 (2012)
Cucurbitacin B inhibits the translational expression of hypoxia-inducible factor-1α: J. Ma, et al.; Eur. J. Pharmacol. 723, 46 (2014)
Cucurbitacin B induces DNA damage, G2/M phase arrest, and apoptosis mediated by reactive oxygen species (ROS) in leukemia K562 cells: J. Guo, et al.; Anticancer Agents Med. Chem. 14, 1146 (2014)
Cucurbitacin B inhibits proliferation and induces apoptosis via STAT3 pathway inhibition in A549 lung cancer cells: M. Zhang, et al.; Mol. Med. Rep. 10, 2905 (2014)
Inhibitory effect of cucurbitacin B on imiquimod-induced skin inflammation: Z.J. Li, et al.; BBRC 459, 673 (2015)
Cucurbitacin B inhibits immunomodulatory function and the inflammatory response in macrophages: M. Kim, et al.; Immunopharmacol. Immunotoxicol. 37, 473 (2015)

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