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Structure Database (LMSD)

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Common Name

Cucurbitacin B

Systematic Name

Synonyms

LM ID

LMST01010104

Formula

C₃₂H₄₆O₈

Exact Mass

Calculate m/z

558.31927

Sum Composition

ST 32:6;O8

Status

Curated

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Classification

Biological Context

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

This information has been provided by Cayman Chemical

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. 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).

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. 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).

String Representations

InChiKey (Click to copy)

IXQKXEUSCPEQRD-DKRGWESNSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@@]12(C)C[C@H]([C@]([H])([C@](O)(C)C(=O)/C=C/C(C)(C)OC(=O)C)[C@@]1(C)CC([C@@]1(C)[C@]3([H])C[C@@H](C(=O)C(C)(C)C3=CC[C@@]21[H])O)=O)O