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Safety Information

SML0577

Sigma-Aldrich

Cucurbitacin E

≥95% (HPLC)

Synonym(s):

α-Elaterin, α-Elaterine

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About This Item

Empirical Formula (Hill Notation):
C32H44O8
CAS Number:
18444-66-1
Molecular Weight:
556.69
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

optical activity

[α]/D -60 to -75°, c = 0.7 (CDCl3)

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

InChI

1S/C32H44O8/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/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1

InChI key

NDYMQXYDSVBNLL-MUYMLXPFSA-N

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Application

Cucurbitacin E has been used as a cofilin inhibitor. It is also used as a F-actin stabilizer to prevent membrane-associated periodic skeleton (MPS) loss and protect from axonal fragmentation.

Biochem/physiol Actions

Cucurbitacin E is a potent inhibitor of actin depolymerization. Cucurbitacin E is more active than jasplakinolide, and has a different mechanism of action, binding to a different site. Cucurbitacin E binds specifically to filamentous actin (F-actin) forming a covalent bond at residue Cys257, but not to monomeric actin (G-actin), stabilizing F-actin, without affecting actin polymerization or nucleation.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Lamice Habib et al.
International journal of pharmaceutics, 448(1), 313-319 (2013-03-26)
Cucurbitacin E (Cuc E), highly oxygenated triterpene from cucurbitaceae family, was demonstrated to possess anti-proliferative, anti-inflammatory and anti-oxidant activities. Here, we studied the effect of Cuc E on the properties of the phospholipid membrane. Large unilamellar vesicles, with and without
Three-dimensional structural analysis reveals a Cdk5-mediated kinase cascade regulating hepatic biliary network branching in zebrafish
Dimri M, et al.
Development, 144(14), 2595-2605 (2017)
Chao-Ming Hung et al.
International journal of molecular sciences, 14(8), 17147-17156 (2013-08-24)
Human oral squamous cell carcinoma (OSCC) is a common form of malignant cancer, for which radiotherapy or chemotherapy are the main treatment methods. Cucurbitacin E (CuE) is a natural compound previously shown to be an antifeedant as well as a
Xiaolong He et al.
Oncology letters, 13(6), 4905-4910 (2017-06-11)
Cucurbitacin E is an important member of the cucurbitacin family and exhibits inhibitory effects in various types of cancer. Cucurbitacin is a potential antineoplastic drug; however, its anticancer effect in human prostate cancer (PC) remains unknown. The aim of the
Yanchun Li et al.
Anti-cancer drugs, 21(4), 389-400 (2010-01-30)
The antiproliferative and apoptotic effects of cucurbitacin E, a natural product isolated from Cucurbitaceae, were determined in human leukemia HL-60 cells. Cucurbitacin E at low concentrations (3-50 nmol/l) inhibited the growth of HL-60 cells, which was associated with G2/M cell-cycle
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