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SML0577

Sigma-Aldrich

Cucurbitacin E

≥95% (HPLC)

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Synonym(s):
α-Elaterin, α-Elaterine
Empirical Formula (Hill Notation):
C32H44O8
CAS Number:
18444-66-1
Molecular Weight:
556.69
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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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
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
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
Siddig Ibrahim Abdelwahab et al.
Fitoterapia, 82(8), 1190-1197 (2011-08-30)
The in vivo and in vitro mechanistic anti-inflammatory actions of cucurbitacin E (CE) (Citrullus lanatus var. citroides) were examined. The results showed that LPS/INF-γ increased NO production in RAW264.7 macrophages, whereas L-NAME and CE curtailed it. CE did not reveal
Tao Zhang et al.
Breast cancer research and treatment, 135(2), 445-458 (2012-07-31)
Tumor metastasis is the main cause of cancer-related deaths of patients. Breast cancer is highly malignant with considerable metastatic potential, which urges the necessity for developing novel potential drug candidate to prevent tumor metastasis. Here, we report our finding with
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