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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

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML0577-VAR:
SML0577-25MG:
SML0577-5MG:
SML0577-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pei-Lin Wu et al.
Chemical & pharmaceutical bulletin, 52(3), 345-349 (2004-03-03)
Three new compounds: begonanline (1). nantoamide (2). and methyl (S)-glycerate (3). as well as forty-four known compounds have been isolated and characterized from the rhizomes of Begonia nantoensis. The structures of these compounds were determined by spectral analyses and/or X-ray
Manali Dimri et al.
Development (Cambridge, England), 144(14), 2595-2605 (2017-07-20)
The intrahepatic biliary network is a highly branched three-dimensional network lined by biliary epithelial cells, but how its branching patterns are precisely established is not clear. We designed a new computer-based algorithm that quantitatively computes the structural differences of the
Yasuyuki Sadzuka et al.
International journal of pharmaceutics, 354(1-2), 63-69 (2007-12-07)
We screened various food components for their ability to inhibit doxorubicin (DOX) permeability in tumor cells in vitro with the aim of finding novel modulators. Capsaicin did not change DOX permeability in the tumor cells, although the capsaicin derivatives gingerol
Tehila Tannin-Spitz et al.
Biochemical and biophysical research communications, 364(1), 181-186 (2007-10-19)
The cucurbitacins are of great interest because of the wide range of biological activities they exhibit in plants and animals. We studied the antioxidant properties of cucurbitacin B + E glucosides (cucurbitacin glucoside combination, CGC) and their direct free-radical scavenging
Yanmin Dong et al.
Carcinogenesis, 31(12), 2097-2104 (2010-08-25)
Cucurbitacin E (CuE, α-elaterin), a tetracyclic triterpenes compound from folk traditional Chinese medicine plants, has been shown to inhibit cancer cell growth, inflammatory response and bilirubin-albumin binding. However, the effects of CuE on tumor angiogenesis and its potential molecular mechanism
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