Cucurbitacin E
Synonym(s):α-Elaterin;α-Elaterine
- CAS NO.:18444-66-1
- Empirical Formula: C32H44O8
- Molecular Weight: 556.69
- MDL number: MFCD00135936
- EINECS: 242-325-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 19:05:58
What is Cucurbitacin E?
Description
Cucurbitacin E is a plant-derived triterpene that has diverse biological activities. At a concentration of 10 pM, it reduces MPP+-induced death of neuronal PC12 cells through inhibition of autophagy in vitro. Cucurbitacin E inhibits growth of T24 bladder, MDA-MB-468 and MCF-7 breast, PC3 prostate, and colorectal cancer cell lines (IC50s = 50-1,000 nM) through induction of G2/M arrest and apoptosis. It increases bilirubin binding to human serum albumin (HSA) in human plasma in a dose-dependent manner. Cucurbitacin E also inhibits depolymerization of actin filaments isolated from rabbit skeletal muscle actin and in HeLa cells.
Chemical properties
white to beige powder
The Uses of Cucurbitacin E
Cucurbitacin E is a biochemical compound from the family of Cucurbitacins. Cucurbitacin E is a highly oxidated steroid consisting of a tetracyclic triterpene. Cucurbitacin E is known to possess broad spectrum of potential anti-inflammatory, antitumor andantioxidant effects.
The Uses of Cucurbitacin E
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.
Definition
ChEBI: A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 1, 5 and 23.
General Description
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG.
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.
Properties of Cucurbitacin E
Melting point: | 228-234°C |
Boiling point: | 545.56°C (rough estimate) |
alpha | D -59° (c = 0.7 in chloroform) |
Density | 1.1059 (rough estimate) |
refractive index | 1.4900 (estimate) |
storage temp. | -20°C |
solubility | DMSO: soluble15mg/mL, clear |
form | powder |
pka | 8.51±0.70(Predicted) |
color | white to beige |
optical activity | [α]/D -60 to -75°, c = 0.7 (CDCl3) |
Safety information for Cucurbitacin E
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Computed Descriptors for Cucurbitacin E
InChIKey | NDYMQXYDSVBNLL-MUYMLXPFSA-N |
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