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HomeProduct name listCucurbitacin E

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
Cucurbitacin E Structural

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)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral

Computed Descriptors for Cucurbitacin E

InChIKey NDYMQXYDSVBNLL-MUYMLXPFSA-N

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