Cucurbitacin E Chemical Properties

Melting point:

228-234°C

alpha 

D -59° (c = 0.7 in chloroform)

Boiling point:

545.56°C (rough estimate)

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)

InChIKey

NDYMQXYDSVBNLL-MUYMLXPFSA-N

LogP

3.150 (est)

Safety Information

Hazard Codes 

Xn

Risk Statements 

25-22

Safety Statements 

1-22-45-24/25

RIDADR 

3172

WGK Germany 

3

RTECS 

RC6305500

HS Code 

29153900

Toxicity

LD50 orally in mice: 340 mg/kg (Albert)

Cucurbitacin E Usage And Synthesis

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

Uses

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.

Uses

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.

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.

Cucurbitacin E(18444-66-1)Related Product Information

• Cucurbitacin,CUCURBITACIN B(RG),CUCURBITACIN B
• Cucurbitacin C
• CUCURBITACIN D,CUCURBITACIN D WITH HPLC
• 1,2-Cyclohexanedione
• 2,6-Dimethyl-5-heptenal
• ADOXAL
• Calebassine
• FITONE
• CUCURBITACIN D(SH)
• Cucurbitacin IIb
• CUCURBITACIN IIA
• CUCURBITACIN I hplc,CUCURBITACIN I WITH HPLC,Cucurbitacin I hydrate,CUCURBITACIN I(SH),CUCURBITACIN I
• Cucurbitacin Ia,Cucurbitacin F-25-acetate
• Cucurbitacin A
• Cucurbitacin L
• Cucurbitacin F
• dihydrocucurbitacin F
• Cucurbitacin H,24-epi-Cucurbitacin G,Cucurbitacin G