18444-66-1

Basic information

• Product Name: Cucurbitacin E
• Synonyms: A-ELATERIN;ALPHA-ELATERIN;CUCURBITACIN E;19-nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione,2,16-alpha,20,25-t;25-acetate;alpha-elaterine;cucurbitacine-e;2,16alpha,20,25-tetrahydroxy-9beta-methyl-10alpha,-19-norlanosta-1,5,23(E)-triene-3,11,22-trione 25-acetate
• CAS NO: 18444-66-1
• Molecular Formula: C₃₂H₄₄O₈
• Molecular Weight: 556.69
• EINECS: 242-325-2
• Product Categories: Tri-Terpenoids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 18444-66-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 228-234°C
• Boiling Point: 545.56°C (rough estimate)
• Flash Point: 224.446 °C
• Appearance: white to beige/
• Density: 1.1059 (rough estimate)
• Vapor Pressure: 1.84E-23mmHg at 25°C
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble15mg/mL, clear
• PKA: 8.51±0.70(Predicted)
• CAS DataBase Reference: Cucurbitacin E(CAS DataBase Reference)
• NIST Chemistry Reference: Cucurbitacin E(18444-66-1)
• EPA Substance Registry System: Cucurbitacin E(18444-66-1)

Safety Data

• Hazard Codes: Xn
• Statements: 25-22
• Safety Statements: 1-22-45-24/25
• RIDADR: 3172
• WGK Germany: 3
• RTECS: RC6305500
• Hazardous Substances Data: 18444-66-1(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 18444-66-1 differently. You can refer to the following data:
1. 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.
2. 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.

InChI:InChI=1/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

Upstream product

• 6199-67-3 cucurbitacin B 

Downstream Products

• 2222-07-3 cucurbitacin I 
• 28973-67-3 23,24-dihydrocucurbitacin E 

Related news

Short reportImmunomodulatory activity of Cucurbitacin E (cas 18444-66-1) isolated from Ecballium elaterium09/06/2019

The immunomodulatory effect of cucurbitacin E, extracted from Ecballium elaterium, was tested on peripheral human lymphocytes. These lymphocytes were co-cultured with cancer cells and an interesting lymphocyte-mediated cytotoxicity was observed.detailed

Cucurbitacin E (cas 18444-66-1) as a new inhibitor of cofilin phosphorylation in human leukemia U937 cells09/05/2019

Cucurbitane-type triterpenes, cucurbitacins B and E, were reported to exhibit cytotoxic effects in several cell lines mediated by JAK/STAT3 signaling. However, neither compound inhibited phosphorylation of STAT3 in human leukemia (U937) cells at low concentrations. We therefore synthesized a bio...detailed

Cucurbitacin E (cas 18444-66-1) ameliorates hepatic fibrosis in vivo and in vitro through activation of AMPK and blocking mTOR-dependent signaling pathway09/04/2019

The study evaluated the potential protective effect and underlying mechanism of Cucurbitacin E (CuE) in both thioacetamide-induced hepatic fibrosis and activated HSCs. CuE inhibited the proliferation of activated HSC/T-6 cells in a concentration- and time-dependent manner; triggered the activati...detailed

Cucurbitacin E (cas 18444-66-1) ameliorates acute graft-versus-host disease by modulating Th17 cell subsets and inhibiting STAT3 activation09/03/2019

Cucurbitacin E (CuE) is a biochemical compound found in plants that are members of the family CuE has been studied for its roles in anti-inflammation and the inhibition of angiogenesis as well as for its properties as an antioxidant. CuE is a new agent that was identified as a selective inhibito...detailed

Relevant articles and documents

Bioactive saponins and glycosides. XXVII. Structures of new cucurbitane-type triterpene glycosides and antiallergic constituents from Citrullus colocynthis

The methanolic extract from the fruit of Citrullus colocynthis showed an inhibitory effect on ear passive cutaneous anaphylaxis reactions as a type I allergic model in mice. From the methanolic extract, two new cucurbitane-type triterpene glycosides, colocynthosides A and B, were isolated together with 17 known constituents. The structures of colocynthosides A and B were elucidated on the basis of chemical and physicochemical evidence. In addition, the principal cucurbitane-type triterpene glycoside, cucurbitacin E 2-O-β-D- glucopyranoside, and its aglycon, cucurbitacin E, exhibited the antiallergic activity at a dose of 100 and 1.25 mg/kg, p.o., respectively.

Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery

Heat shock protein 90 (Hsp90) facilitates the maturation of many newly synthesized and unfolded proteins (clients) via the Hsp90 chaperone cycle, in which Hsp90 forms a heteroprotein complex and relies upon cochaperones, immunophilins, etc., for assistance in client folding. Hsp90 inhibition has emerged as a strategy for anticancer therapies due to the involvement of clients in many oncogenic pathways. Inhibition of chaperone function results in client ubiquitinylation and degradation via the proteasome, ultimately leading to tumor digression. Small molecule inhibitors perturb ATPase activity at the N-terminus and include derivatives of the natural product geldanamycin. However, N-terminal inhibition also leads to induction of the pro-survival heat shock response (HSR), in which displacement of the Hsp90-bound transcription factor, heat shock factor-1, translocates to the nucleus and induces transcription of heat shock proteins, including Hsp90. An alternative strategy for Hsp90 inhibition is disruption of the Hsp90 heteroprotein complex. Disruption of the Hsp90 heteroprotein complex is an effective strategy to prevent client maturation without induction of the HSR. Cucurbitacin D, isolated from Cucurbita texana, and 3-epi-isocucurbitacin D prevented client maturation without induction of the HSR. Cucurbitacin D also disrupted interactions between Hsp90 and two cochaperones, Cdc37 and p23.