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 belonging to the family of Cucurbitacins. It is a highly oxidized steroid with a tetracyclic triterpene structure, featuring a lanostane skeleton that is multi-substituted with hydroxy, methyl, and oxo groups, along with unsaturation at positions 1, 5, and 23. Cucurbitacin E exhibits a white to beige powder form and possesses a broad spectrum of potential biological activities, including anti-inflammatory, antitumor, and antioxidant effects.

Uses

Used in Pharmaceutical Industry:
Cucurbitacin E is used as a cofilin inhibitor and a F-actin stabilizer for various therapeutic applications. Its ability to inhibit autophagy at a concentration of 10 pM helps reduce MPP+-induced death of neuronal PC12 cells in vitro. Additionally, it demonstrates antitumor effects by inhibiting the growth of various cancer cell lines, such as T24 bladder, MDA-MB-468 and MCF-7 breast, PC3 prostate, and colorectal cancer cell lines (IC50s = 50-1,000 nM) through the induction of G2/M arrest and apoptosis.
Used in Biochemical Research:
Cucurbitacin E is utilized as a primary reference substance with assigned absolute purity, considering chromatographic purity, water, residual solvents, and inorganic impurities. Its exact purity value can be found on the certificate provided by PhytoLab GmbH & Co. KG. This makes it a valuable tool for biochemical research and analysis.
Used in Biochemistry and Molecular Biology:
Cucurbitacin E's ability to inhibit depolymerization of actin filaments isolated from rabbit skeletal muscle actin and in HeLa cells makes it a useful compound in the study of cytoskeleton dynamics and related cellular processes.

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.