| Identification | Back Directory | [Name]
Cucurbitacin E | [CAS]
18444-66-1 | [Synonyms]
A-ELATERIN
25-acetate
Cucurbit E
α-Elaterine
ALPHA-ELATERIN
CUCURBITACIN E
alpha-elaterine
cucurbitacine-e
CUCURBITACIN E(SH)
CUCURBITACIN E hplc
Cucurbitacin E, >99%
Cucurbitacin E USP/EP/BP
CUCURBITACIN E WITH HPLC
Cucurbitacin E 18444-66-1
Cucurbitacin E (α-Elaterin
Cucurbitacin E, 98%, from Cucumis melo L.
19-nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione,2,16-alpha,20,25-t
2,16α,20,25-tetrahydroxy-9β-methyl-10α,-19-norlanosta-1,5,23(E)-triene-3,11,22-trione 25-acetate
(10α,23E)-25-(Acetyloxy)-2,16α,20-trihydroxy-9β-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione
(9β,10α,23E)-25-Acetyloxy-2,16α,20-trihydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione
(9β,10α,23E)-25-(Acetyloxy)-2,16α,20-trihydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione
19-Norlanosta-1,5,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9β,10α,16α,23E)-
2,16alpha,20,25-tetrahydroxy-9beta-methyl-10alpha,-19-norlanosta-1,5,23(E)-triene-3,11,22-trione 25-acetate
[(E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-Dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate | [EINECS(EC#)]
242-325-2 | [Molecular Formula]
C32H44O8 | [MDL Number]
MFCD00135936 | [MOL File]
18444-66-1.mol | [Molecular Weight]
556.69 |
| Chemical Properties | Back Directory | [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 Rotation]
[α]/D -60 to -75°, c = 0.7 (CDCl3) | [InChIKey]
NDYMQXYDSVBNLL-MUYMLXPFSA-N | [SMILES]
[C@@]12(C)C[C@@H](O)[C@]([H])([C@](O)(C)C(=O)/C=C/C(C)(C)OC(=O)C)[C@@]1(C)CC(=O)[C@@]1(C)[C@]3([H])C=C(C(=O)C(C)(C)C3=CC[C@@]21[H])O |&1:0,3,5,7,21,26,28,40,r| | [LogP]
3.150 (est) |
| Hazard Information | Back Directory | [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.1 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.2,3,4 It increases bilirubin binding to human serum albumin (HSA) in human plasma in a dose-dependent manner.5 Cucurbitacin E also inhibits depolymerization of actin filaments isolated from rabbit skeletal muscle actin and in HeLa cells.6 | [Chemical Properties]
white to beige powder | [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. | [References]
[1] ANNE-MARIE AREL-DUBEAU. Cucurbitacin E has neuroprotective properties and autophagic modulating activities on dopaminergic neurons.[J]. Oxidative Medicine and Cellular Longevity, 2014, 2014: 425496. DOI: 10.1155/2014/425496
[2] Y-C HSU M J C T Y Huang. Therapeutic ROS targeting of GADD45γ in the induction of G2/M arrest in primary human colorectal cancer cell lines by cucurbitacin E[J]. Cell Death & Disease, 2014, 5 4: e1198-e1198. DOI: 10.1038/cddis.2014.151
[3] YANJIE KONG. Cucurbitacin E induces cell cycle G2/M phase arrest and apoptosis in triple negative breast cancer.[J]. PLoS ONE, 2014: e103760. DOI: 10.1371/journal.pone.0103760
[4] WEN-WEN HUANG. Cucurbitacin E Induces G(2)/M Phase Arrest through STAT3/p53/p21 Signaling and Provokes Apoptosis via Fas/CD95 and Mitochondria-Dependent Pathways in Human Bladder Cancer T24 Cells.[J]. Evidence-based Complementary and Alternative Medicine, 2012: 952762. DOI: 10.1155/2012/952762
[5] H. GREIGE-GERGES . Effect of cucurbitacins on bilirubin–albumin binding in human plasma[J]. Life sciences, 2007, 80 6: Pages 579-585. DOI: 10.1016/j.lfs.2006.10.005
[6] PIA M. S?RENSEN. The Natural Product Cucurbitacin E Inhibits Depolymerization of Actin Filaments[J]. ACS Chemical Biology, 2012, 7 9: 1502-1508. DOI: 10.1021/cb300254s |
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