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Isodeoxyelephantopin

CAS# 38927-54-7

Isodeoxyelephantopin

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Chemical structure

Isodeoxyelephantopin

3D structure

Chemical Properties of Isodeoxyelephantopin

Cas No. 38927-54-7 SDF Download SDF
PubChem ID 38359583 Appearance Powder
Formula C19H20O6 M.Wt 344.36
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(3S,4R,8R,9E,12S)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.04,8]pentadeca-1(15),9-dien-3-yl] 2-methylprop-2-enoate
SMILES CC1=CC2C(C(CC3=CC(C1)OC3=O)OC(=O)C(=C)C)C(=C)C(=O)O2
Standard InChIKey JMUOPRSXUVOHFE-MCYOVBASSA-N
Standard InChI InChI=1S/C19H20O6/c1-9(2)17(20)24-15-8-12-7-13(23-19(12)22)5-10(3)6-14-16(15)11(4)18(21)25-14/h6-7,13-16H,1,4-5,8H2,2-3H3/b10-6+/t13-,14+,15-,16-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Isodeoxyelephantopin

The herbs of Elephantopus scaber Linn.

Biological Activity of Isodeoxyelephantopin

Description1. Isodeoxyelephantopin exerts antitumor effects on several cancer cells by inducing apoptosis , cell cycle arrest , and inhibiting proliferation . 2. Isodeoxyelephantopin enhances apoptosis and inhibit invasion and osteoclastogenesis by inhibiting NF-kappaB activation and NF-kappaB-regulated gene expression.
TargetsIFN-γ | ROS | IL Receptor | NF-kB | TNF-α | p65

Isodeoxyelephantopin Dilution Calculator

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Preparing Stock Solutions of Isodeoxyelephantopin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9039 mL 14.5197 mL 29.0394 mL 58.0788 mL 72.5984 mL
5 mM 0.5808 mL 2.9039 mL 5.8079 mL 11.6158 mL 14.5197 mL
10 mM 0.2904 mL 1.452 mL 2.9039 mL 5.8079 mL 7.2598 mL
50 mM 0.0581 mL 0.2904 mL 0.5808 mL 1.1616 mL 1.452 mL
100 mM 0.029 mL 0.1452 mL 0.2904 mL 0.5808 mL 0.726 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Isodeoxyelephantopin

Isodeoxyelephantopin, a novel sesquiterpene lactone, potentiates apoptosis, inhibits invasion, and abolishes osteoclastogenesis through suppression of nuclear factor-kappaB (nf-kappaB) activation and nf-kappaB-regulated gene expression.[Pubmed:17021000]

Clin Cancer Res. 2006 Oct 1;12(19):5910-8.

PURPOSE: Deoxyelephantopin (ESD) and Isodeoxyelephantopin (ESI) are two sesquiterpene lactones derived from the medicinal plant Elephantopus scaber Linn. (Asteraceae). Although they are used for the treatment of a wide variety of proinflammatory diseases, very little is known about their mechanism of action. Because most genes that control inflammation are regulated by activation of the transcription factor nuclear factor-kappaB (NF-kappaB), we postulated that ESD and ESI mediate their activities through modulation of the NF-kappaB activation pathway. EXPERIMENTAL DESIGN: We investigated the effect of ESI and ESD on NF-kappaB activation by electrophoretic mobility shift assay and NF-kappaB-regulated gene expression by Western blot analysis. RESULTS: We found that ESI suppressed NF-kappaB activation induced by a wide variety of inflammatory agents, including tumor necrosis factor (TNF), interleukin-1beta, phorbol 12-myristate 13-acetate, and lipopolysaccharide. The suppression was not cell type specific, and both inducible and constitutive NF-kappaB activation was blocked. ESI did not interfere with the binding of NF-kappaB to DNA but rather inhibited IkappaBalpha kinase, IkappaBalpha phosphorylation, IkappaBalpha degradation, p65 phosphorylation, and subsequent p65 nuclear translocation. ESI also suppressed the expression of TNF-induced NF-kappaB-regulated, proliferative, antiapoptotic, and metastatic gene products. These effects correlated with enhancement of apoptosis induced by TNF and suppression of TNF-induced invasion and receptor activator of NF-kappaB ligand-induced osteoclastogenesis. CONCLUSION: Our results indicate that ESI inhibits NF-kappaB activation and NF-kappaB-regulated gene expression, which may explain the ability of ESI to enhance apoptosis and inhibit invasion and osteoclastogenesis.

Isodeoxyelephantopin from Elephantopus scaber (Didancao) induces cell cycle arrest and caspase-3-mediated apoptosis in breast carcinoma T47D cells and lung carcinoma A549 cells.[Pubmed:24742378]

Chin Med. 2014 Apr 17;9:14.

BACKGROUND: Isodeoxyelephantopin (IDOE) isolated from Elephantopus scaber L. (Didancao) is used in Chinese medicine for the treatment of some types of cancer. The anti-cancer mechanism of IDOE remains unclear. This study aims to investigate the antiproliferative activity of IDOE on breast carcinoma T47D cells and lung carcinoma A549 cells. METHODS: The growth inhibitory effects of IDOE on breast carcinoma T47D cells, lung carcinoma A549 cells, and normal lymphocytes were evaluated by the MTT assay. Morphological analysis of apoptosis induction was performed by acridine orange/ethidium bromide dual-staining and Hoechst 33342 nuclear staining. The cell cycle profile, caspase-3 expression, and annexin V staining were evaluated by flow cytometry. RESULTS: IDOE inhibited the growth of A549 and T47D cells in a dose- and time-dependent manner with IC50 values of 10.46 and 1.3 mug/mL, respectively. IDOE was not significantly toxic to normal lymphocytes. The cells became detached from the monolayer and rounded up, had fragmented nuclei and condensed chromatin, and the numbers of apoptotic cells increased (P = 0.0003). IDOE-induced cell death was associated with activated caspase-3 expression followed by cell cycle arrest at G2/M phase. CONCLUSIONS: IDOE inhibited the proliferation of breast cancer cells and lung carcinoma cells and induced caspase-3-mediated apoptosis and cell cycle arrest in the treated cells.

Quantitative proteomics characterization on the antitumor effects of isodeoxyelephantopin against nasopharyngeal carcinoma.[Pubmed:23970500]

Proteomics. 2013 Nov;13(21):3222-32.

Isolated from Elephantopus scaber L., a Chinese medicinal herb that is widely used to prevent and treat cancers in China, Isodeoxyelephantopin (ESI) exerted antitumor effects on several cancer cells. However, its antitumor mechanism is still not clear. In this study, we found that ESI could induce G2/M arrest and subsequently stimulate cell apoptosis in dose- and time-dependent manners. We used SILAC quantitative proteomics to identify ESI-regulated proteins in cancer cells, and found that 124 proteins were significantly altered in expression. Gene ontology and Ingenuity Pathway Analysis revealed that these proteins were mainly involved in the regulation of oxidative stress and inflammation response. Functional studies demonstrated that ESI induced G2/M arrest and apoptosis by inducing ROS generation, and that antioxidant N-acetyl-l-cysteine could block the ESI-induced antitumor effects. Accumulated ROS resulted in DNA breakage, subsequent G2/M arrest and mitochondrial-mediated apoptosis. ESI upregulated the expression of anticancer inflammation factors IL-12a, IFN-alpha, and IFN-beta through ROS-dependent and independent pathways. The current work reveals that ESI exerts its antitumor effects through ROS-dependent DNA damage, mitochondrial-mediated apoptosis mechanism and antitumor inflammation factor pathway.

Description

Isodeoxyelephantopin is a sesquiterpene lactone isolated from Elephantopus scaber. Isodeoxyelephantopin induces ROS generation, suppresses NF-κB activation. Isodeoxyelephantopin also modulates LncRNA expression and exhibit activities against breast cancer.

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