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Euphorbiasteroid Sale

(Synonyms: 千金子甾醇) 目录号 : GC38422

A tricyclic diterpene

Euphorbiasteroid Chemical Structure

Cas No.:28649-59-4

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产品描述

Euphorbiasteroid is a tricyclic diterpene that has been found in the plant E. lathyris.1 It inhibits early-stage adipogenesis of 3T3-L1 cells, decreasing intracellular triglyceride accumulation when used at concentrations of 25 and 50 ?M.2 It decreases the expression of Fas, C/EBPα, PPARγ, and SREBP-1c and increases phosphorylation of AMP-activated protein kinase (AMPK) and acetyl-coenzyme A carboxylase (ACC) in 3T3-L1 cells. Euphorbiasteroid inhibits proliferation of HL-60 cells in a concentration-dependent manner, as well as induces apoptosis and increases the expression of Fas and Fas ligand (FasL) and the activity of caspase-3 and caspase-8 in HL-60 cells.3 It increases P-glycoprotein activity, reverses multi-drug resistance, and restores cytotoxicity of the anticancer agents vinblastine , paclitaxel , and doxorubicin to MES-SA/Dx5 sarcoma cells.4

1.Adolf, W., Hecker, E., Balmain, A., et al.“Euphorbiasteroid” (epoxy-lathyrol). A new tricyclic diterpene from Euphorbia lathyris L.Tetrahedron Lett.11(26)2241-2244(1970) 2.Park, S.-J., Park, J.H., Han, A., et al.Euphorbiasteroid, a component of Euphorbia lathyris L., inhibits adipogenesis of 3T3-L1 cells via activation of AMP-activated protein kinaseCell Biochem. Funct.33(4)220-225(2015) 3.Guo, F., Li, X., Zhang, C., et al.Roles and mechanisms of Fas/FasL in the apoptosis of HL-60 cells induced by euphorbiasteroidJ. Int. Oncology41(9)679-684(2014) 4.Choi, J.S., Kang, N.S., Min, Y.K., et al.Euphorbiasteroid reverses P-glycoprotein-mediated multi-drug resistance in human sarcoma cell line MES-SA/Dx5Phytother. Res.24(7)1042-1046(2010)

Chemical Properties

Cas No. 28649-59-4 SDF
别名 千金子甾醇
Canonical SMILES CC(O[C@@](C[C@H](C)[C@@H]1OC(CC2=CC=CC=C2)=O)(C(/C(C)=C\[C@@H](C3(C)C)[C@@H]3CC[C@@]45CO5)=O)[C@@]1([H])[C@@H]4OC(C)=O)=O
分子式 C32H40O8 分子量 552.66
溶解度 DMF: 5 mg/ml,DMSO: 5 mg/ml,Ethanol: Partially soluble 储存条件 4°C, protect from light
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Research Update

Euphorbiasteroid Abrogates EGFR and Wnt/β-Catenin Signaling in Non-Small-Cell Lung Cancer Cells to Impart Anticancer Activity

Molecules 2022 Jun 14;27(12):3824.PMID:35744950DOI:10.3390/molecules27123824.

EGFR and Wnt/β-catenin signaling pathways play a prominent role in tumor progression in various human cancers including non-small-cell lung carcinoma (NSCLC). Transactivation and crosstalk between the EGFR and Wnt/β-catenin pathways may contribute to the aggressiveness of cancers. Targeting these oncogenic pathways with small molecules is an attractive approach to counteract various types of cancers. In this study, we demonstrate the effect of Euphorbiasteroid (EPBS) on the EGFR and Wnt/β-catenin pathways in NSCLC cells. EPBS induced preferential cytotoxicity toward A549 (wildtype EGFR-expressing) cells over PC-9 (mutant EGFR-expressing) cells. EPBS suppressed the expression of EGFR, Wnt3a, β-catenin, and FZD-1, and the reduction in β-catenin levels was found to be mediated through the activation of GSK-3β. EPBS reduced the phosphorylation of GSK-3βS9 with a parallel increase in β-TrCP and phosphorylation of GSK-3βY216. Lithium chloride treatment increased the phosphorylation of GSK-3βS9 and nuclear localization of β-catenin, whereas EPBS reverted these effects. Forced expression or depletion of EGFR in NSCLC cells increased or decreased the levels of Wnt3a, β-catenin, and FZD-1, respectively. Overall, EPBS abrogates EGFR and Wnt/β-catenin pathways to impart its anticancer activity in NSCLC cells.

Comprehensive Metabolic Profiling of Euphorbiasteroid in Rats by Integrating UPLC-Q/TOF-MS and NMR as Well as Microbial Biotransformation

Metabolites 2022 Sep 2;12(9):830.PMID:36144234DOI:10.3390/metabo12090830.

Euphorbiasteroid, a lathyrane-type diterpene from Euphorbiae semen (the seeds of Euphorbia lathyris L.), has been shown to have a variety of pharmacological effects such as anti-tumor and anti-obesity. This study aims to investigate the metabolic profiles of Euphorbiasteroid in rats and rat liver microsomes (RLMs) and Cunninghamella elegans bio-110930 by integrating ultra-performance liquid chromatography-quadrupole time-of-flight-mass spectrometry (UPLC-Q/TOF-MS), UNIFI software, and NMR techniques. A total of 31 metabolites were identified in rats. Twelve metabolites (M1-M5, M8, M12-M13, M16, M24-M25, and M29) were matched to the metabolites obtained by RLMs incubation and the microbial transformation of C. elegans bio-110930 and their structures were exactly determined through analysis of NMR spectroscopic data. In addition, the metabolic pathways of Euphorbiasteroid were then clarified, mainly including hydroxylation, hydrolysis, oxygenation, sulfonation, and glycosylation. Finally, three metabolites, M3 (20-hydroxyl Euphorbiasteroid), M24 (epoxylathyrol) and M25 (15-deacetyl Euphorbiasteroid), showed significant cytotoxicity against four human cell lines with IC50 values from 3.60 μM to 40.74 μM. This is the first systematic investigation into the in vivo metabolic pathways of Euphorbiasteroid and the cytotoxicity of its metabolites, which will be beneficial for better predicting the metabolism profile of Euphorbiasteroid in humans and understanding its possible toxic material basis.

Euphorbiasteroid, a component of Euphorbia lathyris L., inhibits adipogenesis of 3T3-L1 cells via activation of AMP-activated protein kinase

Cell Biochem Funct 2015 Jun;33(4):220-5.PMID:25914364DOI:10.1002/cbf.3107.

The purpose of this study is to investigate the effects of Euphorbiasteroid, a component of Euphorbia lathyris L., on adipogenesis of 3T3-L1 pre-adipocytes and its underlying mechanisms. Euphorbiasteroid decreased differentiation of 3T3-L1 cells via reduction of intracellular triglyceride (TG) accumulation at concentrations of 25 and 50 μM. In addition, Euphorbiasteroid altered the key regulator proteins of adipogenesis in the early stage of adipocyte differentiation by increasing the phosphorylation of AMP-activated protein kinase (AMPK) and acetyl-CoA carboxylase. Subsequently, levels of adipogenic proteins, including fatty acid synthase, peroxisome proliferator-activated receptor-γ and CCAAT/enhancer-binding protein α, were decreased by Euphorbiasteroid treatment at the late stage of adipocyte differentiation. The anti-adipogenic effect of Euphorbiasteroid may be derived from inhibition of early stage of adipocyte differentiation. Taken together, Euphorbiasteroid inhibits adipogenesis of 3T3-L1 cells through activation of the AMPK pathway. Therefore, Euphorbiasteroid and its source plant, E. lathyris L., could possibly be one of the fascinating anti-obesity agent.

Euphorbiasteroid reverses P-glycoprotein-mediated multi-drug resistance in human sarcoma cell line MES-SA/Dx5

Phytother Res 2010 Jul;24(7):1042-6.PMID:19960428DOI:10.1002/ptr.3073.

In this study, we evaluated whether Euphorbiasteroid isolated from Euphorbia lathyris has the potential to reverse P-glycoprotein (P-gp)-mediated multi-drug resistance (MDR) by using the drug-sensitive human sarcoma cell line MES-SA and its MDR counterpart MES-SA/Dx5. Interestingly, even at low concentrations of Euphorbiasteroid (1-3 microM), it efficiently restored the toxicities of anticancer drugs including vinblastine, taxol and doxorubicin in MES-SA/Dx5 cells. Additionally, the computational Bayesian model for predicting potential P-gp substrates or inhibitors revealed that Euphorbiasteroid showed 97% probability for substrate likeness having similar molecular features with 50 P-gp substrates. Consistent with this result, the substrate likeness of Euphorbiasteroid was also experimentally confirmed by P-gp ATPase activity assay. In conclusion, our finding suggested that Euphorbiasteroid could be a transport substrate for P-gp that can effectively inhibit P-gp-mediated drug transport and reverse resistance to anticancer drugs in MES-SA/Dx5 cells.

Construction of magnetic drug delivery system and its potential application in tumor theranostics

Biomed Pharmacother 2022 Oct;154:113545.PMID:36007274DOI:10.1016/j.biopha.2022.113545.

Magnetic nanoparticles(NPs) are characterized by a rich variety of properties. Because of their excellent physical and chemical properties, they have come to the fore in biomedicine and other fields. The magnetic NPs were extensively studied in magnetic separation of cells, targeted drug delivery, tumor hyperthermia, chemo-photothermal therapy, magnetic resonance imaging (MRI) and other biomedical fields. Magnetic NPs are increasingly used in magnetic resonance imaging (MRI) based on their inherent magnetic targeting, superparamagnetic enzyme-like catalytic properties and nanoscale size. Poly(lactic-co-glycolic acid) (PLGA) is a promising biodegradable material approved by FDA and EU for drug delivery. Currently, PLGA-based magnetic nano-drug delivery systems have attracted the attention of researchers. Herein, we achieved the effective encapsulation of sized-controlled polyethylene glycol-3,4-dihydroxy benzyl-amine-coated superparamagnetic iron oxide nanoparticles (SPIO NPs) and Euphorbiasteroid into PLGA nanospheres via a modified multiple emulsion solvent evaporation method (W1/O2/W2). NPs with narrow size distribution and acceptable magnetic properties were developed that are very useful for applications involving cancer therapy and MRI. Furthermore, SPIO-PLGA NPs enhanced the MRI T2 relaxation properties of tumor sites.The prepared SPIO NPs and magnetic PLGA nanospheres can be promising magnetic drug delivery systems for tumor theranostics. This study has successfully constructed a tumor-targeting and magnetic-targeting smart nanocarrier with enhanced permeability and retention, multimodal anti-cancer therapeutics and biodegradability, which could be a hopeful candidate for anti-tumor therapy in the future.