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Euphorbiasteroid

CAS# 28649-59-4

Euphorbiasteroid

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Chemical structure

Euphorbiasteroid

3D structure

Chemical Properties of Euphorbiasteroid

Cas No. 28649-59-4 SDF Download SDF
PubChem ID 15940183 Appearance White powder
Formula C32H40O8 M.Wt 552.66
Type of Compound Diterpenoids Storage Desiccate at -20°C
Synonyms Euphorbia factor L1;76376-43-7
Solubility Soluble in chloroform
Chemical Name [(1'R,2R,3'E,5'R,7'S,11'S,12'R,13'S,14'S)-1',11'-diacetyloxy-3',6',6',14'-tetramethyl-2'-oxospiro[oxirane-2,10'-tricyclo[10.3.0.05,7]pentadec-3-ene]-13'-yl] 2-phenylacetate
SMILES CC1CC2(C(C1OC(=O)CC3=CC=CC=C3)C(C4(CCC5C(C5(C)C)C=C(C2=O)C)CO4)OC(=O)C)OC(=O)C
Standard InChIKey SDGDWRYYHQOQOJ-XXMLZKCSSA-N
Standard InChI InChI=1S/C32H40O8/c1-18-14-24-23(30(24,5)6)12-13-31(17-37-31)29(38-20(3)33)26-27(39-25(35)15-22-10-8-7-9-11-22)19(2)16-32(26,28(18)36)40-21(4)34/h7-11,14,19,23-24,26-27,29H,12-13,15-17H2,1-6H3/b18-14+/t19-,23-,24+,26+,27-,29-,31+,32+/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 Euphorbiasteroid

The herbs of Euphorbia pekinensis Rupr.

Biological Activity of Euphorbiasteroid

DescriptionEuphorbiasteroid has anti-obesity activities, it inhibits adipogenesis of 3T3-L1 cells through activation of the AMPK pathway. 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; it induces HL-60 cells to apoptosis via promoting Bcl-2/Bax apoptotic signaling pathway in a dose-dependent manner.Euphorbia factor L1 inhibits osteoclastogenesis and induces osteoclast apoptosis, it can enhance the ATP hydrolysis activity of ABCB1 stimulated by verapamil. Euphorbia factor L1 inhibits the efflux of ABCB1 in KBv200 and MCF-7/adr cells, does not downregulate their expression either in mRNA or protein level.
TargetsAMPK | P-gp | Bcl-2/Bax | ATPase | ERK | Akt
In vitro

Apoptosis sensitization by Euphorbia factor L1 in ABCB1-mediated multidrug resistant K562/ADR cells.[Pubmed: 24135937]

Molecules. 2013 Oct 16;18(10):12793-808.


METHODS AND RESULTS:
In this article, reversal activities of Euphorbia factor L1 (EFL1) against ABCB1-mediated multidrug resistance (MDR) and apoptosis sensitization in K562/ADR cells are reported. EFL1 decreased the IC50 values of anticancer agents in K562/ADR cells over-expressing ABCB1. However, EFL1 did not affect the IC50 values of anticancer agents in sensitive K562 cells. Additionally, EFL1 increased the intracellular accumulation of rhodamine 123 and doxorubicin in K562/ADR cells without affecting their accumulation in K562 cells. Furthermore, EFL1 sensitized the apoptosis triggered by vincristine in K562/ADR cells via mitochondrial pathway, as confirmed by Annexin V-FITC/PI detection and western blot. At the same time, EFL1 did not influence the apoptosis induced by vincristine in K562 cells.
CONCLUSIONS:
Western blot results showed that EFL1 did not affect the phosphorylation level of AKT and ERK in K562 and K562/ADR cells. Finally, EFL1 did not down-regulate protein expression of ABCB1.

Euphorbiasteroid, a component of Euphorbia lathyris L., inhibits adipogenesis of 3T3-L1 cells via activation of AMP-activated protein kinase.[Pubmed: 25914364]

Cell Biochem Funct. 2015 Jun;33(4):220-5.

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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
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.[Pubmed: 19960428 ]

Phytother Res. 2010 Jul;24(7):1042-6.


METHODS AND RESULTS:
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.
CONCLUSIONS:
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.

Protocol of Euphorbiasteroid

Kinase Assay

Euphorbia factor L1 reverses ABCB1-mediated multidrug resistance involving interaction with ABCB1 independent of ABCB1 downregualtion.[Pubmed: 21308736 ]

J Cell Biochem. 2011 Apr;112(4):1076-83.

Euphorbia factor L1 (EFL1) belongs to diterpenoids of genus Euphorbia.
METHODS AND RESULTS:
In this article, its reversal activity against ABCB1-mediated MDR in KBv200 and MCF-7/adr cells was reported. However, EFL1 did not alter the sensitivity of KB and MCF-7 cells to chemotherapeutic agents. Meanwhile, EFL1 significantly increased accumulation of doxorubicin and rhodamine 123 in KBv200 and MCF-7/adr cells, showing no significant influence on that of KB and MCF-7 cells. Furthermore, EFL1 could enhance the ATP hydrolysis activity of ABCB1 stimulated by verapamil. At the same time, EFL1 inhibited the efflux of ABCB1 in KBv200 and MCF-7/adr cells. In addition, EFL1 did not downregulate expression of ABCB1 in KBv200 and MCF-7/adr cells either in mRNA or protein level.

Cell Research

Mechanism of euphorbiasteroid inducing apoptosis of HL-60 cells[Reference: WebLink]

Chinese Journal of Cancer Prevention & Treatment, 2014 , 21 (23) :1865-1870.

To investigate the effect of Euphorbiasteroid on inducing the apoptosis of HL-60 cells and identify the role of Bcl-2/Bax signaling pathway in this process.
METHODS AND RESULTS:
HL-60 cells were treated with low, middleand high dose of Euphorbiasteroid in vitro for 24 h and after that cell counting Kit-8 was used to detect cell proliferation. The morphology of HL-60 cells was observed under light and fluorescent microscopy. The early cell apoptosis was detected using flow cytometry with Annexin V/PI double staining. The expressions of Bcl-2, Bax, Caspase-9, Caspase-3 mRNA were analyzed by RT-PCR. The activity of Caspase-9, 3 was examined by chromatometry, ELISA detect Caspase-9, Caspase-3 activity of protein. HL-60 cell proliferation was inhibited significantly by Euphorbiasteroid administration (F=42.97, P<0.001). Comparison between different concentrations, the difference was statistically significant, P<0.05. Early cell apoptosis rate of HL-60 cells was enhanced markedly after Euphorbiasteroid administration (F=56.74, P<0.001), after 10, 20, 40 μg/mL Euphorbiasteroid treatment for 24 h, the HL-60 cells early apoptosis rate respectively were(23.4±3.1)%, (35.7±4.3)%, (53.2±3.9)%, and cells presented typical apoptosis morphological changes. Bax mRNA transcription level increased significantly, the Bcl-2 mRNA transcription level decreased significantly (F=53.45, P<0.001) after Euphorbiasteroid administration in a dose-dependent manner. Caspase-9, Caspase-3 mRNA were up-regulated in the transcriptional level, and a compound dose dependent (F=34.21, P<0.001), semen euphorbiae sterol effect on the HL-60 cells after 24 h Caspase-9, 3 protein activity significantly increased (F=54.33, P<0.001), with the increase of concentration of semen euphorbiae sterol the protein activity increased.
CONCLUSIONS:
Euphorbiasteroid induces HL-60 cells to apoptosis via promoting Bcl-2/Bax apoptotic signaling pathway in a dose-dependent manner.

Euphorbiasteroid Dilution Calculator

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Preparing Stock Solutions of Euphorbiasteroid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8094 mL 9.0472 mL 18.0943 mL 36.1886 mL 45.2358 mL
5 mM 0.3619 mL 1.8094 mL 3.6189 mL 7.2377 mL 9.0472 mL
10 mM 0.1809 mL 0.9047 mL 1.8094 mL 3.6189 mL 4.5236 mL
50 mM 0.0362 mL 0.1809 mL 0.3619 mL 0.7238 mL 0.9047 mL
100 mM 0.0181 mL 0.0905 mL 0.1809 mL 0.3619 mL 0.4524 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 Euphorbiasteroid

Euphorbia factor L1 reverses ABCB1-mediated multidrug resistance involving interaction with ABCB1 independent of ABCB1 downregualtion.[Pubmed:21308736]

J Cell Biochem. 2011 Apr;112(4):1076-83.

Euphorbia factor L1 (EFL1) belongs to diterpenoids of genus Euphorbia. In this article, its reversal activity against ABCB1-mediated MDR in KBv200 and MCF-7/adr cells was reported. However, EFL1 did not alter the sensitivity of KB and MCF-7 cells to chemotherapeutic agents. Meanwhile, EFL1 significantly increased accumulation of doxorubicin and rhodamine 123 in KBv200 and MCF-7/adr cells, showing no significant influence on that of KB and MCF-7 cells. Furthermore, EFL1 could enhance the ATP hydrolysis activity of ABCB1 stimulated by verapamil. At the same time, EFL1 inhibited the efflux of ABCB1 in KBv200 and MCF-7/adr cells. In addition, EFL1 did not downregulate expression of ABCB1 in KBv200 and MCF-7/adr cells either in mRNA or protein level.

Apoptosis sensitization by Euphorbia factor L1 in ABCB1-mediated multidrug resistant K562/ADR cells.[Pubmed:24135937]

Molecules. 2013 Oct 16;18(10):12793-808.

In this article, reversal activities of Euphorbia factor L1 (EFL1) against ABCB1-mediated multidrug resistance (MDR) and apoptosis sensitization in K562/ADR cells are reported. EFL1 decreased the IC50 values of anticancer agents in K562/ADR cells over-expressing ABCB1. However, EFL1 did not affect the IC50 values of anticancer agents in sensitive K562 cells. Additionally, EFL1 increased the intracellular accumulation of rhodamine 123 and doxorubicin in K562/ADR cells without affecting their accumulation in K562 cells. Furthermore, EFL1 sensitized the apoptosis triggered by vincristine in K562/ADR cells via mitochondrial pathway, as confirmed by Annexin V-FITC/PI detection and western blot. At the same time, EFL1 did not influence the apoptosis induced by vincristine in K562 cells. Western blot results showed that EFL1 did not affect the phosphorylation level of AKT and ERK in K562 and K562/ADR cells. Finally, EFL1 did not down-regulate protein expression of ABCB1.

Euphorbiasteroid reverses P-glycoprotein-mediated multi-drug resistance in human sarcoma cell line MES-SA/Dx5.[Pubmed:19960428]

Phytother Res. 2010 Jul;24(7):1042-6.

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.

Euphorbiasteroid, a component of Euphorbia lathyris L., inhibits adipogenesis of 3T3-L1 cells via activation of AMP-activated protein kinase.[Pubmed:25914364]

Cell Biochem Funct. 2015 Jun;33(4):220-5.

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 muM. 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-gamma and CCAAT/enhancer-binding protein alpha, 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.

Description

Euphorbiasteroid is a tricyclic diperpene of Euphorbia lathyris L., inhibits tyrosinase, and increases the phosphorylation of AMPK, with anti-cancer, anti-virus, anti-obesity and multidrug resistance-modulating effect.

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