Euphol

CAS# 514-47-6

Euphol

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Chemical structure

Euphol

3D structure

Chemical Properties of Euphol

Cas No. 514-47-6 SDF Download SDF
PubChem ID 441678 Appearance Powder
Formula C30H50O M.Wt 426.71
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S,5R,10S,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
SMILES CC(CCC=C(C)C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C
Standard InChIKey CAHGCLMLTWQZNJ-WZLOIPHISA-N
Standard InChI InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22+,25+,26+,28-,29+,30-/m1/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 Euphol

The sap of Euphorbia tirucalli.

Biological Activity of Euphol

Description1. Euphol, a novel cannabinoid agonist, prevents inflammatory and neuropathic persistent pain in rodents. 2. Euphol arrests breast cancer cells at the G1 phase through the modulation of cyclin D1, p21 and p27 expression. 3. Euphol has anti-inflammatory action, it can prevent experimental autoimmune encephalomyelitis in mice.
TargetsNOS | TNF-α | COX | CDK | p21 | IL Receptor

Euphol Dilution Calculator

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Euphol Molarity Calculator

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Preparing Stock Solutions of Euphol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3435 mL 11.7176 mL 23.4351 mL 46.8702 mL 58.5878 mL
5 mM 0.4687 mL 2.3435 mL 4.687 mL 9.374 mL 11.7176 mL
10 mM 0.2344 mL 1.1718 mL 2.3435 mL 4.687 mL 5.8588 mL
50 mM 0.0469 mL 0.2344 mL 0.4687 mL 0.9374 mL 1.1718 mL
100 mM 0.0234 mL 0.1172 mL 0.2344 mL 0.4687 mL 0.5859 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 Euphol

Euphol arrests breast cancer cells at the G1 phase through the modulation of cyclin D1, p21 and p27 expression.[Pubmed:23969579]

Mol Med Rep. 2013 Oct;8(4):1279-85.

Euphorbia tirucalli is a longestablished treatment for a wide variety of cancers. However, the mechanism of its anticancer effect is yet to be elucidated. In the present study, we examined the anticancer effect of Euphol, a tetracyclic triterpene alcohol isolated from the sap of Euphorbia tirucalli, in T47D human breast cancer cells. Following the treatment of cells with different doses of Euphol for 24, 48 and 72 h, the cell proliferation, cell cycle, and mRNA and protein levels of cell cycle regulatory molecules were analyzed, respectively. Treatment of the cells with Euphol resulted in decreased cell viability, which was accompanied by an accumulation of cells in the G1 phase. Further studies demonstrated that Euphol treatment downregulated cyclin D1 expression and the hypophosphorylation of Rb. Furthermore, this effect was correlated with the downregulation of cyclindependent kinase 2 (CDK2) expression and the upregulation of the CDK inhibitors p21 and p27. Reduced expression levels of cyclin A and B1 were also observed, corresponding to the decreased distribution of cells in the S and G2/M phases, respectively. These findings indicated that Euphol is an active agent in Euphorbia tirucalli that exerts anticancer activity by arresting the cell cycle of cancer cells.

Euphol, a tetracyclic triterpene produces antinociceptive effects in inflammatory and neuropathic pain: the involvement of cannabinoid system.[Pubmed:22613837]

Neuropharmacology. 2012 Sep;63(4):593-605.

Persistent pains associated with inflammatory and neuropathic states are prevalent and debilitating diseases, which still remain without a safe and adequate treatment. Euphol, an alcohol tetracyclic triterpene, has a wide range of pharmacological properties and is considered to have anti-inflammatory action. Here, we assessed the effects and the underlying mechanisms of action of Euphol in preventing inflammatory and neuropathic pain. Oral treatment with Euphol (30 and 100 mg/kg) reduced carrageenan-induced mechanical hyperalgesia. Likewise, Euphol given through the spinal and intracerebroventricular routes prevented mechanical hyperalgesia induced by carrageenan. Euphol consistently blocked the mechanical hyperalgesia induced by complete Freund's adjuvant, keratinocyte-derived chemokine, interleukin-1beta, interleukin-6 and tumor necrosis factor-alpha associated with the suppression of myeloperoxidase activity in the mouse paw. Oral treatment with Euphol was also effective in preventing the mechanical nociceptive response induced by ligation of the sciatic nerve and also significantly reduced the levels and mRNA of cytokines/chemokines in both paw and spinal cord tissues following i.pl. injection of complete Freund's adjuvant. In addition, the pre-treatment with either CB(1)R or CB(2)R antagonists, as well as the knockdown gene of the CB(1)R and CB(2)R, significantly reversed the antinociceptive effect of Euphol. Interestingly, even in higher doses, Euphol did not cause any relevant action in the central nervous system. Considering that few drugs are currently available for the treatment of chronic pain states, the present results provided evidence that Euphol constitutes a promising molecule for the management of inflammatory and neuropathic pain states.

Euphol prevents experimental autoimmune encephalomyelitis in mice: evidence for the underlying mechanisms.[Pubmed:22155310]

Biochem Pharmacol. 2012 Feb 15;83(4):531-42.

Multiple sclerosis (MS) is a severe chronic T cell-mediated autoimmune inflammatory disease of the central nervous system (CNS), the existing therapy of which is only partially effective and is associated with undesirable side effects. Euphol, an alcohol tetracyclic triterpene, has a wide range of pharmacological properties and is considered to have anti-inflammatory action. However there are no reports about the effects and mechanisms of Euphol in experimental autoimmune encephalomyelitis (EAE), an established model of MS. Here we report the effects and the underlying mechanisms of action of Euphol in EAE. Euphol (1-10mg/kg) was administered orally at different time-points of EAE. Immunological and inflammatory responses were evaluated by real-time PCR, Western blot and flow cytometry assays. We provide evidence that Euphol significantly attenuates neurological signs of EAE. These beneficial effects of Euphol seem to be associated with the down-regulation of mRNA and protein expression of some pro-inflammatory mediators such as TNF-alpha, inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in the CNS. Furthermore, in vitro, Euphol consistently inhibited the T cell-mediated immune response including the production of T(H)1 and T(H)17 cytokines in spleen cells of untreated EAE animals. Likewise, oral Euphol treatment inhibited the infiltration of T(H)17 myelin-specific cells into the CNS through the adhesion molecule, lymphocyte function-associated antigen 1 (LFA-1). Our findings reveal that oral administration of Euphol consistently reduces and limits the severity and development of EAE. Therefore, Euphol might represent a potential molecule of interest for the treatment of MS and other T(H)17 cell-mediated inflammatory diseases.

Description

Euphol is a tetracyclic triterpene alcohol isolated from the sap of Euphorbia tirucalli with anti-mutagenic, anti-inflammatory and immunomodulatory effects, orally active. Euphol inhibits the monoacylglycerol lipase (MGL) activity via a reversible mechanism (IC50=315 nM). MGL inhibition in the periphery modulates the endocannabinoid system to block the development of inflammatory pain.

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