Euphol

Specifications / Handling

More Information
Product Details
Synonyms	Euphadienol; α-Euphol; NSC 36571; Eupha-8,24-dienol; 5α-Eupha-8,24-dien-3β-ol; (+)-Eupha-8,24-dien-3β-ol; (+)-Euphol
Product Type	Chemical
Properties
Formula	C₃₀H₅₀O
MW	426.7
CAS	514-47-6
Source/Host Chemicals	Isolated from Euphorbia resinifera.
Purity Chemicals	≥98% (HPLC)
Appearance	White powder.
Solubility	Soluble in DMSO, methanol or ethanol (all 5-10mg/ml). Insoluble in water.
Identity	Determined by ¹H-NMR.
InChi Key	CAHGCLMLTWQZNJ-WZLOIPHISA-N
Smiles	C[C@H](CC/C=C(C)/C)[C@]1([H])CC[C@]([C@@]1(C)CC2)(C)C3=C2[C@]4(C)[C@](CC3)([H])C(C)(C)[C@@H](O)CC4
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Euphol is a euphane-type triterpene alcohol that is structurally similar to cholesterol and has a wide range of pharmacological properties, including anticancer, anti-inflammatory, analgesic, antiviral and immunomodulatory effects.
Euphol produces anti-inflammatory effects by mediating NF-κB, down-regulation of tumor necrosis factor-α and cyclooxygenase-2 and reduced activation of protein kinase C.
Euphol inhibits the monoacylglycerol lipase (MAGL) activity via a reversible mechanism (IC50=315nM). MAGL inhibition in the periphery modulates the endocannabinoid system to block the development of inflammatory pain.
Euphol exerted in vitro and in vivo cytotoxicity against several cancer cell lines and glioma cells, through several cancer pathways, including inhibition of proliferation, motility and colony formation, arresting the cell cycle, induction of apoptosis by modulation of ERK signaling and the activation of autophagy-associated cell death. Euphol, either as a single agent or in combination with conventional chemotherapy, is a potential anticancer drug.
Euphol suppressed TGF-β signaling by inducing TGF-β receptor movement into lipid-raft microdomains and degrading TGF-β receptors.
Euphol has also shown to consistently reduce and limit the severity and development of experimental autoimmune encephalomyelitis (EAE) which is an established model of Multiple sclerosis (MS).
Euphol exerts antiviral effects by inhibiting reverse transcriptase in purified human immunodeficiency virus type 1.
Euphol was applied in silico as an inhibitor the of SARS-CoV-2 main protease (MPro monomer, 6m03). Euphol interacts with Phe8, Val297, Arg298 and Val303 residues of the main protease. Virulence of SARS-CoV-2 is dependend on the main protease responsible for virus replication along with many major functions. Therefore, Euphol might have potential as a COVID-19 drug.

Product References

Inhibitory effect of euphol, a triterpene alcohol from the roots of Euphorbia kansui, on tumour promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin: K. Yasukawa, et al.; J. Pharm. Pharmacol. 52, 119 (2000)
Inhibitory Effects of Triterpenoids and Sterols on Human Immunodeficiency Virus-1 Reverse Transcriptase: T. Akihisa, et al.; Lipids 36, 507 (2001)
Eupha-7,9(11),24-trien-3alpha-ol (Antiquol C) and Other Triterpenes from Euphorbia antiquorum Latex and Their Inhibitory Effects on Epstein-Barr Virus Activation: T. Akihisa, et al.; J. Nat. Prod. 65, 158 (2002)
Discovery of potent and reversible monoacylglycerol lipase inhibitors: A.R. King, et al.; Chem. Biol. 16, 1045 (2009)
Euphol, a tetracyclic triterpene produces antinociceptive effects in inflammatory and neuropathic pain: the involvement of cannabinoid system: R.C. Dutra, et al.; Neuropharmacol. 63, 593 (2012)
Euphol prevents experimental autoimmune encephalomyelitis in mice: evidence for the underlying mechanisms: R.C. Dutra, et al.; Biochem. Pharmacol. 83, 531 (2012)
Euphol from Euphorbia tirucalli selectively inhibits human gastric cancer cell growth through the induction of ERK1/2-mediated apoptosis: M.W. Lin, et al.; Food Chem. Toxicol. 50, 4333 (2012)
The role of PKC/ERK1/2 signaling in the anti-inflammatory effect of tetracyclic triterpene euphol on TPA-induced skin inflammation in mice: G.F. Passos, et al.; Eur. J. Pharmacol. 698, 413 (2013)
Euphol arrests breast cancer cells at the G1 phase through the modulation of cyclin D1, p21 and p27 expression: L. Wang, et al.; Mol. Med. Rep. 8, 1279 (2013)
Euphol from Euphorbia tirucalli Negatively Modulates TGF-β Responsiveness via TGF-β Receptor Segregation inside Membrane Rafts: C.-L. Chen, et al.; PLoS One 10, e0140249 (2015)
The antinociceptive effects of the tetracyclic triterpene euphol in inflammatory and neuropathic pain models: The potential role of PKCε: R.C. Dutra, et al.; Neurosci. 303, 126 (2015)
Euphorbia tirucalli L.: Review on morphology, medicinal uses, phytochemistry and pharmacological activities: Asian Pac. J. Trop. Biomed. 7, 603 (2017)
Pharmacokinetics and cytotoxic study of euphol from Euphorbia umbellata (Bruyns) Pax latex: L.S. Cruz, et al.; Phytomedicine 47, 105 (2018)
In vitro screening of cytotoxic activity of euphol from Euphorbia tirucalli on a large panel of human cancer-derived cell lines: V.A. Oliveira Silva, et al.; Exp. Ther. Med. 16, 557 (2018)
Euphol, a tetracyclic triterpene, from Euphorbia tirucalli induces autophagy and sensitizes temozolomide cytotoxicity on glioblastoma cells: V.A. Oliveira Silva, et al.; Invest. New Drugs 37, 1029 (2019)
Coronavirus disease 2019 drug discovery through molecular docking: S. Singh & H. Florez; F1000Res 9, 502 (2020)

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