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Euphol

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-E4009

  • Specification : 98%(HPLC)

  • CAS number : 514-47-6

  • Formula : C30H50O

  • Molecular Weight : 426.73

  • PUBCHEM ID : 441678

  • Volume : 25mg

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Catalogue Number

BF-E4009

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

426.73

Appearance

White powder

Botanical Source

Euphorbia kansui

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(CCC=C(C)C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C

Synonyms

13α,14β,17βH-Lanosta-8,24-dien-3β-ol (8CI)/Euphadienol/(3β,13α,14β,17α)-Lanosta-8,24-dien-3-ol/5α-Eupha-8,24-dien-3β-ol/Euphol, Euphadienol/euphol/Lanosta-8,24-dien-3-ol, (3β,13α,14β,17α)-

IUPAC 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

Density

1.0±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate

Flash Point

221.1±20.7 °C

Boiling Point

498.9±44.0 °C at 760 mmHg

Melting Point

116-117ºC

InChl

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

InChl Key

CAHGCLMLTWQZNJ-WZLOIPHISA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:514-47-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29931585

Abstract

Glioblastoma (GBM) is the most frequent and aggressive type of brain tumor. There are limited therapeutic options for GBM so that new and effective agents are urgently needed. Euphol is a tetracyclic triterpene alcohol, and it is the main constituent of the sap of the medicinal plant Euphorbia tirucalli. We previously identified anti-cancer activity in euphol based on the cytotoxicity screening of 73 human cancer cells. We now expand the toxicological screening of the inhibitory effect and bioactivity of euphol using two additional glioma primary cultures. Euphol exposure showed similar cytotoxicity against primary glioma cultures compared to commercial glioma cells. Euphol has concentration-dependent cytotoxic effects on cancer cell lines, with more than a five-fold difference in the IC50 values in some cell lines. Euphol treatment had a higher selective cytotoxicity index (0.64-3.36) than temozolomide (0.11-1.13) and reduced both proliferation and cell motility. However, no effect was found on cell cycle distribution, invasion and colony formation. Importantly, the expression of the autophagy-associated protein LC3-II and acidic vesicular organelle formation were markedly increased, with Bafilomycin A1 potentiating cytotoxicity. Finally, euphol also exhibited antitumoral and antiangiogenic activity in vivo, using the chicken chorioallantoic membrane assay, with synergistic temozolomide interactions in most cell lines. In conclusion, euphol exerted in vitro and in vivo cytotoxicity against glioma cells, through several cancer pathways, including the activation of autophagy-associated cell death. These findings provide experimental support for further development of euphol as a novel therapeutic agent for GBM, either alone or in combination chemotherapy.

KEYWORDS

Anticancer; Cytotoxic activity and euphol; Glioblastoma

Title

Euphol, a tetracyclic triterpene, from Euphorbia tirucalli induces autophagy and sensitizes temozolomide cytotoxicity on glioblastoma cells.

Author

Silva VAO1, Rosa MN1, Miranda-Goncalves V2,3, Costa AM2,3, Tansini A1, Evangelista AF1, Martinho O1,2,3, Carloni AC1, Jones C4,5, Lima JP6, Pianowski LF7, Reis RM8,9,10.

Publish date

2019 Apr

PMID

30166094

Abstract

BACKGROUND:
Medicinal plants are an important source to identify new active pharmaceutical compounds. Traditionally, the sap of Euphorbia umbellata is widely used to treat cancer and inflammatory conditions. These effects have been attributed to the presence of terpenes and phenolic compounds in the extracts of this plant. Euphol, a tetracyclic triterpene alcohol, is one of the major compounds present in Euphorbia species, and some biological activities have been attributed to this compound.

PURPOSE:
This study aimed to evaluate the in vitro cytotoxicity of euphol against Jurkat, HL-60, K-562, B16F10, and HRT-18 cells lines, as well as the biological stability, distribution, metabolism properties in vitro, and the determination of the concentration of euphol in the plasma and liver of rats.

METHODS:
The MTT reduction assay was used to evaluate the cytotoxicity of euphol against cancer cell lines, and the selectivity index, the morphology and cell cycle assays to evaluate the death mechanisms in K-562 and B16F10 lineages. UHPLC-MS was applied for the in vivo evaluation of the concentration of euphol in plasma and liver, and in vitro metabolic stability in human liver microsomes and S9 fraction, plasma protein binding, and stability in simulated gastric and intestinal fluids assays.

CONCLUSIONS:
This study demonstrated that euphol exhibited cytotoxic effects against a variety of cancer cells lines, selectivity against leukemia and possibly, the mechanism involved is apoptosis. The evaluation of stability, distribution, and metabolism properties showed that euphol was unstable in gastric and intestinal fluids, presenting moderate plasma protein binding with two hours elimination half-life and possible phase II liver metabolism. All the results suggested that further studies could be developed to prove the viability of euphol as an anticancer agent.

Copyright © 2018 Elsevier GmbH. All rights reserved.

KEYWORDS

Cell culture; Cytotoxic activity; Euphol; Euphorbia; Pharmacokinetics; UHPLC-MS

Title

Pharmacokinetics and cytotoxic study of euphol from Euphorbia umbellata (Bruyns) Pax latex.

Author

Cruz LS1, de Oliveira TL2, Kanunfre CC3, Paludo KS3, Minozzo BR1, Prestes AP1, Wang M4, Fernandes D1, Santos FAD5, Manda VK4, Khan SI4, Ali Z4, de Messias-Reason IJ2, Avula B4, Khan IA4, Beltrame FL6.

Publish date

2018 Aug 1

PMID

30112023

Abstract

A large number of classic antineoplastic agents are derived from plants. Euphorbia tirucalli L. (Euphorbiaceae) is a subtropical and tropical plant, used in Brazilian folk medicine against many diseases, including cancer, yet little is known about its true anticancer properties. The present study evaluated the antitumor effect of the tetracyclic triterpene alcohol, euphol, the main constituent of E. tirucalli in a panel of 73 human cancer lines from 15 tumor types. The biological effect of euphol in pancreatic cells was also assessed. The combination index was further used to explore euphol interactions with standard drugs. Euphol showed a cytotoxicity effect against several cancer cell lines (IC50 range, 1.41-38.89 µM), particularly in esophageal squamous cell (11.08 µM) and pancreatic carcinoma cells (6.84 µM), followed by prostate, melanoma, and colon cancer. Cytotoxicity effects were seen in all cancer cell lines, with more than half deemed highly sensitive. Euphol inhibited proliferation, motility and colony formation in pancreatic cancer cells. Importantly, euphol exhibited synergistic interactions with gemcitabine and paclitaxel in pancreatic and esophageal cell lines, respectively. To the best of our knowledge, this study constitutes the largest in vitro screening of euphol efficacy on cancer cell lines and revealed its in vitro anti-cancer properties, particularly in pancreatic and esophageal cell lines, suggesting that euphol, either as a single agent or in combination with conventional chemotherapy, is a potential anti-cancer drug.

KEYWORDS

Euphorbia tirucalli; anticancer; cytotoxic activity; esophageal; euphol; pancreatic

Title

In vitro screening of cytotoxic activity of euphol from Euphorbia tirucalli on a large panel of human cancer-derived cell lines.

Author

Silva VAO1, Rosa MN1, Tansini A1, Oliveira RJS1, Martinho O1,2,3, Lima JP4, Pianowski LF5, Reis RM1,2,3.

Publish date

2018 Aug


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[1].