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Obtusifoliol

$2,880

  • Brand : BIOFRON

  • Catalogue Number : BN-O1842

  • Specification : 98%(HPLC)

  • CAS number : 16910-32-0

  • Formula : C30H50O

  • Molecular Weight : 426.7

  • PUBCHEM ID : 65252

  • Volume : 20mg

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Quantity
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Catalogue Number

BN-O1842

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

426.7

Appearance

Botanical Source

Structure Type

Category

SMILES

Synonyms

IUPAC Name

(3S,4S,5S,10S,13R,14R,17R)-4,10,13,14-tetramethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,5,6,7,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol

Applications

Density

0.98g/cm3

Solubility

Flash Point

221.9ºC

Boiling Point

501.3ºC at 760mmHg

Melting Point

InChl

InChl Key

MMNYKQIDRZNIKT-VSADUBDNSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:16910-32-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

27534104

Abstract

Fifteen semisynthetic terpenoid derivatives from the major latex components of Euphorbia officinarum have been evaluated against the insect pest Spodoptera littoralis, two species of protozoan parasites, Trypanosoma cruzi and Leishmania infantum, and also against insect Sf9 and mammalian CHO cells to test their selective cytotoxicity. Our results showed that 40% of the test substances were postingestive toxicants to S. littoralis. All the tested derivatives had cytotoxic effects on insect-derived Sf9 cells, whereas mammalian CHO cells were affected by a lower number of compounds (47%). Furthermore, 87% of the test compounds had antiparasitic effects on both L. infantum and T. cruzi, with some of them being selective parasite toxicants.

Title

New Bioactive Semisynthetic Derivatives of 31-Norlanostenol and Obtusifoliol from Euphorbia officinarum

Author

Maria Bailen, Mourad Daoubi Khamlichi, Ahmed Benharref, Rafael A Martinez-Diaz, Azucena Gonzalez-Coloma

Publish date

2016 Jun;

PMID

27474490

Abstract

From the aerial parts of Euphorbia sogdiana Popov, obtusifoliol (1) and two related steroids (2-3) have been isolated and characterized along with a known cycloartane derivative (4). The chemical structure of the obtusifoliol-related compounds, obtained by 1D and 2D NMR, and MS measurements, have been determined as: 3β,7α-dihydroxy-4α,14α-dimethyl-5α-ergosta-8,24(28)-diene-11-one (2) and 3β-hydroxy-4α,14α-dimethyl-5α-ergosta-8,24(28)-diene-1-one (3). Compound 2 has been previously isolated from Euphorbia chamaesyce while compound 3 was never reported before. The isolated compounds 1-4 were subjected to cytotoxic tests on the breast cancer cells, MCF-7 and MDA-MB231. Further pharmacological tests on the more active compounds 2 and 3 indicated their action to be related to cell growth inhibitory activity and apoptotic effects on the tested cells.

KEYWORDS

4α-Methyl sterols; Anticancer; Apoptosis; Breast cancer; Euphorbia sogdiana; Obtusifoliol analogues.

Title

Obtusifoliol related steroids from Euphorbia sogdiana with cell growth inhibitory activity and apoptotic effects on breast cancer cells (MCF-7 and MDA-MB231)

Author

Mahmoud Aghaei 1, Zeinab Yazdiniapour 2, Mustafa Ghanadian 3, Behzad Zolfaghari 2, Virginia Lanzotti 4, Vahid Mirsafaee 2

Publish date

2016 Nov;

PMID

27313059

Abstract

Rapidly multiplying cancer cells synthesize greater amounts of cholesterol to build their membranes. Cholesterol-lowering drugs (statins) are currently in clinical trials for anticancer chemotherapy. However, given at higher doses, statins cause serious side effects by inhibiting the formation of other biologically important molecules derived from mevalonate. Sterol 14α-demethylase (CYP51), which acts 10 steps downstream, is potentially a more specific drug target because this portion of the pathway is fully committed to cholesterol production. However, screening a variety of commercial and experimental inhibitors of microbial CYP51 orthologs revealed that most of them (including all clinical antifungals) weakly inhibit human CYP51 activity, even if they display high apparent spectral binding affinity. Only one relatively potent compound, (R)-N-(1-(3,4′-difluorobiphenyl-4-yl)-2-(1H-imidazol-1-yl)ethyl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide (VFV), was identified. VFV has been further tested in cellular experiments and found to decrease proliferation of different cancer cell types. The crystal structures of human CYP51-VFV complexes (2.0 and 2.5 a) both display a 2:1 inhibitor/enzyme stoichiometry, provide molecular insights regarding a broader substrate profile, faster catalysis, and weaker susceptibility of human CYP51 to inhibition, and outline directions for the development of more potent inhibitors.

KEYWORDS

X-ray crystallography; cancer; cholesterol; cholesterol/biosynthesis; drug therapy/hypolipidemic drugs; cytochrome P450; enzymology/enzyme mechanisms; inhibition; membranes.

Title

Human sterol 14α-demethylase as a target for anticancer chemotherapy: towards structure-aided drug design

Author

Tatiana Y Hargrove 1, Laura Friggeri 1, Zdzislaw Wawrzak 2, Suneethi Sivakumaran 1, Eugenia M Yazlovitskaya 3, Scott W Hiebert 1, F Peter Guengerich 1, Michael R Waterman 1, Galina I Lepesheva 4

Publish date

2016 Aug;