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Ergosterol

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-E1009

  • Specification : 98%

  • CAS number : 57-87-4

  • Formula : C28H44O

  • Molecular Weight : 396.65

  • PUBCHEM ID : 444679

  • Volume : 20mg

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Catalogue Number

BF-E1009

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

396.65

Appearance

Off-white crystalline powder

Botanical Source

Astrocladus coniferus,Ganoderma duropora,Lentinula edodes,Peristrophe japonica,Shiraia bambusicola

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C

Synonyms

Ergosterol/(24R)-Ergosta-5,7,22-trien-3b-ol/(3S,9S,10R,13R,14R,17R)-17-[(2R,3E,5R)-5,6-Dimethyl-3-hepten-2-yl]-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol/PROVITAMIN D2/ERGOSTERINE/(22E)-Ergosta-5,7,22-trien-3β-ol/ERGOSTERIN/Ergosta-5,7,22-trien-3β-ol/PROVITAMINE D2/(3β)-Ergosta-5,7,22-trien-3-ol/(3b,22E)-Ergosta-5,7,22-trien-3-ol/Ergosta-5,7,22-trien-3-ol, (3β,22E)-/(3β,2E)-Ergosta-5,7,22-trien-3-ol/provitamind/(3β,22E)-Ergosta-5,7,22-trien-3-ol/Ergosta-5:6,7:8,22:23-trien-3-ol

IUPAC Name

(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol

Density

1.0±0.1 g/cm3

Solubility

Chloroform

Flash Point

216.3±19.3 °C

Boiling Point

501.5±39.0 °C at 760 mmHg

Melting Point

156-158 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2936900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:57-87-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31124408

Abstract

Background: This is the first report demonstrating the antibiotic-modifying activity of cholecalciferol.

AIM:
In this study, cholecalciferol was evaluated against multiresistant strains of Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli.

METHODS:
The antibacterial and modulatory effects of cholecalciferol, ergosterol, and cholesterol (8-512 μg/mL) were evaluated by microdilution assay against multiresistant bacterial strains.

RESULTS:
Cholecalciferol, when combined with aminoglycosides, was more effective against P. aeruginosa, reducing the concentration of amikacin and gentamicin necessary to inhibit bacterial growth from 156.25 to 39.06 μg/mL and from 39.06 to 9.76 μg/mL, respectively. It is possible that cholecalciferol, due to its lipid-soluble nature, had a lipophilic interaction with the cell membrane, enhancing antibiotic uptake. Cholesterol and ergosterol were used to see if the mechanism of action of cholecalciferol was similar to that of these lipid compounds. Ergosterol and cholesterol increased aminoglycoside activity, where the effect was greater with higher subinhibitory concentration of sterol.

CONCLUSIONS:
There is no reported study on the use of cholesterol and ergosterol as modulators of antibiotics or any other drug, making this the first study in this area highlighting the interaction between cholesterol, ergosterol, and cholecalciferol with regard to modifying aminoglycoside activity.

KEYWORDS

Cholecalciferol; aminoglycosides; antibiotic-modifying; bacterial resistance; lipid solubility

Title

Cholecalciferol, Ergosterol, and Cholesterol Enhance the Antibiotic Activity of Drugs.

Author

Andrade JC1, Morais Braga MFB1, Guedes GMM1, Tintino SR1, Freitas MA1, Quintans LJ1, Jr2, Menezes IRA1, Coutinho HDM1.

Publish date

2018 Dec

PMID

32154942

Abstract

RATIONALE:
In the field of natural products, dereplication of complex mixtures hasbecomes usual practice to annotate known compounds and avoid their re-isolation. To this purpose, many groups rely on liquid chromatography coupled to high resolution mass spectrometry to deduce molecular formulae of compounds allowing comparison with public or in-house databases. Electrospray ionisation is usually considered as the method of choice to investigate a large panel of compounds but, in some cases, it may lead to unusual results as described in the following article for ergosterol.

METHODS:
Ergosterol and other fungal sterols in methanolic solution were analysed using different chromatographic gradients by HPLC/MS on both IT-TOFMS and Orbitrap-MS instruments fitted with an ESI source. Further flow injection analyses were performed to investigate the influence of the solvent composition. MS/MS fragmentation data were acquired to annotate the different ions observed.

RESULTS:
Contrary to other fungal sterols, ergosterol was found to be highly sensitive to oxidation during electrospray ionisation. Putative structures were proposed based on MS/MS studies and known oxidation mechanisms of ergosterol by reactive oxygen species (ROS) that could be formed in the ESI process. The proportion of acetonitrile in the eluent was found to influence this in-source oxidation, with increased proportion of oxidized sodium adducts with higher proportions of acetonitrile.

CONCLUSIONS:
While ergosterol is a major sterol found in fungi, this study investigates its ionisation by electrospray for the first time. The results reported here will help further detection and annotation of this compound in fungal extracts after HPLC/ESI-MS analyses.

This article is protected by copyright. All rights reserved.

Title

Detection of ergosterol by liquid chromatography/electrospray mass spectrometry - investigation of unusual in source reactions.

Author

Ory L1, Gentil E1,2, Kumla D3, Kijjoa A3, Nazih EH1, Roullier C1,2.

Publish date

2020 Mar 10

PMID

32146854

Abstract

Androgen-dependent LNCaP and androgen-independent DU-145 cells, were treated with different concentrations of ergosterol (15 µM and 25 µM) and its respective cell viability was measured by MTT bioassay. While ergosterol showed an antiproliferative effect on LNCaP, on DU-145 promoted cell proliferation. This differential effect suggests that the effect of ergosterolmight be related to its ability to act as an Androgen Receptor ligand. In silico Molecular Dynamics simulations were performed to analyze the interaction mechanism between androgen receptor and ergosterol, in comparison with natural ligands, 5α-dihydrotestosterone and testosterone. Our model suggests that the binding of androgen receptor with ergosterol is thermodinamically feasible, which is concordant with our experimental results.

KEYWORDS

Androgen receptor; DU-145; LNCaP; MTT bioassay; ergosterol; molecular dynamics simulations

Title

Ergosterol exerts a differential effect on AR-dependent LNCaP and AR-independent DU-145 cancer cells.

Author

MuNoz-Fonseca MB1, Vidal-Limon A2, Fernandez-Pomares C3, Rojas-Duran F3, Hernandez-Aguilar ME3, Espinoza C4, Trigos A4, Suarez-Medellin J1.

Publish date

2020 Mar 9


Description :

Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.