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Guggulsterone E&Z

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-G2008

  • Specification : 98%

  • CAS number : 95975-55-6

  • Formula : C21H28O2

  • Molecular Weight : 312.453

  • PUBCHEM ID : 6450278

  • Volume : 20mg

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Catalogue Number

BF-G2008

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

312.453

Appearance

Powder

Botanical Source

herbs of Ailanthus grandis

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

C/C=C/1C(=O)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

Synonyms

Z-Guggulsterone/Cis-Guggulsterone/Neuropeptide W-23 (human)/CIS GUGGULSTERONE/GUGGULSTERONE Z(P)/GUGGULSTERONE, (Z)-/E-guggulsterone/Z-Gugglesterone/GUGGULSTERONE Z/(4,17(20)t)-Pregnadien-3,16-dion/Guggulsterone Z (25 mg)/Guggulsterone/GUGGULESTERONE Z/Pregna-4,17(20)-diene-3,16-dione, (17Z)-/(17Z)-Pregna-4,17-diene-3,16-dione/4,17(20)-Z-pregnadiene-3,16-dione/GUGGULSTERONE (Z FORM)/GUGULSTERONE/Pregna-4,17-diene-3,16-dione, (17Z)-/Z-Guggulsteron

IUPAC Name

(8R,9S,10R,13S,14S,17Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione

Density

1.1±0.1 g/cm3

Solubility

Soluble to 10 mM in ethanol with gentle warming

Flash Point

172.3±25.7 °C

Boiling Point

463.3±45.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4+

InChl Key

WDXRGPWQVHZTQJ-AYSLTRBKSA-N

WGK Germany

RID/ADR

HS Code Reference

2937290000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:95975-55-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

16250653

Abstract

Guggulsterone 1, the active principle of guggulipid, has been used in ethnic medicine for thousands of years for its antinflammatory and antilipidemic activities. The activities of 1 are apparently mediated by its interaction with an array of nuclear receptors, including endocrine steroid receptors and metabolic lipid receptors. Although relatively weak, the activity at the metabolic farnesoid X receptor (FXR) is particularly intriguing, as 1 is, so far, the only antagonist known for this receptor, with a peculiar ability of gene selective modulation. We report here a systematic study aimed at identifying the potential binding pocket of 1 at FXR. Although 1 could be docked into the canonical binding site, we identified a novel, so far undescribed binding pocket, localized near the loop region between helix 1 and helix 2. This novel binding pocket may explain some of the peculiar characteristics of 1 when acting at FXR.

Title

Is antagonism of E/Z-guggulsterone at the farnesoid X receptor mediated by a noncanonical binding site? A molecular modeling study.

Author

Meyer U1, Costantino G, Macchiarulo A, Pellicciari R.

Publish date

2005 Nov 3

PMID

15351045

Abstract

A sensitive, selective, precise and robust high-performance thin-layer chromatographic method of analysis of E and Z stereoisomers of guggulsterone (the hypolipidemic agent in the gum-resin exudates of Commiphora mukul) both as a bulk drug and in formulations was developed and validated. The method employed TLC aluminium plates precoated with silica gel 60F-254 as the stationary phase. The solvent system consisted of toluene-acetone (9:1, v/v). Densitometric analysis of guggulsterone was carried out in the absorbance mode at 250 nm. This system was found to give compact spots for E- and Z-guggulsterone (Rf value of 0.38 +/- 0.02 and 0.46 +/- 0.02, respectively) following double development of chromatoplates with the same mobile phase. The linear regression analysis data for the calibration plots for E- and Z-guggulsterone showed good linear relationship with r2 = 0.9977 +/- 0.054 and 0.9975 +/- 0.068, respectively, in the concentration range of 100-6000 ng/spot. The mean value of slope and intercept were 0.11 +/- 0.006 and 0.11 +/- 0.005, 14.26 +/- 0.56 and 10.92 +/- 0.76, respectively, for E- and Z-guggulsterone. The method was validated for precision, robustness and recovery. The limit of detection and quantitation were 12, 10 and 24, 20 ng/spot, respectively, for E- and Z-guggulsterone. Statistical analysis proves that the method is repeatable and selective for the estimation of the said drug. Since the proposed mobile phase effectively resolves the E- and Z-isomers of guggulsterone, this HPTLC method can be applied for identification and quantitation of these isomers in herbal extracts and pharmaceutical dosage form.

Title

HPTLC method for guggulsterone. I. Quantitative determination of E- and Z-guggulsterone in herbal extract and pharmaceutical dosage form.

Author

Agrawal H1, Kaul N, Paradkar AR, Mahadik KR.

Publish date

2004 Sep 21

PMID

11234828

Abstract

Guggulipid, the standardized product from the extraction of the ole-gum-resin from the Commiphora mukul plant, has been marketed as a hypolipidemic agent. The ketosteroids, cis- and trans-4,17(20)-pregnadiene-3,16-dione, known as E- and Z-guggulsterones, respectively, are the main ingredients in guggulipid. A liquid chromatographic method was developed for simultaneous determination of E- and Z-guggulsterones in guggulipid preparations using synthetic E- and Z-guggulsterone standards. Realtively low amounts of guggulsterones (E and Z) were found in commercial guggulipid preparations in comparison with the manufacturer’s claim of 2.5%. The mixture of E- and Z-guggulsterones was extracted and separated on a Symmetry C18 reversed-phase column, with a mobile phase of acetonitrile–water (46 + 54, v/v) and detected at 242 nm. The retention times of E- and Z-guggulsterones are approximately 8 and 11 min, respectively. Assay quantitation was based on the calibration curve obtained from a mixture of synthetic standard E- and Z-guggulsterones. Experimental data on selectivity, linearity, accuracy, and recoveries are presented.

Title

Simultaneous determination of E- and Z-guggulsterones in dietary supplements containing Commiphora mukul extract (guggulipid) by liquid chromatography.

Author

Nagarajan M1, Waszkuc TW, Sun J.

Publish date

2001 Jan-Feb


Description :

Guggulsterone is a plant sterol derived from the gum resin of the tree Commiphora wightii. Guggulsterone inhibits the growth of a wide variety of tumor cells and induces apoptosis through down regulation of antiapoptotic gene products (IAP1, xIAP, Bfl-1/A1, Bcl-2, cFLIP and survivin), modulation of cell cycle proteins (cyclin D1 and c-Myc), activation of caspases and JNK, inhibition of Akt[1]. Guggulsterone, a farnesoid X receptor (FXR) antagonist, decreases CDCA-induced FXR activation with IC50s of 17 and 15 μM for Z- and E-Guggulsterone, respectively[2].