(-) - (E) -Guggulsterone

(-) - (E) -Guggulsterone ((E) -Guggulsterone) is an orally active natural stereoisomer of Guggulsterone (HY-107738) . (-) - (E) -Guggulsterone is an antagonist for the Farnesoid X Receptor (FXR) with an IC50 of 24.06 μM and possesses potent hypolipidemic properties. (-) - (E) -Guggulsterone suppresses dengue virus (DENV) replication by upregulating antiviral interferon responses by inducing HO-1 expression via Nrf2 activation. (-) - (E) -Guggulsterone exhibits antibacterial activities against Bacillus subtilis, Staphylococcus aureus and Pseudomonas aeruginosa. (-) - (E) -Guggulsterone has cardiac protective and antioxidant activities in rats[1][2][3][4][5][6].

Product Specifications

CAS Number

[39025-24-6]

Product Name Alternative

(E) -Guggulsterone

UNSPSC

12352211

Hazard Statement

H335

Target

Bacterial; Cytochrome P450; Dengue Virus; Drug Metabolite; Estrogen Receptor/ERR; FXR; Heme Oxygenase (HO) ; Keap1-Nrf2; Reactive Oxygen Species (ROS)

Type

Natural Products

Related Pathways

Anti-infection; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB; Vitamin D Related/Nuclear Receptor

Applications

Metabolism-sugar/lipid metabolism

Field of Research

Infection; Endocrinology; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/minus-e-guggulsterone.html

Purity

99.19

Solubility

DMSO : 25 mg/mL (ultrasonic; warming; heat to 60°C)

Smiles

C/C=C1C(C[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]/12C)=O)=O

Molecular Formula

C21H28O2

Molecular Weight

312.45

Precautions

H335

References & Citations

[1]N. VERMA, et al. Pharmacokinetics of Guggulsterone after Intravenous and Oral Administration in Rats.|[2]Almazari I, et al. Guggulsterone induces heme oxygenase-1 expression through activation of Nrf2 in human mammary epithelial cells: PTEN as a putative target. Carcinogenesis. 2012 Feb;33 (2) :368-76. |[3]Chen WC, et al. (E) -Guggulsterone Inhibits Dengue Virus Replication by Upregulating Antiviral Interferon Responses through the Induction of Heme Oxygenase-1 Expression. Viruses. 2021 Apr 20;13 (4) :712. |[4]Choudhary MI, et al. Fungal metabolites of (E) -guggulsterone and their antibacterial and radical-scavenging activities. Chem Biodivers. 2005 Apr;2 (4) :516-24. |[5]Brobst DE, et al. Guggulsterone activates multiple nuclear receptors and induces CYP3A gene expression through the pregnane X receptor. J Pharmacol Exp Ther. 2004 Aug;310 (2) :528-35.|[6]Chander R, et al. Cardioprotective activity of synthetic guggulsterone (E and Z-isomers) in isoproterenol induced myocardial ischemia in rats: A comparative study. Indian J Clin Biochem. 2003 Jul;18 (2) :71-9. |[7]Hsu CW, et al. Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor. Sci Rep. 2014 Sep 26;4:6437.|[8]Chhonker YS, et al. In-vitro metabolism, CYP profiling and metabolite identification of E- and Z- guggulsterone, a potent hypolipidmic agent. J Pharm Biomed Anal. 2018 Oct 25;160:202-211.