Cat. No.: HY-N7781

(-)-(E)-Guggulsterone

(Synonyms: (E)-Guggulsterone)

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(-)-(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.

For research use only. We do not sell to patients.

Purity: 99.19%
CAS No.: 39025-24-6
Formula: C₂₁H₂₈O₂
Molecular Weight:312.45

Storage:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

(-)-(E)-Guggulsterone Chemical Structure

CAS No.: 39025-24-6

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Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- Parmacokinetics
- In Vivo
Chemical Information
Solvent & Solubility
- In Vitro
- In Vivo
Purity & Documentation
References
Help & FAQs
Bioz

Biological Activity

Description

IC₅₀ & Target^[2]^[4]^[7]

ERα

CYP2C19

2.1 μM (IC₅₀)

CYP2C9

19 μM (IC₅₀)

HO-1

All Heme Oxygenase (HO) Isoforms :

HO-1
HO-2

All Estrogen Receptor/ERR Isoforms :

All Cytochrome P450 Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
CV-1	IC₅₀	4.1 μM Compound: E-guggulsterone	Antagonist activity at human FXR expressed in monkey CV1 cells after 24 hrs by ecdysone receptor response element-driven luciferase reporter assay Antagonist activity at human FXR expressed in monkey CV1 cells after 24 hrs by ecdysone receptor response element-driven luciferase reporter assay	[PMID: 17988093]
CV-1	IC₅₀	44 μM Compound: (E)-guggulsterone	Antagonist activity at human FXR expressed in CV-1 cells assessed as inhibition of CDCA-induced transactivation after 24 hrs by luciferase reporter gene assay Antagonist activity at human FXR expressed in CV-1 cells assessed as inhibition of CDCA-induced transactivation after 24 hrs by luciferase reporter gene assay	[PMID: 21142112]
HEK293	IC₅₀	41 μM Compound: E-guggulsterone	Antagonist activity at human FXR expressed in HEK293 cells assessed as inhibition of GW4064-induced transactivation after 24 hrs by luciferase reporter gene assay Antagonist activity at human FXR expressed in HEK293 cells assessed as inhibition of GW4064-induced transactivation after 24 hrs by luciferase reporter gene assay	[PMID: 26821210]
PANC-1	IC₅₀	>100 μM Compound: E-GS	Cytotoxicity against human PANC1 cells incubated in normal DMEM medium Cytotoxicity against human PANC1 cells incubated in normal DMEM medium	[PMID: 32057581]

In Vitro

(-)-(E)-Guggulsterone (5-25 μM, 0-12 h) induces activation of Nrf2 signaling and the subsequent HO-1 expression and the modest increase in the intracellular accumulation of ROS in human mammary epithelial MCF10A cells^[1].
(-)-(E)-Guggulsterone (0-20 μM, 3 days) exerts potent anti-DENV activity through a unique mechanism involving Nrf2/HO-1 pathway activation and restoration of antiviral interferon responses in Huh-7 cells^[2].
(-)-(E)-Guggulsterone (3.2 mM, 24 h) exhibits antibacterial activities against Bacillus subtilis, Staphylococcus aureus and Pseudomonas aeruginosa with inhibition zones of 14 mm, 14 mm and 11 mm^[3].
(-)-(E)-Guggulsterone (1-20 μM) activates ERα, but does not activate the ERα isoform and induces the expression of Cyp3a11 and CYP3A4 in mouse hepatocytes and human hepatocytes^[4].
(-)-(E)-Guggulsterone (5-20 μM) inhibits the Cu²⁺ mediated lipid peroxidation of LDL and the formation of oxygen free radicals in concentration dependent manner, in both enzymic and non-enzymic systems makes microsomes less susceptible against oxidative degradation of their lipids^[6].
(-)-(E)-Guggulsterone exhibits plasma protein binding in human, monkey, rabbit and rat plasma was greater than 96% and promotes oxidative metabolism in liver microsomes^[7].
(-)-(E)-Guggulsterone exhibits inhibition against CYP2C19, CYP2C8, CYP2C9 and CYP2B6 with IC₅₀s of 2.1, 6.0, 19 and 22 μM, and week inhibition against CYP1A2, CYP2A6, CYP2D6, CYP2E1 and CYP3A4 with IC₅₀s all > 50 μM^[7].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

RT-PCR^[1]

Cell Line:

MCF10A cells
Concentration:

25 μM
Incubation Time:

0, 1, 3, 6, 9, 12 h
Result:

Induced the messenger RNA transcript of HO-1 in a time-dependent manner.

Immunofluorescence^[1]

Cell Line:

MCF10A cells
Concentration:

5, 10, 25 μM
Incubation Time:

6 h
Result:

Confirmed the increased nuclear localization of Nrf2.

Western Blot Analysis^[1]

Cell Line:

MCF10A cells
Concentration:

5, 10, 25 μM
Incubation Time:

0, 1, 3, 6, 9, 12 h
Result:

Increased HO-1 expression in a concentration- and time-dependent manner.
Showed significantly greater potency than Z-guggulsterone at all concentrations.
Increased the nuclear translocation of Nrf2 in 1 h.
Dose- and time-dependently increased Nrf2-ARE binding.

RT-PCR^[2]

Cell Line:

Huh-7 cells
Concentration:

0, 2.5, 5, 10 and 20 μM
Incubation Time:

3 days after infection
Result:

Decreased the mRNA level of DENV and increased the mRNA level of HO-1.
Increased IFN-α2, IFN-α5 and IFN-α17.

Western Blot Analysis^[2]

Cell Line:

Huh-7 cells
Concentration:

0, 2.5, 5, 10 and 20 μM
Incubation Time:

3 days after infection
Result:

Dose-dependently induced HO-1 protein.
Increased cytoplasmic Nrf2 expression.
Dose-dependently inhibited NS2B/NS3 protease.

Parmacokinetics

Species	Dose	Route	AUC_0-∞	CL	V_d	T_1/2 (Absorption)	T_1/2 (Elimination)	T_max	C_max
Rat^[5]	18 mg/kg	i.v.	3.65 μg·h/mL	1.04 L/h	3.68 L	/	/	/	/
Rat^[5]	50 mg/kg	p.o.	4.75 μg·h/mL	2.24 L/h	10.76 L	1.06 h	3.56 h	2.50 h	0.97 μg/mL

In Vivo

(-)-(E)-Guggulsterone (5-10 mg/kg, i.p., once at 1, 3, and, 5 days post-infection) improves the symptoms of DENV infection in mice^[2].
(-)-(E)-Guggulsterone (50 mg/kg, p.o., once daily for five days) significantly reverses the biochemical parameters in serum and hearts in myocardial ischemia rats model^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Anti-DENV Activity model established in six-day-old ICR suckling mice^[2]
Dosage:

5 and 10 mg/kg
Administration:

Intraperitoneal injection (i.p.), at 1, 3, and, 5 days post-infection
Result:

Reached 60% survival rate in the 10 mg/kg.
Decreased the viral load in the brain by 10 times.
Maintained weight.
Increased the expression of HO-1 and IFN-α in the brain.

Animal Model:

Myocardial ischemia model established in male Chades Foster rats, each animal weighing 200-225g^[6]
Dosage:

50 mg/kg
Administration:

Oral administration (p.o.), once daily for five days
Result:

Reduced CPK (creatine phosphokinase) and transaminases (GOT/GPT).
Restored the activity of Ca-ATPase and glycogen levels, and reduced phospholipase and lipid peroxides.

Chemical Information

CAS No. 39025-24-6
Appearance Solid
Molecular Weight 312.45
Formula C₂₁H₂₈O₂
Color White to off-white
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
Synonyms

(E)-Guggulsterone
Structure Classification
- Steroids
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 25 mg/mL (80.01 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.2005 mL

16.0026 mL

32.0051 mL

5 mM

0.6401 mL

3.2005 mL

6.4010 mL

10 mM

0.3201 mL

1.6003 mL

3.2005 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Dilution Calculator

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2 mg/mL (6.40 mM); Clear solution

This protocol yields a clear solution of ≥ 2 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (286 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. 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. [Content Brief]

[2]. 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. [Content Brief]

[3]. Choudhary MI, et al. Fungal metabolites of (E)-guggulsterone and their antibacterial and radical-scavenging activities. Chem Biodivers. 2005 Apr;2(4):516-24. [Content Brief]

[4]. 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. [Content Brief]

[5]. N. VERMA, et al. Pharmacokinetics of Guggulsterone after Intravenous and Oral Administration in Rats.

[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. [Content Brief]

[7]. 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. [Content Brief]

[8]. 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. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	3.2005 mL	16.0026 mL	32.0051 mL	80.0128 mL
	5 mM	0.6401 mL	3.2005 mL	6.4010 mL	16.0026 mL
	10 mM	0.3201 mL	1.6003 mL	3.2005 mL	8.0013 mL
	15 mM	0.2134 mL	1.0668 mL	2.1337 mL	5.3342 mL
	20 mM	0.1600 mL	0.8001 mL	1.6003 mL	4.0006 mL
	25 mM	0.1280 mL	0.6401 mL	1.2802 mL	3.2005 mL
	30 mM	0.1067 mL	0.5334 mL	1.0668 mL	2.6671 mL
	40 mM	0.0800 mL	0.4001 mL	0.8001 mL	2.0003 mL
	50 mM	0.0640 mL	0.3201 mL	0.6401 mL	1.6003 mL
	60 mM	0.0533 mL	0.2667 mL	0.5334 mL	1.3335 mL
	80 mM	0.0400 mL	0.2000 mL	0.4001 mL	1.0002 mL

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(-)-(E)-Guggulsterone

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All Heme Oxygenase (HO) Isoforms

All Estrogen Receptor/ERR Isoforms

All Cytochrome P450 Isoforms

Biological Activity

Chemical Information

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

(-)-(E)-Guggulsterone Related Classifications

Cat. No.: HY-N7781