2. NF-κB Anti-infection Immunology/Inflammation Vitamin D Related/Nuclear Receptor Metabolic Enzyme/Protease
  3. FXR Keap1-Nrf2 Heme Oxygenase (HO) Dengue Virus Bacterial Reactive Oxygen Species (ROS) Estrogen Receptor/ERR Cytochrome P450 Drug Metabolite
  4. (-)-(E)-Guggulsterone

(-)-(E)-Guggulsterone  (Synonyms: (E)-Guggulsterone)

Cat. No.: HY-N7781 Purity: 99.27%
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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.

(-)-(E)-Guggulsterone

(-)-(E)-Guggulsterone Chemical Structure

CAS No. : 39025-24-6

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Based on 1 publication(s) in Google Scholar

Other Forms of (-)-(E)-Guggulsterone:

(-)-(E)-Guggulsterone Related Antibodies

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HO-1 HO-2

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Estrogen receptor ERα ERβ ERRα ERRβ ERRγ

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CYP1 CYP2 CYP3 CYP4 CYP11 CYP17 Aromatase/CYP19A1 CYP26 CYP51 CYP1A2 CYP2D6 CYP2C9 CYP2C19 CYP3A4 CYP17A1

  • Biological Activity

  • Purity & Documentation

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  • Customer Review

Description

(-)-(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].

IC50 & Target[2][4][7]

ERα

 

CYP2C19

2.1 μM (IC50)

CYP2C9

19 μM (IC50)

HO-1

 

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]
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.

(-)-(E)-Guggulsterone Related Antibodies

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[5]
Species Dose Route Indicator value
Rat 18 mg/kg i.v. AUC0-∞ 3.65 μg·h/mL
Rat 50 mg/kg p.o. AUC0-∞ 4.75 μg·h/mL
Rat 18 mg/kg i.v. CL 1.04 L/h
Rat 50 mg/kg p.o. T1/2 (Absorption) 1.06 h
Rat 18 mg/kg i.v. Vd 3.68 L
Rat 50 mg/kg p.o. T1/2 (Elimination) 3.56 h
Rat 50 mg/kg p.o. Tmax 2.50 h
Rat 50 mg/kg p.o. Cmax 0.97 μg/mL
Rat 50 mg/kg p.o. Vd 10.76 L
Rat 50 mg/kg p.o. CL 2.24 L/h
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.
Molecular Weight

312.45

Formula

C21H28O2
CAS No.
Appearance

Solid

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
Structure Classification
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)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.2005 mL 16.0026 mL 32.0051 mL
5 mM 0.6401 mL 3.2005 mL 6.4010 mL
View the Complete Stock Solution Preparation Table

* 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.

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

This equation is commonly abbreviated as: C1V1 = C2V2

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In Vivo:

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

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:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 99.27%

SDS (393 KB)

COA (251 KB) HNMR (249 KB) LCMS (261 KB)

Handling Instructions (2659 KB)
References

Complete Stock Solution Preparation Table

* 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.

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 Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

(-)-(E)-Guggulsterone39025-24-6(E)-GuggulsteroneFXRKeap1-Nrf2Heme Oxygenase (HO)Dengue VirusBacterialReactive Oxygen Species (ROS)Estrogen Receptor/ERRCytochrome P450Drug MetaboliteNR1H4Heme OxygenaseDENVCYPsLiver toxicitySesquiterpeneHuman ovarian cancer cell SKOV3ProliferationCis and trans-guggulsteroneCardiprotective activityAntioxidant propertyIsoproterenol cardiacInhibitorinhibitorinhibit

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