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(E)-Guggulsterone

SKU: orb1693621

Description

(E)-Guggulsterone is a stereoisomer of guggulsterone that acts as an FXR antagonist. It has demonstrated lipid-lowering effects, induces heme oxygenase-1, and exhibits antiviral activity by blocking dengue virus (DENV) NS2B/3B protease and replication in vitro.

Research Area

Immunology & Inflammation, Infectious Disease & Virology, Metabolism Research

Images & Validation

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(E)-Guggulsterone

Key Properties

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CAS Number39025-24-6
MW312.45
Purity99.94%
FormulaC21H28O2
SMILES[H][C@@]12CC(=O)\C(=C\C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
TargetROS,Virus Protease,FXR
SolubilityEthanol:1 mg/mL (3.2 mM);DMSO:20 mg/mL (64.01 mM);DMF:10 mg/mL (32.01 mM);DMF:PBS (pH 7.2) (1:4):0.2 mg/mL (0.64 mM)

Bioactivity

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Target IC50
CYP2C9:19 μM|CYP2C19:2.1 μM
In Vivo
In the mouse dengue fever virus (DENV) infection model, (E)-Guggulsterone (5-10 mg/kg, orally administered once on days 1, 3, and 5 post-infection) significantly improved infection-related symptoms . In the rat myocardial ischemia model, (E)-Guggulsterone (50 mg/kg, orally administered once daily for 5 consecutive days) markedly improved biochemical indicators in serum and myocardial tissue .
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In Vitro
In human mammary epithelial MCF10A cells, (E)-Guggulsterone (5–25 μM, 0–12 h) activated the Nrf2 signaling pathway, induced HO-1 expression, and led to a moderate accumulation of intracellular reactive oxygen species (ROS). In Huh-7 cells, (E)-Guggulsterone (0–20 μM, 3 days) exerted potent anti-dengue virus (DENV) activity via activation of the Nrf2/HO-1 pathway and restoration of the antiviral interferon response. (E)-Guggulsterone (3.2 mM, 24 h) exhibited antibacterial activity against both Gram-positive and Gram-negative bacteria (Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa), with inhibition zone diameters of 14 mm, 14 mm, and 11 mm, respectively. In murine and human hepatocytes, (E)-Guggulsterone (1–20 μM) selectively activated estrogen receptor α (Erα) without activating other ERα isoforms, thereby inducing the expression of Cyp3a11 and CYP3A4. (E)-Guggulsterone (5–20 μM) inhibited Cu²⁺-mediated low-density lipoprotein (LDL) lipid peroxidation and reactive oxygen species generation, effectively blocking both enzymatic and non-enzymatic lipid peroxidation processes. (E)-Guggulsterone displayed high plasma protein binding (>96%) in humans, monkeys, rabbits, and rats, and could promote the oxidative metabolism of liver microsomes. (E)-Guggulsterone showed moderate inhibitory effects on CYP2C19, CYP2C8, CYP2C9, and CYP2B6, with half-maximal inhibitory concentrations (IC₅₀) of 2.1, 6.0, 19, and 22 μM, respectively; whereas it exerted weak inhibition on CYP1A2, CYP2A6, CYP2D6, CYP2E1, and CYP3A4 (IC₅₀ > 50 μM).
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Storage & Handling

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Storagekeep away from direct sunlight,keep away from moisture | Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
Expiration Date12 months from date of receipt.
DisclaimerFor research use only

Alternative Names

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(E) Guggulsterone, (E)Guggulsterone, (-)-(E)-Guggulsterone, Guggulsterone

Similar Products

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  • Guggulsterone

    Guggulsterone [orb1301679]

    99.80%

    95975-55-6

    312.45

    C21H28O2

    25 mg, 1 mg, 1 ml x 10 mM (in DMSO), 200 mg, 5 mg, 10 mg, 50 mg, 100 mg
  • (E)-Guggulsterone (Standard)

    (E)-Guggulsterone (Standard) [orb3140931]

    39025-24-6

    312.45

    C21H28O2

    10 mg
Quality Guarantee

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Compound Identifiers

PubChem CID
6439929 ↗

Key Properties

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No computed properties available.

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(E)-Guggulsterone (orb1693621)

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% DMSO +
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% Tween 80 +
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1 mg
$ 90.00
5 mg
$ 140.00
10 mg
$ 180.00
1 ml x 10 mM (in DMSO)
$ 190.00
25 mg
$ 270.00
50 mg
$ 380.00
100 mg
$ 540.00
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