(Z)-Guggulsterone
Synonym(s):(Z)-Guggulsterone;(17Z)-Pregna-4,17(20)-diene-3,16-dione;4,17(20)-trans-Pregnadiene-3,16-dione
- CAS NO.:39025-23-5
- Empirical Formula: C21H28O2
- Molecular Weight: 312.45
- MDL number: MFCD01310757
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-07-29 08:14:47
What is (Z)-Guggulsterone?
Description
Guggulsterone-(Z) (39025-23-5) is a natural steroid from?Commiphora mukul?extract (guggulipid) which lowers cholesterol and acts as an FXR antagonist.1?Attenuates astrocyte-mediated neuroinflammation.2? Induces differentiation of pluripotent stem cells to dopaminergic neurons.3 Produces antidepressant-like effects via activation of the BDNF signaling pathway in mouse models.4
The Uses of (Z)-Guggulsterone
(Z)-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.
The Uses of (Z)-Guggulsterone
Z-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.
What are the applications of Application
Z-Guggulsterone is a selective antagonist of farnesoid X receptor and inhibitor of FXR transactivation.
Definition
ChEBI: Guggulsterone is a 3-hydroxy steroid. It has a role as an androgen.
Biological Activity
Broad spectrum steroid receptor ligand; mineralocorticoid, progesterone and glucocorticoid receptor antagonist (K i values are 37, 224 and 252 nM respectively) and weak androgen receptor agonist (K i = 315 nM). Induces apoptosis in prostate cancer cells and inhibits angiogenesis via suppression of the VEGF-VEGFR2-Akt signalling pathway. Exhibits antilipidemic activity via antagonism of the farnesoid X receptor (FXR) and displays antiseptic, antirheumatic and anti-inflammatory activity in vivo . More active isomer of Guggulsterone (Pregna-4,17(20)-diene-3,16-dione ).
Biochem/physiol Actions
(Z)-Guggulsterone is a natural product that lowers cholesterol due to its function as an antagonist ligand for the bile acid receptor. (Z)-Guggulsterone is a nuclear hormone receptor that regulates the transcription of several genes involved in cholesterol metabolism and plays a role in cholesterol level regulation. (Z)-Guggulsterone is also a selective farnesoid X receptor (FXR) modulator.
storage
Store at RT
References
1) Urizar?et al.?(2002),?A Natural Product That Lowers Cholesterol as an Antagonist Ligand for FXR; Science,?296?1703 2) Liu?et al.?(2018),?Z-Guggulsterone attenuates astrocytes-mediated neuroinflammation after ischemia by inhibiting toll-like receptor 4 pathway; J. Neurochem.,?147?803 3) Agbay?et al.?(2018),?Guggulsterone-releasing Microspheres Direct the Differentiation of Human Induced Pluripotent Stem Cells Into Neural Phenotypes; Biomed. Mater.,?13?034104 4) Liu?et al.?(2017),?Z-Guggulsterone Produces Antidepressant-Like Effects in Mice through Activation of the BDNF Signaling Pathway; Int. J. Neuropsychopharmacol.,?20?485
Properties of (Z)-Guggulsterone
Melting point: | 188-190° |
Boiling point: | 463.3±45.0 °C(Predicted) |
alpha | D26 -61° (c = 1 in chloroform) |
Density | 1.10±0.1 g/cm3(Predicted) |
storage temp. | 2-8°C |
solubility | DMSO: 5 mg/mL |
form | powder |
color | light yellow |
Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. |
Safety information for (Z)-Guggulsterone
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P271:Use only outdoors or in a well-ventilated area. P405:Store locked up. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P501:Dispose of contents/container to..… |
Computed Descriptors for (Z)-Guggulsterone
InChIKey | WDXRGPWQVHZTQJ-OSJVMJFVSA-N |
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Vidgas science and technologies Pvt Ltd
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