| Identification | Back Directory | [Name]
(Z)-Guggulsterone | [CAS]
39025-23-5 | [Synonyms]
GUGULSTERONE
GUGGULSTERONE
GUGGULSTERONE Z
Z-Gugglesterone
GUGGULESTERONE Z
CIS GUGGULSTERONE
(Z)-Guggulsterone
GUGGULSTERONE Z(P)
GUGGULSTERONE (Z FORM)
Guggulsterone Z (25 mg)
PREGNA-4,17(20)-DIENE-3,16-DIONE
CIS-4,17(20)-PREGNADIENE-3,16-DIONE
4,17(20)-(CIS)-PREGNADIEN-3,16-DIONE
(Z)-Pregna-4,17(20)-diene-3,16-dione
(17Z)-Pregna-4,17(20)-diene-3,16-dione
Pregna-4,17(20)-diene-3,16-dione, (17Z)-
(17Z)-Pregna-4,17(20)-diene-3,16-dione, 4,17(20)-cis-Pregnadiene-3,16-dione | [Molecular Formula]
C21H28O2 | [MDL Number]
MFCD01310757 | [MOL File]
39025-23-5.mol | [Molecular Weight]
312.45 |
| Chemical Properties | Back Directory | [Melting point ]
188-190° | [alpha ]
D26 -61° (c = 1 in chloroform) | [Boiling point ]
463.3±45.0 °C(Predicted) | [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. | [InChI]
InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4+/t15-,17+,18+,20+,21-/m1/s1 | [InChIKey]
WDXRGPWQVHZTQJ-OSJVMJFVSA-N | [SMILES]
C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)/C(=C/C)/C(=O)C3)CC2 | [LogP]
3.650 (est) |
| Hazard Information | Back Directory | [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 | [Uses]
Z-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent. | [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 |
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