(Z)-Guggulsterone

(Z)-Guggulsterone Property

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)

Safety

Hazard Codes 

Xi

Risk Statements 

37-38

Safety Statements 

36

WGK Germany 

3

HS Code 

2914299000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

(Z)-Guggulsterone Chemical Properties,Usage,Production

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.

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] NANCY L. URIZAR. A Natural Product That Lowers Cholesterol As an Antagonist Ligand for FXR[J]. Science, 2002, 296 5573. DOI:10.1126/science.1072891
[2] TIANLONG LIU. Z-Guggulsterone attenuates astrocytes-mediated neuroinflammation after ischemia by inhibiting toll-like receptor 4 pathway[J]. Journal of Neurochemistry, 2018, 147 6: 803-815. DOI:10.1111/jnc.14583
[3] ANDREW AGBAY. Guggulsterone-releasing microspheres direct the differentiation of human induced pluripotent stem cells into neural phenotypes.[J]. Biomedical materials (Bristol, England), 2018, 13 3: 034104. DOI:10.1088/1748-605x/aaaa77
[4] FENG-GUO LIU. Z-Guggulsterone Produces Antidepressant-Like Effects in Mice through Activation of the BDNF Signaling Pathway.[J]. International Journal of Neuropsychopharmacology, 2017, 20 6: 485-497. DOI:10.1093/ijnp/pyx009