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Guggulsterone E&Z

Names

[ CAS No. ]:
95975-55-6

[ Name ]:
Guggulsterone E&Z

[Synonym ]:
Z-Guggulsterone
Cis-Guggulsterone
Neuropeptide W-23 (human)
CIS GUGGULSTERONE
GUGGULSTERONE Z(P)
GUGGULSTERONE, (Z)-
E-guggulsterone
Z-Gugglesterone
GUGGULSTERONE Z
(4,17(20)t)-Pregnadien-3,16-dion
Guggulsterone Z (25 mg)
Guggulsterone
GUGGULESTERONE Z
Pregna-4,17(20)-diene-3,16-dione, (17Z)-
MFCD01310757
(17Z)-Pregna-4,17-diene-3,16-dione
4,17(20)-Z-pregnadiene-3,16-dione
GUGGULSTERONE (Z FORM)
GUGULSTERONE
UNII:6CST3U34GN
Pregna-4,17-diene-3,16-dione, (17Z)-
Z-Guggulsteron

Biological Activity

[Description]:

Guggulsterone is a plant sterol derived from the gum resin of the tree Commiphora wightii. Guggulsterone inhibits the growth of a wide variety of tumor cells and induces apoptosis through down regulation of antiapoptotic gene products (IAP1, xIAP, Bfl-1/A1, Bcl-2, cFLIP and survivin), modulation of cell cycle proteins (cyclin D1 and c-Myc), activation of caspases and JNK, inhibition of Akt[1]. Guggulsterone, a farnesoid X receptor (FXR) antagonist, decreases CDCA-induced FXR activation with IC50s of 17 and 15 μM for Z- and E-Guggulsterone, respectively[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Metabolic Enzyme/Protease >> FXR
Signaling Pathways >> Apoptosis >> Caspase
Signaling Pathways >> PI3K/Akt/mTOR >> Akt
Signaling Pathways >> MAPK/ERK Pathway >> JNK

[Target]

JNK

Akt

Caspase


[In Vitro]

Guggulsterone (0.5-20 μM; 24 hours) suppresses TREM-1, TLR4 and TNF-α expression as well as the phosphorylation of IκBα and NF-κB p65 by LPS[2]. Western Blot Analysis[1] Cell Line: RAW 264.7 murine macrophage cells Concentration: 0.5, 5, 10, 20 μM Incubation Time: 24 hours Result: Suppressed TREM-1, TLR4, and TNF-α expression as well as the phosphorylation of IκBα and NF-κB p65 by LPS.

[In Vivo]

Guggulsterone (orally; 100 mg/kg once per day for 8 days) significantly improved the survival rates of wild-type mice with TNBS-induced colitis[2]. Animal Model: Wild-type mice with TNBS-induced colitis[2] Dosage: 100 mg/kg Administration: Orally; once per day; for 8 days Result: Improved the survival rates of wild-type mice with TNBS-induced colitis.

[References]

[1]. Shishodia S, et al. Guggulsterone for Chemoprevention of Cancer. Curr Pharm Des. 2016;22(3):294-306.

[2]. Che X, et al. Protective effects of guggulsterone against colitis are associated with the suppression of TREM-1 and modulation of macrophages. Am J Physiol Gastrointest Liver Physiol. 2018 Jul 1;315(1):G128-G139.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
463.3±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C21H28O2

[ Molecular Weight ]:
312.446

[ Flash Point ]:
172.3±25.7 °C

[ Exact Mass ]:
312.208923

[ PSA ]:
34.14000

[ LogP ]:
3.65

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.557

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: 5 mg/mL

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R37

[ Safety Phrases ]:
S36

[ WGK Germany ]:
3

Related Compounds