(E)-Guggulsterone

Cayman Chemical Item Number 10011296

(CAS 39025-24-6)

(E)-Guggulsterone (CAS 39025-24-6)

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Description

Bile acids are essential for solubilization and transport of dietary lipids, are the major products of cholesterol catabolism, and are physiological ligands for farnesoid X receptor (FXR), a nuclear receptor that regulates genes involved in lipid metabolism.1 They are also inherently cytotoxic, as physiological imbalance contributes to increased oxidative stress.2,3 Bile acid-controlled signaling pathways are promising novel targets to treat such metabolic diseases as obesity, type II diabetes, hyperlipidemia, and atherosclerosis. Guggulsterone, derived from resin of the guggul tree, is a competitive antagonist of FXR both in vitro and in vivo.4 The cis stereoisomer of guggulsterone, (E)-guggulsterone, decreases chenodeoxycholic acid (CDCA)-induced FXR activation with an IC50 value of 15 µM. 5,6 By inhibiting CDCA-induced transactivation of FXR, guggulsterone lowers low-density lipoprotein cholesterol and triglyceride levels in rodents fed a high cholesterol diet.4

1 Makishima, M., Okamoto, A.Y., Repa, J.J., et al. Identification of a nuclear receptor for bile acids. Science 284 1362-1365 (1999).

2 Barbier, O., Torra, I.P., Sirvent, A., et al. FXR induces the UGT2B4 enzyme in hepatocytes: A potential mechanism of negative feedback control of FXR activity. Gastroenterology 124 1926-1940 (2003).

3 Tan, K.P., Yang, M., and Ito, S. Activation of nuclear factor (erythroid-2 like) factor 2 by toxic bile acids provokes adaptive defense responses to enhance cell survival at the emergence of oxidative stress. Mol Pharmacol 72(5) 1380-1390 (2007).

4 Urizar, N.L., Liverman, A.B., Dodds, D.T., et al. A natural product that lowers cholesterol as an anatagonist ligand for FXR.. Science 296 1703-1706 (2002).

5 Cui, J., Huang, L., Zhao, A., et al. Guggulsterone is a farnesoid X receptor antagonist in coactivator association assays but acts to enhance transcription of bile salt export pump. J Biol Chem 278(12) 10214-10220 (2003).

6 Wu, J., Xia, C., Meier, J., et al. The hypolipidemic natural product guggulsterone acts as an antagonist of the bile acid receptor. Mol Endocrinol 16(7) 1590-1597 (2002).

Formal Name pregna-​4-​17(20)-​diene-​3,​16-​dione
CAS Number 39025-24-6
Molecular Formula C21H28O2
Formula Weight 312.5
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C1CC[C@@]​2(C)​C(CC[C@]​3([H]​)​[C@]​2([H]​)​CC[C@@]​4(C)​[C@@]​3([H]​)​CC(/C4=C\C)​=O)​=C1
InCHI Code
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​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
InCHI Key
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WDXRGPWQVHZTQJ-OSJVMJFVSA-N

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Size Price Quantity Subtotal
1 mg $112.00 $0.00
5 mg $504.00 $0.00
10 mg $896.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-16. Prices are subject to change without notice.

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