A farnesoid X receptor antagonist
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(E)-Guggulsterone

Item No. 10011296

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
pregna-4-17(20)-diene-3,16-dione
CAS Number
39025-24-6
Molecular Formula
C21H28O2
Formula Weight
312.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:4): 0.2 mg/mlDMSO: 0.25 mg/mlEthanol: 1 mg/ml
SMILES
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
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
InChi Key
WDXRGPWQVHZTQJ-OSJVMJFVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

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    10 mg

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    25 mg

    $775

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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 antagonist ligand for FXR. Science 296(5573), 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. The Journal of Biological Chemisty 278(12), 10214-10220 (2003).