Guggulsterone

Title: Guggulsterone
CAS Registry Number: 95975-55-6
CAS Name: Pregna-4,17(20)-diene-3,16-dione
Molecular Formula: C21H28O2
Molecular Weight: 312.45
Percent Composition: C 80.72%, H 9.03%, O 10.24%
Literature References: Bioactive component in guggulu, q.v., the gum resin of the Ayurvedic medicinal plant, Commiphora mukul, Burseraceae, used in treatment of lipid disorders. Both the E- and Z- isomers are naturally occurring and bioactive. Synthesis and stereochemistry: W. R. Benn, R. M. Dodson, J. Org. Chem. 29, 1142 (1964). Isoln from guggulu: V. D. Patil et al., Tetrahedron 28, 2341 (1972). HPLC determn of isomers in serum: N. Verma et al., J. Chromatogr. B 708, 243 (1998). LC determn of isomers in commercial guggulu formulations: M. Nagarajan et al., J. AOAC Int. 84, 24 (2001). Inhibition of the bile acid receptor FXR and cholesterol lowering activity: N. L. Urizar et al., Science 296, 1703 (2002). Brief review of proposed mechanism of action: C. J. Sinal, F. J. Gonzalez, Trends Endocrinol. Metab. 13, 275-276 (2002).
Derivative Type: E-Form
CAS Registry Number: 39025-24-6
Properties: Prisms from aq methanol, mp 170-171.5°. [a]D26 -30° (c = 1 in chloroform). uv max (methanol): 241 nm (e 27600).
Melting point: mp 170-171.5°
Optical Rotation: [a]D26 -30° (c = 1 in chloroform)
Absorption maximum: uv max (methanol): 241 nm (e 27600)
Derivative Type: Z-Form
CAS Registry Number: 39025-23-5
Properties: Crystals from aq methanol, mp 188-190°. [a]D26 -61° (c = 1 in chloroform). uv max (methanol): 241 nm (e 25000).
Melting point: mp 188-190°
Optical Rotation: [a]D26 -61° (c = 1 in chloroform)
Absorption maximum: uv max (methanol): 241 nm (e 25000)
Guggulu Guinea Green B Gum Benzoin Gum Tragacanth Gusperimus

Guggulsterone
Guggulsterone E.png
E-Guggulsterone
Guggulsterone Z.png
Z-Guggulsterone
Identifiers
CAS number 95975-55-6 (E/Z) YesY, 39025-24-6 (E) YesY, 39025-23-5 (Z) YesY
PubChem 6439929 (E), 6450278 (Z)
ChEMBL CHEMBL410683 N
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C21H28O2
Molar mass 312.45 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Guggulsterone is a plant steroid found in the resin of the guggul plant, Commiphora mukul. Guggulsterone can exist as either of two stereoisomers, E-guggulsterone and Z-guggulsterone. In humans, it acts as an antagonist of the farnesoid X receptor, which was once believed to result in decreased cholesterol synthesis in the liver. Several studies have been published that indicate no overall reduction in total cholesterol occurs using various dosages of guggulsterone, and levels of low-density lipoprotein ("bad cholesterol") increased in many people.[1][2] Nevertheless, guggulsterone is an ingredient in many nutritional supplements.