Guggulsterone

Guggulsterone

E-Guggulsterone
Z-Guggulsterone
Names
IUPAC name (8R,9S,10R,13S,14S)-17-Ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
Other names Pregna-4,17-diene-3,16-dione
Identifiers
CAS Number	95975-55-6 (E/Z) 39025-24-6 (E) 39025-23-5 (Z)
ChEMBL	ChEMBL410683
IUPHAR/BPS	2745
Jmol interactive 3D	(E): Image (Z): Image
PubChem	6439929 (E) 6450278 (Z)
SMILES (E): O=C1C[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]2(C)/C1=C\C)=O (Z): O=C1C[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]2(C)/C1=C/C)=O
Properties
Chemical formula	C21H28O2
Molar mass	312.45 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

References

1. Szapary, PO; Wolfe, ML; Bloedon, LT; Cucchiara, AJ; Dermarderosian, AH; Cirigliano, MD; Rader, DJ (2003). "Guggulipid Ineffective for Lowering Cholesterol". JAMA 290 (6): 765–772. doi:10.1001/jama.290.6.765. PMID 12915429.
2. Sahni, S; Hepfinger, CA; Sauer, KA (2005). "Guggulipid Use in Hyperlipidemia". Am J Health-Syst Pharm 62 (16): 1690–1692. doi:10.2146/ajhp040580. PMID 16085931.