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Bavachin estrogen receptors ERα and ERβ activator

Catalog No.C4895
Size Price Stock Qty
5mg
$115.00
In stock
10mg
$210.00
In stock

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Sample solution is provided at 25 µL, 10mM.

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Chemical structure

Bavachin

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Chemical Properties

Cas No. 19879-32-4 SDF Download SDF
Synonyms Corylifolin
Chemical Name (2S)-2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
Canonical SMILES OC1=CC(O[[email protected]](C2=CC=C(O)C=C2)CC3=O)=C3C=C1C/C=C(C)/C
Formula C20H20O4 M.Wt 324.4
Solubility ≤20mg/ml in ethanol;30mg/ml in DMSO;50mg/ml in dimethyl formamide Storage Store at -20°C
Physical Appearance A crystalline solid Shipping Condition Evaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Background

Bavachin is an acyl-coenzyme A: cholesterol acyltransferase inhibitor [1].

Acyl-coenzyme A: cholesterol acyl transferase (ACAT) is an enzyme responsible for the intracellular esterification of free cholesterol with fatty acids and plays dominant roles in intestinal absorption of cholesterol, hepatic production of lipoproteins and accumulation of cholesteryl ester within macrophages and smooth muscle cells. [1].

Bavachin showed a significant inhibition of ACAT enzyme. The IC50 value of bavachin was 86.0 μM in the ACAT assay system using rat liver microsome [1]. Bavachin is a flavonoid first isolated from Psoralea corylifolia that has been used as a traditional medicine in Asia. In CV-1 cells transfected with plasmids ERα or ERβ, bavachin showed ER ligand binding activity with an EC50 of 320 nM and 680 nM, respectively. Bavachin increased the mRNA levels of estrogen-responsive genes such as pS2 and PR, and decreased the protein level of ERα by proteasomal pathway [2]. Bavachin activated gene expression of proliferator-activated receptorγ (PPARγ), adipogenic transcriptional factors, and CCAAT/enhancer binding protein-α (C/EBPα). Bavachin increased adiponectin expression and secretion in adipocytes. Bavachin increased insulin-induced glucose uptake by differentiated adipocytes and myoblasts. In differentiated adipocytes, bavachin enhanced glucose uptake [3].

References:
[1] Choi J H, Rho M C, Lee S W, et al.  Bavachin and isobavachalcone, acyl-coenzyme A: cholesterol acyltransferase inhibitors from Psoralea corylifolia[J]. Archives of pharmacal research, 2008, 31(11): 1419-1423.
[2] Park J, Kim D H, Ahn H N, et al.  Activation of estrogen receptor by bavachin from Psoralea corylifolia[J]. Biomolecules & therapeutics, 2012, 20(2): 183-188.
[3] Lee H, Li H, Noh M, et al.  Bavachin from Psoralea corylifolia improves insulin-dependent glucose uptake through insulin signaling and AMPK activation in 3T3-L1 adipocytes[J]. International journal of molecular sciences, 2016, 17(4): 527.