Epiberberine

Modify Date: 2024-01-02 19:13:26

Epiberberine Structure
Epiberberine structure
Common Name Epiberberine
CAS Number 6873-09-2 Molecular Weight 336.36
Density N/A Boiling Point N/A
Molecular Formula C20H18NO4+ Melting Point 260ºC
MSDS N/A Flash Point N/A

 Use of Epiberberine


Epiberberine is an alkaloid isolated from Coptis chinensis, acts as a potent AChE and BChE inhibitor, and a non-competitive BACE1 inhibitor, with IC50s of 1.07, 6.03 and 8.55 μM, respectively. Epiberberine has antioxidant activity, with peroxynitrite ONOO- scavenging effect (IC50, 16.83 μM), and may protect against Alzheimer disease[1]. Epiberberine inhibits the early stage of differentiation of 3T3-L1 preadipocytes, downregulates the Raf/MEK1/2/ERK1/2 and AMPKα/Akt pathways[2]. Epiberberine has the potential effect in the research of diabetic disease[3].

 Names

Name Epiberberine
Synonym More Synonyms

 Epiberberine Biological Activity

Description Epiberberine is an alkaloid isolated from Coptis chinensis, acts as a potent AChE and BChE inhibitor, and a non-competitive BACE1 inhibitor, with IC50s of 1.07, 6.03 and 8.55 μM, respectively. Epiberberine has antioxidant activity, with peroxynitrite ONOO- scavenging effect (IC50, 16.83 μM), and may protect against Alzheimer disease[1]. Epiberberine inhibits the early stage of differentiation of 3T3-L1 preadipocytes, downregulates the Raf/MEK1/2/ERK1/2 and AMPKα/Akt pathways[2]. Epiberberine has the potential effect in the research of diabetic disease[3].
Related Catalog
Target

IC50: 1.07 μM (AChE), 6.03 μM (BChE), 8.55 μM (BACE1)[2]

In Vitro Epiberberine (0, 12.5, 25, or 50 μM) dose-dependently inhibits cellular triglyceride accumulation in 3T3-L1 adipocytes, with an IC50 of 52.8 μM[2]. Epiberberine (12.5-50 μM) suppresses the Raf/MEK1/ERK1/2 and AMPKα/Akt pathways in the early stage of 3T3-L1 adipocyte differentiation[2]. Epiberberine (0.2, 1, 5 μg/mL) inhibits glucose uptake in HepG2 cells in a concentration-dependent manner[3].
In Vivo Epiberberine (225 mg/kg, p.o. daily for 40 days) reduces body weight, food consumption, water intake, and urinary output of KK-Ay mice[3].
References

[1]. Jung HA, et al. Anti-Alzheimer and antioxidant activities of Coptidis Rhizoma alkaloids. Biol Pharm Bull. 2009 Aug;32(8):1433-8.

[2]. Choi JS, et al. Anti-adipogenic effect of epiberberine is mediated by regulation of the Raf/MEK1/2/ERK1/2 and AMPKα/Akt pathways. Arch Pharm Res. 2015 Dec;38(12):2153-62.

[3]. Ma H, et al. Antihyperglycemia and Antihyperlipidemia Effect of Protoberberine Alkaloids From Rhizoma Coptidis in HepG2 Cell and Diabetic KK-Ay Mice. Drug Dev Res. 2016 Jun;77(4):163-70.

 Chemical & Physical Properties

Melting Point 260ºC
Molecular Formula C20H18NO4+
Molecular Weight 336.36
PSA 40.80000
LogP -0.99
Storage condition 2-8C

 Synonyms

HMS2229E04
Benz(a)-1,3-benzodioxolo(4,5-g)quinolizinium,11,12-dihydro-8,9-dimethoxy
GNF-Pf-2355
epiberberinium
8,9-dimethoxy-11,12-dihydro-[1,3]dioxolo[4,5-h]isoquino[2,1-b]isoquinolinylium
Benz(a)-1,3-benzodioxolo(4,5-g)quinolizinium, 11,12-dihydro-8,9-dimethoxy-
8,9-Dimethoxy-11,12-dihydro[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-13-ium
Benzo[a]-1,3-benzodioxolo[4,5-g]quinolizinium, 11,12-dihydro-8,9-dimethoxy-
pseudo-Epiberberin
Epiberberin
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