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Epiberberine

Names

[ CAS No. ]:
6873-09-2

[ Name ]:
Epiberberine

[Synonym ]:
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

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]:

Signaling Pathways >> Neuronal Signaling >> AChE
Signaling Pathways >> Neuronal Signaling >> Beta-secretase
Natural Products >> Alkaloid
Research Areas >> Metabolic Disease
Research Areas >> Neurological Disease

[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.


[Related Small Molecules]

MK-8931 | Galantamine | LY2886721 | AZD3293(Lanabecestat) | Choline glycerophosphate | benzethonium chloride | Malathion | LY2811376 | (-)-Huperzine A | pyridostigmine bromide | Scopoletin | Tacrine hydrochloride hydrate | Huperzine A | Epiberberine chloride | Protriptyline hydrochloride

Chemical & Physical Properties

[ Melting Point ]:
260ºC

[ Molecular Formula ]:
C20H18NO4+

[ Molecular Weight ]:
336.36

[ PSA ]:
40.80000

[ LogP ]:
-0.99

[ Storage condition ]:
2-8C

Related Compounds