Epiberberine chloride

Epiberberine chloride 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 chloride has antioxidant activity, with peroxynitrite ONOO- scavenging effect (IC50, 16.83 μM), and may protect against Alzheimer disease. Epiberberine chloride inhibits the early stage of differentiation of 3T3-L1 preadipocytes, downregulates the Raf/MEK1/2/ERK1/2 and AMPKα/Akt pathways. Epiberberine has the potential effect in the research of diabetic disease.

Product information

CAS Number: 889665-86-5

Molecular Weight: 371.81

Formula: C20H18ClNO4

Chemical Name: 16,17-dimethoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-1-ylium chloride

Smiles: [Cl-].COC1C=C2CC[N+]3C=C4C5OCOC=5C=CC4=CC=3C2=CC=1OC

InChiKey: DGRBIBRPLDAHJH-UHFFFAOYSA-M

InChi: InChI=1S/C20H18NO4.ClH/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;/p-1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 25 mg/mL (67.24 mM; Need ultrasonic).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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. Epiberberine (12.5-50 μM) suppresses the Raf/MEK1/ERK1/2 and AMPKα/Akt pathways in the early stage of 3T3-L1 adipocyte differentiation. Epiberberine (0.2, 1, 5 μg/mL) inhibits glucose uptake in HepG2 cells in a concentration-dependent manner.

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.

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.

Products are for research use only. Not for human use.