633-65-8/Berberine

Chemical Properties

yellow crystalline powder

Uses

antiarrhythmic, alpha2 agonist, anticonvulsant, antiinflammatory, antibacterial, antifungal, antitrypanosomal, antineoplastic, immunostimulant

General Description

A highly potent and selective oxysterol EBI2 (GPR183) agonist (Kd) = 450 pM in a saturation binding assay, and EC50 = 140 pM over EC50 = 2.1 nM for its enantiomer, 7β,25-OHC, in a GTP-γS binding assay). Dose-dependently suppresses forskolin-induced cAMP accumulation in an EBI2-expressing SK-N-MC/CRE-β-galactosidase cell line (IC50 = 2 nM), but not in control cells. Stimulates migration of LPS-activated spleen B-cells and anti-CD3/CD28-activated CD4+ T-cells in a dose-dependent manner. In addition, pharmacological inhibition of its biosynthesis in vivo by Clotrimazole, a CYP7B1inhibitor, promotes the migration of adoptively transferred pre-activated B cells to the T/B boundary, mimicking the phenotype of pre-activated B cells in EBI2-deficient mice.

Biochem/physiol Actions

An alkaloid with weak antibiotic properties. Substrate for MDR efflux pumps. Antimicrobial activities of berberine is potentiated by the MDR inhibitor 5′-methoxyhydnocarpin (5′-MHC). Berberine upregulates the expression of Pgp in hepatoma cells. Treatment with berberine potentially results in the reduced accumulation of chemotherapeutic drugs.

Safety Profile

Poison by intraperitoneal route.Slightly toxic by ingestion. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx andCl-.

Purification Methods

Berberine chloride crystallises from water to give the dihydrate. The anhydrous salt may be obtained by recrystallisation from EtOH/Et2O, wash the crystals with Et2O and dry them in a vacuum. The iodide has m 250o(dec) (from EtOH). [Perkin J Chem Soc 113 503 1918, Kametani et al. J Chem Soc(C) 2036 1969, Beilstein 27 I 515, 27 II 567.]