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Electrochemical oxidation of berberine and mass spectrometric identification of its oxidation products

J. Skopalová, J. Vacek, B. Papoušková, D. Jirovský, V. Maier, V. Ranc,

. 2012 ; 87 () : 15-20.

Jazyk angličtina Země Nizozemsko

Typ dokumentu časopisecké články, práce podpořená grantem

Perzistentní odkaz   https://www.medvik.cz/link/bmc13012768

Electrochemical oxidation of the isoquinoline alkaloid berberine in aqueous medium was studied by cyclic and differential pulse voltammetry at a glassy carbon electrode (GCE). Two anodic peaks of the quaternary form of berberine were observed at +1.2V and +1.4V (vs. SCE) in acidic and neutral solutions. When the anodic polarization exceeded the value of +1.1 V, the redox active film is formed on the GCE surface. The formation of adsorbed film was well-documented by quasireversible redox couple at +0.25 V which was studied in redox cycling experiments. In alkaline medium, a new anodic peak at +0.5 V appeared due to oxidation of berberine pseudobase to 8-oxoberberine. Solutions of berberine at different pH were subjected to controlled potential electrolysis on platinum gauze electrode and analyzed using liquid chromatography (HPLC) equipped with electrospray ionization/quadrupole time-of-flight mass spectrometry. The main water soluble monomeric product of berberine oxidation under physiological-near experimental conditions, OP1, was identified as demethyleneberberine cation (2,3-dihydroxy-9,10-dimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium).

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