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

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	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 +1.2 V and +1.4 V (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). 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 +1.2 V and +1.4 V (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). (en)
Title	Electrochemical oxidation of berberine and mass spectrometric identification of its oxidation products Electrochemical oxidation of berberine and mass spectrometric identification of its oxidation products (en)
skos:prefLabel	Electrochemical oxidation of berberine and mass spectrometric identification of its oxidation products Electrochemical oxidation of berberine and mass spectrometric identification of its oxidation products (en)
skos:notation	RIV/61989592:15310/12:33142149!RIV13-MSM-15310___
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(ED2.1.00/03.0058), P(GPP503/11/P312), Z(MSM6198959216)
http://linked.open...iv/cisloPeriodika	SI
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Skopalová, Jana Papoušková, Barbora Maier, Vítězslav Ranc, Václav Jirovský, David
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Palackého v Olomouci / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	133875
http://linked.open...ai/riv/idVysledku	RIV/61989592:15310/12:33142149
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Mass spectrometry; Hydroxylation; Demethylenation; Oxidation; Berberine (en)
http://linked.open.../riv/klicoveSlovo	Mass spectrometry Berberine Demethylenation Hydroxylation Oxidation
http://linked.open...odStatuVydavatele	CH - Švýcarská konfederace
http://linked.open...ontrolniKodProRIV	[CA6184CBFDEC]
http://linked.open...i/riv/nazevZdroje	Bioelectrochemistry
http://linked.open...in/vavai/riv/obor	CG
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...vavai/riv/projekt	Regional Centre of Advanced Technologies and Materials Examination of safety of the alkaloids from Macleaya cordata by study their interactions with DNA using modern analytical tools
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	87
http://linked.open...iv/tvurceVysledku	Papoušková, Barbora Skopalová, Jana Maier, Vítězslav Ranc, Václav Vacek, Jan Jirovský, David
http://linked.open...ain/vavai/riv/wos	000309033000004
http://linked.open...n/vavai/riv/zamer	Modulation of signalling and regulatory pathways in normal and cancer cells
issn	1567-5394
number of pages	6 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.bioelechem.2011.09.002
http://localhost/t...ganizacniJednotka	15310

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