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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
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
http://linked.open...aciTvurceVysledku
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  • 133875
http://linked.open...ai/riv/idVysledku
  • RIV/61989592:15310/12:33142149
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  • Mass spectrometry; Hydroxylation; Demethylenation; Oxidation; Berberine (en)
http://linked.open.../riv/klicoveSlovo
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
http://linked.open...ichTvurcuVysledku
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http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
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
issn
  • 1567-5394
number of pages
http://bibframe.org/vocab/doi
  • 10.1016/j.bioelechem.2011.09.002
http://localhost/t...ganizacniJednotka
  • 15310
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