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Statements

Subject Item
n2:RIV%2F61989592%3A15310%2F12%3A33142149%21RIV13-MSM-15310___
rdf:type
n8:Vysledek skos:Concept
dcterms: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).
dcterms: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
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
skos:notation
RIV/61989592:15310/12:33142149!RIV13-MSM-15310___
n8:predkladatel
n15:orjk%3A15310
n3:aktivita
n6:Z n6:P
n3:aktivity
P(ED2.1.00/03.0058), P(GPP503/11/P312), Z(MSM6198959216)
n3:cisloPeriodika
SI
n3:dodaniDat
n16:2013
n3:domaciTvurceVysledku
n11:6833446 n11:6670784 n11:3649768 n11:2670003 n11:2098628
n3:druhVysledku
n17:J
n3:duvernostUdaju
n19:S
n3:entitaPredkladatele
n4:predkladatel
n3:idSjednocenehoVysledku
133875
n3:idVysledku
RIV/61989592:15310/12:33142149
n3:jazykVysledku
n9:eng
n3:klicovaSlova
Mass spectrometry; Hydroxylation; Demethylenation; Oxidation; Berberine
n3:klicoveSlovo
n7:Hydroxylation n7:Berberine n7:Demethylenation n7:Mass%20spectrometry n7:Oxidation
n3:kodStatuVydavatele
CH - Švýcarská konfederace
n3:kontrolniKodProRIV
[CA6184CBFDEC]
n3:nazevZdroje
Bioelectrochemistry
n3:obor
n20:CG
n3:pocetDomacichTvurcuVysledku
5
n3:pocetTvurcuVysledku
6
n3:projekt
n12:GPP503%2F11%2FP312 n12:ED2.1.00%2F03.0058
n3:rokUplatneniVysledku
n16:2012
n3:svazekPeriodika
87
n3:tvurceVysledku
Jirovský, David Papoušková, Barbora Skopalová, Jana Maier, Vítězslav Vacek, Jan Ranc, Václav
n3:wos
000309033000004
n3:zamer
n10:MSM6198959216
s:issn
1567-5394
s:numberOfPages
6
n21:doi
10.1016/j.bioelechem.2011.09.002
n13:organizacniJednotka
15310