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@article{1394832,
author = {Sándor, Roman and Slanina, Jiří and Midlik, Adam and Šebrlová, Kristýna and Novotná, Lucie and Čarnecká, Martina and Slaninová, Iva and Táborský, Petr and Táborská, Eva and Peš, Ondřej},
article_location = {Oxford},
article_number = {JAN 2018},
doi = {http://dx.doi.org/10.1016/j.phytochem.2017.10.010},
keywords = {Benzophenanthridine alkaloids; Ene adduct; Hydride transfer; LC-MS; NADH; NADH depletion; Redox cycling; Sanguinarine},
language = {eng},
issn = {0031-9422},
journal = {Phytochemistry},
title = {Sanguinarine is reduced by NADH through a covalent adduct},
volume = {145},
year = {2018}
}
TY - JOUR
ID - 1394832
AU - Sándor, Roman - Slanina, Jiří - Midlik, Adam - Šebrlová, Kristýna - Novotná, Lucie - Čarnecká, Martina - Slaninová, Iva - Táborský, Petr - Táborská, Eva - Peš, Ondřej
PY - 2018
TI - Sanguinarine is reduced by NADH through a covalent adduct
JF - Phytochemistry
VL - 145
IS - JAN 2018
SP - 77-84
EP - 77-84
PB - Pergamon-Elsevier Science LTD
SN - 00319422
KW - Benzophenanthridine alkaloids
KW - Ene adduct
KW - Hydride transfer
KW - LC-MS
KW - NADH
KW - NADH depletion
KW - Redox cycling
KW - Sanguinarine
N2 - Sanguinarine is a benzo[c]phenanthridine alkaloid with interesting cytotoxic properties, such as induction of oxidative DNA damage and very rapid apoptosis, which is not mediated by p53-dependent signaling. It has been previously documented that sanguinarine is reduced with NADH even in absence of any enzymes while being converted to its dihydro form. We found that the dark blue fluorescent species, observed during sanguinarine reduction with NADH and misinterpreted by Matkar et al. (Arch. Biochem. Biophys. 2008, 477, 43–52) as an anionic form of the alkaloid, is a covalent adduct formed by the interaction of NADH and sanguinarine. The covalent adduct is then converted slowly to the products, dihydrosanguinarine and NAD+, in the second step of reduction. The product of the reduction, dihydrosanguinarine, was continually re-oxidized by the atmospheric oxygen back to sanguinarine, resulting in further reacting with NADH and eventually depleting all NADH molecules. The ability of sanguinarine to diminish the pool of NADH and NADPH is further considered when explaining the sanguinarine-induced apoptosis in living cells.
ER -
SÁNDOR, Roman, Jiří SLANINA, Adam MIDLIK, Kristýna ŠEBRLOVÁ, Lucie NOVOTNÁ, Martina ČARNECKÁ, Iva SLANINOVÁ, Petr TÁBORSKÝ, Eva TÁBORSKÁ a Ondřej PEŠ. Sanguinarine is reduced by NADH through a covalent adduct. \textit{Phytochemistry}. Oxford: Pergamon-Elsevier Science LTD, 2018, roč.~145, JAN 2018, s.~77-84. ISSN~0031-9422. Dostupné z: https://dx.doi.org/10.1016/j.phytochem.2017.10.010.
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