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@article{700800,
author = {Grycová, Lenka and Dostál, Jiří and Marek, Radek},
article_location = {Oxford},
article_number = {24},
doi = {http://dx.doi.org/10.1016/j.phytochem.2006.10.004},
keywords = {Berberidaceae; Quaternary protoberberine alkaloid; Plant source; Nucleophilic addition; NMR spectroscopy; X-ray diffraction; Cytotoxicity; DNA binding},
language = {eng},
issn = {0031-9422},
journal = {Phytochemistry},
title = {Quaternary protoberberine alkaloids},
url = {http://dx.doi.org/10.1016/j.phytochem.2006.10.004},
volume = {68},
year = {2007}
}
TY - JOUR
ID - 700800
AU - Grycová, Lenka - Dostál, Jiří - Marek, Radek
PY - 2007
TI - Quaternary protoberberine alkaloids
JF - Phytochemistry
VL - 68
IS - 24
SP - 150
EP - 150
PB - Elsevier Science Ltd.
SN - 00319422
KW - Berberidaceae
KW - Quaternary protoberberine alkaloid
KW - Plant source
KW - Nucleophilic addition
KW - NMR spectroscopy
KW - X-ray diffraction
KW - Cytotoxicity
KW - DNA binding
UR - http://dx.doi.org/10.1016/j.phytochem.2006.10.004
L2 - http://dx.doi.org/10.1016/j.phytochem.2006.10.004
N2 - This contribution reviews some general aspects of the quaternary iminium protoberberine alkaloids. The alkaloids represent a very extensive group of secondary metabolites with diverse structures, distribution in nature, and biological effects. The quaternary protoberberine alkaloids (QPA), derived from the 5,6-dihydrodibenzo[a,g]quinolizinium system, belong to a large class of isoquinoline alkaloids. Following a general introduction, the plant sources of QPA, their biosynthesis, and procedures for their isolation are discussed. Analytical methods and spectral data are summarized with emphasis on NMR spectroscopy. The reactivity of QPA is characterized by the sensitivity of the iminium bond C=N+ to nucleophilic attack. The addition of various nucleophiles to the protoberberine skeleton is discussed. An extended discussion of the principal chemical reactivity is included since this governs interactions with biological targets. Quaternary protoberberine alkaloids and some related compounds exhibit considerable biological activities. Recently reported structural studies indicate that the QPA interact with nucleic acids predominantly as intercalators or minor groove binders. Currently, investigations in many laboratories worldwide are focused on the antibacterial and antimalarial activity, cytotoxicity, and potential genotoxicity of QPA.
ER -
GRYCOVÁ, Lenka, Jiří DOSTÁL a Radek MAREK. Quaternary protoberberine alkaloids. \textit{Phytochemistry}. Oxford: Elsevier Science Ltd., 2007, roč.~68, č.~24, s.~150-175. ISSN~0031-9422. Dostupné z: https://dx.doi.org/10.1016/j.phytochem.2006.10.004.
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