2007
Quaternary protoberberine alkaloids
GRYCOVÁ, Lenka, Jiří DOSTÁL a Radek MAREKZákladní údaje
Originální název
Quaternary protoberberine alkaloids
Název česky
Kvartérní protoberberinové alkaloidy
Autoři
GRYCOVÁ, Lenka (203 Česká republika, domácí), Jiří DOSTÁL (203 Česká republika, domácí) a Radek MAREK (203 Česká republika, garant, domácí)
Vydání
Phytochemistry, Oxford, Elsevier Science Ltd. 2007, 0031-9422
Další údaje
Jazyk
angličtina
Typ výsledku
Článek v odborném periodiku
Obor
10401 Organic chemistry
Stát vydavatele
Velká Británie a Severní Irsko
Utajení
není předmětem státního či obchodního tajemství
Impakt faktor
Impact factor: 2.322
Kód RIV
RIV/00216224:14310/07:00020041
Organizační jednotka
Přírodovědecká fakulta
UT WoS
000244013200001
Klíčová slova anglicky
Berberidaceae; Quaternary protoberberine alkaloid; Plant source; Nucleophilic addition; NMR spectroscopy; X-ray diffraction; Cytotoxicity; DNA binding
Štítky
Příznaky
Mezinárodní význam, Recenzováno
Změněno: 17. 6. 2013 14:53, prof. RNDr. Radek Marek, Ph.D.
V originále
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.
Česky
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.
Návaznosti
| GA525/04/0017, projekt VaV |
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| LC06030, projekt VaV |
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| MSM0021622413, záměr |
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