Informační systém MU
GRYCOVÁ, Lenka, Jiří DOSTÁL a Radek MAREK. Quaternary protoberberine alkaloids. Phytochemistry. Oxford: Elsevier Science Ltd., 2007, roč. 68, č. 24, s. 150-175. ISSN 0031-9422. doi:10.1016/j.phytochem.2006.10.004.
Další formáty:   BibTeX LaTeX RIS
Základní 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
Originální jazyk angličtina
Typ výsledku Článek v odborném periodiku
Obor 10401 Organic chemistry
Stát vydavatele Velká Británie
Utajení není předmětem státního či obchodního tajemství
WWW DOI: 10.1016/j.phytochem.2006.10.004
Impakt faktor Impact factor: 2.322
Kód RIV RIV/00216224:14310/07:00020041
Organizační jednotka Přírodovědecká fakulta
Doi http://dx.doi.org/10.1016/j.phytochem.2006.10.004
UT WoS 000244013200001
Klíčová slova anglicky Berberidaceae; Quaternary protoberberine alkaloid; Plant source; Nucleophilic addition; NMR spectroscopy; X-ray diffraction; Cytotoxicity; DNA binding
Štítky Berberidaceae, cytotoxicity, DNA binding, NMR Spectroscopy, nucleophilic addition, Plant source, Quaternary protoberberine alkaloid, X-ray diffraction
Příznaky Mezinárodní význam, Recenzováno
Změnil Změnil: prof. RNDr. Radek Marek, Ph.D., učo 381. Změněno: 17. 6. 2013 14:53.
Anotace
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.
Anotace 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 VaVNázev: Rostlinné zdroje benzofenanthridinových alkaloidů a účinek těchto alkaloidů na normální a nádorové buňky
Investor: Grantová agentura ČR, Rostlinné zdroje benzofenanthridinových alkaloidů a účinek těchto alkaloidů na normální a nádorové buňky
LC06030, projekt VaVNázev: Biomolekulární centrum
Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Biomolekulární centrum
MSM0021622413, záměrNázev: Proteiny v metabolismu a při interakci organismů s prostředím
Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Proteiny v metabolismu a při interakci organismů s prostředím
Zobrazeno: 27. 11. 2022 11:03