GRYCOVÁ, Lenka, Jiří DOSTÁL and Radek MAREK. Quaternary protoberberine alkaloids. Phytochemistry. Oxford: Elsevier Science Ltd., 2007, vol. 68, No 24, p. 150-175. ISSN 0031-9422. doi:10.1016/j.phytochem.2006.10.004.
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Basic information
Original name Quaternary protoberberine alkaloids
Name in Czech Kvartérní protoberberinové alkaloidy
Authors GRYCOVÁ, Lenka (203 Czech Republic, belonging to the institution), Jiří DOSTÁL (203 Czech Republic, belonging to the institution) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution).
Edition Phytochemistry, Oxford, Elsevier Science Ltd. 2007, 0031-9422.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10401 Organic chemistry
Country of publisher United Kingdom of Great Britain and Northern Ireland
Confidentiality degree is not subject to a state or trade secret
WWW DOI: 10.1016/j.phytochem.2006.10.004
Impact factor Impact factor: 2.322
RIV identification code RIV/00216224:14310/07:00020041
Organization unit Faculty of Science
Doi http://dx.doi.org/10.1016/j.phytochem.2006.10.004
UT WoS 000244013200001
Keywords in English Berberidaceae; Quaternary protoberberine alkaloid; Plant source; Nucleophilic addition; NMR spectroscopy; X-ray diffraction; Cytotoxicity; DNA binding
Tags Berberidaceae, cytotoxicity, DNA binding, NMR Spectroscopy, nucleophilic addition, Plant source, Quaternary protoberberine alkaloid, X-ray diffraction
Tags International impact, Reviewed
Changed by Changed by: prof. RNDr. Radek Marek, Ph.D., učo 381. Changed: 17. 6. 2013 14:53.
Abstract
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.
Abstract (in Czech)
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.
Links
GA525/04/0017, research and development projectName: Rostlinné zdroje benzofenanthridinových alkaloidů a účinek těchto alkaloidů na normální a nádorové buňky
Investor: Czech Science Foundation, Plant sources of benzophenanthridine alkaloids and effects of these alkaloid on normal and cancer cells
LC06030, research and development projectName: Biomolekulární centrum
Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular centre
MSM0021622413, plan (intention)Name: Proteiny v metabolismu a při interakci organismů s prostředím
Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment
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