Detailed Information on Publication Record
2007
Quaternary protoberberine alkaloids
GRYCOVÁ, Lenka, Jiří DOSTÁL and Radek MAREKBasic 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
Language
English
Type of outcome
Článek v odborném periodiku
Field of Study
10401 Organic chemistry
Country of publisher
United Kingdom of Great Britain and Northern Ireland
Confidentiality degree
není předmětem státního či obchodního tajemství
References:
Impact factor
Impact factor: 2.322
RIV identification code
RIV/00216224:14310/07:00020041
Organization unit
Faculty of Science
UT WoS
000244013200001
Keywords in English
Berberidaceae; Quaternary protoberberine alkaloid; Plant source; Nucleophilic addition; NMR spectroscopy; X-ray diffraction; Cytotoxicity; DNA binding
Tags
Tags
International impact, Reviewed
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.
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 project |
| ||
| LC06030, research and development project |
| ||
| MSM0021622413, plan (intention) |
|