| Quaternary protoberberine alkaloids. | |
| | |
MedLine Citation:
|
PMID: 17109902 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
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 CN(+) 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. |
| | |
Authors:
|
Lenka Grycová; Jirí Dostál; Radek Marek |
Publication Detail:
|
Type: Journal Article; Research Support, Non-U.S. Gov't; Review Date: 2006-11-15 |
Journal Detail:
|
Title: Phytochemistry Volume: 68 ISSN: 0031-9422 ISO Abbreviation: Phytochemistry Publication Date: 2007 Jan |
Date Detail:
|
Created Date: 2007-01-08 Completed Date: 2007-04-03 Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 0151434 Medline TA: Phytochemistry Country: United States |
Other Details:
|
Languages: eng Pagination: 150-75 Citation Subset: IM |
Affiliation:
|
National Center for Biomolecular Research, Faculty of Science, Masaryk University, Kamenice 5/A4, CZ-625 00 Brno, Czech Republic. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Berberine Alkaloids
/
chemistry*,
isolation & purification,
metabolism,
pharmacology* Plants / chemistry |
| Chemical | |
Reg. No./Substance:
|
0/Berberine Alkaloids; 19716-69-9/protoberberine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Refuge use: a conflict between avoiding predation and losing mass in lizards.
Next Document: Arbuscular mycorrhizal symbiosis and plant aquaporin expression.