Quaternary protoberberine alkaloids

• Published in: Phytochemistry (Oxford) 2007, Vol.68 (2), p.150-175
• Main Authors: Grycová, Lenka, Dostál, Jiří, Marek, Radek
• Format: Article
• Language: English
• Subjects: Berberidaceae; Berberine Alkaloids - chemistry; Berberine Alkaloids - isolation & purification; Berberine Alkaloids - metabolism; Berberine Alkaloids - pharmacology; Biological and medical sciences; Chemical constitution; Cytotoxicity; DNA binding; Fundamental and applied biological sciences. Psychology; General pharmacology; Medical sciences; NMR spectroscopy; Nucleophilic addition; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant physiology and development; Plant source; Plants - chemistry; Quaternary protoberberine alkaloid; X-ray diffraction
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2006.10.004

This contribution reviews some general aspects of the quaternary iminium protoberberine alkaloids, including their plant sources, isolation procedures, analytical methods, spectral data, and reactivity. Examples of pharmacological effects and interactions with biological targets are described. 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.