Quaternary protoberberine alkaloids

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Year of publication 2007
Type Article in Periodical
Magazine / Source Phytochemistry
MU Faculty or unit

Faculty of Science

Web DOI: 10.1016/j.phytochem.2006.10.004
Doi http://dx.doi.org/10.1016/j.phytochem.2006.10.004
Field Organic chemistry
Keywords Berberidaceae; Quaternary protoberberine alkaloid; Plant source; Nucleophilic addition; NMR spectroscopy; X-ray diffraction; Cytotoxicity; DNA binding
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Description 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.
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