Article : Commentary on the chromatographic retention of Chelidonium alkaloids
Authors : Kowalska, T.Institute of Chemistry, Silesian University, 9 Szkolna Street, 40-006 Katowice, Poland, Kaczmarski, K.Chemical Engineering Department, Rzeszów University of Technology, Rzeszów, Poland, Pavlova, A.Analytical Department, Research and Development Institute, Lukoil-Neftochim-Bourgas-AD, 8104 Bourgas, Bulgaria, Giza, I.Plant Protection Institute, Sośnicowice Branch, ul. Gliwicka 29, 44-153 Sośnicowice, Poland, Walorczyk, S.Institute of Plant Protection, Department of Pesticide Residue Research, ul. Miczurina 20, 60-318 Poznań, Poland, Waksmundzka-Hajnos, M.Department of Inorganic and Analytical Chemistry, Medical University, Staszica 6, 20-081 Lublin, Poland, Gadzikowska, M.Department of Inorganic and Analytical Chemistry, Medical Academy, Staszica 6, 20-081 Lublin, Poland,
Abstract : Because basic isolates of Chelidonium majus L. constitute a valuable source of compounds with considerable medicinal potential, their chroma-tographic separation is a matter of continuous interest. Thus far, there has been no attempt to correlate the structural and retention properties of this biogenetically related but structurally diverse group of alkaloids. Taking as an example three representative sub-sets: chelidonine-type, protopine-type, and quaternary bases (berberine and benzo[c]phenanthridine-type) and analyzing their chromatographic behavior, we have concluded that polarity and lipophilicity descriptors derived from commonly used structural formulas are not sufficient for rationalization of their retention behavior. In particular, we draw attention to the exceptionally high polarity of protopine, which cannot be justified in terms of its polycyclic tertiary base structure bearing aminoketone functions in a medium size alicyclic ring, and would more appropriately be represented by a canonical formula indicative of the strong transannular interaction between the tertiary amine lone electron pair and the carbonyl carbon atom. As a consequence, the chromatographic mobility of protopine-type alkaloids might be categorized as that of quaternary rather than tertiary bases.
Publishing house : University of Silesia in Katowice
Publication date : 2001
Number : No. 11
Page : 62 – 74
Qute : Kowalska, T. ,Kaczmarski, K. ,Pavlova, A. ,Giza, I. ,Walorczyk, S. ,Waksmundzka-Hajnos, M. ,Gadzikowska, M. ,Gadzikowska, M. , Commentary on the chromatographic retention of Chelidonium alkaloids. Acta Chromatographica No. 11/2001