Abstract
The separation of nine heteroyohimbine and eight oxindole alkaloids has been investigated by using reversed-phase high-performance liquid chromatography. The behaviour of these seventeen alkaloids has been compared with the separations obtained on silica gel thin-layer chromatography plates. Whereas the sequence of separation on adsorbent layers can be rationalised, at a molecular level, by assessing the ability of nitrogen lone-pair electrons to hydrogen bond with silanol hydroxyl groups, no clear pattern emerges from the results of the reversed-phase high-performance liquid chromatographic separations. Although some alkaloids exhibit the expected reversed-phase behaviour, other alkaloids follow the same sequence of elution as found on adsorption systems.
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