Characterization of alkaloids in bark extracts of Geissospermum vellosii by HPLC-UV-diode array-multistage high-resolution mass spectrometry

A number of analytical studies, started in the sixties of the last century, concerning the stem bark of Geissospermum vellosii, have documented the presence of a number of indole alkaloids whose molecular identity was defined by NMR technique. The potential bioactivity of these compounds has inspired more recent analogous studies either devoted to structural elucidation of new alkaloid molecules or to the investigation of the role of some of them in cancer therapy. Anyway, a complete fingerprinting of the bark content is still lacking. In this paper, after a suitable extraction step, we obtain a chromatographic separation showing a number of components higher than the number of alkaloids so far described. Considering the great number of substances present in the stem bark, their identification is practically impossible to reveal by NMR techniques. As we presume that there are other stem bark unidentified alkaloids with important bioactivity, we propose to characterize their molecular structures by UV-Vis Diode Array spectrophotometry and High-Resolution Multistage Mass Spectrometry. The two adopted detection techniques were first tested on the already known Geissospermum vellosii molecules, and, after an inspection of their efficacy, were applied to the substances that have not yet been described. Herewith we propose the molecular structures of 10 substances that were never previously described, and in addition we provide experimental evidence of the presence of 6 already known substances which were never reported in the Geissospermum genus. A far more detailed description of the bark constituents is therefore provided.

Automated summary

This paper presents an analytical study on the stem bark of Geissospermum vellosii, focusing on the identification and characterization of indole alkaloids. The authors propose a new method using UV-Vis Diode Array spectrophotometry and High-Resolution Multistage Mass Spectrometry to identify the molecular structures of previously unknown alkaloids. They successfully describe the structures of 10 new substances and provide experimental evidence of the presence of 6 known substances not previously reported in the Geissospermum genus.