Abstract
The methanolic extract of Tabernaemontana catharinensis (Apocynaceae) roots, which contains alkaloids with several biological activities, was separated on a preparative scale using high-speed counter-current chromatography. The optimum solvent system was found to be a mixture of CHCl3-MeOH-H2O [5:10:6 (v/v/v)] and led to a successful separation of two monoterpenic indole alkaloids, voachalotine (1) and 12-methoxy-Nb-methylvoachalotine (2) in approximately 4.0 hours. The alkaloids were all isolated at purities over 95%, and their structures were established on the basis of spectroscopic methods, including 1D and 2D NMR and EI/MS.
Highlights
The genus Tabernaemontana includes about 110 species widespread in the pantropical regions, and these species are rich in alkaloids [1,2,3,4], mostly of the monoterpenic indole type, revealing a considerable variety of carbon skeletons and novel biological activities [5].Tabernaemontana catharinensis A
The main purpose of this contribution was to study the purification on a preparative scale of the two main monoterpenic indole alkaloids, voachalotine (1) and 12-methoxy-Nbmethylvoachalotine (2), from T. catharinensis by high-speed countercurrent chromatography (HSCCC)
The suitable solvent system for HSCCC separation was developed according this rule considering the properties of the target compounds
Summary
The genus Tabernaemontana includes about 110 species widespread in the pantropical regions, and these species are rich in alkaloids [1,2,3,4], mostly of the monoterpenic indole type, revealing a considerable variety of carbon skeletons and novel biological activities [5]. We investigate mainly polar extracts containing alkaloids compounds, which can be degraded because of the acidic nature of the silica gel To overcome this problem, the use of high-speed countercurrent chromatography (HSCCC) that does not employ a solid-phase support and there is no irreversible adsorption associated with the solid supports, can be an alternative to the direct application of crude extracts and provide excellent recovery of the compounds [13]. The use of high-speed countercurrent chromatography (HSCCC) that does not employ a solid-phase support and there is no irreversible adsorption associated with the solid supports, can be an alternative to the direct application of crude extracts and provide excellent recovery of the compounds [13] This method has been successfully applied to the analysis and separation of various natural products [14,15]. The main purpose of this contribution was to study the purification on a preparative scale of the two main monoterpenic indole alkaloids, voachalotine (1) and 12-methoxy-Nbmethylvoachalotine (2), from T. catharinensis by HSCCC
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