Alcaloides indólicos de Aspidosperma pyrifolium: estudo fitoquímico e dados espectroscópicos

Abstract

Aspidosperma pyrifolium Mart., a native species of the caatinga with great occurrence in the northeast, known perpularmente as pereiro, used in popular medicine in the treatment of diseases and diseases. There are several studies carried out in the literature, reporting the presence of classes of organic compounds such as alkaloids, among others, that would be responsible for the therapeutic properties of this species. The phytochemical study of A. pyrifolium, seed fractions and fruit peels using classical chromatographic methods and purification by HPLC allowed us to isolate three compounds. From the hexanic fraction of fruit peels (APCF-H) was isolated the betulinic acid triterpene, not previously reported in the A. pyrifolium species. From the dichloromethane (APSE/DCM) and ethyl acetate 50% dichloromethane (APSEA / 50% DCM) fractions of the seeds, it was possible to isolate the pentacyclic pentameric aspidospermine alkaloid from the glycosylated β-carboline alkaloid Cordifolina, not previously described in the species and another compound of the β-carboline type that does not have a structure elucidated until the moment. The extract of the seeds dichloromethane fraction (APSE/DCM) was analyzed by GC/MS (gas chromatography coupled to mass spectrometry) and its data were compared with data in the literature in database (NIST08.LIB), the presence of the alkaloids 1-acetyl-aspidospermidine, aspidospermine and pyrifoline, among other minor compounds. The antioxidant activity evaluation of the APSE/DCM fraction showed a percentage of maximum antioxidant activity (AA% maximum) of 83.68%, with the free radical sequestration method of DPPH (2,2-diphenyl-1-picryl-hydrazila). Inhibitory concentration 50% (IC50) 133.4867 ± 2.22. The fraction of the seeds dichloromethane fraction (APSE/DCM) was evaluated in relation to the toxicity against Artemia salina, considering that there were already reports of the toxicity in the leaves of A. pyrifolium, we verified the acute toxicity in the seed dichloromethane fraction with average lethal concentration (CL50) in 24 hours of 1.1524 μg.ml-1, species with CL50 less than 1000 μg.ml-1 being considered toxic. In the second part of the work a bibliographic survey of naturally occurring β-carboline alkaloids with their structures, reported activities and a database with their chemical displacements in 1H and 13C NMR were carried out, totaling 169 alkaloids described in the literature. From 1992 to 2016, grouped into four main groups, named β-carboline, dihydro-β-carboline, tetrahydro-β-carboline and the divergent β-carbolines, this survey will aid in the structural elucidation of new molecules.