In vitro metabolism studies of erythraline, the major spiroalkaloid from Erythrina verna

Abstract

BackgroundErythrina verna, popularly known as “mulungu”, is a Brazilian medicinal plant used to treat anxiety. Erythrina alkaloids have been described in several species of Erythrina, which have biological and therapeutic properties well known that include anxiolytic and sedative effects.MethodsIn this work, in vitro metabolism of erythraline (1), the major spirocyclic alkaloid of Erythrina verna, was studied in the pig cecum model and by biomimetic phase I reactions. The biomimetic reactions were performed with Jacobsen catalyst to produce oxidative metabolites and one metabolite was isolated and evaluated against cancer cells, as HL-60 (promyelocytic leukemia), SF-295 (Glioblastoma) and OVCAR-8 (ovarian carcinoma).ResultsErythraline exhibited no metabolization by the pig microbiota and a main putative metabolite was formed in a biomimetic model using Jacobsen catalyst. This metabolite was isolated and identified as 8-oxo-erythraline (2). Finally, erythraline and the putative metabolite were tested in MTT model and both compounds showed no important cytotoxic activity against tumor cells.ConclusionsThe alkaloid erythraline was not metabolized by intestinal microbiota, but it was possible to identify its oxidative metabolite from biomimetic reactions. So these data are interesting and stimulate other studies involving this alkaloid, since it is present in phytomedicine products and there are not reported data about the metabolism of erythrina alkaloids.

Gas‐phase dissociation study of erythrinian alkaloids by electrospray ionization mass spectrometry and computational methods

“…Our research group has defined the structure of a putative erythraline metabolite (Fig. , 2b ) in biomimetic procedures; we have also suggested a possible phase I metabolite . In vitro assays have shown that these two compounds do not exert any cytotoxic effects.…”

“…1, 2b) in biomimetic procedures; we have also suggested a possible phase I metabolite. [13] In vitro assays have shown that these two compounds do not exert any cytotoxic effects. Erythraline (Fig.…”

The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C14H19N2O2Cl

“…The genus Erythrina Mart. (Leguminoseae-Fabaceae) comprises around 115-118 known species [5][6][7] that grow in tropicalsubtropical regions and in some temperate regions of the world in different ecosystems [7][8][9]. This alkaloid was first isolated from seeds of Erythrina hypaphorus Boerl [10].…”

The genus Erythrina L.: A review on its alkaloids, preclinical, and clinical studies

“…The alkaloid erythraline ( 40 ), from E. verna barks, had its metabolism evaluated using a biomimetic phase I reaction. The metabolic product was identified as 8‐oxo‐erythraline (Guaratini et al, ). Additionally, the CYP450‐mediated metabolism of erythraline ( 40 ) was assayed using rat and human liver microsomes to predict the in vivo metabolism, affording also 8‐oxo‐erythraline ( 37 ; Marques et al, ).…”