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Open Access Research article

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

Thais Guaratini12, Denise Brentan Silva12, Aline Cavalli Bizaro2, Lucas Rossi Sartori13, Hans-Ulrich Humpf3, Norberto Peporine Lopes1, Letícia Veras Costa-Lotufo4 and João Luis Callegari Lopes1*

Author Affiliations

1 Núcleo de Pesquisa em Produtos Naturais e Sintéticos (NPPNS), Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP), Universidade de São Paulo (USP), Av. Café s/nº, 14040-903 Ribeirão Preto, SP, Brazil

2 Lychnoflora Pesquisa e Desenvolvimento em Produtos Naturais LTDA, Rua Ângelo Mestriner 263, Ribeirão Preto, SP, Brazil, Ribeirão Preto, SP, Brazil

3 Institute of Food Chemistry, Westfälische Wilhelms-Universität Münster, Corrensstrasse 45, 48149 Münster, Germany

4 Departamento de Fisiologia e Farmacologia, Faculdade de Medicina, Universidade Federal do Ceará, 60430-270 Fortaleza, CE, Brazil

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BMC Complementary and Alternative Medicine 2014, 14:61  doi:10.1186/1472-6882-14-61

Published: 18 February 2014

Abstract

Background

Erythrina 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.

Methods

In 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).

Results

Erythraline 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.

Conclusions

The 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.

Keywords:
Spirocyclic alkaloids; Erythraline; in vitro metabolism; Erythrina verna; Fabaceae; Jacobsen catalyst; Erythrina alkaloids