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Aporphine Alkaloids from Ocotea puberula with Anti‐ Trypanosoma Cruzi Potential – Activity of Dicentrine‐β‐ N ‐Oxide in the Plasma Membrane Electric Potentials
Author(s) -
Barbosa Henrique,
CostaSilva Thais A.,
Alves Conserva Geanne A.,
Araujo Adelson J.,
Lordello Ana Luísa L.,
Antar Guilherme M.,
Amaral Maiara,
Soares Marisi G.,
Tempone Andre G.,
Lago João Henrique G.
Publication year - 2021
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202001022
Subject(s) - benznidazole , alkaloid , aporphine , trypanosoma cruzi , chemistry , lauraceae , depolarization , stereochemistry , biophysics , biology , botany , parasite hosting , world wide web , computer science
One new aporphine, dicentrine‐β‐ N ‐oxide ( 1 ), together with five related known alkaloids dehydrodicentrine ( 2 ), predicentrine ( 3 ), N ‐methyllaurotetanine ( 4 ), cassythicine ( 5 ), and dicentrine ( 6 ) were isolated from the leaves of Ocotea puberula (Lauraceae). Antiprotozoal activity of the isolated compounds was evaluated in vitro against trypomastigote forms of Trypanosoma cruzi . Among the tested compounds, alkaloid 1 exhibited higher potential with EC 50 value of 18.2 μM and reduced toxicity against NCTC cells (CC 50 >200 μM – SI>11.0), similar to positive control benznidazole (EC 50 of 17.7 μM and SI=10.7). Considering the promising results of dicentrine‐β‐ N ‐oxide ( 1 ) against trypomastigotes, the mechanism of parasite death caused by this alkaloid was investigated. As observed, this compound reached the plasma membrane electric potential directly after 2 h of incubation and triggered mitochondrial depolarization, which probably leads to trypomastigote death. Therefore, dicentrine‐β‐ N ‐oxide ( 1 ), reported for the first time in this work, can contribute to future works for the development of new trypanocidal agents.