A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities

Autor: Daniel P. Bezerra, Guadalupe Edilma Licona de Macedo, Luciano de S. Santos, Antonio C. Doriguetto, Vanderlúcia Fonseca de Paula, Luiz C. A. Barbosa, Jeferson C. do Nascimento, Raphael Ferreira Queiroz, Milena Botelho Pereira Soares, Leia Alexandre Alves, Valdenizia R. Silva, Lauro José Caires Silva Júnior
Rok vydání: 2021
Předmět:
Zdroj: Phytochemistry Letters. 41:168-174
ISSN: 1874-3900
DOI: 10.1016/j.phytol.2020.11.019
Popis: A new tropane alkaloid 7β-acetoxy-6β-benzoyloxy-3α-hydroxytropane (1) was isolated from the twigs of Erythroxylum macrocalyx Mart. (Erythroxylaceae), along with the known substances: 6β,7β-dibenzoyloxy-3α-hydroxytropane (2), 6β,7β-dihydroxy-3α-(phenylacetoxy)tropane (3), 3α-benzoyloxy-6β,7β-dihydroxytropane (4), 6β-benzoyloxy-3α-(4-hydroxy-3,5-dimetoxybenzoyloxy)tropane (5), ombuin-3-rutinoside-5-glucoside (6), lupeol (7), taraxerol (8) and lupenone (9). Compounds 1 and 2 were also isolated from the leaves. The structures were established by analyses of 1D- and 2D-NMR and MS data, as well as by comparison with literature data for known compounds. The structure of 2 was also supported by X-ray crystallography analyses. The compounds were evaluated in vitro for their antibacterial and antiproliferative activities. Compound 5 showed high antiproliferative activity on liver hepatocellular carcinoma cells (HepG2) with IC50 value of 3.66 μg mL−1 (8.29 μmol L-1), but no cytotoxic effect (IC50 > 25 μg mL-1) on human lymphoblast cell line. This study reveals the potential use of 5 as prototype for the synthesis of new antiproliferative agents.
Databáze: OpenAIRE
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