One-Step Isolation of Monoterpene Indole Alkaloids from Psychotria leiocarpa Leaves and Their Antiviral Activity on Dengue Virus Type-2

• Autor(a) principal: Costa,Jéssica O.
• Data de Publicação: 2020
• Outros Autores: Barboza,Rodolfo S., Valente,Ligia M. M., Wolff,Thiago, Gomes,Mário, Gallo,Blanca, Berrueta,Luis A., Guimarães-Andrade,Iris P., Gavino-Leopoldino,Daniel, Assunção-Miranda,Iranaia
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020001002104
• topic: Psychotria leiocarpa; Rubiaceae; monoterpene indole alkaloids; phenolic compounds; solid-phase extraction; anti-dengue activity

The leaf MeOH extract of Psychotria leiocarpa (Rubiaceae) showed in vitro non-cytotoxic and anti-dengue virus serotype 2 (DENV2) activity in human hepatocarcinoma cell lineage (HepG2). A one-step and cost-effective reversed-phase solid-phase extraction method based on high-performance liquid chromatography (HPLC) parameters allowed the isolation, directly from this bioactive extract, of the monoterpene indole alkaloids: N-glucopyranosyl vincosamide (1), vincosamide (2) and strictosidinic acid (3). The chemical structures were characterized based on 1D and 2D nuclear magnetic resonance (NMR), UV and high-resolution mass spectra (HRMS). The methodology has also allowed yielding a polyphenolic-rich fraction that was analyzed by high-performance liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry (HPLC-DAD-ESI-MS/MS) revealing two flavonol triglycosides (4, 5) and three caffeoylquinic acid isomers (6-8). Compound 3 is reported for the first time in P. leiocarpa and all the phenolic compounds (4-8) are described for the first time in the genus Psychotria. Compounds 1-3 showed to be non-cytotoxic and anti-dengue active towards DENV2, highlighting vincosamide (2).