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

Journal of the Brazilian Chemical Society

article

Costa, Jéssica O.¹  Assunção-Miranda, Iranaia²  Barboza, Rodolfo S.¹  Valente, Ligia M. M.¹  Wolff, Thiago¹  Gomes, Mário¹  Gallo, Blanca³  Berrueta, Luis A.³  Guimarães-Andrade, Iris P.²  Gavino-Leopoldino, Daniel² 

[1] Instituto de Química, Universidade Federal do Rio de Janeiro;Instituto de Microbiologia Paulo Góes, Universidade Federal do Rio de Janeiro;Departamento de Química Analítica, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU)

关键词: Psychotria leiocarpa;    Rubiaceae;    monoterpene indole alkaloids;    phenolic compounds;    solid-phase extraction;    anti-dengue activity;   

DOI  :  10.21577/0103-5053.20200111

学科分类：内科医学

来源: SciELO

【 摘 要 】

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 ).

【 授权许可】

CC BY