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Molecules 2019, 24(6), 1026; https://doi.org/10.3390/molecules24061026

Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra

1
Instituto Federal de Santa Catarina, Câmpus Criciúma, Criciúma 88800-000, Santa Catarina, Brazil
2
Colegiado de Ciências Exatas e Biotecnológicas, Universidade Federal do Tocantins, Gurupi 77400-000, Tocantins, Brazil
3
Laboratório de Ciências Químicas, Centro de Ciência e Tecnologia, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes, Rio de Janeiro 20000-000, Brazil
4
Laboratório de Produtos Bioativos/LPBio, Curso de Farmácia, Universidade Federal do Rio de Janeiro, Campus Macaé, Macaé, Rio de Janeiro 20000-000, Brazil
5
Laboratório de Biologia do Reconhecer, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes, 28013-602, Rio de Janeiro 20000-000, Brazil
6
Departamento de Química, Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, Seropédica, Rio de Janeiro 20000-000, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Alessandra Guerrini
Received: 1 February 2019 / Revised: 20 February 2019 / Accepted: 5 March 2019 / Published: 15 March 2019
(This article belongs to the Special Issue Biological Activities of Plant Secondary Metabolites)
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Abstract

A phytochemical study of leaves and twigs of Psychotria nuda resulted in 19 compounds, including five indole alkaloids, N,N,N-trimethyltryptamine, lyaloside, strictosamide, strictosidine, and 5α-carboxystrictosidine; two flavonolignans, cinchonain Ia and cinchonain Ib; an iridoid, roseoside; a sugar, lawsofructose; a coumarin, scopoletin; a diterpene, phytol; three triterpenes, pomolic acid, spinosic acid, and rotungenic acid; and five steroids, sitosterol, stigmasterol, campesterol, β-sitosterol-3-O-β-d-glucoside, and β-stigmasterol-3-O-β-d-glucoside. Some compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis and their ability to inhibit NO production by macrophages stimulated by lipopolysaccharide (LPS). The compounds pomolic acid, spinosic acid, strictosidine, and 5α-carboxystrictosidine displayed antimycobacterial activity with minimum inhibitory concentrations ranging from 7.1 to 19.2 µg/mL. These compounds showed promising inhibitory activity against NO production (IC50 3.22 to 25.5 μg/mL). 5α-carboxystrictosidine did not show cytotoxicity against macrophages RAW264.7 up to a concentration of 100 µg/mL. With the exception of strictosamide, this is the first report of the occurrence of these substances in P. nuda. View Full-Text
Keywords: Rubiaceae; Psychotria nuda; alkaloids; Mycobacterium; inflammation; nitric oxide Rubiaceae; Psychotria nuda; alkaloids; Mycobacterium; inflammation; nitric oxide
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de Carvalho Junior, A.R.; Oliveira Ferreira, R.; de Souza Passos, M.; da Silva Boeno, S.I.; Glória das Virgens, L.L.; Ventura, T.L.B.; Calixto, S.D.; Lassounskaia, E.; de Carvalho, M.G.; Braz-Filho, R.; Curcino Vieira, I.J. Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra. Molecules 2019, 24, 1026.

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