Chemical composition, antimycobacterial and anti-inflammatory activities of iridoids and triterpene from Psychotria suterella (Rubiaceae)

Almir Ribeiro De Carvalho Junior; Rafaela Oliveira Ferreira; Michel de Souza Passos; Milena Gonçalves Curcino Vieira; Lorena de Lima Glória das Virgens; Sanderson Dias Calixto; Thatiana Lopes Biá Ventura; Elena Lassounskaia; Mario Geraldo de Carvalho; Raimundo Braz-Filho; Ivo José Curcino Vieira

Articles

Abstract

Pharmacognosy Magazine,2021,17,74,355-359.

DOI:10.4103/pm.pm_93_20

Published:July 2021

Type:Original Article

Authors:

Author(s) affiliations:

Almir Ribeiro De Carvalho Junior¹, Rafaela Oliveira Ferreira², Michel de Souza Passos³, Milena Gonçalves Curcino Vieira⁴, Lorena de Lima Glória das Virgens⁵, Sanderson Dias Calixto⁵, Thatiana Lopes Biá Ventura⁶, Elena Lassounskaia⁵, Mario Geraldo de Carvalho⁷, Raimundo Braz-Filho⁸, Ivo José Curcino Vieira³
¹ Instituto Federal de Santa Catarina, Câmpus Criciúma, Criciúma, SC, Brazil
² Centro de Ciências Exatas e Tecnológicas, Universidade Federal do Recôncavo da Bahia, Cruz das Almas, BA, Brazil
³ Laboratório de Ciências Químicas, Centro de Ciência e Tecnologia, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes, Macaé, Brazil
⁴ Instituto Federal Fluminense, Câmpus Centro, Campos dos Goytacazes, Macaé, Brazil
⁵ Laboratório de Biologia do Reconhecer, Centro de Biociências e Biotecnologia, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes, Macaé, Brazil
⁶ Laboratório de Produtos Bioativos, Curso de Farmácia, Universidade Federal do Rio de Janeiro, Macaé, Brazil
⁷ Departamento de Química, Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, Seropédica, RJ, Brazil
⁸ Laboratório de Ciências Químicas, Centro de Ciência e Tecnologia, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes, Macaé; Departamento de Química, Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, Seropédica, RJ, Brazil

Abstract:

Background: Psychotria species are known for their medicinal properties and psychoactive activities. Extracts of Psychotria suterella showed anti-tuberculosis (TB) activity; however, the substances related to this activity are unknown. Objectives: The objective was to study on the chemical constituents of the leaves of plant and evaluate the anti-TB and anti-inflammatory activity. Materials and Methods: Solvent extraction, partition, and column chromatography were used to separate the compounds. The structures of these compounds were determined by extensive one dimensional-and two dimensional-Nuclear Magnetic Resonance, infrared and mass spectrometry spectroscopic analyses. Some compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis and their ability to inhibit nitric oxide (NO) production by lipopolysaccharide-stimulated macrophages. Results: This study led to the isolation and characterization of a new iridoid, named epi-geniposidic acid (1), together with nine known compounds: geniposidic acid (2), 3-O-acethyloleanolic acid (3), pomolic acid (4), spinolic acid (5), maslinic acid (6), tormentic acid (7), methyl oleanolate (8), lyalosidic acid (9), and strictosidinic acid (10). Triterpene 3-O-acethyloleanolic acid (3) was found to display antimycobacterial activity against M. tuberculosis H37Rv strain and hypervirulent strain (minimum inhibitory concentration 6.7 ± 0.1 and 89.1 ± 1.3 μg/mL, respectively). Epi-geniposidic acid (1), geniposidic acid (2), and 3-O-acethyloleanolic acid (3) showed promising inhibitory activities against NO production (IC₅₀ range 4.12–5.12 μg/mL). The iridoid mixture showed no cytotoxicity against RAW 264.7 macrophages up to a concentration of 100 μg/mL. Conclusion: P. suterella presents relevant biological properties and should be considered for further in vivo studies using a pulmonary TB model.