Antimycobacterial and nitric oxide production inhibitory activities of limonoids isolated from Trichilia lepidota subsp. schumanniana (Harms) T.D.Penn.

Limonins / chemistry Nitric Oxide Meliaceae / chemistry Magnetic Resonance Spectroscopy Macrophages
Anti-inflammatory Antimycobacterial Meliaceae Trichilia lepidota subsp. schumanniana

Journal

Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434

Informations de publication

Date de publication:
Oct 2023
Historique:
received: 06 01 2023
revised: 01 08 2023
accepted: 04 08 2023
medline: 4 9 2023
pubmed: 10 8 2023
entrez: 9 8 2023
Statut: ppublish

Résumé

Six previously undescribed intact limonoids together with four known compounds were isolated from the seeds of Trichilia lepidota subsp. schumanniana (Harms) T.D.Penn. Their structures were characterized based on one- and two-dimensional nuclear magnetic resonance spectra, infrared, ultraviolet, mass spectroscopy results, and optical rotation. All compounds were evaluated for their ability to inhibit nitric oxide production in cultures of RAW 264.7 macrophages stimulated by lipopolysaccharide, cytotoxicity and growth of Mycobacterium tuberculosis strains H37Rv and M299. The compounds 7-deacetyl-11β,12α-diacetoxy-14,15-epoxyazadirone (5) and walsurin E (9) were the most potent in inhibiting nitric oxide production, although the compounds 1-deshydroxy-12α-acetoxymunronin N (1) and 6α,12α-dihydroxyazadirone (6) also showed controlled potential of this mediator, in addition to being potent growth inhibitors of Mycobacterium tuberculosis H37RV and M299, without cytotoxicity interference. Ring intact limonoids isolated from Trichilia lepidota subsp. schumanniana seeds are a new source of bioactive substances that may be used in the future against diseases such as tuberculosis and other processes related to inflammation.

Identifiants

DOI: 10.1016/j.phytochem.2023.113818 PMID: 37558193
pubmed: 37558193
pii: S0031-9422(23)00234-0
doi: 10.1016/j.phytochem.2023.113818
pii:
doi:

Substances chimiques

Limonins 0
Nitric Oxide 31C4KY9ESH

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

113818

Informations de copyright

Copyright © 2023 Elsevier Ltd. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Ivo J. Curcino Vieira reports financial support was provided by Carlos Chagas Filho Foundation for Research Support of Rio de Janeiro State. Ivo J. Curcino Vieira reports financial support was provided by National Council for Scientific and Technological Development. Raimundo Braz-Filho, Renata Rodrigues da Silva Robaina reports financial support was provided by Carlos Chagas Filho Foundation for Research Support of Rio de Janeiro State. Raimundo Braz-Filho reports financial support was provided by National Council for Scientific and Technological Development. Michel de Souza Passos, Thalya Soares Ribeiro Nogueira reports financial support was provided by Coordination of Higher Education Personnel Improvement.

Auteurs

Michel de Souza Passos (M)

Universidade Estadual do Norte Fluminense Darcy Ribeiro, Setor de Química dos Produtos Naturais, Laboratório de Ciências Químicas, Avenida Alberto Lamego 2000, CEP 28013-602, Campos dos Goytacazes, RJ, Brazil.

Thalya Soares Ribeiro Nogueira (TSR)

Universidade Estadual do Norte Fluminense Darcy Ribeiro, Setor de Química dos Produtos Naturais, Laboratório de Ciências Químicas, Avenida Alberto Lamego 2000, CEP 28013-602, Campos dos Goytacazes, RJ, Brazil.

Renata Rodrigues da Silva Robaina (RR)

Universidade Estadual do Norte Fluminense Darcy Ribeiro, Setor de Química dos Produtos Naturais, Laboratório de Ciências Químicas, Avenida Alberto Lamego 2000, CEP 28013-602, Campos dos Goytacazes, RJ, Brazil.

Sanderson Dias Calixto (SD)

Universidade Estadual do Norte Fluminense Darcy Ribeiro, Laboratório de Biologia do Reconhecer, Avenida Alberto Lamego 2000, CEP 28013-602, Campos dos Goytacazes, RJ, Brazil.

Thatiana Lopes Biá Ventura Simão (TLBV)

Universidade Estadual do Norte Fluminense Darcy Ribeiro, Laboratório de Biologia do Reconhecer, Avenida Alberto Lamego 2000, CEP 28013-602, Campos dos Goytacazes, RJ, Brazil.

Michelle Frazão Muzitano (MF)

Universidade Federal do Rio de Janeiro, Laboratório de Produtos Bioativos, CEP 27930-560, Macaé, RJ, Brazil.

Elena Lassounskaia (E)

Universidade Estadual do Norte Fluminense Darcy Ribeiro, Laboratório de Biologia do Reconhecer, Avenida Alberto Lamego 2000, CEP 28013-602, Campos dos Goytacazes, RJ, Brazil.

Raimundo Braz-Filho (R)

Universidade Estadual do Norte Fluminense Darcy Ribeiro, Setor de Química dos Produtos Naturais, Laboratório de Ciências Químicas, Avenida Alberto Lamego 2000, CEP 28013-602, Campos dos Goytacazes, RJ, Brazil; Departamento de Química, Instituto de Química, Universidade Federal Rural do Rio de Janeiro, CEP 20000-000, Seropédica, RJ, Brazil.

Ivo José Curcino Vieira (IJ)

Universidade Estadual do Norte Fluminense Darcy Ribeiro, Setor de Química dos Produtos Naturais, Laboratório de Ciências Químicas, Avenida Alberto Lamego 2000, CEP 28013-602, Campos dos Goytacazes, RJ, Brazil. Electronic address: curcino@uenf.br.

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Classifications MeSH

questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Terpènes › Triterpènes › Limonines › Antimycobacterial and nitric oxide production...
questionsmedicales.fr › Produits chimiques inorganiques › Composés de l'oxygène › Oxydes › Oxydes d'azote › Monoxyde d'azote › Antimycobacterial and nitric oxide production...
questionsmedicales.fr › Eucaryotes › Viridiplantae › Streptophyta › Embryophyta › Tracheobionta › Magnoliopsida › Meliaceae › Antimycobacterial and nitric oxide production...
questionsmedicales.fr › Techniques d'investigation › Techniques de chimie analytique › Analyse spectrale › Spectroscopie par résonance magnétique › Antimycobacterial and nitric oxide production...
questionsmedicales.fr › Systèmes sanguin et immunitaire › Système immunitaire › Phagocytes › Macrophages › Antimycobacterial and nitric oxide production...