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Chemical profile of Lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations

The essential oils of the fresh and dry flowers, leaves, branches, and roots of Lippia thymoides were obtained by hydrodistillation and analyzed using gas chromatography (GC) and GC–mass spectrometry (MS). The acetylcholinesterase inhibitory activity of the essential oil of fresh leaves was investig...

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Autores principales: Silva, Sebastião Gomes, da Costa, Renato Araújo, de Oliveira, Mozaniel Santana, da Cruz, Jorddy Neves, Figueiredo, Pablo Luis B., Brasil, Davi do Socorro Barros, Nascimento, Lidiane Diniz, Chaves Neto, Antônio Maia de Jesus, de Carvalho Junior, Raul Nunes, Andrade, Eloisa Helena de Aguiar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6407782/
https://www.ncbi.nlm.nih.gov/pubmed/30849129
http://dx.doi.org/10.1371/journal.pone.0213393
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author Silva, Sebastião Gomes
da Costa, Renato Araújo
de Oliveira, Mozaniel Santana
da Cruz, Jorddy Neves
Figueiredo, Pablo Luis B.
Brasil, Davi do Socorro Barros
Nascimento, Lidiane Diniz
Chaves Neto, Antônio Maia de Jesus
de Carvalho Junior, Raul Nunes
Andrade, Eloisa Helena de Aguiar
author_facet Silva, Sebastião Gomes
da Costa, Renato Araújo
de Oliveira, Mozaniel Santana
da Cruz, Jorddy Neves
Figueiredo, Pablo Luis B.
Brasil, Davi do Socorro Barros
Nascimento, Lidiane Diniz
Chaves Neto, Antônio Maia de Jesus
de Carvalho Junior, Raul Nunes
Andrade, Eloisa Helena de Aguiar
author_sort Silva, Sebastião Gomes
collection PubMed
description The essential oils of the fresh and dry flowers, leaves, branches, and roots of Lippia thymoides were obtained by hydrodistillation and analyzed using gas chromatography (GC) and GC–mass spectrometry (MS). The acetylcholinesterase inhibitory activity of the essential oil of fresh leaves was investigated on silica gel plates. The interactions of the key compounds with acetylcholinesterase were simulated by molecular docking and molecular dynamics studies. In total, 75 compounds were identified, and oxygenated monoterpenes were the dominant components of all the plant parts, ranging from 19.48% to 84.99%. In the roots, the main compounds were saturated and unsaturated fatty acids, having contents varying from 39.5% to 32.17%, respectively. In the evaluation of the anticholinesterase activity, the essential oils (detection limit (DL) = 0.1 ng/spot) were found to be about ten times less active than that of physostigmine (DL = 0.01ng/spot), whereas thymol and thymol acetate presented DL values each of 0.01 ng/spot, equivalent to that of the positive control. Based on the docking and molecular dynamics studies, thymol and thymol acetate interact with the catalytic residues Ser203 and His447 of the active site of acetylcholinesterase. The binding free energies (ΔG(bind)) for these ligands were -18.49 and -26.88 kcal/mol, demonstrating that the ligands are able to interact with the protein and inhibit their catalytic activity.
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spelling pubmed-64077822019-03-17 Chemical profile of Lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations Silva, Sebastião Gomes da Costa, Renato Araújo de Oliveira, Mozaniel Santana da Cruz, Jorddy Neves Figueiredo, Pablo Luis B. Brasil, Davi do Socorro Barros Nascimento, Lidiane Diniz Chaves Neto, Antônio Maia de Jesus de Carvalho Junior, Raul Nunes Andrade, Eloisa Helena de Aguiar PLoS One Research Article The essential oils of the fresh and dry flowers, leaves, branches, and roots of Lippia thymoides were obtained by hydrodistillation and analyzed using gas chromatography (GC) and GC–mass spectrometry (MS). The acetylcholinesterase inhibitory activity of the essential oil of fresh leaves was investigated on silica gel plates. The interactions of the key compounds with acetylcholinesterase were simulated by molecular docking and molecular dynamics studies. In total, 75 compounds were identified, and oxygenated monoterpenes were the dominant components of all the plant parts, ranging from 19.48% to 84.99%. In the roots, the main compounds were saturated and unsaturated fatty acids, having contents varying from 39.5% to 32.17%, respectively. In the evaluation of the anticholinesterase activity, the essential oils (detection limit (DL) = 0.1 ng/spot) were found to be about ten times less active than that of physostigmine (DL = 0.01ng/spot), whereas thymol and thymol acetate presented DL values each of 0.01 ng/spot, equivalent to that of the positive control. Based on the docking and molecular dynamics studies, thymol and thymol acetate interact with the catalytic residues Ser203 and His447 of the active site of acetylcholinesterase. The binding free energies (ΔG(bind)) for these ligands were -18.49 and -26.88 kcal/mol, demonstrating that the ligands are able to interact with the protein and inhibit their catalytic activity. Public Library of Science 2019-03-08 /pmc/articles/PMC6407782/ /pubmed/30849129 http://dx.doi.org/10.1371/journal.pone.0213393 Text en © 2019 Silva et al http://creativecommons.org/licenses/by/4.0/ This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) , which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
spellingShingle Research Article
Silva, Sebastião Gomes
da Costa, Renato Araújo
de Oliveira, Mozaniel Santana
da Cruz, Jorddy Neves
Figueiredo, Pablo Luis B.
Brasil, Davi do Socorro Barros
Nascimento, Lidiane Diniz
Chaves Neto, Antônio Maia de Jesus
de Carvalho Junior, Raul Nunes
Andrade, Eloisa Helena de Aguiar
Chemical profile of Lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations
title Chemical profile of Lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations
title_full Chemical profile of Lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations
title_fullStr Chemical profile of Lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations
title_full_unstemmed Chemical profile of Lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations
title_short Chemical profile of Lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations
title_sort chemical profile of lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6407782/
https://www.ncbi.nlm.nih.gov/pubmed/30849129
http://dx.doi.org/10.1371/journal.pone.0213393
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