In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase
Zephyranthes carinata Herb., a specie of the Amaryllidoideae subfamily, has been reported to have inhibitory activity against acetylcholinesterase. However, scientific evidence related to their bioactive alkaloids has been lacking. Thus, this study describes the isolation of the alkaloids of this pl...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2022-06-01
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| Series: | Biomedicine & Pharmacotherapy |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S075333222200405X |
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| author | Karina Sierra Jean Paulo de Andrade Luciana R. Tallini Edison H. Osorio Osvaldo Yañéz Manuel Isaías Osorio Nora H. Oleas Olimpo García-Beltrán Warley de S. Borges Jaume Bastida Edison Osorio Natalie Cortes |
| author_facet | Karina Sierra Jean Paulo de Andrade Luciana R. Tallini Edison H. Osorio Osvaldo Yañéz Manuel Isaías Osorio Nora H. Oleas Olimpo García-Beltrán Warley de S. Borges Jaume Bastida Edison Osorio Natalie Cortes |
| author_sort | Karina Sierra |
| collection | DOAJ |
| description | Zephyranthes carinata Herb., a specie of the Amaryllidoideae subfamily, has been reported to have inhibitory activity against acetylcholinesterase. However, scientific evidence related to their bioactive alkaloids has been lacking. Thus, this study describes the isolation of the alkaloids of this plant, and their inhibition of the enzymes acetylcholinesterase (eeAChE) and butyrylcholinesterase (eqBuChE), being galanthine the main component. Additionally, haemanthamine, hamayne, lycoramine, lycorine, tazettine, trisphaeridine and vittatine/crinine were also isolated. The results showed that galanthine has significant activity at low micromolar concentrations for eeAChE (IC50 = 1.96 μg/mL). The in-silico study allowed to establish at a molecular level the high affinity and the way galanthine interacts with the active site of the TcAChE enzyme, information that corroborates the result of the experimental IC50. However, according to molecular dynamics (MD) analysis, it is also suggested that galanthine presents a different inhibition mode that the one observed for galanthamine, by presenting interaction with peripheral anionic binding site of the enzyme, which prevents the entrance and exit of molecules from the active site. Thus, in vitro screening assays plus rapid computer development play an essential role in the search for new cholinesterase inhibitors by identifying unknown bio-interactions between bioactive compounds and biological targets. |
| first_indexed | 2024-04-12T16:52:40Z |
| format | Article |
| id | doaj.art-50554eb6e7f24cd99e2de4c5d7ac577b |
| institution | Directory Open Access Journal |
| issn | 0753-3322 |
| language | English |
| last_indexed | 2024-04-12T16:52:40Z |
| publishDate | 2022-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Biomedicine & Pharmacotherapy |
| spelling | doaj.art-50554eb6e7f24cd99e2de4c5d7ac577b2022-12-22T03:24:21ZengElsevierBiomedicine & Pharmacotherapy0753-33222022-06-01150113016In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesteraseKarina Sierra0Jean Paulo de Andrade1Luciana R. Tallini2Edison H. Osorio3Osvaldo Yañéz4Manuel Isaías Osorio5Nora H. Oleas6Olimpo García-Beltrán7Warley de S. Borges8Jaume Bastida9Edison Osorio10Natalie Cortes11Grupo de Investigación en Sustancias Bioactivas, Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquía UdeA, Calle 70 No. 52-21, Medellín, ColombiaNúcleo Científico Multidisciplinario, Dirección de Investigación, Universidad de Talca, Campus Lircay, CP 3460000, Talca, ChilePrograma de Pós-graduação em Ciências Farmacêuticas, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-0000 Porto Alegre, Brazil; Grup de Productes Naturals, Departament de Biologia, Sanitat i Medi Ambient, Facultat de Farmàcia i Ciències de l′Alimentació, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, SpainFacultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 calle 67, Ibagué, ColombiaCenter of New Drugs for Hypertension (CENDHY), Santiago 8380494, Chile; Facultad de Ingeniería y Negocios, Universidad de las Américas, Santiago 7500000, ChileCenter for Bioinformatics and Integrative Biology (CBIB), Facultad de Ciencias de la Vida, Universidad Andres Bello, Santiago, Chile; Facultad de Medicina, Universidad Diego Portales, Santiago, ChileCentro de Investigación de la Biodiversidad y Cambio Climático (BioCamb) e Ingeniería en Biodiversidad y Recursos Genéticos, Facultad de Ciencias de Medio Ambiente, Universidad Tecnológica Indoamérica, Machala y Sabanilla, EC170301 Quito, EcuadorFacultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 calle 67, Ibagué, ColombiaDepartamento de Química, Universidade Federal do Espírito Santo, Avenida Fernando Ferrari 514, Goiabeiras, 29075-910 Vitória, Espírito Santo, BrazilGrup de Productes Naturals, Departament de Biologia, Sanitat i Medi Ambient, Facultat de Farmàcia i Ciències de l′Alimentació, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, SpainGrupo de Investigación en Sustancias Bioactivas, Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquía UdeA, Calle 70 No. 52-21, Medellín, Colombia; Corresponding authors.Facultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 calle 67, Ibagué, Colombia; Corresponding authors.Zephyranthes carinata Herb., a specie of the Amaryllidoideae subfamily, has been reported to have inhibitory activity against acetylcholinesterase. However, scientific evidence related to their bioactive alkaloids has been lacking. Thus, this study describes the isolation of the alkaloids of this plant, and their inhibition of the enzymes acetylcholinesterase (eeAChE) and butyrylcholinesterase (eqBuChE), being galanthine the main component. Additionally, haemanthamine, hamayne, lycoramine, lycorine, tazettine, trisphaeridine and vittatine/crinine were also isolated. The results showed that galanthine has significant activity at low micromolar concentrations for eeAChE (IC50 = 1.96 μg/mL). The in-silico study allowed to establish at a molecular level the high affinity and the way galanthine interacts with the active site of the TcAChE enzyme, information that corroborates the result of the experimental IC50. However, according to molecular dynamics (MD) analysis, it is also suggested that galanthine presents a different inhibition mode that the one observed for galanthamine, by presenting interaction with peripheral anionic binding site of the enzyme, which prevents the entrance and exit of molecules from the active site. Thus, in vitro screening assays plus rapid computer development play an essential role in the search for new cholinesterase inhibitors by identifying unknown bio-interactions between bioactive compounds and biological targets.http://www.sciencedirect.com/science/article/pii/S075333222200405XAmaryllidaceae alkaloidsGalanthineAcetylcholinesterase inhibitionMolecular dockingMolecular dynamics |
| spellingShingle | Karina Sierra Jean Paulo de Andrade Luciana R. Tallini Edison H. Osorio Osvaldo Yañéz Manuel Isaías Osorio Nora H. Oleas Olimpo García-Beltrán Warley de S. Borges Jaume Bastida Edison Osorio Natalie Cortes In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase Biomedicine & Pharmacotherapy Amaryllidaceae alkaloids Galanthine Acetylcholinesterase inhibition Molecular docking Molecular dynamics |
| title | In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase |
| title_full | In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase |
| title_fullStr | In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase |
| title_full_unstemmed | In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase |
| title_short | In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase |
| title_sort | in vitro and in silico analysis of galanthine from zephyranthes carinata as an inhibitor of acetylcholinesterase |
| topic | Amaryllidaceae alkaloids Galanthine Acetylcholinesterase inhibition Molecular docking Molecular dynamics |
| url | http://www.sciencedirect.com/science/article/pii/S075333222200405X |
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