The antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strain
Currently, no specific licensed antiviral exists for treating the illness caused by dengue virus (DENV). Therefore, the search for compounds of natural origin with antiviral activity is an important area of research. In the present study, three compounds were isolated and identified from seeds of Ta...
- Autores:
-
Monsalve Escudero, Laura
Loaiza Cano, Vanessa
Zapata Cardona, María Isabel
Quintero Gil, Diana Carolina
Hernandez Mira, Estiven
Pajaro Gonzalez, Yina
Oliveros Diaz, Andres
Diaz Castillo, Fredyc
Quiñones, Wiston
Robledo, Sara
Martínez Gutiérrez, Marlén
- Tipo de recurso:
- Article of investigation
- Fecha de publicación:
- 2021
- Institución:
- Universidad Cooperativa de Colombia
- Repositorio:
- Repositorio UCC
- Idioma:
- OAI Identifier:
- oai:repository.ucc.edu.co:20.500.12494/43618
- Acceso en línea:
- https://hdl.handle.net/20.500.12494/43618
- Palabra clave:
- dengue virus
Tabernaemontana cymosa
indole alkaloids
molecular docking
antivirals
- Rights
- openAccess
- License
- Atribución – No comercial – Compartir igual
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| dc.title.spa.fl_str_mv |
The antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strain |
| title |
The antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strain |
| spellingShingle |
The antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strain dengue virus Tabernaemontana cymosa indole alkaloids molecular docking antivirals |
| title_short |
The antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strain |
| title_full |
The antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strain |
| title_fullStr |
The antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strain |
| title_full_unstemmed |
The antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strain |
| title_sort |
The antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strain |
| dc.creator.fl_str_mv |
Monsalve Escudero, Laura Loaiza Cano, Vanessa Zapata Cardona, María Isabel Quintero Gil, Diana Carolina Hernandez Mira, Estiven Pajaro Gonzalez, Yina Oliveros Diaz, Andres Diaz Castillo, Fredyc Quiñones, Wiston Robledo, Sara Martínez Gutiérrez, Marlén |
| dc.contributor.author.none.fl_str_mv |
Monsalve Escudero, Laura Loaiza Cano, Vanessa Zapata Cardona, María Isabel Quintero Gil, Diana Carolina Hernandez Mira, Estiven Pajaro Gonzalez, Yina Oliveros Diaz, Andres Diaz Castillo, Fredyc Quiñones, Wiston Robledo, Sara Martínez Gutiérrez, Marlén |
| dc.subject.spa.fl_str_mv |
dengue virus Tabernaemontana cymosa indole alkaloids molecular docking antivirals |
| topic |
dengue virus Tabernaemontana cymosa indole alkaloids molecular docking antivirals |
| description |
Currently, no specific licensed antiviral exists for treating the illness caused by dengue virus (DENV). Therefore, the search for compounds of natural origin with antiviral activity is an important area of research. In the present study, three compounds were isolated and identified from seeds of Tabernaemontana cymosa plants. The in vitro antiviral effect of those compounds and voacangine against different DENV strains was assessed using different experimental approaches: compounds added before the infection (Pre), at the same time with the virus (Trans), after the infection (Post) or compounds present in all moments of the experiment (Pre-Trans-Post, Combined treatment). In silico studies (docking and molecular dynamics) were also performed to explain the possible antiviral mechanisms. The identified compounds were three structural analogs of voacangine (voacangine-7-hydroxyindolenine, rupicoline and 3-oxo-voacangine). In the Pre-treatment, only voacangine-7-hydroxyindolenine and rupicoline inhibited the infection caused by the DENV-2/NG strain (16.4% and 29.6% infection, respectively). In the Trans-treatment approach, voacangine, voacangine-7-hydroxyindolenine and rupicoline inhibited the infection in both DENV-2/NG (11.2%, 80.4% and 75.7% infection, respectively) and DENV-2/16681 infection models (73.7%, 74.0% and 75.3% infection, respectively). The latter strain was also inhibited by 3-oxo-voacangine (82.8% infection). Moreover, voacangine (most effective virucidal agent) was also effective against one strain of DENV-1 (DENV-1/WestPac/74) and against the third strain of DENV-2 (DENV-2/S16803) (48.5% and 32.4% infection, respectively). Conversely, no inhibition was observed in the post-treatment approach. The last approach (combined) showed that voacangine, voacangine-7-hydroxyindolenine and rupicoline inhibited over 90% of infections (3.5%, 6.9% and 3.5% infection, respectively) of both strains (DENV-2/NG and DENV-2/16681). The free energy of binding obtained with an in silico approach was favorable for the E protein and compounds, which ranged between −5.1 and −6.3 kcal/mol. Finally, the complex formed between DENV-2 E protein and the best virucidal compound was stable for 50 ns. Our results show that the antiviral effect of indole alkaloids derived from T. cymose depends on the serotype and the virus strain. |
| publishDate |
2021 |
| dc.date.issued.none.fl_str_mv |
2021-06 |
| dc.date.accessioned.none.fl_str_mv |
2022-02-02T22:35:04Z |
| dc.date.available.none.fl_str_mv |
2022-02-02T22:35:04Z |
| dc.type.none.fl_str_mv |
Artículos Científicos |
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http://purl.org/coar/resource_type/c_2df8fbb1 |
| dc.type.coarversion.none.fl_str_mv |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
| dc.type.driver.none.fl_str_mv |
info:eu-repo/semantics/article |
| dc.type.version.none.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| format |
http://purl.org/coar/resource_type/c_2df8fbb1 |
| status_str |
publishedVersion |
| dc.identifier.issn.spa.fl_str_mv |
2223-7747 |
| dc.identifier.uri.spa.fl_str_mv |
doi.org/10.3390/plants10071280 |
| dc.identifier.uri.none.fl_str_mv |
https://hdl.handle.net/20.500.12494/43618 |
| dc.identifier.bibliographicCitation.spa.fl_str_mv |
Monsalve-Escudero, L.M.; Loaiza-Cano, V.; Zapata-Cardona, M.I.; Quintero-Gil, D.C.; Hernández-Mira, E.; Pájaro-González, Y.; Oliveros-Díaz, A.F.; Diaz-Castillo, F.; Quiñones, W.; Robledo, S.; Martinez-Gutierrez, M. The Antiviral and Virucidal Activities of Voacangine and Structural Analogs Extracted from Tabernaemontana cymosa Depend on the Dengue Virus Strain. Plants 2021, 10, 1280. https://doi.org/10.3390/plants10071280 |
| identifier_str_mv |
2223-7747 doi.org/10.3390/plants10071280 Monsalve-Escudero, L.M.; Loaiza-Cano, V.; Zapata-Cardona, M.I.; Quintero-Gil, D.C.; Hernández-Mira, E.; Pájaro-González, Y.; Oliveros-Díaz, A.F.; Diaz-Castillo, F.; Quiñones, W.; Robledo, S.; Martinez-Gutierrez, M. The Antiviral and Virucidal Activities of Voacangine and Structural Analogs Extracted from Tabernaemontana cymosa Depend on the Dengue Virus Strain. Plants 2021, 10, 1280. https://doi.org/10.3390/plants10071280 |
| url |
https://hdl.handle.net/20.500.12494/43618 |
| dc.relation.isversionof.spa.fl_str_mv |
https://www.mdpi.com/2223-7747/10/7/1280 |
| dc.relation.ispartofjournal.spa.fl_str_mv |
Plants |
| dc.relation.references.spa.fl_str_mv |
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Universidad Cooperativa de Colombia, Facultad de Ciencias de la Salud, Medicina Veterinaría y Zootecnia, Bucaramanga MDPI |
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Monsalve Escudero, LauraLoaiza Cano, VanessaZapata Cardona, María IsabelQuintero Gil, Diana CarolinaHernandez Mira, EstivenPajaro Gonzalez, YinaOliveros Diaz, AndresDiaz Castillo, FredycQuiñones, WistonRobledo, SaraMartínez Gutiérrez, Marlén102022-02-02T22:35:04Z2022-02-02T22:35:04Z2021-062223-7747doi.org/10.3390/plants10071280https://hdl.handle.net/20.500.12494/43618Monsalve-Escudero, L.M.; Loaiza-Cano, V.; Zapata-Cardona, M.I.; Quintero-Gil, D.C.; Hernández-Mira, E.; Pájaro-González, Y.; Oliveros-Díaz, A.F.; Diaz-Castillo, F.; Quiñones, W.; Robledo, S.; Martinez-Gutierrez, M. The Antiviral and Virucidal Activities of Voacangine and Structural Analogs Extracted from Tabernaemontana cymosa Depend on the Dengue Virus Strain. Plants 2021, 10, 1280. https://doi.org/10.3390/plants10071280Currently, no specific licensed antiviral exists for treating the illness caused by dengue virus (DENV). Therefore, the search for compounds of natural origin with antiviral activity is an important area of research. In the present study, three compounds were isolated and identified from seeds of Tabernaemontana cymosa plants. The in vitro antiviral effect of those compounds and voacangine against different DENV strains was assessed using different experimental approaches: compounds added before the infection (Pre), at the same time with the virus (Trans), after the infection (Post) or compounds present in all moments of the experiment (Pre-Trans-Post, Combined treatment). In silico studies (docking and molecular dynamics) were also performed to explain the possible antiviral mechanisms. The identified compounds were three structural analogs of voacangine (voacangine-7-hydroxyindolenine, rupicoline and 3-oxo-voacangine). In the Pre-treatment, only voacangine-7-hydroxyindolenine and rupicoline inhibited the infection caused by the DENV-2/NG strain (16.4% and 29.6% infection, respectively). In the Trans-treatment approach, voacangine, voacangine-7-hydroxyindolenine and rupicoline inhibited the infection in both DENV-2/NG (11.2%, 80.4% and 75.7% infection, respectively) and DENV-2/16681 infection models (73.7%, 74.0% and 75.3% infection, respectively). The latter strain was also inhibited by 3-oxo-voacangine (82.8% infection). Moreover, voacangine (most effective virucidal agent) was also effective against one strain of DENV-1 (DENV-1/WestPac/74) and against the third strain of DENV-2 (DENV-2/S16803) (48.5% and 32.4% infection, respectively). Conversely, no inhibition was observed in the post-treatment approach. The last approach (combined) showed that voacangine, voacangine-7-hydroxyindolenine and rupicoline inhibited over 90% of infections (3.5%, 6.9% and 3.5% infection, respectively) of both strains (DENV-2/NG and DENV-2/16681). The free energy of binding obtained with an in silico approach was favorable for the E protein and compounds, which ranged between −5.1 and −6.3 kcal/mol. Finally, the complex formed between DENV-2 E protein and the best virucidal compound was stable for 50 ns. Our results show that the antiviral effect of indole alkaloids derived from T. cymose depends on the serotype and the virus strain.https://scienti.colciencias.gov.co/cvlac/visualizador/generarCurriculoCv.do?cod_rh=0000213748https://orcid.org/0000-0002-9429-0058https://scienti.minciencias.gov.co/gruplac/jsp/visualiza/visualizagr.jsp?nro=00000000000695Marlen.martinezg@campucucc.edu.cohttps://scholar.google.es/citations?user=flSrsSIAAAAJ&hl=es1280Universidad Cooperativa de Colombia, Facultad de Ciencias de la Salud, Medicina Veterinaría y Zootecnia, BucaramangaMDPIMedicina veterinaria y zootecniaBucaramangahttps://www.mdpi.com/2223-7747/10/7/1280PlantsTapia-Conyer, R.; Betancourt-Cravioto, M.; Méndez-Galván, J. Dengue: An escalating public health problem in Latin America. Paediatr. Int. Child Health 2012, 32, 14–17.Gubler, D.J. Aedes aegypti and Aedes aegypti-Borne Disease Control in the 1990s: Top Down or Bottom Up. Am. J. Trop. Med. 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Bioinform. 2017, 6, 9.dengue virusTabernaemontana cymosaindole alkaloidsmolecular dockingantiviralsThe antiviral and virucidal activities of voacangine and structural analogs extracted from Tabernaemontana cymosa depend on the Dengue virus strainArtículos Científicoshttp://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionAtribución – No comercial – Compartir igualinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2PublicationORIGINALplants-10-01280.pdfplants-10-01280.pdfArtículoapplication/pdf7182184https://repository.ucc.edu.co/bitstreams/06a37663-3fbe-4754-ba01-cac4b7c29c5e/download12eb89b50ebbdbf14c067b9ef53cdbe1MD51Licencia de uso Plants.pdfLicencia de uso Plants.pdfLicencia de 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