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...

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Autores:
Monsalve-Escudero, Laura Milena
Tipo de recurso:
Fecha de publicación:
2021
Institución:
Universidad del Atlántico
Repositorio:
Repositorio Uniatlantico
Idioma:
eng
OAI Identifier:
oai:repositorio.uniatlantico.edu.co:20.500.12834/1160
Acceso en línea:
https://hdl.handle.net/20.500.12834/1160
Palabra clave:
dengue virus; Tabernaemontana cymosa; indole alkaloids; molecular docking; antivirals
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openAccess
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http://creativecommons.org/licenses/by-nc/4.0/
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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
dc.title.alternative.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 Milena
dc.contributor.author.none.fl_str_mv Monsalve-Escudero, Laura Milena
dc.contributor.other.none.fl_str_mv Loaiza-Cano, Vanessa
Zapata-Cardona, Maria Isabel
Quintero-Gil, Diana Carolina
Hernández-Mira, Estiven
Pájaro-González, Yina
Oliveros-Díaz, Andrés Felipe
Diaz-Castillo, Fredyc
Quiñones, Wistón
Robledo, Sara
Martinez-Gutierrez, Marlen
dc.subject.keywords.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 2021-06-23
dc.date.submitted.none.fl_str_mv 2021-05-15
dc.date.accessioned.none.fl_str_mv 2022-12-20T19:22:44Z
dc.date.available.none.fl_str_mv 2022-12-20T19:22:44Z
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dc.identifier.citation.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.; et al. 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
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/20.500.12834/1160
dc.identifier.doi.none.fl_str_mv 10.3390/ plants10071280
dc.identifier.instname.spa.fl_str_mv Universidad del Atlántico
dc.identifier.reponame.spa.fl_str_mv Repositorio Universidad del Atlántico
identifier_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.; et al. 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
10.3390/ plants10071280
Universidad del Atlántico
Repositorio Universidad del Atlántico
url https://hdl.handle.net/20.500.12834/1160
dc.language.iso.spa.fl_str_mv eng
language eng
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eu_rights_str_mv openAccess
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.place.spa.fl_str_mv Barranquilla
dc.publisher.discipline.spa.fl_str_mv Maestría en Gestión Farmacéutica
dc.publisher.sede.spa.fl_str_mv Sede Norte
dc.source.spa.fl_str_mv Plants
institution Universidad del Atlántico
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spelling Monsalve-Escudero, Laura Milenac1300c67-e8a5-4602-be12-bd49a2e13c5fLoaiza-Cano, VanessaZapata-Cardona, Maria IsabelQuintero-Gil, Diana CarolinaHernández-Mira, EstivenPájaro-González, YinaOliveros-Díaz, Andrés FelipeDiaz-Castillo, FredycQuiñones, WistónRobledo, SaraMartinez-Gutierrez, Marlen2022-12-20T19:22:44Z2022-12-20T19:22:44Z2021-06-232021-05-15Monsalve-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.; et al. 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/ plants10071280https://hdl.handle.net/20.500.12834/116010.3390/ plants10071280Universidad del AtlánticoRepositorio Universidad del AtlánticoCurrently, 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.application/pdfenghttp://creativecommons.org/licenses/by-nc/4.0/Attribution-NonCommercial 4.0 Internationalinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2PlantsThe Antiviral and Virucidal Activities of Voacangine and Structural Analogs Extracted from Tabernaemontana cymosa Depend on the Dengue Virus StrainThe Antiviral and Virucidal Activities of Voacangine and Structural Analogs Extracted from Tabernaemontana cymosa Depend on the Dengue Virus StrainPúblico generaldengue virus; Tabernaemontana cymosa; indole alkaloids; molecular docking; antiviralsinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArtículohttp://purl.org/coar/version/c_970fb48d4fbd8a85http://purl.org/coar/resource_type/c_2df8fbb1BarranquillaMaestría en Gestión FarmacéuticaSede NorteTapia-Conyer, R.; Betancourt-Cravioto, M.; Méndez-Galván, J. 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[Google Scholar] [CrossRef]http://purl.org/coar/resource_type/c_2df8fbb1ORIGINALplants-10-01280.pdfplants-10-01280.pdfapplication/pdf7182184https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/1160/1/plants-10-01280.pdf12eb89b50ebbdbf14c067b9ef53cdbe1MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8914https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/1160/2/license_rdf24013099e9e6abb1575dc6ce0855efd5MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81306https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/1160/3/license.txt67e239713705720ef0b79c50b2ececcaMD5320.500.12834/1160oai:repositorio.uniatlantico.edu.co:20.500.12834/11602022-12-20 14:22:45.496DSpace de la Universidad de Atlánticosysadmin@mail.uniatlantico.edu.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