Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia

Autores
Vargas Méndez, Leonor Y.; Sanabria Flórez, Pedro L.; Saavedra Reyes, Laura Marcela; Merchan Arenas, Diego R.; Kouznetsov, Vladimir V.
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The anti-acetylcholinesterase, larvicidal, antifeedant activities and general toxicity of 15 semisynthetic eugenol derivatives based on clove oil (including the own oil), were evaluated against the maize armyworm, Spodoptera frugiperda (J.E. Smith). Therefore, promising eugenol molecules were classified with larvicidal, anti-acetylcholinesterase and antifeedant activities for controlling this pest. During structure–activity relationship studies and physicochemical profile analysis, it was found that among tested molecules 1-15, eugenol 1, prenyl eugenol 4, isoeugenol 8 and isoeugenol acetate 11 exhibited lethal effects LD50 at concentrations < 1 mg/g of insect. On the other hand, eugenol 1, metallyl eugenol 3, isoeugenol 8 and isoeugenol acetate 11 showed a good antifeedant activity (CE50 =158-209 µg/mL) with a high antifeedant index (70-78 %) at concentration 1000 µg/mL, possessing a weak antiacetylcholinesterase activity (IC50 = 21-31 g/mL). According to their ecotoxicological profiles (LC50 = 2033.1-6303.8 µg/mL on Artemia salina larvae), isoeugenol 8 and its acetate derivative 11 could be potential used in control of the growth, feeding, or reproduction of S. frugiperda larvae, acting as moderate insecticidal acetylcholinesterase inhibitors and/or antifeedant molecules. Such structure–activity relationship studies could stimulate the identification of lead structures from natural sources for the development of larvicidal and deterrent products against S. frugiperda and related insect pests.
Fil: Vargas Méndez, Leonor Y.. Universidad Santo Tomás; Colombia
Fil: Sanabria Flórez, Pedro L.. Universidad Santo Tomás; Colombia
Fil: Saavedra Reyes, Laura Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Santo Tomás; Colombia
Fil: Merchan Arenas, Diego R.. Universidad Industrial Santander; Colombia
Fil: Kouznetsov, Vladimir V.. Universidad Industrial Santander; Colombia
Materia
ACETYLCHOLINESTERASE ACTIVITY
ANTIFEEDANT ACTIVITY
CLOVE OIL
EUGENOL DERIVATIVES
INSECTICIDAL ACTIVITY
SPODOPTERA FRUGIPERDA
TOXICITY ON ARTEMIA SALINA LARVAE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/102225
Acceder
id CONICETDig_de9c4cc4e58c3cc0f9dae16d937e2f43
oai_identifier_str oai:ri.conicet.gov.ar:11336/102225
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in ColombiaVargas Méndez, Leonor Y.Sanabria Flórez, Pedro L.Saavedra Reyes, Laura MarcelaMerchan Arenas, Diego R.Kouznetsov, Vladimir V.ACETYLCHOLINESTERASE ACTIVITYANTIFEEDANT ACTIVITYCLOVE OILEUGENOL DERIVATIVESINSECTICIDAL ACTIVITYSPODOPTERA FRUGIPERDATOXICITY ON ARTEMIA SALINA LARVAEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The anti-acetylcholinesterase, larvicidal, antifeedant activities and general toxicity of 15 semisynthetic eugenol derivatives based on clove oil (including the own oil), were evaluated against the maize armyworm, Spodoptera frugiperda (J.E. Smith). Therefore, promising eugenol molecules were classified with larvicidal, anti-acetylcholinesterase and antifeedant activities for controlling this pest. During structure–activity relationship studies and physicochemical profile analysis, it was found that among tested molecules 1-15, eugenol 1, prenyl eugenol 4, isoeugenol 8 and isoeugenol acetate 11 exhibited lethal effects LD50 at concentrations < 1 mg/g of insect. On the other hand, eugenol 1, metallyl eugenol 3, isoeugenol 8 and isoeugenol acetate 11 showed a good antifeedant activity (CE50 =158-209 µg/mL) with a high antifeedant index (70-78 %) at concentration 1000 µg/mL, possessing a weak antiacetylcholinesterase activity (IC50 = 21-31 g/mL). According to their ecotoxicological profiles (LC50 = 2033.1-6303.8 µg/mL on Artemia salina larvae), isoeugenol 8 and its acetate derivative 11 could be potential used in control of the growth, feeding, or reproduction of S. frugiperda larvae, acting as moderate insecticidal acetylcholinesterase inhibitors and/or antifeedant molecules. Such structure–activity relationship studies could stimulate the identification of lead structures from natural sources for the development of larvicidal and deterrent products against S. frugiperda and related insect pests.Fil: Vargas Méndez, Leonor Y.. Universidad Santo Tomás; ColombiaFil: Sanabria Flórez, Pedro L.. Universidad Santo Tomás; ColombiaFil: Saavedra Reyes, Laura Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Santo Tomás; ColombiaFil: Merchan Arenas, Diego R.. Universidad Industrial Santander; ColombiaFil: Kouznetsov, Vladimir V.. Universidad Industrial Santander; ColombiaElsevier2018-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/102225Vargas Méndez, Leonor Y.; Sanabria Flórez, Pedro L.; Saavedra Reyes, Laura Marcela; Merchan Arenas, Diego R.; Kouznetsov, Vladimir V.; Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia; Elsevier; Saudi Journal of Biological Sciences; 26; 7; 9-2018; 1613-16201319-562XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.sjbs.2018.09.010info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1319562X18302262info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:46:37Zoai:ri.conicet.gov.ar:11336/102225instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:46:38.188CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia
title Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia
spellingShingle Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia
Vargas Méndez, Leonor Y.
ACETYLCHOLINESTERASE ACTIVITY
ANTIFEEDANT ACTIVITY
CLOVE OIL
EUGENOL DERIVATIVES
INSECTICIDAL ACTIVITY
SPODOPTERA FRUGIPERDA
TOXICITY ON ARTEMIA SALINA LARVAE
title_short Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia
title_full Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia
title_fullStr Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia
title_full_unstemmed Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia
title_sort Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia
dc.creator.none.fl_str_mv Vargas Méndez, Leonor Y.
Sanabria Flórez, Pedro L.
Saavedra Reyes, Laura Marcela
Merchan Arenas, Diego R.
Kouznetsov, Vladimir V.
author Vargas Méndez, Leonor Y.
author_facet Vargas Méndez, Leonor Y.
Sanabria Flórez, Pedro L.
Saavedra Reyes, Laura Marcela
Merchan Arenas, Diego R.
Kouznetsov, Vladimir V.
author_role author
author2 Sanabria Flórez, Pedro L.
Saavedra Reyes, Laura Marcela
Merchan Arenas, Diego R.
Kouznetsov, Vladimir V.
author2_role author
author
author
author
dc.subject.none.fl_str_mv ACETYLCHOLINESTERASE ACTIVITY
ANTIFEEDANT ACTIVITY
CLOVE OIL
EUGENOL DERIVATIVES
INSECTICIDAL ACTIVITY
SPODOPTERA FRUGIPERDA
TOXICITY ON ARTEMIA SALINA LARVAE
topic ACETYLCHOLINESTERASE ACTIVITY
ANTIFEEDANT ACTIVITY
CLOVE OIL
EUGENOL DERIVATIVES
INSECTICIDAL ACTIVITY
SPODOPTERA FRUGIPERDA
TOXICITY ON ARTEMIA SALINA LARVAE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The anti-acetylcholinesterase, larvicidal, antifeedant activities and general toxicity of 15 semisynthetic eugenol derivatives based on clove oil (including the own oil), were evaluated against the maize armyworm, Spodoptera frugiperda (J.E. Smith). Therefore, promising eugenol molecules were classified with larvicidal, anti-acetylcholinesterase and antifeedant activities for controlling this pest. During structure–activity relationship studies and physicochemical profile analysis, it was found that among tested molecules 1-15, eugenol 1, prenyl eugenol 4, isoeugenol 8 and isoeugenol acetate 11 exhibited lethal effects LD50 at concentrations < 1 mg/g of insect. On the other hand, eugenol 1, metallyl eugenol 3, isoeugenol 8 and isoeugenol acetate 11 showed a good antifeedant activity (CE50 =158-209 µg/mL) with a high antifeedant index (70-78 %) at concentration 1000 µg/mL, possessing a weak antiacetylcholinesterase activity (IC50 = 21-31 g/mL). According to their ecotoxicological profiles (LC50 = 2033.1-6303.8 µg/mL on Artemia salina larvae), isoeugenol 8 and its acetate derivative 11 could be potential used in control of the growth, feeding, or reproduction of S. frugiperda larvae, acting as moderate insecticidal acetylcholinesterase inhibitors and/or antifeedant molecules. Such structure–activity relationship studies could stimulate the identification of lead structures from natural sources for the development of larvicidal and deterrent products against S. frugiperda and related insect pests.
Fil: Vargas Méndez, Leonor Y.. Universidad Santo Tomás; Colombia
Fil: Sanabria Flórez, Pedro L.. Universidad Santo Tomás; Colombia
Fil: Saavedra Reyes, Laura Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Santo Tomás; Colombia
Fil: Merchan Arenas, Diego R.. Universidad Industrial Santander; Colombia
Fil: Kouznetsov, Vladimir V.. Universidad Industrial Santander; Colombia
description The anti-acetylcholinesterase, larvicidal, antifeedant activities and general toxicity of 15 semisynthetic eugenol derivatives based on clove oil (including the own oil), were evaluated against the maize armyworm, Spodoptera frugiperda (J.E. Smith). Therefore, promising eugenol molecules were classified with larvicidal, anti-acetylcholinesterase and antifeedant activities for controlling this pest. During structure–activity relationship studies and physicochemical profile analysis, it was found that among tested molecules 1-15, eugenol 1, prenyl eugenol 4, isoeugenol 8 and isoeugenol acetate 11 exhibited lethal effects LD50 at concentrations < 1 mg/g of insect. On the other hand, eugenol 1, metallyl eugenol 3, isoeugenol 8 and isoeugenol acetate 11 showed a good antifeedant activity (CE50 =158-209 µg/mL) with a high antifeedant index (70-78 %) at concentration 1000 µg/mL, possessing a weak antiacetylcholinesterase activity (IC50 = 21-31 g/mL). According to their ecotoxicological profiles (LC50 = 2033.1-6303.8 µg/mL on Artemia salina larvae), isoeugenol 8 and its acetate derivative 11 could be potential used in control of the growth, feeding, or reproduction of S. frugiperda larvae, acting as moderate insecticidal acetylcholinesterase inhibitors and/or antifeedant molecules. Such structure–activity relationship studies could stimulate the identification of lead structures from natural sources for the development of larvicidal and deterrent products against S. frugiperda and related insect pests.
publishDate 2018
dc.date.none.fl_str_mv 2018-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/102225
Vargas Méndez, Leonor Y.; Sanabria Flórez, Pedro L.; Saavedra Reyes, Laura Marcela; Merchan Arenas, Diego R.; Kouznetsov, Vladimir V.; Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia; Elsevier; Saudi Journal of Biological Sciences; 26; 7; 9-2018; 1613-1620
1319-562X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/102225
identifier_str_mv Vargas Méndez, Leonor Y.; Sanabria Flórez, Pedro L.; Saavedra Reyes, Laura Marcela; Merchan Arenas, Diego R.; Kouznetsov, Vladimir V.; Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia; Elsevier; Saudi Journal of Biological Sciences; 26; 7; 9-2018; 1613-1620
1319-562X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.sjbs.2018.09.010
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1319562X18302262
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1844614508337692672
score 13.070432

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