Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship

Autores
Zaio, Yésica Paola; Gatti, Gerardo Alberto; Ponce, Andrés Alberto; Saavedra Larralde, Natalia; Martinez, María J.; Zunino, María Paula; Zygadlo, Julio Alberto
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Insecticidal activity and repellent effects on adults of Sitophiluszeamais of 12 cinnamaldehyde-related compounds was evaluated by contacttoxicity bioassays and a two-choice olfactometer, respectively. To determinenon-toxicity in mammals, additionally, body weight, serum biochemical profiles,liver weight, physiological parameters, sperm motility and histopathological data were obtained as complementary information in C57BL/6 mice, treated with the best natural compound. RESULTS: Based on 24h LC95 and LC50 values, alpha-methyl-cinnamaldehydeand cinnamaldehyde, respectively, exhibited better insecticidal activity than the other compounds. The best repellent effect was observed with alpha-bromocinnamaldehyde, which even repelled at the lowest concentration studied (0.28µM). The evaluation of a quantitative structure-activity relationship showed a linear relationship between the LC50 values for adult weevil toxicity and dipolo with Q (difference between orbital electronegativity carbon 1 and orbital electronegativity carbon 3 of the molecule) values in cinnamaldehyde-related compounds. In addition, the polar surface and Log P descriptors also revealed a linear relationship with the S. zeamais repellent effect for cinnamaldehyde analogues. Besides, cinnamaldehyde did not show toxicity in the parameters evaluated in mice.CONCLUSION: From the phenylpropanoid components studied, the naturalcompound which had the best insecticidal and repellent activity against S.zeamais was cinnamaldehyde and presented no mammalian toxicity.
Fil: Zaio, Yésica Paola. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto de Ciencias y Tecnología de los Alimentos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Gatti, Gerardo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina. Fundación Para Progreso Medicina-hospital Privado; Argentina
Fil: Ponce, Andrés Alberto. Fundación Para El Progreso de la Medicina; Argentina
Fil: Saavedra Larralde, Natalia. Universidad Nacional de Córdoba. Facultad de Medicina. Departamento de Fisiología Humana y Física Biomedica; Argentina
Fil: Martinez, María J.. Universidad Nacional de Córdoba. Facultad de Medicina; Argentina
Fil: Zunino, María Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Zygadlo, Julio Alberto. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto de Ciencias y Tecnología de los Alimentos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Materia
CINNAMALDEHYDE-RELATED STRUCTURES
INSECTICIDAL PROPERTY
QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP
REPELLENT EFFECT
SITOPHILUS ZEAMAIS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/86567
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/86567
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationshipZaio, Yésica PaolaGatti, Gerardo AlbertoPonce, Andrés AlbertoSaavedra Larralde, NataliaMartinez, María J.Zunino, María PaulaZygadlo, Julio AlbertoCINNAMALDEHYDE-RELATED STRUCTURESINSECTICIDAL PROPERTYQUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPREPELLENT EFFECTSITOPHILUS ZEAMAIShttps://purl.org/becyt/ford/1.7https://purl.org/becyt/ford/1Insecticidal activity and repellent effects on adults of Sitophiluszeamais of 12 cinnamaldehyde-related compounds was evaluated by contacttoxicity bioassays and a two-choice olfactometer, respectively. To determinenon-toxicity in mammals, additionally, body weight, serum biochemical profiles,liver weight, physiological parameters, sperm motility and histopathological data were obtained as complementary information in C57BL/6 mice, treated with the best natural compound. RESULTS: Based on 24h LC95 and LC50 values, alpha-methyl-cinnamaldehydeand cinnamaldehyde, respectively, exhibited better insecticidal activity than the other compounds. The best repellent effect was observed with alpha-bromocinnamaldehyde, which even repelled at the lowest concentration studied (0.28µM). The evaluation of a quantitative structure-activity relationship showed a linear relationship between the LC50 values for adult weevil toxicity and dipolo with Q (difference between orbital electronegativity carbon 1 and orbital electronegativity carbon 3 of the molecule) values in cinnamaldehyde-related compounds. In addition, the polar surface and Log P descriptors also revealed a linear relationship with the S. zeamais repellent effect for cinnamaldehyde analogues. Besides, cinnamaldehyde did not show toxicity in the parameters evaluated in mice.CONCLUSION: From the phenylpropanoid components studied, the naturalcompound which had the best insecticidal and repellent activity against S.zeamais was cinnamaldehyde and presented no mammalian toxicity.Fil: Zaio, Yésica Paola. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto de Ciencias y Tecnología de los Alimentos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Gatti, Gerardo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina. Fundación Para Progreso Medicina-hospital Privado; ArgentinaFil: Ponce, Andrés Alberto. Fundación Para El Progreso de la Medicina; ArgentinaFil: Saavedra Larralde, Natalia. Universidad Nacional de Córdoba. Facultad de Medicina. Departamento de Fisiología Humana y Física Biomedica; ArgentinaFil: Martinez, María J.. Universidad Nacional de Córdoba. Facultad de Medicina; ArgentinaFil: Zunino, María Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Zygadlo, Julio Alberto. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto de Ciencias y Tecnología de los Alimentos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaJohn Wiley & Sons Ltd2018-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/86567Zaio, Yésica Paola; Gatti, Gerardo Alberto; Ponce, Andrés Alberto; Saavedra Larralde, Natalia; Martinez, María J.; et al.; Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship; John Wiley & Sons Ltd; Journal of the Science of Food and Agriculture; 98; 15; 12-2018; 5822-58310022-51421097-0010CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://doi.wiley.com/10.1002/jsfa.9132info:eu-repo/semantics/altIdentifier/doi/10.1002/jsfa.9132info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1002/jsfa.9132info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:04:01Zoai:ri.conicet.gov.ar:11336/86567instacron: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:34982025-10-22 11:04:02.117CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship
title Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship
spellingShingle Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship
Zaio, Yésica Paola
CINNAMALDEHYDE-RELATED STRUCTURES
INSECTICIDAL PROPERTY
QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP
REPELLENT EFFECT
SITOPHILUS ZEAMAIS
title_short Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship
title_full Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship
title_fullStr Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship
title_full_unstemmed Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship
title_sort Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship
dc.creator.none.fl_str_mv Zaio, Yésica Paola
Gatti, Gerardo Alberto
Ponce, Andrés Alberto
Saavedra Larralde, Natalia
Martinez, María J.
Zunino, María Paula
Zygadlo, Julio Alberto
author Zaio, Yésica Paola
author_facet Zaio, Yésica Paola
Gatti, Gerardo Alberto
Ponce, Andrés Alberto
Saavedra Larralde, Natalia
Martinez, María J.
Zunino, María Paula
Zygadlo, Julio Alberto
author_role author
author2 Gatti, Gerardo Alberto
Ponce, Andrés Alberto
Saavedra Larralde, Natalia
Martinez, María J.
Zunino, María Paula
Zygadlo, Julio Alberto
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv CINNAMALDEHYDE-RELATED STRUCTURES
INSECTICIDAL PROPERTY
QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP
REPELLENT EFFECT
SITOPHILUS ZEAMAIS
topic CINNAMALDEHYDE-RELATED STRUCTURES
INSECTICIDAL PROPERTY
QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP
REPELLENT EFFECT
SITOPHILUS ZEAMAIS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.7
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Insecticidal activity and repellent effects on adults of Sitophiluszeamais of 12 cinnamaldehyde-related compounds was evaluated by contacttoxicity bioassays and a two-choice olfactometer, respectively. To determinenon-toxicity in mammals, additionally, body weight, serum biochemical profiles,liver weight, physiological parameters, sperm motility and histopathological data were obtained as complementary information in C57BL/6 mice, treated with the best natural compound. RESULTS: Based on 24h LC95 and LC50 values, alpha-methyl-cinnamaldehydeand cinnamaldehyde, respectively, exhibited better insecticidal activity than the other compounds. The best repellent effect was observed with alpha-bromocinnamaldehyde, which even repelled at the lowest concentration studied (0.28µM). The evaluation of a quantitative structure-activity relationship showed a linear relationship between the LC50 values for adult weevil toxicity and dipolo with Q (difference between orbital electronegativity carbon 1 and orbital electronegativity carbon 3 of the molecule) values in cinnamaldehyde-related compounds. In addition, the polar surface and Log P descriptors also revealed a linear relationship with the S. zeamais repellent effect for cinnamaldehyde analogues. Besides, cinnamaldehyde did not show toxicity in the parameters evaluated in mice.CONCLUSION: From the phenylpropanoid components studied, the naturalcompound which had the best insecticidal and repellent activity against S.zeamais was cinnamaldehyde and presented no mammalian toxicity.
Fil: Zaio, Yésica Paola. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto de Ciencias y Tecnología de los Alimentos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Gatti, Gerardo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina. Fundación Para Progreso Medicina-hospital Privado; Argentina
Fil: Ponce, Andrés Alberto. Fundación Para El Progreso de la Medicina; Argentina
Fil: Saavedra Larralde, Natalia. Universidad Nacional de Córdoba. Facultad de Medicina. Departamento de Fisiología Humana y Física Biomedica; Argentina
Fil: Martinez, María J.. Universidad Nacional de Córdoba. Facultad de Medicina; Argentina
Fil: Zunino, María Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Zygadlo, Julio Alberto. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto de Ciencias y Tecnología de los Alimentos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
description Insecticidal activity and repellent effects on adults of Sitophiluszeamais of 12 cinnamaldehyde-related compounds was evaluated by contacttoxicity bioassays and a two-choice olfactometer, respectively. To determinenon-toxicity in mammals, additionally, body weight, serum biochemical profiles,liver weight, physiological parameters, sperm motility and histopathological data were obtained as complementary information in C57BL/6 mice, treated with the best natural compound. RESULTS: Based on 24h LC95 and LC50 values, alpha-methyl-cinnamaldehydeand cinnamaldehyde, respectively, exhibited better insecticidal activity than the other compounds. The best repellent effect was observed with alpha-bromocinnamaldehyde, which even repelled at the lowest concentration studied (0.28µM). The evaluation of a quantitative structure-activity relationship showed a linear relationship between the LC50 values for adult weevil toxicity and dipolo with Q (difference between orbital electronegativity carbon 1 and orbital electronegativity carbon 3 of the molecule) values in cinnamaldehyde-related compounds. In addition, the polar surface and Log P descriptors also revealed a linear relationship with the S. zeamais repellent effect for cinnamaldehyde analogues. Besides, cinnamaldehyde did not show toxicity in the parameters evaluated in mice.CONCLUSION: From the phenylpropanoid components studied, the naturalcompound which had the best insecticidal and repellent activity against S.zeamais was cinnamaldehyde and presented no mammalian toxicity.
publishDate 2018
dc.date.none.fl_str_mv 2018-12
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/11336/86567
Zaio, Yésica Paola; Gatti, Gerardo Alberto; Ponce, Andrés Alberto; Saavedra Larralde, Natalia; Martinez, María J.; et al.; Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship; John Wiley & Sons Ltd; Journal of the Science of Food and Agriculture; 98; 15; 12-2018; 5822-5831
0022-5142
1097-0010
CONICET Digital
CONICET
url http://hdl.handle.net/11336/86567
identifier_str_mv Zaio, Yésica Paola; Gatti, Gerardo Alberto; Ponce, Andrés Alberto; Saavedra Larralde, Natalia; Martinez, María J.; et al.; Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship; John Wiley & Sons Ltd; Journal of the Science of Food and Agriculture; 98; 15; 12-2018; 5822-5831
0022-5142
1097-0010
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://doi.wiley.com/10.1002/jsfa.9132
info:eu-repo/semantics/altIdentifier/doi/10.1002/jsfa.9132
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1002/jsfa.9132
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
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
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