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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/86567
Ver los metadatos del registro completo
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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 Técnicas2025-09-29T09:35:57Zoai: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:34982025-09-29 09:35:58.082CONICET 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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1844613124632608768 |
score |
13.070432 |