Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
- Autores
- Ruiz Hidalgo, José; Parellada, Eduardo Alberto; Bardon, Alicia del Valle; Vera, Nancy Roxana; Neske, Adriana
- Año de publicación
- 2018
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Background: Annonaceous acetogenins enclose a large number of biological activities, among which the insecticidal stands out. Methods: We report herein the biocide effects of natural acetogenins from Annona squamosa , A. muricata and A. montana seeds: annonacin, cis -annonacin, cis -annonacin-10- one, asimicin, rolliniastatin-2, cherimolin-1, cherimolin-2, almuñequin, and two β -OH acetogenins: laherradurin and itrabin on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). Also, some acetylated and methoxy methylated ACG derivatives were synthesized and evaluated: annonacin (3 OAc), annonacin (4 OAc), asimicin (3 OAc), rolliniastatin-2 (3 OAc), rolliniastatin-2 (MOM), laherradurin (3 OAc) and itrabin (3 OAc). Results: The natural acetogenin rolliniastatin-2 (100 μg∙g−1 of diet) produced the most important toxic action causing 100% mortality of early instar larvae. Derivatization of ACG yielded compounds that produced nutritional alterations. The incorporation of rolliniastatin-2 (3 OAc) and rolliniastatin-2 (3 MOM) (100 μg∙g−1) into the artificial diet of Spodoptera frugiperda displayed the strongest antifeedant effects causing marked decreasings in larval growth and adult lethal malformations. Conclusion: Natural acetogenins are promising metabolites for insect control. Derivatization of these compounds reduces their toxicity to early instar larvae.
Fil: Ruiz Hidalgo, José. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Parellada, Eduardo Alberto. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Vera, Nancy Roxana. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Farmacia; Argentina
Fil: Neske, Adriana. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina - Materia
-
ANNONACEOUS ACETOGENINS
BIOCIDES
SPODOPTERA FRUGIPERDA
BIOCIDES - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/184728
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CONICET Digital (CONICET) |
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Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)Ruiz Hidalgo, JoséParellada, Eduardo AlbertoBardon, Alicia del ValleVera, Nancy RoxanaNeske, AdrianaANNONACEOUS ACETOGENINSBIOCIDESSPODOPTERA FRUGIPERDABIOCIDEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Background: Annonaceous acetogenins enclose a large number of biological activities, among which the insecticidal stands out. Methods: We report herein the biocide effects of natural acetogenins from Annona squamosa , A. muricata and A. montana seeds: annonacin, cis -annonacin, cis -annonacin-10- one, asimicin, rolliniastatin-2, cherimolin-1, cherimolin-2, almuñequin, and two β -OH acetogenins: laherradurin and itrabin on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). Also, some acetylated and methoxy methylated ACG derivatives were synthesized and evaluated: annonacin (3 OAc), annonacin (4 OAc), asimicin (3 OAc), rolliniastatin-2 (3 OAc), rolliniastatin-2 (MOM), laherradurin (3 OAc) and itrabin (3 OAc). Results: The natural acetogenin rolliniastatin-2 (100 μg∙g−1 of diet) produced the most important toxic action causing 100% mortality of early instar larvae. Derivatization of ACG yielded compounds that produced nutritional alterations. The incorporation of rolliniastatin-2 (3 OAc) and rolliniastatin-2 (3 MOM) (100 μg∙g−1) into the artificial diet of Spodoptera frugiperda displayed the strongest antifeedant effects causing marked decreasings in larval growth and adult lethal malformations. Conclusion: Natural acetogenins are promising metabolites for insect control. Derivatization of these compounds reduces their toxicity to early instar larvae.Fil: Ruiz Hidalgo, José. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Parellada, Eduardo Alberto. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Vera, Nancy Roxana. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Farmacia; ArgentinaFil: Neske, Adriana. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaScientific Research Publishing2018-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/184728Ruiz Hidalgo, José; Parellada, Eduardo Alberto; Bardon, Alicia del Valle; Vera, Nancy Roxana; Neske, Adriana; Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae); Scientific Research Publishing; Journal of Agricultural Chemistry and Environment; 7; 3; 8-2018; 105-1162325-7458CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.scirp.org/journal/paperinformation.aspx?paperid=85873info:eu-repo/semantics/altIdentifier/doi/10.4236/jacen.2018.73010info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:45:30Zoai:ri.conicet.gov.ar:11336/184728instacron: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:34982025-09-03 09:45:30.457CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae) |
title |
Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae) |
spellingShingle |
Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae) Ruiz Hidalgo, José ANNONACEOUS ACETOGENINS BIOCIDES SPODOPTERA FRUGIPERDA BIOCIDES |
title_short |
Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae) |
title_full |
Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae) |
title_fullStr |
Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae) |
title_full_unstemmed |
Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae) |
title_sort |
Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae) |
dc.creator.none.fl_str_mv |
Ruiz Hidalgo, José Parellada, Eduardo Alberto Bardon, Alicia del Valle Vera, Nancy Roxana Neske, Adriana |
author |
Ruiz Hidalgo, José |
author_facet |
Ruiz Hidalgo, José Parellada, Eduardo Alberto Bardon, Alicia del Valle Vera, Nancy Roxana Neske, Adriana |
author_role |
author |
author2 |
Parellada, Eduardo Alberto Bardon, Alicia del Valle Vera, Nancy Roxana Neske, Adriana |
author2_role |
author author author author |
dc.subject.none.fl_str_mv |
ANNONACEOUS ACETOGENINS BIOCIDES SPODOPTERA FRUGIPERDA BIOCIDES |
topic |
ANNONACEOUS ACETOGENINS BIOCIDES SPODOPTERA FRUGIPERDA BIOCIDES |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
Background: Annonaceous acetogenins enclose a large number of biological activities, among which the insecticidal stands out. Methods: We report herein the biocide effects of natural acetogenins from Annona squamosa , A. muricata and A. montana seeds: annonacin, cis -annonacin, cis -annonacin-10- one, asimicin, rolliniastatin-2, cherimolin-1, cherimolin-2, almuñequin, and two β -OH acetogenins: laherradurin and itrabin on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). Also, some acetylated and methoxy methylated ACG derivatives were synthesized and evaluated: annonacin (3 OAc), annonacin (4 OAc), asimicin (3 OAc), rolliniastatin-2 (3 OAc), rolliniastatin-2 (MOM), laherradurin (3 OAc) and itrabin (3 OAc). Results: The natural acetogenin rolliniastatin-2 (100 μg∙g−1 of diet) produced the most important toxic action causing 100% mortality of early instar larvae. Derivatization of ACG yielded compounds that produced nutritional alterations. The incorporation of rolliniastatin-2 (3 OAc) and rolliniastatin-2 (3 MOM) (100 μg∙g−1) into the artificial diet of Spodoptera frugiperda displayed the strongest antifeedant effects causing marked decreasings in larval growth and adult lethal malformations. Conclusion: Natural acetogenins are promising metabolites for insect control. Derivatization of these compounds reduces their toxicity to early instar larvae. Fil: Ruiz Hidalgo, José. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina Fil: Parellada, Eduardo Alberto. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina Fil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina Fil: Vera, Nancy Roxana. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Farmacia; Argentina Fil: Neske, Adriana. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina |
description |
Background: Annonaceous acetogenins enclose a large number of biological activities, among which the insecticidal stands out. Methods: We report herein the biocide effects of natural acetogenins from Annona squamosa , A. muricata and A. montana seeds: annonacin, cis -annonacin, cis -annonacin-10- one, asimicin, rolliniastatin-2, cherimolin-1, cherimolin-2, almuñequin, and two β -OH acetogenins: laherradurin and itrabin on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). Also, some acetylated and methoxy methylated ACG derivatives were synthesized and evaluated: annonacin (3 OAc), annonacin (4 OAc), asimicin (3 OAc), rolliniastatin-2 (3 OAc), rolliniastatin-2 (MOM), laherradurin (3 OAc) and itrabin (3 OAc). Results: The natural acetogenin rolliniastatin-2 (100 μg∙g−1 of diet) produced the most important toxic action causing 100% mortality of early instar larvae. Derivatization of ACG yielded compounds that produced nutritional alterations. The incorporation of rolliniastatin-2 (3 OAc) and rolliniastatin-2 (3 MOM) (100 μg∙g−1) into the artificial diet of Spodoptera frugiperda displayed the strongest antifeedant effects causing marked decreasings in larval growth and adult lethal malformations. Conclusion: Natural acetogenins are promising metabolites for insect control. Derivatization of these compounds reduces their toxicity to early instar larvae. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-08 |
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/11336/184728 Ruiz Hidalgo, José; Parellada, Eduardo Alberto; Bardon, Alicia del Valle; Vera, Nancy Roxana; Neske, Adriana; Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae); Scientific Research Publishing; Journal of Agricultural Chemistry and Environment; 7; 3; 8-2018; 105-116 2325-7458 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/184728 |
identifier_str_mv |
Ruiz Hidalgo, José; Parellada, Eduardo Alberto; Bardon, Alicia del Valle; Vera, Nancy Roxana; Neske, Adriana; Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae); Scientific Research Publishing; Journal of Agricultural Chemistry and Environment; 7; 3; 8-2018; 105-116 2325-7458 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/https://www.scirp.org/journal/paperinformation.aspx?paperid=85873 info:eu-repo/semantics/altIdentifier/doi/10.4236/jacen.2018.73010 |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Scientific Research Publishing |
publisher.none.fl_str_mv |
Scientific Research Publishing |
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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1842268735384059904 |
score |
13.13397 |