Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)

Autores
Ruiz Hidalgo, José; Parellada, Eduardo Alberto; Bardon, Alicia del Valle; Neske, Adriana Neske
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 frugiperdadisplayed 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina
Fil: Parellada, Eduardo Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Bardon, Alicia del Valle. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. 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
Fil: Neske, Adriana Neske. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina
Materia
ANNONACEOUS
ACETOGENINS
BIOCIDES
SPODOPTERA
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:11336/81070
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/81070
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)Ruiz Hidalgo, JoséParellada, Eduardo AlbertoBardon, Alicia del ValleNeske, Adriana NeskeANNONACEOUSACETOGENINSBIOCIDESSPODOPTERAhttps://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 frugiperdadisplayed 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; ArgentinaFil: Parellada, Eduardo Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Bardon, Alicia del Valle. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. 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; ArgentinaFil: Neske, Adriana Neske. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; ArgentinaSCIRP2018-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/81070Ruiz Hidalgo, José; Parellada, Eduardo Alberto; Bardon, Alicia del Valle; Neske, Adriana Neske; Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae); SCIRP; Journal of Agricultural Chemistry and Environment; 7; 3; 7-2018; 105-1162325-74582325-744XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/ 10.4236/jacen.2018.73010info:eu-repo/semantics/altIdentifier/url/http://www.scirp.org/journal/paperinformation.aspx?paperid=85873info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:09:58Zoai:ri.conicet.gov.ar:11336/81070instacron: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 10:09:59.117CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
title Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
spellingShingle Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
Ruiz Hidalgo, José
ANNONACEOUS
ACETOGENINS
BIOCIDES
SPODOPTERA
title_short Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
title_full Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
title_fullStr Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
title_full_unstemmed Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
title_sort Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae)
dc.creator.none.fl_str_mv Ruiz Hidalgo, José
Parellada, Eduardo Alberto
Bardon, Alicia del Valle
Neske, Adriana Neske
author Ruiz Hidalgo, José
author_facet Ruiz Hidalgo, José
Parellada, Eduardo Alberto
Bardon, Alicia del Valle
Neske, Adriana Neske
author_role author
author2 Parellada, Eduardo Alberto
Bardon, Alicia del Valle
Neske, Adriana Neske
author2_role author
author
author
dc.subject.none.fl_str_mv ANNONACEOUS
ACETOGENINS
BIOCIDES
SPODOPTERA
topic ANNONACEOUS
ACETOGENINS
BIOCIDES
SPODOPTERA
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 frugiperdadisplayed 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. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina
Fil: Parellada, Eduardo Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Bardon, Alicia del Valle. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. 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
Fil: Neske, Adriana Neske. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; 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 frugiperdadisplayed 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 2018-07
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/11336/81070
Ruiz Hidalgo, José; Parellada, Eduardo Alberto; Bardon, Alicia del Valle; Neske, Adriana Neske; Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae); SCIRP; Journal of Agricultural Chemistry and Environment; 7; 3; 7-2018; 105-116
2325-7458
2325-744X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/81070
identifier_str_mv Ruiz Hidalgo, José; Parellada, Eduardo Alberto; Bardon, Alicia del Valle; Neske, Adriana Neske; Annonaceous Acetogenins with insecticidal effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae); SCIRP; Journal of Agricultural Chemistry and Environment; 7; 3; 7-2018; 105-116
2325-7458
2325-744X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/ 10.4236/jacen.2018.73010
info:eu-repo/semantics/altIdentifier/url/http://www.scirp.org/journal/paperinformation.aspx?paperid=85873
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
dc.publisher.none.fl_str_mv SCIRP
publisher.none.fl_str_mv SCIRP
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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score 13.070432

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