Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone

Autores
Rossi, Yanina Estefanía; Canavoso, Lilian Etelvina; Palacios, Sara Maria
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Intense applications of synthetic insecticides for the control of adult Musca domestica have led to the insects developing resistance to most of them. In consequence, there is interest in new active ingredients as alternatives to conventional insecticides. Essential oils (EO) are potential tools for controlling M. domestica because of their effectiveness and their minimal environmental effects. In a fumigant assay, M. domestica adults treated with Minthostachys verticillata EO [LC50 = 0.5 mg/dm3; majority components by SPME-GC: (4R)(+)-pulegone (67.5%), menthone (22.3%) and (4R)(+)-limonene (3.8%)], died within 15 min or less. The terpenes absorbed by the flies and their metabolites, analyzed using SPME fiber, were (4R)(+)-limonene (LC50 = 6.2 mg/dm3), menthone (LC 50 = 1.9 mg/dm3), (4R)(+)-pulegone (LC50 = 1.7 mg/dm3) and a new component, menthofuran (LC50 = 0.3 mg/dm3), in a relative proportion of 12.4, 6.5, 35.9 and 44.2% respectively. Menthofuran was formed by oxidation of either (4R)(+)-pulegone or menthone mediated by cytochrome P450, as demonstrated by a fumigation assay on flies previously treated with piperonyl butoxide, a P450 inhibitor, which showed a decrease in toxicity of the EO, (4R)(+)-pulegone and of menthone, supporting the participation of the P450 oxidizing system in the formation of menthofuran. The enzymatic reaction of isolated fly microsomes with the EO or the (4R)(+)-pulegone produced menthofuran in both cases. Contrary to expectations, the insect detoxification system contributed to enhance the toxicity of the M. verticillata EO. Consequently, resistant strains overexpressing P450 genes will be more susceptible to either M. verticillata EO or (4R)(+)-pulegone and menthone.
Fil: Rossi, Yanina Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Centro de Investigaciones y Transferencia de Villa María. Universidad Nacional de Villa María. Centro de Investigaciones y Transferencia de Villa María; Argentina
Fil: Canavoso, Lilian Etelvina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina
Fil: Palacios, Sara Maria. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
(4R)(+)-PULEGONE
CYTOCHROME P450
ESSENTIAL OIL
MINTHOSTACHYS VERTICILLATA
MUSCA DOMESTICA
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:11336/59824
Acceder
id CONICETDig_8ad4d1b6a64b55fcda412151d124b8c2
oai_identifier_str oai:ri.conicet.gov.ar:11336/59824
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthoneRossi, Yanina EstefaníaCanavoso, Lilian EtelvinaPalacios, Sara Maria(4R)(+)-PULEGONECYTOCHROME P450ESSENTIAL OILMINTHOSTACHYS VERTICILLATAMUSCA DOMESTICAhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Intense applications of synthetic insecticides for the control of adult Musca domestica have led to the insects developing resistance to most of them. In consequence, there is interest in new active ingredients as alternatives to conventional insecticides. Essential oils (EO) are potential tools for controlling M. domestica because of their effectiveness and their minimal environmental effects. In a fumigant assay, M. domestica adults treated with Minthostachys verticillata EO [LC50 = 0.5 mg/dm3; majority components by SPME-GC: (4R)(+)-pulegone (67.5%), menthone (22.3%) and (4R)(+)-limonene (3.8%)], died within 15 min or less. The terpenes absorbed by the flies and their metabolites, analyzed using SPME fiber, were (4R)(+)-limonene (LC50 = 6.2 mg/dm3), menthone (LC 50 = 1.9 mg/dm3), (4R)(+)-pulegone (LC50 = 1.7 mg/dm3) and a new component, menthofuran (LC50 = 0.3 mg/dm3), in a relative proportion of 12.4, 6.5, 35.9 and 44.2% respectively. Menthofuran was formed by oxidation of either (4R)(+)-pulegone or menthone mediated by cytochrome P450, as demonstrated by a fumigation assay on flies previously treated with piperonyl butoxide, a P450 inhibitor, which showed a decrease in toxicity of the EO, (4R)(+)-pulegone and of menthone, supporting the participation of the P450 oxidizing system in the formation of menthofuran. The enzymatic reaction of isolated fly microsomes with the EO or the (4R)(+)-pulegone produced menthofuran in both cases. Contrary to expectations, the insect detoxification system contributed to enhance the toxicity of the M. verticillata EO. Consequently, resistant strains overexpressing P450 genes will be more susceptible to either M. verticillata EO or (4R)(+)-pulegone and menthone.Fil: Rossi, Yanina Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Centro de Investigaciones y Transferencia de Villa María. Universidad Nacional de Villa María. Centro de Investigaciones y Transferencia de Villa María; ArgentinaFil: Canavoso, Lilian Etelvina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; ArgentinaFil: Palacios, Sara Maria. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaElsevier Science2012-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/59824Rossi, Yanina Estefanía; Canavoso, Lilian Etelvina; Palacios, Sara Maria; Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone; Elsevier Science; Fitoterapia; 83; 2; 3-2012; 336-3420367-326XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0367326X11002954info:eu-repo/semantics/altIdentifier/doi/10.1016/j.fitote.2011.11.019info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:07:51Zoai:ri.conicet.gov.ar:11336/59824instacron: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 10:07:51.949CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone
title Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone
spellingShingle Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone
Rossi, Yanina Estefanía
(4R)(+)-PULEGONE
CYTOCHROME P450
ESSENTIAL OIL
MINTHOSTACHYS VERTICILLATA
MUSCA DOMESTICA
title_short Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone
title_full Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone
title_fullStr Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone
title_full_unstemmed Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone
title_sort Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone
dc.creator.none.fl_str_mv Rossi, Yanina Estefanía
Canavoso, Lilian Etelvina
Palacios, Sara Maria
author Rossi, Yanina Estefanía
author_facet Rossi, Yanina Estefanía
Canavoso, Lilian Etelvina
Palacios, Sara Maria
author_role author
author2 Canavoso, Lilian Etelvina
Palacios, Sara Maria
author2_role author
author
dc.subject.none.fl_str_mv (4R)(+)-PULEGONE
CYTOCHROME P450
ESSENTIAL OIL
MINTHOSTACHYS VERTICILLATA
MUSCA DOMESTICA
topic (4R)(+)-PULEGONE
CYTOCHROME P450
ESSENTIAL OIL
MINTHOSTACHYS VERTICILLATA
MUSCA DOMESTICA
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Intense applications of synthetic insecticides for the control of adult Musca domestica have led to the insects developing resistance to most of them. In consequence, there is interest in new active ingredients as alternatives to conventional insecticides. Essential oils (EO) are potential tools for controlling M. domestica because of their effectiveness and their minimal environmental effects. In a fumigant assay, M. domestica adults treated with Minthostachys verticillata EO [LC50 = 0.5 mg/dm3; majority components by SPME-GC: (4R)(+)-pulegone (67.5%), menthone (22.3%) and (4R)(+)-limonene (3.8%)], died within 15 min or less. The terpenes absorbed by the flies and their metabolites, analyzed using SPME fiber, were (4R)(+)-limonene (LC50 = 6.2 mg/dm3), menthone (LC 50 = 1.9 mg/dm3), (4R)(+)-pulegone (LC50 = 1.7 mg/dm3) and a new component, menthofuran (LC50 = 0.3 mg/dm3), in a relative proportion of 12.4, 6.5, 35.9 and 44.2% respectively. Menthofuran was formed by oxidation of either (4R)(+)-pulegone or menthone mediated by cytochrome P450, as demonstrated by a fumigation assay on flies previously treated with piperonyl butoxide, a P450 inhibitor, which showed a decrease in toxicity of the EO, (4R)(+)-pulegone and of menthone, supporting the participation of the P450 oxidizing system in the formation of menthofuran. The enzymatic reaction of isolated fly microsomes with the EO or the (4R)(+)-pulegone produced menthofuran in both cases. Contrary to expectations, the insect detoxification system contributed to enhance the toxicity of the M. verticillata EO. Consequently, resistant strains overexpressing P450 genes will be more susceptible to either M. verticillata EO or (4R)(+)-pulegone and menthone.
Fil: Rossi, Yanina Estefanía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Centro de Investigaciones y Transferencia de Villa María. Universidad Nacional de Villa María. Centro de Investigaciones y Transferencia de Villa María; Argentina
Fil: Canavoso, Lilian Etelvina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina
Fil: Palacios, Sara Maria. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description Intense applications of synthetic insecticides for the control of adult Musca domestica have led to the insects developing resistance to most of them. In consequence, there is interest in new active ingredients as alternatives to conventional insecticides. Essential oils (EO) are potential tools for controlling M. domestica because of their effectiveness and their minimal environmental effects. In a fumigant assay, M. domestica adults treated with Minthostachys verticillata EO [LC50 = 0.5 mg/dm3; majority components by SPME-GC: (4R)(+)-pulegone (67.5%), menthone (22.3%) and (4R)(+)-limonene (3.8%)], died within 15 min or less. The terpenes absorbed by the flies and their metabolites, analyzed using SPME fiber, were (4R)(+)-limonene (LC50 = 6.2 mg/dm3), menthone (LC 50 = 1.9 mg/dm3), (4R)(+)-pulegone (LC50 = 1.7 mg/dm3) and a new component, menthofuran (LC50 = 0.3 mg/dm3), in a relative proportion of 12.4, 6.5, 35.9 and 44.2% respectively. Menthofuran was formed by oxidation of either (4R)(+)-pulegone or menthone mediated by cytochrome P450, as demonstrated by a fumigation assay on flies previously treated with piperonyl butoxide, a P450 inhibitor, which showed a decrease in toxicity of the EO, (4R)(+)-pulegone and of menthone, supporting the participation of the P450 oxidizing system in the formation of menthofuran. The enzymatic reaction of isolated fly microsomes with the EO or the (4R)(+)-pulegone produced menthofuran in both cases. Contrary to expectations, the insect detoxification system contributed to enhance the toxicity of the M. verticillata EO. Consequently, resistant strains overexpressing P450 genes will be more susceptible to either M. verticillata EO or (4R)(+)-pulegone and menthone.
publishDate 2012
dc.date.none.fl_str_mv 2012-03
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/11336/59824
Rossi, Yanina Estefanía; Canavoso, Lilian Etelvina; Palacios, Sara Maria; Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone; Elsevier Science; Fitoterapia; 83; 2; 3-2012; 336-342
0367-326X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/59824
identifier_str_mv Rossi, Yanina Estefanía; Canavoso, Lilian Etelvina; Palacios, Sara Maria; Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone; Elsevier Science; Fitoterapia; 83; 2; 3-2012; 336-342
0367-326X
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.sciencedirect.com/science/article/pii/S0367326X11002954
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.fitote.2011.11.019
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
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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_ 1844613943439392768
score 13.069144

Publicaciones similares