title: Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)+-pulegone and menthone.
abstract: 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 [LC(50)=0.5 mg/dm(3); 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 (LC(50)=6.2 mg/dm(3)), menthone (LC(50)=1.9 mg/dm(3)), (4R)(+)-pulegone (LC(50)=1.7 mg/dm(3)) and a new component, menthofuran (LC(50)=0.3 mg/dm(3)), 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.
authors.affiliation: Laboratorio de Química Fina y Productos Naturales, Universidad Católica de Córdoba, Córdoba, Argentina.
authors.forename: Yanina Estefanía
authors.initials: YE
authors.lastname: Rossi
authors.forename: Lilián
authors.initials: L
authors.lastname: Canavoso
authors.forename: Sara María
authors.initials: SM
authors.lastname: Palacios
mesh_terms: D000818:Animals; D001681:Biological Assay; D002470:Cell Survival / Q000187:drug effects; D000081005:Cyclohexane Monoterpenes; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics / Q000378:metabolism; D004357:Drug Synergism; D006793:Houseflies / Q000187:drug effects* / Q000201:enzymology / Q000235:genetics; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D019686:Lamiaceae / Q000737:chemistry*; D007928:Lethal Dose 50; D008610:Menthol / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D039821:Monoterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D009822:Oils, Volatile / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D010938:Plant Oils / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000081005:Cyclohexane Monoterpenes; D007306:Insecticides; D039821:Monoterpenes; D009822:Oils, Volatile; D010936:Plant Extracts; D010938:Plant Oils; D013729:Terpenes; D008610:Menthol; C054487:menthofuran; C039648:pulegone; D003577:Cytochrome P-450 Enzyme System; C019466:menthone