1,8-Cineole (Eucalyptol), a mosquito feeding and ovipositional repellent from volatile oil ofHemizonia fitchii (Asteraceae)

Klocke, James A.; Darlington, Mark V.; Balandrin, Manuel F.

doi:10.1007/bf01012562

Cited by 138 publications

(73 citation statements)

References 16 publications

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“…The DEET-sensitive ORN was also stimulated in a dose-dependent manner by terpenoid compounds, such as thujone, eucalyptol, and linalool ( Fig. 2), which have already been reported as repellents (13)(14)(15).…”

Section: Resultsmentioning

confidence: 90%

Mosquitoes smell and avoid the insect repellent DEET

Syed

Leal

2008

Proc. Natl. Acad. Sci. U.S.A.

286

231

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The insect repellent DEET is effective against a variety of medically important pests, but its mode of action still draws considerable debate. The widely accepted hypothesis that DEET interferes with the detection of lactic acid has been challenged by demonstrated DEETinduced repellency in the absence of lactic acid. The most recent hypothesis suggests that DEET masks or jams the olfactory system by attenuating electrophysiological responses to 1-octen-3-ol. Our research shows that mosquitoes smell DEET directly and avoid it. We performed single-unit recordings from all functional ORNs on the antenna and maxillary palps of Culex quinquefasciatus and found an ORN in a short trichoid sensillum responding to DEET in a dosedependent manner. The same ORN responded with higher sensitivity to terpenoid compounds. SPME and GC analysis showed that odorants were trapped in conventional stimulus cartridges upon addition of a DEET-impregnated filter paper strip thus leading to the observed reduced electrophysiological responses, as reported elsewhere. With a new stimulus delivery method releasing equal amounts of 1-octen-3-ol alone or in combination with DEET we found no difference in neuronal responses. When applied to human skin, DEET altered the chemical profile of emanations by a ''fixative'' effect that may also contribute to repellency. However, the main mode of action is the direct detection of DEET as indicated by the evidence that mosquitoes are endowed with DEET-detecting ORNs and corroborated by behavioral bioassays. In a sugar-feeding assay, both female and male mosquitoes avoided DEET. In addition, mosquitoes responding only to physical stimuli avoided DEET.DEET mode of action ͉ DEET-detecting neuron ͉ fixative effect of DEET ͉ mosquito olfaction ͉ surface-landing bioassay T he insect repellent DEET, N,N-diethyl-3-methylbenzamide, has been used for Ͼ50 years, with 200 million people using it worldwide to reduce their risk of vector-borne diseases (1) but its mode of action has yet to be elucidated. The report that DEET modulates the physiological response of lactic acid-sensitive olfactory receptor neurons (ORNs) in the antennae of the yellow fever mosquito, Aedes aegypti (2), led to the hypothesis that DEET may interfere with and inhibit the response of the olfactory system to a normally attractive chemical signal (3). This notion of ''jamming'' the olfactory system has been substantiated, on the one hand, by behavioral observations indicating that lactic acid per se is a mosquito attractant and suggesting that DEET inhibits attraction to lactic acid (4, 5) and by the recent report on DEET attenuation of mosquito response to 1-octen-3-ol (6). However, repellency solely by inhibition of lactic acid detection was challenged by indoor (4) and field experiments (7) demonstrating the repellent effect of DEET with carbon dioxide as the only attractant. Intrigued by this controversy and puzzled by the dichotomy between sensory physiology and behavioral observations, we undertook a multidisciplinary approach aimed at ...

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Section: Resultsmentioning

confidence: 90%

Mosquitoes smell and avoid the insect repellent DEET

Syed

Leal

2008

Proc. Natl. Acad. Sci. U.S.A.

286

231

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“…O óleo dos frutos da C. xanthocarpa, além de conter mais hidrocarbonetos monoterpênicos do que os encontrados por Vallilo et al (2006), nos frutos da C. adamantium, apresentou como componentes majoritários, α-pineno (15,0%), o-cimeno (10,8%) e β-pineno (10,5%), enquanto nos frutos da adamantium, destacam-se, como componentes principais, o α-pineno (10,6%), o limoneno (10,1%) e o β-(z)-ocimeno (9,2%) ( VALLILO et al, 2006). Segundo Chagas et al (2002), a maioria dos monoterpenos é pouco tóxica para mamíferos (KLOCKE; DARLINGTON; BALANDRIN, 1987;OMS, 1990). Alguns são considerados como alternativas potenciais aos inseticidas comerciais sinté-ticos, já que são reconhecidos como seguros pela United States Food and Drug Administration sendo, portanto, largamente utilizados em condimentos artificiais, perfumes, formulações de expectorantes, descongestionantes, analgésicos externos e anti-sépticos (KLOCKE; DARLINGTON; BALANDRIN, 1987;WINDHOLZ et al, 1998 No óleo da xanthocarpa também foi detectada a presença de limoneno, contribuindo em apenas 5,1% da composição do óleo total, enquanto que o β-(z)-ocimeno não foi detectado nessa espécie.…”

Section: Resultsunclassified

“…Segundo Chagas et al (2002), a maioria dos monoterpenos é pouco tóxica para mamíferos (KLOCKE; DARLINGTON; BALANDRIN, 1987;OMS, 1990). Alguns são considerados como alternativas potenciais aos inseticidas comerciais sinté-ticos, já que são reconhecidos como seguros pela United States Food and Drug Administration sendo, portanto, largamente utilizados em condimentos artificiais, perfumes, formulações de expectorantes, descongestionantes, analgésicos externos e anti-sépticos (KLOCKE; DARLINGTON; BALANDRIN, 1987;WINDHOLZ et al, 1998 No óleo da xanthocarpa também foi detectada a presença de limoneno, contribuindo em apenas 5,1% da composição do óleo total, enquanto que o β-(z)-ocimeno não foi detectado nessa espécie. A composição dos óleos dos frutos das duas plantas apresentaram somente nove substâncias em comum, com concentrações diferentes: α-pineno, β-5.…”

Section: Resultsunclassified

Composição química dos frutos de Campomanesia xanthocarpa Berg-Myrtaceae

Vallilo¹,

Moreno²,

Oliveira³

et al. 2008

Ciênc. Tecnol. Aliment.

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“…Monoterpenoids are used widely as fragrance and flavoring ingredients (Croteau 1980) and in over-the-counter formulations of expectorants, decongestants, external analgesics, and antiseptics (Klocke 1987). Characteristics of these simple compounds that make them attractive for development as environmentally sound arthropod control agents include their selective arthropod toxicity, low mammalian toxicity, and biodegradability.…”

Section: Methodsmentioning

confidence: 99%

Toxicity of Seven Monoterpenoids to Tracheal Mites (Acari: Tarsonemidae) and Their Honey Bee (Hymenoptera: Apidae) Hosts When Applied as Fumigants

Ellis

Baxendale

1997

Journal of Economic Entomology

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Laboratory bioassays were conducted to characterize the acute toxicity of 7 monoterpenoids to tracheal mites, Acarapis woodi (Rennie), and their honey bee, Apis mellifera L., hosts. Citral, thymol, carvacrol, a-terpineol, pulegone, d-limonene, and menthol were applied as fumigants to mite-infested honey bees. Thymol and menthol were the most toxic compounds to honey bees, and a-terpineol was the least toxic. Menthol, citral, thymol, and carvacrol were more toxic to tracheal mites than to honey bees. Pulegone, d-limonene, and a-terpineol were more toxic to honey bees than to tracheal mites. Menthol was 18.9 times more toxic to tracheal mites than to honey bees at the LC so concentrations; however, as the concentration increased, bee mortality increased more rapidly than mite mortality, and menthol was only 5.7 times more toxic at the LCgo concentrations. Probit regressions for bee and mite mortality were parallel for citral and thymol. Citral and thymol were 2.9 (2.5-3.3) and 2.0 (1.0-3.6) times more toxic to tracheal mites, respectively, at all concentrations estimated.

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1,8-Cineole (Eucalyptol), a mosquito feeding and ovipositional repellent from volatile oil ofHemizonia fitchii (Asteraceae)

Cited by 138 publications

References 16 publications

Mosquitoes smell and avoid the insect repellent DEET

Mosquitoes smell and avoid the insect repellent DEET

Composição química dos frutos de Campomanesia xanthocarpa Berg-Myrtaceae

Toxicity of Seven Monoterpenoids to Tracheal Mites (Acari: Tarsonemidae) and Their Honey Bee (Hymenoptera: Apidae) Hosts When Applied as Fumigants

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