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1.
J Chem Ecol ; 2024 May 29.
Artigo em Inglês | MEDLINE | ID: mdl-38806939

RESUMO

Stable flies, Stomoxys calcitrans (L.), are blood-feeding ectoparasites of cattle. Host-seeking stable flies respond to various cattle host cues, but a potential role of cattle breath gases [carbon dioxide (CO2), methane (CH4)] and cattle breath volatiles (acetone, isoprene, 2-butanone, 2-propanol, propionic acid, 3-methyl butyric acid, phenol), alone or in combination, on host-seeking behavior of stable flies has not yet been comprehensively investigated. In laboratory and greenhouse experiments, we tested the hypotheses that (1) CO2 and CH4 interactively attract stable flies, (2) CO2 'gates' attraction of stable flies to CH4, and (3) breath volatiles on their own, or in combination with both CO2 and CH4, attract stable flies. In Y-tube olfactometer experiments, the blend of CH4 (0.5%) and CO2 (1%) in breathing air ('b-air') attracted significantly more female flies than CH4, or CO2, in b-air. The flies' responses to CH4 were contingent upon their prior or concurrent exposure to CO2. In two-choice experiments in a large greenhouse compartment, significantly more flies landed on the host-look-alike barrel that disseminated a blend of CO2 and CH4 in b-air (CO2/CH4/b-air) than on the barrel disseminating either b-air or CO2. Moreover, significantly more flies landed on the barrel that disseminated synthetic breath volatiles (SBVs) than on the barrel disseminating b-air. The blend of CO2/CH4/b-air and SBVs elicited more fly landings on barrels than CO2/CH4/b-air but not than SBVs. SBVs, possibly combined with both CH4 and CO2, could be developed as a lure to enhance trap captures of stable flies in livestock production facilities.

2.
J Chem Ecol ; 48(3): 302-311, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-34738201

RESUMO

Four species of Tetramorium pavement ants are known to guide foraging activities of nestmates via trail pheromones secreted from the poison gland of worker ants, but the trail pheromone of T. immigrans is unknown. Our objectives were to (1) determine whether poison gland extract of T. immigrans workers induces trail-following behavior of nestmates, (2) identify the trail pheromone, and (3) test whether synthetic trail pheromone induces trail-following behavior of workers. In laboratory no-choice bioassays, ants followed poison-gland-extract trails farther than they followed whole-body-extract trails or solvent-control trails. Gas chromatographic-electroantennographic detection (GC-EAD) analyses of poison gland extract revealed a single candidate pheromone component (CPC) that elicited responses from worker ant antennae. The CPC mass spectrum indicated, and an authentic standard confirmed, that the CPC was methyl 2-methoxy-6-methylbenzoate (MMMB). In further laboratory no-choice bioassays, ants followed poison-gland-extract trails (tested at 1 ant equivalent) and synthetic MMMB trails (tested at 0.35 ant equivalents) equally far, indicating that MMMB is the single-component trail pheromone of T. immigrans. Moreover, in laboratory two-choice bioassays, ants followed MMMB trails ~ 21-times farther than solvent-control trails. In field settings, when T. immigrans colonies were offered a choice between two paper strips treated with a synthetic MMMB trail or a solvent-control trail, each leading to an apple bait, the MMMB trails efficiently recruited nestmates to baits.


Assuntos
Formigas , Animais , Formigas/fisiologia , Comportamento Alimentar , Humanos , Feromônios/farmacologia , Feromônios/fisiologia
3.
J Chem Ecol ; 48(5-6): 491-501, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35895216

RESUMO

Synthetic sex pheromone lures are useful tools to monitor and control populations of adult click beetles (Coleoptera: Elateridae). However, sex pheromones for Agriotes click beetle species native to North America have yet to be identified. Here we report the identification and field testing of the sex pheromone of Agriotes ferrugineipennis. Headspace volatiles from female beetles were collected on Porapak Q, and aliquots of Porapak extract were analyzed by gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry. 7-Methyloctyl 7-methyloctanoate (7Me7Me) emitted by females was more abundant and elicited much stronger responses from male antennae than the aldehydes octanal and nonanal and the ketone 6,10,14-trimethyl-2-pentadecanone. In a field experiment, captures of A. ferrugineipennis males in traps baited with candidate pheromone components exceeded those of unbaited control traps, on average by nearly 1,200 times. Neither the ketone nor the aldehydes as lure constituents appeared to alter captures of males in 7Me7Me-baited traps. We conclude that 7Me7Me is the major, and possibly the only, sex attractant pheromone component of female A. ferrugineipennis.


Assuntos
Besouros , Atrativos Sexuais , Aldeídos/farmacologia , Animais , Besouros/fisiologia , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Cetonas/farmacologia , Masculino , Feromônios/química , Atrativos Sexuais/química , Atrativos Sexuais/farmacologia
4.
J Chem Ecol ; 47(7): 614-627, 2021 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-34224074

RESUMO

The polyphagous invasive brown marmorated stink bug, Halyomorpha halys, reportedly discriminates among phenological stages of host plants. To determine whether olfaction is involved in host plant stage discrimination, we selected (dwarf) sunflower, Helianthus annuus, as a model host plant species. When adult females of a still-air laboratory experiment were offered a choice of four potted sunflowers at distinct phenological stages (vegetative, pre-bloom, bloom, seeding), most females settled onto blooming plants but oviposited evenly on plants of all four stages. In moving-air two-choice olfactometer experiments, we then tested each plant stage versus filtered air and versus one another, for attraction of H. halys females. Blooming sunflowers performed best overall, but no one plant stage was most attractive in all experiments. Capturing and analyzing (by GC-MS) the headspace odorants of each plant stage revealed a marked increase of odorant abundance (e.g., monoterpenes) as plants transitioned from pre-bloom to bloom. Analyzing the headspace odorant blend of blooming sunflower by gas chromatographic-electroantennographic detection (GC-EAD) revealed 13 odorants that consistently elicited responses from female H. halys antennae. An 11-component synthetic blend of these odorants attracted H. halys females in laboratory olfactometer experiments. Furthermore, in field settings, the synthetic blend enhanced the attractiveness of synthetic H. halys pheromone as a trap lure, particularly in spring (April to mid-June). A simpler yet fully effective sunflower semiochemical blend could be developed and coupled with synthetic H. halys aggregation pheromones to improve monitoring efforts or could improve the efficacy of modified attract-and-kill control tactics for H. halys.


Assuntos
Comportamento Animal/efeitos dos fármacos , Helianthus/química , Heterópteros/fisiologia , Feromônios/farmacologia , Animais , Feminino , Flores/química , Flores/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Helianthus/metabolismo , Oviposição/efeitos dos fármacos , Feromônios/análise , Feromônios/química , Estações do Ano
5.
J Chem Ecol ; 47(2): 123-133, 2021 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-33606109

RESUMO

Wireworms, the larvae of click beetles (Coleoptera: Elateridae), are soil-dwelling insect pests inflicting major economic damage on many types of agricultural crops worldwide. The objective of this work was to identify the female-produced sex pheromones of the Pacific Coast wireworm, Limonius canus LeConte, and the sugarbeet wireworm, L. californicus (Mannerheim) (Coleoptera: Elateridae). Headspace volatiles from separate groups of female L. canus and L. californicus were collected on Porapak Q and analyzed by gas chromatography with electroantennographic detection (GC-EAD) and GC-mass spectrometry. GC-EAD recordings revealed strong responses from male L. canus and male L. californicus antennae to the same compound, which appeared below GC detection threshold. The structure of this candidate pheromone component was deduced from the results of micro-analytical treatments of extracts, retention index calculations on four GC columns, and by syntheses of more than 25 model compounds which were assessed for their GC retention characteristics and electrophysiological activity. The EAD-active compound was identified as (E)-4-ethyloct-4-enoic acid, which we name limoniic acid. In field experiments in British Columbia and Alberta, Canada, traps baited with synthetic limoniic acid captured large numbers of male Limonius click beetles, whereas unbaited control traps captured few. Compared to traps baited with the analogue, (E)-5-ethyloct-4-enoic acid, traps baited with limoniic acid captured 9-times more male L. californicus, and 6.5-times more male western field wireworms, L. infuscatus Motschulsky, but 2.3-times fewer male L. canus. Limoniic acid can now be developed for detection, monitoring and possibly control of L. californicus, L. infuscatus and L. canus populations.


Assuntos
Besouros/química , Atrativos Sexuais/química , Animais , Besouros/fisiologia , Feminino , Masculino , Atrativos Sexuais/fisiologia
6.
J Chem Ecol ; 46(3): 361, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-32124137

RESUMO

The original version of this article unfortunately contained a mistake.

7.
J Chem Ecol ; 45(11-12): 901-913, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31773376

RESUMO

Trail pheromones deposited by ants lead nestmates to food sources. Based on previous evidence that the trail pheromone of the carpenter ant Camponotus modoc originates from the hindgut, our objective in this study was to identify the key component(s) of the pheromone. We collected C. modoc colonies from conifer forests and maintained them in an outdoor enclosure near our laboratory for chemical analyses and behavioral experiments. In gas chromatographic-electroantennographic detection and gas chromatography-mass spectrometric analyses of worker ant hindgut extracts, we identified five candidate components: 2,4-dimethylhexanoic acid, 2,4-dimethyl-5-hexanolide, pentadecane, dodecanoic acid and 3,4-dihydro-8-hydroxy-3,5,7-trimethylisocoumarin. In a series of trail-following experiments, ants followed trails of synthetic 2,4-dimethyl-5-hexanolide, a blend of the five compounds, and hindgut extract over similar distances, indicating that the hexanolide accounted for the entire behavioral activity of the hindgut extract. The hexanolide not only mediated orientation of C. modoc foragers on trails, it also attracted them over distance, indicating a dual function. Further analyses and bioassays with racemic and stereoselectively synthesized hexanolides revealed that the ants produce, and respond to, the (2S,4R,5S)-stereoisomer. The same stereoisomer is a trail pheromone component in several Camponotus congeners, indicating significant overlap in their respective trail pheromone communication systems.


Assuntos
Misturas Complexas/análise , Feromônios/análise , Alcanos/análise , Animais , Formigas , Comportamento Animal , Técnicas Biossensoriais/métodos , Caproatos/análise , Cumarínicos/análise , Glândulas Exócrinas/metabolismo , Cromatografia Gasosa-Espectrometria de Massas/métodos , Intestinos/química , Ácidos Láuricos/análise , Estereoisomerismo
8.
J Chem Ecol ; 45(1): 18-27, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30411204

RESUMO

Recently, it was reported (i) that the sex pheromone blend of male house mice, Mus musculus, comprises not only volatile components (3,4-dehydro-exo-brevicomin; 2-sec-butyl-4,5-dihydrothiazole) but also a component of low volatility (the sex steroid testosterone), and (ii) that the sex steroids progesterone and estradiol are sex pheromone components of female house mice. Here we tested the hypothesis that the sex attractant pheromone blend of female mice, analogous to that of male mice, also comprises volatile pheromone components. Analyzing by GC-MS the head space volatiles of bedding soiled with urine and feces of laboratory-kept females and males revealed three candidate pheromone components (CPCs) that were adult female-specific: butyric acid, 2-methyl butyric acid and 4-heptanone. In a two-choice laboratory experiment, adult males spent significantly more time in the treatment chamber baited with both the synthetic steroids (progesterone, estradiol) and the synthetic CPCs than in the paired control chamber baited only with the synthetic steroids. In field experiments, trap boxes baited with both the CPCs and the steroids captured 6.7-times more adult males and 4.7-times more juvenile males than trap boxes baited with the steroids alone. Conversely, trap boxes baited with both the CPCs and the steroids captured 4.3-times more adult males and 2.7-fold fewer adult females than trap boxes baited with the CPCs alone. In combination, these data support the conclusion that butyric acid, 2-methyl butyric acid and 4-heptanone are part of the sex attractant pheromone of female house mice. With progesterone and estradiol being pheromone components of both female brown rats, Rattus norvegicus, and female house mice, these three volatile components could impart specificity to the sexual communication system of house mice, brown rats and possibly other rodent species.


Assuntos
Camundongos/fisiologia , Atrativos Sexuais/análise , Comportamento Sexual Animal , Compostos Orgânicos Voláteis/análise , Animais , Ácido Butírico/análise , Ácido Butírico/metabolismo , Estradiol/análise , Estradiol/metabolismo , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Cetonas/análise , Cetonas/metabolismo , Masculino , Metilação , Progesterona/análise , Progesterona/metabolismo , Atrativos Sexuais/metabolismo , Compostos Orgânicos Voláteis/metabolismo
9.
J Nat Prod ; 82(7): 2009-2012, 2019 07 26.
Artigo em Inglês | MEDLINE | ID: mdl-31244148

RESUMO

As part of an ongoing program to identify sex attractant pheromone components that mediate sexual communication in yellowjacket wasps, a novel sesquiterpene was isolated from body surface extracts of virgin bald-faced hornet queens, Dolichovespula maculata. The gross structure of this sesquiterpene was proposed through microscale spectroscopic analyses, and the configuration of the central olefin was subsequently confirmed by total synthesis. This new natural product (termed here dolichovespulide) represents an important addition to the relatively small number of terpenoids reported from the taxonomic insect family Vespidae.


Assuntos
Vespas/química , Animais , Cromatografia Líquida de Alta Pressão , Estrutura Molecular , Análise Espectral/métodos
10.
Angew Chem Int Ed Engl ; 57(36): 11618-11622, 2018 09 03.
Artigo em Inglês | MEDLINE | ID: mdl-29890016

RESUMO

Yellowjackets in the genera Vespula and Dolichovespula are prevalent eusocial insects of great ecological and economic significance, but the chemical signals of their sexual communication systems have defied structural elucidation. Herein, we report the identification of sex attractant pheromone components of virgin bald-faced hornet queens (Dolichovespula maculata). We analyzed body surface extracts of queens by coupled gas chromatographic-electroantennographic detection (GC-EAD), isolated the compounds that elicited responses from male antennae by high-performance liquid chromatography (HPLC), and identified these components by GC mass spectrometry (MS), HPLC-MS, and NMR spectroscopy. In laboratory olfactometer experiments, synthetic (2Z,7E)-3,7-dimethyldeca-2,7-diendioic acid (termed here maculatic acid A) and (2Z,7E)-10-methoxy-3,7-dimethyldeca-10-oxo-deca-2,7-dienoic acid (termed here maculatic acid C) in binary combination significantly attracted bald-faced hornet males. These are the first sex attractant pheromone components identified in yellowjackets.


Assuntos
Feromônios/metabolismo , Atrativos Sexuais/metabolismo , Vespas/metabolismo , Animais , Cromatografia Líquida de Alta Pressão , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Espectroscopia de Ressonância Magnética , Masculino , Feromônios/análise , Atrativos Sexuais/análise , Vespas/química
11.
Chembiochem ; 18(14): 1391-1395, 2017 07 18.
Artigo em Inglês | MEDLINE | ID: mdl-28447367

RESUMO

Sex hormones of mammals control the expression of sexual characteristics and bodily functions. The male hormone testosterone and the female hormones progesterone and estradiol are known to occur in urine markings of mice. Here, we show that all three hormones are also present in urine of brown rats, and that they are effective sexual communication signals (pheromones) that elicit attraction behavior of prospective mates in both brown rats and house mice. When added as lures to trap boxes in field experiments, synthetic testosterone, for example, increased captures of adult female mice 15-fold, and a blend of progesterone and estradiol increased captures of male mice eightfold and male rats 13-fold. Remarkably, these hormones increased captures even though the food- and pheromone-based baits to which they were added had previously been shown to be superior to current commercial rodent attractants. We predict that these sex hormones will function as sex attractant pheromones in diverse taxa.


Assuntos
Hormônios Esteroides Gonadais/metabolismo , Atrativos Sexuais/metabolismo , Animais , Feminino , Hormônios Esteroides Gonadais/química , Masculino , Camundongos , Ratos , Atrativos Sexuais/química
12.
J Chem Ecol ; 43(3): 215-224, 2017 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-28130740

RESUMO

Urine of male house mice, Mus musculus, is known to have primer pheromone effects on the reproductive physiology of female mice. Urine-mediated releaser pheromone effects that trigger certain behavioral responses are much less understood, and no field studies have investigated whether urine deposits by male or female mice, or synthetic mouse pheromone, increase trap captures of mice. In field experiments, we baited traps with bedding soiled with urine and feces of caged female or male mice, and recorded captures of mice in these and in control traps containing clean bedding. Traps baited with female bedding preferentially captured adult males, whereas traps baited with male bedding preferentially captured juvenile and adult females, indicating the presence of male- and female-specific sex pheromones in soiled bedding. Analyses of headspace volatiles emanating from soiled bedding by gas chromatography/mass spectrometry revealed that 3,4-dehydro-exo-brevicomin (DEB) was seven times more prevalent in male bedding and that 2-sec-butyl-4,5-dihydrothiazole (DHT) was male-specific. In a follow-up field experiment, traps baited with DEB and DHT captured 4 times more female mice than corresponding control traps, thus indicating that DEB and DHT are sex attractant pheromone components of house mouse males. Our study provides impetus to identify the sex attractant pheromone of female mice, and to develop synthetic mouse pheromone as a lure to enhance the efficacy of trapping programs for mouse control.


Assuntos
Comportamento Animal/efeitos dos fármacos , Bioensaio , Laboratórios , Atrativos Sexuais/farmacologia , Animais , Roupas de Cama, Mesa e Banho , Feminino , Masculino , Camundongos , Odorantes/análise , Atrativos Sexuais/química
13.
J Insect Sci ; 17(5)2017 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-28922898

RESUMO

The German yellowjacket, Vespula germanica F., and common yellowjacket, Vespula vulgaris L. (Hymenoptera: Vespidae), are pests of significant economic, environmental, and medical importance in many countries. There is a need for the development and improvement of attractive baits that can be deployed in traps to capture and kill these wasps in areas where they are a problem. Yellowjackets are known to feed on fermenting fruit, but this resource is seldom considered as a bait due to its ephemeral nature and its potential attractiveness to nontarget species. We analyzed the headspace volatiles of dried fruit and fruit powder baits with and without Brewer's yeast, Saccharomyces cerevisiae, using gas chromatography-mass spectrometry, and we field tested these baits for their attractiveness to yellowjackets in Argentina. The addition of yeast to dried fruit and fruit powder changed the volatile compositions, increasing the number of alcohols and acids and decreasing the number of aldehydes. Dried fruit and fruit powder baits on their own were hardly attractive to yellowjackets, but the addition of yeast improved their attractiveness by 9- to 50-fold and surpassed the attractiveness of a commercial heptyl butyrate-based wasp lure. We suggest that further research be done to test additional varieties and species of yeasts. A dried fruit or fruit powder bait in combination with yeast could become a useful tool in the management of yellowjackets.


Assuntos
Frutas/química , Frutas/microbiologia , Controle de Insetos , Saccharomyces cerevisiae/química , Vespas/fisiologia , Animais , Cromatografia Gasosa-Espectrometria de Massas , Pós
14.
Chemistry ; 22(18): 6190-3, 2016 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-27001535

RESUMO

The sex pheromone of the endoparasitoid insect Xenos peckii (Strepsiptera: Xenidae) was recently identified as (7E,11E)-3,5,9,11-tetramethyl-7,11-tridecadienal. Herein we report the asymmetric synthesis of three candidate stereostructures for this pheromone using a synthetic strategy that relies on an sp(3) -sp(2) Suzuki-Miyaura coupling to construct the correctly configured C7-alkene function. Comparison of (1) H NMR spectra derived from the candidate stereostructures to that of the natural sex pheromone indicated a relative configuration of (3R*,5S*,9R*). Chiral gas chromatographic (GC) analyses of these compounds supported an assignment of (3R,5S,9R) for the natural product. Furthermore, in a 16-replicate field experiment, traps baited with the synthetic (3R,5S,9R)-enantiomer alone or in combination with the (3S,5R,9S)-enantiomer captured 23 and 18 X. peckii males, respectively (mean±SE: 1.4±0.33 and 1.1±0.39), whereas traps baited with the synthetic (3S,5R,9S)-enantiomer or a solvent control yielded no captures of males. These strong field trapping data, in combination with spectroscopic and chiral GC data, unambiguously demonstrate that (3R,5S,9R,7E,11E)-3,5,9,11-tetramethyl-7,11-tridecadienal is the X. peckii sex pheromone.


Assuntos
Aldeídos/química , Insetos/química , Feromônios/síntese química , Atrativos Sexuais/síntese química , Animais , Cromatografia Gasosa-Espectrometria de Massas , Espectroscopia de Ressonância Magnética , Masculino , Feromônios/química , Atrativos Sexuais/química , Estereoisomerismo
15.
J Chem Ecol ; 42(1): 40-50, 2016 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-26637207

RESUMO

We investigated foraging decisions by adult females of the common green bottle fly, Lucilia sericata, in accordance with their physiological state. When we gave female flies a choice between visually occluded, fresh canine feces (feeding site) and a CO2-euthanized rat (carrion oviposition site), 3-d-old "protein-starved" females responded equally well to feces and carrion, whereas protein-fed gravid females with mature oocytes responded only to carrion, indicating resource preferences based on a fly's physiological state. Dimethyl trisulfide (DMTS) is known to attract gravid L. sericata females to carrion. Therefore, we analyzed headspace from canine feces by gas chromatographic-electroantennographic detection (GC-EAD) and GC/mass spectrometry. In bioassays, of the 17 fecal odorants that elicited GC-EAD responses from fly antennae, a blend of indole and one or more of the alcohols phenol, m-/p-cresol and 1-octen-3-ol proved as attractive to flies as canine feces. Unlike young females, gravid females need to locate carrion for oviposition and distinguish between fresh and aging carrion, the latter possibly detrimental to offspring. Gravid female L. sericata accomplish this task, in part, by responding to trace amounts of DMTS emanating from fresh carrion and by discriminating against carrion as soon it begins to produce appreciable amounts of indole, which is also the second-most abundant semiochemical in fresh canine feces, and apparently serves as an indicator of food rather than oviposition resources. Our results emphasize the importance of studying foraging choices by flies in accordance with their physiological stage.


Assuntos
Dípteros/fisiologia , Fezes/química , Olfato , Animais , Comportamento Animal/efeitos dos fármacos , Dióxido de Carbono/farmacologia , Dípteros/efeitos dos fármacos , Cães , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Indóis/farmacologia , Odorantes/análise , Feromônios/análise , Ratos , Sulfetos/farmacologia , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/química
16.
J Chem Ecol ; 42(5): 414-24, 2016 May.
Artigo em Inglês | MEDLINE | ID: mdl-27146994

RESUMO

In eusocial insects like Bald-faced hornets, Dolichovespula maculata, nest defense is essential because nests contain a large number of protein-rich larvae and pupae, and thus are attractive to nest predators. Our objectives were to investigate whether D. maculata exhibit pheromone-mediated nest defense, and to identify and field test any pheromone components. We tested for pheromone-mediated nest defense behavior of D. maculata by placing a paired box-apparatus near the entrance of D. maculata nests, and treating both boxes with a solvent control, or one of the two boxes with a solvent control and the other with either venom sac extract, the putative source of nest defense pheromone, or synthetic pheromone. The sound impulses caused by nest mates attempting to sting or strike the boxes were recorded for 3 min. Compared to the double-control treatment, the number of strikes increased 27-fold when one of the two boxes was treated with venom sac extract, providing evidence for an alarm response. The box treated with venom sac extract also induced a significantly greater proportion of strikes than the corresponding control box, providing evidence for a target-oriented response. Analyzing venom sac extract by gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry resulted in the identification of seven candidate pheromone components: (a) dimethylaminoethanol, (b) dimethylamino ethyl acetate, (c) 2,5-dimethylpyrazine, (d) N-3-methylbutylacetamide, (e) 2-heptadecanone, (f) (Z)-8-heptadecen-2-one, and (g) (Z)-10-nonadecen-2-one. Testing in paired-box bioassays blends of the nitrogen-containing volatile components a-d, the less volatile ketones e-g, or both (a-g), indicated that a-d primarily have an alarm function. The ketones e-g, in contrast, induced target-oriented responses, possibly marking the box, or potential nest predators, for guided and concerted attacks, or enhancing the alarm-inducing effect of the volatile pheromone components, as shown in honey bees. Comparing the behavioral effects of venom sac extract, blends a-d, e-g, and a-g, venom sac extract was most effective in triggering the full complement of alarm and target-oriented responses. These comparisons further suggested that a component is missing in the group of components that triggers the alarm rather than the target-oriented response.


Assuntos
Comportamento de Nidação/efeitos dos fármacos , Feromônios/farmacologia , Vespas/efeitos dos fármacos , Vespas/fisiologia , Animais , Venenos de Artrópodes/química
17.
Angew Chem Int Ed Engl ; 55(20): 6062-6, 2016 05 10.
Artigo em Inglês | MEDLINE | ID: mdl-27060700

RESUMO

Trapping brown rats is challenging because they avoid newly placed traps in their habitat. Herein, we report the identification of the sex pheromone produced by male brown rats and its effect on trap captures of wild female brown rats. Collecting urine- and feces-soiled bedding material of laboratory-kept rats and comparing the soiled-bedding odorants of juvenile and adult males, as well as of adult males and females, we found nine compounds that were specific to, or most prevalent in, the odor profiles of sexually mature adult males. When we added a synthetic blend of six of these compounds (2-heptanone, 4-heptanone, 3-ethyl-2-heptanone, 2-octanone, 2-nonanone, 4-nonanone) to one of two paired food-baited trap boxes, these boxes attracted significantly more laboratory-strain female rats in laboratory experiments, and captured ten times more wild female rats in a field experiment than the corresponding control boxes. Our data show that the pheromone facilitates captures of wild female brown rats.


Assuntos
Cromatografia Gasosa-Espectrometria de Massas , Atrativos Sexuais/análise , Animais , Feminino , Masculino , Odorantes/análise , Ratos , Atrativos Sexuais/farmacologia , Comportamento Sexual Animal/efeitos dos fármacos
18.
J Chem Ecol ; 41(5): 465-72, 2015 May.
Artigo em Inglês | MEDLINE | ID: mdl-25940849

RESUMO

Chemical communication is common in spiders but few pheromones have been identified. Female widow spiders in the genus Latrodectus spin webs that disseminate an attractive sex pheromone, and a contact pheromone on the silk elicits courtship behavior by males. The methyl ester of N-3-methylbutanoyl-O-(S)-2-methylbutanoyl-L-serine is a contact pheromone of the Australian redback spider Latrodectus hasselti. We hypothesized that the contact pheromone of congeneric L. hesperus resembles that of L. hasselti. The silk of virgin L. hesperus females was extracted with methanol, and analyses by gas chromatography-mass spectrometry (GC/MS) provided evidence for the presence of N-3-methylbutanoyl-O-methylpropanoyl-L-serine methyl ester (MB-MP-S), a lower homologue of the L. hasselti contact pheromone. Behavioral responses of L. hesperus males to test stimuli were assayed on T-shaped rods with the end sections of the horizontal arm enveloped in filter paper. Males spent 40 % longer in contact with paper bearing female silk than with blank paper, and 39 % longer in contact with paper treated with silk extract than with solvent controls. Contact with silk and silk extract induced courtship behavior by 96 % and 80 % of males, respectively, indicating that there was a methanol-soluble courtship-eliciting contact pheromone on the silk. Males responded less strongly to synthetic MB-MP-S than to silk or silk extract. Paper impregnated with synthetic MB-MP-S (10 or 100 µg) induced courtship behavior in 3-16 % of males, and prompted males to stay 10-16 % longer than on control paper. Our data support the conclusion that MB-MP-S is part of a multi-component contact pheromone of L. hesperus.


Assuntos
Serina/análogos & derivados , Atrativos Sexuais/fisiologia , Comportamento Sexual Animal/fisiologia , Seda/química , Aranhas/fisiologia , Comunicação Animal , Animais , Feminino , Masculino , Serina/análise , Serina/fisiologia , Atrativos Sexuais/análise , Aranhas/química
19.
J Chem Ecol ; 41(8): 732-9, 2015 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-26271674

RESUMO

Xenos peckii is a strepsipteran parasitoid of the common North American paper wasp, Polistes fuscatus. Mate-seeking X. peckii males respond to a long-range sex pheromone emitted by the female, which remains permanently embedded within the abdomen of a mobile host wasp. During peak pheromone signalling, we excised the female from her host, severed the cephalothorax containing the pheromone gland, extracted it in hexane, and analyzed aliquots of combined extracts by coupled gas chromatographic-electroantennographic detection (GC-EAD). These analyses revealed a candidate pheromone component (CPC) that consistently elicited strong responses from male antennae. We identified the CPC as (7E,11E)-3,5,9,11-tetramethyltridecadienal based on its retention indices (RI) on three GC-columns, RI inter-column differentials, mass and NMR spectra, and synthesis of an authentic standard that matched the GC-retention and spectrometric characteristics of the CPC. For a field experiment, we prepared (7E,11E)-3,5,9R,11-tetramethyltridecadienal and (7E,11E)-3,5,9S,11-tetramethyltridecadienal. Xenos peckii males were caught in traps baited with either compound singly or a 1:1 mixture of the two but not in unbaited control traps. The sex pheromone of X. peckii resembles that reported for the strepsipterans Stylops mellittae and S. muelleri, (R,R,R)-3,5,9-trimethyldodecanal, suggesting a common biosynthetic pathway across taxonomic genera.


Assuntos
Antenas de Artrópodes/fisiologia , Insetos/metabolismo , Atrativos Sexuais/metabolismo , Animais , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Masculino
20.
Angew Chem Int Ed Engl ; 54(4): 1135-8, 2015 Jan 19.
Artigo em Inglês | MEDLINE | ID: mdl-25529634

RESUMO

Bed bugs have become a global epidemic and current detection tools are poorly suited for routine surveillance. Despite intense research on bed bug aggregation behavior and the aggregation pheromone, which could be used as a chemical lure, the complete composition of this pheromone has thus far proven elusive. Here, we report that the bed bug aggregation pheromone comprises five volatile components (dimethyl disulfide, dimethyl trisulfide, (E)-2-hexenal, (E)-2-octenal, 2-hexanone), which attract bed bugs to safe shelters, and one less-volatile component (histamine), which causes their arrestment upon contact. In infested premises, a blend of all six components is highly effective at luring bed bugs into traps. The trapping of juvenile and adult bed bugs, with or without recent blood meals, provides strong evidence that this unique pheromone bait could become an effective and inexpensive tool for bed bug detection and potentially their control.


Assuntos
Percevejos-de-Cama/química , Feromônios/análise , Aldeídos/análise , Aldeídos/isolamento & purificação , Animais , Percevejos-de-Cama/metabolismo , Comportamento Animal/efeitos dos fármacos , Cromatografia de Fase Reversa , Cromatografia Gasosa-Espectrometria de Massas , Hexanonas/análise , Hexanonas/isolamento & purificação , Histamina/farmacologia , Espectroscopia de Ressonância Magnética , Masculino , Feromônios/farmacologia
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