5-Methyl-2-phenyl-2-hexenal in the scent gland secretion of male cave crickets, Troglophilus cavicola and T. neglectus (Ensifera: Rhaphidophoridae) (original) (raw)
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Male-produced sex attractant pheromone of the green stink bug, Acrosternum hilare (Say)
Journal of chemical ecology, 2001
Sexually mature virgin adult males of the green stink bug, Acrosternum hilare attracted sexually mature virgin adult females in laboratory bioassays using a vertical Y-tube. There was no indication that males attracted other males, or that females attracted either sex. These results suggested that A. hilare males produce a sex pheromone. Extracts of odors collected from sexually mature males contained compounds that were not present in extracts from females or sexually immature males. (4S)-Cis-(Z)-bisabolene epoxide ((4S)-cis-Z-BAE) was the major sex-specific component of the extract. The crude extract was attractive to female A. hilare, but when separated into four fractions, only the portion containing (4S)-cis-Z-BAE and the minor component (4S)-trans-Z-BAE was attractive to females. This fraction was as attractive as the crude extract, suggesting that the former contained all the pheromone components. Neither synthetic (4S)-cis-Z-BAE nor (4S)-trans-Z-BAE alone was attractive to f...
Male-produced anti-sex pheromone in a plant bug
Naturwissenschaften, 2003
In plant bugs (Miridae), females produce sex pheromones in the metathoracic scent gland, which in most other true bugs (Heteroptera) is responsible for chemical defense. The possibility that the metathoracic gland secretion of male plant bugs plays a role other than defense has been largely overlooked. Here we show that in a pine-inhabiting mirid, Phytocoris difficilis Knight, hexyl butyrate and (E)-2-hexenyl butyrate are abundantly produced only in males; we demonstrate that these metathoracic gland compounds elicit strong antennal responses in conspecific males, and that these butyrates totally interrupt attraction of males to the femaleproduced sex pheromone. Our results suggest that in at least some plant bugs the male metathoracic scent gland esters have a natural communicative function as anti-sex pheromones, probably to interrupt further mating attempts by other males.
Journal of the Entomological Research Society, 2009
The metathoracic scent glands (MTGs) system of adult Rhaphigaster nebulosa (Heteroptera: Pentatomidae) was described by electron microscopy and secretion from them was analysed by a combination of gas chromatography and mass spectrometry (GC-MS). The MTGs is anatomically complex. It opens ventrally by paired openings located between the metathoracic furcae. It belongs to the paired MTG type and comprises on each side: median reservoir, lateral glands and evaporation surfaces. Median reservoir is sac-like and flanked by multitubular lateral glands. It is interconnected by a narrow bridge in the ventral mid-line. Metathoracic coxae are associated with crescent-like evaporation areas. Chemical analyses showed a typical pentatomid MTG composition. The glands of R. nebulosa males and females contain 9 same compounds: n-undecane, n-dodecane, n-tridecane, n-nonacosane, (E)-2-hexenal, (E)-2-octenal, (E)-2-decenal, (E)-2-hexenyl acetate, 2(5H)-furanone being the two major compounds n-tridecane and (E)-2-hexanal, which represent 90-95% of the secretion in the this species. The compounds n-tricosane, (Z)-cyclodecene, and (E)-2-decen-1-ol were detected only in females, while n-tetracosane, n-hexacosane, and 1-tridecene were detected only in males.
Journal of the Brazilian Chemical Society, 2016
Bark bugs belonging to the family Phloeidae are known for their camouflage on tree trunks. The nymphs store in dorsal abdominal glands defensive secretions with a pungent odor mainly constituted of (E)-2-hexenal, (E)-2-octenal, and (E)-4-oxo-2-hexenal. The metathoracic glands of adults (male and female) store (E)-2-hexen-1-ol and (E)-2-hexenyl acetate, which are less irritating than their corresponding aldehydes. Additional compounds of m/z 224 were detected in the scent glands of these insects and were previously suggested to be dimers of the (E)-4-oxo-2-hexenal. Thus, the aim of this study was to elucidate the details of the chemical structure of the dimers found in the scent glands of Phloea subquadrata. These dimers were obtained by synthesis and were compared with the natural products, confirming the dimeric structures of the latter. These (E)-4-oxo-2-hexenal dimeric compounds are novel and have not been reported before.
Archives of Insect Biochemistry and Physiology, 1994
De novo synthesis of contact female sex pheromone and hydrocarbons in Blaitella germanica was examined using short in vivo incubations. Accumulation of pheromone on the epicuticular surface and the internal pheromone titer were related to age-specific changes in hydrocarbon synthesis and accumulation in normal and allatectomized females. The incorporation of radiolabel from [l -'4C]pr~pionate into the cuticular methyl ketone pheromone fraction was positively related to corpora allata activity during two gonotrophic cycles. During peak pheromone production the total internal lipid fraction contained greater titers of pheromone than the cuticular surface, and it too exhibited a cycle internally, preceding the rise in external pheromone. This suggests that synthesis and accumulation of pheromone internally are followed by transport of pheromone to the epicuticular surface where it accumulates. Radiolabel was incorporated efficiently into both cuticular and internal hydrocarbons after the imaginal molt and until the peak of pheromone synthesis, but it declined to lower levels before ovulation and throughout pregnancy. The internal hydrocarbon titer decreased 58% after oviposition, suggesting deposition in the egg case. It remained relatively unchanged during pregnancy and increased again during the second gonotrophic cycle. In allatectomized females, hydrocarbon synthesis was reduced relative to control females until oviposition in the latter. However, subsequent rates of hydrocarbon synthesis in allatectomized females (without oothecae) exceeded the rates in sham-operated females (with oothecae). In the absence of ovarian uptake of hydrocarbons, the internal titer increased without the decline found in control females at oviposition. As internal hydrocarbons increased, so did cuticular hydrocarbons and both internal and cuticular methyl ketone pheromones. These patterns corresponded well with feeding patterns in sham-operated and allatectomized females, suggesting that NC 27695-761 3. Address reprint requests there. 0 1994 WBey-Liss, Inc.
Novel Exocrine Secretions from Two Species of Scentless Plant Bugs (Hemiptera: Rhopalidae)
Entomologia Experimentalis et Applicata, 1979
Adults of two species of so-called scentless plant bugs (Hemiptera: Rhopalidae) actually produce copious exocrine secretions from metathoracic and/or dorsal abdominal glands. Niesthrea louisianica adults possess a well-developed metathoracic gland and a single dorsal abdominal gland. In adults of Jadera haematoloma the metathoracic gland is vestigial, but two dorsal abdominal glands are present. The secretions from these species are not characteristic of the Hemiptera in that they are comprised either exclusively of monoterpenes or of blends of monoterpenes and the mono-unsaturated aliphatic aldehydes commonly encountered in hemipteran exudates. The monoterpenes, including a-pinene, 8pinene, myrcene, limonene, and thymol, as well as the aldehydes, (E)-2-hexenal and (E)-2-octenal, are apparently synthesized de novo.
Naturwissenschaften, 2013
An investigation to identify a sex or aggregation pheromone of Sitona discoideus Gyllenhål (Coleoptera: Curculionidae) is presented. Antenna flicking and attraction behaviors evoked by conspecifics of both sexes were recorded in arena bioassays, where attraction of females to males was observed. Air entrainment of both males and females was conducted in separate chambers. Gas chromatographic-mass spectrometric analysis of headspace volatiles revealed that two malespecific compounds, 4-methyl-3,5-heptanedione (major) and (4S,5S)-5-hydroxy-4-methyl-3-heptanone (minor), were emitted during the autumnal post-aestivatory flight period. The stereoisomers of the minor component were separated by enantioselective gas chromatography and their absolute configurations assigned by NMR (diastereomers) and the known preference of enantioselective transesterification reactions catalyzed by Candida antarctica lipase B. Electroantennogram and single sensillum recording studies indicate that 4-methyl-3,5-heptanedione as well as all individual stereoisomers of 5-hydroxy-4methyl-3-heptanone are detected by the antennae of male and female S. discoideus. Further, single sensillum recordings suggest that both sexes of S. discoideus have specialized olfactory receptor neurons (ORNs) for detecting 4-methyl-3,5-heptanedione and different populations of stereoselective ORNs for detecting the stereoisomers of 5-hydroxy-4-methyl-3-heptanone. Some of these stereoselective ORNs appear to be sexspecific in S. discoideus.
Journal of Chemical Ecology, 2013
Analysis of the sex pheromone gland of virgin Synanthedon scoliaeformis females by gas chromatography/ mass spectrometry revealed six compounds structurally related to sex pheromone components of other clearwing moths: (E,Z)-2,13-octadecadienyl acetate (E2,Z13-18:OAc), (E,Z)-2,13-octadecadienol, octadecanol acetate, octadecanol, (Z,Z)-3,13-octadecadienyl acetate (Z3,Z13-18:OAc), and (Z)-13octadecenyl acetate. Trapping tests demonstrated that E2,Z13-18:OAc is the sex pheromone of S. scoliaeformis and is essential for attracting males; addition of the other compounds did not enhance catch. Synanthedon scoliaeformis and S. tipuliformis are the only Palearctic clearwing moths whose distribution range and seasonal flight periods overlap and that are known to use E2,Z13-18:OAc in sex pheromonal communication. Hourly monitoring of male catches in traps revealed that sex pheromone communication in S. scoliaeformis and S. tipuliformis species follows different diurnal patterns. Z3,Z13-18:OAc, found in S. scoliaeformis females, is a known behavioral antagonist against S. tipuliformis males, while (E,Z)-3,13octadecadienyl acetate, a minor sex pheromone component of S. tipuliformis, is an antagonist against S. scoliaeformis males.
Food and humidity affect sex pheromone ratios in the stink bug, Euschistus heros
Physiological Entomology, 2008
Male stink bugs, Euschistus heros , only produce the three-component sex pheromone blend consisting of methyl-(2 E ,4 Z)-decadienoate, methyl-2,4,6-trimethyldodecanoate and methyl-2,4,6-trimethyltridecanoate in a constant ratio of 53 : 3 : 44, respectively, when provided with a food source (green beans, Phaseolus vulgaris). When volatiles are collected from insects with drinking water, humidified air, or under dry conditions, the insects stop producing two components (methyl-2,4,6-trimethyldodecanoate and methyl-2,4,6-trimethyltridecanoate) after 1 day and increase the amount of defensive compounds produced [e.g. (E)-2-hexenal, decane]. Methyl-2,4,6-trimethyltridecanoate is able to change the behaviour of females but not males. Dual-choice olfactometer bioassays with synthetic standards of all three components, as well as the ternary mixture in the correct ratio, induce a response from females but not males, indicating that all three components have a role in sexual communication. Thus, the dietary conditions under which volatile collections are carried out are crucial for determination of the precise sex pheromone blend.
Journal of Agricultural Science and Technology, 2019
Eurygaster maura (L.) (Heteroptera: Scutelleridae) is one of the most devastating pests of wheat in Turkey. The metathoracic scent gland secretions of male and female E. maura were analyzed separately by gas chromatography-mass spectrometry. Twelve chemical compounds, namely, Octane, n-Undecane, n-Dodecane, n-Tridecane, (E)-2-Hexenal , (E)2-Hexen-1-ol, acetate, Cyclopropane, 1-ethyl-2-heptyl, Hexadecane, (E)-3-Octen-1-ol, acetate, (E)-5-Decen-1-ol, acetate, 2-Hexenoic acid, Butyric acid, and Tridecyl ester were detected in both males and females. These compounds, however, differed quantitatively between the sexes. In both females and males, n-Tridecane and (E)-2-Hexanal were the most abundant compounds and constituted approximately 90% of the total content. Minimal amounts of Octane were detected in males and Hexadecane in females.