| 1. |
- Becher, Paul, et al.
(author)
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The Scent of the Fly
- 2018
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In: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 44:5, s. 431-435
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Journal article (peer-reviewed)abstract
- (Z)-4-undecenal (Z4-11Al) is the volatile pheromone produced by females of the vinegar fly Drosophila melanogaster. Female flies emit Z4-11Al for species-specific communication and mate-finding. A sensory panel finds that synthetic Z4-11Al has a characteristic flavour, which can be perceived even at the small amounts produced by a single female fly. Since only females produce Z4-11Al, and not males, we can reliably distinguish between single D. melanogaster males and females, according to their scent. Females release Z4-11Al at 2.4 ng/h and we readily sense 1 ng synthetic Z4-11Al in a glass of wine (0.03 nmol/L), while a tenfold concentration is perceived as a loud off-flavour. This corroborates the observation that a glass of wine is spoilt by a single D. melanogaster fly falling into it, which we here show is caused by Z4-11Al. The biological role of Z4-11Al or structurally related aldehydes in humans and the basis for this semiochemical convergence remains yet unclear.
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| 2. |
- Frey, T., et al.
(author)
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The human odorant receptor OR10A6 is tuned to the pheromone of the commensal fruit fly Drosophila melanogaster
- 2022
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In: iScience. - : Elsevier BV. - 2589-0042. ; 25:11
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Journal article (peer-reviewed)abstract
- All living things speak chemistry. The challenge is to reveal the vocabulary, the odorants that enable communication across phylogenies and to translate them to physiological, behavioral, and ecological function. Olfactory receptors (ORs) interface animals with airborne odorants. Expression in heterologous cells makes it possible to interrogate single ORs and to identify cognate ligands. The cosmopolitan, anthropophilic strain of the vinegar fly Drosophila melanogaster depends on human resources and housing for survival. Curiously, humans sense the pheromone (Z)-4-undecenal (Z4-11Al) released by single fly females. A screening of all human ORs shows that the most highly expressed OR10A6 is tuned to Z4-11Al. Females of an ancestral African fly strain release a blend of Z4-11Al and Z4-9Al that produces a different aroma, which is how we distinguish these fly strains by nose. That flies and humans sense Z4-11Al via dedicated ORs shows how convergent evolution shapes communication channels between vertebrate and invertebrate animals.
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| 3. |
- Lebreton, Sebastien, et al.
(author)
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A Drosophila female pheromone elicits species-specific long-range attraction via an olfactory channel with dual specificity for sex and food
- 2017
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In: BMC Biology. - : Springer Science and Business Media LLC. - 1741-7007. ; 15:1
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Journal article (peer-reviewed)abstract
- Background: Mate finding and recognition in animals evolves during niche adaptation and involves social signals and habitat cues. Drosophila melanogaster and related species are known to be attracted to fermenting fruit for feeding and egg-laying, which poses the question of whether species-specific fly odours contribute to long-range premating communication. Results: We have discovered an olfactory channel in D. melanogaster with a dual affinity to sex and food odorants. Female flies release a pheromone, (Z)-4-undecenal (Z4-11Al), that elicits flight attraction in both sexes. Its biosynthetic precursor is the cuticular hydrocarbon (Z,Z)-7,11-heptacosadiene (7,11-HD), which is known to afford reproductive isolation between the sibling species D. melanogaster and D. simulans during courtship. Twin olfactory receptors, Or69aB and Or69aA, are tuned to Z4-11Al and food odorants, respectively. They are co-expressed in the same olfactory sensory neurons, and feed into a neural circuit mediating species-specific, long-range communication; however, the close relative D. simulans, which shares food resources with D. melanogaster, does not respond to Z4-11Al. Conclusion: The Or69aA and Or69aB isoforms have adopted dual olfactory traits. The underlying gene yields a collaboration between natural and sexual selection, which has the potential to drive speciation.
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| 4. |
- Rahmani, Rizan, et al.
(author)
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Identification and Field Assay of Two Aggregation Pheromone Components Emitted by Males of the Bark Beetle Polygraphus punctifrons (Coleoptera: Curculionidae)
- 2019
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In: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 45:4, s. 356-365
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Journal article (peer-reviewed)abstract
- The bark beetle Polygraphus punctifrons (Coleoptera: Curculionidae) is a species that feeds on Norway spruce (Picea abies) and is found in the Northern parts of Europe and Russia. The release of volatile organic compounds (VOCs) produced by males and females of P. punctifrons when the beetles bore into spruce stem sections in a laboratory environment was studied using solid phase microextraction (SPME). The sampled VOCs emitted by boring beetles were analysed by gas chromatography and mass spectrometry (GCMS). (+)-2-[(1R,2S)-1-Methyl-2-(prop-1-en-2-yl)cyclobutyl]ethanol [(+)-(1R,2S)-grandisol] and (−)-(R)-1-isopropyl-4-methyl-3-cyclohexen-1-ol [(−)-(R)-terpinen-4-ol] were identified to be male specific volatiles. The identity of the compounds was confirmed by comparison with synthetic samples. Field trials with synthetic compounds in Sweden showed that racemic grandisol per se was strongly attractive for both males and females, while (−)-(R)-terpinen-4-ol was not. Further, when adding (−)-(R)-terpinen-4-ol to rac-grandisol, a synergistic effect was observed as the trap catch of P. punctifrons was fourfold. (−)-(R)-Terpinen-4-ol by its own did not attract P. punctifrons but Polygraphus poligraphus, and the latter was also attracted to traps baited with a 10:90 mixture of the two compounds. Thus, we have identified (+)-(1R,2S)-grandisol as a main component and (−)-(R)-terpinen-4-ol as a minor component of the aggregation pheromone of P. punctifrons. This opens future possibilities to monitor and, if necessary, manage populations of P. punctifrons.
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| 5. |
- Wallin, Erika A., 1985-, et al.
(author)
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Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella
- 2020
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In: Scientific Reports. - : Springer Science and Business Media LLC. - 2045-2322. ; 10:1
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Journal article (peer-reviewed)abstract
- The bumblebee wax moth, Aphomia sociella, is a parasite of bumblebees. In this species, males produce sexual pheromone to attract females, while females produce an aphrodisiac pheromone that initiates male courtship. Both pheromones contain 6,10,14-trimethylpentadecan-2-one (TMPD-one) and the corresponding alcohol, 6,10,14-trimethylpentadecan-2-ol (TMPD-ol) in sex specific quantities. Male sex pheromone consists of 7 components with TMPD-one as a minor one and traces of TMPD-ol. In female aphrodisiac pheromone, TMPD-ol is the major component, while TMPD-one is present in traces. Here we report on the absolute configuration of TMPD-one in male sex pheromone and TMPD-ol in female aphrodisiac pheromone of A. sociella. The configuration was determined from GC/MS of prepared (S)-acetoxypropionyl esters of TMPD-ol. TMPD-one was first reduced to the alcohol that was then derivatized with (S)-acetoxypropionyl chloride. The GC/MS data of obtained diastereoisomers were compared with synthetic standards. The absolute configuration of TMPD-one in the male pheromone was (6R,10R). The configuration of TMPD-ol in the female pheromone was (2R,6R,10R). Electrophysiological experiments showed that TMPD-one and TMPD-ol are perceived by both sexes. The synthetic standards of naturally produced stereoisomers elicited higher responses than mixtures of all stereoisomers.
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| 6. |
- Wallin, Erika, 1985-
(author)
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The Scents of Nature : Identification and Synthesis of Bioactive Compounds Used in Insect Communication
- 2014
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Doctoral thesis (other academic/artistic)abstract
- Pest insects cause great financial losses in the forest and food industry every year. To fight these pests industries have used insecticides, which are sometimes harmful to nature and humans. One potential way of avoiding insecticides is the use of integrated pest management based on insect communication, which would offer species-specific methods for protecting forest and food resources. Insects use chemicals known as semiochemicals for both intra- and interspecies communication. By learning how insects use these semio-chemicals to talk to each other we can eavesdrop and mimic their communication for our benefit. One research area dealing with these questions is chemical ecology, which is an interdisciplinary area as knowledge in chemistry and biology is required. Collaborations between groups within and outside of Sweden are essential in order to make progress in this field of research.This thesis presents the identification and synthesis of semiochemicals from several insect species, most of which are considered to be pests. Synthesised compounds have been sent to collaboration partners around Sweden and Europe for biological evaluations.Studies of the African butterfly, Bicyclus anynana, have unravelled particular biological phenomena that may aid in the understanding of the Bicyclus genus, though recognizing individual species variation is crucial. In 2008 the putative male sex pheromone of B. anynana was determined to consist of three compounds: hexadecanal, (Z)-9-tetradecenol and 6,10,14-trimethylpentadecan-2-ol, and the specific stereoisomer for 6,10,14-trimethylpentadecan-2-ol has been determined in this thesis. The ratio of 6,10,14-trimethylpentadecan-2-ol and the corresponding ketone were investigated for seventeen Bicyclus species (including B. anynana) that live in overlapping regions in Africa. The stereochemistry was determined for most of the species and may provide a way to chemically distinguish them.The orchid bees, Euglossa spp, are important pollinators of many orchids in Central America. Insight about pollination and conservation of endangered orchid species may be possible by gathering more information about the Euglossa genus. Males of the Euglossa genus have pouch-like structures on their hind legs where they store compounds collected from their surroundings. 6,10,14-Trimethyl-pentadecan-2-one is a common component of leg extracts from Euglossa imperialis, E. crassipunctata and E. allosticta, the specific stereochemistry of which has been determined in this thesis. Another, different compound was found in high amounts in E. viridissima and its structure has been elucidated; several synthetic pathways are under investigation to obtain the target compound.Bed bugs (Cimex lectularius and C. hemipterus) are an ectoparasite that feed on human blood, and the number of reported infestations of these parasites has increased considerably during the last decade. Two 5th instar nymph-specific compounds, 4-oxo-hexenal and 4-oxo-octenal, were identified and synthesised.Utilizing domestic dogs (Canis lupus familiaris) in the identification of bed bug infestations has become popular during recent years. Their training is usually conducted using live bed bugs, however this thesis describes an alternative method of teaching dogs to find infestations. This alternative method is based on synthetic compounds and dogs trained in this manner have achieved a high positive indication rate.Two species of the tiny, Acacia leaf-eating insect pests in Australia known as thrips, Kladothrips nicolsoni and K. rugosus, have been investigated by means of larval extracts and have been shown to contain large amount of (Z)-3-dodecenoic acid which was synthesised and tested in bioassays.Fruit flies are common pests on fruit in almost every private household. Even though fruit flies has been investigated extensively, their chemical communication has not been completely elucidated. (Z)-4-undecenal was identified as a compound emitted by females, it was synthesised in high stereoisomeric purity and evaluated in biological assays.
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| 7. |
- Wallin, Erika, 1985-, et al.
(author)
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(Z)-3-Dodecenoic Acid Is the Main Component of Full-Body n-Hexane Extracts from Two Acacia Gall-Inducing Thrips (Thysanoptera) and May Function as an Alarm Pheromone
- 2014
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In: Zeitschrift für Naturforschung C - A Journal of Biosciences. - 0939-5075 .- 1865-7125. ; 69C:7-8, s. 335-345
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Journal article (peer-reviewed)abstract
- A major interest in the gall-inducing thrips of Australia began with the discovery that some species have eusocial colonies. The origin of social castes remains one of the outstanding questions in evolutionary biology. The inference of the ancestral stage from study of solitary species is important to understanding the evolutionary history of semiochemicals in the social species. Here we investigated two solitary species, Kladothrips nicolsoni and K. rugosus. Whole body extracts revealed that (Z)-3-dodecenoic acid, here reported for the first time in a thrips species, is the main component. (Z)-3-Dodecenoic acid and (E)-3-dodecenoic acid were synthesized in high stereoisomeric purity (> 99.8 %) and exposed to K. nicolsoni 2nd-instar larvae in a contact chemoreception bioassay to test for potential bioactivity. Both isomers decreased the average time spent in the treated area per entry suggesting repellence at the tested dose. (Z)-3-Dodecenoic acid may function as alarm pheromone. (E)-3-Dodecenoic acid increased also the absolute change in direction of larvae compared to an n-hexane control and could potentially function as a repellent.
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