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  • 1.
    Becher, Paul G.
    et al.
    Swedish University of Agricultural Sciences, Alnarp.
    Lebreton, Sebastien
    Swedish University of Agricultural Sciences, Alnarp.
    Wallin, Erika
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Borrero, Felipe
    Colombian Corporation of Agricultural Research, Las Palmas, Bogota, Colombia.
    Bengtsson, Marie
    Swedish University of Agricultural Sciences, Alnarp.
    Joerger, Volker
    Staatliches Weinbauinstitut, Freiburg, Germany.
    Witzgall, Peter
    Swedish University of Agricultural Sciences, Alnarp.
    The Scent of the Fly2018In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 44, no 5, p. 431-435Article in journal (Refereed)
    Abstract [en]

    (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. 

  • 2. Eltz, Thomas
    et al.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Bång, Joakim
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Wallin, Erika A
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Andersson, Jimmy
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    (6R,10R)-6,10,14-Trimethylpentadecan-2-one, a Dominant and Behaviorally Active Component in Male Orchid Bee Fragrances2010In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 36, no 12, p. 1322-1326Article in journal (Refereed)
    Abstract [en]

    6,10,14-Trimethylpentadecan-2-one (Hexahydrofarnesyl acetone; HHA) previously has been found to be a major component in tibial fragrances of male orchid bees, Euglossa spp. HHA is a chiral molecule with four possible stereoisomers, (6R,10R)-, (6R,10S)-, (6S,10R)-, and (6S,10S)-6,10,14-trimethylpentadecan-2-one. In the present study, we characterized HHA extracted from Euglossa as the pure enantiomer (6R,10R)-6,10,14-trimethylpentadecan-2-one. During bioassays in Mexico and Panama, the synthetic RR-isomer attracted males of six species of orchid bees, including three that were known to contain HHA in their tibial fragrances. Possible sources of HHA for wild bees are flowers of euglossophilous orchids and aroids. With a molecular weight of 268, HHA is the largest natural molecule known to attract male orchid bees in pure form. Its attractiveness to males suggests that low-volatility compounds have a function in male signals, e.g., serve as a "base note" in complex odor bouquets. © 2010 Springer Science+Business Media, LLC.

  • 3.
    Hedenström, Erik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Wallin, Erika
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Andersson, J
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Bång, Joakim
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Wang, H-L
    Department of Biology, Lund University, Sölvegatan 37, Lund, Sweden .
    Löfstedt, C
    Department of Biology, Lund University, Sölvegatan 37, Lund, Sweden .
    Brattström, O
    Department of Zoology, Cambridge University, Cambridge, United Kingdom.
    Baquet, P
    Evolutionary Ecology and Genetics group, Biodiversity Research Centre, Earth and Life Institute, Académie Louvain, Croix du Sud 4, Louvain-la-Neuve, Belgium.
    Stereoisomeric Analysis of 6,10,14-Trimethylpentadecan-2-ol and the Corresponding Ketone in Wing Extracts from African Bicyclus Butterfly Species2015In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 41, no 1, p. 44-51Article in journal (Refereed)
    Abstract [en]

    Gas chromatography (GC) and mass spectrometry (MS) were used to determine the stereoisomeric compositions of 6,10,14-trimethylpentadecan-2-ol and 6,10,14-trimethylpentadecan-2-one in wing extracts from 17 Bicyclus butterfly species from different regions of Africa. All samples were purified using solid phase extraction (SPE). Since some species contained both alcohol and ketone, these were separated and the ketone was reduced to the alcohol before analysis as either (R)-trans-chrysanthemoyl or (S)-2-acetoxypropionyl esters. A novel asymmetric synthesis was developed for a reference mixture of (2R/S,6S,10R)-6,10,14-trimethylpentadecan-2-ol with known composition of the eight stereoisomers. The mixture then was used as the (R)-trans-chrysanthemoyl esters to correlate each of the eight gas chromatographic peaks to a specific stereoisomer of the extracted wing compounds. Seven butterfly species showed (2R,6R,10R)-configuration of the alcohol, four species contained minute amounts of alcohol too small to determine the stereochemistry, nine species showed (6R,10R)-configuration of the ketone, and one species contained minute amounts of ketone too small to determine the stereochemistry. No other stereoisomers of alcohol or ketone could be detected in the extracts, and the quantities of the compounds in the wing extracts varied from 5 to 900 ng per sample for each species.

  • 4.
    Lebreton, Sebastien
    et al.
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp.
    Borrer-Echeverry, Felipe
    Biological Control Laboratory, Colombian Corporation of Agricultural Research, Las Palmas, Bogota, Colombia.
    Gonzalez, Francisco
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp.
    Solum, Marit
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp.
    Wallin, Erika
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Hansson, Bill S
    Department of Evolutionary Neuroethology, Max Planck Institute for Chemical Ecology, Jena, Germany.
    Gustavsson, Anna-Lena
    Department of Medical Biochemistry and Biophysics, Karolinska Institutet, Solna.
    Bengtsson, Marie
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp.
    Birgersson, Göran
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp.
    Walker, William B
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp.
    Dweck, Hany KM
    Department of Evolutionary Neuroethology, Max Planck Institute for Chemical Ecology, Jena, Germany; Department of Molecular, Cellular, and Developmental Biology, Yale University, New Haven, USA.
    Becher, Paul G
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp.
    Witzgall, Peter
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp.
    A Drosophila female pheromone elicits species-specific long-range attraction via an olfactory channel with dual specificity for sex and food2017In: BMC Biology, ISSN 1741-7007, E-ISSN 1741-7007, Vol. 15, no 1, article id 88Article in journal (Refereed)
    Abstract [en]

    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.

  • 5.
    Liedtke, H. Christoph
    et al.
    Lund Univ, Dept Ecol, S-22362 Lund, Sweden.
    Åbjörnsson, Kajsa
    Lund Univ, Dept Ecol, S-22362 Lund, Sweden.
    Harraca, Vincent
    Lund Univ, Dept Ecol, S-22362 Lund, Sweden.
    Knudsen, Jette
    Lund Univ, Dept Ecol, S-22362 Lund, Sweden.
    Wallin, Erika
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Ryne, Camilla
    Lund Univ, Dept Ecol, S-22362 Lund, Sweden.
    Alarm pheromones and chemical communication in nymphs of the tropical bed bug Cimex hemipterus (Hemiptera: Cimicidae)2011In: PLoS ONE, ISSN 1932-6203, E-ISSN 1932-6203, Vol. 6, no 3, p. e18156-Article in journal (Refereed)
    Abstract [en]

    The recent resurge of bed bug infestations (Cimex spp.; Cimicidae) and their resistance to commonly used pesticides calls for alternative methods of control. Pheromones play an important role in environmentally sustainable methods for the management of many pest insects and may therefore be applicable for the control of bed bugs. The tropical bed bug, Cimex hemipterus, is a temporary ectoparasite on humans and causes severe discomfort. Compared to the common bed bug, Cimex lectularius, little is known about the chemical signalling and pheromone-based behaviour of the tropical species. Here, we show that the antennal morphology and volatile emission of C. hemipterus closely resembles those of C. lectularius and we test their behavioural responses to conspecific odour emissions. Two major volatiles are emitted by male, female and nymph C. hemipterus under stress, (E)-2-hexenal and (E)-2-octenal. Notably, nymph emissions show contrasting ratios of these compounds to adults and are further characterized by the addition of 4-oxo-(E)-2-hexenal and 4-oxo-(E)-2-octenal. The discovery of this nymph pheromone in C. hemipterus is potentially the cause of a repellent effect observed in the biotests, where nymph odours induce a significantly stronger repellent reaction in conspecifics than adult odours. Our results suggest that pheromone-based pest control methods developed for C. lectularius could be applicable to C. hemipterus, with the unique nymph blend showing promising practical properties.

  • 6.
    Nieberding, Caroline M
    et al.
    Evolutionary Biology Group, Institute of Biology, Leiden University, 2300 RA Leiden, Netherlands.
    Fischer, Klaus
    Zoological Institute and Museum, Greifswald University, Johann-Sebastian-Bach Str. 11/12, 17489 Greifswald, Germany.
    Saastamoinen, Marjo
    Metapopulation Research Group, Department of BioSciences, University of Helsinki, PO Box 65 (Viikinkaari 1), FI-00014, Finland.
    Allen, Cerisse E
    Division of Biological Sciences, University of Montana, Missoula MT 59812, United States.
    Wallin, Erika A.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Brakefield, Paul M
    University Museum of Zoology Cambridge, Downing Street, Cambridge, CB2 3EJ, United Kingdom.
    Cracking the olfactory code of a butterfly: the scent of ageing.2012In: Ecology Letters, ISSN 1461-023X, E-ISSN 1461-0248, Vol. 15, no 5, p. 415-424Article in journal (Refereed)
    Abstract [en]

    Ecology Letters (2012) 15: 415-424 ABSTRACT: Although olfaction is a primary mode of communication, its importance in sexual selection remains understudied. Here, using the butterfly Bicyclus anynana, we address all the parameters of importance to sexual selection for a male olfactory signal. We show that variation in the male sex pheromone composition indicates male identity and male age. Courting males of different ages display small absolute (c. 200 ng) but large relative (100%) change of one specific pheromone component (hexadecanal) which, unlike the other components, showed no heritability. Females prefer to mate with mid-aged over younger males and the pheromone composition is sufficient to determine this preference. Surprisingly refined information is thus present in the male olfactory signal and is used for sexual selection. Our data also reveal that there may be no 'lek paradox' to resolve once the precise signal of importance to females is identified, as hexadecanal is, as expected, depleted in additive genetic variation.

  • 7.
    Rahmani, Rizan
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Wallin, Erika
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Viklund, Lina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Schroeder, Martin
    Swedish University of Agricultural Sciences, Uppsala.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Identification and Field Assay of Two Aggregation Pheromone Components Emitted by Males of the Bark Beetle Polygraphus punctifrons (Coleoptera: Curculionidae)2019In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 45, no 4, p. 356-365Article in journal (Refereed)
    Abstract [en]

    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. 

  • 8.
    Wallin, Erika
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    The Scents of Nature: Identification and Synthesis of Bioactive Compounds Used in Insect Communication2014Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    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.

  • 9.
    Wallin, Erika
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Andersson, Annica
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Chemical tools for training domestic dogs (Canis lupus familiaris) to detect bed bugsManuscript (preprint) (Other academic)
  • 10.
    Wallin, Erika
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    De Facci, Monica
    Department of Biology, Lund University, Sölvegatan 37, SE-223 62 Lund, Sweden .
    Anderbrant, Olle
    Department of Biology, Lund University, Sölvegatan 37, SE-223 62 Lund, Sweden .
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    (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 Pheromone2014In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 69C, no 7-8, p. 335-345Article in journal (Refereed)
    Abstract [en]

    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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