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1.
  • Borrero, Felipe, et al. (författare)
  • Yeast Volatomes Differentially Affect Larval Feeding in an Insect Herbivore
  • 2019
  • Ingår i: Applied and Environmental Microbiology. - 0099-2240 .- 1098-5336. ; 85
  • Tidskriftsartikel (refereegranskat)abstract
    • Yeasts form mutualistic interactions with insects. Hallmarks of this interaction include provision of essential nutrients, while insects facilitate yeast dispersal and growth on plant substrates. A phylogenetically ancient chemical dialogue coordinates this interaction, where the vocabulary, the volatile chemicals that mediate the insect response, remains largely unknown. Here, we used gas chromatography-mass spectrometry, followed by hierarchical cluster and orthogonal partial least-squares discriminant analyses, to profile the volatomes of six Metschnikowia spp., Cryptococcus nemorosus, and brewer's yeast (Saccharomyces cerevisiae). The yeasts, which are all found in association with insects feeding on foliage or fruit, emit characteristic, species-specific volatile blends that reflect the phylogenetic context. Species specificity of these volatome profiles aligned with differential feeding of cotton leafworm (Spodoprera littoralis) larvae on these yeasts. Bioactivity correlates with yeast ecology; phylloplane species elicited a stronger response than fruit yeasts, and larval discrimination may provide a mechanism for establishment of insect-yeast associations. The yeast volatomes contained a suite of insect attractants known from plant and especially floral headspace, including (Z)-hexenyl acetate, ethyl (2E,4Z)-deca-2,4-dienoate (pear ester), (3E)-4,8-dimethylnona-1,3,7-triene (DMNT), linalool, alpha-terpineol, beta-myrcene, or (E,E)-alpha-farnesene. A wide overlap of yeast and plant volatiles, notably floral scents, further emphasizes the prominent role of yeasts in plant-microbe-insect relationships, including pollination. The knowledge of insect-yeast interactions can be readily brought to practical application, as live yeasts or yeast metabolites mediating insect attraction provide an ample tool-box for the development of sustainable insect management.IMPORTANCE Yeasts interface insect herbivores with their food plants. Communication depends on volatile metabolites, and decoding this chemical dialogue is key to understanding the ecology of insect-yeast interactions. This study explores the volatomes of eight yeast species which have been isolated from foliage, from flowers or fruit, and from plant-feeding insects. These yeasts each release a rich bouquet of volatile metabolites, including a suite of known insect attractants from plant and floral scent. This overlap underlines the phylogenetic dimension of insect-yeast associations, which according to the fossil record long predate the appearance of flowering plants. Volatome composition is characteristic for each species, aligns with yeast taxonomy, and is further reflected by a differential behavioral response of cotton leafworm larvae, which naturally feed on foliage of a wide spectrum of broad-leaved plants. Larval discrimination may establish and maintain associations with yeasts and is also a substrate for designing sustainable insect management techniques.
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2.
  • Anderbrant, Olle, et al. (författare)
  • Release of sex pheromone and its precursors in the pine sawfly Diprion pini (Hym., Diprionidae)
  • 2005
  • Ingår i: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 15:3, s. 147-151
  • Tidskriftsartikel (refereegranskat)abstract
    • The first identification of a sex pheromone of a pine sawfly (Hymenoptera, Diprionidae) dates back almost thirty years. Since then, female-produced pheromones of over twenty diprionid species have been investigated by solvent extraction followed by separation and identification. However, no study has shown what the females actually release. Collection of airborne compounds using absorbtion on charcoal filter as well as solid phase microextraction (SPME) followed by analysis employing gas chromatography combined with mass spectrometry (GC-MS), revealed an unusual system in Diprion pini, in which the pheromone precursor alcohol, 3,7-dimethyl-2-tridecanol, is released together with acetic, propionic, butyric and isobutyric acids. The corresponding acetate, propionate and butyrate esters of 3,7-dimethyl-2-tridecanol were also found in the samples. All esters were electrophysiologically active, and the propionate and isobutyrate were attractive in trapping experiments. Based on these and earlier reported results, it seems that at least in part of its range, the pheromone response of D. pini is not very specific with regard to the functional group, as long as this is an ester.    
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3.
  • Hedenström, Erik, et al. (författare)
  • Sex pheromone of the pine sawfly, Gilpinia pallida: Chemical identification, synthesis, and biological activity
  • 2006
  • Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 32:11, s. 2525-2541
  • Tidskriftsartikel (refereegranskat)abstract
    • We present the identification of the sex pheromone in the pine sawfly, Gilpinia pallida, including analysis of the female pheromone content, male antennal response and attraction in the field, and synthesis of the most active pheromone component. Several 3,7-dimethyl-2-alkanols were identified from female whole-body extracts, including some compounds with a 2R configuration. This is the first observation of such compounds in a pine sawfly species. Antennae of male G. pallida responded strongly in electroantennograph (EAG) recordings to the (2S,3R,7R)-isomers of the propionates of 3,7-dimethyl-2-tridecanol, 3,7-dimethyl-2-tetradecanol, and 3,7-dimethyl-2-pentadecanol, as well as to the acetates of the tri- and pentadecanols (the acetate of the tetradecanol was not tested). The propionate of (2S,3R,7R)-3,7-dimethyl-2-tetradecanol caught more males in the field than the corresponding isomer of tri- or pentadecanol. We suggest that the (2S,3R,7R)-isomer of 3,7-dimethyl-2-tetradecanol is likely the main sex pheromone precursor in G. pallida, with a subsidiary role for the (2S,3R,7R)-isomer of the tridecanol. Preparation of highly pure (2R,3R,7R)- and (2S,3R,7R)-stereoisomers of 3,7-dimethyl-2-tetradecanol, including the biological active esters, was performed via chemoenzymatic methods and is described in detail.
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4.
  • Lebreton, Sebastien, et al. (författare)
  • A Drosophila female pheromone elicits species-specific long-range attraction via an olfactory channel with dual specificity for sex and food
  • 2017
  • Ingår i: BMC Biology. - : Springer Science and Business Media LLC. - 1741-7007. ; 15:1
  • Tidskriftsartikel (refereegranskat)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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5.
  • Svensson, Glenn, et al. (författare)
  • Chemical ecology and insect conservation: optimising pheromone-based monitoring of the threatened saproxylic click beetle Elater ferrugineus
  • 2012
  • Ingår i: Journal of Insect Conservation. - : Springer Science and Business Media LLC. - 1366-638X .- 1572-9753. ; 16:4, s. 549-555
  • Tidskriftsartikel (refereegranskat)abstract
    • Elater ferrugineus is a saproxylic click beetle inhabiting old deciduous trees in Europe. It is threatened throughout its area of distribution due to habitat loss. No efficient monitoring method has been available for this species, but observed attraction of females to (R)-(+)-γ-decalactone, which is a male-produced sex pheromone of its prey, the scarab beetle Osmoderma eremita, has led to the development of an odour lure for monitoring. In addition, four esters have recently been identified from the pheromone-producing gland in female E. ferrugineus, and a blend of these esters is highly attractive to conspecific males in the field, revealing an alternative odour-based method for monitoring this species. However, no rigorous analysis has been performed to check whether all four esters show biological activity in male E. ferrugineus, and whether its own sex pheromone is a more potent lure than the prey kairomone for monitoring of E. ferrugineus. In this study, we reinvestigated the E. ferrugineus sex pheromone, using electrophysiological and behavioural analyses, and found that only one of the esters, 7-methyloctyl (Z)-4-decenoate, is active. In addition, trapping experiments revealed that 7-methyloctyl (Z)-4-decenoate is a much more efficient attractant for male E. ferrugineus than the prey pheromone is for conspecific females, or any sex of O. eremita. With a very efficient odour lure at hand, novel information about current distribution, local population sizes, and dispersal ranges in E. ferrugineus can now be obtained, which can aid in conservation efforts to protect this threatened insect and its habitat.
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6.
  • Harvey, Deborah J., et al. (författare)
  • Making the invisible visible : Determining an accurate national distribution of Elater ferrugineus in the United Kingdom using pheromones
  • 2017
  • Ingår i: Insect Conservation and Diversity. - : Wiley. - 1752-458X .- 1752-4598. ; 10:4, s. 1-11
  • Tidskriftsartikel (refereegranskat)abstract
    • To date, conservation-status saproxylic beetle species in the UK have been monitored by chance findings or by monitor-based observational studies. Here, using Elater ferrugineus as our target species, we present the first national distribution survey carried out in the UK or across mainland Europe on such a species using chemicals produced by the insect. Over 3 years, mark-release-recapture studies were performed across the UK, using 416 lured (pheromone) traps monitored by volunteer recorders; the first survey in Europe to do so. Traps were baited with 7-methyloctyl- (Z)-4-decenoate, a compound previously identified as a female sex pheromone. The results were used to plot a distribution map and investigate factors that may influence the distribution, including summer temperatures, possible habitat availability and larval food source. The survey revealed a south-eastern distribution of E. ferrugineus in the UK, which was suggested by previous casual studies. A correlative model was fitted to the data, indicating that 55% of the variation in the distribution of E. ferrugineus was explained by climatic variables (temperature and wind speed).
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7.
  • Liedtke, H. Christoph, et al. (författare)
  • Alarm pheromones and chemical communication in nymphs of the tropical bed bug Cimex hemipterus (Hemiptera: Cimicidae)
  • 2011
  • Ingår i: PLOS ONE. - : Public Library of Science (PLoS). - 1932-6203. ; 6:3, s. e18156-
  • Tidskriftsartikel (refereegranskat)abstract
    • 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.
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8.
  • Rahmani, Rizan, et al. (författare)
  • Identification and synthesis of putative pheromone components of the threatened salt marsh bagworm moth, Whittleia retiella (Lepidoptera: Psychidae)
  • 2020
  • Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 46, s. 115-127
  • Tidskriftsartikel (refereegranskat)abstract
    • Whittleia retiella (Newman, 1847) is a threatened salt marsh species of the bagworm moth family Psychidae. For its preservation it is necessary to develop efficient tools to survey its distribution and habitat requirements in order to use appropriate conservation methods. Such tools may be pheromone-based monitoring systems, which have documented efficacy in establishing the occurrence of cryptic insect species in nature. By using gas chromatography combined with electroantennographic detection (GC-EAD), we found two compounds in female W. retiella headspace samples and whole-body extracts that elicited electrophysiological activity in male antennae. Gas chromatograpy coupled with mass spectrometry (GC-MS) operating in electron impact (EI) mode and comparison of the analytical data with those of synthetic reference compounds showed the chemical structures of these putative pheromone components to be (1S)-1-methylpropyl (5Z)-dec-5-enoate and 1-methylethyl (5Z)-dec-5-enoate. Field assays using baits loaded with synthetic compounds revealed that conspecific males were attracted to (1S)-1-methylpropyl (5Z)-dec-5-enoate alone or in combination with 1-methylethyl (5Z)-dec-5-enoate, whereas 1-methylethyl (5Z)-dec-5-enoate neither attracted nor repelled males in the field assays when tested alone. This study shows the potential of using (1S)-1-methylpropyl (5Z)-dec-5-enoate for monitoring W. retiella to gather more detailed information about the geographic distribution and habitat needs of this rare moth.
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9.
  • Frey, T., et al. (författare)
  • The human odorant receptor OR10A6 is tuned to the pheromone of the commensal fruit fly Drosophila melanogaster
  • 2022
  • Ingår i: iScience. - : Elsevier BV. - 2589-0042. ; 25:11
  • Tidskriftsartikel (refereegranskat)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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10.
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