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Rahmani, R., Wallin, E., Viklund, L., Schroeder, M. & Hedenström, E. (2019). Identification and Field Assay of Two Aggregation Pheromone Components Emitted by Males of the Bark Beetle Polygraphus punctifrons (Coleoptera: Curculionidae). Journal of Chemical Ecology, 45(4), 356-365
Open this publication in new window or tab >>Identification and Field Assay of Two Aggregation Pheromone Components Emitted by Males of the Bark Beetle Polygraphus punctifrons (Coleoptera: Curculionidae)
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2019 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 45, no 4, p. 356-365Article in journal (Refereed) Published
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. 

Keywords
(+)-(1R, 2S)-Grandisol, (−)-(R)-Terpinen-4-ol, Enantiomeric separation, Picea abies, Preparative fraction collection, SPME
National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-35836 (URN)10.1007/s10886-019-01056-6 (DOI)000467745400003 ()30796678 (PubMedID)2-s2.0-85061967619 (Scopus ID)
Available from: 2019-03-20 Created: 2019-03-20 Last updated: 2019-08-14Bibliographically approved
Rahmani, R., Andersson, F., Andersson, M. N., Yuvaraj, J. K., Anderbrant, O. & Hedenström, E. (2019). Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Forster). Chemoecology, 29(3), 103-110
Open this publication in new window or tab >>Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Forster)
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2019 (English)In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 29, no 3, p. 103-110Article in journal (Refereed) Published
Abstract [en]

The Carrot psyllid, Trioza apicalis Forster (Homoptera: Psylloidea: Triozidae) is one of the major insect pests of carrots (Daucus carota L.) in parts of northern and central Europe. Gas chromatography-single-sensillum recording (GC-SSR) previously confirmed several active compounds in a carrot leaf extract, but the most active compound remained unidentified. Mass fragmentation patterns observed from the unidentified active compound when analyzed by gas chromatography and mass spectrometry (GC-MS) was used to propose -sesquiphellandrene and -cis-bergamotene to be candidates as the unidentified compound. The compounds were synthesized and their mass spectra were nearly identical with the unknown active compound. But, the retention times differed from the compound in the carrot leaf extract. Thus, to obtain the unidentified compound pure enough and in adequate amounts for nuclear magnetic resonance (NMR) analysis, preparative gas chromatography was applied to separate and concentrate this biologically active compound. Analysis by liquid chromatography quadrupole time of flight mass spectrometry (LC-QTOF) confirmed the unidentified compound to be a compound with theformula of C15H24 and together with GC-MS, H-1 and C-13 NMR analysis sesquisabinene B was identified as the unidentified compound in the extract. GC-SSR was then used to finally confirm the biological activity of sesquisabinene B isolated from the carrot leaf extract via preparative GC.

Keywords
Synthesis, beta-Sesquiphellandrene, alpha-cis-Bergamotene, Preparative gas chromatography, Single-sensillum recording, Analysis
National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-36651 (URN)10.1007/s00049-019-00280-6 (DOI)000469799200002 ()
Available from: 2019-07-08 Created: 2019-07-08 Last updated: 2019-08-14Bibliographically approved
Viklund, L., Rahmani, R., Bång, J., Schroeder, M. & Hedenström, E. (2019). Optimizing the attractiveness of pheromone baits used for trapping the four-eyed spruce bark beetle Polygraphus poligraphus. Journal of applied entomology, 143(7), 721-730
Open this publication in new window or tab >>Optimizing the attractiveness of pheromone baits used for trapping the four-eyed spruce bark beetle Polygraphus poligraphus
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2019 (English)In: Journal of applied entomology, ISSN 0931-2048, E-ISSN 1439-0418, Vol. 143, no 7, p. 721-730Article in journal (Refereed) Published
Abstract [en]

Bark beetles have caused extensive damage to forests in central Sweden during the past decade, and the four-eyed spruce bark beetle, Polygraphus poligraphus, seems to be involved. However, its role in these bark beetle outbreaks is still not clear. The purpose of this study was to develop an efficient pheromone bait for P. poligraphus, which would make it possible to study the species more carefully and thereby contribute to protect exposed forests in an environmentally friendly way. Three field studies were conducted in 2015, 2016 and 2018 in Medelpad, county of Västernorrland, Sweden. The pheromone of P. poligraphus, (−)-terpinen-4-ol, was tested at different release rates and in different enantiomeric purities, to find the most attractive formulation for the beetles. It was also tested in combination with racemic frontalin, a compound which has previously been shown to produce a synergistic effect together with (−)-terpinen-4-ol of low enantiomeric purity; 52% ee. Other compounds, chosen based on responses from electroantennographic studies, were also tested in an attempt to find additional attractants and repellents for P. poligraphus. The most attractive treatment tested was enantiomerically pure (−)-terpinen-4-ol (99% ee). When the enantiomeric purity was lower (50% ee), the trap catches was lowered to levels comparable to the catches for unbaited control traps. A strong synergistic effect with frontalin was observed for (−)-terpinen-4-ol of low enantiomeric purity (50% ee) but not for the enantiomerically pure compound (99% ee). The release rate of (−)-terpinen-4-ol (99% ee) was shown to be an important factor. For the combination of frontalin and (−)-terpinen-4-ol (50% ee), the attraction seemed strongest when (−)-terpinen-4-ol was released at a higher rate than frontalin. An interesting and novel result was that a repellent compound, α-terpineol, was identified in our studies. Our results from field studies and electroantennography recordings also indicate that (+)-terpinen-4-ol is a repellent for P. poligraphus.

Keywords
enantiomers, field study, frontalin, pheromone, synergism, terpinen‐4‐ol
Identifiers
urn:nbn:se:miun:diva-36659 (URN)10.1111/jen.12641 (DOI)000475465300003 ()
Available from: 2019-07-08 Created: 2019-07-08 Last updated: 2019-08-14Bibliographically approved
Hedenström, E., Andersson, F., Sjöberg, N. & Eltz, T. (2018). 6-(4-Methylpent-3-en-1-yl)naphthalene-1,4-dione, a behaviorally active semivolatile in tibial perfumes of orchid bees. Chemoecology, 28(4-5), 131-135
Open this publication in new window or tab >>6-(4-Methylpent-3-en-1-yl)naphthalene-1,4-dione, a behaviorally active semivolatile in tibial perfumes of orchid bees
2018 (English)In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 28, no 4-5, p. 131-135Article in journal (Refereed) Published
Abstract [en]

Male neotropical orchid bees (Euglossini) collect volatiles from varied sources in their environment to compile complex, species-specific tibial perfumes, which are later released at mating sites. A major compound prominent in tibial extracts of Euglossa allosticta was purified, as well as isolated and its structure was elucidated by analytical methods including GC–MS, GC–FTIR, HRMS and 1H and 13C NMR. After synthesis, the compound with the proposed structure was finally identified as 6-(4-methylpent-3-en-1-yl)naphthalene-1,4-dione. At field sites in Panama and Costa Rica, the synthetic compound attracted males of E. allosticta, but no other euglossines. This strengthens the view that semivolatiles play an important role in conveying specificity to perfume signals of orchid bees. 

National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-34598 (URN)10.1007/s00049-018-0264-6 (DOI)000446684800003 ()2-s2.0-85052937823 (Scopus ID)
Available from: 2018-10-03 Created: 2018-10-03 Last updated: 2019-03-15Bibliographically approved
Rönnander, J., Ljunggren, J., Hedenström, E. & Wright, S. A. (2018). Biotransformation of vanillin into vanillyl alcohol by a novel strain of Cystobasidium laryngis isolated from decaying wood. AMB Express, 8(1), Article ID 137.
Open this publication in new window or tab >>Biotransformation of vanillin into vanillyl alcohol by a novel strain of Cystobasidium laryngis isolated from decaying wood
2018 (English)In: AMB Express, ISSN 2191-0855, E-ISSN 2191-0855, Vol. 8, no 1, article id 137Article in journal (Refereed) Published
Abstract [en]

Vanillin is an aromatic aldehyde found as a component of lignocellulosic material, and in the cured pods of orchidaceae plants. Like other phenolic substances, vanillin has antimicrobial activity and can be extracted from lignin either by a thermo-chemical process or through microbial degradation. Vanillin, can serve as a model monomer in biodegradation studies of lignin. In the present study, a yeast isolated from decaying wood on the Faroe Islands, was identified as Cystobasidium laryngis strain FMYD002, based on internal transcribed spacer sequence analysis. It demonstrated the ability to convert vanillin to vanillyl alcohol, as detected by ultra-high performance liquid chromatography-quadrupole-time-of-flight. Structural analysis of vanillyl alcohol was carried out by using gas chromatography-mass spectrometry and H-1 NMR spectroscopy, and further verified by synthesis. The reduction of vanillin to vanillyl alcohol has been documented for only a few species of fungi. However, to our knowledge, this biotransformation has not yet been reported for basidiomycetous yeast species, nor for any representative of the subphylum Pucciniomycotina. The biotransformation capability of the present strain might prove useful in the industrial utilisation of lignocellulosic residues.

Keywords
Vanillin, Cystobasidium, Bioconversion, Biodegradation, Cystobasidiomycetes, Rhodotorula
National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-34517 (URN)10.1186/s13568-018-0666-4 (DOI)000442555800002 ()30143905 (PubMedID)2-s2.0-85052069822 (Scopus ID)
Available from: 2018-09-26 Created: 2018-09-26 Last updated: 2018-10-01Bibliographically approved
Becher, P. G., Lebreton, S., Wallin, E., Hedenström, E., Borrero, F., Bengtsson, M., . . . Witzgall, P. (2018). The Scent of the Fly. Journal of Chemical Ecology, 44(5), 431-435
Open this publication in new window or tab >>The Scent of the Fly
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2018 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 44, no 5, p. 431-435Article in journal (Refereed) Published
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. 

Keywords
Drosophila melanogaster, Odorant, Off-flavour, Olfaction, Pheromone, Semiochemical, Wine
National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-33632 (URN)10.1007/s10886-018-0950-4 (DOI)000431113700001 ()29611073 (PubMedID)2-s2.0-85044769966 (Scopus ID)
Available from: 2018-05-15 Created: 2018-05-15 Last updated: 2019-08-06Bibliographically approved
Lebreton, S., Borrer-Echeverry, F., Gonzalez, F., Solum, M., Wallin, E., Hedenström, E., . . . Witzgall, P. (2017). A Drosophila female pheromone elicits species-specific long-range attraction via an olfactory channel with dual specificity for sex and food. BMC Biology, 15(1), Article ID 88.
Open this publication in new window or tab >>A Drosophila female pheromone elicits species-specific long-range attraction via an olfactory channel with dual specificity for sex and food
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2017 (English)In: BMC Biology, ISSN 1741-7007, E-ISSN 1741-7007, Vol. 15, no 1, article id 88Article in journal (Refereed) Published
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.

Keywords
Chemical ecology, Olfaction, Reproductive isolation, Sexual communication
National Category
Chemical Sciences Biological Sciences
Identifiers
urn:nbn:se:miun:diva-32213 (URN)10.1186/s12915-017-0427-x (DOI)000412075400001 ()28962619 (PubMedID)2-s2.0-85030159502 (Scopus ID)
Available from: 2017-12-04 Created: 2017-12-04 Last updated: 2017-12-18Bibliographically approved
Harvey, D. J., Harvey, H., Larsson, M. C., Svensson, G. P., Hedenström, E., Finch, P. & Gange, A. C. (2017). Making the invisible visible: Determining an accurate national distribution of Elater ferrugineus in the United Kingdom using pheromones. Insect Conservation and Diversity, 10(4), 1-11
Open this publication in new window or tab >>Making the invisible visible: Determining an accurate national distribution of Elater ferrugineus in the United Kingdom using pheromones
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2017 (English)In: Insect Conservation and Diversity, ISSN 1752-458X, E-ISSN 1752-4598, Vol. 10, no 4, p. 1-11Article in journal (Refereed) Published
Abstract [en]

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).

Keywords
Aerial traps, Elater ferrugineus, National distribution, Pheromone, Saproxylic, Veteran trees
National Category
Biological Sciences
Identifiers
urn:nbn:se:miun:diva-31108 (URN)10.1111/icad.12227 (DOI)000404622500001 ()2-s2.0-85017335374 (Scopus ID)
Note

Version of record online: 5 April 2017

Available from: 2017-07-03 Created: 2017-07-03 Last updated: 2018-03-01Bibliographically approved
Harvey, D. J., Harvey, H., Harvey, R. P., Kadej, M., Hedenström, E., Gange, A. C. & Finch, P. (2017). Use of novel attraction compounds increases monitoring success of a rare beetle, Elater ferrugineus. Insect Conservation and Diversity, 10(2), 161-170
Open this publication in new window or tab >>Use of novel attraction compounds increases monitoring success of a rare beetle, Elater ferrugineus
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2017 (English)In: Insect Conservation and Diversity, ISSN 1752-458X, E-ISSN 1752-4598, Vol. 10, no 2, p. 161-170Article in journal (Refereed) Published
Abstract [en]

The use of pheromones to determine distributions of rare saproxylic insects is an increasingly popular technique. Pheromones may, however, also be used to elucidate the biology of these cryptic species, a vital requirement if they are to be accurately monitored and conserved. We used non-invasive aerial trapping to compare the effectiveness of chemicals produced by Elater ferrugineus L (Coleoptera: Elateridae), namely 7-methyloctyl (Z)-4-decenoate (the female-produced sex pheromone), and male compounds (geranyl and neryl acetone and 6-methyl-5-heptene-2-one). The male compounds were identified using headspace analysis by solid phase micro-extraction gas chromatography-mass spectrometry. We discovered that males only produce these two compounds after having been attracted to a female, and that this serves to attract further males to a female. Such compounds do not appear to attract females but for a species that has a short activity period and is non-feeding in the adult stage, may ensure breeding success when populations are low. By marking all beetles caught, we were able to demonstrate that recapture rate using this method is low (approximately 11% of total captures annually). Therefore, the method does not limit dispersal or breeding opportunities, making it a valuable tool for monitoring endangered saproxylic beetle species.

Keywords
Aggregation, allee effect, Elater ferrugineus, monitoring, pheromones, polyandry, saproxylic
National Category
Chemical Sciences Biological Sciences
Identifiers
urn:nbn:se:miun:diva-30645 (URN)10.1111/icad.12214 (DOI)000395384800006 ()2-s2.0-85008199825 (Scopus ID)
Available from: 2017-04-21 Created: 2017-04-21 Last updated: 2017-07-04Bibliographically approved
Zauli, A., Carpaneto, G. M., Chiari, S., Mancini, E., Nyabuga, F. N., De Zan, L. R., . . . Svensson, G. P. (2016). Assessing the taxonomic status of Osmoderma cristinae (Coleoptera Scarabaeidae), endemic to Sicily, by genetic, morphological and pheromonal analyses. Journal of Zoological Systematics and Evolutionary Research, 54(3), 206-214
Open this publication in new window or tab >>Assessing the taxonomic status of Osmoderma cristinae (Coleoptera Scarabaeidae), endemic to Sicily, by genetic, morphological and pheromonal analyses
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2016 (English)In: Journal of Zoological Systematics and Evolutionary Research, ISSN 0947-5745, E-ISSN 1439-0469, Vol. 54, no 3, p. 206-214Article in journal (Refereed) Published
Abstract [en]

Resolving complexes of closely related and cryptic insect species can be challenging, especially when dealing with rare and protected taxa that are difficult to collect for genetic and morphological analyses. Until recently, populations of the genus Osmoderma (Scarabaeidae), widespread in Europe, were treated as a single species O.eremita (Scopoli, 1763) in spite of observed geographic variation in morphology. A previous survey using sequence data from the mtDNA cytochrome C oxidase I gene (COI) revealed the occurrence of at least two distinct lineages within this species complex: O.eremita in the west and O.barnabita Motschulsky, 1845, in the east. Interestingly, beetles confined to Sicily have been described as a distinct species, O.cristinae Sparacio, 1994, based on morphological traits. Only few Sicilian specimens were included in the former genetic analysis, and the results led to a still questionable taxonomic rank for these populations. To explore the robustness of the previous taxonomic arrangement for O.cristinae, a combination of genetic, morphological and pheromonal analyses was used. A 617-bp fragment of the COI gene, aligned with O.cristinae and O.eremita sequences already available in GenBank, showed a clear genetic divergence between the two species (interspecific mean distance=6.6%). Moreover, results from AFLP markers sustained the distinction of the two species. In addition, geometric morphometric analyses of the shape of male genitalia revealed a clear differentiation between the two species. Via scent analysis and field trapping, we demonstrated the production of the sex pheromone (R)-(+)--decalactone by males of O.cristinae, the attraction by conspecific individuals (mostly females) to this compound, and a lack of antagonistic effect of (S)-(-)--decalactone. The fact that O.eremita and O.eremita use the same compound for mate finding suggests that this sex pheromone has not undergone a differentiation and probably the allopatry of these two species compensates for the absence of a mechanism to avoid cross-attraction. Our genetic and morphological data support the divergence of the two species and confirm the species status for O.cristinae, while sex pheromones are confirmed to be invariant among different species of the genus Osmoderma.

National Category
Natural Sciences
Identifiers
urn:nbn:se:miun:diva-29499 (URN)10.1111/jzs.12127 (DOI)000379536800007 ()2-s2.0-84958682374 (Scopus ID)
Available from: 2016-12-12 Created: 2016-12-12 Last updated: 2017-05-04Bibliographically approved
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0002-5543-2041

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