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  • 1. Andersson, Fredrik
    1. Asymmetric aldol and alkylation reactions using pyrrolidine-based chiral auxiliaries 2. Syntheses of pine sawfly pheromone precursors and structurally related compounds2002Licentiate thesis, comprehensive summary (Other academic)
  • 2.
    Andersson, Fredrik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Highly stereoselective alkylation of (S)-proline-based chiral auxiliaries2004In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 15, no 16, p. 2539-2545Article in journal (Refereed)
    Abstract [en]

    Alkylation of the enolates of the propanoylamides of two chiral auxiliaries (S)-(-)-2-(pyrrolidin-2-yl)propan-2-ol 1a and (S)-(-)-2-(2-methoxypropan-2-yl)pyrrolidine 1b, derived from (S)-proline, with benzyl bromide and n-butyl iodide has been studied. The auxiliaries 1a and 1b induced opposite selectivity that is (R)- and (S)-configuration, respectively, at the newly created stereogenic centre. The diastereoselectivities and conversion yields in these alkylations were moderate to excellent. When Cp2ZrCl2 was used as an enolate coordinating agent, benzylation of propanoylated 1b gave an excellent diastereomeric ratio of 99:1. The benzylated diastereomeric products from either propanoylated 1a or 1b were easily separated by liquid chromatography.

  • 3.
    Andersson, Fredrik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Synthesis of two (S)-indoline-based chiral auxiliaries and their use in diastereoselective alkylation reactions2006In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 17, no 13, p. 1952-1957Article in journal (Refereed)
    Abstract [en]

    Two chiral auxiliaries, 2-[(S)-indolin-2-yl]propan-2-ol 1a and (S)-2-(2-methoxypropan-2-yl)indoline 1b, were synthesised from enantiomerically pure (S)-indoline-2-carboxylic acid 3. High diastereoselectivities in alkylations of enolates of the propanoylamides derived from the two auxiliaries are presented. Surprisingly, both auxiliaries induced the same selectivity at the newly created stereogenic centre. The benzyl bromide and n-butyl iodide alkylation reactions showed diastereomeric ratios that were moderate (81:19) to very good (96:4) and with very good yields (86-98%). When LiCl was used as an enolate coordinating agent, in the benzylation of the enolate from propanoylated auxiliary 1a, a very high crude diastereomeric ratio was obtained (99.7:0.3).

  • 4.
    Andersson, K.
    et al.
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Box 102, SE-23053 Alnarp, Sweden.
    Bergman, K. -O
    IFM Biology, Conservation Ecology Group, Linköping University, SE-58183 Linköping, Sweden.
    Andersson, Fredrik
    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.
    Jansson, N.
    IFM Biology, Conservation Ecology Group, Linköping University, SE-58183 Linköping, Sweden.
    Burman, J.
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Box 102, SE-23053 Alnarp, Sweden.
    Winde, I.
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Box 102, SE-23053 Alnarp, Sweden.
    Larsson, M. C.
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Box 102, SE-23053 Alnarp, Sweden.
    Milberg, P.
    IFM Biology, Conservation Ecology Group, Linköping University, SE-58183 Linköping, Sweden.
    High-accuracy sampling of saproxylic diversity indicators at regional scales with pheromones: The case of Elater ferrugineus (Coleoptera, Elateridae)2014In: Biological Conservation, ISSN 0006-3207, E-ISSN 1873-2917, Vol. 171, p. 156-166Article in journal (Refereed)
    Abstract [en]

    The rare beetle Elater ferrugineus was sampled at 47 sites in the county of Östergötland, Sweden by means of pheromone-baited traps to assess its value as an indicator species for hollow oak stands rich in rare saproxylic beetle species. In addition, Osmoderma eremita was also sampled with pheromone baits. These data were then compared against species survey data collected at the same sites by pitfall and window traps. Both species co-occur with many Red Listed saproxylic beetles, with E. ferrugineus being a somewhat better indicator for the rarest species. The conservation value of a site (measured as Red List points or number of Red Listed species) increased with the number of specimens of E. ferrugineus and O. eremita caught. Accuracy of sampling by means of pheromone trapping turned out to be radically different for the two model species. E. ferrugineus traps put out during July obtained full accuracy after only 6. days, whereas O. eremita traps needed to be out from early July to mid-August in order to obtain full accuracy with one trap per site. By using E. ferrugineus, or preferably both species, as indicator species, accuracy would increase and costs decrease for saproxylic biodiversity sampling, monitoring and identification of hotspots. © 2014 Elsevier Ltd.

  • 5.
    Hedenström, Erik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Andersson, Fredrik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Syntheses of female sex pheromone precursors of pine sawflies species and of some structurally related methyl-branched long-chain 2-alkanols2002In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 28, no 6, p. 1237-1254Article in journal (Refereed)
    Abstract [en]

    3,7-Dimethyl-2-undecanol, 3,7,9-trimethyl-2-tridecanol, and 3,7, 11-trimethyl-2-tridecanol were synthesized as racemic mixtures in moderate yields. The alcohols are known precursors of the female sex pheromones of the pine sawfly species Diprion nipponica, Macrodiprion nemoralis, and Microdiprion pallipes, respectively. Stereoisomeric mixtures of 3,8,12-trimethyl-2-tridecanol, erythro-(2R,3R,11R/S)-3,11-dimethyl-2-tetradecanol, 3,5-dimethyl-2-tetradecanol, and 5,7-dimethyl-2-tetradecanol, structurally related to sex pheromone alcohol precursors of pine sawfly species, were also synthesized in moderate yields. The key reaction in the syntheses was the ring opening of γ-butyrolactones by using different alkyl lithiums as nucleophiles.

  • 6.
    Hedenström, Erik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Andersson, Fredrik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hjalmarsson, Mats
    Synthesis of N-propionylated (S)-(-)-2-(pyrrolidin-2-yl)propan-2-ol and its use as a chiral auxiliary and selectivity marker in asymmetric aldol reactions2000In: Journal of the Chemical Society. Perkin Transactions 1, ISSN 1472-7781, Vol. 2000, p. 1513-1518Article in journal (Refereed)
    Abstract [en]

    The N-propionylated pyrrolidine derivative and chiral auxiliary, (S)-(-)-2-(pyrrolidin-2-yl)propan-2-ol, was synthesised and used in stereoselective aldol reactions with benzaldehyde. Differences in stereoselectivity were investigated as a function of temperature, solvent, chelating agent and the amount of the chelating agent used by monitoring the 1H NMR spectra of the aldol adducts that were obtained. Among the additives that were investigated, Cp2ZrCl2 induced higher syn-selectivity, while SnCl2 induced higher syn-selectivity respectively. TMSCl was found to induce high selectivity for one syn- and one anti-diastereomer. Varying the ligand sets on titanium additives was found to induce differences in selectivity, with (i-PrO)3TiCl exhibiting syn-selectivity and Cp2TiCl2 exhibiting anti-selectivity. Differences in reactivity and stereoselectivity were also found to depend upon the amount of Lewis acid that was added. Methods for removal of the auxiliary were also investigated. Acidic hydrolysis was used successfully to obtain the desired 3-hydroxy-2-methyl-3-phenylpropionic acids, but was found to give low yields and resulted in a large amount of epimerisation. Furthermore, the ethyl esters of these hydroxy acids are easy to separate into pure syn- and anti-diastereomers by LC. © The Royal Society of Chemistry 2000.

  • 7.
    Hedenström, Erik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Andersson, Fredrik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Sjöberg, Natalia
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Eltz, Thomas
    Ruhr University Bochum, Bochum, Germany.
    6-(4-Methylpent-3-en-1-yl)naphthalene-1,4-dione, a behaviorally active semivolatile in tibial perfumes of orchid bees2018In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 28, no 4-5, p. 131-135Article in journal (Refereed)
    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. 

  • 8.
    Högberg, Ida
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Andersson, Fredrik
    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.
    Norgren, Magnus
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Edlund, Håkan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    The Interaction Parameter in Binary Surfactant Mixtures of a Chelating Surfactant and a Foaming Agent.2010In: TRENDS IN COLLOID AND INTERFACE SCIENCE XXIV, Berlin: Springer, 2010, 138, p. 17-20Conference paper (Refereed)
    Abstract [en]

    The micellisation in binary mixed surfactant systems of a chelating surfactant and a foaming agent has been studied by surface tension measurements in order to calculate the interaction parameter (beta). 2-dodecyldiethylenetriamine pentaacetic acid, 4-C(12)-DTPA, is an amphoteric chelating surfactant applicable for removing disturbing metal ions from industrial processes, or for heavy metal decontamination of soil or leachate. 4-C(12)-DTPA contains multiple donor atoms and forms very stable coordination complexes with metal ions. The metal complexes can easily be recovered from water by flotation, if the foaming is enhanced by a foaming agent with strong interactions to the chelating surfactant. Two foaming agents were examined, one cationic and one anionic. As expected, strong interactions were found between the negatively charged 4-C(12)-DTPA and the cationic dodecyltrimethylammonium chloride, DTAC. The influence of metal ion chelation, as well as pH, on the interaction parameter was also investigated.

  • 9.
    Högberg, Ida
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Zasadowski, Dariusz
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Karlsson, Anette
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Wikman, Bengt
    SCA Rand D Centre, Box 716, SE-851 21 Sundsvall, Sweden.
    Andersson, Fredrik
    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.
    Edlund, Håkan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Norgren, Magnus
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Brightness development of a hydrogen peroxide bleached spruce TMP. Comparisons of pre-treatments with DTPA and a separable chelating surfactant2012In: Nordic Pulp & Paper Research Journal, ISSN 0283-2631, E-ISSN 2000-0669, Vol. 27, no 1, p. 50-55Article in journal (Refereed)
    Abstract [en]

    In this investigation a new type of recoverable complexing agent (chelating surfactant) has been compared with a conventional complexing agent; diethylenetriamine pentaacetic acid (DTPA), in the metal ion sequestering of thermomechanical pulps (TMP) to be hydrogen peroxide bleached. After different degrees of washing of the pulps, bleaching experiments at different total alkali charges were performed with and without sodium silicate additions, and the ISO brightness of hand-made sheets was measured. The residual hydrogen peroxide in the bleaching liquor was also determined. No significant difference in either the brightness development or the residual hydrogen peroxide content could be detected between the pulps treated with equivalent molar ratios of the different complexing agents. Furthermore, the recovery of the chelating surfactant-manganese complexes from laboratory made white water by froth flotation was also studied. Two different foaming agents; sodium dodecyl sulphonate (SDS) and dimethyldodecylamine oxide (DDAO), were tested in the froth generation. After an addition of 160 ppm of DDAO, more than 80% of the manganese chelates could be recovered in the foam, containing 3% of the initial water mass.

  • 10.
    Högberg, Ida
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Zasadowski, Dariusz
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Karlsson, Anette
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Wikman, Bengt
    SCA R&D, Sundsvall, Sweden.
    Andersson, Fredrik
    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.
    Edlund, Håkan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Norgren, Magnus
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Use of chelating surfactants as complexing agents for removal of manganese from mechanical pulp fibres prior to hydrogen peroxide bleaching.2011In: 16th International Symposium on Wood, Fiber and Pulping Chemistry - Proceedings, ISWFPC / [ed] Wang, L.; Kuang, S.; Hou, Q.; Cao, C.;Si, C.; Zhang, H., Tianjin: China Light Industry Press , 2011, p. 682-686Conference paper (Refereed)
    Abstract [en]

    In this investigation a new type of recoverable complexing agent (chelating surfactant) has been compared with a conventional complexing agent (DTPA) in the metal ion management of thermomechanical pulps (TMP) to be hydrogen peroxide bleached. After different degrees of washing of the pulps, bleaching experiments at different total alkali charges were performed with and without sodium silicate additions, and the ISO brightness of hand-made sheets was measured. The residual hydrogen peroxide in the bleaching liquor was also determined. No significant difference in either the brightness development or the residual hydrogen peroxide content could be detected between the pulps treated with equivalent molar ratios of the different complexing agents. Furthermore, the recovery of the surfactant-manganese complexes from laboratory made white water by foam flotation was also studied. Two different foaming agents, SDS and DDAO, were tested. After an addition of 160 ppm of the latter surfactant, about 80% of the manganese chelates could be recovered in the foam, containing 3% of the initial water mass.

  • 11.
    Kadej, Marcin
    et al.
    University of Wrocław, Poland.
    Zając, Krzysztof
    University of Wrocław, Poland.
    Ruta, Rafał
    University of Wrocław, Poland.
    Gutowski, Jerzy M.
    Forest Research Institute, Poland .
    Tarnawski, Dariusz
    University of Wrocław, Poland.
    Smolis, Adrian
    University of Wrocław, Poland.
    Olbrycht, Tomasz
    University of Rzeszów, Poland.
    Malkiewicz, Adam
    University of Wrocław, Poland.
    Myśków, Ewelina
    University of Wrocław, Poland.
    Larsson, Mattias C.
    Swedish Univ Agr Sci, Dept Plant Protect Biol, S-23053 Alnarp, Sweden.
    Andersson, Fredrik
    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.
    Sex pheromones as a tool to overcome the Wallacean shortfall in conservation biology: a case of Elater ferrugineus Linnaeus, 1758 (Coleoptera: Elateridae)2015In: Journal of Insect Conservation, ISSN 1366-638X, E-ISSN 1572-9753, Vol. 19, no 1, p. 25-32Article in journal (Refereed)
    Abstract [en]

    The “Wallacean shortfall”—lack of distributional information—is one of the main problems when trying to assess the threats to and planning conservation strategies for many invertebrate species. Based on published and unpublished records since 1840, as well as on our own field survey, we attempted to estimate if and to what extent the use of pheromone traps increased the detectability of a rare, saproxylic click beetle Elater ferrugineus. The significant increase in the number of records in 2011–2013 shows that the pheromone method made it much easier to detect the occurrence of the species. Advantages of the pheromone method are that it does not disturb the habitat, can be used by non-specialists, is less costly and less time-consuming, and thus providing a useful tool for conservation research (studying biology, ecology and genetics of local populations).

  • 12.
    Karlsson, Staffan
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Andersson, Fredrik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Breistein, Palle
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Synthesis of butenolides recently isolated from marine microorganisms2007In: Tetrahedron Letters, ISSN 0040-4039, Vol. 48, no 44, p. 7878-7881Article in journal (Refereed)
  • 13.
    Lassance, J-M
    et al.
    Department of Biology, Lund University, 22362 Lund, Sweden.
    Groot, A T
    Department of Entomology, Max-Planck Institute for Chemical Ecology, 07745 Jena, Germany.
    Liénard, M A
    Department of Biology, Lund University, 22362 Lund, Sweden.
    Antony, B
    Department of Biology, Lund University, 22362 Lund, Sweden.
    Borgwardt, C
    Department of Entomology, Max-Planck Institute for Chemical Ecology, 07745 Jena, Germany.
    Andersson, Fredrik
    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.
    Heckel, D G
    Department of Entomology, Max-Planck Institute for Chemical Ecology, 07745 Jena, Germany.
    Löfstedt, C
    Department of Biology, Lund University, 22362 Lund, Sweden.
    Allelic variation in a fatty-acyl reductase gene causes divergence in moth sex pheromones2010In: Nature, ISSN 0028-0836, E-ISSN 1476-4687, Vol. 466, no 7305, p. 486-489Article in journal (Refereed)
    Abstract [en]

    Pheromone-based behaviours are crucial in animals from insects to mammals, and reproductive isolation is often based on pheromone differences. However, the genetic mechanisms by which pheromone signals change during the evolution of new species are largely unknown. In the sexual communication system of moths (Insecta: Lepidoptera), females emit a species-specific pheromone blend that attracts males over long distances. The European corn borer, Ostrinia nubilalis, consists of two sex pheromone races, Z and E, that use different ratios of the cis and trans isomers of acetate pheromone components. This subtle difference leads to strong reproductive isolation in the field between the two races, which could represent a first step in speciation. Female sex pheromone production and male behavioural response are under the control of different major genes, but the identity of these genes is unknown. Here we show that allelic variation in a fatty-acyl reductase gene essential for pheromone biosynthesis accounts for the phenotypic variation in female pheromone production, leading to race-specific signals. Both the cis and trans isomers of the pheromone precursors are produced by both races, but the precursors are differentially reduced to yield opposite ratios in the final pheromone blend as a result of the substrate specificity of the enzymes encoded by the Z and E alleles. This is the first functional characterization of a gene contributing to intraspecific behavioural reproductive isolation in moths, highlighting the importance of evolutionary diversification in a lepidopteran-specific family of reductases. Accumulation of substitutions in the coding region of a single biosynthetic enzyme can produce pheromone differences resulting in reproductive isolation, with speciation as a potential end result.

     

     

  • 14.
    Musa, Najihah
    et al.
    IFM Biology, Conservation Ecology Group, Linköping University, Linköping, Sweden .
    Andersson, Klas
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp, Sweden .
    Burman, Joseph
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp, Sweden .
    Andersson, Fredrik
    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.
    Jansson, Nicklas
    IFM Biology, Conservation Ecology Group, Linköping University, Linköping, Sweden .
    Paltto, Heidi
    IFM Biology, Conservation Ecology Group, Linköping University, Linköping, Sweden .
    Westerberg, Lars
    IFM Biology, Conservation Ecology Group, Linköping University, Linköping, Sweden .
    Winde, Inis
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp, Sweden .
    Larsson, Mattias C.
    Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Alnarp, Sweden .
    Bergman, Karl-Olof
    IFM Biology, Conservation Ecology Group, Linköping University, Linköping, Sweden .
    Milberg, Per
    IFM Biology, Conservation Ecology Group, Linköping University, Linköping, Sweden .
    Using Sex Pheromone and a Multi-Scale Approach to Predict the Distribution of a Rare Saproxylic Beetle2013In: PLoS ONE, ISSN 1932-6203, E-ISSN 1932-6203, Vol. 8, no 6, p. e66149-Article in journal (Refereed)
    Abstract [en]

    The European red click beetle, Elater ferrugineus L., is associated with wood mould in old hollow deciduous trees. As a result of severe habitat fragmentation caused by human disturbance, it is threatened throughout its distribution range. A new pheromone-based survey method, which is very efficient in detecting the species, was used in the present study to relate the occurrence of E. ferrugineus to the density of deciduous trees. The latter data were from a recently completed regional survey in SE Sweden recording >120,000 deciduous trees. The occurrence of E. ferrugineus increased with increasing amount of large hollow and large non-hollow trees in the surrounding landscape. Quercus robur (oak) was found to be the most important substrate for E. ferrugineus, whereas two groups of tree species (Carpinus betulus, Fagus sylvatica, Ulmus glabra, vs. Acer platanoides, Aesculus hippocastanum, Fraxinus excelsior, Tilia cordata) were less important but may be a complement to oak in sustaining populations of the beetle. The occurrence of E. ferrugineus was explained by the density of oaks at two different spatial scales, within the circle radii 327 m and 4658 m. In conclusion, priority should be given to oaks in conservation management of E. ferrugineus, and then to the deciduous trees in the genera listed above. Conservation planning at large spatial and temporal scales appears to be essential for long-term persistence of E. ferrugineus. We also show that occurrence models based on strategic sampling might result in pessimistic predictions. This study demonstrates how pheromone-based monitoring make insects excellent tools for sustained feedback to models for landscape conservation management.

  • 15.
    Rahmani, Rizan
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Andersson, Fredrik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Andersson, Martin N.
    Lund university, Lund.
    Yuvaraj, Jothi Kumar
    Lund university, Lund.
    Anderbrant, Olle
    Lund university, Lund.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Forster)2019In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 29, no 3, p. 103-110Article in journal (Refereed)
    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.

  • 16. Steinbauer, Martin J
    et al.
    Östrand, Fredrik
    Bellas, Tom
    Nilsson, Anna
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Andersson, Fredrik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Lacey, Michael
    Schiestl, P Florian
    Identification, synthesis and activity of sex pheromone gland components of the autumn gum moth (Lepidoptera: Geometridae), a defoliator of Eucalyptus2004In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 14, no 3-4, p. 217-223Article in journal (Refereed)
    Abstract [en]

    The autumn gum moth, Mnesampela privata (Guenee) (Lepidoptera: Geometridae), is native to Australia and can be a pest of plantation eucalypts. Field-collected and laboratory-reared female autumn gum moths were dissected to remove glands likely to contain components of the sex pheromone. Using gas chromatography (GC) and combined gas chromatography-mass spectrometry (GC-MS), three compounds were identified from female extracts, namely (3Z,6Z,9Z)-3,6,9-nonadecatriene, 1-hexadecanol and 1-octadecanol (confirmed by comparison with synthetic samples). Nonadecatriene elicited an antennal response in male autumn gum moth during gas chromatographic analyses combined with electroantennographic detection (GC-EAD). In electroantennogram (EAG) recording male M. privata antennae responded to the nonadecatriene. Nonadecatriene was synthesised via Kolbe electrolysis, starting with (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid (linolenic acid) and propanoic acid or via an alternative four-step method also starting from linolenic acid. In field trials (3Z,6Z,9Z)-3,6,9-nonadecatriene proved attractive to male moths. Thus, we conclude that (3Z,6Z,9Z)-3,6,9-nonadecatriene is a sex pheromone component of autumn gum moth. This component has been identified in extracts from other geometrids in the same subfamily, Ennominae. However, to our knowledge this is the first example where (3Z,6Z,9Z)-3,6,9-nonadecatriene has been found in females and also proved attractive to male moths when presented on its own. Our results are discussed in relation to other geometrid pheromones.

  • 17.
    Svanedal, Ida
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Andersson, Fredrik
    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.
    Norgren, Magnus
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Edlund, Håkan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Satija, Sushil K.
    NIST, Ctr Neutron Res, 100 Bur Dr,MS 6100, Gaithersburg, MD 20899 USA.
    Lindman, Björn
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering. Univ Coimbra, Dept Chem, Rua Larga, P-3004535 Coimbra, Portugal.
    Rennie, Adrian R.
    Uppsala Univ, Mat Phys, Uppsala, Sweden; Uppsala Univ, Ctr Neutron Scattering, Angstrom Lab, Uppsala, Sweden.
    Molecular Organization of an Adsorbed Layer: A Zwitterionic, pH-Sensitive Surfactant at the Air/Water Interface2016In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 32, no 42, p. 10936-10945Article in journal (Refereed)
    Abstract [en]

    Neutron and X-ray reflection measurements have been used to study the structure of the adsorbed layer of a chelating surfactant at the air/liquid interface. The chelating surfactant 2-dodecyldiethylenetriaminepentaacetic acid (C-12-DTPA) has a large headgroup containing eight donor atoms that can participate in the coordination of metal ions. The donor atoms are also titrating, resulting in an amphoteric surfactant that can adopt a number of differently charged species depending on the pH. Very strong coordination complexes are formed with metal ions, where the metal ion can be considered as part of the surfactant structure, in contrast to monovalent cations that act as regular counterions to the negative net charge. Adsorption was investigated over a large concentration interval, from well below the critical micelle concentration (cmc) to five times the cmc. The most striking result is the maximum in the surface excess found around the cmc, winch is consistent with previous indications from surface tension measurements. Adding divalent metal ions has a limited effect on the adsorption at the air/liquid interface. The reason is the coordination of the metal ion, resulting in compensating deprotonation of the complex. Small variations in the headgroup area of different metal complexes are found, correlating to the conditional stability constants. Adding sodium chloride has a significant effect on the adsorption behavior, and the results indicate that the protonation equilibrium is more important than the ionic strength effects. From combined fits of the neutron and X-ray data, a model that consists of a thick headgroup region and a relatively thin dehydrated tail region is found, and it indicates that the tails are not fully extended and that the limiting area per molecule is determined by the bulky headgroup.

  • 18.
    Svanedal, Ida
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Boija, Susanne
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Almesåker, Ann
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Persson, Gerd
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Andersson, Fredrik
    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.
    Bylund, Dan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Norgren, Magnus
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Edlund, Håkan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Metal Ion Coordination, Conditional Stability Constants and Solution Behavior of Chelating Surfactant Metal Complexes2014In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 30, no 16, p. 4605-4612Article in journal (Refereed)
    Abstract [en]

    Coordination complexes of some divalent metal ions with the DTPA (diethylenetriaminepentaacetic acid)-based chelating surfactant 2-dodecyldiethylenetriaminepentaacetic acid (4-C12-DTPA) have been examined in terms of chelation and solution behavior. The headgroup of 4-C 12-DTPA contains eight donor atoms that can participate in the coordination of a metal ion. Conditional stability constants for five transition metal complexes with 4-C12-DTPA were determined by competition measurements between 4-C12-DTPA and DTPA, using electrospray ionization mass spectrometry (ESI-MS). Small differences in the relative strength between the coordination complexes of DTPA and 4-C12-DTPA indicated that the hydrocarbon tail only affected the chelating ability of the headgroup to a limited extent. The coordination of Cu2+ ions was investigated in particular, using UV-visible spectroscopy. By constructing Job's plots, it was found that 4-C12-DTPA could coordinate up to two Cu2+ ions. Surface tension measurements and NMR diffusometry showed that the coordination of metal ions affected the solution behavior of 4-C 12-DTPA, but there were no specific trends between the studied divalent metal complexes. Generally, the effects of the metal ion coordination could be linked to the neutralization of the headgroup charge of 4-C 12-DTPA, and the resulting reduced electrostatic repulsions between adjacent surfactants in micelles and monolayers. The pH vs concentration plots, on the other hand, showed a distinct difference between 4-C12-DTPA complexes of the alkaline earth metals and the transition metals. This was explained by the difference in coordination between the two groups of metal ions, as predicted by the hard and soft acid and base (HSAB) theory.

  • 19. Walker, P W
    et al.
    Allen, G R
    Davies, N W
    Smith, J A
    Molesworth, P P
    Nilsson, Anna
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Andersson, Fredrik
    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.
    Identification, Synthesis and Field Testing of (3Z,6Z,9Z)-3,6,9-Henicosatriene, a Second Bioactive Component of the Sex Pheromone of the Autumn Gum Moth, Mnesampela privata2009In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 35, no 12, p. 1411-1422Article in journal (Refereed)
    Abstract [en]

    Abstract - The sex pheromone of Mnesampela privata, an endemic pest of Eucalyptus plantations in Australia, was previously identified as containing a single bioactive compound, (3Z,6Z,9Z)-3,6,9-nonadecatriene (C19 triene). Initial field testing of lures containing 1, 5 or 10 mg of C19 triene (>98% purity) caught no or very few male M. privata. (3Z,6Z,9Z)-3,6,9-Henicosatriene (C21 triene) was identified as an additional minor pheromone component in abdominal tip extracts of M. privata females from Tasmania. Levels of C19 and C21 trienes extracted from individual females varied greatly, but the ratio was relatively constant at 33:1. Electroantennograms (EAG) of synthetic C21 triene with male M. privata gave positive but consistently lower responses than elicited by the C19 triene. Field tests showed that the addition of 1-6% C21 triene to 1mg C19 triene significantly increased trap catch and the detection of M. privata in plantations. Traps baited with a 16:1 ratio caught significantly more moths than those baited with a ratio approximating that of females.

  • 20.
    Zasadowski, Dariusz
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Andersson, Fredrik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Edlund, Håkan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Almesåker, Ann
    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.
    Norgren, Magnus
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Removal of dissolved and colloidal substances from mechanical pulping white waters by flotation2011In: 16th International Symposium on Wood, Fiber and Pulping Chemistry - Proceedings, ISWFPC / [ed] Wang, L. et al., Tianjin: China Light Industry Press , 2011, p. 1238-1242Conference paper (Other academic)
    Abstract [en]

    Various sorts of process water, foaming agents and a new chelating surfactant have been investigated in the chemical optimization of flotation ofwaters generated at laboratory and white water from mechanical pulping. Turbidity measurements, the Orcinol method for quantitative carbohydrate analysis and total organic carbon (TOC) as well as gas chromatography (GC) of extractives, have been carried out to determine theremoval and characteristics of Dissolved and Colloidal substances (DisCo). The tests have been realized under different conditions, such as using different flotation cells, foaming agents and complexing agents at different temperatures and pH values. It was found that a reduction of thewhite water turbidity of 70% and a 50% removal of the lipophilic substances from the white water can be obtained in a single-stage flotationunit, and that the selection of suitable flotation equipment, foaming agents and solution conditions plays a very important role in the removalcapacity of the unwished substances.

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