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  • 1.
    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. 

  • 2.
    Pokorny, T.
    et al.
    Institute of Sensory Ecology, Heinrich-Department of Animal Ecology, Evolution and Biodiversity, Ruhr University Bochum, 44780 Bochum, Germany .
    Hannibal, M.
    Institute of Sensory Ecology, Heinrich-Heine University Düsseldorf, 40225 Düsseldorf, Germany .
    Quezada-Euan, J. J. G.
    Departamento de Apicultura, Universidad Autónoma de Yucatán, Mérida, Yucatán, 97100, Mexico .
    Hedenström, Erik
    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.
    Bång, Joakim
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Eltz, T.
    Department of Animal Ecology, Evolution and Biodiversity, Ruhr University Bochum, 44780 Bochum, Germany .
    Acquisition of species-specific perfume blends: Influence of habitat-dependent compound availability on odour choices of male orchid bees (Euglossa spp.)2013In: Oecologia, ISSN 0029-8549, E-ISSN 1432-1939, Vol. 172, no 2, p. 417-425Article in journal (Refereed)
    Abstract [en]

    Male orchid bees (Euglossini, Apidae, Hymenoptera) expose species-specific blends of volatile chemicals (perfume bouquets) during their courtship display. The perfumes are acquired by collecting fragrant substances from environmental sources, which are then accumulated in specialised hind leg pouches. To balance the perfume composition, the males need to find and collect the required substances in specific relative amounts while facing seasonal, local or habitat-dependent differences in compound availability. Experience-dependent choice of odours, i.e. 'learned avoidance' of recently collected components, has been proposed as the mechanism that mediates the accumulation of the stereotypical compound ratios. In the present study, we used the presence of certain compounds in male hind leg pouches as proxy for the respective local compound availability, and investigated whether differences in content are correlated with differences in chemical choice assays. Our results suggest that volatile availability differs between localities (n = 16) as well as habitats (n = 2; coastal vs. inland) across the Yucatán peninsula, Mexico, for both studied species. Male Euglossa dilemma showed a pronounced preference for benzyl benzoate and eugenol at locations where those compounds were rare in hind leg extracts, as predicted by the learned avoidance model. No equivalent correlations were found for Euglossa viridissima. This is the first study to combine chemical analyses of perfumes with bioassays of odour choice. It strengthens the view that negative feedback from collected odours modifies future chemical choice and helps males to acquire specific perfume blends. © 2013 Springer-Verlag Berlin Heidelberg.

  • 3.
    Sjöberg, Natalia
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    (S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylationManuscript (preprint) (Other academic)
    Abstract [en]

    A novel chiral auxiliary (S)-2-(1,2,3,4-tetrahydroisoquinolin-3-yl)propan-2-ol 1 was synthesized from (S)-1,2,3,4-tetrahydroisoquinoline acid 2. Alkylation of the propanoylated chiral auxiliary (S)-1-(3-(2-hydroxypropan-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)-propan-1-one 3 with benzyl bromide or n-butyl iodide caused moderate to high conversion (42–99%) and moderate diastereomeric ratios (up to 89:11). The major diastereomer obtained in the reaction with benzyl bromide was (R,S). Some of the reactions were carried out with LiCl as an enolate coordinating agent, which affected conversion and diastereomeric ratio negatively. 

  • 4.
    Sjöberg, Natalia
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Structure determination and synthesis of natural extracts. (S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylation: Licentiate thesisManuscript (preprint) (Other academic)
  • 5.
    Svensson, G. P.
    et al.
    Department of Biology, Lund University, 223 62 Lund, Sweden .
    Gündüz, E. A.
    Department of Biology, Ondokuz Mayis University, Kurupelit, 55139 Samsun, Turkey .
    Sjöberg, Natalia
    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.
    Lassance, J. -M
    Department of Biology, Lund University, 223 62 Lund, Sweden .
    Wang, H. -L
    Department of Biology, Lund University, 223 62 Lund, Sweden .
    Löfstedt, C.
    Department of Biology, Lund University, 223 62 Lund, Sweden .
    Anderbrant, O.
    Department of Biology, Lund University, 223 62 Lund, Sweden .
    Identification, Synthesis, and Behavioral Activity of 5,11-Dimethylpentacosane, A Novel Sex Pheromone Component of the Greater Wax Moth, Galleria Mellonella (L.)2014In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 40, no 4, p. 387-395Article in journal (Refereed)
    Abstract [en]

    The greater wax moth, Galleria mellonella (L.), is a serious and widespread pest of the honeybee, Apis mellifera L. In contrast to most moths, for which long-range mate finding is mediated by female-produced sex pheromones, G. mellonella males attract conspecific females over long distances by emitting large amounts of a characteristic scent in combination with bursts of ultrasonic calls. The male scent for this species was previously identified as a blend of nonanal and undecanal. When these compounds were bioassayed, characteristic short-range sexual behavior, including wing fanning, was triggered in conspecific females, but the aldehyde blend failed to elicit attraction over longer distances. We identified, via analysis and synthesis, a third male-specific compound, 5,11-dimethylpentacosane. We show that it acts as a behavioral synergist to the aldehydes. In wind tunnel experiments, very few female moths responded to the aldehyde blend or to 5,11-dimethylpentacosane tested separately, but consistently showed orientation and source contact when a combination of all three compounds was applied. The level of attraction to the three-component mixture was still lower than that to male extract, indicating that the composition of compounds in the synthetic blend is suboptimal, or that additional pheromone components of G. mellonella are yet to be identified. The identification of 5,11-dimethylpentacosane is an important step for the development of an efficient long-range attractant that will be integrated with other environmentally safe strategies to reduce damage to beehives caused by wax moths. © 2014 Springer Science+Business Media New York.

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