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Sjöberg, Natalia
Publications (5 of 5) Show all publications
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
Svensson, G. P., Gündüz, E. A., Sjöberg, N., Hedenström, E., Lassance, J.-M. -., Wang, H.-L. -., . . . Anderbrant, O. (2014). Identification, Synthesis, and Behavioral Activity of 5,11-Dimethylpentacosane, A Novel Sex Pheromone Component of the Greater Wax Moth, Galleria Mellonella (L.). Journal of Chemical Ecology, 40(4), 387-395
Open this publication in new window or tab >>Identification, Synthesis, and Behavioral Activity of 5,11-Dimethylpentacosane, A Novel Sex Pheromone Component of the Greater Wax Moth, Galleria Mellonella (L.)
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2014 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 40, no 4, p. 387-395Article in journal (Refereed) Published
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.

Keywords
5, 11-dimethylpentacosane, Behavior, Electrophysiology, Galleria mellonella, Honeybee pest, Lepidoptera, Male pheromone, Synthesis
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-22062 (URN)10.1007/s10886-014-0410-8 (DOI)000335656800018 ()2-s2.0-84899912959 (Scopus ID)
Note

Language of Original Document: English

Available from: 2014-05-30 Created: 2014-05-30 Last updated: 2017-12-05Bibliographically approved
Pokorny, T., Hannibal, M., Quezada-Euan, J. J., Hedenström, E., Sjöberg, N., Bång, J. & Eltz, T. (2013). Acquisition of species-specific perfume blends: Influence of habitat-dependent compound availability on odour choices of male orchid bees (Euglossa spp.). Oecologia, 172(2), 417-425
Open this publication in new window or tab >>Acquisition of species-specific perfume blends: Influence of habitat-dependent compound availability on odour choices of male orchid bees (Euglossa spp.)
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2013 (English)In: Oecologia, ISSN 0029-8549, E-ISSN 1432-1939, Vol. 172, no 2, p. 417-425Article in journal (Refereed) Published
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.

Keywords
Chemical preference, Euglossini, Hind-tibial bouquet, Learned avoidance, Pheromone analogue
National Category
Analytical Chemistry
Identifiers
urn:nbn:se:miun:diva-19360 (URN)10.1007/s00442-013-2620-0 (DOI)000319077100011 ()2-s2.0-84878110863 (Scopus ID)
Available from: 2013-09-06 Created: 2013-06-19 Last updated: 2017-12-06Bibliographically approved
Sjöberg, N.(S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylation.
Open this publication in new window or tab >>(S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylation
(English)Manuscript (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. 

Keywords
chiral auxiliary, diastereomer, tetrahydroisoquinoline, alkylation
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-24597 (URN)
Available from: 2015-03-17 Created: 2015-03-17 Last updated: 2015-04-14Bibliographically approved
Sjöberg, N.Structure determination and synthesis of natural extracts. (S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylation: Licentiate thesis.
Open this publication in new window or tab >>Structure determination and synthesis of natural extracts. (S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylation: Licentiate thesis
(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-24596 (URN)
Available from: 2015-03-17 Created: 2015-03-17 Last updated: 2016-12-08Bibliographically approved
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