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  • 1. Anderbrant, Olle
    et al.
    Östrand, Fredrik
    Bergström, Gunnar
    Wassgren, Ann-Britt
    Auger-Rozenberg, Marie-Anne
    Geri, Claude
    Hedenström, Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Högberg, Hans-Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Release of sex pheromone and its precursors in the pine sawfly Diprion pini (Hym., Diprionidae)2005Ingår i: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 15, nr 3, s. 147-151Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    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.

     

     

  • 2.
    Fäldt, J.
    et al.
    Royal Institute of Technology, Department of Chemistry, Organic Chemistry, Group of Ecological Chemistry, SE-100 44 Stockholm.
    Sjödin, Kristina
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Persson, M.
    Royal Institute of Technology, Department of Chemistry, Organic Chemistry, Group of Ecological Chemistry, SE-100 44 Stockholm.
    Valterová, I.
    Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
    Borg-Karlson, Anna-Karin
    Royal Institute of Technology, Department of Chemistry, Organic Chemistry, Group of Ecological Chemistry, SE-100 44 Stockholm.
    Correlations between selected monoterpene hydrocarbons in the xylem of six Pinus (pinaceae) species2001Ingår i: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 11, nr 2, s. 97-106Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The compositions of 23 monoterpene hydrocarbons of six pine species (Pinus sylvestris, P. yunnanensis ll,ris, P. armandii, P. tropicalis, P. cubensis and P. caribaca) were compared, using multivariate data analysis. Four of the six species were clearly different from the other species in a Principal Components Analysis (PCA) model, based on the relative amounts (selective normalization) of the monoterpenes. The correlation coefficients between constituents were determined separately for each species and the strongest correlations were found between (+)-alpha -pinene and (+)-camphene and between the corresponding (-)-enantiomers, in all species. This pattern, i.e. a good correlation in all species, was neither shown by the correlation of the structurally more similar (+)-alpha/beta -pinenes, nor by the (-)-alpha/beta -pinenes or within the enantiomeric pairs of alpha -pinene and beta -pinene. For these pairs of monoterpenes, good correlations were found in some species. None of the species showed good correlations in all the investigated monoterpene pairs presented here. Correlations between monoterpenes in insect-attacked trees (P. cubensis and P. caribaea, attacked by Dioryctria horneana, and P. yunnanensis, attacked by Tomicus piniperda) were also determined. The results are discussed from chemotaxonomic and biosynthetic points of view.

  • 3.
    Hedenström, Erik
    et al.
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Avdelningen för kemiteknik.
    Andersson, Fredrik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Avdelningen för kemiteknik.
    Sjöberg, Natalia
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Avdelningen för kemiteknik.
    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 bees2018Ingår i: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 28, nr 4-5, s. 131-135Artikel i tidskrift (Refereegranskat)
    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. 

  • 4.
    Rahmani, Rizan
    et al.
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för kemiteknik.
    Andersson, Fredrik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för kemiteknik.
    Andersson, Martin N.
    Lund university, Lund.
    Yuvaraj, Jothi Kumar
    Lund university, Lund.
    Anderbrant, Olle
    Lund university, Lund.
    Hedenström, Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för kemiteknik.
    Identification of sesquisabinene B in carrot (Daucus carota L.) leaves as a compound electrophysiologically active to the carrot psyllid (Trioza apicalis Forster)2019Ingår i: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 29, nr 3, s. 103-110Artikel i tidskrift (Refereegranskat)
    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.

  • 5. Steinbauer, Martin J
    et al.
    Östrand, Fredrik
    Bellas, Tom
    Nilsson, Anna
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Andersson, Fredrik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Hedenström, Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Lacey, Michael
    Schiestl, P Florian
    Identification, synthesis and activity of sex pheromone gland components of the autumn gum moth (Lepidoptera: Geometridae), a defoliator of Eucalyptus2004Ingår i: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 14, nr 3-4, s. 217-223Artikel i tidskrift (Refereegranskat)
    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.

  • 6. Östrand, Fredrik
    et al.
    Anderbrant, Olle
    Wassgren, Ann-Britt
    Bergström, Gunnar
    Hedenström, Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Högberg, Hans-Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Nguyen, Ba-Vu
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Larsson, Michael
    Stereoisomeric composition of the sex pheromone of the pine sawfly Microdiprion pallipes (Hym., Diprionidae)2003Ingår i: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 13, nr 3, s. 155-162Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The basic chemical structure of the sex pheromone of the pine sawfly Microdiprion pallipes (Fallen) has earlier been identified as the propionate ester of (2S,3S,7 R/S,11 R/S)/(2R,3R,7 R/S,11 R/S)-3,7,11-trimethyl-2-tridecanol. We now report the results from further investigations on the male response to individual stereoisomers and to blends of stereoisomers, both in electroantennographic (EAG) recordings and in field trapping experiments. We also present our attempts to determine the stereochemistry of the compounds present in females of M. pallipes. By comparing gas chromatograms and mass spectra obtained from natural extracts with those from synthetic compounds it was found that the females contain one or more of the four (2S,3S,7 R/S,11 R/S)-3,7,11-trimethyl-2-tridecanol isomers (SS++-1). The active pheromone component is the corresponding propionate ester 2. In EAG experiments, males responded most strongly to five propionate ester samples, namely two four-isomer blends: SS++-2 and SR++-2, and three individual stereoisomers: SSSR-, SRRR- and SRSR-2. In a series of field trapping experiments it was found that males were attracted to the SR++-2 four-isomer blend and to the individual isomer SSSR-2. Based on the EAG-recordings and field responses of males and the stereoisomers found in the females, we suggest that the propionate ester of (2S,3S,7S,11R)-3,7,11-trimethyl-2-tridecanol (SSSR-2) is used as a main component of the sex pheromone in M. pallipes. Apparently the males react to other stereoisomers in addition to that or those produced by the females.

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