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  • 1. Anderbrant, Olle
    et al.
    Matteson, Donald S.
    Unelius, C. Rikard
    Pharazyn, Philip S.
    Santangelo, Ellen M.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Schlyter, Fredrik
    Birgersson, Goran
    Pheromone of the elm bark beetle Scolytus laevis (Coleoptera Scolytidae): stereoisomers of 4-methyl-3-heptanol reduce interspecific competition2010In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 20, no 3, p. 179-187Article in journal (Refereed)
    Abstract [en]

    Stereoisomers of 4-methyl-3-heptanol (MH) are pheromone components of several Scolytus bark beetles. The elm bark beetle Scolytus laevis (Coleoptera: Scolytidae) has in previous studies been caught in traps baited with commercial MH containing all four stereoisomers, but the lure has been considered a weak attractant. In this study, we addressed the question whether stereospecific responses by S. laevis to stereoisomers of MH might contribute to its niche separation from other sympatric Scolytus species. Using GC-MS, we analyzed extracts of hindguts and abdomens from male and female S. laevis and the sympatric S. triarmatus. We also tested all four MH-stereoisomers individually and in combinations in the field to determine their role for S. laevis. All four stereoisomers were synthesized via a boronic ester method with 1,2-dicyclohexylethanediol as chiral director. In addition, the (3S,4R)-stereoisomer of MH was prepared through enantioselective, lipase-mediated transesterification of a mixture of the four stereoisomers of MH. Females of both species contained small amounts of syn-MH, and males contained trace amounts of anti-MH. The anti stereoisomer (3R,4S)-MH was attractive to male and female S. laevis, whereas the syn stereoisomer (3S,4S)-MH acted as an inhibitor or deterrent and reduced the catch when added to the attractive isomer. The syn isomer is the main aggregation pheromone component of the larger and sympatric S. scolytus and possibly also of S. triarmatus. The avoidance response of S. laevis to the (3S,4S)-stereoisomer may reduce interspecific competition for host trees.

  • 2. Bichao, H.
    et al.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wibe, A.
    Araujo, J.
    Mustaparta, H.
    Molecular receptive ranges of olfactory receptor neurones responding selectively to terpenoids, aliphatic green leaf volatiles and aromatic compounds, in the strawberry blossom weevil Anthonomus rubi2005In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 15, no 4, p. 211-226Article in journal (Refereed)
    Abstract [en]

    An important question in insect-plant interactions is which of the numerous plant compounds contribute to the perception of odour qualities in herbivorous insects and are likely to be used as cues in host-searching behaviour. In order to identify which plant-produced volatiles the strawberry blossom weevil Anthonomus rubi detects, we have used electrophysiological recordings from single olfactory neurones linked to gas chromatography and mass spectrometry. We here present 15 receptor neurone types specialised for naturally produced compounds present in the host and nonhost plants and two types for two aggregation pheromone components. The active compounds were terpenoids, aromatic and aliphatic esters, alcohols and aldehydes, some of which are induced by feeding activity of the weevils. The neurones were characterised by a strong response to one or two primary odorants and weaker responses to a few others having similar chemical structure. With one exception, the molecular receptive range of each neurone type was within one chemical group. Enantiomers of linalool separated on a chiral column activated two neurone types with different enantioselectivity. Inhibition by linalool of another neurone type, excited by alpha-pinene, indicated an additional mechanism for coding the information about this compound. Altogether, detection of 54 compounds by olfactory receptor neurones is shown, of which 40 have been chemically identified in this study. Thus A. rubi has the ability to detect a large number of odorants that may be used in host selection behaviour.

  • 3. Faldt, J.
    et al.
    Sjodin, K.
    Persson, M.
    Valterova, I.
    Borg-Karlson, Anna-Karin
    KTH, Superseded Departments, Chemistry.
    Correlations between selected monoterpene hydrocarbons in the xylem of six Pinus (pinaceae) species2001In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 11, no 2, p. 97-106Article in journal (Refereed)
    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.

  • 4. Fors, Lisa
    et al.
    Liblikas, Ilme
    Andersson, Petter
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Cabezas, Nancy
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Mozuraitis, Raimondas
    Hamback, Peter A.
    Chemical communication and host search in Galerucella leaf beetles2015In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 25, no 1, p. 33-45Article in journal (Refereed)
    Abstract [en]

    Herbivore insects use a variety of search cues during host finding and mate recognition, including visual, gustatory, and olfactory stimuli, leaving multiple traits for evolution to act upon. However, information about differences or similarities in search pattern amongst closely related insect herbivore species is still scarce. Here, we study the production of and the response to pheromone in Galerucella (Coleoptera: Chrysomelidae) to investigate the beetles' search behaviour. Males of G. pusilla and G. calmariensis, two closely related species, are known to produce the aggregation pheromone dimethylfuran-lactone when feeding on their host plant, whereas no pheromones have been identified in other Galerucella species. We show that dimethylfuran-lactone is produced also by males of G. tenella, a species phylogenetically close to G. pusilla and G. calmariensis, whereas the more distantly related species G. lineola and G. sagittariae were not found to produce the same compound. To investigate the beetles' behavioural response to dimethylfuran-lactone, the pheromone was synthesized using a partly novel method and tested in olfactometers, showing that G. pusilla, G. calmariensis, and G. tenella were all attracted to the pheromone, whereas G. lineola and G. sagittariae did not respond. This suggests that the production of and the response to pheromone could be linked to the phylogenetic relatedness between the species.

  • 5.
    Mozuraitis, Raimondas
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Liblikas, Ilme
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Noreika, Remigijus
    Sex pheromone communication of tentiform leaf-miners Phyllonorycter insignitella and Ph. nigrescentella from two related species groups2008In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 18, no 3, p. 171-176Article in journal (Refereed)
    Abstract [en]

    Females of both species start their pheromone-releasing activity on the second day after emergence at the beginning of the photophase. During the present work, a peak of calling activity with close to 100% of active Ph. nigrescentella females was registered 1.5 hour after the light had been put on. The high pheromone release behaviour with 50% active females lasted for 3 hours. The calling activity of the group of females was about 6 h/day. The beginning of a photophase under laboratory conditions or an early morning in nature is a common period for sex pheromone release in the genus Phyllonorycter. (8Z,10E)-tetradecadien-1-yl acetate (8Z,10E-14:Ac), (8Z,10E)-tetradecadien-1-ol (8Z,10E-14:OH) and (8E,10Z)-tetradecadien-1-yl acetate (8E,10Z-14:Ac) in the ratio 96:4:traces as well as 8Z,10E-14:Ac and 8Z,10E-14:OH in the ratio 88:12 collected by Solid Phase Micro Extraction (SPME) were found to be specific for the calling periods of virgin Phyllonorycter insignitella and Ph. nigrescentella females respectively. Field trapping experiments demonstrated that all three compounds are important for the attraction of Ph. insignitella males while only 8Z,10E-14:Ac is the essential sex pheromone component for Ph. nigrescentella. The pheromone activity of all three compounds is reported for the first time. Addition of either 8Z,10E-14:OH or 8E,10Z-14:Ac to 8Z,10E-14:Ac did not have a significant effect on the attraction of Ph. nigrescentella males, while the efficiency of the three component blend was 5 times lower as compared to that of 8Z,10E-14:Ac. Our data demonstrate that 8Z,10E-14:OH and 8E,10Z-14:Ac play a dual function, they are minor sex pheromone components of Ph. insignitella essential for attraction of conspecific males and show an allelochemical, antagonistic effect on Ph. nigrescentella males and, thus, ensuring specificity of the mate location signal in two related Phyllonorycter species.

  • 6. Stranden, M.
    et al.
    Rostelien, T.
    Liblikas, I.
    Almaas, T. J.
    Borg-Karlson, Anna-Karin
    KTH, Superseded Departments, Chemistry.
    Mustaparta, H.
    Receptor neurones in three heliothine moths responding to floral and inducible plant volatiles2003In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 13, no 3, p. 143-154Article in journal (Refereed)
    Abstract [en]

    Some plant volatiles are produced in response to herbivory of several insect species, including heliothine larvae. In the present study of female heliothine moths, four co-located receptor neurone types were identified, of which three types responded strongest to the inducible compounds E-beta-ocimene, E,E-alpha-farnesene and E,E-TMTT, respectively. The fourth type responded strongest to geraniol, which is a common floral volatile. The narrow tuning of each receptor neurone type was demonstrated by responses to a few structurally-related monoterpenes, sesquiterpenes, homo-terpenes and monoterpene alcohols, respectively, out of hundreds of plant constituents tested. The four neurone types showed the same relation of spike amplitudes and ranking of effective compounds in the three heliothine species; the polyphagous Heliothis virescens and Helicoverpa armigera and the oligophagous Helicoverpa assulta. The results indicate the presence of functionally similar types of plant odour-receptor neurones in the three related species, and suggest conservation or reappearance of functionally similar olfactory receptors in related species, independent of the evolution of polyphagy and oligophagy.

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