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  • 1.
    Abreu, Ilka Nacif
    et al.
    Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC). Umeå University, Faculty of Science and Technology, Department of Plant Physiology.
    Ahnlund, Maria
    Moritz, Thomas
    Albrectsen, Benedicte R.
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC).
    UHPLC-ESI/TOFMS Determination of Salicylate-like Phenolic Gycosides in Populus tremula Leaves2011In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 37, no 8, p. 857-70Article in journal (Refereed)
    Abstract [en]

    Associations of salicylate-like phenolic glycosides (PGs) with biological activity have been reported in Salix and Populus trees, but only for a few compounds, and in relation to a limited number of herbivores. By considering the full diversity of PGs, we may improve our ability to recognize genotypes or chemotype groups and enhance our understanding of their ecological function. Here, we present a fast and efficient general method for salicylate determination in leaves of Eurasian aspen that uses ultra-high performance liquid chromatography-electrospray ionization/time-of-flight mass spectrometry (UHPLC-ESI/TOFMS). The time required for the liquid chromatography separations was 13.5 min per sample, compared to around 60 min per sample for most HPLC protocols. In leaf samples from identical P. tremula genotypes with diverse propagation and treatment histories, we identified nine PGs. We found the compound-specific mass chromatograms to be more informative than the UV-visible chromatograms for compound identification and when quantitating samples with large variability in PG content. Signature compounds previously reported for P. tremoloides (tremulacin, tremuloidin, salicin, and salicortin) always were present, and five PGs (2'-O-cinnamoyl-salicortin, 2'-O-acetyl-salicortin, 2'-O-acetyl-salicin, acetyl-tremulacin, and salicyloyl-salicin) were detected for the first time in P. tremula. By using information about the formic acid adduct that appeared for PGs in the LTQ-Orbitrap MS environment, novel compounds like acetyl-tremulacin could be tentatively identified without the use of standards. The novel PGs were consistently either present in genotypes regardless of propagation and damage treatment or were not detectable. In some genotypes, concentrations of 2'-O-acetyl-salicortin and 2'-O-cinnamoyl-salicortin were similar to levels of biologically active PGs in other Salicaceous trees. Our study suggests that we may expect a wide variation in PG content in aspen populations which is of interest both for studies of interactions with herbivores and for mapping population structure.

  • 2.
    Anderbrant, Olle
    et al.
    Department of Biology, Lund University.
    Löfqvist, Jan
    Department of Plant Protection Science, Swedish University of Agricultural Sciences, Alnarp.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Bång, Joakim
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Tai, Akira
    Faculty of Science, Himeji Institute of Technology, Kanaji Kamigor, Japan.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden2010In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 36, no 9, p. 969-977Article in journal (Refereed)
    Abstract [en]

    The pine sawfly Neodiprion sertifer (Geoffroy) uses the acetate or propionate of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) as pheromone components, with the (2S,3R,7R)-isomer being antagonistic, synergistic, or inactive according to the population tested. In this study, we tested the attraction of males to the acetates of three analogs of diprionol, each missing one methyl group, viz. (2S,7S)-7-methyl-2-pentadecanol, (2S,6S)-2,6-dimethyl-1-tetradecanol, and (2S,3S)-3-methyl-2-pentadecanol. None of the analogs alone, or in combination with diprionol acetate, was attractive in Sweden, even at 100 times the amount of diprionol acetate attractive to N. sertifer. In Japan, the acetate of (2S,3S)-3-methyl-2-pentadecanol attracted males when tested in amounts 10–20 times higher than the acetate pheromone component. The acetate esters of the (2S,3R)-analog and the (2S,3R,7R)-isomer of diprionol also were tested in combination with the pheromone compound (acetate ester). Both compounds caused an almost total trap-catch reduction in Sweden, whereas in Japan they appear to have relatively little effect on trap capture when added to diprionol acetate. Butyrate and iso-butyrate esters of diprionol were unattractive to N. sertifer in Sweden. In summary, there exists geographic variation in N. sertifer in responses to both diprionyl acetate and some of its analogs.

  • 3. Andersson, J.
    et al.
    Borg-Karlson, Anna-Karin
    KTH, Superseded Departments, Chemistry.
    Wiklund, C.
    Antiaphrodisiacs in pierid butterflies: A theme with variation!2003In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 29, no 6, p. 1489-1499Article in journal (Refereed)
    Abstract [en]

    Male Pieris napi butterflies previously have been shown to synthesize and transfer an antiaphrodisiac, methyl salicylate (MeS), to females at mating. This substance curtails courtship and decreases the likelihood of female remating. Here, we show that similar systems occur in Pieris rapae and Pieris brassicae. In P. rapae, C-13-labeling studies showed that males utilize the amino acids phenylalanine and tryptophan as precursors to MeS and indole, respectively. These volatiles are transferred to females at mating and function as antiaphrodisiacs, as demonstrated by field tests entailing painting MeS, indole, or a mixture on the abdomens of virgin females and assessing their attractiveness to wild males. With P. brassicae, C-13-labeling studies showed that males use phenylalanine as a precursor to synthesize benzyl cyanide, which was demonstrated to function as an antiaphrodisiac by field tests similar to those for P. rapae. This communication system exhibits both similarities and differences among the three species; in P. napi and P. rapae, males are fragrant but transfer a volatile antiaphrodisiac to females that is completely different from the male odor, whereas in P. brassicae the antiaphrodisiac transferred by male to female is identical with male odor.

  • 4.
    Azeem, Muhammad
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Kuttuva Rajarao, Gunaratna
    KTH, School of Biotechnology (BIO), Environmental Microbiology (closed September 2009).
    Nordenhem, Henrik
    SLU, Uppsala.
    Nordlander, Göran
    SLU, Uppsala.
    Borg-Karlson, Anna Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Penicillium expansum Volatiles Reduce Pine Weevil Attraction to Host Plants2013In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 39, no 1, p. 120-128Article in journal (Refereed)
    Abstract [en]

    The pine weevil Hylobius abietis (L.) is a severe pest of conifer seedlings in reforested areas of Europe and Asia. To identify minimally toxic and ecologically sustainable compounds for protecting newly planted seedlings, we evaluated the volatile metabolites produced by microbes isolated from H. abietis feces and frass. Female weevils deposit feces and chew bark at oviposition sites, presumably thus protecting eggs from feeding conspecifics. We hypothesize that microbes present in feces/frass are responsible for producing compounds that deter weevils. Here, we describe the isolation of a fungus from feces and frass of H. abietis and the biological activity of its volatile metabolites. The fungus was identified by morphological and molecular methods as Penicillium expansum Link ex. Thom. It was cultured on sterilized H. abietis frass medium in glass flasks, and volatiles were collected by SPME and analyzed by GC-MS. The major volatiles of the fungus were styrene and 3-methylanisole. The nutrient conditions for maximum production of styrene and 3-methylanisole were examined. Large quantities of styrene were produced when the fungus was cultured on grated pine bark with yeast extract. In a multi-choice arena test, styrene significantly reduced male and female pine weevils' attraction to cut pieces of Scots pine twigs, whereas 3-methylanisole only reduced male weevil attraction to pine twigs. These studies suggest that metabolites produced by microbes may be useful as compounds for controlling insects, and could serve as sustainable alternatives to synthetic insecticides.

  • 5.
    Becher, Paul G.
    et al.
    Swedish University of Agricultural Sciences, Alnarp.
    Lebreton, Sebastien
    Swedish University of Agricultural Sciences, Alnarp.
    Wallin, Erika
    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.
    Borrero, Felipe
    Colombian Corporation of Agricultural Research, Las Palmas, Bogota, Colombia.
    Bengtsson, Marie
    Swedish University of Agricultural Sciences, Alnarp.
    Joerger, Volker
    Staatliches Weinbauinstitut, Freiburg, Germany.
    Witzgall, Peter
    Swedish University of Agricultural Sciences, Alnarp.
    The Scent of the Fly2018In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 44, no 5, p. 431-435Article in journal (Refereed)
    Abstract [en]

    (Z)-4-undecenal (Z4-11Al) is the volatile pheromone produced by females of the vinegar fly Drosophila melanogaster. Female flies emit Z4-11Al for species-specific communication and mate-finding. A sensory panel finds that synthetic Z4-11Al has a characteristic flavour, which can be perceived even at the small amounts produced by a single female fly. Since only females produce Z4-11Al, and not males, we can reliably distinguish between single D. melanogaster males and females, according to their scent. Females release Z4-11Al at 2.4 ng/h and we readily sense 1 ng synthetic Z4-11Al in a glass of wine (0.03 nmol/L), while a tenfold concentration is perceived as a loud off-flavour. This corroborates the observation that a glass of wine is spoilt by a single D. melanogaster fly falling into it, which we here show is caused by Z4-11Al. The biological role of Z4-11Al or structurally related aldehydes in humans and the basis for this semiochemical convergence remains yet unclear. 

  • 6. Bohman, B
    et al.
    Nordenhem, H
    Sunnerheim, Kerstin
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Borg-Karlson, A-K
    Unelius, C R
    Structure-activity relationships of phenylpropanoids as antifeedants for the pine weevil Hylobius abietis2008In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 34, no 3, p. 339-352Article in journal (Refereed)
    Abstract [en]

    Ethyl cinnamate has been isolated from the bark of Pinus contorta in the search for antifeedants for the pine weevil, Hylobius abietis. Based on this lead compound, a number of structurally related compounds were synthesized and tested. The usability of the Topliss scheme, a flow diagram previously used in numerous structure-activity relationship (SAR) studies, was evaluated in an attempt to find the most potent antifeedants. The scheme was initially followed stepwise; subsequently, all compounds found in the scheme were compared. In total, 51 phenylpropanoids were tested and analyzed for SARs by using arguments from the field of medicinal chemistry (rational drug design). Individual Hansch parameters based on hydrophobicity, steric, and electronic properties were examined. The effects of position and numbers of substituents on the aromatic ring, the effects of conjugation in the molecules, and the effects of the properties of the parent alcohol part of the esters were also evaluated. It proved difficult to find strong SARs derived from single physicochemical descriptors, but our study led to numerous new, potent, phenylpropanoid antifeedants for the pine weevil. Among the most potent were methyl 3-phenylpropanoates monosubstituted with chloro, fluoro, or methyl groups and the 3,4-dichlorinated methyl 3-phenylpropanoate.

  • 7. Bohman, B
    et al.
    Nordlander, G
    Nordenhem, H
    Sunnerheim, K
    Borg-Karlson, A-K
    Unelius, Rikard
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Structure - activity relationships of phenyl propanoids as antifeedants for the pine weevil Hylobius abieist2008In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 34, no 3, p. 339-352Article in journal (Refereed)
  • 8. Bohman, B.
    et al.
    Nordlander, G.
    Nordenhem, H.
    Sunnerheim, K.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Unelius, C. R.
    Structure-activity relationships of phenylpropanoids as antifeedants for the pine weevil Hylobius abietis2008In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 34, no 3, p. 339-352Article in journal (Refereed)
    Abstract [en]

    Ethyl cinnamate has been isolated from the bark of Pinus contorta in the search for antifeedants for the pine weevil, Hylobius abietis. Based on this lead compound, a number of structurally related compounds were synthesized and tested. The usability of the Topliss scheme, a flow diagram previously used in numerous structure-activity relationship (SAR) studies, was evaluated in an attempt to find the most potent antifeedants. The scheme was initially followed stepwise; subsequently, all compounds found in the scheme were compared. In total, 51 phenylpropanoids were tested and analyzed for SARs by using arguments from the field of medicinal chemistry (rational drug design). Individual Hansch parameters based on hydrophobicity, steric, and electronic properties were examined. The effects of position and numbers of substituents on the aromatic ring, the effects of conjugation in the molecules, and the effects of the properties of the parent alcohol part of the esters were also evaluated. It proved difficult to find strong SARs derived from single physicochemical descriptors, but our study led to numerous new, potent, phenylpropanoid antifeedants for the pine weevil. Among the most potent were methyl 3-phenylpropanoates monosubstituted with chloro, fluoro, or methyl groups and the 3,4-dichlorinated methyl 3-phenylpropanoate.

  • 9. Boone, Celia K
    et al.
    Keefover-Ring, Ken
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology.
    Mapes, Abigail C
    Adams, Aaron S
    Bohlmann, Jörg
    Raffa, Kenneth F
    Bacteria associated with a tree-killing insect reduce concentrations of plant defense compounds2013In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 39, no 7, p. 1003-1006Article in journal (Refereed)
  • 10.
    Borg-Karlson, Anna-Karin
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Nordlander, R.
    Mudalige, A.
    Nordenhem, H.
    Unelius, C. R.
    Antifeedants in the feces of the pine weevil Hylobius abietis: Identification and biological activity2006In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 32, no 5, p. 943-957Article in journal (Refereed)
    Abstract [en]

    Egg-laying females of the pine weevil, Hylobius abietis (L.), regularly deposit feces adjacent to each egg. Egg cavities are gnawed in the bark of roots of recently dead conifer trees. After egg deposition, the cavity is sealed by feces and a plug of bark fragments. Root bark containing egg cavities with feces is avoided as food by pine weevils, which indicates the presence of natural antifeedants. Here we present the first results of the isolation and chemical analyses of antifeedant compounds in the feces of H. abietis. In feeding bioassays, methanol extracts of the feces revealed strong antifeedant properties. Methanol extracts were fractionated by medium-pressure liquid chromatography and the antifeedant effects were mainly found in the fractions of highest polarity. Volatile compounds in the active fractions were identified by gas chromatography-mass spectrometry (GC-MS) and the nonvolatile compounds were characterized by pyrolysis-GC-MS. Based on mass spectra, a number of compounds with various chemical structures were selected to be tested for their antifeedant properties. Antifeedant effects were found among compounds apparently originating from lignin: e.g., a methylanisol, guaiacol, veratrol, dihydroxybenzenes, and dihydroconiferyl alcohol. A weak effect by fatty acid derivatives was found. The types of naturally occurring antifeedant compounds identified in this study may become useful for the protection of planted conifer seedlings against damage by H. abietis.

  • 11.
    Borg-Karlson, Anna-Karin
    et al.
    KTH, Superseded Departments, Chemistry.
    Tengo, J.
    Valterova, I.
    Unelius, C. R.
    Taghizadeh, T.
    Tolasch, T.
    Francke, W.
    (S)-(+)-linalool, a mate attractant pheromone component in the bee Colletes cunicularius2003In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 29, no 1, p. 1-14Article in journal (Refereed)
    Abstract [en]

    Enantiomerically pure (S)-(+)- linalool was the main constituent in the extracts of the cephalic secretions of virgin females, mated females, freshly emerged males, and patrolling males of the solitary bee Colletes cunicularius. After copulation, the content of (S)-(+)- linalool emitted by the female was strongly reduced. Electrophysiological experiments revealed that both enantiomers of linalool elicited responses from the antennae of the males. Field tests using the pure enantiomers and the racemate of linalool showed that the number of male bees attracted was highest for (S)-(+)- linalool. The search flight activity in the mating flight area increased dramatically when patrolling males were presented with (S)-(+)- linalool vs (R)-(+)- linalool. Taken together, these data indicate a mate attractant pheromone function of (S)-(+)- linalool.

  • 12.
    Brown, Robert L.
    et al.
    The New Zealand Institute for Plant & Food Research Ltd, New Zealand ; University of Auckland, New Zealand.
    El-Sayed, Ashraf M
    The New Zealand Institute for Plant & Food Research Ltd, New Zealand.
    Unelius, C. Rikard
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. The New Zealand Institute for Plant & Food Research Ltd, New Zealand.
    Beggs, Jacqueline R
    University of Auckland, New Zealand.
    Suckling, David M
    The New Zealand Institute for Plant & Food Research Ltd, New Zealand ; University of Auckland, New Zealand.
    Invasive Vespula Wasps Utilize Kairomones to Exploit Honeydew Produced by Sooty Scale Insects, Ultracoelostoma.2015In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 41, no 11, p. 1018-1027Article in journal (Refereed)
    Abstract [en]

    Vespula wasps are widely distributed invasive alien species that are able to reach high population densities in the 1.2 M ha of beech forests (Fuscospora spp.) of New Zealand's South Island. These endemic temperate forests have an abundance of carbohydrate-rich honeydew produced by native scale insects (Ultracoelostoma spp.). A characteristic aroma is associated with the honeydew in beech forests, which we hypothesized is the signal used by wasps to harvest the vast resources previously exploited by birds and other insects. Volatile collections were taken of black beech tree trunks with honeydew and sooty mold present, and analyzed with a gas chromatograph-mass spectrometer. Eleven compounds (benzaldehyde, benzyl alcohol, 2-phenylethyl acetate, 2-phenylethanol, phenylacetaldehyde, methyl 2-phenylacetate, ethyl 2-phenylacetate, methyl salicylate, n-octanol, octan-3-ol, and 1-octen-3-ol) were positively identified from the headspace, and were shown to elicit an electrophysiological response from Vespula vulgaris worker antennae by using electroantennography (EAG). Field trials with delta traps individually baited with these compounds confirmed wasp attraction to 8 of the 11 compounds tested, with 2-phenylethyl acetate, methyl salicylate, and octan-3-ol capturing the same numbers of wasps as the control. In later trials, attraction to a 1:1 blend of benzaldehyde and n-octanol was significantly higher (45 %) than to any other treatment. Many of the chemicals identified are known to be associated with fermenting sugars, or with fungal aroma. Benzaldehyde and n-octanol are common compounds produced by many different species in nature. The ability to respond to generic signals emanating from sugar resources is likely to contribute to the success of V. vulgaris as an invasive species.

  • 13. Brännäs, Eva
    et al.
    Nilsson, M. -C
    Nilsson, L.
    Gallet, C.
    Brännäs, Kurt
    Umeå University, Faculty of Social Sciences, Department of Economics.
    Berglind, R.
    Eriksson, L. -O
    Leffler, P. -E
    Zackrisson, O.
    Potential toxic effect on aquatic fauna by the dwarf shrub: Empetrum hermaphroditum2004In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 30, no 1, p. 215-227Article in journal (Refereed)
    Abstract [en]

    The common evergreen dwarf shrub Empetrum hormaphroditum has influence on the functioning of boreal terrestrial ecosystems in northern Sweden. The negative effects of E. hermaphroditum are partly attributed to the production of the dihydrostilbene, batatasin-III, which is released from leaves and litter by rain and snowmelt. In this study, we investigated whether batatasin-III is carried by runoff into streams and lakes during the snowmelt period and whether it is also potentially hazardous to aquatic fauna. Sampling of water from streams and a lake for which the surrounding terrestrial vegetation is dominated by E. hermaphroditum was done during the snowmelt period in May 1993 and in 1998, and analyzed for batatasin-III. Using 24- and 48-hr standard toxicity tests, we analyzed toxicity to brown trout (Salmo trutta) alevins and juvenile water fleas (Daphnia magna). Toxicity (proportion of dead individuals) to trout was tested at pH 6.5 and compared with that of a phenol within a range of concentrations. In the toxicity (proportion of immobilized indivuals) test on D. magna, the interactive effect of pH (pH 5.5-7.0) was included. Concentration of batatasin-III was generally higher in 1998 than in 1993 and showed peak levels during snowmelt. Concentration in ephemeral runnels > the lake > streams running through clear-cuts dominated by E. hermaphroditum > control streams lacking adjacent E. hermaphroditum vegetation. The maximum concentration of batatasin-III found was 1.06 mg l-1. The proportion of dead yolk sac alevins increased significantly (P < 0.001) with increasing concentrations of batatasin-III and time of exposure. After 24 hr, EC 50 was 10 mg l-1. It was 2 mg l-1 after 48 hr. The effect of phenol was negligible, indicating a specific phytotoxic effect of the bibenzyl structure of batatasin-III. The proportion of mobile D. magna became significantly smaller (P < 0.001) with increasing concentrations of batatasin-III, with decreasing pH, and with increasing exposure time. EC 50 varied between 7 and 17 mg l-1 at pH 5.5 and 7.0, respectively. After 24 hr EC50 decreased and was 2.5 at pH 5.5 and 12 mg l-1 at pH 7.0. The levels of batatasin-III found in the field samples were below the lowest EC50 in acute toxicity tests. However, in view of the interactive effect of pH and exposure time, this study suggests that this stable plant metabolite may impose a lethal effect on the aquatic fauna in small streams.

  • 14. Buda, V.
    et al.
    Mäeorg, U.
    Karalius, V.
    Rothschild, G. H. L.
    Kolonistova, S.
    Ivinskis, P.
    Mozuraitis, Raimondas
    C18 Dienes as attractants for eighteen clearwing (Sesiidae), tineid (Tineidae), and choreutid (Choreutidae) moth species1993In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 19, no 4, p. 799-813Article in journal (Refereed)
    Abstract [en]

    By screening singly and binary mixed 2,13- and 3,13-octadecadien-yl acetates and alcohols (2,13- and 3,13-18: Ac/OH)in Lithuania, Armenia, Azerbaijan, Turkmenistan, Ukraine, and the far east of Russia, sex attractants were discovered for 12 Sesiidae, four Tineidae, and one Choreutidae moth species. Males of Sesia yezoensis and Bembecia puella as well as Nemapogon flavifrons were attracted by mixture of Z3,Z13-18:Ac/OH in a ratio of 9:1, Pyropteron sp. n. by the same mixture (ratio 1:9), Bembecia romanovi and B. zuwandica by Z3,Z13-18:AC and E3,Z13-18:Ac (9:1), Synanthedon caucasicum by the same mixture in the opposite ratio (1:9), B. scopigera by 23,213-18:Ac and E2,Z13-18:OH in a ratio 9:1, Synasphecia triannuliformis by Z3,Z13-18:OH and E3,Z13-18:OH (9: 1), Similipepsis takizawai and Archimeessia sp. n. by E3,Z13-18:OH and E2,Z13-18:Ac (1:1), Prochoreutis sechestediana by a mixture of E3,Z13-18:Ac plus E2,Z13-18:OH (1:), Microsphecia brosiformis by E3,Z13-18:Ac, Synanthedon conopiformis by the analogous alcohol, Synanthedon scoliaeformis and Nemaxera betulinella by E2,Z13-18:Ac, Triaxomera fulvimitrella by Z3,Z13-18:Ac. An analogous alcohol component is essential for the attraction of B. ichneumoniformis males. Inhibitors for B. romanovi, B. scopigera and B. zuwandica attraction were discovered. Preliminary data on attractants for six other species as well as on the diurnal rhythm of sexual activity of three species are presented. A new method for the stereoselective synthesis of 3,13-18:Ac/OH and E2,Z13-18:Ac/OH is described.

  • 15. Buda, Vincas
    et al.
    Mozuraitis, Raimondas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Kutra, Jonas
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    p-Cresol: A Sex Pheromone Component Identified from the Estrous Urine of Mares2012In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 38, no 7, p. 811-813Article in journal (Refereed)
    Abstract [en]

    Previously it was shown that m- and p-cresols in the urine of mares exhibits a temporally reproducible pattern that is dependent on ovarian activity and, thus, provides information about the timing of ovulation. New behavioral data demonstrate 1) that stallions spend significantly more time sniffing p-cresol as compared to o-, and m-cresols, and, 2) that the extent of stallions' erections differ significantly in response to different types of samples. The lowest erection level was recorded for the pure-water control, a moderate erection level was elicited by the urine of diestrous mares, and the highest erection level was elicited by urine of a diestrous mare containing synthetic p-cresol at a quantity equivalent to half of the amount of p-cresol found in the urine of estrous mares. Consequently, p-cresol is at least one of the components of a horse sex pheromone.

  • 16.
    Burdon, Rosalie C. F.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Genetics, Plant Ecology and Evolution.
    Raguso, Robert A.
    Cornell Univ, Dept Neurobiol & Behav, Ithaca, NY 14853 USA..
    Kessler, Andre
    Cornell Univ, Dept Ecol & Evolutionary Biol, Ithaca, NY 14853 USA..
    Parachnowitsch, Amy L.
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Genetics, Plant Ecology and Evolution.
    Spatiotemporal floral scent variation of Penstemon digitalis2015In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 41, no 7, p. 641-650Article in journal (Refereed)
    Abstract [en]

    Variability in floral volatile emissions can occur temporally through floral development, during diel cycles, as well as spatially within a flower. These spatiotemporal patterns are hypothesized to provide additional information to floral visitors, but they are rarely measured, and their attendant hypotheses are even more rarely tested. In Penstemon digitalis, a plant whose floral scent has been shown to be under strong phenotypic selection for seed fitness, we investigated spatiotemporal variation in floral scent by using dynamic headspace collection, respectively solid-phase microextraction, and analyzed the volatile samples by combined gas chromatography-mass spectrometry. Total volatile emission was greatest during flowering and peak pollinator activity hours, suggesting its importance in mediating ecological interactions. We also detected tissue and reward-specific compounds, consistent with the hypothesis that complexity in floral scent composition reflects several ecological functions. In particular, we found tissue-specific scents for the stigma, stamens, and staminode (a modified sterile stamen common to all Penstemons). Our findings emphasize the dynamic nature of floral scents and highlight a need for greater understanding of ecological and physiological mechanisms driving spatiotemporal patterns in scent production.

  • 17.
    Byers, J. A.
    et al.
    SLU, Alnarp.
    Hogberg, H. E.
    Midsweden University, Sundsvall.
    Unelius, C. Rikard
    KTH, Stockholm.
    Birgersson, G.
    SLU, Alnarp.
    Lofqvist, J.
    SLU, Alnarp.
    Structure Activity Studies on Aggregation Pheromone Components of Pityogenes-Chalcographus (Coleoptera, Scolytidae) - All Stereoisomers of Chalcogran and Methyl 2,4-Decadienoate1989In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 15, no 2, p. 685-695Article in journal (Refereed)
  • 18. Byers, J
    et al.
    Högberg, Hans-Erik
    Unelius, C. R.
    Birgersson, G.
    Löfqvist, J.
    Structure-Activity Studies on Aggregation Pheromone Components of Pithyogenes chalcographus (Coleoptera: Scolytidae): All stereoisomers of Chalcogran and Methyl 2,4-Decadienoate1989In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 15, no 2, p. 685-695Article in journal (Refereed)
  • 19.
    Bång, Joakim
    et al.
    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.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Purification, Stereoisomeric Analysis and Quantification of Sex Pheromone Precursors in Female Whole Body Extracts from Pine Sawfly Species2011In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 37, no 1, p. 125-133Article in journal (Refereed)
    Abstract [en]

    A GC-MS method to analyze the stereoisomeric composition of chiral secondary alcohols found in whole body extracts of pine sawfly females was developed. The tested alcohols were derivatized with optically pure (S)-2-acetoxypropionyl chloride prior to GC-MS analysis. Baseline separation was obtained for all sixteen stereoisomers of 3,7,9-trimethyltridecan-2-ol and for the four 3-methylpentadecan-2-ol stereoisomers. For 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol and 3,7-dimethylpentadecan-2-ol baseline separation was obtained for 6 of the possible 8 stereoisomers. When a mixture of 16 stereoisomers of 3,7,11-trimethyltridecan-2-ol was tested, baseline separation of 7 peaks out of 16 possible was obtained. The investigated alcohols are pheromone precursors for some pine sawfly species that are severe defoliators of pine. Females from several Diprion, Neodiprion, Macrodiprion, Microdiprion, and Gilpinia species emit esters of such secondary alcohols as sex pheromones that attract males for mating. To quantify the small amounts of the precursor alcohol and its stereoisomeric composition found in whole body extracts from female pine sawflies, a purification method was optimized. An extract of 20 females of D. pini contained about 8 ng of (2 S,3 R,7 R)-3,7-dimethyltridecan-2-ol per female, and three extracts of 18, 20, and 90 females of N. sertifer contained between 5 and 13 ng of (2 S,3 S,7 S)-3,7-dimethylpentadecan-2-ol per female.

  • 20. Cozzolino, Salvatore
    et al.
    Fineschi, Silvia
    Litto, Maria
    Scopece, Giovanni
    Trunschke, Judith
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Genetics, Plant Ecology and Evolution.
    Schiestl, Florian P.
    Herbivory increases fruit set in Silene latifolia: a consequence of induced pollinator-attracting floral volatiles?2015In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 41, no 7, p. 622-630Article in journal (Refereed)
    Abstract [en]

    Although the effect of herbivory on plant reproduction has been investigated in some detail, little is known about how herbivores affect floral signalling. Here, we investigated the effect of foliar herbivory by the African Cotton Leafworm (Spodoptera littoralis) on floral signalling and fruit set in the White Campion (Silene latifolia). We found no effects of herbivory on floral traits involved in visual signalling (flower number, corolla diameter, calyx length, petal length) or in amount of nectar produced. However, Spodoptera-infested plants emitted higher amounts of the two floral volatiles, (Z)-3-hexenyl acetate and β-ocimene, than control plants. Open pollinated, infested plants also were found to produce more fruits than control plants, but only with nocturnal pollinators. Experimental addition of the two induced floral volatiles to non-infested Silene flowers also led to the production of more fruits with nocturnal pollination. This suggests that higher fruit production in herbivore-infested plants was caused by increased nocturnal pollinator attraction, mediated by the induced floral emission of these two volatiles. Our results show that the effects of herbivory on plant reproductive success are not necessarily detrimental, as plants can compensate herbivory with increased investment in pollinator attraction.

  • 21. Cunningham, Paul J.
    et al.
    Carlsson, Mikael A.
    Stockholm University, Faculty of Science, Department of Zoology.
    Villa, Thomas F.
    Dekker, Teun
    Clarke, Anthony R.
    Do Fruit Ripening Volatiles Enable Resource Specialism in Polyphagous Fruit Flies?2016In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 42, no 9, p. 931-940Article in journal (Refereed)
    Abstract [en]

    Frugivorous tephritid fruit flies have lineages with high levels of host generalism. These insects use olfaction to locate fruits, but how they are able to recognize the odors of so many different host species is poorly understood. We used a series of behavioral experiments to investigate the role of fruit ripening volatiles as host cues in the Queensland fruit fly, Bactrocera tryoni (Froggatt), a polyphagous pest in Australia. Odors of mature guava (Psidium guajava) attracted female and male flies more strongly than three other ripening stages and guava pulp. We analyzed volatiles from guava odor and selected eleven compounds, all of which elicited an electrophysiological response in the antenna of female flies. Three of these, ethyl acetate, ethyl butyrate, and ethyl propionate, were released at the highest rates from the most attractive ripening stage. In behavioral trials, these three esters were not attractive individually, whereas a combination was necessary and sufficient in attracting female flies. The three-component blend was as attractive as the entire 11-component blend, which without these key volatiles was not attractive. Moreover, injecting low ranking hosts (squash and cucumber) with the three volatiles increased attraction in ovipositing female flies. These fruit flies are classed as generalists, but like many polyphagous insects they could be regarded as resource specialists, preferring specific plant reproductive stages with predictable odor cues. Exploring olfaction from this perspective could improve our understanding of host choice in polyphagous insects, and the selection of volatiles to be used as attractants in insect pest management.

  • 22.
    Cárdenas, Paco
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Organismal Biology, Systematic Biology.
    Who Produces Ianthelline? The Arctic Sponge Stryphnus fortis or its Sponge Epibiont Hexadella dedritifera: a Probable Case of Sponge-Sponge Contamination2016In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 42, no 4, p. 339-347Article in journal (Refereed)
    Abstract [en]

    The bromotyrosine derivative ianthelline was isolated recently from the Atlantic boreo-arctic deep-sea sponge Stryphnus fortis, and shown to have clear antitumor and antifouling effects. However, chemosystematics, field observations, and targeted metabolic analyses (using UPLC-MS) suggest that ianthelline is not produced by S. fortis but by Hexadella dedritifera, a sponge that commonly grows on S. fortis. This case highlights the importance of combining taxonomic and ecological knowledge to the field of sponge natural products research.

  • 23. El-Sayed, A M
    et al.
    Wainman, L I
    Santangelo, Ellen
    KTH, Superseded Departments, Chemistry.
    Unelius, C. Rikard
    KTH, Superseded Departments, Chemistry.
    Trimble, R M
    Relative attractiveness of (10E)-dodecen-1-yl acetate and (4E,10E)-dodecadien-1-yl acetate to male spotted tentiform leafminers Phyllonorycter blancardella (F.)2004In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 30, no 9, p. 1827-1838Article in journal (Refereed)
    Abstract [en]

    The antennae of male spotted tentiform leafminers, Phyllonorycter blancardella, from Ontario, Canada, exhibited similar electroantennogram responses when stimulated with E10-12:Ac or E4,E10-12:Ac. In field trapping experiments, E10-12:Ac was two-fold or more attractive than E4, E10-12:Ac, and E4,E10-12:Ac did not enhance the attractiveness of E10-12:Ac. E4,E10-12:Ac has not been identified in the pheromone of P. blancardella and it is hypothesized that the structural similarity of this compound and E10-12:Ac, the major pheromone compound of this species, may be responsible for the electrophysiological and behavioral responses to E4,E10-12:Ac. The possible reasons for the disparity between the results of our field trapping experiments and those carried out in Nova Scotia, Canada, and Massachusetts, USA., where E4,E10-12:Ac was found to be two to four times more attractive to P. blancardella than E10-12:Ac, are discussed.

  • 24. El-Sayed, A.M.
    et al.
    Wainman, L.I.
    Santangelo, E.M.
    Unelius, Rikard
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Trimble, R.M.
    Relative Attractiveness of (10E)-Dodecenyl Acetate and (4E,10E)-Dodecadienyl Acetate to Male Spotted Tentiform Leafminers Phyllonorycter blancardella (F.),2004In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 30, no 9, p. 1827-38Article in journal (Refereed)
  • 25.
    El-Seedi, Hesham R
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
    Bohlin, Lars
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
    Ghia, Felipe
    Torssell, Kurt B G
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
    Ecologically active 2-octanoylcyclohexane-1,3-dione from Philodendron guttiferum2001In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 27, no 3, p. 517-521Article in journal (Refereed)
    Abstract [en]

    The novel naturally occurring 2-octanoylcyclohexane-1,3-dione 1 was isolated in its enol form from P. guttiferum (Araceae). Its chemical ecological relevance is discussed. There was mass spectral evidence for the presence of small amounts of the homologous 2-decanoyl and 2-dodecanoyl derivatives.

  • 26. Eltz, Thomas
    et al.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Bång, Joakim
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Wallin, Erika A
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Andersson, Jimmy
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    (6R,10R)-6,10,14-Trimethylpentadecan-2-one, a Dominant and Behaviorally Active Component in Male Orchid Bee Fragrances2010In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 36, no 12, p. 1322-1326Article in journal (Refereed)
    Abstract [en]

    6,10,14-Trimethylpentadecan-2-one (Hexahydrofarnesyl acetone; HHA) previously has been found to be a major component in tibial fragrances of male orchid bees, Euglossa spp. HHA is a chiral molecule with four possible stereoisomers, (6R,10R)-, (6R,10S)-, (6S,10R)-, and (6S,10S)-6,10,14-trimethylpentadecan-2-one. In the present study, we characterized HHA extracted from Euglossa as the pure enantiomer (6R,10R)-6,10,14-trimethylpentadecan-2-one. During bioassays in Mexico and Panama, the synthetic RR-isomer attracted males of six species of orchid bees, including three that were known to contain HHA in their tibial fragrances. Possible sources of HHA for wild bees are flowers of euglossophilous orchids and aroids. With a molecular weight of 268, HHA is the largest natural molecule known to attract male orchid bees in pure form. Its attractiveness to males suggests that low-volatility compounds have a function in male signals, e.g., serve as a "base note" in complex odor bouquets. © 2010 Springer Science+Business Media, LLC.

  • 27.
    Eriksson, Carina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Månsson, P. E.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Schlyter, F
    Antifeedants and feeding stimulants in bark extracts of ten woody non-host species of the pine weevil, Hylobius abietis.2008In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 34, no 10, p. 1290-1297Article in journal (Refereed)
  • 28. Eriksson, Carina
    et al.
    Månsson, Per E.
    Sjödin, Kristina
    Schlyter, Fredrik
    Antifeedants and feeding stimulants in bark extracts of ten woody non-host species of the pine weevil, Hylobius abietis2008In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 34, no 10, p. 1290-1297Article in journal (Refereed)
    Abstract [en]

    Bark of ten woody species, known to be rejected as a food source by the pine weevil, Hylobius abietis, were sequentially extracted by a Soxhlet apparatus with pentane followed by methanol. Species were alder (Alnus glutinosa), aspen (Populus tremula), beech (Fagus sylvatica), guelder rose (Viburnum opulus), holly (Ilex aquifolium), horse chestnut (Aesculus hippocastanum), lilac (Syringa vulgaris), spindle tree (Evonymus europaeus), walnut (Juglans regia), and yew (Taxus baccata). Bark of each species was collected in southern Scandinavia during the summer. Resulting extracts were tested for antifeedant activity against the pine weevil by a micro-feeding choice assay. At a dose corresponding to that in the bark, methanol extracts from Aesculus, Taxus, Ilex, and Populus were antifeedant active, while pentane extracts of Aesculus, Fagus, Syringa, and Viburnum were stimulatory. Four known antifeedants against H. abietis, the straight-chained carboxylic acids, hexanoic and nonanoic acid (C6 and C9), carvone, and carvacrol were identified by gas chromatography (GC)-mass spectrometry (MS) in several extracts. The major constituents were identified and tested for feeding deterrence. The aromatic compounds benzyl alcohol and 2-phenylethanol are new non-host plant-derived feeding deterrents for the pine weevil. Additionally, two feeding stimulants, beta-sitosterol and 5-(hydroxymethyl)-2-furaldehyde, were identified. One active methanol extract of Aesculus bark was sequentially fractionated by liquid chromatography, and major compounds were tentatively identified as branched alcohols and esters of hexanoic acid. Five commercially available hexanoate esters and two commercially available branched alcohols were identified as new active antifeedants. Both stimulatory and inhibiting compounds were found in the same extracts and co-eluted in the same or adjacent fractions. The mix of semiochemicals of opposite activity in each extract or fraction could explain the stimulatory-, inhibitory-, or sometimes neutral activity. Generally, such co-occurrence confounds the isolation of antifeedants.

  • 29. Faldt, Jenny
    et al.
    Solheim, Halvor
    Langstrom, Bo
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Influence of fungal infection and wounding on contents and enantiomeric compositions of monoterpenes in phloem of Pinus sylvestris2006In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 32, no 8, p. 1779-1795Article in journal (Refereed)
    Abstract [en]

    To identify chemical resistant markers induced by fungal or mechanical injury, young trees of Scots pine (Pinus sylvestris) were subjected to inoculations of blue stain fungi associated with the pine shoot beetles Tomicus piniperda and T. minor. Among the 20 trees selected for chemical analyses, 16 were divided into four groups: one as control and three were pretreated by wounding only, or by inoculation with either the blue stain fungus Leptographium wingfieldii or Ophiostoma canum. Four wk after pretreatment, all 16 pretreated trees were mass-inoculated with L. wingfieldii. The absolute and relative amounts, as well as the enantiomeric compositions of monoterpene hydrocarbons in the phloem, were determined via a small sample of the phloem before and after the pretreatment and mass inoculation, by using two-dimensional gas chromatography (2D GC) and GC-mass spectrometry (MS). After mass inoculation, the absolute amounts of most of the monoterpenes decreased in the phloem sampled > 20 cm from the fungal infection, and were higher in the phloem sampled within the infected reaction zone. The relative amounts of both (-)-beta-pinene and (-)-limonene increased in phloem samples taken > 20 cm above the fungal inoculation in the preinoculated trees compared with phloem sampled from the remaining four control trees. The enantiomeric compositions of beta-pinene and limonene changed, after fungal growth, at defined distances from the inoculation site: the proportion of the (-)-enantiomers was highest in the phloem sampled > 20 cm from the fungal inoculation. Four wk after pretreatment, monoterpene production in the phloem at the site of inoculation was more enhanced by L. wingfieldii than by O. canum. However, the different virulence levels of the fungi did not affect the enantiomeric composition of the monoterpenes. The biosynthesis of monoterpene enantiomers is discussed in relation to induced pathogen resistance.

  • 30. Francke, W.
    et al.
    Karalius, V.
    Plass, E.
    Lehmann, L.
    Dos Santos, A.
    Buda, V.
    Borg-Karlson, Anna-Karin
    KTH, Superseded Departments, Chemistry.
    Mozuraitis, Raimondas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    New type of sesiidae sex pheromone identified from the hornet moth Sesia apiformis2004In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 30, no 4, p. 805-817Article in journal (Refereed)
    Abstract [en]

    Two components of the female-produced sex pheromone of the hornet moth, Sesia apiformis, were identified as (3Z, 13Z)-octadeca-3,13-dien-1-ol (3Z, 13Z-18:OH) and (2E, 13Z)-octadeca-2,13-dienal (2E, 13Z-18:Al), a pheromone structure new in Sesiidae. Pooled gland extracts showed the two major compounds in a proportion of ca. 2:3, while SPME-investigations on single calling females revealed a ratio of ca. 1:7. Although the single compounds were not attractive, a 2: 3 mixture proved to be highly active towards males in field tests. Small amounts of (2E, 13Z)-octadecadienol (2E, 13Z-18:OH) were found in the sex pheromone gland of females, however, the biological significance of the compound remains unclear. Methyl sulfide was found to readily react with 2-alkenals, providing an effective new method for the characterization of this type of compound upon GC/MS. The derivatives, 1,1,3-tris(methylthio)alkanes, are the products of the addition of methyl sulfide to the double bond and the transformation of the carbonyl group into the corresponding bis(methylthio)acetal. The mass spectra of these compounds are characterized by diagnostic signals at m/z 107 and/or m/z 121. These fragments represent the first carbon unit or the first two carbon units of the derivative, respectively. The parent signal in the spectra of thiomethyl derivatives of 2-alkenals showing no other double bonds is represented by m/z M+-121, formed upon loss of the first two carbon units. By employing a solution of methyl sulfide in dimethyl sulfide, the double bond positions in 2E, 13Z-18:Al could be fully characterized by GC/MS.

  • 31.
    Friberg, Magne
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Genetics, Plant Ecology and Evolution.
    Schwind, Christopher
    Roark, Lindsey C.
    Raguso, Robert A.
    Thompson, John N.
    Floral Scent Contributes to Interaction Specificity in Coevolving Plants and Their Insect Pollinators2014In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 40, no 9, p. 955-965Article in journal (Refereed)
    Abstract [en]

    Chemical defenses, repellents, and attractants are important shapers of species interactions. Chemical attractants could contribute to the divergence of coevolving plant-insect interactions, if pollinators are especially responsive to signals from the local plant species. We experimentally investigated patterns of daily floral scent production in three Lithophragma species (Saxifragaceae) that are geographically isolated and tested how scent divergence affects attraction of their major pollinator the floral parasitic moth Greya politella (Prodoxidae). These moths oviposit through the corolla while simultaneously pollinating the flower with pollen adhering to the abdomen. The complex and species-specific floral scent profiles were emitted in higher amounts during the day, when these day-flying moths are active. There was minimal divergence found in petal color, which is another potential floral attractant. Female moths responded most strongly to scent from their local host species in olfactometer bioassays, and were more likely to oviposit in, and thereby pollinate, their local host species in no-choice trials. The results suggest that floral scent is an important attractant in this interaction. Local specialization in the pollinator response to a highly specific plant chemistry, thus, has the potential to contribute importantly to patterns of interaction specificity among coevolving plants and highly specialized pollinators.

  • 32. Gibb, A.R.
    et al.
    Suckling, D.M.
    El-Sayed, A.M.
    Bohman, Björn
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Unelius, Rikard
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Dymock, J.J
    Larsen, M.L.
    Willoughby, B.E.
    (Z,E)-11,13-Hexadecadienyl Acetate: Sex Pheromone of the Grass Webworm Herpetogramma licarsisalis - Identification, Synthesis and Field Bioassays.2007In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 33, no 4, p. 839-47Article in journal (Refereed)
  • 33.
    Hagman, Mattias
    et al.
    Stockholm University, Faculty of Science, Department of Zoology, Ethology.
    Shine, Richard
    Factors influencing responses to alarm pheromones by tadpoles of invasive cane toads (Bufo marinus)2009In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 35, p. 265-271Article in journal (Refereed)
    Abstract [en]

    If pheromonal communication systems of invasive species differ from those of native biota, it may be possible to control the invader by exploiting that difference. When injured, the larvae of cane toads, Bufo marinus, an invasive species of major concern in tropical Australia, produce species-specific chemical cues that alert conspecific tadpoles to danger. Repeated exposure to the alarm chemical reduces tadpole survival rates and body sizes at metamorphosis and, thus, could help control toad populations. To evaluate the feasibility of this approach, we need to know how the intensity of toad tadpole response to the alarm chemical is affected by factors such as water temperature, time of day, larval stage and feeding history, geographic origin of the tadpoles, and habituation. Information on these topics may enable us to optimize deployment, so that tadpoles encounter pheromone at the times and places that confer maximum effect. In our studies, tadpole density, nutritional state, larval stage, and geographic origin had little effect on the intensity of the alarm response, but tadpoles reacted most strongly in higher water temperatures and during daylight hours. Repeated, once-daily exposure to pheromone did not induce habituation, but repeated exposure at 15-min interva

  • 34. Hayes, Andrew
    et al.
    Crossland, Michael
    Hagman, Mattias
    Stockholm University, Faculty of Science, Department of Zoology.
    Capon, Rob
    Shine, Richard
    Ontogenetic variation in the chemical defenses of cane toads (Bufo marinus): toxin profiles and effects on predators.2009In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 35, p. 391-399Article in journal (Refereed)
    Abstract [en]

    We conducted a quantitative and qualitative chemical analysis of cane toad bufadienolides-the cardioactive steroids that are believed to be the principal cane toad toxins. We found complex shifts in toxin composition through toad ontogeny: (1) eggs contain at least 28 dominant bufadienolides, 17 of which are not detected in any other ontogenetic stage; (2) tadpoles present a simpler chemical profile with two to eight dominant bufadienolides; and (3) toxin diversity decreases during tadpole life but increases again after metamorphosis (larger metamorph/juvenile toads display five major bufadienolides). Total bufadienolide concentrations are highest in eggs (2.64 +/- 0.56 mu mol/mg), decreasing during tadpole life stages (0.084 +/- 0.060 mu mol/mg) before rising again after metamorphosis (2.35 +/- 0.45 mu mol/mg). These variations in total bufadienolide levels correlate with toxicity to Australian frog species. For example, consumption of cane toad eggs killed tadpoles of two Australian frog species (Limnodynastes convexiusculus and Litoria rothii), whereas no tadpoles died after consuming late-stage cane toad tadpoles or small metamorphs. The high toxicity of toad eggs reflects components in the egg itself, not the surrounding jelly coat. Our results suggest a dramatic ontogenetic shift in the danger that toads pose to native predators, reflecting rapid changes in the types and amounts of toxins during toad development.

  • 35.
    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.

  • 36.
    Hedenström, Erik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Edlund, Helene
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Wassgren, Ann-Britt
    Göteborg University.
    Bergström, Gunnar
    Göteborg University.
    Anderbrant, Olle
    Lund University.
    Östrand, Fredrik
    Lund University.
    Sierpinski, Andrzej
    Forest Research Institute, Poland.
    Auger-Rozenberg, Marie-Anne
    Institut National de la Recherche Agronomique, France.
    Herz, Marie-Anne
    Technische Universität München, Germany.
    Heitland, Werner
    Technische Universität München, Germany.
    Varama, Martti
    Finnish Forest Research Institute, Finland.
    Sex pheromone of the pine sawfly, Gilpinia pallida: Chemical identification, synthesis, and biological activity2006In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 32, no 11, p. 2525-2541Article in journal (Refereed)
    Abstract [en]

    We present the identification of the sex pheromone in the pine sawfly, Gilpinia pallida, including analysis of the female pheromone content, male antennal response and attraction in the field, and synthesis of the most active pheromone component. Several 3,7-dimethyl-2-alkanols were identified from female whole-body extracts, including some compounds with a 2R configuration. This is the first observation of such compounds in a pine sawfly species. Antennae of male G. pallida responded strongly in electroantennograph (EAG) recordings to the (2S,3R,7R)-isomers of the propionates of 3,7-dimethyl-2-tridecanol, 3,7-dimethyl-2-tetradecanol, and 3,7-dimethyl-2-pentadecanol, as well as to the acetates of the tri- and pentadecanols (the acetate of the tetradecanol was not tested). The propionate of (2S,3R,7R)-3,7-dimethyl-2-tetradecanol caught more males in the field than the corresponding isomer of tri- or pentadecanol. We suggest that the (2S,3R,7R)-isomer of 3,7-dimethyl-2-tetradecanol is likely the main sex pheromone precursor in G. pallida, with a subsidiary role for the (2S,3R,7R)-isomer of the tridecanol. Preparation of highly pure (2R,3R,7R)- and (2S,3R,7R)-stereoisomers of 3,7-dimethyl-2-tetradecanol, including the biological active esters, was performed via chemoenzymatic methods and is described in detail.

  • 37.
    Hedenström, Erik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Wallin, Erika
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Andersson, J
    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.
    Wang, H-L
    Department of Biology, Lund University, Sölvegatan 37, Lund, Sweden .
    Löfstedt, C
    Department of Biology, Lund University, Sölvegatan 37, Lund, Sweden .
    Brattström, O
    Department of Zoology, Cambridge University, Cambridge, United Kingdom.
    Baquet, P
    Evolutionary Ecology and Genetics group, Biodiversity Research Centre, Earth and Life Institute, Académie Louvain, Croix du Sud 4, Louvain-la-Neuve, Belgium.
    Stereoisomeric Analysis of 6,10,14-Trimethylpentadecan-2-ol and the Corresponding Ketone in Wing Extracts from African Bicyclus Butterfly Species2015In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 41, no 1, p. 44-51Article in journal (Refereed)
    Abstract [en]

    Gas chromatography (GC) and mass spectrometry (MS) were used to determine the stereoisomeric compositions of 6,10,14-trimethylpentadecan-2-ol and 6,10,14-trimethylpentadecan-2-one in wing extracts from 17 Bicyclus butterfly species from different regions of Africa. All samples were purified using solid phase extraction (SPE). Since some species contained both alcohol and ketone, these were separated and the ketone was reduced to the alcohol before analysis as either (R)-trans-chrysanthemoyl or (S)-2-acetoxypropionyl esters. A novel asymmetric synthesis was developed for a reference mixture of (2R/S,6S,10R)-6,10,14-trimethylpentadecan-2-ol with known composition of the eight stereoisomers. The mixture then was used as the (R)-trans-chrysanthemoyl esters to correlate each of the eight gas chromatographic peaks to a specific stereoisomer of the extracted wing compounds. Seven butterfly species showed (2R,6R,10R)-configuration of the alcohol, four species contained minute amounts of alcohol too small to determine the stereochemistry, nine species showed (6R,10R)-configuration of the ketone, and one species contained minute amounts of ketone too small to determine the stereochemistry. No other stereoisomers of alcohol or ketone could be detected in the extracts, and the quantities of the compounds in the wing extracts varied from 5 to 900 ng per sample for each species.

  • 38. Holeski, Liza M
    et al.
    Keefover-Ring, Ken
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology.
    Bowers, M Deane
    Harnenz, Zoe T
    Lindroth, Richard L
    Patterns of phytochemical variation in Mimulus guttatus (Yellow Monkeyflower)2013In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 39, no 4, p. 525-536Article in journal (Refereed)
    Abstract [en]

    The search for general patterns in the production and allocation of plant defense traits will be facilitated by characterizing multivariate suites of defense, as well as by studying additional plant taxa, particularly those with available genomic resources. Here, we investigated patterns of genetic variation in phytochemical defenses (phenylpropanoid glycosides, PPGs) in Mimulus guttatus (yellow monkeyflower). We grew plants derived from several natural populations, consisting of multiple full-sibling families within each population, in a common greenhouse environment. We found substantial variation in the constitutive multivariate PPG phenotype and in constitutive levels of individual phytochemicals within plants (among leaves of different ages), within populations (among full-sibling families), and among populations. Populations consisting of annual plants generally, but not always, had lower concentrations of phytochemicals than did populations of perennial plants. Populations differed in their plastic response to artificial herbivory, both in the overall multivariate PPG phenotype and in the individual phytochemicals. The relationship between phytochemistry and another defense trait, trichomes, differed among populations. Finally, we demonstrated that one of the PPGs, verbascoside, acts as a feeding stimulant rather than a feeding deterrent for a specialist herbivore of M. guttatus, the buckeye caterpillar (Junonia coenia Nymphalidae). Given its available genetic resources, numerous, easily accessible natural populations, and patterns of genetic variation highlighted in this research, M. guttatus provides an ideal model system in which to test ecological and evolutionary theories of plant-herbivore interactions.

  • 39. Johansson, Björn
    et al.
    Anderbrant, Olle
    Simandl, Jiri
    Avtzis, Nikolaos
    Salvadori, Christina
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Edlund, Helen
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Release Rates for Pine Sawfly Pheromones from Two Types of Dispensers and Phenology of Neodiprion sertifer2001In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 27, no 4, p. 733-745Article in journal (Refereed)
    Abstract [en]

    Comparisons of release rates, duration in the field, and catch efficiency of polyethylene and cotton roll dispensers for the sex pheromones of sawflies (Hymenoptera: Diprionidae) were conducted. The release rates of the Neodiprion sertifer (Geoffr.) and Diprion pini (L.) sex pheromones, the acetates of pentadecanol and (2S,3S,7S)-3,7-dimethyl (2S,3R,7R)-3,7-dimethyl-2-tridecanol from polyethylene dispensers were measured at different temperatures in the laboratory. The release rates for the substances depended on both the temperature and initial load in the vials. The catch from cotton rolls baited with 100 μg of the acetate or propionate of 3,7-dimethyl-2-pentadecanol was compared to the catch from regularly renewed cotton rolls baited with 10 μg of the same acetate. The catch was higher for the 100-μg cotton rolls for, at most, 45 days, and there was no significant difference in catch between the acetate and the propionate. The catch in traps baited with polyethylene or cotton roll dispensers loaded with the acetate of 3,7-dimethyl-2-pentadecanol was compared and showed that cotton roll traps mirrored the decreasing release of the substance rather than the actual flight activity. The length of the flight period of N. sertifer in Sweden, the Czech Republic, Italy, and Greece did not exceed 100 days in any of the countries. By adjusting the initial pheromone load of the polyethylene vials to the expected temperatures, it should be possible to get a constant and sufficiently high release rate during the entire flight period.

  • 40.
    Kännaste, Astrid
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Nordenhem, Henrik
    Department of Ecology, Swedish University of Agricultural Sciences.
    Nordlander, Göran
    Department of Ecology, Swedish University of Agricultural Sciences.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Volatiles from a Mite-Infested Spruce Clone and Their Effects on Pine Weevil Behavior2009In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 35, no 10, p. 1262-1271Article in journal (Refereed)
    Abstract [en]

    Induced responses by Norway spruce (Picea abies) seedlings to feeding damage by two mite species were studied by analyzing the volatiles emitted during infestation. Four specimens of a Norway spruce (Picea abies L.) clone were infested with mites of Nalepella sp., another four with Oligonychus ununguis, and four were kept mite-free as controls. After a year of infestation, spruce volatiles were collected, analyzed, and identified using SPME-GC-MS. In addition, enantiomers of chiral limonene and linalool were separated by two-dimensional GC. Methyl salicylate (MeSA), (-)-linalool, (E)-beta-farnesene, and (E,E)-alpha-farnesene were the main volatiles induced by both species of mites, albeit in different proportions. The ability of the main compounds emitted by the mite-infested spruces to attract or repel the pine weevil, Hylobius abietis (L.), was tested. (E)-beta-farnesene was found to be attractive in the absence of spruce odor, whereas methyl salicylate had a deterrent effect in combination with attractive spruce odor. The other tested compounds had no significant effects on the behavior of the weevils.

  • 41.
    Lanne, B. S.
    et al.
    Gothenburg University.
    Schlyter, F.
    SLU, Alnarp.
    Byers, J. A.
    SLU, Alnarp.
    Lofqvist, J.
    SLU, Alnarp.
    Leufven, A.
    Gothenburg University.
    Bergstrom, G.
    Gothenburg University.
    Vanderpers, J. N. C.
    Unelius, C. Rikard
    KTH, Stockholm.
    Baeckstrom, P.
    KTH, Stockholm.
    Norin, T.
    KTH, Stockholm.
    Differences in Attraction to Semiochemicals Present in Sympatric Pine Shoot Beetles, (Coleoptera, Scolytidae) Tomicus minor and Tomicus piniperda1987In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 13, no 5, p. 1045-1067Article in journal (Refereed)
  • 42.
    Larsdotter Mellström, Helena
    et al.
    Stockholm University, Faculty of Science, Department of Zoology.
    Murtazina, Rushana
    KTH - Royal Institute of Technology, School of Chemical Science.
    Borg-Karlson, Anna-Karin
    KTH - Royal Institute of Technology, School of Chemical Science.
    Wiklund, Christer
    Stockholm University, Faculty of Science, Department of Zoology.
    Timing of Male Sex Pheromone Biosynthesis in a Butterfly –  Different Dynamics under Direct or Diapause Development2012In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 38, no 5, p. 584-591Article in journal (Refereed)
    Abstract [en]

    The life history traits and behavior of the butterfly are well-known, as the species is often used as a model organism for evolutionary and ecological studies. The species has two or more generations per year in the major part of its temperate distribution, and as different selection pressures affect the different generations, both behavioral and physiological seasonal polyphenisms have been shown previously. Here, we explored the dynamics of male sex pheromone production. The two generations are shown to have significantly different scent compositions early in life; the direct developers-who have shorter time for pupal development-need the first 24 hr of adult life after eclosion to synthesize the sex pheromone citral (geranial and neral 1:1)-whereas the diapausing individuals who have spent several months in the pupal stage eclose with adult scent composition. Resource allocation and biosynthesis also were studied in greater detail by feeding butterflies C-13 labeled glucose either in the larval or adult stage, and recording incorporation into geranial, neral, and other volatiles produced. Results demonstrate that the pheromone synthesized by newly eclosed adult males is based on materials ingested in the larval stage, and that adult butterflies are able to synthesize the pheromone components geranial and neral and the related alcohols also from adult intake of glucose. In summary, our study shows that time-stress changes the timing in biosynthesis of the complete pheromone between generations, and underpins the importance of understanding resource allocation and the physiological basis of life history traits.

  • 43. Larsdotter-Mellström, Helena
    et al.
    Murtazina, Rushana
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wiklund, Christer
    Timing of Male Sex Pheromone Biosynthesis in a Butterfly - Different Dynamics under Direct or Diapause Development2012In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 38, no 5, p. 584-591Article in journal (Refereed)
    Abstract [en]

    The life history traits and behavior of the butterfly are well-known, as the species is often used as a model organism for evolutionary and ecological studies. The species has two or more generations per year in the major part of its temperate distribution, and as different selection pressures affect the different generations, both behavioral and physiological seasonal polyphenisms have been shown previously. Here, we explored the dynamics of male sex pheromone production. The two generations are shown to have significantly different scent compositions early in life; the direct developers-who have shorter time for pupal development-need the first 24 hr of adult life after eclosion to synthesize the sex pheromone citral (geranial and neral 1:1)-whereas the diapausing individuals who have spent several months in the pupal stage eclose with adult scent composition. Resource allocation and biosynthesis also were studied in greater detail by feeding butterflies C-13 labeled glucose either in the larval or adult stage, and recording incorporation into geranial, neral, and other volatiles produced. Results demonstrate that the pheromone synthesized by newly eclosed adult males is based on materials ingested in the larval stage, and that adult butterflies are able to synthesize the pheromone components geranial and neral and the related alcohols also from adult intake of glucose. In summary, our study shows that time-stress changes the timing in biosynthesis of the complete pheromone between generations, and underpins the importance of understanding resource allocation and the physiological basis of life history traits.

  • 44.
    Laska, Matthias
    et al.
    University of Munich Medical School.
    Höfelmann, Daniela
    Department of Medical Psychology University of Munich Medical School, Germany.
    Huber, Diana
    Department of Medical Psychology University of Munich Medical School, Germany.
    Schumacher, Marie
    Department of Medical Psychology University of Munich Medical School, Germany.
    The Frequency of Occurrence of Acyclic Monoterpene Alcohols in the Chemical Environment does not Determine Olfactory Sensitivity in Nonhuman Primates2006In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 32, no 6, p. 1317-1331Article in journal (Refereed)
    Abstract [en]

       Using a conditioning paradigm, the olfactory sensitivity of five spider monkeys, three squirrel monkeys, and three pigtail macaques for six acyclic monoterpene alcohols that differ markedly in their frequency of occurrence in plant odors was assessed. The results showed that: (1) all three primate species have a well-developed olfactory sensitivity for acyclic monoterpene alcohols; (2) squirrel monkeys are significantly more sensitive for members of this class of odorants than the other two species and are able to detect all six odorants at concentrations below 0.1 ppm; and (3) there is a lack of positive correlations between olfactory sensitivity and the abundance of the acyclic monoterpene alcohols in flower odors and etheric oils. The results lend support to the growing body of evidence that suggests between-species comparisons of the number of functional olfactory receptor genes or of neuroanatomical features are poor predictors of olfactory performance. The findings do not support the hypothesis that olfactory sensitivity for members of a chemical class may be related to the frequency of occurrence of such odorants in a species' chemical environment.

  • 45.
    Laska, Matthias
    et al.
    Linköping University, Department of Physics, Chemistry and Biology, Zoology . Linköping University, The Institute of Technology.
    Rivas Bautista, Rosa Mariela
    Instituto de Neuro-Etologia.
    Hernandez Salazar, Laura Teresa
    Instituto de Neuro-Etologia.
    Gustatory Responsiveness to Six Bitter Tastants in Three Species of Nonhuman Primates2009In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 35, p. 560-571Article in journal (Refereed)
    Abstract [en]

    Gustatory responsiveness of six adult squirrel monkeys, four spider monkeys, and five pigtail macaques to six bitter tastants was assessed in two-bottle preference tests of brief duration (2 min). Animals were given the choice between a 30-mM sucrose solution and defined concentrations of a bitter tastant dissolved in a 30-mM sucrose solution. With this procedure, Saimiri sciureus, Ateles geoffroyi, and Macaca nemestrina were found to significantly discriminate concentrations as low as 0.2, 0.05, and 0.1 mM quinine hydrochloride; 1, 1, and 0.05 mM caffeine; 20, 5, and 1 mM naringin; 5, 2, and 1 mM salicin; 0.01, 0.001, and 0.02 mM sucrose octaacetate; and 0.05, 0.01, and 0.5 mM denatonium benzoate, from the alternative stimulus. With the exception of naringin in the pigtail macaques, all three species rejected all suprathreshold concentrations of all bitter tastants tested. The spider monkeys and the pigtail macaques displayed the lowest taste avoidance thresholds with three of the six tastants each; in contrast, the squirrel monkeys displayed the highest taste avoidance thresholds with four of the six tastants. The across-tastant patterns of taste avoidance thresholds were identical in spider monkeys and squirrel monkeys; both species displayed the following order of sensitivity: sucrose octaacetate > denatonium benzoate > quinine hydrochloride > caffeine > salicin > naringin. All three primate species were more sensitive to the two artificial tastants (sucrose octaacetate and denatonium benzoate) compared to the four naturally occurring tastants. However, the concentrations detected by all three primate species with the four naturally occurring tastants are well below those reported in plants or arthropods consumed by these species suggesting that they may use bitterness as a criterion for food selection.

  • 46.
    Lundborg, Lina
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemical Engineering and Technology.
    Nordlander, Goran
    Bjorklund, Niklas
    Nordenhem, Henrik
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Methyl Jasmonate-Induced Monoterpenes in Scots Pine and Norway Spruce Tissues Affect Pine Weevil Orientation2016In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 42, no 12, p. 1237-1246Article in journal (Refereed)
    Abstract [en]

    In large parts of Europe, insecticide-free measures for protecting conifer plants are desired to suppress damage by the pine weevil Hylobius abietis (L.). Treatment with methyl jasmonate (MeJA), a chemical elicitor already used in crop production, may enhance expression of chemical defenses in seedlings in conifer regenerations. However, in a previous experiment, MeJA treatment resulted in substantially better field protection for Scots pine (Pinus sylvestris L.) than for Norway spruce (Picea abies (L.) Karst.). Hypothesizing that the variations may be at least due partly to volatiles released by MeJA-treated seedlings and their effects on pine weevil orientation, we examined tissue extracts of seedlings (from the same batches as previously used) by two-dimensional GC-MS. We found that the MeJA treatment increased contents of the monoterpene (-)-beta-pinene in phloem (the weevil's main target tissue) of both tree species, however, the (-)-beta-pinene/(-)-alpha-pinene ratio increased more in the phloem of P. sylvestris. We also tested the attractiveness of individual monoterpenes found in conifer tissues (needles and phloem) for pine weevils using an arena with traps baited with single-substance dispensers and pine twigs. Trap catches were reduced when the pine material was combined with a dispenser releasing (-)-beta-pinene, (+)-3-carene, (-)-bornyl acetate or 1,8-cineole. However, (-)-alpha-pinene did not have this effect. Thus, the greater field protection of MeJA-treated P. sylvestris seedlings may be due to the selective induction of increases in contents of the deterrent (-)-beta-pinene, in contrast to strong increases in both non-deterrent (-)-alpha-pinene and the deterrent (-)-beta-pinene in P. abies seedlings.

  • 47. Mozuraitis, R.
    et al.
    Buda, V.
    Liblikas, I.
    Unelius, C. R.
    Borg-Karlson, Anna-Karin
    KTH, Superseded Departments, Chemistry.
    Parthenogenesis, calling behavior, and insect-released volatiles of leafminer moth Phyllonorycter emberizaepenella2002In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 28, no 6, p. 1191-1208Article in journal (Refereed)
    Abstract [en]

    We proved that the leafminer moth Phyllonorycter emberizaepenella (Lepidoptera: Gracillariidae) reproduces by parthenogenesis of the thelytoky type. Despite a complete absence of males, parthenogenetically reproducing females diurnally demonstrated the calling posture normally used for releasing signaling compounds. Two compounds, which we collected from a calling female, were identified as potential sex pheromone components: (8E,10E)-8,10-tetradecadienyl acetate and (8E,10E)-8,10-tetradecadienol, the latter occurring only in trace amounts. In field experiments, no males were attracted to traps baited with either the potential sex pheromone or with virgin females. Both the pattern of behavior and the chemical characteristics of the pheromone of Ph. emberizaepenella species were similar to those known for Lepidoptera with the usual amphimictic mode of reproduction. Theoretical speculations that in thelytoky, where there is no need to find a sexual partner, the individuals would obtain certain advantages due to reduction in their sexual behavior, were, thus, not confirmed for Ph. emberizaepenella.

  • 48.
    Mozuraitis, R.
    et al.
    KTH, Sweden.
    Buda, V.
    Liblikas, I.
    KTH, Sweden.
    Unelius, C. Rikard
    Borg-Karlson, A. K.
    KTH, Sweden.
    Parthenogenesis, calling behavior, and insect-released volatiles of leafminer moth Phyllonorycter emberizaepenella2002In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 28, no 6, p. 1191-1208Article in journal (Refereed)
    Abstract [en]

    We proved that the leafminer moth Phyllonorycter emberizaepenella (Lepidoptera: Gracillariidae) reproduces by parthenogenesis of the thelytoky type. Despite a complete absence of males, parthenogenetically reproducing females diurnally demonstrated the calling posture normally used for releasing signaling compounds. Two compounds, which we collected from a calling female, were identified as potential sex pheromone components: (8E,10E)-8,10-tetradecadienyl acetate and (8E,10E)-8,10-tetradecadienol, the latter occurring only in trace amounts. In field experiments, no males were attracted to traps baited with either the potential sex pheromone or with virgin females. Both the pattern of behavior and the chemical characteristics of the pheromone of Ph. emberizaepenella species were similar to those known for Lepidoptera with the usual amphimictic mode of reproduction. Theoretical speculations that in thelytoky, where there is no need to find a sexual partner, the individuals would obtain certain advantages due to reduction in their sexual behavior, were, thus, not confirmed for Ph. emberizaepenella.

  • 49. Mozuraitis, Raimondas
    et al.
    Buda, V.
    Borg-Karlson, A-K.
    Ivinskis, P.
    Chemocommunication in Phyllonorycter ulmifoliella (HBN.) (Lepidoptera: Gracillariidae): Periodicity, Sex Pheromone, and Inhibitors1997In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 23, no 1, p. 175-189Article in journal (Refereed)
    Abstract [en]

    (Z)-10-Tetradecenyl acetate (Z10-14:OAc) from abdominal tip extracts of virgin females of the tentiform leafminer moth Phyllonorycter ulmifoliella (Lepidoptera: Gracillariidae) was identified by gas chromatography and mass spectrometry. The biological activity of the component was confirmed by field tests with synthetic compounds. As a sex pheromone component this ester is novel both in the family Gracillariidae and in the superfamily Gracillarioidea. Field trapping of P. ulmifoliella with synthetic Z10-14:OAc at dosages of 1 and 0.2 mg/dispenser led to catches of approximately 9000 and 3000 male moths, respectively. The attractivity of the Z10-14:OAc was strongly inhibited by a 10% admixture of either (Z)-9-tetradecenyl acetate (Z9-14:OAc), (E)-9-tetradecenyl acetate (E9-14:OAc), or (E)-11-tetradecenyl acetate (E11-14:OAc). Addition of 10% (E)-10-tetradecenyl acetate (E10-14:OAc) to the sex pheromone reduced attractivity, but significantly less than the inhibitors previously mentioned. The pheromone releasing (or ‘’calling”) behavior of virgin P. ulmifoliella females was recorded under laboratory conditions. Calling activity started about half an hour before lights-on and the maximum number of calling females was registered half an hour after the start of photophase. A high level of pheromone releasing activity lasted for about 2 hr and ceased about 5 hr after the start of photophase. Chemocommunication activity in the light period of day is assumed to be an adaptation which allows this phyllonoryctid to avoid inhibitors emitted as pheromones by many other species. A scheme of probable interactions by means of semiochemicals between P. ulmifoliella and other lepidopterans is presented and the appearance of Z10-14:OAc as a sex pheromone component in Lepidoptera during evolution of the order is discussed.

  • 50.
    Mozuraitis, Raimondas
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Buda, Vincas
    Intra- and Interspecific Activities of Semiochemicals from the Sex Pheromone Gland of the Welsh Clearwing, Synanthedon Scoliaeformis2013In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 39, no 8, p. 1066-1069Article in journal (Refereed)
    Abstract [en]

    Analysis of the sex pheromone gland of virgin Synanthedon scoliaeformis females by gas chromatography/mass spectrometry revealed six compounds structurally related to sex pheromone components of other clearwing moths: (E,Z)-2,13-octadecadienyl acetate (E2,Z13-18:OAc), (E,Z)-2,13-octadecadienol, octadecanol acetate, octadecanol, (Z,Z)-3,13-octadecadienyl acetate (Z3,Z13-18:OAc), and (Z)-13-octadecenyl acetate. Trapping tests demonstrated that E2,Z13-18:OAc is the sex pheromone of S. scoliaeformis and is essential for attracting males; addition of the other compounds did not enhance catch. Synanthedon scoliaeformis and S. tipuliformis are the only Palearctic clearwing moths whose distribution range and seasonal flight periods overlap and that are known to use E2,Z13-18:OAc in sex pheromonal communication. Hourly monitoring of male catches in traps revealed that sex pheromone communication in S. scoliaeformis and S. tipuliformis species follows different diurnal patterns. Z3,Z13-18:OAc, found in S. scoliaeformis females, is a known behavioral antagonist against S. tipuliformis males, while (E,Z)-3,13-octadecadienyl acetate, a minor sex pheromone component of S. tipuliformis, is an antagonist against S. scoliaeformis males. The effect of sex pheromones and antagonists, combined with different diurnal mate searching times, contribute to the specificity of sex communication channels in these two clearwing moth species.

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