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  • 1
    ISSN: 1573-1561
    Keywords: Dendroctonus ponderosae ; Coleoptera ; Scolytidae ; pheromones ; trans-verbenol ; ipsdienol ; allelochemicals ; mixed-function oxidases ; monooxygenase inhibitors
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Female and male mountain pine beetles,Dendroctonus ponderosae Hopkins, were treated topically with piperonyl butoxide or sesame oil, both of which are known to inhibit poly substrate monooxygenase activity. Beetles then exposed to vapors of the host monoterpenes α-pinene and myrcene were found to contain reduced levels of the pheromonestrans-verbenol and ipsdienol, as well as a buildup of monoterpene precursors. Polysubstrate monooxygenase enzymes appear to be at least partially responsible for the detoxification of host monoterpenes and for the production of terpene alcohol pheromones in this species.
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  • 2
    ISSN: 1573-1561
    Keywords: Dendroctonus ponderosae ; bark beetle ; Coleoptera ; Scolytidae ; myrcene ; aggregation pheromones ; ipsdienol ; myrcenol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Male mountain pine beetles,Dendroctonus ponderosae Hopkins, produced ipsdienol [97.0% ± 0.3S-(+)] and myrcenol (90.3% ± 4.0E) when exposed to myrcene vapors. Females which were exposed to myrcene vapors did not produce any ipsdienol, but did produce low levels of myrcenol (98.0% ± 0.7E). Neither sex produced detectable levels of ipsdienol or myrcenol when fed for 24 hr on lodgepole pine,Pinus contorta var.latifolia Engelmann. The sex-specific conversion of myrcene to ipsdienol and myrcenol suggests that these compounds may have behavioral significance within the species. In addition, the S-(+)-ipsdienol produced by maleD. ponderosae probably functions as a repellent allomone againstIps pini (Say).
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  • 3
    ISSN: 1573-1561
    Keywords: Dendroctonus ponderosae ; Ips paraconfusus ; Coleoptera ; Scolytidae ; pheromones ; terpene alcohols ; axenic-rearing ; bark beetles ; microorganisms
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Dendroctonus ponderosae Hopkins andIps paraconfusus Lanier of both sexes produced most of their complement of terpene alcohols at normal to elevated levels in the absence of readily culturable microorganisms. However, there was some evidence that microbial involvement may be required by maleI. paraconfusus to produce ipsenol and ipsdienol at normal levels. Increased levels of certain terpene alcohols found in axenically reared or streptomycin-fed beetles suggest that symbiotic microorganisms may be responsible for breaking down pheromones and other terpene alcohols. There was also evidence for microbial involvement in the production of the antiaggregation pheromone verbenone inD. ponderosae. This compound was not produced in quantifiable levels by axenically reared or streptomycin-fed beetles exposed to α-pinene as vapors or through feeding, but was found in wildD. ponderosae exposed to α-pinene through feeding on bolts of lodgepole pine,Pinus contorta var.latifolia Engelmann.
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  • 4
    ISSN: 1573-1561
    Keywords: Dendroctonus ponderosae ; Ips paraconfusus ; Coleoptera ; Scolytidae ; axenic rearing ; monoterpenes ; aggregation pheromones ; trans-verbenol ; exo-brevicomin ; ipsenol ; ipsdienol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Mountain pine beetles,Dendroctonus ponderosae Hopkins, and California five-spined ips,Ips paraconfusus Lanier, were reared axenically from surface-sterilized eggs on aseptic pine phloem. After 24 hr in host logs, axenip femaleD. ponderosae and maleI. paraconfusus produced the aggregation pheromones,trans-verbenol (D. ponderosae), and ipsenol and ipsdienol (I. paraconfusus). Emergent, axenically reared maleD. ponderosae contained normal amounts of the pheromoneexo-brevicomin. Axenic femaleD. ponderosae treated with juvenile hormone or exposed to vapors of α-pinene, produced the pheromonetrans-verbenol. By 25–35 days after eclosion, axenic females exposed to α-pinene vapors produced over six times as muchtrans-verbenol as wild females, suggesting that while microorganisms in wild females may producetrans-verbenol, they may also inhibit production of the pheromone or use it as a substrate.
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  • 5
    ISSN: 1573-1561
    Keywords: Dendroctonus ponderosae ; Ips pini ; Coleoptera ; Scolytidae ; pheromone ; bark beetle ; ipsdienol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In bioassays conducted with walking beetles in the laboratory (S)−(+)−, (R)-(−)-, and (±)-ipsdienol were attractive alone, but reduced the attraction of both sexes of the mountain pine beetle,Dendroctonus ponderosae Hopkins, to extracts of female frass. Field trapping studies indicated that attraction ofD. ponderosae to a stimulus composed of myrcene +trans-verbenol +exo-brevicomin was significantly reduced with the addition of (±)- and sometimes (S)-(±)-ipsdienol. Thus, (S)-(+)-ipsdienol produced by males of this species may act as an antiaggregation pheromone. (S)-(+)-Ips-dienol is thought to function as a repellent allomone against the pine engraver,Ips pini (Say), in regions whereI. pini utilizes (R)-(−)-ipsdienol as an aggregation pheromone. However, in southwestern British ColumbiaI. pini was attracted to the (±)-ipsdienol used in field bioassays ofD. ponderosae, a finding consistent with the production of both enantiomers byI. pini in this region. When presented with the ternary semiochemical bait forD. ponderosae, (±)-ipsdienol was not attractive toI. pini. Thus, the activity of (S)-(+)-ipsdienol as a repellent allomone againstI. pini seems to be replaced in southwestern British Columbia by the inhibitory effects of myrcene,trans-verbenol,exo-brevicomin, or some combination thereof.
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  • 6
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 16 (1990), S. 1385-1397 
    ISSN: 1573-1561
    Keywords: Dendroctonus ponderosae ; Coleoptera ; Scolytidae ; Hansenula capsulata ; Pichiapinus ; pheromones ; trans-verbenol ; verbenone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A variety of symbionts associated with bark beetles are capable of producing compounds that are used as pheromones by their hosts. We report that two yeasts associated withDendroctonus ponderosae Hopkins,Hansenula capsulata Wickerham, andPichiapinus (Hoist) Phaff, are capable of convertingcis- andtrans-verbenol efficiently into verbenone.trans-Verbenol, which is produced by femaleD. ponderosae, acts as an aggregation pheromone for this scolytid, while verbenone, which other studies have indicated that microbe-reducedD. ponderosae are incapable of producing, acts as an antiaggregation pheromone.D. ponderosae appears to rely primarily on microbial symbionts for terminating aggregation and mass attack on individual host trees.
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  • 7
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Rapid Communications in Mass Spectrometry 3 (1989), S. 225-229 
    ISSN: 0951-4198
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Physics
    Notes: Secondary-ion mass spectrometry, using Cs+ ion bombardment of solid and liquid matrices, has been implemented on a quadrupole ion trap. Tetraalkylammonium cations and protonated peptides, generated in an external source using a pulsed primary-ion beam, are injected into the ion trap where they are decelerated and trapped in the course of collisions with the helium bath gas. The contents of the trap are then examined by recording a mass spectrum using the mass-selective instability scan. To improve performance in the examination of these trapped ions, the technique of axial modulation is used to cause resonance ejection of ions from the trap during the mass-analysis step. The supplementary AC voltage applied to the end-caps causes resonant ejection of ions at qz values below those which correspond to the normal stability limit. This is demonstrated to increase the mass limit of a commercial ion trap from 650 Da to approximately 1300 Da with no loss in resolution or sensitivity, and to more than 20 000 Da at reduced sensitivity.
    Additional Material: 7 Ill.
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  • 8
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Low energy collision induced dissociation (CID) spectra were measured by a triple stage quadrupole mass spectrometer for the [MH]+ ions of diethyl and dimethyl esters of maleic, fumaric, citraconic and mesaconic acids. A very high degree of stereospecificity was observed for the geometrically isomeric diethyl esters. The cis esters give rise to very abundant [MH—EtOH]+ and [MH—EtOH—C2H4]+ ions, while the trans isomers exhibit very abundant [MH—C2H4]+ and [MH—2 C2H4]+ ions. The highly stereospecific processes indicate that the double bond configuration is retained in the protonated species under the conditions of the experiment.
    Additional Material: 4 Ill.
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  • 9
    Electronic Resource
    Electronic Resource
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 7 (1973), S. 441-448 
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: CI mass spectra of the five isomeric vicinal d2-decanes have been recorded using methane and d4-methane as reagent gases. In contrast to earlier suggestions, we find that a large fraction of the alkyl fragment ions from n-decane are formed by elimination of olefins from the abundant [M - 1] ion. Only the C9 and C8 fragment ions are produced completely by a one-step reaction between the decanes and the methane reagent ions. Isotope exchange does not occur between the hydrocarbon and the reagent ions derived from d4-methane but extensive scrambling of the deuterium label in the d2-decanes does take place in the [M - 1] ion.
    Additional Material: 1 Ill.
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  • 10
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Low energy collision induced dissociation (CID) spectra indicate that m/z 173 ions formed by the loss of a halogen atom from diethyl chloro- and bromo-succinate under electron impact are mixtures of O-protonated diethyl maleate (〉90%) and fumarate (〈10 %). Hydrogen migration precedes the C-halogen bond cleavage in these cases. The low energy CID spectrum of the m/z 173 [M—I]+ ion obtained from diethyl iodosuccinate shows that only a small fraction of the [M—I]+ ions are the O-protonated species formed by hydrogen migration. The results of this study demonstrate the potential of low energy CID in the determination of structure (including configuration) of gas phase ions.
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