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  • 1
    Electronic Resource
    Electronic Resource
    Palo Alto, Calif. : Annual Reviews
    Annual Review of Entomology 48 (2003), S. 425-453 
    ISSN: 0066-4170
    Source: Annual Reviews Electronic Back Volume Collection 1932-2001ff
    Topics: Biology
    Notes: Abstract Recent application of biochemical and molecular techniques to study the genesis of scolytid aggregation pheromones has revealed that bark beetles are primarily responsible for the endogenous synthesis of widely occurring pheromone components such as ipsenol, ipsdienol, and frontalin. Because many of the chemical signals are isoprenoids, the roles of the mevalonate biosynthetic pathway and the enzyme HMG-CoA reductase (HMG-R) have been investigated. This has led to the identification of endothelial cells in the anterior midgut as the site of synthesis and to the concept that de novo pheromone biosynthesis is regulated in part by the positive effect of juvenile hormone III (JHIII) on gene expression for HMG-R. Both the pronounced regulation by JHIII and the expression pattern of eukaryotic HMG-R argue against synthesis of these pheromones by prokaryotes. As the mevalonate pathway and its regulation have been studied in few other insects, broader issues addressed through the study of scolytid pheromone biosynthesis include major step versus coordinate regulation of the pathway and a genomics approach to elucidating the entire pathway and the mode of action of JHIII.
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  • 2
    ISSN: 1432-1904
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Natural Sciences in General
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 1573-1561
    Keywords: Coleoptera ; Scolytidae ; Cleridae ; Trogositidae ; Pteromalidae ; Ips pini ; Dendroctonus brevicomis ; Enoclerus lecontei ; Enoclerus sphegeus ; Temnochila chlorodia ; Tomicobia tibialis ; ipsdienol ; lanierone ; aggregation pheromone ; kairomone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Five doses of lanierone (2-hydroxy-4,4,6-trimethyl-2,5-cyclohexadien-1-one) were tested with one dose of enantiomerically pure [99.4% (4R)-(−)] ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol) for activity as an aggregation pheromone ofIps pini (Say) in California. The response ofI. pini to 1 mg/day ipsdienol + 20 μg/day lanierone was significantly greater than the response to ipsdienol alone, but the response pattern did not demonstrate a clear dose-response relationship. The response to the highest dose of lanierone (2 mg/day) was significantly lower than the response to ipsdienol alone. Ipsdienol attracted significantly moreI. pini than a male-infested log. Lanierone did not alter the percentage of maleI. pini responding to ipsdienol alone. Neither sex ofI. pini orDendroctonus brevicomis LeConte from California produced detectable amounts of lanierone, but myrcene-aerated maleD. brevicomis produced 97.8%-(4S)-(+)-ipsdienol. The black-bellied clerid,Enoclerus lecontei (Wolcott) (Coleoptera: Cleridae) was attracted to lanierone when released with ipsdienol. Neither compound was attractive when released alone, proving synergism for the kairomone of this predator. Lanierone did not influence the response of the predatorsTemnochila chlorodia (Mannerheim) (Coleoptera: Trogositidae) andEnoclerus sphegeus (F.) (Coleoptera: Cleridae), which were attracted to all treatments containing ipsdienol.Tomicobia tibialis Ashmead (Hymenoptera: Pteromalidae) responded in significantly greater numbers to the male-infested log than it did to ipsdienol or ipsdienol + 20 μg/day lanierone.
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  • 4
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 21 (1995), S. 1229-1232 
    ISSN: 1573-1561
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
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  • 5
    ISSN: 1573-1561
    Keywords: Insecta ; Coleoptera ; Scolytidae ; Ips pini ; Ips avulsus ; Ips bonanseai ; ipsdienol ; 2-methyl-6-methylene-2,7-octadien-4-ol ; aggregation pheromone ; enantiomeric composition
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Thirty-five populations ofIps pini (Say) and one population each ofIps avulsus (Eichhoff) andIps bonanseai (Hopkins) were analyzed for the enantiomeric composition of ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol). Populations ofI. pini occur as at least two distinct regional pheromone variants: New York type [32%-(−) to 56%-(−)-ipsdienol] and California type [94%-(−) to 98%-(−)-ipsdienol]. A third phenotype may occur in southeastern British Columbia, Idaho, and Montana [91%-(−) to 95%-(−)], possibly indicating a zone of hybridization. Populations of the New York type occur in southwestern British Columbia, Alberta, Saskatchewan, Minnesota, and Wisconsin suggesting a continuum through the Canadian provinces and Lake States. The presence of the New York type in western Canada is likely linked to the Quaternary history of the transcontinentally distributed host,Pinus banksiana Lamb. MaleI. avulsus [∼25%-(−)] and maleI. bonanseai [−29%-(−)] both produce ipsdienol, but not ipsenol. Production of ipsdienol by maleI. pini was evaluated in six differentPinus spp. hosts. Following transfer of maleI. pini to hosts other than the host of origin, the percentage of the (−)-enantiomer of ipsdienol declined when compared to production in the host of origin.
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  • 6
    ISSN: 1573-1561
    Keywords: Ips paraconfusus ; Coleoptera ; Scolytidae ; bark beetle ; verbenone ; aggregation pheromone ; interruption ; Pinus radiata ; enantio-specific response
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The aggregation pheromone produced by maleIps paraconfusus (Coleoptera: Scolytidae) tunneling in Monterey pine,Pinus radiata, logs was trapped on Porapak Q. A concentration of an extract of trapped volatiles that attracted beetles was determined in the laboratory through a concentration–response analysis of walking behavior of males and females. The interruptant effects of four concentrations of verbenone on response to a constant concentration of this naturally produced aggregation pheromone were tested with males and females. Independent of its enantiomeric composition [99.5% (S)-(−), 93.1 % (S)-(−), and 98.3% (R)-(+)], verbenone significantly reduced the percentage of females (but not males) reaching the attractant source. However, when the time required for beetles of both sexes taken together to reach the attractant source was considered, verbenone of higher enantiomeric purity had a greater effect on beetle behavior. Solutions of 99.5% (S)-(−)- and 98.3% (R)-(+)-verbenone increased the time required for beetles to reach the attractive source when compared to 93.1% (S)-(−)-verbenone. When pooled across enantiomeric blends, increasing concentrations of verbenone resulted in slower responses in beetles that reached the attractant source within 2 min. Males and females did not respond to verbenone alone.
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  • 7
    ISSN: 1573-1561
    Keywords: Scolytidae ; Ips ; Orthotomicus ; Pinus ; evolution ; cuticular hydrocarbons ; chemotaxonomy ; methyl-branched hydrocarbons ; mass spectrometry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Cuticular hydrocarbons were extracted, identified, and evaluated as chemotaxonomic characters from all species of adult Ips pine engraver beetles in the grandicollis subgeneric group. The grandicollis group consists of Ips grandicollis (Eichhoff), I. cribricollis (Eichhoff), I. lecontei Swaine, I. montanus (Eichhoff), I. paraconfusus Lanier, I. confusus (LeConte), and I. hoppingi Lanier. In order to provide outgroups for a phylogenetic analysis, cuticular hydrocarbons were also analyzed from Orthotomicus caelatus (Eichhoff), I. latidens (LeConte) (latidens subgeneric group), and I. pini (Say) (pini subgeneric group). Two hundred forty-eight hydrocarbon components were identified by gas chromatography–mass spectrometry. The members of the grandicollis group provided 206 of these compounds. The components represented eight classes: n-alkanes, alkenes, alkadienes, terminally branched methylalkanes, internally branched methylalkanes, dimethylalkanes, trimethylalkanes, and tetramethylalkanes. Different populations of O. caelatus, I. grandicollis, I. lecontei, I. montanus, I. paraconfusus, I. confusus, and I. hoppingi provided no evidence for interpopulational variation in cuticular hydrocarbons. Single populations only were analyzed for I. latidens, I. pini, and I. cribricollis. Sexual dimorphism in cuticular hydrocarbons occurred only in I. lecontei where females produced eight unique components with a pentatriacontane parent chain. Several phylogenetic analyses based on hydrocarbon phenotypes agreed in general with the established morphologically based system of relatedness and with published phylogenies reconstructed from protein and nucleic acid characters. Nearly all hydrocarbon analyses suggested a close relationship between I. grandicollis and I. cribricollis; between I. lecontei and I. montanus; and among the sibling species I. paraconfusus, I. confusus, and I. hoppingi. The presence or absence of specific n-alkanes (n-docosane, n-triacontane); certain dimethylalkanes (terminally branched with octacosane and triacontane parent chains and internally branched with heptacosane, hentriacontane, and docotriacontane parent chains); and 3,7,11-; 3,7,15-trimethylheptacosane permit facile discrimination of I. paraconfusus, I. confusus, and I. hoppingi. These three sibling species are difficult to resolve by external morphology. These data support the species status of I. hoppingi rather than it being considered a host race of the I. confusus complex. They also support the species status of I. cribricollis rather than it being considered part of I. grandicollis. In contrast to other published phylogenies reconstructed from molecular data, phylogenies reconstructed from cuticular hydrocarbons repeatedly place I. lecontei as an integral part of the grandicollis subgeneric group. Thus, cuticular hydrocarbon and pheromone alcohol composition of I. lecontei support its inclusion in the grandicollis subgeneric group.
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  • 8
    ISSN: 1573-1561
    Keywords: Ips plastographus maritimus ; Coleoptera ; Scolytidae ; bark beetle ; Pinus radiata ; host volatiles ; aggregation pheromone ; sex-specific response ; attraction ; interruption
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Attraction of both sexes ofIps plastographus maritimus Lanier to bark-phloem-xylem discs of Monterey pine,Pinus radiata D. Don, was demonstrated in the laboratory. Increasing concentrations of male and female volatiles trapped separately and released in a one-to-one ratio decreased attraction for both sexes combined. Attraction of both sexes to volatiles derived from males and females tunneling together in a one-to-one ratio increased with increasing concentration of extract. Attraction of males and females to male-infested discs and to trapped male volatiles increased with increasing dose of males or male extract. Attraction of males and females to female-infested discs and to trapped female volatiles was also demonstrated. The presence of females in male galleries reduced the attractiveness of infested disks to both sexes combined. Increasing numbers of females, tunneling separately from males in the same disc, reduced attraction of males, but not females. When a constant attractive dose of male volatiles was released with increasing doses of female volatiles, there was no difference in response of either sex when female volatiles were present compared with the response to male volatiles alone. When a constant attractive dose of male volatiles was released with increasing concentrations of volatiles derived from males and females tunneling together in a one-to-one ratio, attraction ofI. p. maritimus decreased. Response of females was frequently higher than that of males to the same attractant source. Hence, both sexes produce an attractant, and both sexes tunneling together in the same gallery reduce attraction of males and females to an attractive dose of male attractant.
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  • 9
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 19 (1993), S. 1809-1831 
    ISSN: 1573-1561
    Keywords: Coleoptera ; Scolytidae ; Ips ; enantiomeric composition ; chirality ; aggregation pheromone ; pheromone biosynthesis ; Ips pini ; Ips paraconfusus ; cis-verbenol ; cis-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol ; ipsenol ; 2-methyl-6-methylene-7-octen-4-ol ; ipsdienol ; 2-methyl-6-methylene-2,7-octadien-4-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract There has been a renaissance of interest in the significance of enantiomeric composition in biological systems. Three chiral monoterpene alcohol aggregation pheromone components (ipsenol, ipsdienol, andcis-verbenol) commonly isolated from engraver beetles (Ips spp.) provide a paradigm for this theme as it relates to olfactory-guided insect behavior. The literature pertaining to this system is reviewed and the effects of the enantiomeric composition of these semiochemicals on theIps spp. community is explored on two trophic levels. Hypotheses generated from the well-studied aggregation pheromone production and response patterns forI. paraconfusus Lanier andI. pini (Say) are generalized to the North American species in the genus. Despite the progress withI. paraconfusus andI. pini, substantial deficiencies exist in our understanding of the role of enantiomeric composition in pheromonal/allomonal effects in different subgeneric groups, in the regulation and mechanisms of stereoselective biosynthesis of the monoterpene alcohols, and in the benefits derived by individual insects that produce relatively large proportions of inactive or interruptive enantiomers with attractive enantiomers.
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  • 10
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