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  • 1
    Electronic Resource
    Electronic Resource
    Sex Pheromone of Glossina tachinoides: Isolation, Identification, and Synthesis (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 1563-1575 
    Details
    ISSN: 1573-1561
    Keywords: Tsetse fly ; sex stimulant ; pheromone ; hydrocarbon ; methylalkanes ; gas chromatography ; Diptera ; biting fly
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Study of lipids from male and female laboratory-reared flies led to the demonstration of a potent contact sex stimulant in extracts and cuticular hydrocarbons of the female tsetse fly Glossina tachinoides (Westwood) against conspecific males. Thin-layer and column chromatography indicated that extracts contained hydrocarbons and saponifiable lipids. Biological activity was found in the alkanes from females, including prominent branched-chain alkanes that were detected by gas chromatography (GC). The alkanes were separated and collected by preparative gas chromatography (GC), and only the 37-carbon region showed biological activity. GC–mass spectrometry showed the major peak contained a mixture of isomeric 11,23-, 13,25- plus a minor amount of 11,21-dimethylheptatriacontane. Two racemic isomers were synthesized, and bioassays showed that the greatest activity was possessed by the 11,23- isomer with somewhat less activity in 13,25-dimethyl heptatria-contane. Dose–response data showed ED50 at 5 μg per decoy with solvent-washed males, nonspecific females, or corks as decoys. These alkanes released sexual activity in males that comprised most of the behaviors released by a female fly of the same species.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1020967918594
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  • 2
    Electronic Resource
    Electronic Resource
    Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 643-648 
    Details
    ISSN: 1573-1561
    Keywords: Mosquito ; Culex pipiens fatigans ; Diptera ; Culicidae ; oviposition ; attractant ; pheromone ; chiral chromatography ; acetoxyhexadecanolide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 6-Acetoxy-5-hexadecanolide (Ia) in the oviposition attractant pheromone released from egg apical droplets of the mosquitoCulex pipiens fatigans Wied. is shown to be the (−)-(5R,6S)- enantiomer. Identification was by chromatography of the 6-trifluoroacetoxy derivatives of the natural pheromone and of the synthetic (−)-(5R,6S)- (Ib) and (+)-(5S,6R)- (IIb) enantiomers on a capillary column having a chiral stationary phase comprising a derivative of (1S,3S)-chrysanthemic acid. The synthetic (−)-(5R,6S)- enantiomer (Ia) attracted oviposition of four fold more mosquito egg rafts than the control (P 〈 0.01) whereas for the (5S,6R)- enantiomer (IIa) there was no statistically significant oviposition attraction.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00988573
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  • 3
    Electronic Resource
    Electronic Resource
    Sex-specific activity of (R)-(−)- and (S)- (+)-1,7-dioxaspiro[5.5]undecane, the major pheromone ofDacus oleae (1986)
    Springer
    Journal of chemical ecology 12 (1986), S. 1559-1568 
    Details
    ISSN: 1573-1561
    Keywords: Dacus oleae ; olive fruit fly ; Diptera ; Tephritidae ; pheromones ; enantiomers ; sex attractants ; sex-specific enantiomers
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 1,7-Dioxaspiro[5.5]undecane (olean), the major component of the female sex attractant pheromone blend of the olive fruit flyDacus oleae (Gmelin) was shown to be released as a racemate. The response of males and females to pure (R)-(−) and (S)-(+)-enantiomers was tested under laboratory and field conditions. Males in laboratory and field tests responded only to (R)-(−)-olean, which functions as a sex attractant. Females responded only to (S)-(+)-olean in laboratory tests but not in the field. There are indications that the latter enantiomer fuctions as a short-range arrestant throughout the day and as an aphrodisiac in the process of mating.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012372
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  • 4
    Electronic Resource
    Electronic Resource
    Dendroctonus pseudotsugae hopkins (Coleoptera: Scolytidae): Production of and response to enantiomers of 1-methylcyclohex-2-en-1-ol (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 1201-1208 
    Details
    ISSN: 1573-1561
    Keywords: Dendroctonus pseudotsugae ; Douglas-fir beetle ; Coleoptera ; Scolytidae ; aggregation pheromone ; production ; response ; methylcyclohexenol ; seudenol ; enantiomers ; trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Female Douglas-fir beetles,Dendroctonus pseudotsugae, produced an average 45∶55 mixture of the (S)-(−)- and (R)-(+)-enantiomers of 1-methylcyclohex-2-en-1-ol (MCOL). The (S)-(−)∶(R)-(+) ratio of 3-methylcyclohex-2-en-1-ol (seudenol) produced by this population of females was 34∶66. Lindgren funnel traps baited with (R)-(+)-MCOL attracted significantly more males and females than (S)-(−)-MCOL-baited traps, which captured significantly more beetles than unbaited controls. The combined effect of the enantiomers was additive, rather than synergistic. Either enantiomer of MCOL increased catches by frontalin-baited traps. Racemic MCOL can be used for trapping Douglas-fir beetles in south-central British Columbia.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00980074
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  • 5
    Electronic Resource
    Electronic Resource
    Southern pine beetle: Olfactory receptor and behavior discrimination of enantiomers of the attractant pheromone frontalin (1982)
    Springer
    Journal of chemical ecology 8 (1982), S. 873-881 
    Details
    ISSN: 1573-1561
    Keywords: Enantiomers ; bark beetle ; pheromone ; Dendroctonus frontalis ; Coleoptera ; Scolytidae ; southern pine beetle ; electrophysiology ; olfaction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In laboratory and field bioassays, the response ofDendroctonus frontalis was significantly greater to the mixture of (1S, 5R)-(−)-frontalin andalpha-pinene than to (1R,5S)-(+)-frontalin andalpfa-pinene. Electro-physiological studies revealed that antennal olfactory receptor cells were significantly more responsive to (1S, 5R)-(−)-frontalin than to (1R, 5S)-(+)-frontalin. Both enantiomers stimulated the same olfactory cells which suggests that each cell possesses at least two types of enantiomer-specific acceptors.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00994788
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  • 6
    Electronic Resource
    Electronic Resource
    Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2721-2735 
    Details
    ISSN: 1573-1561
    Keywords: Chirality ; enantiomers ; sex pheromones ; (3Z,9Z)-(6R,7S)-epoxynonadecadiene ; (3Z,9Z)-(6S,7R)-epoxynonadecadiene ; (6Z,9Z)-(3S,4R)-epoxynonadecadiene ; Colotois pennaria ; Erannis defoliaria ; Agriopis aurantiaria ; A. marginaria ; A. leucophearia ; Lepidoptera ; Geometridae ; electroantennogram ; field trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Enantiomer separation of (6Z,9Z)-cis-3,4-epoxynonadecadiene and (3Z,9Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3Z,9Z)-(6R,7S)-Epoxynonadecadiene was identified from ovipositor extracts ofColotois pen-Naria, while inErannis defoliaria the 6S,7R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3Z,6Z,9Z)-Nonadecatriene was found in both species, while the presence of (3Z,6Z,9Z)-heneicosatriene was indicated inC. Pennaria only. A 10∶10∶3 blend of (3Z,9Z)-(6R,7S)-epoxynonadecadiene, (3Z,6Z,9Z)-heneicosatriene, and (3Z,6Z,9Z)-nonadecatriene was found to be optimal for catchingC. Pennaria, whileE. Defoliaria males were optimally caught by a 1∶1 mixture of (3Z,9Z)-(6S,7R)-epoxynonadecadiene and (3Z,6Z,9Z)-nona-decatriene. (6Z,9Z)-(3S,4R)-Epoxynonadecadiene was identified from ovipositor extracts ofAgriopis (Erannis) aurantiaria. In field tests the pure enantiomer proved to be a highly specific sex attractant for both the late autumn/early winter flyingA. Aurantiaria and the late winter/early spring flyingA. Leucophearia. Males ofAgriopis marginaria, which fly in late winter/early spring, were attracted to (3Z,9Z)-(6S,7R)-epoxynonadecadiene. The addition of (3Z,6Z,9Z)-nonadecatriene to theS,R-enantiomer increased captures. Optimal catches were recorded with a 10∶3 epoxide-hydrocarbon blend. Enantiomer specificity in all species was confirmed in EAG measurements.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00980703
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