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  • 1
    ISSN: 1432-1351
    Keywords: Sex pheromone ; Electroantennogram ; Single sensillum ; Olfaction ; Diprionol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Electroantennographic and single sensillum recordings were performed on male pine sawfly, Neodiprion sertifer, antennae. Responses to the sex pheromone component (2S, 3S, 7S)- 3,7-dimethyl-2-pentadecenyl (diprionyl) acetate (SSS:OAc), to the behavioral inhibitor (2S, 3R, 7R)-diprionyl acetate (SRR:OAc), to the six other enantiomers of diprionyl acetate, and to the biosynthetic precursor diprionol were recorded. Responses to trans-perillenal, a monoterpene identified in female gland extracts and to (2S, 3S, 7S)-diprionyl propionate (SSS:OPr), a field attractant for N. sertifer and some related sawfly species were also recorded. EAG recordings demonstrated a high antennal sensitivity to SSS:OAc and to SSS:OPr. A somewhat lower response was elicited by SRR:OAc. Single sensillum recordings revealed 8–12 different cells firing in each sensillum, corresponding to the number of cells observed in earlier morphological investigations. Out of these cells all, except one, responded to SSS:OAc and to SSS:OPr. No differences in the response to the two components could be observed. The largest amplitude cell in each sensillum was specifically tuned to the behavioral antagonist, SRR:OAc. The pheromone perception system encountered in male pine sawflies thus differs clearly from that observed in moths.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1432-1904
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Natural Sciences in General
    Notes: Abstract  The main component of the sex pheromone precursor in females of Macrodiprion nemoralis was identified as a threo-3,7,9-trimethyl-2-tridecanol isomer, approximately 800 pg per female, by gas chromatography–mass spectrometry. Comparison of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time and mass spectrum as one of the two synthetic threo peaks. The acetate of the synthetic 16-isomer mixture caught a large number of males in the field, confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female extract with the eight synthetic threo stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 1420-9071
    Keywords: Diprion pini ; semiochemicals ; sex attractant ; 3,7-dimethyl-2-tridecanol ; chiral synthesis ; lipase ; chiral analysis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract The main component of the sex pheromone secretion of femaleDiprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as athreo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1–4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (〉99% ee) building blocks. The stereochemistry of the main component was established to be (2S,3R,7R)-3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a non-chiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 μg of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 μg in France and 50 μg in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.
    Type of Medium: Electronic Resource
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  • 4
    ISSN: 1570-7458
    Keywords: Hymenoptera ; Symphyta ; Diprionidae ; sawfly ; pest insect ; semiochemical ; chemical communication ; diprionol ; 3,7-dimethyl-2-pentadecanol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The European pine sawfly, Neodiprion sertifer (Geoffroy) (Hymenoptera: Diprionidae), is a widespread and economically important forest insect. The sex pheromone communication system of this species has been previously investigated in North America, Japan and Europe, with the acetate or propionate of the alcohol (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) shown to be the main pheromone component. In some locations, male attraction either increased or decreased by the addition of the (2S,3R,7R)-diprionyl acetate isomer. However, these studies were made with different batches of synthetic pheromones, with different types of traps and according to different procedures, so the observed differences might not reflect true geographic variation. Here we investigate the geographic pattern of male sawfly response by using identical chemicals, traps and experimental procedures at eight field sites ranging from Japan in the east to Canada in the west. We found an increased inhibitory effect of the (2S,3R,7R)-isomer from Japan and Siberia to Europe. At the eastern sites, increasing amounts of the (2S,3R,7R)-isomer up to and equal to the amount of the (2S,3S,7S )-isomer, did not influence the trap catch, whereas at sites in Europe, as little as 1% of the (2S,3R,7R)-isomer almost completely inhibited the attraction. The response of the North American population was intermediate. The only site in which the (2S,3R,7R)-isomer was essential for the attraction of males was in Siberia. A similar pattern was found for the (2S,3R,7S)-isomer. Both the acetate and the propionate form of the (2S,3S,7S)-isomer were attractive by themselves in Japan, Europe and North America, and neither the (2S,3R,7S)-isomer nor the (2S,3R,7R)-isomer alone were attractive, in the acetate or propionate form. We discuss the significance of our findings for the development of more efficient monitoring schemes and for the causes of population divergence and speciation in the European pine sawfly.
    Type of Medium: Electronic Resource
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  • 5
    ISSN: 1570-7458
    Keywords: Hymenoptera ; Diprionidae ; chiral compounds ; behavioural activity ; attractant ; inhibitor
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract All eight optical isomers of 3,7-dimethyl-2-pentadecanyl acetate (diprionyl acetate), of high optical purity (〉 97.4%), were tested for a behavioural activity on male pine sawflies, Neodiprion sertifer (Geoffr.) (Hymenoptera: Diprionidae), in northern Europe. Males were strongly attracted to (2S,3S,7S)-diprionyl acetate. Addition of more than 0.1% of the (2S,3R,7R)-isomer reduced the catch and above 2% the attraction was completely inhibited. Contrary to what has been reported for North American and Japanese populations, so significant synergistic effect of small amounts of the (2S,3R,7R)-isomer could be demonstrated. The effects of addition of the other six optical isomers alone or in combinations, were also studied, but none was found to be a synergist. The (2S,3R,7S)-isomer had a weak inhibitory effect, and completely inhibited the attraction to the (2S,3S,7S)-isomer when applied in about equal amounts as the attractant. In some cases a reduction in catch was noted when other isomers were tested, but this could be attributed to the very small amounts of the inhibitory (2S,3R,7R)-isomer present in these isomers.
    Type of Medium: Electronic Resource
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  • 6
    ISSN: 1573-1561
    Keywords: Ant lions ; Neuroptera ; Myrmeleontidae ; (R,Z)-6-tridecen-2-ol ; nerol oxide ; 10-homonerol oxide ; biosynthesis ; enantiomers ; gas chromatography-mass spectrometry ; sympatric species isolation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The thoracic glands of males in two ant-lion speciesSynclysis baetica andAcanthaclisis occitanica, which occur sympatrically in Israel, were found to contain a volatile secretion with two-component blends of nerol oxide and (R,Z)-6-tridecen-2-ol (approx 1∶5) and nerol oxide and 10-homonerol oxide (approx. 1∶2), respectively. Chemical analyses were performed using gas chromatography-mass spectrometry, chiral gas chromatography, and ozonolysis, and the proposed structures were confirmed by synthesis. The species-specific, few-component volatile signals are thought to function as a reproductive isolation mechanism between the two sympatric species. Biochemical relationships between the nerol derivatives and between the unsaturated secondary alcohols are discussed.
    Type of Medium: Electronic Resource
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