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  • 1
    Electronic Resource
    Electronic Resource
    Nest plundering allomones of the fire beeTrigona (Oxytrigona) mellicolor (1988)
    Springer
    Journal of chemical ecology 14 (1988), S. 495-501 
    Details
    ISSN: 1573-1561
    Keywords: Fire bee ; Trigona (Oxtrigona) mellicolor ; Trigona (Oxtrigona) tataira ; honeybee ; Apis mellifera ; Hymenoptera ; Apidae ; mandibular gland secretion ; allomone ; nest plundering ; diketones ; (E)-3-heptene-2,5-dione ; (E)-3-nonene-2,5-dione
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Ten volatile compounds derived from the cephalic glands of the fire beeTrigona (Oxytrigona)mellicolor were bioassayed for possible allomonal activities facilitating nest plundering. Two diketones, (E)-3-heptene-2,5-dione and (E)-3-nonene-2,5-dione, caused the honeybeeApis mellifera to display avoidance behavior and reduced defensive behavior. These diketones are produced in relatively large quantities in fire-bee cephalic glands.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01013901
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  • 2
    Electronic Resource
    Electronic Resource
    Venom chemistry of ants in the genusMonomorium (1982)
    Springer
    Journal of chemical ecology 8 (1982), S. 285-300 
    Details
    ISSN: 1573-1561
    Keywords: Monomorium spp. ; Hymenoptera ; Formicidae 2,5-dialkylpyrrolidines ; ant venom alkaloids ; methoxymercuration-demercuration ; chemotaxonomy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A comparative analysis of the venomous alkaloids produced by ant species in the subgenusMonomorium of the genusMonomorium has been undertaken. All species produce mixtures of unsymmetricaltrans-2,5-dialkylpyrrolidines, but the proportions of the constituents may vary considerably between species. All alkaloids contain both C6 and C9 side chains which are present as C9-saturated. C6-monounsaturated, and both C6-and C9-monounsaturated dialkylpyrrolidines. The structure of 2-(1-hex-5-enyl)-5-(1-non-8-enyl)pyrrolidine, a previously undescribed alkaloid, was proved by unambiguous synthesis after the location of the double bonds was established by the methoxymercuration-demercuration followed by mass spectrometry. The possible chemotaxonomic significance of the mixtures of venomous alkaloids produced by these species ofMonomorium is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984024
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  • 3
    Electronic Resource
    Electronic Resource
    Chemistry of venom alkaloids in the ant genusMegalomyrmex (1991)
    Springer
    Journal of chemical ecology 17 (1991), S. 1897-1908 
    Details
    ISSN: 1573-1561
    Keywords: Megalomyrmex ; Hymenoptera ; Formicidae ; venom ; alkaloids ; ants ; trans-2,5-dialkylpyrrolidine ; 3,5-dialkylpyrrolizidine ; Hofmann degradation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Chemical analyses of three species in the Neotropical ant genusMegalomyrmex have identified this taxon as the third myrmicine genus to produce alkaloids as major venom products. Workers ofM. leoninus and workers and ergatoids ofM. goeldii produce one or more of fourtrans-2,5-dialkylpyrrolidines previously identified in other myrmicine genera.M. modestus, on the other hand, is distinctive in producing the novel alkaloid (5E,8E)-3-butyl-5-hexylpyrrolizidine (5d), whose structure was established using a micro-Hofmann degradation sequence. The relationship ofMegalomyrmex to other alkaloid-producing ant genera is discussed along with the possible chemotaxonomic significance of the analyzed species when viewed in terms of the recognized species groups in this genus.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00993736
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  • 4
    Electronic Resource
    Electronic Resource
    Chemistry of cephalic secretion of fire beeTrigona (Oxytrigona) tataira (1984)
    Springer
    Journal of chemical ecology 10 (1984), S. 451-461 
    Details
    ISSN: 1573-1561
    Keywords: Fire bee ; Trigona (Oxytrigona) tataira ; Hymenoptera ; Apidae ; mandibular gland secretion ; enediones ; monoketones ; carboxylic esters ; hydrocarbons ; E-3-hepten-2,5-dione ; E-3-nonen-2,5-dione
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Analysis of the volatile compounds derived from cephalic glands of the fire beeTrigona (Oxytrigona) tataira by GC-MS was undertaken. The following compounds were readily identified: hydrocarbons:n-C11H24,n-C13H28,n-C14H30,n-C15H32,n-C17H36,n-C23H48,n-C15H30,n-C17H34,n-C21 H42, andn-C23H46; carboxylic acids: palmitic acid, linoleic acid, linolenic acid, stearic acid, and oleic acid; carboxylic esters: dodecyl acetate, tetradecyl acetate, hexadecyl acetate, octadecyl acetate, and dodecyl decanoate; monoketones: 5-hepten-2-one, 3-hepten-2-one, 2-heptanone, and 5-nonen-2-one. Two major components of the mixture were identified asE-hepten-2,5-dione andE-3-nonen-2,5-dione. Structures of these novel compounds were suggested by their GC-MS behavior and the GC-MS behavior of their dimethoximes and proved by comparison with authentic synthetic samples. Trace amounts of the corresponding Z isomers and the saturated analogs, heptan-2,5-dione and nonan-2,5-dione, were also found. The possible functions of these glandular constituents are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00988091
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  • 5
    Electronic Resource
    Electronic Resource
    Chemistry of mandibular and Dufour's gland secretions of ants in genusMyrmecocystus (1989)
    Springer
    Journal of chemical ecology 15 (1989), S. 2589-2599 
    Details
    ISSN: 1573-1561
    Keywords: Myrmecocystus species ; Hymenoptera ; Formicidae ; mandibular glands ; Dufour's gland ; chemosystematics ; sex pheromones ; defensive allomones ; methyl anthranilate ; citral ; methyl salicylate ; tridecyl esters
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Males of several species ofMyrmecocystus produce mandibular gland secretions that contain 2,4-dimethyl-2-hexenoic acid and a variety of monoterpenes that include neral, geranial, citronellol, limonene, and 2,6-dimethyl-5-hepten-1-ol. Other components identified include methyl anthranilate, octanal, octanol, octyl octanoate, and 2-hexyl-2-decenal. Methyl salicylate has been identified as a mandibular gland constituent of workers of several species in addition to mellein and monoterpenes such as cymene, limonene, and the isomers of citral. The Dufour's gland secretions of workers and females of 14 species contain typical formicine alkanes (e.g., undecane), 2-alkanols (e.g., 2-tridecanol), and 2-alkanones (e.g., 2-tridecanone). Two species in the subgenusEremnocystus produce secretions that are distinguished by the presence of significant quantities of tridecyl esters. The functions of these compounds as well as their possible chemosystematic significance in the genusMyrmecocystus are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01014734
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  • 6
    Electronic Resource
    Electronic Resource
    Mandibular gland allomones ofDasymutilla occidentalis and other mutillid wasps (1980)
    Springer
    Journal of chemical ecology 6 (1980), S. 895-903 
    Details
    ISSN: 1573-1561
    Keywords: Dasymutilla occidentalis ; Dasymutilla ; Timulla ; Pseudomethoca ; Smicromyrme ; Traumatomutilla ; Pappognatha ; Hymenoptera ; Mutillidae ; 4-methyl-3-heptanone ; 4,6-dimethyl-3-nonanone ; 4,6-dimethyl-3-octanone ; allomones
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The mandibular gland secretion of the mutillid wasp,Dasymutilla occidentalis, possesses three short-chained ketones-4-methyl-3-heptanone (4MH), 4,6-dimethyl-3-nonanone (4,6DMN), 4,6-dimethyl-3-octanone (4,6DMO)—and several unidentified compounds. This is the first report of 4,6DMN as a natural product and its synthesis is described. These ketones, which are either known to be ant alarm pheromones or are structurally very similar to ant alarm pheromones, appear to function as allomones against ants, major potential predators of mutillid wasps. The major secretory component, 4-methyl-3-heptanone, which was identified in females and/ or males of the species analyzed within the generaDasymutilla, Timulla, Traumatomutilla, andPappognatha, appears to constitute a chemical character of the defensive secretions of these genera.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00990473
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  • 7
    Electronic Resource
    Electronic Resource
    Honeybee nestmate recognition: Effects of queen fecal pheromones (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 1633-1640 
    Details
    ISSN: 1573-1561
    Keywords: Apis mellifera ; honeybee ; Hymenoptera ; Apidae ; queen ; fecal ; pheromones ; esters ; kin recognition
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Previous work has shown that queen honeybees,Apis mellifera, produce waxy esters composed of 8–14 carbon acids and 6–14 carbon alcohols in their feces. We tested these esters for effects on nestmate recognition; 11 of the 12 esters tested significantly modified the recognition characteristics of worker honeybees. Pairwise tests showed that workers can discriminate between at least some pairs of queen esters and that workers can discriminate between a queen ester and hexadecane (another known nestmate recognition cue). These results suggest that a queen may use the esters to enable workers to recognize her or to scent-mark her colony.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00993235
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