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  • 1
    Electronic Resource
    Electronic Resource
    Volatiles from mandibular glands of male beewolves (Hymenoptera: Sphecidae,Philanthus) and their possible roles (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 895-901 
    Details
    ISSN: 1573-1561
    Keywords: Philantus ; beewolf ; Sphecidae ; Hymenoptera ; pheromones ; scentmarking ; tridecanone ; pentadecanone ; heptadecanone ; hexadecanoic acid ; ethyl hexadecanoate ; octadecanoic acid ; ethyl octadecanoate ; mandibular glands ; wasps
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Observations of wasp behavior indicate that male beewolves,Philanthus basilaris andP. bicinctus apply a “marking pheromone” to the leaves and stems of plants within their territories. We now provide direct evidence for the presence of volatile chemicals in the paired mandibular glands of the males, provide preliminary identification of these volatiles, and show that all of the volatile chemicals in the mandibular glands are present on freshly marked plant surfaces but are absent from unmarked plants. Pyrazines, which have been reported in other species of aculeate wasps including the EuropeanPhilanthus triangulum, were not found inP. basilaris orP. bicinctus.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012076
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  • 2
    Electronic Resource
    Electronic Resource
    Chemistry of male mandibular gland secretions ofPhilanthus basilaris cresson andPhilanthus bicinctus (Mickel) (Hymenoptera: Sphecidae) (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 227-235 
    Details
    ISSN: 1573-1561
    Keywords: Philanthus ; Hymenoptera ; Sphecidae ; pheromone ; scent-marking ; 2-alkanones ; fatty acids ; ethyl esters ; alkenals ; N,N-dimethylhy-drazine ; methyl esters ; EI-MS ; CI-MS ; methoxymercuration ; methylthiolation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Detailed chemical characterizations are provided for the species-specific mixtures of marking pheromones utilized by the male beewolvesPhilanthus basilaris andP. bicinctus. Successful analysis of these complex mixtures of 2-ketones, fatty acids, ethyl esters, and aldehydes was facilitated by the treatment of the crude extracts with 1,1-dimethylhydrazine and direct analysis of the resulting hydrazones, methyl esters, and starting ethyl esters by GC-MS.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01025883
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  • 3
    Electronic Resource
    Electronic Resource
    Mandibular gland secretions of the male beewolvesPhilanthus crabroniformis, P. barbatus, andP. pulcher (Hymenoptera: Sphecidae) (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 27-37 
    Details
    ISSN: 1573-1561
    Keywords: Philanthus crabroniformis ; Philanthus barbatus ; Philanthus pulcher ; Hymenoptera ; Sphecidae ; beewolf ; mandibular glands ; pheromones ; semiochemicals ; mass spectrometry ; infrared spectroscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The composition of the territorial marking pheromones from mandibular glands of males of the beewolvesPhilanthus crabroniformis, P. barbatus, andP. pulcher have been determined. The structures of the components were elucidated by gas chromatography-mass spectrometry and gas chromatography-Fourier transform infrared spectroscopy. The major compound ofP. crabroniformis is isopropyl tetradecanoate, with somewhat lesser amounts of 2-tridecanone, 3-methyl-3-butenyl tetradecanoate, and 92∶8 (Z)∶(E)-11-eicosen-1-ol. The major compounds ofP. barbatus are ethyl tetradecanoate and hexadecanal, which are present in approximately a 60∶40 ratio. These two compounds comprise over 95% of the neutral lipids. Also present in lesser amounts are ethyl dodecanoate, tetradecanal, hexadecan-1-ol, a Δ x -octadecen-1-ol, and octadecan-1-ol. The major compounds ofP. pulcher are ethyl (Z)-7-hexadecenoate and geranylgeraniol acetate, which comprise nearly 90% of the neutral lipid fraction, with smaller amounts of tetradecanal, pentadecanal, and ethyl hexadecanoate; trace amounts of Δ x hexadecenal, hexadecanal, and octadecanal are also present.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00997162
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  • 4
    Electronic Resource
    Electronic Resource
    Chemistry of male mandibular gland secretions ofPhilanthus triangulum (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 2135-2143 
    Details
    ISSN: 1573-1561
    Keywords: Philanthus triangulum ; Hymenoptera ; Sphecidae ; Philanthinae ; beewolf ; (Z)-11-eicosen-1-ol ; 10-nonadecen-2-one ; nonadecenal ; eicosenal ; pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Males of the European and African beewolf,Philanthus triangulum, possess a sex specific mandibular gland secretion that is used for marking plant stems in mating territories. The secretion is composed of 90% (Z)-11-eicosen-1-ol plus small amounts of 10-nonadecen-2-one, nonadecenal, octadecanoic and octadecenoic acids, and eicosenal. The chemistry of this secretion differs markedly from the secretions of North AmericanPhilanthus, which consist of a larger number of components that possess different chemical functionalities and are more volatile. We postulate that the chemical differences betweenP. triangulum and its New World relatives reflect phylogenetic differences plus a possible reduced necessity for species isolating mechanisms inP. triangulum.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01026925
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  • 5
    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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  • 6
    Electronic Resource
    Electronic Resource
    Attraction of reproductive honey bee swarms to artificial nests by Nasonov pheromone (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1053-1056 
    Details
    ISSN: 1573-1561
    Keywords: Honey bee ; Apis mellifera ; Hymenoptera ; Apidae ; pheromone ; attractant ; Nasonov ; swarms ; citral ; geraniol ; nerolic acid ; geranic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A crossover experimental design was established to test the attractancy of Nasonov pheromone to reproductive swarms of honey bees. Nineteen swarms were attracted to artificial nest cavities containing a slow-release blend of the Nasonov components citral, geraniol, and nerolic + geranic acids, and only four swarms were attracted to pheromone-free artificial nests. The results indicate that Nasonov pheromone plays a key role in the attraction of honey bee swarms to nest cavities.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059741
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  • 7
    Electronic Resource
    Electronic Resource
    (Z)-11-Eicosen-1-ol, a Major Component of Apis cerana Venom (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1929-1939 
    Details
    ISSN: 1573-1561
    Keywords: (Z)-11-Eicosen-1-ol ; octadecanol ; eicosanol ; docosenol ; alarm pheromone ; venom ; Apis cerana ; Apis koschevnikovi ; Apis dorsata ; Apidae ; Hymenoptera
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The unusual venom of Apis cerana contains large oily droplets within an otherwise aqueous secretion. Chemical analysis (GC-MS) revealed that the venom oil consists of (Z)-11-eicosen-1-ol (81.2%), other linear alcohols (7.7%), and linear hydrocarbons (11.1%). The eicosenol is present in extremely large quantities, averaging over 250 μg per insect, and is absent, or present in small quantities, in other parts of the sting apparatus. An investigation of the site of eicosenol storage in A. mellifera showed it to be absent from the venom and to be associated with the setose area where the more volatile components of the alarm pheromone are stored, as previously shown by others. A third honeybee species, A. dorsata, does not to contain the alcohol. The function of eicosenol in A. cerana in not clear, but may serve to mark stung intruders with pheromone or to attract foragers to marked floral resources.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/B:JOEC.0000006480.49252.df
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