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  • 1
    Electronic Resource
    Electronic Resource
    Novel 2-ethyl-5-alkylpyrrolidines in the venom of an australian ant of the genusMonomorium (1988)
    Springer
    Journal of chemical ecology 14 (1988), S. 35-45 
    Details
    ISSN: 1573-1561
    Keywords: Ants ; Monomorium ; Hymenoptera ; Formicidae ; venom ; 2,5-dialkylpyrrolidines ; 2,5-dialkyl-1-pyrrolines ; dimethyldisulfide adducts ; insecticidal activity ; chemical ecology
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Novel 2-ethyl-5-alkylpyrrolidines and their corresponding 1-pyrrolines have been identified as poison gland products from an unidentified Australian species ofMonomorium. The major alkaloids present in the venom of this ant aretrans-2-ethyl-5-undecylpyrrolidine andtrans-2-ethyl-5-(12-tridecen-1-yl)pyrrolidine. The position of the double bond in the latter was established from its dimethyl-disulfide adduct after the amine function had been protected, and the stereochemistry of the alkyl groups was determined by direct comparison with synthetic compounds. The corresponding 1-pyrrolines were also detected in varying amounts in this venom. The pyrrolidines and 1-pyrrolines possess considerable insecticidal activity when evaluated against termite workers. The alkaloidal venoms ofMonomorium appear to be an important factor contributing to the success of these small ants both as competitors and as predators.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01022529
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  • 2
    Electronic Resource
    Electronic Resource
    Chemotaxonomic implications of the venom chemistry of someMonomorium “antarcticum” populations (1988)
    Springer
    Journal of chemical ecology 14 (1988), S. 2197-2212 
    Details
    ISSN: 1573-1561
    Keywords: Ants ; Monomorium ; Hymenoptera ; Formicidae ; 2,5-dialkylpyrrolidines ; 3,5-dialkylpyrrolizidines ; ant venom alkaloids ; chemotaxonomy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A comparative analysis of the venom alkaloids produced by ants in the genusMonomorium (= Chelaner) collected on North Island and South Island, New Zealand, has been undertaken. All of the ants producetrans-2, 5-dialkylpyrrolidines along with 3,5-dialkylpyrrolizidines. The structures and sterochemistry of the novel alkaloidstrans-2-butyl-5-(8-nonenyl) pyrrolidine, (5E,8Z)-3,5-di(5-hexenyl)pyrrolizidine, and (5Z,8E)-3-methyl-5-(8-nonenyl)pyrrolizidine were established by unambiguous synthesis. The geographic distribution and the chemotaxonomic significance of the alkaloids produced by these ants are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01014025
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  • 3
    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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  • 4
    Electronic Resource
    Electronic Resource
    Behavior and chemical disguise of cuckoo antLeptothorax kutteri in relation to its hostLeptothorax acervorum (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 1431-1444 
    Details
    ISSN: 1573-1561
    Keywords: Ants ; Formicidae ; Hymenoptera ; Leptothorax kutteri ; Leptothorax acervorum ; nestmate recognition ; ethograms ; gas chromatography
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Females of the obligately parasitic cuckoo ant,Leptothorax kutteri, a workerless inquiline, are among the only adult ants that can successfully invade ant societies and come to be accepted as a nestmate by the existing adult workers. This occurs even though the cuckoo ant is usually severely attacked by theLeptothorax acervorum workers of the colony that she is attempting to enter and parasitize. Through extensive ethogram studies of established parasites and parasitized and free-livingL. acervorum workers and queens, we show that theL. kutteri queen grooms host queens at an exceptionally high frequency. Possibly associated with this behavior, the established parasite is never attacked by theL. acervorum workers or queens she exploits. We show that there is exceptional similarity between the cuticular hydrocarbons and especially the cuticular fatty acids of the parasitic females and her nestmateL. acervorum workers, compared with nonnestmate workers and queens. We suggest that this matching of cuticular compounds may be associated with the grooming of host queens by the parasite. This in turn suggests the possibility that fatty acids have a role in colony-specific nestmate recognition in these and other ants and that grooming may serve for the dissemination of such substances throughout the colony.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01014079
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  • 5
    Electronic Resource
    Electronic Resource
    Phenylalkenals in ponerine(Leptogenys sp.) and myrmicine (Pogonomyrmex sp.) ants (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 847-854 
    Details
    ISSN: 1573-1561
    Keywords: Phenylalkenals ; Leptogenys spp ; Pogonomyrmex rugosus ; Hymenoptera ; Formicidae ; 2-phenylpropenal ; 2-phenyl-2-butenal ; 2,5-dimethyl-3-(1-methyl) butylpyrazine ; 2,5-dimethyl-3-isopentylpyrazine ; 2,5-dimethyl-3-isopentenyl-6-isopentylpyrazine ; 4-methyl-3-heptanone ; 5-methyl-3-hexanone ; Maillard reaction ; benzaldehyde ; chemoreceptors ; defensive allomones
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Cephalic extracts of two unrelated species of ants,Leptogenys processionalis andPogonomyrmex rugosus, have been found to contain 2-phenylpropenal and 2-phenyl-2-butenal, while two other species related to the first,L. chinensis andL. kitteli, lacked either.L. kitteli also produced a tetrasubstituted pyrazine found previously only in two New Zealand ants in the genusMesoponera. The chemical reactivity of the phenylalkenals suggests their function in repelling attack by predators.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00988325
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  • 6
    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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  • 7
    Electronic Resource
    Electronic Resource
    Volatile compounds from ponerine ants in the genusMesoponera (1984)
    Springer
    Journal of chemical ecology 10 (1984), S. 651-665 
    Details
    ISSN: 1573-1561
    Keywords: Hymenoptera ; Formicidae ; Mesoponera ; ants ; ponerine ants ; secondary and tertiary aliphatic amines ; formamides ; acetamides ; isovaleramides ; 2,6-dimethyl-3-isopentylpyrazine ; aliphatic aldehydes and acids ; phenylacetic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Volatile constituents have been characterized from two species of ponerine ants in the genusMesoponera. 2,5-Dimethyl-3-isopentyl-pyrazine has been identified from cephalic extracts ofM. castanea andM. castaneicolor, by gas chromatography-mass spectrometry. Combined gasters and thoraces of both species are also characterized by the presence of nonanal, nonanoic acid, isovaleric acid, phenylacetic acid, and undecanal, as well as a series of aliphatic amines and amides.N-Isoamylnonylamine was a major constituent that was accompanied byN-isoamylnonenylamine,N,N-diisoamylnonylamine,N-acetyl nonylamine,N-formyl isoamylnonylamine,N-isovaleroyl nonylamine, and several other secondary and tertiary amines. The possible significance of the amines and amides as idiosyncratic natural products ofMesoponera species is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00994226
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  • 8
    Electronic Resource
    Electronic Resource
    (5Z,9Z)-3-alkyl-5-methylindolizidines fromSolenopsis (Diplorhoptrum) species (1984)
    Springer
    Journal of chemical ecology 10 (1984), S. 1233-1249 
    Details
    ISSN: 1573-1561
    Keywords: Ants ; Solenopsis (Diplorhoptrum) species ; Monomorium pharaonis ; Hymenoptera ; Formicidae ; 3-alkyl-5-methylindolizidines ; alkaloids ; venom components ; 2,5-dialkylpyrrolidines
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The alkaloidal venom components of two species of thief ants,Solenopsis (Diplorhoptrum) species AA andS. (Diplorhoptrum)conjurata have been found to contain (5Z,9Z)-3-hexyl-5-methylindolizidine and a mixture of (5Z,9Z)-3-ethyl-5-methylindolizidine andcis-2-methyl-6-nonyl-piperidine,trans-2-methyl-6-nonylpiperidine,cis-2-methyl-6-undecylpiperidine, and hexadecanoic acid.Monomorium pharaonis was similarly investigated and found to contain the indolizidine and pyrrolidines previously described (Ritter et al., 1977b). Both indolizidines were synthesized along with their stereoisomers and separated by preparative gas chromatography. Spectral studies revealed the stereochemistry to be 5Z,9Z in both cases. The stereochemistry of 2-butyl-5-pentylpyrrolidine inM. phaeronis has also been established. Biosynthetic relationships are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00988551
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