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  • 1
    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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  • 2
    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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    Paper (German National Licenses)
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