ChemInform Abstract: CONSTITUENTS OF THE VENOM OF A SOUTH AFRICAN FIRE ANT (SOLENOPSIS PUNCTATICEPS). 2,5‐DIALKYLPYRROLIDINES AND ‐PYRROLINES, IDENTIFICATION AND SYNTHESIS

Pedder, D.; Fales, Henry M.; Jaouni, T.; Blum, Murray S.; MacConnell, John G.; Crewe, Robin M.

doi:10.1002/chin.197702342

Cited by 5 publications

(6 citation statements)

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“…Furthermore, base peak m / z 83 of 26′ is in agreement with base peak m / z 97 of 2-ethyl-5-undecyl-Δ 1,2 -pyrroline with difference of a CH 2 . 2-Ethyl-5-pentyl-Δ 1,2 -pyrroline identified from South African fire ant ( Solenopsis punctaticeps ), however, has intense mass peaks m / z 82, 96, 97, 110, 111 with m / z 96 as base peak . Similarly, the base peak at m / z 83 and two weak ions at m / z 98, 110 in 28′ suggest the absence of a double bond in the pyrrolidine ring.…”

Section: Resultsmentioning

confidence: 99%

Reduction of Venom Alkaloids in Solenopsis richteri × Solenopsis invicta Hybrid: An Attempt To Identify New Alkaloidal Components

Chen

Fadamiro

2010

J. Agric. Food Chem.

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The alkaloid chemistry of the venom of hybrid fire ant, Solenopsis richteri × Solenopsis invicta, was investigated using silica gel chromatography and GC-MS techniques. In addition to most cis alkaloids of parental species, S. richteri Forel and S. invicta Buren, the cis alkaloid fraction of the body extract of hybrid fire ants also contains five significant new alkaloids. Hydrogenation of the cis alkaloid fraction yielded only five piperidines, 4', 12', 12, 20', and 20. Sodium borohydride and lithium aluminum hydride selectively reduced C═N double bond in piperideine alkaloids to give a mixture of cis and trans piperidines. However, reduction of the five new components yielded several new peaks with much longer retention times and increasing molecular weights over 30. It is evident that the chemical identities of the five new peaks are quite different from those known piperidines or piperideines found in Solenopsis fire ants.

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Section: Resultsmentioning

confidence: 99%

Reduction of Venom Alkaloids in Solenopsis richteri × Solenopsis invicta Hybrid: An Attempt To Identify New Alkaloidal Components

Chen

Fadamiro

2010

J. Agric. Food Chem.

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“…Pedder et al (1976) have identified an extensive series of unsymmetrical 2,5-dialkylpyrrolidines and pyrrolines in the venom of Solenopsis punctaticeps, a species closely related to the thief ants. Pedder et al (1976) have identified an extensive series of unsymmetrical 2,5-dialkylpyrrolidines and pyrrolines in the venom of Solenopsis punctaticeps, a species closely related to the thief ants.…”

Section: Ant Venomsmentioning

confidence: 99%

“…While some of the proteinaceous venoms appear to be similar in their composition to wasp venoms (Cavill et al, 1964;Lewis and de la Lande, 1967), others contain a large number of enzymes in extraordinarily high concentrations (Schmidt and Blum, 1978). The presence of unsymmetrical 2,5-dialkylpyrrolidines in the venoms of Monomorium and other Solenopsis species (Ritter and Persoons, 1975;Pedder et al, 1976) underscores the potential for alkaloidal synthesis in the myrmicine venom gland. Unsymmetrical 2,6-dialkylpiperidines are the hallmark of Solenopsis venoms (MacConnell et al, 1971Brand et al, 1972), and these alkaloids are known to possess powerful pharmacological activities (Caro et al, 1957;Adrouny et al, 1959;Read et al, 1978).…”

Section: P Defensive Compounds Of the Social Hymenoptera-an Overviewmentioning

confidence: 99%

Defensive Mechanisms in the Social Hymenoptera

Hermann¹,

Blum²

1981

Social Insects

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“…Using alkaloid venoms, these species subdue prey colonies (Blum et al 1980) and steal their brood (Hölldobler 1973). These groups are present in all temperate and tropical biogeographic provinces (Bolton 1995); they possess venoms rich in alkaloids mostly comprised of piperidines, pyrrolidines, pyrrolines, and indolizidines (Gorman et al 1998; (Cavill et al 1976(Cavill et al ) et al 1982(Cavill et al , 1996Pedder et al 1976;Snyder et al 2009). The stimulation of detoxification behavior by both fire ant venom (composed of piperidines) and Monomorium minimum venom (composed of pyrrolidines and pyrrolines) suggests that the venom of a broad array of these brood raiding species is likely to elicit this behavior.…”

Section: Discussionmentioning

confidence: 97%

Widespread Chemical Detoxification of Alkaloid Venom by Formicine Ants

et al. 2015

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The ability to detoxify defensive compounds of competitors provides key ecological advantages that can influence community-level processes. Although common in plants and bacteria, this type of detoxification interaction is extremely rare in animals. Here, using laboratory behavioral assays and analyses of videotaped interactions in South America, we report widespread venom detoxification among ants in the subfamily Formicinae. Across both data sets, nine formicine species, representing all major clades, used a stereotyped grooming behavior to self-apply formic acid (acidopore grooming) in response to fire ant (Solenopsis invicta and S. saevissima) venom exposure. In laboratory assays, this behavior increased the survivorship of species following exposure to S. invicta venom. Species expressed the behavior when exposed to additional alkaloid venoms, including both compositionally similar piperidine venom of an additional fire ant species and the pyrrolidine/pyrroline alkaloid venom of a Monomorium species. In addition, species expressed the behavior following exposure to the uncharacterized venom of a Crematogaster species. However, species did not express acidopore grooming when confronted with protein-based ant venoms or when exposed to monoterpenoid-based venom. This pattern, combined with the specific chemistry of the reaction of formic acid with venom alkaloids, indicates that alkaloid venoms are targets of detoxification grooming. Solenopsis thief ants, and Monomorium species stand out as brood-predators of formicine ants that produce piperidine, pyrrolidine, and pyrroline venom, providing an important ecological context for the use of detoxification behavior. Detoxification behavior also represents a mechanism that can influence the order of assemblage dominance hierarchies surrounding food competition. Thus, this behavior likely influences ant-assemblages through a variety of ecological pathways.

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ChemInform Abstract: CONSTITUENTS OF THE VENOM OF A SOUTH AFRICAN FIRE ANT (SOLENOPSIS PUNCTATICEPS). 2,5‐DIALKYLPYRROLIDINES AND ‐PYRROLINES, IDENTIFICATION AND SYNTHESIS

Cited by 5 publications

References 1 publication

Reduction of Venom Alkaloids in Solenopsis richteri × Solenopsis invicta Hybrid: An Attempt To Identify New Alkaloidal Components

Reduction of Venom Alkaloids in Solenopsis richteri × Solenopsis invicta Hybrid: An Attempt To Identify New Alkaloidal Components

Defensive Mechanisms in the Social Hymenoptera

Widespread Chemical Detoxification of Alkaloid Venom by Formicine Ants

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