Biosynthesis of the Solenopsins, venom alkaloids of the fire ants

Leclercq, Sabine; Braekman, Jean Claude; Daloze, Désiré; Pasteels, Jacques; Meer, Robert K. Van der

doi:10.1007/bf01143328

Cited by 41 publications

(28 citation statements)

References 10 publications

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“…Piperideine 1,2 -C11 has been hypothesized to act as an intermediate in the interconversion of cis and trans ring isomers (Brand et al, 1972). Later, the piperideines, 1,6 -C11 and 1,2 -C11, were proposed to function as precursors for the biosynthesis of fire ant alkaloids, cis-and trans-C11 (Leclercq et al, 1996;Chen and Fadamiro, 2009a). The detected piperideines could be the result of the extraction process, which would halt the normal biosynthetic progression and trap piperideine biosynthesis intermediates.…”

Section: Discussionmentioning

confidence: 99%

“…Therefore, 5 and 6 were identified as 2-methyl-6-n-undecyl-1,6 -piperideine and 2-methyl-6-n-undecyl-1,2 -piperideine, respectively. Because piperideines were proposed to function as precursors for the syntheses of fire ant alkaloids (Leclercq et al, 1996;Chen and Fadamiro, 2009a) and the chirality of 2-CH 3 was always found to be R in Solenopsis fire ants (Pianaro et al, 2012), we inferred absolute configuration of 1,6 -piperideine (5) to be (2R)-CH 3 . However, both (6R)-and (6S)-C 11 H 23 configurations are possible for 1,2 -piperideine (6).…”

Section: Identification Of Alkaloids From Workers and Alate Queensmentioning

confidence: 99%

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Workers and alate queens of Solenopsis geminata share qualitatively similar but quantitatively different venom alkaloid chemistry

Shi

Wang

et al. 2015

Front. Ecol. Evol.

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Section: Discussionmentioning

confidence: 99%

Section: Identification Of Alkaloids From Workers and Alate Queensmentioning

confidence: 99%

Workers and alate queens of Solenopsis geminata share qualitatively similar but quantitatively different venom alkaloid chemistry

Shi

Wang

et al. 2015

Front. Ecol. Evol.

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“…Whereas S. invicta's venom has been the focus of many studies, its production and use have received relatively little attention beyond determination of the chemical nature of its biosynthesis (Leclercq et al, 1996) and the contexts of its use: prey capture (Hays and Hays, 1959;Blum and Callahan, 1960;Vinson and Sorenson, 1986;Lockley, 1995) and defense in response to disturbance (Blum, 1984;Vinson and Sorenson, 1986), competitors (Bhatkar et al, 1972;Obin and Vander Meer, 1985), and pathogens (Obin and Vander Meer, 1985). As a result, basic venom-related physiological and behavioral questions have remained largely unanswered.…”

Section: Introductionmentioning

confidence: 99%

Patterns of venom synthesis and use in the fire ant, Solenopsis invicta

Haight

Tschinkel

2003

Toxicon

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In the life of the fire ant, Solenopsis invicta, venom plays several important roles, including prey capture, defense, and antimicrobial action. Although this venom's chemistry, pharmacology, and effects on humans have been extensively studied, its patterns of synthesis and use have not. We determined the ability of different-aged workers to synthesize venom, and measured the amount of venom workers delivered per sting. Newly eclosed workers contained little or no venom in their reservoirs. The rate of synthesis was highest in workers aged 1 day after adult eclosion (1.17 mg venom/day for workers with headwidths of 1 mm), declined by 75% in workers aged 15 days (0.30 mg venom/day), and was negligible thereafter. Inducing ants to sting dummies as surrogates for humans, workers were found to deliver an average of 0.66 nl per sting, amounting to 3.1% of the average individual venom supply. Older workers (foragers) delivered less venom per sting than mid-age workers (reserves) and venom dose from nest-defenders was 55% higher in the spring than in the rest of the year. Thus, fire ant venom synthesis is limited to early life, and injected venom dose appears to be modulated. Economic explanations for the observed venom-use patterns are discussed. q

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“…Resulting alkaloids and cuticular hydrocarbons were identified by matching their retention indices and acquired mass spectra with entries in the internal mass spectra library (Wiley 275) and published literature [21,23,26,30], while the n-alkane external standards were used to bracket the retention indexes as whole numbers: 1600-3100 [26]. …”

Section: Retention Indexesmentioning

confidence: 99%

Intraspecific and Intracolonial Variation in the Profile of Venom Alkaloids and Cuticular Hydrocarbons of the Fire AntSolenopsis saevissimaSmith (Hymenoptera: Formicidae)

Fox

Pianaro

Solis

et al. 2012

Psyche: A Journal of Entomology

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Fire ants are aggressive Neotropical ants that are extensively similar in general biology and morphology, making species identification difficult. Some fire ant species are top-rated pests spreading throughout the world by trade vessels. Many researchers attempted to sort between invasive and native species by using chemical characters, including patterns of venom alkaloids. The present study is the first to report intraspecific variation in some chemical characters, namely, cuticular hydrocarbons and venom alkaloids, within the Brazilian fire ant species Solenopsis saevissima and also reports on within-nest variations among members of different castes. Two different haplotypes (cryptic species) of S. saevissima were clearly identified, one presenting a predominant combination of the venom alkaloids cis-and trans-2-methyl-6-undecylpiperidine with the cuticular hydrocarbons C 23 , 3-Me-C 23 , 10-C 25 : 1 , C 25 , and 3-Me-C 25 , and the other a predominant combination of cis-and trans-2-methyl-6-tridecenylpiperidine with predominance of 12-C 25 : 1 , C 25 , 11-Me-C 25 , 3-Me-C 25 , 13-C 27 : 1 , C 27 , and 13-Me-C 27 . Intranest variations revealed that the proportions among these compounds varied sensibly among workers of different sizes, gynes, and males (no alkaloids were detected in the latter). Larva contained vestiges of the same compounds. The recorded chemical profiles are quite different from previous reports with S. saevissima samples from São Paulo. The finds thus support other recent claims that S. saevissima includes cryptic species; the study, moreover, adds the find that they can occur in the same geographical location.

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Biosynthesis of the Solenopsins, venom alkaloids of the fire ants

Cited by 41 publications

References 10 publications

Workers and alate queens of Solenopsis geminata share qualitatively similar but quantitatively different venom alkaloid chemistry

Workers and alate queens of Solenopsis geminata share qualitatively similar but quantitatively different venom alkaloid chemistry

Patterns of venom synthesis and use in the fire ant, Solenopsis invicta

Intraspecific and Intracolonial Variation in the Profile of Venom Alkaloids and Cuticular Hydrocarbons of the Fire AntSolenopsis saevissimaSmith (Hymenoptera: Formicidae)

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