Constituents of the venom of a south african fire ant (solenopsis punctaticeps)

Anabaseine: Venom Alkaloid of Aphaenogaster Ants

“…We also reported that suspensions of epidermal cells, applied to the contracted lattices in vitro, cover them rapidly and differentiate thereon (2). The epidermis becomes multilayered and undergoes keratinization.…”

“…Because dialkylpiperidines, pyrrolidines (1), dialkylpyrrolidines (2), and an indolizine (3) have been found in the poison glands of myrmicine ants, we decided to analyze Aphaenogaster species for similar alkaloids. Here we report that the poison glands of Aphaenogaster fulva and A. tennesseensis (4) contain the tobacco alkaloid anabaseine (Fig.…”

“…Such behavior, rarely observed at the control homogenates, might be interpreted as a mild alarm response and suggests that anabaseine is a gustatory repellant when contacted orally or ingested. Nitrogenous compounds released from the venom gland of myrmicine ants have been demonstrated to elicit trailfollowing behavior in Atta (16,17) and Monomorium (2). Anabaseine, tested according to the method of Moser and Blum (18), elicited no such behavior in A. fulva.…”

Control of the regiospecific synthesis of dialkylpyrrolizidinones and their stereochemical behaviour using gas chromatography/mass spectrometry with chemical ionization

“…[SJH' is more stabilized under ammonia CI than is [6]H+, in which an intramolecular hydrogen bond is absent (Fig. 6) Table 3.…”

(± )-3 ,4 -Dihydro-5-methyl-4-n-alkyl-und -alkenyl-2H-pyrrole aus Pseudomonas putida [1] / (± )-3,4-Dihydro-5-methyl-4-n-alkyl and -alkenyl-2H-pyrroles from Pseudomonas putida [1]

“…als Z w ischenstufe der biologischen P ro lin-S ynthese (l-P y rro lin -5 -carb o n säu re) [8], als A l kaloid des T ab a k ra u ch s (M yosm in) [9], als m ikro bielle M e tab o liten (P ro ferro ro sam in A [10], Siderochelin A [11], D esdanin [12], Polyzonim in [13]), als S tru k tu re lem en t des C orrin -G erü stes [14], o der als B estan d teil des G iftes verschiedener F eueram eisen (2 ,5 -D ialk y l-l-p y rro lin -D eriv ate) [15], in dem auch das den von uns isolierten D ihydropyrrol-D erivaten stru k tu rell beso n d ers n ahe verw andte 2-M ethyl-3-hexadecyl-pyrrolidin en th alten sein sollte, was aber aufgrund ein er (nicht ganz eindeutigen) Synthese n u n m e h r zw eifelhaft erscheint [16]. 3,4-D ihydro-5-m ethyl-4-tt-tridecyl-2 //-p y rro l ( l a ) und seine B eg leitv erbindungen l b -l d sind unseres W issens bislang w ed er als N atu rsto ffe noch als S ynthesepro d u k te b eschrieben w orden.…”