Anabaseine: Venom Alkaloid of Aphaenogaster Ants

Abstract

Anabaseine, a tobacco alkaloid, is identified as a poison gland product in Aphaenogaster ants, in which it functions as an attractant.

Trail-following behaviour in two Aphaenogaster ants

“…Anabasine and anabaseine have been found in some Aphaenogaster species and in the close genus Messor (Coll et al 1987;Brand and Mpura 1993;Jackson et al 1989;Leclercq et al 2001;Cruz-Lopez et al 2004); however, these alkaloids are sometimes absent, which can be of taxonomic significance [see reviews by Braekman et al (1998); Morgan (2008Morgan ( ), (2009. They are present in all Aphaenogaster species sensu stricto where they have been sought, such as A. rudis (Attygalle et al 1998), A. fulva and A. tennesseensis (Wheeler et al 1981), A. subterranea and A. miamiana (Leclercq et al 2001). The disparity in alkaloid production between the two closely related species, A. senilis and A. iberica, raises an evolutionary question as to the selective pressures that may have induced strong chemical differences in the poison gland chemistry, but not in that of Dufour's gland.…”

Marine Pharmacology: Potentialities in the Treatment of Infectious Diseases, Osteoporosis and Alzheimer's Disease

“…Especially, low nicotine affinity α7 subtype receptors have become a new target for β-amyloid mediated neurotoxicity studies, in order to find α7 receptors agonists that could stem the ravages of AD [120]. In this context, anabaseine 84 (a paralyzing toxin isolated from the nemertine worm Amphiporus lactifloreus [121] and also found in ants [122]), which is structurally related to nicotine, was elicited for its agonist nicotinic receptor activity, providing a good model for searching potential candidates. Starting from the anabaseine structure, numerous analogues were synthesised, which led to the discovery of 3-(2,4-dimethoxybenzylidene)-anabaseine, also called GTS-21 or DMXBA 85 (Fig.…”

Complete assignments 1H and 13C NMR spectral data of four anabaseine derivatives

“…The organic layer was dried with Na 2 SO 4 and the solvent evaporated to give the amide A, which was cyclized by a Bischler-Napieralski reaction to give 2 (4.74 g, 75% yield from amide). IR (KBr, , cm 1 ): 1636 (C N).…”

“…1) was initially isolated from a marine worm, but has subsequently been found in certain species of ants. 3,4 As with nicotine, anabaseine enhances passive avoidance behavior in nucleus basalis-lesioned rats 5 and has been extensively studied for its potential activity on nicotinic acetylcholine receptors (nAChR). 6 In this paper, we describe the structure determination, conducted entirely by the use of NMR spectroscopy, and the complete chemical shift assignments of the 1 H and 13 C NMR spectra of four anabaseine derivatives afforded from 6,7-dimethoxy-1-(pyridin-3-yl)-3,4-dihydroisoquinoline (2) 7 as potential nicotinic agonists.…”