From ants

CScheme 10.13. New ilkdloicls from ants, CiR, 55, Q/fi-S-biityl-S-d-oxopropyliindolmcline and CiR, 5R, Q/fi-S-biityl-S-Cl-oxopropyliindolmdine, are identified and synthesized as outlined in Scheme 10.14. ... 

Venoms causing anaphylaxis or other allergic reactions originate almost exclusively from social Hymenoptera, most often honeybees and vespids (fig. 1) [1], occasionally from bumble bees [2], in America [3] and in Australia [4], also from ants. Stings by other insects like mosquitoes, bedbugs, fleas, horse flies and midges can very rarely also cause systemic allergic reactions. These are however not due to venoms but to... 

These IHs have been applied to the synthesis of several pyrroHnes and 2,3,4,5-tetrahydropyridines known as venom constituents from ant species [278]. 

Scheme 10.13).110 New alkaloids from ants, (3R, 5.S, 9fl)-3-butyl-5-(l-oxopropyl)indolizidine and (3R, 5R, 9/ )-3-butyl-5-(l-oxopropyl)indolizidine, are identified and synthesized as outlined in Scheme 10.14.111... 

An example of an uncharacterized chemical cue from ant brood occurs in the obligatory slave-making ant, Polyergus breviceps. Pupae of this species are cared for by their enslaved host worker, while pupae of other species are consumed [125]. 

An example from ants is the acceptance of the caterpillar of the parasitic butterfly Maculinea rebeli by its host Myrmica schencki [132]. The caterpillar chemically mimics ant larvae and, in its final instar, drops from its food plant and waits for a foraging ant worker to bring it to the brood chambers of the host colony [133]. 

The number of natural products containing these tricyclic systems is relatively small, viz. a few alkaloids from marine (compound 293), fungal (compound 282), amphibian (compound 395), insect (compound 387), and plant sources (compound 288) and also some iridoid molecules (compounds 98-100). Some of those Myrmkaria alkaloids (from ants Section 12.16.6.5.2) which contain the 5 5 6 fused-ring system are perhaps the most extensively studied of these natural products, with several successful syntheses now recorded. 

Alkaloids from ants have been comprehensively reviewed in 1987 by Numata and Ibuka [115], in 1990 by Braekman and Daloze [116] and more recently by Leclercq et al. [114]. We will thus report only the literature that has been published since and until October 2003. 

Although many insect defensive compounds are endowed with diverse biological activities, few of them have been studied in depth to evaluate their potential pharmacological activities. Cantharidin (98) (Fig. 16),pederin (104) (Fig. 18), and some of the alkaloids isolated from ants (e.g., the solenopsins 109 and 110, Fig. 19) have been the subject of most of the investigations. These topics have been reviewed several times [111, 214,215], and we will only summarize here the most recent data. 

Numata A,Ibuka T (1987) Alkaloids from ants and other insects. In Brossi A (ed) The alkaloids, vol 31. Academic Press, New York, p 193... 

It was first isolated from ants and takes its name from the Latin word for ant, formic a. An ant bite injects a small amount of formic acid into the victim, accounting for the... 

Tables I through VIII summarize the occurrences of alkaloids from ants and other insects. Each table presents chemical structures as well as specific sources of particular types of alkaloids e.g.. Table I covers piperidines and pyridines. Table II, pyrrolidines, pyrroles, and indolizidines.

The structure of anabaseine (8), isolated from ants of Aphaenogaster species (Table I), was established by gas chromatography-mass spectrometry, the H-... 

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