Quinolizidine alkaloids from ants

INDOLIZIDINE AND QUINOLIZIDINE ALKALOIDS FROM AMPHIBIANS AND ANTS... 

Table 1. Mass Spectra of Newly Identified Indolizidine and Quinolizidine Alkaloids from Amphibians And Ants.

The most common indolizidine and quinolizidine alkaloids from amphibians and ants are usually identified by their GC-MS and GC-FTIR spectral characteristics. These spectral features were collected by Garraffo and co-workers [18,19], and can be summarized as follows ... 

Several other general reviews dealing with aspects of indoHzidine and quinolizidine alkaloid chemistry were pubHshed during the period under consideration. The series of annual reports in the Royal Society of Chemistry s journal Natural Product Reports, which provided regular coverage of both simple and various more complex indolizidine and quinolizidine alkaloids, ended in 2008.Another important review that dealt principally with pertinent alkaloids from ants and amphibians, slaframine, polyhydroxy-lated indolizidine alkaloids, and the lupin quinolizidine alkaloids was published in the series Studies in Natural Product Chemistry in 2002, and covered the period 1994 to 1999. ... 

Indolizidine and quinolizidine alkaloids have been found in different natural sources and have been isolated from amphibians, ants, fungi, marine organisms and plants. Most of them have noxious or toxic properties and... 

Indolizidine and quinolizidine alkaloids found in amphibians and ants were studied by Daly and co-workers who classified them in two different classes, A and B, Fig. (1) [2,15-17]. The former include 3,5- and 5,8-disubstituted indolizidines, 5,6,8-trisubstituted indolizidines and 1,4- and 4,6-disubstituted quinolizidines that can be derived from straight-chain carbon precursors. The latter contain one or more isoprene units, and include pumiliotoxins (PTX-A), allopumiliotoxins (a//o-PTX-A or... 

All the currently known indolizidine and quinolizidine alkaloids isolated from ants are illustrated in Fig. 6. (+ )-Monomorine I (427), the well-studied trail pheromone constituent of the Pharaoh ant Monomorium pharaonis), and the analogs 428-431 were described in the earlier volumes in this series. These five compounds are 3,5-disubstituted indolizidines bearing short saturated or mono-unsaturated hydrocarbon chains. The relative stereochemistry in monomorine VI (430) still remains unknown, while that of 431 was atypical for the class at the time of its isolation 380). The structural resemblance of fiiis group of alkaloids to the... 

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