C-6-9

NEW OLIGOCYCLIC ALKALOIDS FROM ANTS.

Frank Schroeder¹, Wittko Francke¹, Manfred Kaib2,Horst Baumann2
¹Institut für Organische Chemie der Universität,Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
²Lehrstuhl Tierphysiologie der Universität, Postfach101252, 95440 Bayreuth, Germany

Ants of the genus Myrmicaria show an exeptionally large poisongland reservoir, which may contain up to 0.5 ul of a lipo-philic secretion.This secretion is generally made up by a mixture of monoterpene hydrocarbonsand alkaloids. The poison gland secretion of African Myrmicariaants contains three new families of alkaloids, the carbon skeletons ofwhich are made up by one, two or three unbranched C15-chains. The majorconstituents of the lower molecular weight alkaloids are identified aspyrrolo[2,1,5-cd]indolizines while the higher molecular weight componentsshow complex oligocyclic structures. These appear to be closely relatedto the pyrroloindolizines and may be regarded as “oligomers” of the lowmolecular weight alkaloids. Identification of the new alkaloids by NMR-spectroscopyas well as structural relationships are discussed. Biomimetic synthesisshows that these alkaloids could be derived from 2,6-disubstituted piperidineslike 1.

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