A new family of tricyclic alkaloids from Myrmicaria ants

The poison gland secretion of the African ant, Myrmicaria opaciventris, contains three families of new alkaloids. These alkaloids are represented by a “monomeric” type with 15 carbon atoms in a row forming derivatives of indolizines, while the two other families are “dimers” and “trimers” with 30 an...

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Bibliographic Details
Published inTetrahedron Vol. 52; no. 43; pp. 13539 - 13546
Main Authors Schröder, Frank, Franke, Stephan, Francke, Wittko, Baumann, Horst, Kaib, Manfred, Pasteels, Jacques M, Daloze, Désiré
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.10.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EUMENOIDES
POISON GLAND SECRETION
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Summary:The poison gland secretion of the African ant, Myrmicaria opaciventris, contains three families of new alkaloids. These alkaloids are represented by a “monomeric” type with 15 carbon atoms in a row forming derivatives of indolizines, while the two other families are “dimers” and “trimers” with 30 and 45 carbon atoms, respectively. The major constituents of the low molecular weight alkaloids are identified to be pyrrolo[2,1,5-cd]indolizines, highly dominated by l-ethyl-3,4,41,5,6,7-hexahydro-2-((1 Z)-1-propenyl)-pyrrolo[2,1,5-cd]indolizine, myrmicarin 215A. The higher molecular weight components show complex oligocyclic structures, which are closely related to the pyrroloindolizines. The alkaloid pattern shows a high degree of intraspecific variation. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00834-4