Article (Scientific journals)
Biosynthetic studies on adaline and adalinine, two alkaloids from ladybird beetles (Coleoptera : Coccinellidae)
Laurent, Pascal; Lebrun, Benjamine; Braekman, Jean-Claude et al.
2001In Tetrahedron, 57 (16), p. 3403-3412
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Keywords :
alkaloids; biogenesis; retro-Mannich; insects; labelling; electro-chemistry
Abstract :
[en] The biosynthesis of the homotropane alkaloid (-)-adaline in the coccinellid beetle Adalia bipunctata has been studied by incorporation experiments with [1-C-14] and [2-C-14]acetate. A degradation scheme was developed which selectively afforded benzoic acid containing the carbonyl carbon atom of adaline. The labelling pattern thus obtained indicated that the alkaloid is biosynthesized via a polyacetate pathway. Moreover, feeding A. bipunctata adults with (-)-[10,10,11,11,12,12,13,13,14,14,14-H-2(11)]adaline . HCl afforded (-)-[7,7,8,8,9,9,10,10,11,11,11-H-2(11)]adalinine, demonstrating a biogenetic relationship between the two alkaloids. possible mechanisms for this conversion are discussed. Finally, the synthetic scheme devised to obtain (+/-)-6-acetonyl-2-pentyl-1-piperideine did not yield the target compound, but afforded instead (+/-)-adaline in moderate yields. This unexpected result gives support to the hypothesis that this piperideine could be a key intermediate in the biosynthesis of adaline.
Disciplines :
Chemistry
Author, co-author :
Laurent, Pascal ;  Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Lebrun, Benjamine
Braekman, Jean-Claude
Daloze, Désiré
Pasteels, Jacques
Language :
English
Title :
Biosynthetic studies on adaline and adalinine, two alkaloids from ladybird beetles (Coleoptera : Coccinellidae)
Publication date :
2001
Journal title :
Tetrahedron
ISSN :
0040-4020
Publisher :
Pergamon Press, Oxford, United Kingdom
Volume :
57
Issue :
16
Pages :
3403-3412
Peer reviewed :
Peer Reviewed verified by ORBi
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