Document Detail

Insect-synthesised retronecine ester alkaloids: precursors of the common arctiine (Lepidoptera) pheromone hydroxydanaidal.
MedLine Citation:
PMID:  18030534     Owner:  NLM     Status:  MEDLINE    
Many pyrrolizidine alkaloid (PA)-adapted insects convert PAs sequestered from their larval host plants into "insect-PAs" in which the acid components of the alkaloids are replaced by small, branched aliphatic 2-hydroxy acids of insect origin. It has been proposed that insect-PAs are precursors of the pheromone hydroxydanaidal in male Estigmene acrea moths, but it is not clear why they are specifically required or what the structural features or chemical properties are that make insect-PAs more suitable for conversion into hydroxydanaidal than superficially similar alkaloids of plant origin. Evidence is presented that insect-PAs are also precursors of hydroxydanaidal in the polyphageous arctiine, Creatonotos transiens, and a new biosynthetic pathway to hydroxydanaidal is proposed that has a mandatory requirement for insect-PAs as intermediates.
John A Edgar; Michael Boppré; Eva Kaufmann
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Publication Detail:
Type:  Journal Article     Date:  2007-11-21
Journal Detail:
Title:  Journal of chemical ecology     Volume:  33     ISSN:  0098-0331     ISO Abbreviation:  J. Chem. Ecol.     Publication Date:  2007 Dec 
Date Detail:
Created Date:  2007-12-06     Completed Date:  2008-04-02     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7505563     Medline TA:  J Chem Ecol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  2266-80     Citation Subset:  IM    
CSIRO Livestock Industries, Private Bag 24, Geelong, Victoria, 3220, Australia.
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MeSH Terms
Alkaloids / biosynthesis*
Chromatography, Liquid
Chromatography, Thin Layer
Gas Chromatography-Mass Spectrometry
Lepidoptera / metabolism*
Pheromones / chemistry*
Pyrrolizidine Alkaloids / metabolism*
Reg. No./Substance:
0/Alkaloids; 0/Pheromones; 0/Pyrrolizidine Alkaloids; 34199-35-4/hydroxydanaidal; 480-85-3/retronecine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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