Issue 1, 2015

Biosynthesis of 8-hydroxyquinoline-2-carboxylic acid, an iron chelator from the gut of the lepidopteran Spodoptera littoralis

Abstract

In the regurgitate (foregut content) of Spodoptera larvae we found high concentrations (0.5–5 mM) of 8-hydroxyquinoline-2-carboxylic acid (8-HQA). In a survey of different lepidopteran species, this compound was only detected in species belonging to the family of Noctuidae. 8-HQA was shown to derive from tryptophan metabolism. The amount of 8-HQA in the regurgitate was strongly dependent on the tryptophan content of the diet. In the insect 8-HQA is generated from tryptophan via kynurenine and 3-hydroxykynurenine. 8-HQA is produced by the larvae and not by their commensal gut bacteria. Analysis of different life stages of Spodoptera larvae revealed that 8-HQA is formed during the larval stage, probably acting as an iron chelator to control the gut microbiome.

Graphical abstract: Biosynthesis of 8-hydroxyquinoline-2-carboxylic acid, an iron chelator from the gut of the lepidopteran Spodoptera littoralis

Supplementary files

Article information

Article type
Paper
Submitted
30 Aug 2014
Accepted
08 Oct 2014
First published
09 Oct 2014

Org. Biomol. Chem., 2015,13, 178-184

Author version available

Biosynthesis of 8-hydroxyquinoline-2-carboxylic acid, an iron chelator from the gut of the lepidopteran Spodoptera littoralis

J. Pesek, J. Svoboda, M. Sattler, S. Bartram and W. Boland, Org. Biomol. Chem., 2015, 13, 178 DOI: 10.1039/C4OB01857E

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