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

Autor(es): Pesek, Jelena; Svoboda, Jiri; Sattler, Martina; Bartram, Stefan; Boland, Wilhelm


Resumo: 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.


Palavras-Chave: Major Branch Pathway; Xanthurenic acid; Drosophila melanogaster; 6-Hydroxykynurenic acid; Aedes aegypti; 3-Hydroxykynurenine; Mosquito; Streptomyces; Noctuidae; Oxidation


Imprenta: Organic & Biomolecular Chemistry, v. 13, n. 1, p. 178-184, 2015


Identificador do Objeto Digital: 10.1039/c4ob01857e


Descritores: Aedes aegypti - Biosynthesis


Data de Publicação: 2015