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

Org Biomol Chem. 2015 Jan 7;13(1):178-84. doi: 10.1039/c4ob01857e.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / metabolism
  • Hydroxyquinolines / metabolism*
  • Intestinal Mucosa / metabolism*
  • Intestines / microbiology
  • Iron Chelating Agents / metabolism*
  • Kynurenine / analogs & derivatives
  • Kynurenine / metabolism
  • Larva / metabolism
  • Spodoptera / metabolism*
  • Spodoptera / microbiology
  • Tryptophan / metabolism

Substances

  • 8-hydroxyquinolinecarboxylic acid
  • Anti-Bacterial Agents
  • Hydroxyquinolines
  • Iron Chelating Agents
  • 3-hydroxykynurenine
  • Kynurenine
  • Tryptophan