title: 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.
authors.affiliation: Department of Bioorganic Chemistry, Max-Planck-Institute for Chemical Ecology, Hans-Knöll-Straße 8, 07745 Jena, Germany. boland@ice.mpg.de.
authors.forename: Jelena
authors.initials: J
authors.lastname: Pesek
authors.forename: Jiří
authors.initials: J
authors.lastname: Svoboda
authors.forename: Martina
authors.initials: M
authors.lastname: Sattler
authors.forename: Stefan
authors.initials: S
authors.lastname: Bartram
authors.forename: Wilhelm
authors.initials: W
authors.lastname: Boland
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000378:metabolism; D006912:Hydroxyquinolines / Q000378:metabolism*; D007413:Intestinal Mucosa / Q000378:metabolism*; D007422:Intestines / Q000382:microbiology; D007502:Iron Chelating Agents / Q000378:metabolism*; D007737:Kynurenine / Q000031:analogs & derivatives / Q000378:metabolism; D007814:Larva / Q000378:metabolism; D018411:Spodoptera / Q000378:metabolism* / Q000382:microbiology; D014364:Tryptophan / Q000378:metabolism
chemical_list: C587018:8-hydroxyquinolinecarboxylic acid; D000900:Anti-Bacterial Agents; D006912:Hydroxyquinolines; D007502:Iron Chelating Agents; C005045:3-hydroxykynurenine; D007737:Kynurenine; D014364:Tryptophan