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

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Pesek,  Jelena
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Svoboda,  Jiri
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Sattler,  Martina
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Bartram,  Stefan
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Boland,  Wilhelm
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Citation

Pesek, J., Svoboda, J., Sattler, M., Bartram, S., & Boland, W. (2014). Biosynthesis of 8-hydroxyquinoline-2-carboxylic acid, an iron chelator from the gut of the lepidopteran Spodoptera littoralis. Organic & Biomolecular Chemistry, 13(1), 178-184. doi:10.1039/c4ob01857e.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0023-EC17-8
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.