The iromycins, a new family of pyridone metabolites from Streptomyces sp. I. Structure, NOS inhibitory activity, and biosynthesis
2007 | journal article. A publication with affiliation to the University of Göttingen.
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The iromycins, a new family of pyridone metabolites from Streptomyces sp. I. Structure, NOS inhibitory activity, and biosynthesis
Surup, F.; Wagner, O.; von Frieling, J.; Schleicher, M.; Oess, S.; Mueller, P. & Grond, S. (2007)
The Journal of Organic Chemistry, 72(14) pp. 5085-5090. DOI: https://doi.org/10.1021/jo0703303
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- Authors
- Surup, Frank; Wagner, Oliver; von Frieling, Jan; Schleicher, Michael; Oess, Stefanie; Mueller, Peter; Grond, Stephanie
- Abstract
- The iromycins A-D are members of a new family of rare alpha-pyridone metabolites. The isolation and structure elucidation of these microbial secondary metabolites from Streptomyces sp. Dra 17 revealed a N-heterocyclic core structure with two unusual side chains. Iromycins act as inhibitors of nitric oxide synthases (NOS), a protein family, which produces the crucial second messenger nitric oxide (NO). Importantly, these compounds inhibit selectively endothelial NOS rather than neuronal NOS and thus set prospects for both medical therapy and basic research. Feeding experiments with C-13- and N-15 -labeled precursors indicated an uncommon type of polyketide biosynthesis and clearly ruled out an isoprenoid origin. A detoxification pathway of a particular secondary metabolite in the host strain is a rare observation and here we demonstrate it with the iromycin family.
- Issue Date
- 2007
- Status
- published
- Publisher
- Amer Chemical Soc
- Journal
- The Journal of Organic Chemistry
- ISSN
- 0022-3263