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- Title
Induced Production, Synthesis, and Immunomodulatory Action of Clostrisulfone, a Diarylsulfone from Clostridium acetobutylicum.
- Authors
Neuwirth, Toni; Letzel, Anne‐Catrin; Tank, Cedric; Ishida, Keishi; Cyrulies, Michael; Schmölz, Lisa; Lorkowski, Stefan; Hertweck, Christian
- Abstract
The anaerobe Clostridium acetobutylicum belongs to the most important industrially used bacteria. Whereas genome mining points to a high potential for secondary metabolism in C. acetobutylicum, the functions of most biosynthetic gene clusters are cryptic. We report that the addition of supra‐physiological concentrations of cysteine triggered the formation of a novel natural product, clostrisulfone (1). Its structure was fully elucidated by NMR, MS and the chemical synthesis of a reference compound. Clostrisulfone is the first reported natural product with a diphenylsulfone scaffold. A biomimetic synthesis suggests that pentamethylchromanol‐derived radicals capture sulfur dioxide to form 1. In a cell‐based assay using murine macrophages a biphasic and dose‐dependent regulation of the LPS‐induced release of nitric oxide was observed in the presence of 1.
- Subjects
CLOSTRIDIUM acetobutylicum; BIOMIMETIC synthesis; SECONDARY metabolism; NATURAL products; CHEMICAL synthesis; SULFUR dioxide; GENE clusters
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 68, p15855
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202003500