Induced Production, Synthesis, and Immunomodulatory Action of Clostrisulfone, a Diarylsulfone from Clostridium acetobutylicum.
Chemistry
; 26(68): 15855-15858, 2020 Dec 04.
Article
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| MEDLINE
| ID: mdl-32996646
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.
Palabras clave
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Sulfonas
/
Clostridium acetobutylicum
/
Factores Inmunológicos
Límite:
Animals
Idioma:
En
Año:
2020
Tipo del documento:
Article