Indothiazinone, an indolyl thiazolyl ketone from a novel myxobacterium belonging to the Sorangiineae.

ABSTRACT

Indothiazinone (1), an indolyl thiazolyl ketone, was discovered in cultures of novel myxobacterial strain 706, recently isolated from compost in Germany. Molecular phylogenetic studies based on 16S rRNA gene sequences revealed strain 706 to be a representative of a new family of the Sorangiineae. A screening of the culture broth for antimicrobial metabolites followed by isolation and characterization of these compounds revealed six indole derivatives and a 1,4-naphthoquinone derivative. The structures were determined to be indothiazinone (1; 1H-indol-3-yl(1,3-thiazol-2-yl)methanone) and three 3-methylbuta-1,3-dien-1-yl-substituted indoles, indolyl ethanol 2 and the E- and Z-isomers of indolyl ethylidenehydroxylamine 4 and 5 by MS and NMR spectroscopic analyses. In the indolyl ethanol derivative 3 the unsaturated methylene group of the butadienyl residue was replaced by an oxygen atom to give the keto group of the butanone side chain. Further 1H-indol-3-ylacetonitrile (6) was identified, which was already known as a myxobacterial metabolite. 2-Hydroxyethyl-3-methyl-1,4-naphthoquinone (7) was recognized during dereplication as an antibiotic previously isolated from Actinoplanes capillaceus. Whereas 1, 4, 5, and 7 showed weak activity against yeasts and filamentous fungi, isomers 4 and 5 were weakly active against Gram-positive bacteria and mouse fibroblasts. Compound 6 is volatile, and 2 and 3 showed no activity in a number of assays.