Parallel Chromatography in Natural Products Chemistry: Isolation of New Secondary Metabolites from Streptomyces sp

Integration of parallel chromatography on both, gel permeation and silica gel chromatography by making use of the CombiFlashTM si1000s system (ISCO, Lincoln, USA) into purification process to speed up the isolation of secodary metabolites from microorganisms. As an example, we applied this approach to Streptomyces sp. (GT 061089) which led to the isolation and structural characterization of six 2-3-disubstituted butanoids (1 to 6), four 2,4-disubtituted butanoids (7 to 10), a monoterpenoid (11), two indol compounds (12, 13), a furan-3-carboxylic acid (14), as well as two already known isocoumarins (15, 16). The isolated pure compounds were characterized by spectroscopic methods and chemical transformations. The results of biological tests showed that both 15 and 16 possess medium cytotoxic activity and strong inhibiting activity on horse radish peroxidase. 15 also exhibits antiviral activity as well as a distinct inhibiting activity on 3a-hydroxysteroid dehydrogenase (3a-HSD).