DICRANIN, AN ANTIMICROBIAL AND 15-LIPOXYGENASE INHIBITOR FROM THE MOSS DICRANUM-SCOPARIUM

Extracts of nine mosses, collected in Switzerland, were screened for a ntimicrobial, antioxidative, and 15-lipoxygenase (15-lpo) inhibitory a ctivities. The CH2Cl2 extract of Dicranum scoparium was found to posse ss pronounced antimicrobial activity against Bacillus cereus, Bacillus stearothermophilus, Bacillus subtilis, Staphylococcus aureus, and Esc herichia coli. In addition, inhibition of soybean 15-lpo occurred at v ery low concentration. Phytochemical investigation of this extract aff orded Z,Z,Z-octadeca-6-yne-9,12,15-trienoic acid 1! by a combination of chromatographic techniques. This compound, named dicranin 1!, was found to be responsible for most of the biological activity. The stron gest antimicrobial effect was observed against Streptococcus faecalis (disc diffusion assay). In contrast to the CH2Cl2 extract of D. scopar ium, dicranin was inactive against E. coli. Dicranin was identified by ir, ms, and nmr spectroscopy. A 2D INADEQUATE experiment confirmed th e structure and yielded the assignment of all C-13-nmr signals.