Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata byAspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phasesemipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleavedproduct, and perrottetin F 6’-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. Theantimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxicproperties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) andhuman lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties incomparison to the starting compound - perrottetin F. The antimicrobial properties of these compounds were alsoevaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureusdetermined between 100 µM and 450 µM. The metabolites showed remarkable ability to inhibit synthesis ofbacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore,biotransformation method represents fast and effective tool for obtaining new bioactive structures.