Figure 3.

Ribosylated stilbenes occur in two Basidiomycota species of spruce tree- and bark beetle–associated fungi. (a–c) Confirmed structures of ribosylated derivatives of piceatannol (a), isorhapontigenin (b), and resveratrol (c). Depicted are extracted ion chromatograms and mass spectra from untargeted UHPLC–qTOF–MS analyses performed in negative ionization mode for glucosides and their derivatives. Compounds are from the incubation of C. radians with the corresponding stilbene glucosides. NMR spectra and assignments are shown in Supplementary Fig. S2 and Table S4. (d–f) Screening of a range of other fungal species by UHPLC–qTOF–MS for piceid metabolites. Fungi are spruce tree associates (d), I. typographus symbionts (e), or represent three additional Basidiomycota strains (f). Extracted ion chromatograms obtained in the negative ionization mode. Fungal species belonging to Ascomycota are shown in black, and Basidiomycota in orange. Representative mass spectra of phenolic standards are shown in Supplementary File 2. (g) Phylogenetic analysis of fungal isolates. ITS region sequences were aligned using MUSCLE, and a UPGMA tree was generated in Geneious prime. Branch labels indicate consensus support (%), and ITS rRNA gene sequences are provided in Supplementary File 1.