Characterization of polyketide metabolites from foliar endophytes of Picea glauca

A collection of 250 foliar endophytes of Picea glauca (white spruce) yielded several isolates that produced metabolites toxic to Choristoneura fumiferana (spruce budworm). Three of these strains were selected for further study based on their ability to be cultured and produce secondary metabolites under laboratory conditions. The culture filtrate of each was extracted and analyzed by LC-MS and LC-NMR, and the major metabolites were isolated and characterized. Structures were elucidated by spectroscopic analyses including 2D NMR and HRMS and by comparison to literature data. In some cases the extract was methylated in order to facilitate separation, but the original natural structure was determined by comparing the NMR data of the isolated methylated product with that of the stop-flow NMR of the underivatized extract (i.e., 2a, 2b, and 4). Two of these metabolites, 1 and 2a, are new structures, 3 and 4 are reported here for the first time as fungal metabolites, and 5-10 as known fungal metabolites from other species. Tyrosol (10) was the only common metabolite found in all three extracts but did not account for the observed toxicity to C. fumiferana. © 2008 American Chemical Society and American Society of Pharmacognosy.