New terpenoids from the fermentation broth of the edible mushroom .

The strophariaceous basidiomycete (synonyms and ) is one of the most praised cultivated edible mushrooms and is being cultivated at large scale for food production. Furthermore, the fungus serves as a model organism to study fruiting body formation and the production of secondary metabolites during the life cycle of Basidiomycota. By studying the secondary metabolite profiles of , we found several terpenoids in submerged cultures. Aside from the main metabolite, bovistol (), two new bovistol derivatives B and C (, ) and pasteurestin C as a new protoilludane () were isolated by preparative HPLC. Their structures were elucidated by mass spectrometry and NMR spectroscopy. The relative configurations of - were assigned by ROESY correlations, and coupling constants in the case of . Applying quantitative PCR for gene expression validation, we linked the production of bovistol and its derivatives to the respective biosynthesis gene clusters.