Four previously undescribed caryophyllene sesquiterpenoids ( 1 – 4 ) along with one known drimane sesquiterpenoid ( 5 ) were isolated from the fermentation products of the mushroom Hypholoma capnoides 819. The structures of 1–4 with rare tricyclic skeleton (6/5/4) or bicyclic skeletons (9/4) were determined on the basis of comprehensive spectroscopic data analysis, calculated NMR, ORD data, and their biosynthetic pathways. Compounds 1–5 only showed very weak cytotoxicity toward mouse microglial cells (BV2), breast cancer cells (MCF-7), and human lung cancer cells (A549) at 40 µM. In addition, none of the compounds demonstrated antibacterial activity against Staphylococcus aureus or Escherichia coli at 128 µg/mL. Graphical Four previously undescribed caryophyllene sesquiterpenoids (1–4) along with one known drimane sesquiterpenoid (5) were isolated from the fermentation products of the mushroom Hypholoma capnoides 819.
Nine previously undescribed sesquiterpenoids , named as capnoidones A–G ( 1 – 6 and 8 ) and capnoidols A and B ( 7 and 9 ), along with three known sesquiterpenoids , fascicularones A, B, and G ( 12 , 11 and 10 ), were isolated from the fermentation products of the mushroom Hypholoma capnoides 819 (Strophariace). The structures of these compounds were determined through MS and NMR experiments along with electronic circular dichroism analysis. Optical rotation calculations and X-ray diffraction experiments were also conducted for confirmation of the structures. Compounds 1 and 4 displayed mild cytotoxicity towards BV2 microglial cells in mice , while compound 4 exhibited mild cytotoxicity against breast cancer MCF-7 cells. However, none of the compounds demonstrated antibacterial activity against Staphylococcus aureus or Escherichia coli .