Four New Caryophyllene Sesquiterpenoids Isolated From Hypholoma capnoides 819

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.