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Five new  α -pyrones, xylariaopyrones E–I ( 1 – 5 ), along with three known analogues ( 6 – 8 ) were isolated from the cultivation broth of the endophytic fungus  Xylariales  sp. (HM-1). The structures of the new compounds including their absolute configurations were elucidated by comprehensive spectroscopic methods and quantum ECD calculations. Xylariaopyrone E ( 1 ) is the first example of  α -pyrone derivative with a novel [3, 2, 0] bridge ring system  via  a ketal function group in the side chain. In bioactivity assays, xylariaopyrones E–G ( 1 – 3 ) showed moderate inhibiting activities against  Escherichia coli ,  Staphylococcus aureus  and  Pseudomonas aeruginosa  with MIC values from 25.4 to 64.5 μg/mL, whereras xylariaopyrone G ( 3 ) exhibited significant inhibition of monoamine oxidase B with an IC 50  value of 15.6 μmol/L. Xylariaopyrone H ( 4 ) and the known compound  7  showed moderate toxicity against brine shrimp larvae with inhibition rates of 42.8% and 44.5%, respectively.

Xylariaopyrones E–I, five new α-pyrone derivatives from the endophytic fungus Xylariales sp. (HM-1)