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

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 IC₅₀ 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.