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

Abstract

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.