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•Pleosporalesones A–B (1–2), two unique polyketides isolated from fungi.•A new class of polyketides bearing an unusual 6/6/7/6 tetracyclic ring system.•A plausible biosynthetic pathway for pleosporalesones A–B (1–2) was proposed.
Two unique polyketides, pleosporalesones A–B (1–2), bearing an unusual 6/6/7/6 tetracyclic ring system consisting of a chromone ring and a benzoannulated cycloheptanone ring, were isolated from the solid cultures of Pleosporales sp.. The chemical structures were elucidated by analyses of their extensive spectroscopic data, including 1D/2D NMR, ORD, CD and HR-ESI-MS, and the absolute configurations were established by comparison of their experimental circular dichroism data with those calculated. A plausible biosynthetic pathway for pleosporalesones A–B was proposed.