From the stems of Fissistigma bracteolatum, a novel natural product with an unprecedented skeleton, bractelactone (1), was isolated, together with four known compounds: piperolactam A (2), aristololactam BIII (3), aristololactam BII (4), and fissilandione (5). The structure of 1 was established on the basis of spectroscopic data as (3Z)‐6,7‐dihydroxy‐4‐methoxy‐3‐(phenylmethylidene)‐5‐(3‐phenylpropanoyl)‐1‐benzofuran‐2(3H)‐one. This compound may be derived from a hybrid of a chalcone and a cinnamic acid, or from a degradation product of a dichalcone. Compounds 1, 2, and 5 showed inhibitory effects on NO generation by RAW264.7 macrophages in response to lipopolysaccharide. Compounds 2 and 5 showed inhibitory effects on formyl‐L‐methionyl‐L‐leucyl‐L‐phenylalanine (fMLP)‐induced superoxide anion (O$\rm{_{2}^{{^\cdot} -}}$) generation in human neutrophils.