Dimeric azaphilones from the xylariaceous ascomycete Hypoxylon rutilum

Fractionation of the methanolic extract of the stromata of Hypoxylon rutilum (Xylariaceae, Ascomycetes) resulted in the isolation of two novel dimeric azaphilones named rutilins A and B, together with the known compounds, entonaemin A, and rubiginosins A and B. Their structures were elucidated by 2D NMR, HR-MS, IR and UV spectroscopy. Rutilins A and B are presumably synthesized via specific biogenic aldol condensations of mitorubrinol acetate moieties with rubiginosins A and B, respectively. The resulting dimeric azaphilone scaffold of the rutilins is unprecedented in nature.