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Cocultivation of the high cytochalasan-producing fungi Aspergillus flavipes and Chaetomium globosum resulted in the isolation of 11 undescribed Chae -type cytochalasans. Their structures were determined by spectroscopic data and NMR data calculations. Asperchaetoglobin A (1) was the first Chae -type cytochalasan possessing an unprecedented nitrogen bridge between C-17 and C-20 to generate a surprising 5/6/12/5 multiple ring system; asperchaetoglobins B and C (2 and 3) displayed higher oxidation with an additional epoxide at the thirteen-member ring; asperchaetoglobin D (4) was the second Chae -type cytochalasin featuring a 5/6/12 tricyclic ring system. The cytotoxic activities against five human cancer cell lines and antibacterial activities against Staphylococcus aureus and Colon bacillus of selected compounds were evaluated in vitro. 11 undescribed Chae -type cytochalasans were isolated from coculture of Aspergillus flavipes and Chaetomium globosum. [Display omitted] • This is the first report of coculture of Aspergillus flavipes and Chaetomium globosum in liquid medium. • Eleven undescribed Chae -type cytochalasans asperchaetoglobins A-K were isolated and characterized. • Asperchaetoglobin A (1) possessing an unprecedented nitrogen bridge between C-17 and C-20. • The cytotoxic and antibacterial activities were evaluated in vitro. [ABSTRACT FROM AUTHOR]