Chaetoconvosins A and B (1 and 2), two novel cytochalasan alkaloids with a new 6/6/5/5/7 pentacyclic ring system, were isolated from the solid-state fermented medium of the wheat rhizospheric fungus Chaetomium convolutum cib-100. Their structures were elucidated on the basis of spectroscopic data. The structure of chaetoconvosin A (1) was confirmed by X-ray crystallographic analysis. Chaetoconvosin B (2), the major metabolite, showed remarkable inhibitory ability on root elongation and moderate cytotoxicity against several cancer cell lines. © 2012 American Chemical Society.