Four new guanacastane-type diterpenoids (1–4), named plicatilisins E-H, together with the known compound, plicatilisin D (5), were isloated from two fermentation extracts (i.e., solid state fermentation on PDA medium & static fermentation of malt extract broth culture medium) of the fungal strain Coprinus plicatilis 82. Their structures were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D NMR as well as FT-ICR-MS, UV, and IR, and comparison with literature data. All the compounds showed insignificant cytotoxicities against the cancer cell line HCT116.