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Fourteen new eremophilane-type sesquiterpenoids, named rhizoperemophilanes A~N ( 1 ~ 14 ), together with eight known congeners, were isolated from the culture of the endophytic fungus  Rhizopycnis vagum . The structures of the new compounds were elucidated by extensive spectroscopic analyses, as well as ECD calculations and the modified Mosher's method for the assignment of the absolute configurations. Rhizoperemophilane J ( 10 ) contains an uncommon C-4/C-11 epoxy ring, while rhizoperemophilane N ( 14 ) features an unprecedented 3-nor-eremophilane lactone-lactam skeleton. These metabolites were evaluated for their antibacterial, cytotoxic, and phytotoxic activities. Among them, compounds  11 ,  16 , and  20  displayed antibacterial activities, while  14  showed selective cytotoxicity against NCI-H1650 and BGC823 tumor cells. Moreover, compounds  5 ,  6 ,  12 ,  13 ,  16 , and  19  exhibited strong phytotoxic activities against the radicle elongation of rice seedlings.

Eremophilane-Type Sesquiterpenoids From the Endophytic Fungus Rhizopycnis vagum and Their Antibacterial, Cytotoxic, and Phytotoxic Activities