Four new vermistatin derivatives, dihydrovermistatin (1), acetoxydihydrovermistatin (2), hydroxydihydrovermistatin (3), and penisimplicissin (4) were isolated along with vermistatin (5), penicillide, and funicone from the extract of Penicillium simplicissimum IFM 53375.The structures of 1 -4 were determined by spectroscopic and chemical methods.