Two novel chlorinated sorbicillinoids named chloctanspirones A ( 1) and B ( 2), possessing an unprecedented bicyclo[2.2.2]octane-2-spiro cyclohexane skeleton, together with their quasi-precursors terrestrols K ( 3) and L ( 4), two additional new chlorinated compounds, were isolated from a marine sediment derived fungus Penicillium terrestre. Their structures including absolute stereochemistries were elucidated by analysis of NMR, MS data, and TDDFT CD calculations. The cytotoxic effects of 1– 4 were preliminarily evaluated in HL-60 and A-549 cells. Compound 1 was active against both HL-60 and A-549 cells with IC 50s 9.2 and 39.7 μM, respectively, while 2 showed weaker activity only against HL-60 cells (IC 50 37.8 μM).