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Five new indole diterpenoids named paspaline C–D (<b>1</b>–<b>2</b>) and paxilline B–D (<b>3</b>–<b>5</b>), as well as eleven known analogues (<b>6</b>–<b>16</b>), were identified from fungus <i>Penicillium brefeldianum</i> strain WZW-F-69, which was isolated from an abalone aquaculture base in Fujian province, China. Their structures were elucidated mainly through 1D- and 2D-NMR spectra analysis and ECD comparison. Compound <b>1</b> has a 6/5/5/6/6/8 hexacyclic ring system bearing 2,2-dimethyl-1,3-dioxocane, which is rare in natural products. Compound <b>2</b> has an unusual open F-ring structure. The cytotoxic activities against 10 cancer cell lines and antimicrobial activities against model bacteria and fungi of all compounds were assayed. No compound showed antimicrobial activity, but at a concentration of 1 μM, compounds <b>1</b> and <b>6</b> exhibited the highest inhibition rates of 71.2% and 83.4% against JeKo-1 cells and U2OS cells, respectively.