Six new nonadride derivatives, named talarodrides A-F (<b>1</b>-<b>6</b>), were isolated from the Antarctic sponge-derived fungus <i>Talaromyces</i> sp. HDN1820200. All structures including the absolute configurations were deduced by extensive spectroscopic analysis and computational ECD calculations. Compounds <b>1</b>-<b>4</b> share a rare caged bicyclo[4.3.1]-deca-1,6-diene with a bridgehead olefin and maleic anhydride core skeleton, while compounds <b>5</b> and <b>6</b> possess the first case of a naturally occurring 5/7/6 methanocyclonona[<i>c</i>]furan skeleton. Talarodride A (<b>1</b>) and talarodride B (<b>2</b>) showed selective inhibitory effects against <i>Proteus mirabilis</i> and <i>Vibrio parahemolyticus</i> with MICs of 3.13-12.5 μM.