| Summary: | <i>Penicillum citreonigrum</i> XT20-134 (MCCC 3A00956) is a fungus with cytotoxic activity, derived from deep-sea sediment. Five new compounds, adeninylpyrenocine (<b>1</b>), 2-hydroxyl-3-pyrenocine-thio propanoic acid (<b>2</b>), ozazino-<i>cyclo</i>-(2,3-dihydroxyl-trp-tyr) (<b>3</b>), 5,5-dichloro-1-(3,5-dimethoxyphenyl)-1,4-dihydroxypentan-2-one (<b>4</b>), and 2,3,4-trihydroxybutyl cinnamate (<b>5</b>), together with 19 known compounds (<b>6</b>−<b>24</b>), were isolated from an ethyl acetate (EtOAc) extract of its fermentation. The structures of the new compounds were comprehensively characterized by high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR). All isolates were evaluated for their cytotoxic activities. The heteroatom-containing new compounds <b>2</b> and <b>4</b> showed potent cytotoxicity to the human hepatoma tumor cell Bel7402 with IC<sub>50</sub> values of 7.63 ± 1.46, 13.14 ± 1.41 μM and the human fibrosarcoma tumor cell HT1080 with IC<sub>50</sub> values of 10.22 ± 1.32, 16.53 ± 1.67 μM, respectively.
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