| Summary: | The new asperorlactone (<b>1</b>), along with the known illudalane sesquiterpene echinolactone D (<b>2</b>), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2<i>H</i>-pyran-2-one (<b>3</b>) and its acetate <b>4</b>, and 4-hydroxybenzaldehyde (<b>5</b>), were isolated from a culture of <i>Aspergillus oryzae</i>, collected from Red Sea marine sediments. The structure of asperorlactone (<b>1</b>) was elucidated by HR-ESIMS, 1D, and 2D NMR, and a comparison between experimental and DFT calculated electronic circular dichroism (ECD) spectra. This is the first report of illudalane sesquiterpenoids from <i>Aspergillus</i> fungi and, more in general, from ascomycetes. Asperorlactone (<b>1</b>) exhibited antiproliferative activity against human lung, liver, and breast carcinoma cell lines, with IC<sub>50</sub> values < 100 µM. All the isolated compounds were also evaluated for their toxicity using the zebrafish embryo model.
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