Eight new phenethoxy derivatives, trichoasperellins A-H (<b>1</b>-<b>8</b>), were isolated from the endophytic fungus <i>Trichoderma asperellum</i> G10 isolated from the medicinal plant <i>Areca catechu</i> L. The structures of these compounds were elucidated from spectroscopic data, <i>J</i>-based configurational analysis, and Mosher's methods. Compounds <b>1</b>-<b>4</b> and <b>6</b>-<b>8</b> bear one or two multioxidized C<sub>7</sub> moieties with the same carbon skeleton. The carbon skeletons of compounds <b>6</b>-<b>8</b> are new, all containing three moieties connected via two acetal carbons similar to those of disaccharide glycosides. Compound <b>4</b> inhibited nitric oxide production with an IC<sub>50</sub> value of 48.3 μM, comparable to that of the positive control indomethacin (IC<sub>50</sub>, 42.3 μM).