| Summary: | On the basis of the ‘one strain, many compounds’ (OSMAC) strategy, chemical investigation of the marine-derived fungus <i>Trichothecium roseum</i> resulted in the isolation of trichomide cyclodepsipeptides (compounds 1⁻4) from PDB medium, and destruxin cyclodepsipeptides (compounds 5⁻7) and cyclonerodiol sesquiterpenes (compounds 8⁻10) from rice medium. The structures and absolute configurations of novel (compounds 1, 8, and 9) and known compounds were elucidated by extensive spectroscopic analyses, X-ray crystallographic analysis, and ECD calculations. All isolated compounds were evaluated for cytotoxic, nematicidal, and antifungal activities, as well as brine shrimp lethality. The novel compound 1 exhibited significant cytotoxic activities against the human cancer cell lines MCF-7, SW480, and HL-60, with IC<sub>50</sub> values of 0.079, 0.107, and 0.149 μM, respectively. In addition, it also showed significant brine shrimp lethality, with an LD<sub>50</sub> value of 0.48 μM, and moderate nematicidal activity against <i>Heterodera avenae</i>, with an LC<sub>50</sub> value of 94.9 μg/mL. This study constitutes the first report on the cytotoxic and nematicidal potential of trichomide cyclodepsipeptides.
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