Three new oxygenated cyclohexene derivatives, trichocarpeols A (<b>1</b>), B (<b>2</b>), and C (<b>3</b>), along with nine known secondary metabolites, were isolated from the methanolic root extract of <i>Monanthotaxis trichocarpa</i>. They were identified by NMR spectroscopic and mass spectrometric analyses, and the structure of trichocarpeol A (<b>1</b>) was confirmed by single-crystal X-ray diffraction. Out of the 12 isolated natural products, uvaretin (<b>4</b>) showed activity against the Gram-positive bacterium <i>Bacillus subtilis</i> with a MIC value of 18 μM. None of the isolated metabolites was active against the Gram-negative <i>Escherichia coli</i> at a ∼5 mM (2000 μg/mL) concentration. Whereas <b>4</b> showed cytotoxicity at EC<sub>50</sub> 10.2 μM against the MCF-7 human breast cancer cell line, the other compounds were inactive or not tested.