Seven previously unidentified polycyclic polyprenylated acylphloroglucinol (PPAP) derivatives hypseudohenrins A-G, along with six known analogs, were isolated from the aerial portion of Hypericum pseudohenryi. Their structures were determined by NMR, ECD and X-ray crystallographic spectroscopy. These compounds were screened for anti-inflammatory activity, and hypseudohenrins B and G (at the concentration of 10 μM) showed NO production inhibition ratios of 52.56% and 54.01%, respectively, which imply good anti-inflammatory activity. In particular, uraloidin A exhibited an NO inhibition ratio of 90.61%, while that ratio of the positive control compound dexamethasone was 94.88%. Additionally, anti-cancer and neural-protective activities were screened, but none of these compounds showed desirable activity.