Prenylated acylphloroglucinols from the fruits of Hypericum patulum

Twenty-eight prenylated acylphloroglucinols, including the new hypulatones C-F (1-4), have been isolated from the fruits of Hypericum patulum and structurally characterized. Compound 1 represents a rare meroterpenoid formed through the addition of a prenylated acylphloroglucinol unit and a sesquiterpenoid moiety. Spirocyclic polycyclic polyprenylated acylphloroglucinol 2 contains six chiral centers, and its relative configuration was established based on ¹H-¹H coupling constants, conformational analysis, and NOE correlations. The cytotoxic activities of all isolates against two human carcinoma cell lines (Huh-7 and Panc-1) were evaluated using the CCK-8 assay. Bioassay results indicated that compounds 6, 8, and 15 exhibited moderate antiproliferative activity.