Picrorhizones A-H, Polyprenylated Benzoylphloroglucinols from the Stem Bark of .

Eight new polyprenylated benzoylphloroglucinol derivatives (-) and four known analogues (-) were isolated from the stem bark of . Their structures were determined by spectroscopic data analysis (1D and 2D NMR and HRESIMS), and the absolute configurations were established by single-crystal X-ray diffraction combined with experimental and calculated ECD data. The new metabolites represent rare examples of benzoylphloroglucinols bearing a cyclobutyl-containing side chain. The isolated compounds were evaluated for their cytotoxic properties against five types of human cancer cells (KB, HeLa S3, MCF-7, Hep G2, and HT-29 cells) and their inhibitory activities against COX-1 and COX-2 enzymes. The cytotoxicity results showed that compound was active against KB, HeLa S3, MCF-7, and Hep G2 cancer cells, with IC values ranging from 5.9 to 9.4 μM. Among the compounds tested for cyclooxygenase inhibition, compound possessed the highest inhibitory effect toward COX-1 (35.2 ± 9.6% inhibition at 20 μM).