Bioactive Acylphloroglucinols with Adamantyl Skeleton from Hypericum sampsonii

Hyperisampsins A–D (1–4), with tetracyclo­[6.3.1.13,10.03,7]­tridecane skeletons and seven biogenetically related congeners (5–11), were isolated from Hypericum sampsonii. Their structures were elucidated by comprehensive spectroscopic techniques. The absolute configuration of 1 was established by ECD calculations, and those of 5 and 9 were confirmed by single X-ray crystallographic analyses. Hyperisampsins A and D showed potent anti-HIV activities with EC50 of 2.97 and 0.97 μM and selectivity index of 4.80 and 7.70, respectively.