Rearranged Homoadamantane-Type Polycyclic Polyprenylated Acylphloroglucinols from Hypericum pseudohenryi .

Hypseudohenones A-C ( 1 - 3 ), the first rearranged homoadamantane-type polycyclic polyprenylated acylphloroglucinols, were isolated from Hypericum pseudohenryi . Their structures with an unprecedented tricyclo[4.3.1.1 3,8 ]undecane-2,4,10-trione core were determined by spectroscopic analysis, quantum-chemical calculations, and X-ray crystallography. A method for determining the relative configuration at C-3 was established by the peak shape of H-28 or J -value of H-3/H-28. Moreover, 2 - 3 exhibited significant AChE inhibitory activity, and the interactions of 2 - 3 with AChE were evaluated by molecular docking.