Abstract: Two new type B polycyclic polyprenylated acylphloroglucinols (PPAPs) ( 1 and 2 ) and a known biogenetic precursor hyperbeanol Q ( 3 ) were isolated from the root extract of Hypericum beanii, a medicinal plant widespread in southwest China. Their chemical structures were elucidated by 1D/2D NMR and HRESIMS data analysis, and absolute configurations were determined through detailed electric circular dichroism (ECD) analysis including ECD exciton chirality, Mo₂(OAc)₄-induced ECD, and ECD comparison. Of these compounds, hyperbeone A ( 1 ) is a typical 3.3.1-type B PPAP with an unusual C-1 geranyl side chain, and hyperberin C ( 2 ) possesses a rare bicyclo5.3.1hendecane core. Taking compound 3 as a starting point, a plausible biosynthetic pathway to the bicyclic type B frameworks of 1 and 2 was proposed.