Nine prenylated acylphloroglucinols with potential anti-depressive and hepatoprotective activities from Hypericum scabrum

In our screening program for new biologically active secondary metabolites, nine new polycyclic polyprenyled acylphloroglucinols, hyperscabins D-L, together with three known compounds, were obtained from the aerial parts of Hypericum scabrum. The chemical structures of 1-9 were characterized by extensive spectroscopic analyses, nuclear magnetic resonance calculation with DP4+ probability analysis, and the electronic circular dichroism spectra were calculated. Compound 1 was an unusual prenylated acylphloroglucinol decorated with a 5-oxaspiro [4,5] deca-1,9-dione skeleton. Compound 2 was a newly identified spirocyclic polyprenylated acylphloroglucinol possessing a rare 5,5-spiroketal segment. Compounds 3, 8, and 10 (10 mu M) exhibited pronounced hepatoprotective activity against D-galactosamine-induced WB-F344 cell damage in vitro assays. All test compounds (1, 3, and 7-12) demonstrated potential inhibitory effects at 10 mu M against noradrenalinet ([H-3]-NE) reuptake in rat brain synaptosome.

Automated summary

In our screening program, nine new polycyclic polyprenyled acylphloroglucinols were discovered from Hypericum scabrum, along with three known compounds. These compounds exhibited diverse chemical structures and potential biological activities, such as hepatoprotective effects and inhibition of noradrenaline reuptake.