Antidepressant polyprenylated acylphloroglucinols from Hypericum ascyron

Phytochemical investigation on the 90% EtOH extract of the air-dried aerial parts of Hypericum ascyron resulted in the isolation of three new polycyclic polyprenylated derivatives ascyronines A-C (1-3). Structural elucidation of all the compounds was performed by spectral methods such as 1D and 2D (¹H-¹H COSY, HMQC, and HMBC) NMR spectroscopy. All the polycyclic polyprenylated acylphloroglucinols were evaluated for their antidepressant activity by inhibiting the reuptake of tritiated serotonin ([³H]-5-HT) and noradrenalinet ([³H]-NE) in rat brain synaptosomes. Compounds 2 and 3 exhibited weak antidepressant activities in the [³H]-5-HT mode.