Kiiacylphnols A−H, eight undescribed polycyclic polyprenylated acylphloroglucinols with anticancer activities from Hypericum przewalskii Maxim

Kiiacylphnols A−H, eight previously undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs), along with two known congeners (hyperforcinol F and oxepahyperforin), were obtained from Hypericum przewalskii Maxim . The structures of these metabolites were confirmed by spectroscopic analyses, quantum-chemical 1 H and 13 C NMR calculations with DP4+ analyses, electronic circular dichroism (ECD) comparisons and calculations. Kiiacylphnols A and B were the first [3.3.1]-type PPAPs with an unusual octahydrooxireno[2,3- i ]chromene scaffold bearing a rare 6/6/6/3 ring system. More significantly, kiiacylphnol A and oxepahyperforin displayed cytotoxicity against acute myeloid leukemia and diffuse large B-cell lymphoma cell lines by inducing cell apoptosis. Eight previously undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) and two known congeners were isolated from Hypericum przewalskii Maxim., and their cytotoxic activities were evaluated. • Eight undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) were obtained. • Kiiacylphnols A and B possessed an unusual octahydrooxireno[2,3-i]chromene scaffold. • Kiiacylphnol A and oxepahyperforin displayed cytotoxicity by inducing cell apoptosis.