Chiral separation and absolute configurations of two pairs of racemic polyprenylated benzophenones from Hypericum sampsonii

(±) Sampsonins A-B (1-2), two pairs of racemic polyprenylated benzophenones, were isolated from the aerial parts of Hypericum sampsonii and successfully separated by chiral HPLC column. Their structures were elucidated by spectroscopic analyses, X-ray diffraction analysis, and quantum chemical calculation of ECD method. Besides, the plausible biogenetic pathways of 1-2 were proposed, and all of them were evaluated for RXRα transcriptional-inhibitory activities and cytotoxicity against HeLa cells.

Graphical abstract(±) Sampsonins A-B (1-2), two pairs of racemic polyprenylated benzophenones, were isolated from the aerial parts of Hypericum sampsonii and successfully separated by chiral HPLC column. The chiral separation, structure elucidation, plausible biogenetic pathways and biological activity evaluation of (±) 1-2 will be reported in this paper.Download high-res image (177KB)Download full-size image