Monoterpenoid acylphloroglucinols from Hypericum hengshanense W. T. Wang with antiproliferative activities

Hypericum species (Hypericaceae) are a group of important plants with medicinal, edible, and ornamental values. A phytochemical study on the whole plants of H. hengshanense W. T. Wang, a species endemic to China, led to the isolation and elucidation of 25 monoterpenoid acylphloroglucinols (MAPs). Among them, 10 are undescribed compounds, namely hyphengshanols A-D, (+)-empetrilatinol A, (-)-empetrilatinol B, (-)-hyperjovinol A, (9S,2 ' S)-dauphinol F, and (8R,2 ' S)-empetrikathiforin. In addition, the absolute configurations of other six compounds were firstly determined in the current study. The structures were established by ultraviolet (UV), high resolution electrospray ionization mass spectrum (HR-ESI-MS), and nuclear magnetic resonance spectros-copy (NMR) data. The absolute configurations were determined by experimental and calculated electronic cir-cular dichroism (ECD) data analyses. Cytotoxicity assays on five human cell lines HL-60, A549, SMMC-7721, MDA-MB-231, and SW480 revealed that 16 compounds exhibited broad-spectrum antiproliferative activities with IC50 ranging from 7.54 to 45.70 mu M.

Automated summary

Hypericum species (Hypericaceae) are important plants with medicinal, edible, and ornamental values. A study on H. hengshanense led to the discovery and characterization of 25 monoterpenoid acylphloroglucinols (MAPs), including 10 undescribed compounds. The structures were determined using UV, HR-ESI-MS, and NMR, while the absolute configurations were determined through ECD analysis. Furthermore, several compounds exhibited broad-spectrum antiproliferative activities against various human cell lines.