绝对构型
立体化学
植物化学
细胞毒性
化学
金丝桃属
间苯三酚
圆二色性
电喷雾电离
二维核磁共振波谱
植物化学
质谱法
有机化学
植物
色谱法
生物
体外
生物化学
作者
Ruifei Zhang,Zhuo Cheng,Qiong Fang,Edward J. Kennelly,Chunlin Long
标识
DOI:10.1016/j.phytochem.2022.113500
摘要
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, (9 S ,2′ S )-dauphinol F, and (8 R ,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 spectroscopy (NMR) data. The absolute configurations were determined by experimental and calculated electronic circular 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 IC 50 ranging from 7.54 to 45.70 μM. Ten undescribed monoterpenoid acylphloroglucinols and 15 known analogs were isolated and identified, including six pairs of stereoisomers. Their cytotoxicity against five cancer cell lines was evaluated. • MAPs were isolated from Hypericum hengshanense including 10 undescribed ones. • The absolute configurations of 16 MAPs were determined by ECD calculations. • Six pairs of stereoisomers were separated via chiral-phase HPLC. • Sixteen isolates showed cytotoxicity against five cancer cell lines.
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