Monoterpenoid acylphloroglucinols from Hypericum hengshanense W. T. Wang with antiproliferative activities. (January 2023)

• Record Type: Journal Article
• Authors: Zhang, Ruifei; Cheng, Zhuo; Fang, Qiong; Kennelly, Edward J.; Long, Chunlin
• Is Part Of: Phytochemistry. Volume 205(2023)
• Publication Date: 2023-01
• Subjects: Hypericum hengshanense W. T. Wang -- Hypericaceae -- Phloroglucinols -- Hyphengshanols A–D -- Cytotoxicity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2022.113500
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: 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 IC50 ranging from 7.54 to 45.70 μM. Graphical abstract: 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. Image 1 Highlights: 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.