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

Ruifei Zhang; Zhuo Cheng; Qiong Fang; Edward J Kennelly; Chunlin Long

doi:10.1016/j.phytochem.2022.113500

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

Phytochemistry. 2023 Jan:205:113500. doi: 10.1016/j.phytochem.2022.113500. Epub 2022 Nov 13.

Authors

Ruifei Zhang¹, Zhuo Cheng², Qiong Fang³, Edward J Kennelly⁴, Chunlin Long⁵

Affiliations

¹ Key Laboratory of Ecology and Environment in Minority Areas (Minzu University of China), National Ethnic Affairs Commission, Beijing, 100081, People's Republic of China; College of Life and Environmental Sciences, Minzu University of China, Beijing, 100081, People's Republic of China. Electronic address: ruifeizhang@yeah.net.
² Key Laboratory of Ecology and Environment in Minority Areas (Minzu University of China), National Ethnic Affairs Commission, Beijing, 100081, People's Republic of China; College of Life and Environmental Sciences, Minzu University of China, Beijing, 100081, People's Republic of China. Electronic address: 18515952092@163.com.
³ Key Laboratory of Ecology and Environment in Minority Areas (Minzu University of China), National Ethnic Affairs Commission, Beijing, 100081, People's Republic of China; College of Life and Environmental Sciences, Minzu University of China, Beijing, 100081, People's Republic of China. Electronic address: 17710041228@163.com.
⁴ Department of Biological Sciences, Lehman College, City University of New York, Bronx, NY, 10468, USA; Ph.D. Program in Biology, The Graduate Center, City University of New York, 365 Fifth Avenue, New York, NY, 10016, USA. Electronic address: EDWARD.KENNELLY@lehman.cuny.edu.
⁵ Key Laboratory of Ecology and Environment in Minority Areas (Minzu University of China), National Ethnic Affairs Commission, Beijing, 100081, People's Republic of China; College of Life and Environmental Sciences, Minzu University of China, Beijing, 100081, People's Republic of China; Key Laboratory of Ethnomedicine (Minzu University of China), Ministry of Education, Beijing, 100081, People's Republic of China; Key Laboratory of Mass Spectrometry Imaging and Metabolomics (Minzu University of China), National Ethnic Affairs Commission, Beijing, 100081, People's Republic of China. Electronic address: long@mail.kib.ac.cn.

PMID: 36379320
DOI: 10.1016/j.phytochem.2022.113500

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, (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 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.

Keywords: Cytotoxicity; Hypericaceae; Hypericum hengshanense W. T. Wang; Hyphengshanols A–D; Phloroglucinols.

MeSH terms

China
Humans
Hypericum*
Monoterpenes / pharmacology

Substances

Monoterpenes