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

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

Journal: Phytochemistry 2022;205():113500

PMID: 36379320

Full Text on Elsevier Science View on PubMed

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 IC ranging from 7.54 to 45.70 μM.

Address: 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: [email protected].; 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: [email protected].; 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: [email protected].; 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: [email protected].; 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: [email protected].

DOI: 10.1016/j.phytochem.2022.113500

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MeSH Terms: Humans, China, Hypericum, Monoterpenes