Chemical constituents from the flowers of Hypericum monogynum L. with COX-2 inhibitory activity

Ya-Nan Li; Yan-Rong Zeng; Jue Yang; Wenwen He; Junlei Chen; Lulu Deng; Ping Yi; Lie-Jun Huang; Wei Gu; Zhan-Xing Hu; Chun-Mao Yuan; Xiao-Jiang Hao

doi:10.1016/j.phytochem.2021.112970

Chemical constituents from the flowers of Hypericum monogynum L. with COX-2 inhibitory activity

Phytochemistry. 2022 Jan:193:112970. doi: 10.1016/j.phytochem.2021.112970. Epub 2021 Oct 21.

Authors

Ya-Nan Li¹, Yan-Rong Zeng², Jue Yang¹, Wenwen He¹, Junlei Chen¹, Lulu Deng¹, Ping Yi¹, Lie-Jun Huang¹, Wei Gu¹, Zhan-Xing Hu¹, Chun-Mao Yuan³, Xiao-Jiang Hao⁴

Affiliations

¹ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang, 550014, China.
² State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang, 550014, China; School of Ethnic Medicine, Guizhou Minzu University, Guiyang, People's Republic of China, Guiyang, 550025, China.
³ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang, 550014, China. Electronic address: yuanchunmao01@126.com.
⁴ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang, 550014, China; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Boanty, Chinese Academy of Science, Kunming, 650201, China. Electronic address: haoxj@mail.kib.ac.cn.

PMID: 34689099
DOI: 10.1016/j.phytochem.2021.112970

Abstract

Hypericum monogynum L. (Hypericaceae) has been used as a folk Chinese medicine for the treatment of inflammatory related diseases. Cyclooxygenase-2 (COX-2) is a crucial target for the development of agents to treat inflammation. To search for anti-inflammatory compounds from traditional Chinese medicines, a chemical constituent study along with COX-2 inhibitory activity analysis was performed for this plant. In this study, sixteen chemical monomers, including three undescribed oxidative degradation polycyclic polyprenylated acylphloroglucinols (PPAPs, hypemoins C-E), two undescribed PPAPs (hypemoins A and B), and 11 known compounds, were identified from the flowers of H. monogynum. Their structures were characterized by HRESIMS, NMR techniques, ECD, and single crystal X-ray diffraction. Four flavonoid derivatives showed remarkable COX-2 inhibitory activities, with IC₅₀ values ranging from 0.220 ± 0.006 to 1.655 ± 0.098 μM. Among these compounds, the possible recognition mechanism between quercetin 3-(6″-O-caffeoyl)-β-3-D-galactoside and COX-2 was predicted by molecular docking analysis. Moreover, the multidrug resistance reversal activities for the selected compounds were evaluated.

Keywords: COX-2 inhibitors; Chemical constituents; Flavonoids; Hypericaceae; Hypericum monogynum L.; Polycyclic polyprenylated acylphloroglucinols.

MeSH terms

Cyclooxygenase 2
Flowers
Hypericum*
Molecular Docking Simulation
Molecular Structure
Phloroglucinol / pharmacology

Substances

Phloroglucinol
Cyclooxygenase 2