Chemical constituents from the flowers of Hypericum monogynum L. with COX-2 inhibitory activity. (January 2022)

• Record Type: Journal Article
• Authors: Li, Ya-Nan; Zeng, Yan-Rong; Yang, Jue; He, Wenwen; Chen, Junlei; Deng, Lulu; Yi, Ping; Huang, Lie-Jun; Gu, Wei; Hu, Zhan-Xing; Yuan, Chun-Mao; Hao, Xiao-Jiang
• Is Part Of: Phytochemistry. Volume 193(2022)
• Publication Date: 2022-01
• Subjects: Hypericum monogynum L. -- Hypericaceae -- Chemical constituents -- Polycyclic polyprenylated acylphloroglucinols -- Flavonoids -- COX-2 inhibitors; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2021.112970
• Languages: English
• ISSNs: 0031-9422

Abstract

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. Graphical abstract: Sixteen chemical monomers, including three undescribed oxidative degradation polycyclic polyprenylated acylphloroglucinols (PPAPs, hypemoins C–E), two undescribed PPAPs (hypemoins A and B), and 11 phenol derivatives were discovered from the flowers of Hypericum monogynum . Four flavonoids showed remarkably COX-2 inhibitory activities with IC50 values ranging from 0.220 ± 0.006 to 1.655 ± 0.098 μM. Image 1 Highlights: Five undescribed compounds were isolated from Hypericum monogynum. Four flavonoids showed remarkably COX-2 inhibitory activities. The possible recognition mechanism was predicted by molecular docking. The multidrug resistance reversal activity was also evaluated.