title: Soluble epoxide hydrolase inhibitory and anti-inflammatory components from the leaves of Eucommia ulmoides Oliver (duzhong).
abstract: Eucommia ulmoides leaves have been used as a functional food and drink in China. The purpose of this study was to identify the bioactive constituents with soluble epoxide hydrolase (sEH) inhibitory activity and anti-inflammatory properties. Twenty-seven known compounds (1-27) were isolated from the leaves of E. ulmoides Oliver, and their structures were identified by NMR and ESIMS analysis; three of these, 2,5-dimethoxy-3-glucopyranosyl cinnamic alcohol (11), foliasalacioside E2 (26), and icariside F2 (27), were obtained from this plant for the first time. Compounds 1-7 exhibited soluble epoxide hydrolase (sEH) inhibitory activity at 100 μM; among them, quercetin (1) and kaempferol (5) displayed potential activities with IC50 values of 22.5 ± 0.9 and 31.3 ± 2.6 μM, respectively, with noncompetitive inhibition mode. Nuclear factor kappa B (NF-κB) inhibitory activity of the isolated compounds was evaluated by the NF-κB liciferase assay in HepG2 cells. Compounds 1, 9, 20, and 27 displayed potent NF-κB inhibitory effects, with IC50 values of 15.14 ± 2.29, 15.23 ± 2.34, 16.88 ± 2.17, and 16.25 ± 2.19 μM, respectively, whereas other compounds showed weak inhibition of NF-κB transcriptional activity ranging from 17.54 to 92.6 μM. A structure-activity relationship of flavonoids 1-9 was also discussed. The results obtained in this work might contribute to the understanding of pharmacological activities of E. ulmoides leaves and further investigation on its potential application values for food and drug.
authors: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University , Yangling 712100, Shaanxi, PR China.
authors: Meng-Meng
authors: MM
authors: Bai
authors: Wei
authors: W
authors: Shi
authors: Jun-Mian
authors: JM
authors: Tian
authors: Ming
authors: M
authors: Lei
authors: Jang Hoon
authors: JH
authors: Kim
authors: Ya Nan
authors: YN
authors: Sun
authors: Young Ho
authors: YH
authors: Kim
authors: Jin-Ming
authors: JM
authors: Gao
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002681:China; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D004851:Epoxide Hydrolases / Q000032:analysis / Q000037:antagonists & inhibitors*; D031283:Eucommiaceae / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D016328:NF-kappa B / Q000037:antagonists & inhibitors / Q000276:immunology; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000893:Anti-Inflammatory Agents; D004791:Enzyme Inhibitors; D016328:NF-kappa B; D010936:Plant Extracts; D004851:Epoxide Hydrolases
keywords: Eucommia ulmoides; NF-κB inhibitory effects; eucommioside-I; flavonoid; megastigmane; soluble epoxide hydrolase