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Benzofurans from Eupatorium chinense enhance insulin-stimulated glucose uptake in C2C12 myotubes and suppress inflammatory response in RAW264.7 macrophages
Jiang-HuanKe1; Li-ShaZhang1; Shi-XinChen1; Sheng-NanShen2; TianZhang2; Chang-XinZhou1; Jian-XiaMo1; Li-GenLin2; Li-SheGan1,3
2019
Source PublicationFitoterapia
ISSN0367-326X
Volume134Pages:346-354
Abstract

Fourteen acetylbenzofuran derivatives, including three undescribed carbon skeletons with a newly formed hexane or benzene ring on the other side of the benzofuran ring, (±)-eupatonin A (1), (±)-eupatonin B (2), and eupatonin C (3), two new benzofurans (−)-12β-hydroxygynunone (4) and (+)-12-hydroxyl-13-noreuparin (5), as well as 9 known ones (614), were isolated from 95% ethanol extract of the roots of Eupatorium chinense. Their structures were determined by spectroscopic methods and quantum chemical DFT and TDDFT calculations of the NMR chemical shifts and ECD spectra, which helped in the determination of the relative configurations of 1 and 2 and the absolute configurations of 4 and 5, respectively. 1 and 2 were further identified to be racemic mixtures by chiral HPLC analysis. All compounds were evaluated for insulin-stimulated glucose uptake in differentiated C2C12 myotubes. Compounds 13451112, and 13 markedly enhanced insulin-mediated glucose uptake. (±)-Eupatonin A (1) activated the IRS-1/Akt/GSK-3β signaling pathway and enhanced insulin stimulated GLUT4 membrane translocation in C2C12 myotubes. On LPS stimulated RAW264.7 macrophages, several compounds exhibited significant inhibitory effect on NO production with IC50 values ranging from 4.94 to 9.70 μΜ. (±)-Eupatonin A (1) again dose-dependently suppressed LPS-induced NO production and decreased the expression of inducible NO synthase (iNOS), through inhibiting NF-κB activity.

KeywordGlucose Uptake Benzofuran Eupatorium Chinense Quantum Chemical Calculation Anti-inflammation
DOIhttps://doi.org/10.1016/j.fitote.2019.03.007
Indexed BySCI
Language英语
WOS Research AreaPharmacology & Pharmacy
WOS SubjectChemistry, Medicinal ; Pharmacology & Pharmacy
WOS IDWOS:000468710300042
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Cited Times [WOS]:2   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Corresponding AuthorLi-SheGan
Affiliation1.College of Pharmaceutical Sciences, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, People's Republic of China.
2.State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao 999078, People's Republic of China.
3.Hangzhou Institute of Innovative Medicine, Zhejiang University, 291 Fucheng Road, Hangzhou 310018, People's Republic of China.
Recommended Citation
GB/T 7714
Jiang-HuanKe,Li-ShaZhang,Shi-XinChen,et al. Benzofurans from Eupatorium chinense enhance insulin-stimulated glucose uptake in C2C12 myotubes and suppress inflammatory response in RAW264.7 macrophages[J]. Fitoterapia,2019,134:346-354.
APA Jiang-HuanKe.,Li-ShaZhang.,Shi-XinChen.,Sheng-NanShen.,TianZhang.,...&Li-SheGan.(2019).Benzofurans from Eupatorium chinense enhance insulin-stimulated glucose uptake in C2C12 myotubes and suppress inflammatory response in RAW264.7 macrophages.Fitoterapia,134,346-354.
MLA Jiang-HuanKe,et al."Benzofurans from Eupatorium chinense enhance insulin-stimulated glucose uptake in C2C12 myotubes and suppress inflammatory response in RAW264.7 macrophages".Fitoterapia 134(2019):346-354.
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