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学科主题: 药学
题名:
Sesquiterpenes from Artemisia argyi: Absolute Configurations and Biological Activities
作者: Wang, Shu1,2; Sun, Jian1; Zeng, Kewu1; Chen, Xiaoguang3,4; Zhou, Wanqi3,4; Zhang, Chen1; Jin, Hongwei1; Jiang, Yong1; Tu, Pengfei1
关键词: Natural products ; Terpenoids ; Configuration determination ; Circular dichroism ; Cytotoxicity ; Nitric oxide
刊名: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2014-02-01
DOI: 10.1002/ejoc.201301445
卷: 2014, 期:5, 页:973-983
收录类别: SCI ; IC
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
关键词[WOS]: OPTICAL ROTATORY DISPERSION ; X-RAY CRYSTALLOGRAPHY ; NF-KAPPA-B ; CIRCULAR-DICHROISM ; DIMERIC GUAIANOLIDES ; NATURAL-PRODUCTS ; LACTONES ; NMR ; STEREOCHEMISTRY ; CONSTITUENTS
英文摘要:

Nine guaiane-type sesquiterpenes and one eudesmane-type one - namely argyinolides A-J (1-10) - as well as nine known analogues were isolated from the leaves of Artemisia argyi Levl. et Vant. Their structures were determined by interpretation of spectroscopic data (MS, 1D and 2D NMR). A combination of X-ray crystal diffraction, specific optical rotations, CD spectroscopy, ECD calculation, and Mosher ester methods was employed to resolve the absolute configurations of the isolated compounds. Biological investigations into their cytotoxicities and anti-inflammatory effects showed that 1, 13, 16, and 18 were remarkably cytotoxic against Bel-742 and/or A549 cells, with IC50 values of 3.3-6.0 M, whereas 7, 11-13, 16, and 18 exhibited sound inhibitory activity on LPS-stimulated NO production in BV-2 microglial cells, with IC50 values ranging from 3.2 to 8.6 M. In addition, a brief discussion on the applicability of Geissman′s rule for the sesquiterpene lactones, the probable reason for the presence of chlorine-containing sesquiterpenes, and preliminary structure-activity relationships (SARs) are included.

语种: 英语
所属项目编号: 30973629 ; 81222051 ; 81303253 ; 81373294 ; 2012ZX 09301002-002-002 ; 2012ZX09304-005
项目资助者: National Natural Science Foundation of China (NSFC) ; National Key Technology R&amp ; D Program "New Drug Innovation" of China
WOS记录号: WOS:000331266600009
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/54734
Appears in Collections:北京大学药学院_期刊论文

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作者单位: 1.Peking Univ, Hlth Sci Ctr, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
2.Chinese Peoples Armed Police Forces, Logist Coll, Dept Med Chem & Pharmaceut Anal, Tianjin 300162, Peoples R China
3.Chinese Acad Med Sci, Inst Mat Med, Beijing 100050, Peoples R China
4.Peking Union Med Coll, Beijing 100050, Peoples R China

Recommended Citation:
Wang, Shu,Sun, Jian,Zeng, Kewu,et al. Sesquiterpenes from Artemisia argyi: Absolute Configurations and Biological Activities[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2014,2014(5):973-983.
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