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Sesquiterpenes from Artemisia argyi: Absolute Configurations and Biological Activities
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
2014-02-01
DOI10.1002/ejoc.201301445
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
资助者National Natural Science Foundation of China (NSFC) ; National Key Technology R&amp ; D Program "New Drug Innovation" of China ; National Natural Science Foundation of China (NSFC) ; National Key Technology R&amp ; D Program "New Drug Innovation" of China
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
资助者National Natural Science Foundation of China (NSFC) ; National Key Technology R&amp ; D Program "New Drug Innovation" of China ; 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
引用统计
被引频次:9[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/54734
专题北京大学药学院
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
推荐引用方式
GB/T 7714
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.
APA Wang, Shu.,Sun, Jian.,Zeng, Kewu.,Chen, Xiaoguang.,Zhou, Wanqi.,...&Tu, Pengfei.(2014).Sesquiterpenes from Artemisia argyi: Absolute Configurations and Biological Activities.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2014(5),973-983.
MLA Wang, Shu,et al."Sesquiterpenes from Artemisia argyi: Absolute Configurations and Biological Activities".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2014.5(2014):973-983.
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