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Tricarabrols A-C, three anti-inflammatory sesquiterpene lactone trimers featuring a methylene-tethered linkage from Carpesium faberi

文献类型：期刊论文

作者Yuan, Jie1,2,3; Wen, Xuelan4; Ke, Chang-Qiang1,2; Zhang, Tian5; Lin, Ligen5; Yao, Sheng1,2; Goodpaster, Jason D.4; Tang, Chunping1,2; Ye, Yang1,2,6
刊名ORGANIC CHEMISTRY FRONTIERS
出版日期2020-06-07
卷号7期号:11页码:1374-1382
ISSN号2052-4129
DOI10.1039/d0qo00093k
通讯作者Goodpaster, Jason D.(jgoodpas@umn.edu) ; Tang, Chunping(tangcp@simm.ac.cn) ; Ye, Yang(yye@simm.ac.cn)
英文摘要Tricarabrols A-C (1-3), three sesquiterpene lactone trimers, were identified from Carpesium faberi. Tricarabrols A and B are a pair of stereoisomers possessing a novel C-44 skeleton featuring a methylene-tethered linkage among the sesquiterpene scaffolds. Besides the unique linkage of the cyclopentane ring, tricarabrol C also manifests a methylene bridge. Their full structures were established on the basis of spectroscopic data and further confirmed by computational methods. The biosynthetic pathways involving the Alder-ene reaction, [3 + 2] cycloaddition, and Michael addition reaction were proposed. Tricarabrols A and B (1-2) significantly inhibited the nitric oxide production on lipopolysaccaride-stimulated RAW264.7 macrophages with IC50 values of 2.90 and 4.52 mu M, respectively, compared with the positive control indomethacin. Further studies indicated that the anti-inflammatory effect of tricarabrol A was mediated through inhibiting the phosphorylation and nuclear translocation of nuclear factor-kappa B.
WOS关键词MOLECULAR-ORBITAL METHODS ; GAUSSIAN-TYPE BASIS ; NF-KAPPA-B ; BIOMIMETIC SYNTHESES ; DIMERS
资助项目National Natural Science Foundation of China[21920102003] ; National Natural Science Foundation of China[81673327] ; National Natural Science Foundation of China[81872754] ; China National Key RD Program[2017YFE0195100] ; Science and Technology Development Fund, Macao S.A.R[FDCT 0031/2019/A1]
WOS研究方向Chemistry
语种英语
出版者ROYAL SOC CHEMISTRY
WOS记录号WOS:000538168500008
源URL[http://119.78.100.183/handle/2S10ELR8/291639]  
专题新药研究国家重点实验室
通讯作者Goodpaster, Jason D.; Tang, Chunping; Ye, Yang
作者单位1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, Nat Prod Chem Dept, Shanghai 201203, Peoples R China
3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
4.Univ Minnesota TWin Cities, Dept Chem, Minneapolis, MN 55455 USA
5.Univ Macau, Inst Chinese Med Sci, State Key Lab Qual Res Chinese Med, Taipa, Macao, Peoples R China
6.ShanghaiTech Univ, Sch Life Sci & Technol, Shanghai 201210, Peoples R China
推荐引用方式
GB/T 7714		 Yuan, Jie,Wen, Xuelan,Ke, Chang-Qiang,et al. Tricarabrols A-C, three anti-inflammatory sesquiterpene lactone trimers featuring a methylene-tethered linkage from Carpesium faberi[J]. ORGANIC CHEMISTRY FRONTIERS,2020,7(11):1374-1382.
APA Yuan, Jie.,Wen, Xuelan.,Ke, Chang-Qiang.,Zhang, Tian.,Lin, Ligen.,...&Ye, Yang.(2020).Tricarabrols A-C, three anti-inflammatory sesquiterpene lactone trimers featuring a methylene-tethered linkage from Carpesium faberi.ORGANIC CHEMISTRY FRONTIERS,7(11),1374-1382.
MLA Yuan, Jie,et al."Tricarabrols A-C, three anti-inflammatory sesquiterpene lactone trimers featuring a methylene-tethered linkage from Carpesium faberi".ORGANIC CHEMISTRY FRONTIERS 7.11(2020):1374-1382.

入库方式： OAI收割

来源：上海药物研究所

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