Sesquiterpene lactones from Artemisia verlotorum and their anti-inflammatory activities

被引:10
作者
Wang, Mengyu [1 ,2 ,3 ]
Yang, Yue [2 ,3 ]
Ke, Changqiang [2 ,3 ]
Yao, Sheng [2 ,3 ,4 ,5 ]
Feng, Zheling [2 ,3 ]
Tang, Chunping [2 ,3 ]
Ye, Yang [1 ,2 ,3 ,4 ,6 ]
机构
[1] Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Mat Med, Nat Prod Chem Dept, Shanghai 201203, Peoples R China
[4] Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
[5] Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
[6] ShanghaiTech Univ, Sch Life Sci & Technol, Shanghai 201210, Peoples R China
基金
中国国家自然科学基金;
关键词
Artemisia verlotorum; Verlotolides A -G; DFT NMR calculation; TDDFT ECD calculation; X-ray diffraction; Anti-inflammation; AQUEOUS CRUDE EXTRACTS; IN-VITRO; CHEMICAL-CONSTITUENTS; ESSENTIAL OIL; VERLOTIORUM; LAMOTTE; ALANTOLIDES; COMPOSITAE; VIVO;
D O I
10.1016/j.fitote.2023.105560
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Seven new sesquiterpenoids (1-7) and 19 known analogues were isolated from the whole plant of Artemisia verlotorum. Their structures were determined by extensive analysis of 1D and 2D NMR and HRESIMS data, electronic circular dichroism (ECD) spectra, density functional theory (DFT) NMR calculations, and time dependent density functional theory (TDDFT) ECD calculations. The absolute configurations of 1, 3, 5 and 7 were confirmed by single crystal X-ray diffraction experiments. Compounds 1 and 2 possess a rarely reported 5/8-bicyclic skeleton, while both compounds 3 and 4 were uncommon iphionane-type sesquiterpenoids. Eudesmane sesquiterpenoids (5-17) reported in this study are all 7,8-cis-lactones, of which, compound 7 represents the first eudesmane sesquiterpene with an oxygen bridge connecting C-5 and C-11. All the compounds were tested in vitro for their anti-inflammatory activities in LPS-stimulated RAW 264.7 murine macrophages. Compound 18 showed a potent inhibitory effect on NO production, with IC50 values of 3.08 & PLUSMN; 0.61 & mu;M.
引用
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页数:11
相关论文
共 51 条
[1]  
ADEKENOV SM, 1991, KHIM PRIR SOEDIN+, P648
[2]   Current status and contemporary approaches to the discovery of antitumor agents from higher plants [J].
Agarwal, Garima ;
Carcache, Peter J. Blanco ;
Addo, Ermias Mekuria ;
Kinghorn, A. Douglas .
BIOTECHNOLOGY ADVANCES, 2020, 38
[3]  
[Anonymous], 2017, CONFLEX 8 COMP PROGR
[4]   ISOMERIC HYDROPEROXYEUDESMANOLIDES FROM ARTEMISIA-UMBELLIFORMIS [J].
APPENDINO, G ;
GARIBOLDI, P ;
NANO, GM .
PHYTOCHEMISTRY, 1983, 22 (12) :2767-2772
[5]   Genotoxic potential of aqueous extracts of Artemisia verlotorum on the cell cycle of Allium cepa [J].
de Souza L.F.B. ;
Laughinghouse IV H.D. ;
Pastori T. ;
Tedesco M. ;
Kuhn A.W. ;
do Canto-Dorow T.S. ;
Tedesco S.B. .
International Journal of Environmental Studies, 2010, 67 (06) :871-877
[6]  
BOHLMANN F, 1972, TETRAHEDRON LETT, P621
[7]  
BOHLMANN F, 1983, LIEBIGS ANN CHEM, P2227
[8]   SpecDis: Quantifying the Comparison of Calculated and Experimental Electronic Circular Dichroism Spectra [J].
Bruhn, Torsten ;
Schaumloeffel, Anu ;
Hemberger, Yasmin ;
Bringmann, Gerhard .
CHIRALITY, 2013, 25 (04) :243-249
[9]  
Calderone V, 1999, PHYTOTHER RES, V13, P645, DOI 10.1002/(SICI)1099-1573(199912)13:8<645::AID-PTR496>3.0.CO
[10]  
2-M