Rubiyunnanins C-H, cytotoxic cyclic hexapeptides from Rubia yunnanensis inhibiting nitric oxide production and NF-κB activation

被引:97
作者
Fan, Jun-Ting [1 ,2 ]
Su, Jia [1 ,2 ]
Peng, Yan-Min [2 ,3 ]
Li, Yan [1 ]
Li, Jia [3 ]
Zhou, Yu-Bo [3 ]
Zeng, Guang-Zhi [1 ]
Yan, He [1 ,2 ]
Tan, Ning-Hua [1 ]
机构
[1] Chinese Acad Sci, State Key Lab Phytochem & Plant Resources W China, Kunming Inst Bot, Kunming 650204, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Mat Med, Natl Ctr Drug Screen, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
Rubia yunnanensis; Rubiyunnanins C-H; Cyclopeptides; Cytotoxicity; Inhibition of NO production; NF-kappa B pathway inhibitors; ANTITUMOR BICYCLIC HEXAPEPTIDES; BOUVARDIA-TERNIFOLIA; PROTEIN-SYNTHESIS; RA-VII; CONSTITUENTS; CORDIFOLIA; TRITERPENOIDS; RADIX; XI;
D O I
10.1016/j.bmc.2010.10.019
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Six new (rubiyunnanins C-H, 1-6) and five known (7-11) cyclic hexapeptides were isolated from the roots of Rubia yunnanensis (Franch.) Diels. The structures and stereochemistry of 1-6 were established by extensive spectroscopic analyses and chemical methods. All compounds (1-11) not only exhibited cytotoxic activities against a panel of eleven cancer cell lines with IC50 values ranging from 0.001 to 56.24 mu M, but also exerted inhibitory activities against nitric oxide (NO) production in LPS and IFN-gamma-induced RAW 264.7 murine macrophages with IC50 values ranging from 0.05 to 12.68 mu M. Furthermore, this is the first time it is being reported that compounds 2 and 7-10 significantly inhibited TNF-alpha-induced NF-kappa B activation in HEK-293-NF-kappa B luciferase stable cells with IC50 values of 35.07, 0.03, 1.69, 12.64 and 1.18 mu M, respectively. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8226 / 8234
页数:9
相关论文
共 38 条
[1]  
[Anonymous], 1975, DIAN NAN BEN CAO
[2]   SOLUTION FORMS OF BOUVARDIN AND RELATIVES FROM NMR-STUDIES - 6-O-METHYLBOUVARDIN [J].
BATES, RB ;
COLE, JR ;
HOFFMANN, JJ ;
KRIEK, GR ;
LINZ, GS ;
TORRANCE, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (05) :1343-1347
[3]  
Chen Y.Q., 1991, CHINESE J ORG CHEM, V11, P523
[4]  
Du Liang-Cheng, 2009, Acta Botanica Yunnanica, V31, P374, DOI 10.3724/SP.J.1143.2009.09093
[5]   Rubiyunnanins A and B, two novel cyclic hexapeptides from Rubia yunnanensis [J].
Fan, Jun-Ting ;
Chen, Yi-Shan ;
Xu, Wen-Yan ;
Du, Liangcheng ;
Zeng, Guang-Zhi ;
Zhang, Yu-Mei ;
Su, Jia ;
Li, Yan ;
Tan, Ning-Hua .
TETRAHEDRON LETTERS, 2010, 51 (52) :6810-6813
[6]   RA-VII, a cyclic depsipeptide, changes the conformational structure of actin to cause G2 arrest by the inhibition of cytokinesis [J].
Fujiwara, H ;
Saito, S ;
Hitotsuyanagi, Y ;
Takeya, K ;
Ohizumi, Y .
CANCER LETTERS, 2004, 209 (02) :223-229
[7]  
He Min, 1993, Acta Botanica Yunnanica, V15, P408
[8]  
ITOKAWA H, 1984, CHEM PHARM BULL, V32, P3216
[9]  
ITOKAWA H, 1983, CHEM PHARM BULL, V31, P1424
[10]  
ITOKAWA H, 1984, CHEM PHARM BULL, V32, P284