Rearranged ent-kauranoid glycosides from the fruits of Xanthium strumarium and their antiproliferative activity

被引:15
作者
Jiang, Hai [1 ,2 ,3 ]
Ma, Guo-Xu [1 ,2 ]
Yang, Liu [3 ]
Xing, Xu-Dong [3 ]
Yan, Mei-Ling [3 ]
Zhang, Yan-Yan [3 ]
Wang, Qiu-Hong [3 ,4 ]
Kuang, Hai-Xue [3 ]
Xu, Xu-Dong [1 ,2 ]
机构
[1] Minist Educ, Key Lab Bioact Subst & Resources Utilizat Chinese, Inst Med Plant Dev, Peking Union Med Coll, Beijing 100193, Peoples R China
[2] Chinese Acad Med Sci, Beijing 100193, Peoples R China
[3] Heilongjiang Univ Chinese Med, Key Lab Chinese MateriaMed, Minist Educ, Harbin 150040, Peoples R China
[4] Guangdong Pharmaceut Univ, Guangzhou 528458, Guangdong, Peoples R China
关键词
X; strumarium; ent-kauranoid diterpenes; Cytotoxic activity; SESQUITERPENE LACTONES; AERIAL PARTS; DITERPENOIDS; SIBIRICUM;
D O I
10.1016/j.phytol.2016.10.007
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Three new ent-kauranoid glycosides, fructusnoids A-C (1-3) were isolated from the fruits of Xanthium strumarium. Their structures were elucidated by extensive spectroscopic methods, including NMR, MS, and HRESIMS data. Compounds 1-2 are novel examples of rearranged ent-kauranoid diterpenes with missing C-18/19 carbons. All the compounds were evaluated for their antiproliferative activity in vitro against three human cancer cell lines, and compound 3 showed selective cytotoxic activity against the AGS cancer cell line with an IC50 value of 7.6 mu M. (C) 2016 Phytochemical Society of Europe. Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码:192 / 196
页数:5
相关论文
共 17 条
[1]   Sesquiterpene lactones from the aerial parts of Xanthium sibiricum and their cytotoxic effects on human cancer cell lines [J].
Bui, Van-Binh ;
Liu, Shu-Ting ;
Zhu, Jing-Jing ;
Xiong, Juan ;
Zhao, Yun ;
Yang, Guo-Xun ;
Xia, Gang ;
Hu, Jin-Feng .
PHYTOCHEMISTRY LETTERS, 2012, 5 (03) :685-689
[2]   Photoinduced functionalization of the C-20 methyl group of the nor-diterpene atractyligenin [J].
Buscemi, S ;
Rosselli, S ;
Bruno, M ;
Vivona, N ;
Piozzi, F .
TETRAHEDRON LETTERS, 2001, 42 (47) :8289-8291
[3]   Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats [J].
Favier, LS ;
María, AOM ;
Wendel, GH ;
Borkowski, EJ ;
Giordano, OS ;
Pelzer, L ;
Tonn, CE .
JOURNAL OF ETHNOPHARMACOLOGY, 2005, 100 (03) :260-267
[4]   A new ent-kaurane diterpenoid from Isodon phyllostachys [J].
Hou, AJ ;
Yang, H ;
Jiang, B ;
Zhao, QS ;
Lin, ZW ;
Sun, HD .
FITOTERAPIA, 2000, 71 (04) :417-419
[5]   Four New Glycosides from the Fruit of Xanthium sibiricum Patr. [J].
Jiang, Hai ;
Yang, Liu ;
Liu, Chang ;
Hou, Hui ;
Wang, Qiuhong ;
Wang, Zhibin ;
Yang, Bingyou ;
Kuang, Haixue .
MOLECULES, 2013, 18 (10) :12464-12473
[6]   (-)-Xanthienopyran, a new inhibitor of superoxide anion generation by activated neutrophils, and further constituents of the seeds of Xanthium strumarium [J].
Lee, Chia-Lin ;
Huang, Po-Ching ;
Hsieh, Pei-Wen ;
Hwang, Tsong-Long ;
Hou, Yu-Yi ;
Chang, Fang-Rong ;
Wu, Yang-Chang .
PLANTA MEDICA, 2008, 74 (10) :1276-1279
[7]   2 TOXIC KAURENE GLYCOSIDES FROM THE BURRS OF XANTHIUM-PUNGENS [J].
MACLEOD, JK ;
MOELLER, PDR ;
FRANKE, FP .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (02) :451-455
[8]   Sulfated triterpene derivatives from Fagonia arabica [J].
Perrone, Angela ;
Masullo, Milena ;
Bassarello, Carla ;
Hamed, Arafa I. ;
Belisario, Maria Antonietta ;
Pizza, Cosimo ;
Piacente, Sonia .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (04) :584-588
[9]  
Pharmacopeia Committee of P.R. China, 2010, PHARM PEOPL REP CHIN, P1103
[10]   Two new hydroxylated ent-kauranoic acids from Pteris semipinnata [J].
Qiu, Maosong ;
Yang, Bao ;
Cao, Di ;
Zhu, Jinping ;
Jin, Jing ;
Chen, Yunyun ;
Zhou, Lian ;
Luo, Xia ;
Zhao, Zhongxiang .
PHYTOCHEMISTRY LETTERS, 2016, 16 :156-162