Cytotoxic triterpenoids from Lysimachia parvifolia

被引:9
作者
He, Zhengchun [1 ,2 ]
Liang, Fengjie [1 ]
Lu, Jing [1 ]
Pan, Yuanjiang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
[2] Dali Coll, Dept Pharm, Dali 671000, Peoples R China
关键词
Triterpenoid; Cytotoxic activity; Lysimachia parvifolia; ANAGALLIS-ARVENSIS; SAPONINS; CAPILLIPES; GLYCOSIDES;
D O I
10.1016/j.ejmech.2013.06.043
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Five new oleanane-type triterpenoids, including two aglycones, 13 beta-28-epoxy-3 beta,22 alpha,23-trihydroxyolean-16-one (1) and 13 beta-28-epoxy-22 alpha,23-dihydroxyolean-3,16-dione (2), and three glycosides, anagalligenone-3-O-alpha-L-arabinopyranoside (3), anagalligenone-3-O-[beta-D-glucopyranosyl(1 -> 4)-alpha-L-arabinopyranoside] (4) and anagalligenone-3-O-[beta-D-xylopyranosyl(1 -> 2)-beta-D-glucopyranosyl(1 -> 4)-alpha-L-arabinopyranoside] (5), were isolated from the aerial parts of Lysimachia parvifolia, together with three known oleanane-type triterpenoid glycosides (6-8). The structures of the new compounds were subsequently elucidated by spectroscopic analysis and their cytotoxicities evaluated against six human cancer cell lines. Compounds 5-8 exhibited significant cytotoxicities against all the cell lines tested, with IC50 values lower than 10 mu M. The possible mechanism of action of compound 6 was also studied. (C) 2013 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:390 / 397
页数:8
相关论文
共 18 条
[1]   Pharmacological activities of natural triterpenoids and their therapeutic implications [J].
Dzubak, Petr ;
Hajduch, Marian ;
Vydra, David ;
Hustova, Alica ;
Kvasnica, Miroslav ;
Biedermann, David ;
Markova, Lenka ;
Urban, Milan ;
Sarek, Jan .
NATURAL PRODUCT REPORTS, 2006, 23 (03) :394-411
[2]   Efficient synthesis of trisaccharide saponins and their tumor cell killing effects through oncotic necrosis [J].
Gao, Jian ;
Li, Xia ;
Gu, Guofeng ;
Sun, Bin ;
Cui, Min ;
Ji, Mei ;
Lou, Hong-Xiang .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (02) :622-627
[3]  
HARA S, 1987, CHEM PHARM BULL, V35, P501
[4]   Isolation and structural characterization of a novel galactomannan from Eremurus anisopterus (Ker. et Kir) Regel roots [J].
Hu, Changfeng ;
Kong, Qingjun ;
Yang, Deyu ;
Pan, Yuanjiang .
CARBOHYDRATE POLYMERS, 2011, 84 (01) :402-406
[5]   Two New Triterpenoids from Lysimachia heterogenea Klatt and Evaluation of Their Cytotoxicity [J].
Huang, Xin-An ;
Shen, Xiao-Ling ;
Hu, Ying-Jie ;
Liu, Ya-Ming ;
Liu, Kang-Lun ;
Zhang, Feng-Xue ;
Zhou, Xin-Xin .
MOLECULES, 2011, 16 (09) :8076-8082
[6]  
Huang XinAn Huang XinAn, 2007, Journal of Tropical and Subtropical Botany, V15, P175
[7]   Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents [J].
Kuo, Reen-Yen ;
Qian, Keduo ;
Morris-Natschke, Susan L. ;
Lee, Kuo-Hsiung .
NATURAL PRODUCT REPORTS, 2009, 26 (10) :1321-1344
[8]   Isolation and characterization of two new saponins from Lysimachia capillipes [J].
Liang, Bo ;
Zhang, Lin ;
Tian, Jingkui ;
Xu, Lizhen ;
Yang, Shilin .
CARBOHYDRATE RESEARCH, 2006, 341 (14) :2444-2448
[9]   STRUCTURE ELUCIDATION OF 4 NEW TRITERPENOID OLIGOGLYCOSIDES FROM ANAGALLIS-ARVENSIS [J].
MAHATO, SB ;
SAHU, NP ;
ROY, SK ;
SEN, S .
TETRAHEDRON, 1991, 47 (28) :5215-5230
[10]   C-13 NMR-SPECTRA OF PENTACYCLIC TRITERPENOIDS - A COMPILATION AND SOME SALIENT FEATURES [J].
MAHATO, SB ;
KUNDU, AP .
PHYTOCHEMISTRY, 1994, 37 (06) :1517-1575