Novel isomarabarican triterpenes, exhibiting selective anti-proliferative activity against vascular endothelial cells, from marine sponge Rhabdastrella globostellata

被引:32
作者
Aoki, Shunji
Sanagawa, Mami
Watanabe, Yasuo
Setiawan, Andi
Arai, Masayoshi
Kobayashi, Motomasa
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
[2] Lampung Univ, Fac Sci, Dept Chem, Bandar Lampung 35145, Indonesia
关键词
globostellatic acid X methyl esters; marine sponge; anti-angiogenic effect; HUVECs; tubular formation; migration;
D O I
10.1016/j.bmc.2007.04.070
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
Four novel globostellatic acid X methyl esters (1-4) having isomarabarican-type triterpenoidal skeleton and three related new compounds (5-7) were isolated from the marine sponge Rhabdastrella globostellata, as selective anti-proliferative agents against human umbilical vein endothelial cells (HUVECs). Those chemical structures were elucidated by the detailed 2D NMR analysis. Two globostellatic acid X methyl esters (3 and 4) having 13E-geometry were found to inhibit proliferation of HUVECs, 80- to 250-fold selectively in comparison with several other cell lines. 13E,17E-Globostellatic acid X methyl ester (4) also inhibited bFGF-induced tubular formation and VEGF-induced migration of HUVECs. Moreover, 4 induced apoptosis of HUVECs, whereas it exhibited no effect on VEGF-induced phosphorylation of ERK1/2 in HUVECs. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4818 / 4828
页数:11
相关论文
共 13 条
[1]   Bastadin 6, a spongean brominated tyrosine derivative, inhibits tumor angiogenesis by inducing selective apoptosis to endothelial cells [J].
Aoki, Shunji ;
Cho, Seok-hwan ;
Ono, Mayumi ;
Kuwano, Takashi ;
Nakao, Shintaro ;
Kuwano, Michihiko ;
Nakagawa, Shinsaku ;
Gao, Jian-Qing ;
Mayumi, Tadanori ;
Shibuya, Masabumi ;
Kobayashi, Motomasa .
ANTI-CANCER DRUGS, 2006, 17 (03) :269-278
[2]   ISOLATION OF A TUMOR FACTOR RESPONSIBLE FOR ANGIOGENESIS [J].
FOLKMAN, J ;
MERLER, E ;
ABERNATHY, C ;
WILLIAMS, G .
JOURNAL OF EXPERIMENTAL MEDICINE, 1971, 133 (02) :275-+
[3]  
FOLKMAN J, 1992, J BIOL CHEM, V267, P10931
[4]   ANGIOGENESIS IN CANCER, VASCULAR, RHEUMATOID AND OTHER DISEASE [J].
FOLKMAN, J .
NATURE MEDICINE, 1995, 1 (01) :27-31
[5]   Differential αv integrin-mediated Ras-ERK signaling during two pathways of angiogenesis [J].
Hood, JD ;
Frausto, R ;
Kiosses, WB ;
Schwartz, MA ;
Cheresh, DA .
JOURNAL OF CELL BIOLOGY, 2003, 162 (05) :933-943
[6]   Jaspiferals A-G, new cytotoxic isomalabaricane-type nortriterpenoids from Okinawan marine sponge Jaspis stellifera [J].
Kobayashi, J ;
Yuasa, K ;
Kobayashi, T ;
Sasaki, T ;
Tsuda, M .
TETRAHEDRON, 1996, 52 (16) :5745-5750
[7]  
KONDRACKI MLB, 2000, TETRAHEDRON LETT, V41, P3087
[8]   Cytotoxic triterpenes from a marine sponge, Stelletta sp [J].
McCormick, JL ;
McKee, TC ;
Cardellina, JH ;
Leid, M ;
Boyd, MR .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (11) :1047-1050
[9]   Rhabdastrellic acid-A, a novel triterpenoid from the marine sponge Rhabdastrella globostellata [J].
Rao, ZG ;
Deng, SZ ;
Wu, HM ;
Jiang, SK .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (11) :1163-1164
[10]   Globostellatic acids A-D, new cytotoxic isomalabaricane triterpenes from the marine sponge Stelletta globostellata [J].
Ryu, G ;
Matsunaga, S ;
Fusetani, N .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (05) :512-514