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

Four novel isomarabarican triterpenes named globostellatic acid methyl esters and the related compounds were isolated from the marin sponge Rhabdastrella globostellata. Their chemical structures and in vitro antiangiogenic activities were examined. Four novel globostellatic acid X methyl esters ( 1–...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2007-07, Vol.15 (14), p.4818-4828
Main Authors: Aoki, Shunji, Sanagawa, Mami, Watanabe, Yasuo, Setiawan, Andi, Arai, Masayoshi, Kobayashi, Motomasa
Format: Article
Language:English
Subjects:
Animals
Anti-angiogenic effect
Biological and medical sciences
Cell Proliferation - drug effects
Cells, Cultured
Endothelial Cells - cytology
Endothelial Cells - drug effects
Esters - chemistry
Esters - isolation & purification
Esters - pharmacology
General pharmacology
Globostellatic acid X methyl esters
Humans
HUVECs
Isomerism
Magnetic Resonance Spectroscopy
Marine sponge
Medical sciences
Methylation
Migration
Models, Molecular
Molecular Structure
Oceans and Seas
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Porifera - chemistry
Structure-Activity Relationship
Triterpenes - chemistry
Triterpenes - isolation & purification
Triterpenes - pharmacology
Tubular formation
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Summary:Four novel isomarabarican triterpenes named globostellatic acid methyl esters and the related compounds were isolated from the marin sponge Rhabdastrella globostellata. Their chemical structures and in vitro antiangiogenic activities were examined. 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 13 E-geometry were found to inhibit proliferation of HUVECs, 80- to 250-fold selectively in comparison with several other cell lines. 13 E,17 E-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.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2007.04.070