Structure, Synthesis, and Biological Activity of a C-20 Bisacetylenic Alcohol from a Marine Sponge Callyspongia sp.

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• 作者：Takayuki Shirouzu ; Kousuke Watari ; Mayumi Ono ; Keiichi Koizumi ; Ikuo Saiki ; Chiaki Tanaka ; Rob W. M. van Soest ; Tomofumi Miyamoto
• 刊名：Journal of Natural Products
• 出版年：2013
• 出版时间：July 26, 2013
• 年：2013
• 卷：76
• 期：7
• 页码：1337-1342
• 全文大小：322K
• 年卷期：v.76,no.7(July 26, 2013)
• ISSN：1520-6025

文摘

An optically inactive C-20 bisacetylenic alcohol, (4E,16E)-icosa-4,16-diene-1,19-diyne-3,18-diol, was isolated from a marine sponge Callyspongia sp. as a result of screening of antilymphangiogenic agents from marine invertebrates. An optical resolution using chiral-phase HPLC gave each enantiomer, (鈭?-1 and (+)-2. Because the natural and synthetic enantiomers 1 and 2 showed different biological properties, we investigated the structure鈥揳ctivity relationships of bisacetylenic alcohols using 11 synthetic derivatives, and it is clarified that the essential structural unit for antiproliferative activity is the 鈥?-yn-3-ol鈥?on both termini and that there is a minimum chain length that connects the 鈥?-yn-3-ol鈥?moieties.