Structure, Synthesis, and Biological Activity of a C-20 Bisacetylenic Alcohol from a Marine Sponge Callyspongia sp.
Structure, Synthesis, and Biological Activity of a C-20 Bisacetylenic Alcohol from a Marine Sponge Callyspongia sp.
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DOI：
10.1021/np400297p
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发表时间：
2013-07-01
影响因子：
5.1
通讯作者：
Miyamoto, Tomofumi
中科院分区：
文献类型：
--
作者：
Shirouzu, Takayuki;Watari, Kousuke;Miyamoto, Tomofumi
从海洋无脊椎动物中筛选出抗淋巴管生成剂，从海绵Callypongia sp.中分离出一种光学惰性的C-20双炔醇，即（4 E，16 E）-二十碳-4，16-二烯-1，19-二炔-3，18-二醇。使用手性相HPLC进行光学拆分，得到各对映异构体（-）-1和（+）-2。由于天然和合成的对映体1和2显示出不同的生物学性质，我们研究了双炔醇使用11个合成衍生物的结构活性关系，并澄清了抗增殖活性的基本结构单元是两端的“1-炔-3-醇”，并且存在连接“1-炔-3-醇”部分的最小链长。
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, (-)-1 and (+)-2. Because the natural and synthetic enantiomers 1 and 2 showed different biological properties, we investigated the structure activity relationships of bisacetylenic alcohols using 11 synthetic derivatives, and it is clarified that the essential structural unit for antiproliferative activity is the "1-yn-3-ol" on both termini and that there is a minimum chain length that connects the "1-yn-3-ol" moieties.