1446512-33-9Relevant articles and documents
Structure, synthesis, and biological activity of a C-20 bisacetylenic alcohol from a marine sponge Callyspongia sp.
Shirouzu, Takayuki,Watari, Kousuke,Ono, Mayumi,Koizumi, Keiichi,Saiki, Ikuo,Tanaka, Chiaki,Van Soest, Rob W. M.,Miyamoto, Tomofumi
, p. 1337 - 1342 (2013/08/23)
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.