Structure, synthesis, and biological activity of a C-20 bisacetylenic alcohol from a marine sponge Callyspongia sp

  • J Nat Prod. 2013 Jul 26;76(7):1337-42. doi: 10.1021/np400297p.
Takayuki Shirouzu  1 ,  Kousuke Watari ,  Mayumi Ono ,  Keiichi Koizumi ,  Ikuo Saiki ,  Chiaki Tanaka ,  Rob W M van Soest ,  Tomofumi Miyamoto
Affiliations
  • 1. Department of Natural Products Chemistry, Graduate School of Pharmaceutical Sciences, Kyushu University, Maidashi 3-1-1, Higashi-ku, Fukuoka 812-8582, Japan.
PMID: 23855338 DOI: 10.1021/np400297p
Abstract

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.