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

Takayuki Shirouzu, Kosuke Watari, Mayumi Ono, Keiichi Koizumi, Ikuo Saiki, Chiaki Tanaka, Rob W.M. Van Soest, Tomofumi Miyamoto

Research output: Contribution to journalArticle

14 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1337-1342
Number of pages6
JournalJournal of Natural Products
Volume76
Issue number7
DOIs
Publication statusPublished - Jul 26 2013

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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