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

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

研究成果: ジャーナルへの寄稿学術誌査読

19 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)1337-1342
ページ数6
ジャーナルJournal of Natural Products
76
7
DOI
出版ステータス出版済み - 7月 26 2013

!!!All Science Journal Classification (ASJC) codes

  • 分析化学
  • 分子医療
  • 薬理学
  • 薬科学
  • 創薬
  • 補完代替医療
  • 有機化学

フィンガープリント

「Structure, synthesis, and biological activity of a C-20 bisacetylenic alcohol from a marine sponge Callyspongia sp.」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル