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

研究成果: ジャーナルへの寄稿記事

14 引用 (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.

元の言語英語
ページ(範囲)1337-1342
ページ数6
ジャーナルJournal of Natural Products
76
発行部数7
DOI
出版物ステータス出版済み - 7 26 2013

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Callyspongia
Enantiomers
Porifera
Bioactivity
Alcohols
Invertebrates
Structure-Activity Relationship
Chain length
Screening
High Pressure Liquid Chromatography
Derivatives

All Science Journal Classification (ASJC) codes

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

これを引用

Structure, synthesis, and biological activity of a C-20 bisacetylenic alcohol from a marine sponge Callyspongia sp. / Shirouzu, Takayuki; Watari, Kosuke; Ono, Mayumi; Koizumi, Keiichi; Saiki, Ikuo; Tanaka, Chiaki; Van Soest, Rob W.M.; Miyamoto, Tomofumi.

:: Journal of Natural Products, 巻 76, 番号 7, 26.07.2013, p. 1337-1342.

研究成果: ジャーナルへの寄稿記事

Shirouzu, Takayuki ; Watari, Kosuke ; Ono, Mayumi ; Koizumi, Keiichi ; Saiki, Ikuo ; Tanaka, Chiaki ; Van Soest, Rob W.M. ; Miyamoto, Tomofumi. / Structure, synthesis, and biological activity of a C-20 bisacetylenic alcohol from a marine sponge Callyspongia sp. :: Journal of Natural Products. 2013 ; 巻 76, 番号 7. pp. 1337-1342.
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AU - Koizumi, Keiichi

AU - Saiki, Ikuo

AU - Tanaka, Chiaki

AU - Van Soest, Rob W.M.

AU - Miyamoto, Tomofumi

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