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

doi:10.1021/np400297p

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

Research output: Contribution to journal › Article › peer-review

19 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 language	English
Pages (from-to)	1337-1342
Number of pages	6
Journal	Journal of Natural Products
Volume	76
Issue number	7
DOIs	https://doi.org/10.1021/np400297p
Publication status	Published - 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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10.1021/np400297p

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

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.",

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doi = "10.1021/np400297p",

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T1 - Structure, synthesis, and biological activity of a C-20 bisacetylenic alcohol from a marine sponge Callyspongia sp.

AU - Shirouzu, Takayuki

AU - Watari, Kousuke

AU - Ono, Mayumi

AU - Koizumi, Keiichi

AU - Saiki, Ikuo

AU - Tanaka, Chiaki

AU - Van Soest, Rob W.M.

AU - Miyamoto, Tomofumi

PY - 2013/7/26

Y1 - 2013/7/26

N2 - 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.

AB - 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.

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

Abstract

All Science Journal Classification (ASJC) codes

UN SDGs

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