TY - JOUR
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.
UR - http://www.scopus.com/inward/record.url?scp=84880880284&partnerID=8YFLogxK
U2 - 10.1021/np400297p
DO - 10.1021/np400297p
M3 - 学術論文
C2 - 23855338
AN - SCOPUS:84880880284
SN - 0163-3864
VL - 76
SP - 1337
EP - 1342
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 7
ER -
