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.
authors.affiliation: Department of Natural Products Chemistry, Graduate School of Pharmaceutical Sciences, Kyushu University, Maidashi 3-1-1, Higashi-ku, Fukuoka 812-8582, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Shirouzu
authors.forename: Kousuke
authors.initials: K
authors.lastname: Watari
authors.forename: Mayumi
authors.initials: M
authors.lastname: Ono
authors.forename: Keiichi
authors.initials: K
authors.lastname: Koizumi
authors.forename: Ikuo
authors.initials: I
authors.lastname: Saiki
authors.forename: Chiaki
authors.initials: C
authors.lastname: Tanaka
authors.forename: Rob W M
authors.initials: RW
authors.lastname: van Soest
authors.forename: Tomofumi
authors.initials: T
authors.lastname: Miyamoto
mesh_terms: D000438:Alcohols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D047128:Callyspongia / Q000737:chemistry*; D053280:Diynes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007564:Japan; D008386:Marine Biology; D015394:Molecular Structure; D009792:Oceans and Seas; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C584221:(4E,16E)-icosa-4,16-diene-1,19-diyne-3,18-diol; D000438:Alcohols; D053280:Diynes