title: (-)-Duryne and its homologues, cytotoxic acetylenes from a marine Sponge Petrosia sp.
abstract: Six linear acetylenes, (-)-duryne (1) and (-)-durynes B-F (2-6), were isolated from the marine sponge Petrosia sp. Their structures were elucidated by NMR and tandem FABMS analyses. The positions of the olefinic bonds were confirmed by ozonolysis experiments, and the absolute configurations were determined by the modified Mosher's method. Compound 1 was found to be the enantiomer of duryne, a previously reported sponge metabolite. Compounds 1-6 show cytotoxicity against HeLa cells with IC50 values between 0.08 and 0.50 μM.
authors.affiliation: Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, 113-8657, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Hitora
authors.forename: Kentaro
authors.initials: K
authors.lastname: Takada
authors.forename: Shigeru
authors.initials: S
authors.lastname: Okada
authors.forename: Yuji
authors.initials: Y
authors.lastname: Ise
authors.forename: Shigeki
authors.initials: S
authors.lastname: Matsunaga
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D007564:Japan; D008386:Marine Biology; D015394:Molecular Structure; D047130:Petrosia / Q000737:chemistry*; D053279:Polyynes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; C527593:duryne; D053279:Polyynes