（-）-Duryne 及其同系物，来自海洋海绵 Petrosia sp. 的细胞毒性乙炔

(-)-Duryne and its homologues, cytotoxic acetylenes from a marine Sponge Petrosia sp.

机构信息

Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, 113-8657, Japan.

出版信息

J Nat Prod. 2011 May 27;74(5):1262-7. doi: 10.1021/np200271n. Epub 2011 May 2.

DOI:10.1021/np200271n

PMID:21534590

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.

摘要

从海洋海绵 Petrosia sp. 中分离得到了 6 个线性炔烃，(-)-duryne (1) 和 (-)-durynes B-F (2-6)。通过 NMR 和串联 FABMS 分析阐明了它们的结构。通过臭氧裂解实验确定了双键的位置，并通过改良的 Mosher 法确定了绝对构型。化合物 1 被发现是先前报道的海绵代谢产物 duryne 的对映异构体。化合物 1-6 对 HeLa 细胞具有细胞毒性，IC50 值在 0.08 和 0.50 μM 之间。