Cytotoxic Bromoindole Derivatives and Terpenes from the Philippine Marine Sponge Smenospongia sp.
Cytotoxic Bromoindole Derivatives and Terpenes from the Philippine Marine Sponge Smenospongia sp.
复制标题
DOI：
10.1515/znc-2002-9-1027
复制
发表时间：
2002-09
期刊：
影响因子：
--
通讯作者：
D. Taşdemir;T. Bugni;G. C. Mangalindan;G. Concepcion;M. K. Harper;C. Ireland
中科院分区：
文献类型：
--
作者：
D. Taşdemir;T. Bugni;G. C. Mangalindan;G. Concepcion;M. K. Harper;C. Ireland
本文对菲律宾海绵Smenospongia sp.进行了详细的化学分析。本研究产生了4种新的代谢产物，5-溴-1-色氨酸（1）、5-溴阿滨（2）、5，6-二溴阿滨（3）和5-溴吲哚-3-乙酸（4）。另外还分离出吡咯亚氨基醌生物碱makaluvamine O（5）、5，6-二溴色胺（6）、aureol（7）和furospinulosin 1（8）。虽然1和4以前已经合成，这是第一次报告的分离，这些化合物从天然来源。首次从该属植物中分离得到呋喃甾萜类化合物furosinulosin 1（8）。所有化合物的结构均经紫外光谱、红外光谱、一维和二维核磁共振谱、质谱、[α]核磁共振谱确证。在一组等基因HCT-116人结肠肿瘤细胞系中评价了1−8的细胞毒性潜力。
A detailed chemical analysis of a Philippine marine sponge Smenospongia sp. has been performed. This study yielded four new metabolites, 5-bromo-l-tryptophan (1), 5-bromoabrine (2), 5,6-dibromoabrine (3) and 5-bromoindole-3-acetic acid (4). The pyrroloiminoquinone alkaloid, makaluvamine O (5) as well as 5,6-dibromotryptamine (6), aureol (7) and furospinulosin 1 (8) were also isolated. Although 1 and 4 have been synthesized previously, this is the first report on the isolation of these compounds from a natural source. The furanosesterterpene furospinulosin 1 (8) was obtained for the first time from the genus Smenospongia. The structures of all compounds were established by spectroscopic methods (UV, IR, 1D and 2D NMR, MS, [α]ᴅ). The cytotoxic potential of 1−8 was evaluated in a panel of isogenic HCT-116 human colon tumor cell lines.