Structure and cytotoxicity of new metabolites from the sponge Mycale cecilia

Structure and cytotoxicity of new metabolites from the sponge Mycale cecilia
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DOI:
10.1016/j.tet.2004.01.056
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发表时间:
2004-03-08
期刊:
影响因子:
2.1
通讯作者:
Carballo, JL
Carballo, JL
中科院分区:
化学3区
文献类型:
--
作者:
Ortega, MJ;Zubía, E;Carballo, JL

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海绵Mycale cecilia的化学研究导致了14个新的含吡咯代谢产物的分离。Mycalazals 3-13是在C-5处具有不同长度和/或不饱和度数目的烃侧链的吡咯-2-甲醛。Mycalenitriles 1-3是5-氰基烷基吡咯-2-甲醛。新化合物的结构主要通过NMR和MS光谱分析确定。通过相应的双(甲硫基)衍生物的MS分析确定了mycalazal-4、-8和-11中双键的位置。mycalazal已经显示出作为几种肿瘤细胞系,特别是LNcaP细胞系的生长抑制剂的活性,mycalazal-8是最具活性的代谢物。(C)2004 Elsevier Ltd.保留所有权利。
The chemical study of the sponge Mycale cecilia has led to the isolation of 14 new pyrrole-containing metabolites. Mycalazals 3-13 are pyrrole-2-carbaldehydes possessing at C-5 hydrocarbon side chains of different length and/or number of unsaturations. Mycalenitriles 1-3 are 5-cyanoalkylpyrrole-2-carbaldehydes. The structures of the new compounds were established mainly by NMR and MS spectroscopic analysis. The location of the double bond in mycalazal-4, -8, and -11 was determined by MS analysis of the corresponding bis(methylthio) derivatives. Mycalazals have shown activity as growth inhibitors of several tumor cell lines, in particular the LNcaP cell line, being mycalazal-8 the most active metabolite. (C) 2004 Elsevier Ltd. All rights reserved.