Urda Carlos, Fernández Rogelio, Rodríguez Jaime, Pérez Marta, Jiménez Carlos, Cuevas Carmen
Medicinal Chemistry Department, PharmaMar S. A., Polígono Industrial La Mina Norte, Avenida de los Reyes 1, 28770 Madrid, Spain.
Department of Chemistry, Faculty of Sciences and Center for Advanced Scientific Research (CICA), University of A Coruña, 15071 A Coruña, Spain.
Mar Drugs. 2017 Jul 1;15(7):209. doi: 10.3390/md15070209.
Two novel oxazole-thiazole containing cyclic hexapeptides, bistratamides M () and N () have been isolated from the marine ascidian collected in Raja Ampat (Papua Bar, Indonesia). The planar structure of and was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configuration of the amino acid residues in and was determined by the application of the Marfey's and advanced Marfey's methods after ozonolysis followed by acid-catalyzed hydrolysis. The interaction between zinc (II) and the naturally known bistratamide K (), a cyclic hexapeptide isolated from a different specimen of , was monitored by ¹H and C NMR. The results obtained are consistent with the proposal that these peptides are biosynthesized for binding to metal ions. Compounds and display moderate cytotoxicity against four human tumor cell lines with GI values in the micromolar range.
从印度尼西亚巴布亚省拉贾安帕特收集的海洋海鞘中分离出了两种新型含恶唑-噻唑的环状六肽，双层酰胺M（）和N（）。通过广泛的一维和二维核磁共振光谱以及质谱确定了和的平面结构。在臭氧分解后进行酸催化水解，然后应用马尔菲法和先进的马尔菲法确定了和中氨基酸残基的绝对构型。通过¹H和C NMR监测锌（II）与天然存在的双层酰胺K（）之间的相互作用，双层酰胺K是从的不同标本中分离出的一种环状六肽。所得结果与这些肽是为结合金属离子而生物合成的这一推测一致。化合物和对四种人类肿瘤细胞系显示出中等细胞毒性，GI值在微摩尔范围内。
