西沙海绵Phakellia sp.溴代吡咯生物碱类次级代谢产物研究

Studies on secondary metabolites of bromopyrrole alkaloids from a Xisha sponge Phakellia sp.

目的对采自西沙群岛的海绵样品Phakellia sp.进行溴代吡咯生物碱类次级代谢产物的研究。方法利用硅胶柱层析、中压制备型液相色谱和高效液相色谱等现代分离手段对海绵样品浸膏进行分离、纯化,得到单体化合物;综合运用核磁共振波谱、质谱等现代波谱学方法,通过与已知文献报道的数据进行对比,对分离得到的化合物进行结构鉴定。结果从海绵Phakellia sp.中分离鉴定得到10个溴代吡咯生物碱,分别为4-bromo-1H-pyrrole-3-carbamide(1)、4-bromopyrrole-2-carboxylicacid(2)、4,5-dibromo-2-pyrrolicacid(3)、bromopyrrole alkaloid(4)、N-(4,5-二溴-2-吡咯甲酰基)-乙酸甲酯(5)、N-(4-溴-2-吡咯甲酰基)-β-丙氨酸甲酯(6)、N-(4,5-二溴-2-吡咯甲酰基)-β-丙氨酸甲酯(7)、mukanadin B(8)、9-hydroxy derivative of mukanadin B(9)、mukanadin D(10)。结论从西沙海绵Phakellia sp.中分离得到10个已知的溴代吡咯生物碱,其中化合物5、6、7为新天然产物。

Objective To investigate the secondary metabolites of bromopyrrole alkaloids from a sponge Phakellia sp.collected from the Xisha islands.Methods The secondary metabolites were separated and purified by silica gel column chromatography,medium pressure preparative HPLC and semi-HPLC column chromatography,and their structures were determined by NMR,MS and other spectral methods,and comparison with previously reported data.Results Ten bromopyrrole alkaloids were isolated from Phakellia sp.and were identified as 4-bromo-1H-pyrrole-3-carbamide(1),4-bromopyrrole-2-carboxylicacid(2),4,5-dibromo-2-pyrrolic acid(3),bromopyrrole alkaloid(4),N-(4,5-dibromo-2-pyrrole formyl)-methyl acetat(5),N-(4-bromo-2-pyrrole formyl)-β-alanine methyl ester(6),N-(4,5-dibromo-2-pyrrole formyl)-β-alanine methyl este(7),mukanadin B(8),9-hydroxy derivative of mukanadin B(9),mukanadin D(10),respectively.Conclusion Ten known bromopyrrole alkaloids were isolated from Phakellia sp.,and compounds 5,6 and 7 were new natural products.