Sulfoureido lipopeptides from the marine sponge Discodermia kiiensis
Sulfoureido lipopeptides from the marine sponge Discodermia kiiensis
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来自海洋海绵 Discodermia kiiensis 的磺酰脂肽
DOI：
10.1021/acs.jnatprod.6b00586
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发表时间：
2016
期刊：
影响因子：
5.1
通讯作者：
I.
中科院分区：
文献类型：
--
作者：
Tan;K. C.;Wakimoto;T.;Abe;I.
用海绵盘状软盘的正丁醇部分进行凝胶过滤层析，分离得到新的磺脲基脂肽A-C(1-3)。通过广泛的核磁共振分析和高分辨质谱学，1-3的结构被确定为在瓜氨酸残基上具有前所未有的N-磺酰基，这是结构上相关的脂二酰胺A-C(4-6)中所没有的特征，这些脂二胺来自同一海绵的乙醚部分。此外，通过比较水解物和相应的正品脂二酰胺的高效液相保留时间，确定了1-3的绝对构型。有趣的是，与未结合的母体化合物相比，磺胺类药物A对小鼠白血病(P388)细胞的细胞毒性增加了2.3倍。
NewN-sulfoureidylated lipopeptides, sulfolipodiscamides A–C (1–3), were isolated by gel filtration chromatography of then-butanol fraction of the marine spongeDiscodermia kiiensis. By extensive NMR analyses and high-resolution mass spectrometry, the structures of1–3were elucidated as having an unprecedentedN-sulfoureidyl group on thed-citrulline residue, a distinct feature that was not found in the structurally related lipodiscamides A–C (4–6), derived from the ether fraction of the same sponge. Furthermore, the absolute configurations of1–3were confirmed by comparisons of the HPLC retention times of the hydrolytic products and the corresponding authentic lipodiscamides. Interestingly, sulfolipodiscamide A displayed a 2.3-fold increase in cytotoxicity against murine leukemia (P388) cells, compared to the unconjugated parent compound.