Psammaplins from the sponge Pseudoceratina purpurea:: Inhibition of both histone deacetylase and DNA methyltransferase
Psammaplins from the sponge Pseudoceratina purpurea:: Inhibition of both histone deacetylase and DNA methyltransferase
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DOI：
10.1021/jo034248t
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发表时间：
2003-05-16
影响因子：
3.6
通讯作者：
Crews, P
中科院分区：
文献类型：
--
作者：
Piña, IC;Gautschi, JT;Crews, P
从海绵Pseudoceratina purpurea中分离出四种新的二硫代溴酪氨酸衍生物，psammaplin E（9）、F（10）、G（11）和H（12），以及两种新的溴酪氨酸衍生物，psammaplin 1（13）和J（14），沿着已知的psammaplin A（4）、B（6）、C（7）和D（8）和bisaprasin（5）。通过光谱分析确定了psammaplin E（9）和F（10）的结构，它们各自含有在海洋生物中很少发现的草酰基。化合物4、5和10是有效的组蛋白脱乙酰酶抑制剂，并且还显示出轻度的细胞毒性。此外，化合物4、5和11是有效的DNA甲基转移酶抑制剂。以前提出的psammaplin类的生物遗传途径也被重新审视。
Four novel bisulfide bromotyrosine derivatives, psammaplins E (9), F (10), G (11), and H (12), and two new bromotyrosine derivatives, psammaplins 1 (13) and J (14), were isolated from the sponge Pseudoceratina purpurea, along with known psammaplins A (4), B (6), C (7), and D (8) and bisaprasin (5). The structures of psammaplins E (9) and F (10), which each contain an oxalyl group rarely found in marine organisms, were determined by spectroscopic analysis. Compounds 4, 5, and 10 are potent histone deacetylase inhibitors and also show mild cytotoxicity. Furthermore, compounds 4, 5, and 11 are potent DNA methyltransferase inhibitors. The biogenetic pathway previously proposed for the psammaplins class is also revisited.