Isolation and structure assignments of rostratins A-D, cytotoxic disulfides produced by the marine-derived fungus Exserohilum rostratum
Isolation and structure assignments of rostratins A-D, cytotoxic disulfides produced by the marine-derived fungus Exserohilum rostratum
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DOI：
10.1021/np049920b
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发表时间：
2004-08-01
影响因子：
5.1
通讯作者：
Fenical, W
中科院分区：
文献类型：
--
作者：
Tan, RX;Jensen, PR;Fenical, W
从海洋真菌Exserohelum rostratum(Drechsler)的整个发酵液中分离到4个新的细胞毒性二硫化物，Rostratins A-D(1-4)，该真菌菌株与海洋蓝藻垫子有关。这些环状二肽的结构是通过化学降解和各种二维核磁共振技术确定的。用改进的Mosher方法确定了罗非菌素的绝对构型。在多羟基化合物1和硫醇4的情况下，通过调节反应温度实现了区域选择性酰化反应，同时通过H-1核磁共振监测反应进程。Rostratins A、B、C和D对人结肠癌(HCT-116)具有体外细胞毒作用，其IC50值分别为8.5、1.9、0.76和16.5mug/mL。
Four new cytotoxic disulfides, rostratins A-D (1-4), were isolated from the whole broth of the marine-derived fungus Exserohilum rostratum (Drechsler), a fungal strain found associated with a marine cyanobacterial mat. The structures of these cyclic dipeptides were established through chemical degradation and a variety of two-dimensional NMR techniques. The absolute configurations of the rostratins were determined by the modified Mosher method. In the case of the polyhydroxylated compound 1 and the mercaptol 4, regioselective acylation was achieved by modulating the reaction temperature while monitoring the progress of the reaction by H-1 NMR. Rostratins A, B, C, and D showed in vitro cytotoxicity against human colon carcinoma (HCT-116) with IC50 values of 8.5, 1.9, 0.76, and 16.5 mug/mL, respectively.