2,3-Seco-2,3-dioxo-lyngbyatoxin A from a Red Sea strain of the marine cyanobacterium Moorea producens
2,3-Seco-2,3-dioxo-lyngbyatoxin A from a Red Sea strain of the marine cyanobacterium Moorea producens
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DOI：
10.1080/14786419.2014.982647
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发表时间：
2015-04-18
影响因子：
2.2
通讯作者：
Mooberry, Susan L.
中科院分区：
文献类型：
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作者：
Youssef, Diaa T. A.;Shaala, Lamiaa A.;Mooberry, Susan L.
对蓝细菌Moorea producens的红海菌株的有机提取物进行化学研究，得到了2，3-seco-2，3-dioxo-lyngbyatoxin A（1）。另外还分离到5个已知化合物，包括lyngbyatoxin A（2），majusculamides A和B（3和4），apatriasiatoxin（5）和debrominasiatoxin（6）。通过HR-FAB-MS、1D和2D NMR分析确定了它们的结构。评估了这些化合物对HeLa癌细胞的抗增殖活性。Lyngbyatoxin A（2）显示出强活性，IC 50为9.2nM，而5和6显示出中等活性，IC 50值分别为13.3和3.03 μ M。相反，化合物1、3和4是无活性的，IC 50值大于50 μ M。2，3-开环-2，3-二氧代-林贝毒素A（1）没有细胞毒性，这表明林贝毒素（2）中的吲哚部分对其细胞毒性是必不可少的，并表明2的解毒可能是通过吲哚部分的生物氧化产生1来进行的。
Chemical investigation of the organic extract of a Red Sea strain of the cyanobacterium Moorea producens has afforded 2,3-seco-2,3-dioxo-lyngbyatoxin A (1). Five known compounds including lyngbyatoxin A (2), majusculamides A and B (3 and 4), aplysiatoxin (5) and debromoaplysiatoxin (6) were also isolated. Their structures were elucidated by using HR-FAB-MS, 1D and 2D NMR analyses. The compounds were evaluated for antiproliferative activity against HeLa cancer cells. Lyngbyatoxin A (2) showed potent activity, with an IC50 of 9.2nM, while 5 and 6 displayed modest activity with IC50 values of 13.3 and 3.03 mu M, respectively. In contrast, compounds 1, 3 and 4 were inactive, with IC50 values greater than 50 mu M. The lack of cytotoxicity for 2,3-seco-2,3-dioxo-lyngbyatoxin A (1) demonstrates that the indole moiety in lyngbyatoxin (2) is essential for its cytotoxicity, and suggests that detoxification of 2 may be carried out by biological oxidation of the indole moiety to yield 1.