Natural products chemistry and taxonomy of the marine cyanobacterium Blennothrix cantharidosmum.

Natural products chemistry and taxonomy of the marine cyanobacterium Blennothrix cantharidosmum.
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DOI:
10.1021/np800088a
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发表时间:
2008-09
影响因子:
5.1
通讯作者:
Gerwick, William H.
Gerwick, William H.
中科院分区:
生物学2区
文献类型:
--
作者:
Clark, Benjamin R.;Engene, Niclas;Teasdale, Margaret E.;Rowley, David C.;Matainaho, Teatulohi;Valeriote, Frederick A.;Gerwick, William H.

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对巴布亚新几内亚野外采集的海洋蓝藻斑点蓝藻的细胞毒性成分进行了研究。生物测定分离将细胞毒性成分定义为已知的化合物lyngbyastatins 1和3。然而,还分离出了6个新的酰基脯氨酸衍生物,肿瘤酸D-I,以及已知的肿瘤酸A。它们的平面结构由核磁共振和MS数据确定,立体结构由一系列手性色谱、降解序列和合成方法确定。新化合物在一系列测试中进行了测试,但仅显示出适度的抗疟疾和抑制群体感应活性。然而,这些是该属首次报道的天然产物,这激发了对产生的有机体进行详细的形态和基于16S rDNA的系统发育分析。
A Papua New Guinea field collection of the marine cyanobacterium Blennothrix cantharidosmum was investigated for its cytotoxic constituents. Bioassay-guided isolation defined the cytotoxic components as the known compounds lyngbyastatins 1 and 3. However, six new acyl proline derivatives, tumonoic acids D-I, plus the known tumonoic acid A, were also isolated. Their planar structures were defined from NMR and MS data while their stereostructures followed from a series of chiral chromatographies, degradation sequences and synthetic approaches. The new compounds were tested in an array of assays, but showed only modest antimalarial and inhibition of quorum sensing activities. Nevertheless, these are the first natural products to be reported from this genus, and this inspired a detailed morphologic and 16S rDNA-based phylogenetic analysis of the producing organism.
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