Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences and the Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , People's Republic of China.
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography , University of California San Diego , La Jolla , California 92093 , United States.
J Org Chem. 2018 Mar 16;83(6):3034-3046. doi: 10.1021/acs.joc.8b00028. Epub 2018 Mar 8.
Cancer cell cytotoxicity was used to guide the isolation of nine new swinholide-related compounds, named samholides A-I (1-9), from an American Samoan marine cyanobacterium cf. Phormidium sp. Their structures were determined by extensive analysis of 1D and 2D NMR spectroscopic data. The new compounds share an unusual 20-demethyl 44-membered lactone ring composed of two monomers, and they demonstrate structural diversity arising from geometric isomerization of double bonds, sugar units with unique glyceryl moieties and varied methylation patterns. All of the new samholides were potently active against the H-460 human lung cancer cell line with IC values ranging from 170 to 910 nM. The isolation of these new swinholide-related compounds from a marine cyanobacterium reinvigorates questions concerning the evolution and biosynthetic origin of these natural products.
采用癌细胞细胞毒性来指导从一种美属萨摩亚海洋蓝藻 cf. 藻属中分离出 9 种新型 swinholide 相关化合物，命名为 samholides A-I（1-9）。通过对 1D 和 2D NMR 波谱数据的广泛分析确定了它们的结构。这些新化合物具有不寻常的 20-去甲基 44 元内酯环，由两个单体组成，它们展示了由于双键的几何异构化、具有独特甘油基部分的糖单元和不同的甲基化模式而产生的结构多样性。所有这些新的 samholides 对 H-460 人肺癌细胞系均具有很强的活性，IC 值范围为 170 至 910 nM。从海洋蓝藻中分离出这些新型 swinholide 相关化合物，再次引发了关于这些天然产物的进化和生物合成起源的问题。
