Cytotoxic Glycosylated Fatty Acid Amides from a Stelletta sp. Marine Sponge
Cytotoxic Glycosylated Fatty Acid Amides from a Stelletta sp. Marine Sponge
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来自 Stelletta sp 的细胞毒性糖基化脂肪酸酰胺。
DOI：
10.1021/acs.jnatprod.5b00795
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发表时间：
2015
影响因子：
5.1
通讯作者：
and S. Matsunaga
中科院分区：
文献类型：
--
作者：
V. Peddie;K. Takada;S. Okuda;Y. Ise;Y. Morii;N. Yamawaki;T. Takatani;O. Arakawa,⊥ S. Okada;and S. Matsunaga
我们从狼毒中发现了新的糖基化脂肪酸酰胺类化合物--狼毒皂苷。海绵。通过提取液的LC-MS分析结合分离前样品的细胞毒性试验对它们进行检测。通过对核磁共振和串联FABMS数据的分析确定了它们的平面结构。得到了红景天苷A1和A2(1和2)以及红景天苷B1-B4(3-6)。仔细分析每种混合物的核磁共振和串联FABMS数据，以及将串联FABMS数据与合成模型化合物的数据进行比较，使我们能够确定混合物中各组分的结构。手性衍生化后用LC-MS测定单糖单元的绝对构型。根据异丙叉衍生物的~1H核磁共振数据，确定了脂肪酸链上邻位含氧亚甲基的相对构型。瑞香皂苷B1-B4(3-6)的混合物对HeLa细胞具有中等的杀伤活性，IC50值为9μM，而瑞香皂苷A1和A2(1和2)的混合物在10μM的浓度下对HeLa细胞没有活性。
We have discovered new glycosylated fatty acid amides, stellettosides, from aStellettasp. marine sponge. They were detected through LC-MS analysis of the extract combined with the cytotoxicity assay of the prefractionated sample. Their planar structures were determined by analyses of the NMR and tandem FABMS data. Stellettosides A1 and A2 (1and2) as well as stellettosides B1–B4 (3–6) were obtained as inseparable mixtures. Careful analysis of the NMR and tandem FABMS data of each mixture, along with comparison of the tandem FABMS data with that of a synthetic model compound, permitted us to assign the structure of the constituents in the mixture. The absolute configuration of the monosaccharide unit was determined by LC-MS after chiral derivatization. The relative configurations of the vicinal oxygenated methines in the fatty acid chains were assigned by the1H NMR data of the isopropylidene derivative. The mixture of stellettosides B1–B4 (3–6) exhibit moderate cytotoxic activity against HeLa cells with an IC50value of 9 μM, whereas the mixture of stellettosides A1 and A2 (1 and 2) was not active at a concentration of 10 μM.