Cytotoxic Glycosylated Fatty Acid Amides from a Stelletta sp. Marine Sponge

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• 作者：Victoria Peddie ; Kentaro Takada ; Shujiro Okuda ; Yuji Ise ; Yasuhiro Morii ; Nobuhiro Yamawaki ; Tomohiro Takatani ; Osamu Arakawa ; Shigeru Okada ; Shigeki Matsunaga
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：November 25, 2015
• 年：2015
• 卷：78
• 期：11
• 页码：2808-2813
• 全文大小：289K
• ISSN：1520-6025

文摘

We have discovered new glycosylated fatty acid amides, stellettosides, from a Stelletta sp. 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 (1 and 2) as well as stellettosides B1鈥揃4 (3鈥?b>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 the ¹H NMR data of the isopropylidene derivative. The mixture of stellettosides B1鈥揃4 (3鈥?b>6) exhibit moderate cytotoxic activity against HeLa cells with an IC₅₀ value of 9 渭M, whereas the mixture of stellettosides A1 and A2 (1 and 2) was not active at a concentration of 10 渭M.