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Conjugated Polyene Ketones From the Marine Sponge Clathria (Thalysias) Reinwardti (Vosmaer, 1880) and Their Cytotoxic Activity
Natural Product Communications ( IF 1.5 ) Pub Date : 2021-09-20 , DOI: 10.1177/1934578x211043732
Bui H. Tai 1, 2 , Dan T. Hang 1 , Do T. Trang 1, 2 , Pham H. Yen 1 , Phan T. T. Huong 1 , Nguyen X. Nhiem 1, 2 , Do C. Thung 3 , Do T. Thao 4 , Nguyen T. Hoai 5 , Phan V. Kiem 1, 2
Affiliation  

Five conjugated polyene ketones (1-5) were isolated from the methanol extract of the marine sponge Clathria (Thalysias) reinwardti (Vosmaer, 1880) living in the coastal waters of Vietnam. Their structures were determined to be 8-(2′,3′,4′-trimethylphenyl)-6-methyl-oct-3(E),5(E),7(E)-trien-2-one (1), 13-apoastaxanthinone (2), 9-apoastaxanthinone (3), 2,3-dehydro-4-oxo-β-ionone (4), and 4-(2′,3′,4′-trimethylphenyl)-but-3(E)-en-2-one (5), by extensive analysis of high-resolution electron spray ionization mass spectrum (HR-ESI-MS), one-dimensional, and two-dimensional (2D) nuclear magnetic resonance (NMR) spectra, as well as by comparison of the spectral data with those reported in the literature. Compound 1 was new, compounds 2 to 4 were isolated from nature for the first time, and the chemical structure as well as the NMR assignments, of 5 were indicated by 2D NMR for the first time. Additionally, compound 5 exhibited cytotoxic activity against the human cancer cells SK-LU-1, SK-Mel-2, MCF-7, and Hep-G2 with half-minimal inhibitory concentration (IC50) values of 15.12 ± 3.43, 17.41 ± 2.83, 33.12 ± 3.39, and 34.38 ± 3.52 µM, respectively, but displayed only a weak cytotoxic effect on the normal HEK-239A cells (IC50 64.67 ± 3.67 µM). Compound 5 also significantly increased Caspase-3 activity in SK-LU-1 cells at concentrations of 10, 15, and 20 µM.



中文翻译:

来自海洋海绵体 (Thalysias) Reinwardti (Vosmaer, 1880) 的共轭多烯酮及其细胞毒活性

从生活在越南沿海水域的海洋海绵Clathria ( Thalysias ) reinwardti (Vosmaer, 1880)的甲醇提取物中分离出五种共轭多烯酮 (1-5) 。它们的结构被确定为 8-(2',3',4'-trimethylphenyl)-6-methyl-oct-3( E ),5( E ),7( E )-trien-2-one (1) , 13-apoastaxanthinone (2), 9-apoastaxanthinone (3), 2,3-dehydro-4-oxo- β -ionone ( 4), and 4-(2',3',4'-trimethylphenyl)-but- 3( E)-en-2-one (5),通过对高分辨率电子喷雾电离质谱 (HR-ESI-MS)、一维和二维 (2D) 核磁共振 (NMR) 谱的广泛分析,以及通过将光谱数据与文献中报道的数据进行比较。化合物1为新化合物,化合物2~4为首次从自然界中分离得到,化合物5的化学结构及核磁共振谱图均首次通过二维核磁共振显示。此外,化合物 5 对人癌细胞 SK-LU-1、SK-Mel-2、MCF-7 和 Hep-G2 表现出细胞毒活性,半数抑制浓度 (IC 50 ) 值为 15.12 ± 3.43, 17.41 ±分别为 2.83、33.12 ± 3.39 和 34.38 ± 3.52 µM,但对正常 HEK-239A 细胞(IC 5064.67 ± 3.67 µM)。在 10、15 和 20 µM 的浓度下,化合物 5 还显着增加了 SK-LU-1 细胞中的 Caspase-3 活性。

更新日期:2021-09-20
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