Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.
Mar Drugs. 2023 Jul 18;21(7):405. doi: 10.3390/md21070405.
Four new chlorinated cycloaromatized enediyne compounds, jejucarbosides B-E (-), were discovered together with previously-identified jejucarboside A from a marine actinomycete strain. Compounds - were identified as new chlorinated cyclopenta[]indene glycosides based on 1D and 2D nuclear magnetic resonance, high-resolution mass spectrometry, and circular dichroism (CD) spectra. Jejucarbosides B and E bear a carbonate functional group whereas jejucarbosides C and D are variants possessing 1,2-diol by losing the carbonate functionality. It is proposed that the production of - occurs via Bergman cycloaromatization capturing Cl and H in the alternative positions of a -benzyne intermediate derived from a 9-membered enediyne core. Jejucarboside E () displayed significant cytotoxicity against human cancer cell lines including SNU-638, SK-HEP-1, A549, HCT116, and MDA-MB-231, with IC values of 0.31, 0.40, 0.25, 0.29, and 0.48 μM, respectively, while jejucarbosides B-D (-) showed moderate or no cytotoxic effects.
四种新的氯化环芳烯二烯化合物，jejucarbosides B-E（-），与先前从海洋放线菌菌株中鉴定出的 jejucarboside A 一起被发现。化合物-根据 1D 和 2D 核磁共振、高分辨率质谱和圆二色性（CD）光谱被鉴定为新的氯化环戊[]茚糖苷。Jejucarbosides B 和 E 带有碳酸酯官能团，而 jejucarbosides C 和 D 是通过失去碳酸酯官能团而具有 1,2-二醇的变体。据推测，-的产生是通过 Bergman 环芳构化捕获 Cl 和 H 在衍生自 9 元烯二酮核心的 -苯乙炔中间体的替代位置上发生的。Jejucarboside E（）对包括 SNU-638、SK-HEP-1、A549、HCT116 和 MDA-MB-231 在内的人类癌细胞系表现出显著的细胞毒性，IC 值分别为 0.31、0.40、0.25、0.29 和 0.48 μM，而 jejucarbosides B-D（-）表现出中度或无细胞毒性作用。
