Four previously undescribed naphthohydroquinone dimers named rubipodanones A-D, together with 19 known quinones containing three known napthohydroquinone dimers named rubioncolin C, methyl 5-hydroxy-dinaphtho[1,2-2',3']furan-7,12-dione-6-carboxylate and rubialatin B, were isolated from the roots and rhizomes of Rubia podantha. Their structures and absolute configurations were determined mainly by NMR, X-ray diffraction, and computational methods. Rubipodanones C and D, the glycosides of rubipodanone A and a pair of C-3 epimer, are the first identified dimeric napthohydroquinone glycosides from the Rubia plants. All naphthohydroquinone dimers were evaluated for their cytotoxicities against ten tumor cell lines and effects on the tumor-associated NF-κB signaling pathway, and rubioncolin C showed the best cytotoxicity with IC50 value of 1.53 μM and NF-κB inhibitory activity with IC50 value of 2.97 μM. These results also demonstrated that the key roles of C-3 configuration and sugar group for biological activities of rubipodanone C.

中文翻译：

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Rubipodanones AD，来自Rubia podantha根和根茎的萘氢醌二聚体

四种先前未描述的萘氢醌二聚体，名为 rubipodanones AD，以及 19 种已知的醌，其中包含三种已知的萘并氢醌二聚体，名为 rubioncolin C,methyl 5-hydroxy-dinaphtho[1,2-2',3']furan-7,12-dione-6- carboxylate 和rubialatin B，是从Rubia podantha 的根和根茎中分离出来的。它们的结构和绝对构型主要通过核磁共振、X 射线衍射和计算方法确定。Rubipodanones C 和 D，rubipodanone A 的糖苷和一对 C-3 差向异构体，是第一个从茜草植物中鉴定出的二聚萘氢醌糖苷。评估了所有萘氢醌二聚体对 10 种肿瘤细胞系的细胞毒性和对肿瘤相关 NF-κB 信号通路的影响，并且 rubioncolin C 显示出最好的细胞毒性，IC50 值为 1。53 μM 和 NF-κB 抑制活性，IC50 值为 2.97 μM。这些结果还表明，C-3 构型和糖基对 rubipodanone C 生物活性的关键作用。