Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China.
Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China.
Phytochemistry. 2020 Apr;172:112282. doi: 10.1016/j.phytochem.2020.112282. Epub 2020 Feb 6.
Seventeen highly oxygenated and rearranged limonoids, including nine previously undescribed phragmalin-type limonoids with 1,8,9- and 8,9,30-orthesters (entanutilins C-K, 1-9), three undescribed limonoids with rare rearranged-6/6/7/5 skeleton (entanutilins L-N, 10-12), and 5 known limonoids, were isolated from the stem barks of Entandrophragma utile from Ghana (Africa). Their structures including absolute configurations were elucidated based on comprehensive spectroscopic analyses, such as HRESIMS, 1D/2D-NMR, CD exciton chirality method, time-dependent density functional theory (TDDFT)/ECD calculations, and single-crystal X-ray diffraction. Bioactivity screenings suggested that some of these compounds effectively reversed resistance in MCF-7/DOX cells at a nontoxic concentration of 30 μM with 6- to 19-fold enhancing effects.
从加纳（非洲）的 Entandrophragma utile 的茎皮中分离得到了 17 种高度氧化和重排的柠檬苦素，包括 9 种以前未描述的具有 1,8,9-和 8,9,30-orthoester（entanutilin C-K，1-9）的 phragmalin 型柠檬苦素，3 种具有罕见重排-6/6/7/5 骨架的 limonoids（entanutilin L-N，10-12）和 5 种已知的柠檬苦素。基于全面的光谱分析，如 HRESIMS、1D/2D-NMR、CD 外消旋手性方法、时间依赖密度泛函理论（TDDFT）/ECD 计算和单晶 X 射线衍射，确定了它们的结构包括绝对构型。生物活性筛选表明，其中一些化合物在非毒性浓度 30 μM 下有效逆转 MCF-7/DOX 细胞中的耐药性，增强效果为 6 至 19 倍。
