State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, PR China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550014, PR China.
Qianxinan Karst Regional Development Institute of Guizhou, Xingyi 562400, PR China.
Phytochemistry. 2022 Aug;200:113186. doi: 10.1016/j.phytochem.2022.113186. Epub 2022 Apr 30.
Eleven undescribed limonoids, cipacinerasins A-K, involving of four diverse carbon skeletal types, along with fifteen known analogues, were isolated from the branches and leaves of Cipadessa baccifera. Within them, cipacinerasins A and B feature a rearranged tetrahydropyranyl ring B formed between C-8 and C-30, are unusual miscellaneous-type limonoids. Cipacinerasins E and F are rare trijugin-type limonoids, of which the D-ring δ-lactone is cleaved. Their structures were elucidated on the basis of extensive spectroscopic data (HRESIMS, NMR, UV and IR), electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. All compounds were evaluated in vitro cytotoxicity against five human tumor cell lines (K562, HeLa, PC3, LN-Cap and Hell), and cipacinerasin E showed moderate antitumor activity with IC values ranging from 8.0 to 24.8 μM.
从三桠苦属植物的枝叶中分离得到了 11 种未被描述的柠檬苦素类化合物，包括 cipacinerasins A-K，涉及四种不同的碳骨架类型，以及 15 种已知的类似物。其中，cipacinerasins A 和 B 具有一个由 C-8 和 C-30 之间形成的重排的四氢吡喃环 B，是不寻常的混合型柠檬苦素。cipacinerasins E 和 F 是罕见的三箭型柠檬苦素，其中 D 环 δ-内酯被裂解。它们的结构是基于广泛的光谱数据（高分辨质谱、NMR、UV 和 IR）、电子圆二色性（ECD）计算和单晶 X 射线衍射分析来阐明的。所有化合物均在体外对五种人肿瘤细胞系（K562、HeLa、PC3、LN-Cap 和 Hell）进行了细胞毒性评估，cipacinerasin E 表现出中等的抗肿瘤活性，IC 值范围为 8.0 至 24.8 μM。
