Ye Jianghai, Xu Chuanyan, Zhao Chenliang, Luo Yuling, Zhang Jingjie, Chen Rensong, He Kang, Zou Juan
School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang, China.
The Second Affiliated Hospital of Guizhou University of Traditional Chinese Medicine, Guiyang, China.
Chem Biodivers. 2025 Jul 15:e01406. doi: 10.1002/cbdv.202501406.
Three unprecedented cycloartane triterpenoids (1-3) together with five known congeners (4-8) were isolated for the first time from the medicinal plant Kadsura longipedunculata. Their structural diversity was characterized by distinct skeletal modifications: compound 1 represents a rare 3,4-seco-cycloartane derivative featuring a 7-membered ester A-ring formed via Baeyer-Villiger oxidation, compound 2 is a schisanartane-type nortriterpenoid with unique 3,4:9,10-diseco structural motifs, while compound 3 exhibits an unprecedented 18,28-demethylated cycloartane skeleton. In addition, five known congeners (4-8) were cycloartane triterpenoids. Significantly, these structurally modified derivatives represent the first report of such skeletal variations within the K. longipedunculata genus. Structural elucidation and absolute configuration determination were achieved through comprehensive spectroscopic analysis (one-/two-dimensional nuclear magnetic resonance and high-resolution electrospray ionization-mass spectrometry) complemented by X-ray crystallographic verification and electronic circular dichroism calculation. These compounds were evaluated for their cytotoxicity and anti-inflammatory activity. Compounds 4 and 5 could inhibit nitric oxide production with 50% inhibitory concentration (IC) values of 36.45 and 28.38 µM. Compound 4 demonstrated concentration-dependent antiproliferative effects against HeLa cervical cancer cells, achieving 68.99% growth inhibition at 40 µM and an IC value of 21.40 µM.
首次从药用植物长梗南五味子中分离得到了三种前所未有的环阿尔廷烷三萜（1-3）以及五种已知的同系物（4-8）。它们的结构多样性表现为独特的骨架修饰：化合物1是一种罕见的3,4-裂环环阿尔廷烷衍生物，其具有通过拜耳-维利格氧化反应形成的七元酯A环；化合物2是一种具有独特的3,4:9,10-双裂环结构基序的南五味子烷型降三萜；而化合物3则呈现出一种前所未有的18,28-去甲基环阿尔廷烷骨架。此外，五种已知同系物（4-8）均为环阿尔廷烷三萜。值得注意的是，这些结构修饰的衍生物代表了长梗南五味子属内此类骨架变异的首次报道。通过综合光谱分析（一维/二维核磁共振和高分辨率电喷雾电离质谱）并辅以X射线晶体学验证和电子圆二色性计算，实现了结构解析和绝对构型确定。对这些化合物进行了细胞毒性和抗炎活性评估。化合物4和5能够抑制一氧化氮的产生，其半数抑制浓度（IC）值分别为36.45和28.38 μM。化合物4对人宫颈癌HeLa细胞表现出浓度依赖性的抗增殖作用，在40 μM时生长抑制率达到68.99%，IC值为21.40 μM。
