Zhang Xu, Yan Hai-Wei, Feng Zi-Ming, Yang Ya-Nan, Jiang Jian-Shuang, Zhang Pei-Cheng
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
Org Biomol Chem. 2020 Jul 22;18(28):5453-5457. doi: 10.1039/d0ob01014f.
Two pairs of unusual phthalide analog enantiomers, (+)- and (-)-neophathalides A and B [(+)- and (-)-1 and 2], were isolated from the rhizome of Ligusticum chuanxiong Hort. Notably, neophathalide A presented a novel spiro-[4.5]dec-6-ene skeleton that originated from an aldol condensation process from sedanonic acid. Neophathalide B is an unprecedented 3-substituted phthalide analog that possesses a four-membered lactone ring system. The structures of the compounds were established using UV, IR, HRESIMS, NMR and ECD methods. All of the compounds were evaluated for their hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury. Compounds 1a, 1b, and 2a exhibited moderate hepatoprotective activity compared with the positive control drug bicyclol at a concentration of 10 μM (p < 0.01).
从川芎的根茎中分离出两对不同寻常的苯酞类似对映体，即(+)-和(-)-新苯酞A和B [即(+)-和(-)-1和2]。值得注意的是，新苯酞A呈现出一种新颖的螺[4.5]癸-6-烯骨架，它源自塞丹酮酸的羟醛缩合过程。新苯酞B是一种前所未有的3-取代苯酞类似物，具有一个四元内酯环系统。通过紫外光谱、红外光谱、高分辨电喷雾电离质谱、核磁共振光谱和电子圆二色光谱法确定了这些化合物的结构。评估了所有化合物对N-乙酰对氨基酚诱导的HepG2细胞损伤的肝保护活性。在10 μM的浓度下，与阳性对照药物双环醇相比，化合物1a、1b和2a表现出中等程度的肝保护活性(p < 0.01)。
