Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing 100048, China.
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, China.
Molecules. 2019 Jan 16;24(2):306. doi: 10.3390/molecules24020306.
, an important medicinal plant, is widely used as a traditional Chinese medicine and spice. Using cytotoxicity-guided fractionation, nine new lignans ⁻ and ten known analogues ⁻ were obtained from the EtOH extract of the twigs of . Their structures were assigned by extensive 1D- and 2D-NMR experiments, and the absolute configurations were resolved by specific rotation and a combination of experimental and theoretically calculated electronic circular dichroism (ECD) spectra. In the cytotoxicity assay, 7',9-epoxylignans with feruloyl or cinnamoyl groups (compounds ⁻, and ) were selectively cytotoxic against NCI-H1650 cell line, while the dibenzylbutyrolactone lignans ⁻ exerted cytotoxicities against HCT-116 and A2780 cell lines. The results highlighted the structure-activity relationship importance of a feruloyl or a cinnamoyl moiety at C-9' or/and C-7 ketone in 7',9-epoxylignans. Furthermore, compound was moderate active toward protein tyrosine phosphatase 1B (PTP1B) with an IC value of 13.5 μM, and compounds ⁻, and displayed inhibitory activity against LPS-induced NO production in RAW264.7 macrophages, with IC values of 46.8, 50.1, 58.6, 47.5, and 66.5 μM, respectively.
作为一种重要的药用植物,被广泛用作中药和香料。通过细胞毒性导向分离,从 的小枝乙醇提取物中获得了 9 个新的木脂素 ⁻ 和 10 个已知类似物 ⁻ 。通过广泛的 1D 和 2D-NMR 实验确定了它们的结构,并通过比旋光度和实验与理论计算的电子圆二色性(ECD)光谱的组合确定了它们的绝对构型。在细胞毒性测定中,具有阿魏酰基或肉桂酰基的 7',9-环氧木脂素(化合物 ⁻ 、 和 )对 NCI-H1650 细胞系具有选择性细胞毒性,而二苄基丁内酯木脂素 ⁻ 对 HCT-116 和 A2780 细胞系具有细胞毒性。结果突出了 7',9-环氧木脂素中 C-9'或/和 C-7 酮上的阿魏酰基或肉桂酰基部分的结构-活性关系的重要性。此外,化合物 对蛋白酪氨酸磷酸酶 1B(PTP1B)具有中等活性,IC 值为 13.5 μM,化合物 ⁻ 、 和 对 LPS 诱导的 RAW264.7 巨噬细胞中 NO 产生具有抑制活性,IC 值分别为 46.8、50.1、58.6、47.5 和 66.5 μM。