目的 研究牛耳枫Daphniphyllum calycinum叶的化学成分及对人非小细胞肺癌A549细胞的细胞毒活性。方法 运用多种柱色谱技术进行分离纯化，并采用多种波谱技术鉴定化合物结构；同时采用CCK8法对所分离化合物进行体外A549细胞毒活性测试。结果 从牛耳枫叶分离得到9个化合物，分别鉴定为 (Z)-6-羟基-2-(4-羟基苯基)-5-(1-丙烯基)苯并呋喃-3-甲酸甲酯（1）、(E)-2-(4-羟基苯基)-5-(1-丙烯基)苯并呋喃-3-甲酸甲酯（2）、4-羟基-3-甲氧基苯甲酸-3,5-二羟基苯酯（3）、methyl (E)-6-hydroxy-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran3-carboxylate（4）、4-[(2S)-3,4-dihydro-5,7-dimethoxy-2H-1-benzopyran-2-yl]phenol（5）、5-O-methylafzelechin（6）、儿茶素（7）、表儿茶素（8）和香橙素（9）。细胞毒活性显示，化合物1、2和4有一定的抑制活性，半数抑制浓度（median inhibition concentration，IC₅₀）分别为（8.32±1.50）、（14.03±2.10）、（27.42±0.95）μmol/L，其他化合物在40 μmol/L内无明显活性。结论 化合物1、2和4为苯骈呋喃类木脂素类化合物，3为香草酸衍生物，5～8为黄烷醇类化合物，9为黄酮醇化合物。其中化合物1和3为新化合物，分别命名为牛耳枫素A和牛耳枫素C；化合物2为新天然产物，命名为牛耳枫素B；化合物5～9为首次从牛耳枫中分离得到。化合物1和2具有较好的A549细胞毒活性。

Objective This study aims to investigate the chemical constituents of the leaves of Daphniphyllum calycinum and evaluate their in vitro cytotoxic activity against human non-small cell lung carcinoma cells (A549). Methods A variety of chromatographic techniques were employed to separate and isolate compounds. Multiple spectroscopic methods were used to identify the structures. The cytotoxic activity of the isolated compounds against A549 cells was evaluated by CCK-8 assay. Results Nine compounds were isolated from the leaves of D. calycinum and were identified as methyl (Z)-6-hydroxy-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-3-carboxylate (1), methyl (E)-2-(4-hydroxyphenyl)-5-(1-propen-1-yl)-3-benzofurancarboxylate (2), (3,5-dihydroxyphenyl)-4-hydroxy-3-methoxybenzoate (3), methyl (E)-6-hydroxy-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran3-carboxylate (4), 4-[(2S)-3,4-dihydro-5,7-dimethoxy-2H-1-benzopyran-2-yl]phenol (5), 5-O-methylafzelechin (6), catechin (7), epicatechin (8), dihydrokaempferol (9). The cytotoxicity assay showed that compounds 1, 2 and 4 exhibited moderate inhibitory activity with IC₅₀ values of (8.32 ± 1.50), (14.03 ± 2.10), and (27.42 ± 0.95) μmol/L, respectively. Other compounds showed no significant activity at concentrations up to 40 μmol/L. Conclusion Compounds 1, 2 and 4 were identified as benzofuran-type lignans, 3 was a vanillic acid derivative, 5—8 were flavanols, and 9 was a flavone. Among them, 1 and 3 were new compounds and were named as daphnicalycins A and C, respectively. Compound 2 was a new natural product and was named as daphnicalycin B. 5—9 were first isolated from D. calycinum. Compounds 1 and 2 exhibited potential cytotoxic activity against A549 cells.

R284.1

国家自然科学基金资助项目（32470428）