目的 研究牛耳朵Primulina eburnea干燥全草的化学成分。方法 利用正、反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱及半制备RP-HPLC等方法进行分离纯化，利用NMR、MS等多种波谱学手段确定化合物结构。随后采用MTT法评价部分化合物对人非小细胞肺癌A549细胞的细胞毒活性，并对部分化合物进行抗氧化活性筛选。结果 从牛耳朵全草醋酸乙酯部分分离得到23个化合物，分别鉴定为1,6-dihydroxy-7-methoxy-2-methylanthr-quinone（1）、soranjidiol（2）、1,4,7-trihydroxy-2-methyl-9,10-anthraquinone（3）、digiferruginol（4）、1,4-dihydroxy-2-hydroxymethyl-9,10-anthraquinone（5）、1,6,7-trihydroxy-2-methyl-9,10-anthracenedione（6）、(R)-7,8-dihydroxy-α-dunnione（7）、3-amino-2-methoxy-carbonyl-1,4-naphthoquinone（8）、木犀草素（9）、异落叶松脂素（10）、七叶内酯（11）、酪醇（12）、对香豆酸（13）、咖啡酸甲酯（14）、benzyl O-β-D-glucopyranoside（15）、4-O-benzyl-D-glucopyranoside（16）、3,4-dihydroxyph-enylethyl alcohol 8-O-β-glucopyrnoside（17）、cuneataside A（18）、对羟基苯甲醛（19）、尼泊金甲酯（20）、对羟基苯乙酮（21）、香草醛（22）和香草酸（23）。化合物8 对A549细胞有显著的细胞毒作用，其半数抑制浓度（median inhibition concentration，IC₅₀）值为3.866 μmol/L，活性高于阳性药顺铂（IC₅₀＝9.895 μmol/L）。化合物5 ～7 和9 ～11 表现出显著的抗氧化活性，其中化合物9 和11 的抗氧化活性高于阳性药。结论 化合物16 为新天然产物，化合物1 ～3 、6 和8 ～22 为首次从报春苣苔属植物中分离得到，化合物23 为首次从牛耳朵中分离得到。部分化合物表现出较好的细胞毒活性和抗氧化活性，验证了牛耳朵中抗肿瘤和抗氧化的活性物质基础，为黔产牛耳朵的深度开发利用提供了科学依据。

Objective To study the constituents of the whole plant of Niuerduo [Primulina eburnea (Hance) Y. Z. Wang]. Methods Silica gel column chromatography, Sephadex LH-20 column chromatography, semi-preparative RP-HPLC and other methods were used for the separation and purification. NMR and MS were used to identify the structures of the compounds. Subsequently, the cytotoxic activities of some compounds against A549 cell line were evaluated by MTT method, and the antioxidant activities of some compounds were evaluated by DPPH method and ABTS method, respectively. Results A total of 23 compounds were isolated from Primulina eburnea, which were identified as 1,6-dihydroxy-7-methoxy-2-methylanthr-quinone (1), soranjidiol (2), 1,4,7- trihydroxy-2-methyl-9,10-anthraquinone (3), digiferruginol (4), 1,4-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (5), 1,6,7- trihydroxy-2-methyl-9,10-anthracenedione (6), (R)-7,8-dihydroxy-α-dunnione (7), 3-amino-2-methoxycar-bonyl-1,4- naphthoquinone (8), luteoline (9), (+)-isolariciresinol (10), esculetin (11), tyrosol (12), p-coumaric acid (13), caffeic acid methy ester (14), benzyl O-β-D-glucopyranoside (15), 4-O-benzyl-D-glucopyranoside (16), 3,4-dihydroxyphenylethyl alcohol 8-O-β- glucopyrnoside (17), cuneataside A (18), 4-hydroxybenzaldehyde (19), methyl-4-hydroxybenzoate (20), 1-(4- hydroxyphenyl)-ethanone (21), vanillin (22) and vanillic acid (23). Compound 8 had significant cytotoxic effect on A549 cells, with the IC₅₀ value of 3.866 μmol/L, and its activity was higher than the positive drug cisplatin (IC₅₀= 9.895 μmol/L). Compounds 5—7 and 9—11 showed significant antioxidant activity, and compounds 9 and 11 showed stronger antioxidant activity than positive drugs. Conclusion A total of 23 compounds were isolated from the whole plant of P. eburnea, of which compound 16 was a new natural product. Compounds 1—3, 6 and 8—22 were isolated from gene Primulina for the first time. Compound 23 was isolated from P. eburnea for the first time. Some compounds showed good cytotoxic activity and antioxidant activity, which proved the basis of antitumor and antioxidant activities substances in P. eburnea, and provided the scientific basis for the in-depth development and utilization of P. eburnea from Guizhou.

R284.1

国家自然科学基金资助项目（31860074）；国家自然科学基金资助项目（32060081）；国家自然科学基金资助项目（U1812403）；贵州医科大学学术新苗项目（19NSP003）；贵州省科技计划项目（黔科中引地 [2022] 4015）