目的 研究菊科植物臭蒿Artemisia hedinii地上部分的化学成分及其抗肝损伤活性。方法 采用D101型大孔吸附树脂、Sephadex LH-20凝胶、MCI CHP20P树脂、ODS反相硅胶以及半制备HPLC等柱色谱技术进行分离纯化，根据理化性质和NMR、MS波谱数据鉴定化合物结构，采用利福平诱导人肝癌HepG2细胞肝损伤模型评价单体化合物的抗肝损伤活性。结果 从臭蒿中分离得到了21个化合物，分别鉴定为brickellin（1）、芹菜素（2）、chrysosplenoside I（3）、木犀草素-5-O-β-D-葡萄糖苷（4）、木犀草素-7-O-β-D-葡萄糖苷（5）、高车前苷（6）、5,2′,5′-三羟基-3,7,4′-三甲氧基黄酮-2′-O-β-D-葡萄糖苷（7）、木犀草素（8）、槲皮素-3-O-β-D-葡萄糖苷（9）、11,12-二羟基桉叶烷-4-烯-3-酮（10）、(7R,9S,10S)-9-乙酰氧基桉叶烷-3,5,11(13)-三烯-12-酸（11）、9β-乙酰氧基-4,5-脱氢-4(15)-二氢广木香酸（12）、artetourneforin B（13）、9-氧代-6α,7α(H)-桉叶烷-4,11(13)-二烯-12,6-内酯（14）、3α,16α-二羟基-4,4,9,14-四甲基-(9β,10α)-19-去甲孕甾-5-烯-11,20-二酮（15）、4,5-O-二咖啡酰基奎宁酸甲酯（16）、3,5-O-二咖啡酰基奎宁酸甲酯（17）、(E)-茼蒿素（18）、(Z)-茼蒿素（19）、(7S,8R)-二氢脱氢二松柏醇（20）、3,3′,4,4′-四羟基-δ-苯并二氢吡喃酸乙酯（21）。所有化合物的抗肝损伤活性评价结果表明，化合物2、4、5、9～11、13、20可显著降低利福平诱导的HepG2细胞的丙氨酸氨基转移酶（alanine aminotransferase，ALT）/天冬氨酸转氨酶（aspartate aminotransferase，AST）的水平（P＜0.05、0.01）。结论 化合物1、3、7、10、13、15、20为首次从菊科植物中分离得到，化合物4为首次从蒿属中分离得到，化合物2、5、6、8、9、14、16～19为首次从臭蒿中分离得到。化合物2、4、5、9～11、13、20具有抗肝损伤潜力。

Objective To investigate the chemical constituents of the aerial parts of Artemisia hedinii (Asteraceae) and their anti-hepatotoxic activity. Methods Column chromatography techniques, including D101 macroporous adsorption resin, Sephadex LH-20 gel, MCI CHP20P resin, ODS reversed-phase silica gel, and semi-preparative HPLC, were employed to isolate compounds from A. hedinii. The structures of compounds were identified by physicochemical properties and spectroscopic data (NMR/MS). The anti-hepatotoxic activity of the isolates was evaluated using a rifampicin-induced hepatotoxicity model in HepG2 cells. Results A total of 21 compounds were isolated and identified as follows: brickellin (1), apigenin (2), chrysosplenoside I (3), luteolin-5-O-β-D-glucoside (4), luteolin-7-O-β-D-glucoside (5), homoplantaginin (6), 5,2′,5′-trihydroxy-3,7,4′-trimethoxyflavone-2′-O-β-D-glucoside (7), luteolin (8), quercetin-3-O-β-D-glucoside (9), 11,12-dihydroxyeudesm-4-en-3-one (10), (7R,9S,10S)-9-acetoxyeudesm-3,5,11(13)-trien-12-oic acid (11), 9β-acetoxy-4,5-dehydro-4(15)-dihydrocosric acid (12), artetourneforin B (13), 9-oxo-6α,7α(H)-eudesm-4,11(13)-dien-12,6-olide (14), 3α,16α-dihydroxy-4,4,9,14-tetramethyl-(9β,10α)-19-norpregn-5-ene-11,20-dione (15), methyl 4,5-di-O-caffeoyl-quinate (16), methyl 3,5-O-dicaffeoylquinate (17), (E)-tonghaosu (18), (Z)-tonghaosu (19), (7S,8R)-dihydrodehydrodico- niferyl alcohol (20), and ethyl 3,3′,4,4′-tetrahydroxy-δ-truxinate (21). The anti-hepatotoxic activity evaluation of all compounds demonstrated that compounds 2, 4, 5, 9—11, 13, and 20 significantly reduced rifampicin-induced alanine aminotransferase (ALT)/ aspartate aminotransferase (AST) levels in HepG2 cells (P < 0.05, 0.01). Conclusion Seven compounds (1, 3, 7, 10, 13, 15, and 20) were isolated for the first time from Asteraceae plants. Compound 4 was first reported from the genus Artemisia. Ten compounds (2, 5, 6, 8, 9, 14, 16—19) were identified for the first time from the title plant. Compounds 2, 4, 5, 9—11, 13, and 20 exhibit potential anti-hepatotoxic activity.

R284.1

国家重点研发计划资助(2019YFC1712300); 江西中医药大学校级科技创新团队发展计划(CXTD22002)