目的 对小茴香Foeniculum vulgare醋酸乙酯部位化学成分及其对酪氨酸酶活性影响的研究。方法 利用硅胶、D101大孔吸附树脂、MCI、ODS、Sephadex LH-20及半制备型高效液相等色谱技术进行分离纯化，根据理化性质和波谱数据鉴定化合物结构；运用酪氨酸酶催化L-酪氨酸速率法筛选化合物的酪氨酸酶抑制活性，对从盐炙小茴香分离出的化合物进行抗酪氨酸酶活性评价，最后通过分子对接技术对其进行验证。结果 从盐炙小茴香醋酸乙酯部位分离得到20个化合物，分别鉴定为bombasinol A（1）、齐墩果酸（2）、山柰素（3）、槲皮素（4）、（1R，2R）-1-（4-methoxypheny） propane-1，2-diol（5）、（1S，2R）-1-（4-methoxyphenyl） propane-1，2-diol（6）、（3S，5R，6S，7E）-3，5，6-trihydroxy-7-megastigmen-9-one（7）、齐墩果酮酸（8）、刺五加酮（9）、phenylpropanoid（10）、（Z）-4-[30-（β-D-glucopyranosyloxy） butylidene]-3，5，5-trimethyl-2-cyclohexen-l-one（11）、3-oxo-α-ionol-β-D-glucopyranoside（12）、（+）-松脂素-β-D-吡喃葡萄糖苷（13）、trans-4-（1-propenyl）-phenol-β-D-glucopyranoside（14）、1-O-β-D-glucopyranosyl-4-allybenzene（15）、3-hydroxyestragole β-D-glucopyranoside（16）、黄花夹竹桃黄酮（17）、3，5-dihydroxyestragole 3-O-β-D-glucopyranoside（18）、水杨酸（19）和benzyl β-D-glucopyranoside（20）。酪氨酸酶活性抑制实验表明，盐炙小茴香中分离得到的20个化合物中5个（化合物4、13～15和17）具有良好的抗酪氨酸酶活性，其半数抑制浓度（median inhibition concentration，IC₅₀）值分别为0.783、0.532、0.575、0.113、0.092 mg/mL，阳性药β-熊果苷IC₅₀值为1.784 mg/mL，同时分子对接结果也显示化合物17的结合能为-5.74 kJ/mol，化合物15的结合能为-3.5 kJ/mol。结论 化合物1为伞形科首次分离得到，化合物3、7～17为茴香属首次分离得到；化合物4、13～15和17均具有较好的抑制酪氨酸酶活性，其中化合物15和17抑制效果最好，分子对接结果也显示化合物17抑制效果强于化合物15，与实验结果一致。

Objective To study the chemical compositions of the ethyl acetate part of Foeniculi Fructus and their effects on tyrosinase activities. Methods The compounds were isolated and purified by using various chromatographic techniques, including silica gel, D101 macroporous resins, MCI, ODS, Sephadex LH-20 and semi-prepative high performance liquid phase. Their structures were identified on the basis of physicochemical properties and spectral data. The tyrosinase inhibitory activities of compounds was screened by tyrosinase catalytic L-tyrosine rate method to evaluate the anti-tyrosinase activities of compounds isolated from salt-processed Foeniculi Fructus. Finally, the compounds were verified by molecular docking technique. Results A total of 20 compounds were isolated from the ethyl acetate part of Foeniculi Fructus, which were identified as bombasinol A (1), oleanolic acid (2), kaempferide (3), quercetin (4), (1R,2R)-1-(4-methoxyphenyl)propane-1,2-diol (5), (1S,2R)-1-(4-methoxyphenyl)propane-1,2-diol (6), (3S,5R,6S,7E)-3,5,6-trihydroxy-7-megastigmen-9-one (7), oleanonic acid (8), acanthone (9), phenylpropanoid (10), (Z)-4-[30-(β-D-glucopyranosyloxy)butylidene]-3,5,5-trimethyl-2-cyclohexen-l-one (11), 3-oxo-α-ionol-β-D-glucopyranoside (12), (+)-pinoresinol-β-D-glucopyranoside (13), trans-4-(1-propenyl)-phenol-β-D-glucopyranoside (14), 1-O-β-D-glucopyranosyl-4-allybenzene (15), 3-hydroxyestragole β-D-glucopyranoside (16), thevetiaflavone (17), 3,5-dihydroxyestragole 3-O-β-D-glucopyranoside (18), salicylic acid (19) and benzyl β-D-glucopyranoside (20). Tyrosinase activities inhibition assay showed that five of the 20 compounds isolated from salt-processed Foeniculi Fructus had good anti-tyrosinase activities with half maximal inhibitory concentration (IC₅₀) values of 0.783, 0.532, 0.575, 0.113, 0.092 mg/mL, respectively, and the positive drug, β-arbutin, had an IC₅₀ value of 1.784 mg/mL. Meanwhile, the molecular docking results showed the binding energy of compound 17 was −5.74 kJ/mol, and that of compound 15 was −3.5 kJ/mol. Conclusion Compound 1 was isolated for the first time from Umbelliferae, compounds 3, 7−−17 were isolated for the first time from Anethole, compounds 4, 13−15 and 17 all had good tyrosinase inhibitory activities, among which compounds 15 and 17 had the best inhibitory effect, and the molecular docking results also showed that the inhibitory effect of compound 17 was stronger than that of compound 15, which was in agreement with the experimental results.

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国家自然科学基金资助项目（82260758）；国家自然科学基金资助项目（31860092）；云南省高层次人才培养支持计划“青年拔尖人才”专项（YNWR-QNBJ-2020-255）；云南省基础研究计划面上项目（202101AT070254）；云南省科技人才和平台计划（202105AG070012XS23004）