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目的研究孜然芹Cuminum cyminum干燥成熟果实的化学成分。方法利用硅胶柱色谱法、Sephadex LH-20凝胶柱色谱法、中压柱色谱法、高压快速制备色谱及半制备高效液相色谱等方法分离纯化,通过理化常数和NMR、MS波谱等方法鉴定化合物结构。结果从孜然芹籽甲醇提取物中分离得到15个化合物,分别鉴定为黄芪苷(1)、6β-羟基甘草次酸(2)、乌苏酸(3)、槲皮素(4)、原儿茶酸(5)、(6R,7E,9R)-9-羟基-4,7-巨豆二烯-3-酮(6)、4,5-二咖啡酰基奎宁酸甲酯(7)、3,5-二咖啡酰基奎宁酸甲酯(8)、松香(9)、山柰酚3-O-β-D-吡喃葡萄糖基(1→2)-β-D-吡喃葡萄糖基-7-O-α-L-鼠李糖(10)、枯茗酸(11)、cuminoside A(12)、木犀草素(13)、芹菜素-7-O-β-D-(6″-O-乙酰基)-葡萄糖苷(14)、5,7,4′-三羟基黄酮(15)。结论化合物2、3、6~10和14为首次从孜然芹属植物中分离得到。
Objective To study the chemical constituents of dry ripe fruit of Cuminum cyminum. Methods The compounds were separated and purified by silica gel column chromatography, Sephadex LH-20 column chromatography, medium pressure column chromatography, high pressure rapid preparative chromatography and semi-preparative high performance liquid chromatography. The compounds were identified by physicochemical constants, NMR and MS spectra Compound Structure. Results Fifteen compounds were isolated from methanol extracts of Caraway seeds and identified as astragaloside (1), 6β-hydroxyglycyrrhetinic acid (2), ursolic acid (3), quercetin (4) Catechin (5), (6R, 7E, 9R) -9-hydroxy-4,7-caroten-3-one , Methyl 3,5-dicaffeoylquinic acid (8), rosin (9), kaempferol 3-O-β-D-glucopyranosyl 7-O-α-L-rhamnose (10), cumcin acid (11), cuminoside A (12), luteolin (13), apigenin-7- “-O-acetyl” -glucoside (14), 5,7,4’-trihydroxyflavone (15) .CONCLUSION Compounds 2, 3, 6-10 and 14 were isolated from the genus Cuminum for the first time .