目的 对篦齿虎耳草Saxifraga umbellulata var.pectinata的正丁醇部位化学成分进行研究。方法 利用多种色谱层析方法(硅胶柱色谱、Sephadex LH-20凝胶柱色谱、ODS反相柱色谱和半制备HPLC等)进行分离纯化,运用理化性质结合现代波谱学(紫外分光光度法、红外分光光度法、核磁共振波谱法、质谱等)技术进行结构鉴定。结果 从篦齿虎耳草正丁醇部位中分离得到31个化合物,分别鉴定为(2S,4S)-6-(4-羟基苯基)已烷-2,4-二醇(1)、(4R)-4-羟基-6-(3,4-二羟基苯基)己烷-4-醇(2)、(2R)-6-(3,4-二羟基苯基)-2-羟基己烷-4-酮(3)、6-(4-羟基苯基)已烷-2,4-二醇(4)、(E)-9,10-二羟基-苯已基-2-烯-4-酮(5)、rhododendrin(6)、对香豆酸(7)、对羟基苯丙酸(8)、异落叶松脂素(9)、(5S)-5-丁氧基-7-(3,4-二羟基苯基)-1-(4-羟基苯基)-3-庚酮(10)、(5S)-5-丁氧基-1,7-二(4-羟基苯基)-3-庚酮(11)、1-(4-羟基苯基)-7-(3,4-二羟基苯基)-5-O-β-D-葡萄糖苷-3-庚酮(12)、5-羟基-1-(4-羟基苯基)-7-(3,4-二羟基苯基)-3-庚酮(13)、alusenone(14)、白桦林烯酮(15)、hannokinol(16)、alnuheptanoid A(17)、5-羟基-1,7-二(4-羟基苯基)-3-庚酮(18)、槲皮素-3,7-二-O-α-L-鼠李糖苷(19)、山柰酚-3,7-二-O-α-L-鼠李糖苷(20)、金丝桃苷(21)、鼠李亭-3-O-半乳糖苷(22)、鼠李素-3-O-鼠李糖苷(23)、槲皮苷(24)、杨梅素-3-O-β-D-半乳糖苷(25)、山柰酚-3-O-(6'-乙酰基)-β-D-半乳糖苷(26)、槲皮素(27)、催吐萝芙木醇(28)、8,9-dihydromegastigmane-4,6-diene-3-one(29)、tubiflorone(30)、chakyunglupulin A(31)。结论 化合物1~3为新化合物,依次命名为虎耳草酚二醇、虎耳草酚和(R)-纤孔菌酚A,化合物4、8~11、13、17~20、22、23、26、28~31均为首次从虎耳草属植物中分离报道,化合物6、7、12、14、15、16、24和25均为首次从篦齿虎耳草中分离报道,其中化合物10和11为人工产物。上述黄酮类、二苯庚烷类、单苯烷类和环烯类成分在虎耳草属植物中具有一定的化学分类学价值。

Objective To investigate the chemical constituents of Saxifraga umbellulata var. pectinata (SUP). Method N-butanol fraction of SUP extract was isolated and purified by a variety of chromatographic methods including silica gel, Sephadex LH-20 gel and semi-preparative HPLC. And the isolated compounds' structures were elucidated through the analysis of their physico-chemical properties combined with the modern spectroscopic techniques, such as UV, IR, NMR and MS, et al. Result A total of 31 compounds were isolated. They were identified as (2S,4S)-6-(4-hydroxyphenyl)hexane-2,4-diol (1), (4R)-6-(3,4- dihydroxyphenyl) hexane-4-ol (2), (2R)-6-(3,4-dihydroxyphenyl)-2-hydroxyhexan-4-one (3), 6-(4-hydroxyphenyl)hexane-2,4-diol (4), (E)9, 10-dihydroxy-phenylhex-2-en-4-one (5), rhododendrin (6), p-coumaric acid (7), 3-(4-hydroxyphenyl)propanoic acid (8), isolariciresinol (9), (5S)-5-butynoxy-7-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)heptan-3-one (10), (5S)-5-Butyloxy-1,7- di(4-hydroxyphenyl)-3-heptanone (11), 1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)-5-O-β-D-glucopyranosyl-heptan-3-one (12), 5-hydroxy-1-(4-hydroxyphenyl)-7- (3,4-dihydroxyphenyl)-3-heptanone (13), alusenone (14), platyphyllenone (15), hannokinol (16), alnuheptanoid A (17), 5-hydroxy-1,7-bis(4-hydroxyphenyl)-3-heptanone (18), quercetin 3,7-di-O-α-L-rhamnoside (19), kaempferol 3,7-O-α-L-dirhamnopyranoside (20), hyperoside (21), rhamnetin-3-O-galactopyranoside (22), rhamnetin-3-O-rhamnoside (23), quercitrin (24), myricetin-3-O-β-D-galactopyranoside (25), kaempferol 3-O-(6'-acetyl)-β-D-galactopyranoside (26), quercetin (27), vomifoliol (28), 8,9-dihydromegastigmane-4,6-diene-3-one (29), tubiflorone (30), chakyunglupulin A (31). Conclusion Compounds 1-3 are new compounds, sequentially named as saxiphenadiol, saxifraphenol, and (R)-inonophenol A. Compounds 4, 8, 9, 10, 11, 12, 13, 17-20, 22, 23, 26, and 28-31 were isolated from Genus Saxifraga for the first time. Compounds 6, 7, 12, 14, 15, 16, 24 and 25 were isolated from S. umbellulata var. pectinata for the first time. Compounds 10 and 11 are the butylated artificial substances produced during the extraction. Furthermore, the above-mentioned flavonoids, diphenylheptanes, monophenyls, and cycloenes have certain chemical taxonomic value in plants of the genus Saxifraga.

国家自然科学基金地区基金资助项目（82260825）；江西中医药大学校级科技创新团队发展计划（CXTD22002）