【作者】 杜慧琴；

【导师】 华会明；

【作者基本信息】 沈阳药科大学 ， 药物化学， 2005， 硕士

【摘要】 桔梗为桔梗科植物桔梗Platycodon grandiflorum(Jacq.)A. DC.的干燥根，为中国药典收载品种，具有宣肺、利咽、祛痰、排脓之功效，主要用于咳嗽痰多，胸闷不畅，咽痛，音哑，肺痈吐脓，疮疡脓不成溃；现代药理研究表明，桔梗具有抗癌活性，但对其抗肿瘤活性成分的报道较少。本论文对桔梗的化学成分和抗肿瘤活性进行了研究。在系统查阅了国内外相关文献的基础上，总结了桔梗属植物的化学、药理、临床应用和产品开发的研究进展。通过硅胶柱色谱、大孔吸附树脂柱色谱、凝胶柱色谱、制备薄层色谱、正反相中低压柱色谱及HPLC等多种色谱手段，从桔梗的乙醇提取物中共分离得到21个化合物。通过理化常数测定、光谱数据分析及化学方法等鉴定手段，鉴定了其中15个化合物的结构，包括3个三萜皂苷类成分、3个甾醇类成分、4个果糖类成分、2个含有长链的化合物以及3个其他类型成分。其中新的天然产物1个，鉴定为3-O-β-昆布二糖-2β，3β，16α，23-四羟基-齐墩果酸(1)；化合物3(platycoside H)鉴定为3-O-[β-D-吡喃木糖基-(1→4)-β-D-吡喃葡萄糖基]-桔梗酸C-28-O-β-D-呋喃芹糖-(1→3)-β-D-吡喃木糖-(1→4)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖苷，未见文献报道。鉴定的已知化合物分别为桔梗皂苷D(2)、菠菜甾醇(4)、Δ~7-豆甾烯醇(5)、胡萝卜苷(6)、正丁基-O-β-D-吡喃果糖苷(7)、甲基-O-α-D-呋喃果糖苷(8)、甲基-O-β-D-呋喃果糖苷(9)、D-果糖(10)、D-山梨醇(11)、5-羟甲基糠醛(12)、α-生育酚(13)、α-棕榈酸甘油酯(14)、L-谷氨酸(15)。所鉴定化合物中，化合物6～9、11～13均为首次自该属植物中分离得到。采用MTT法和细胞生长抑制计数法，分别对桔梗乙醇提取物及其不同溶剂萃取部位和分离得到的单体化合物进行了抗肿瘤活性筛选。实验结果表明化合物2具有抑制MCF-7和HL-60癌细胞的活性。其具体作用机制以及桔梗皂苷抗肿瘤活性的构效关系还有待进一步研究。更多还原

【Abstract】 The roots of Platycodon grandiflorum （Jacq.） A. DC. have been extensively used in TCM, called "Jiegeng" （Japanese name: Kikyo） for the treatment of cough and pectoral diseases. Although a lot of studies on chemistry and pharmacology of Platycodon were reported, the research on the antitumor principles of the medicine was not reported. In order to exploit the plant resource and find new antitumor compounds, the study on the constituents of Jiegeng was carried out.From the roots of Platycodon grandiflorum, 21 constituents were isolated by various chromatographic methods, such as silica gel C. C., Sephadex LH-20 C. C., MPLC and HPLC. On the basis of UV, IR, NMR, MS data, measurement of physico-chemical characters and chemical methods, the structures of 15 compounds were identified as 3 triterpenoid saponins, 3 steroids, 4 fructosides, 2 compounds with long chains, and 3 other types. Among them, a new natural compound is 3-O-β-laminari -biosyl-2β, 3β, 16α, 23-tetrahydroxyolean-12-ene-28-oic acid （1）. Compound 3 is determined as 3-O-β-D-xylopyranosyl-（1→4）-β-D-glucopyranosyl-2β,3β,16α-trihydro-xyolean-12-ene-28-oic acid 28-O-β-D-apiopyranosyl-（1→3）-β-D-xylopyranosyl-（1→4） -α-L-rhamnopyranosyl-（1→2）-α-L-arabinopyranoside, which has not been reported in the literature.The known compounds are platycodin D （2）, spinasterol （4）,Δ⁷-stigmasterol （5）, daucosterol （6）, n-butyl-O-β-D-fructopyranoside （7）, methyl-O-α-D-fructofuranoside （8）, methyl-O-β-D-fructofuranoside （9）, D-fructose （10）, D-glucitol （11）, 5-hydroxymethylfurfural （12）,α-tocopherol （13）, glycerylα-monopalmitate （14） and L-glutamic acid （15）. Among them, compound 6-9,11-13 were isolated from this genus for the first time.The ethanol extract and the petroleum ether, CHCl₃, EtOAc and n-BuOH fraction, the isolated compounds were tested for their inhibitory activity against MCF-7 and HL-60 tumor cell lines by MTT method. The compound 2 （Platycodin D） showed significant inhibition against the two tumor cells.更多还原