三种萝藦科植物的化学成分研究
其他题名STUDIES ON THE CHEMICAL CONSTITUENTS FROM THREE SPECIES OF ASCLEPIADACEAE
高竹林
学位类型博士
导师郝小江
2008-05-28
学位授予单位中国科学院昆明植物研究所
学位授予地点昆明植物研究所
学位专业植物学
关键词萝藦科 乳突果 蓝叶藤 古钩藤 C-21甾体苷
摘要本论文对三种萝藦科植物:乳突果(Adelostemma gracillimum Hooker)、蓝叶藤(Marsdenia tinctoria R.Br.)和古钩藤(Cryptolepis buchananii Roem. et Schult.)中的化学成分进行了系统研究。应用硅胶柱层析、反相(RP-18)柱层析、葡聚糖凝胶(Sephadex LH-20)柱层析和半制备HPLC等多种分离材料和分离技术,结合现代波谱分析方法和化学方法,从以上三种植物中分离并鉴定了50个化合物(从各种植物中重复分离到的未计入),其中新化合物16个。化合物的结构类型涉及C-21甾体及其苷、木脂素、三萜、酚性化合物、联苯类、鞘胺醇类等。新化合物的结构如下: 一、乳突果苷元3-β-D-葡萄吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖苷(1); 二、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖苷(2); 三、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖苷(3); 四、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-α-L-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-α-L-磁麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖苷(4); 五、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(5); 六、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(6); 七、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-葡萄吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(7); 八、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-葡萄吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(8); 九、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-葡萄吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖苷(9); 十、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-葡萄吡喃糖基-(1→4)-α-L-磁麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖苷(10); 十一、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-葡萄吡喃糖基-(1→4)-α-L-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-α-L-磁麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖苷(11); 十二、乳突果苷元3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-葡萄吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-α-L-磁麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖苷(12); 十三、cynanchone A 的碳酸甲酯衍生物(13); 十四、12-O-乙酰基-20-O-(N-甲基)-邻氨基苯甲酰基肉珊瑚苷元3-O-6-去氧-3-O-甲基-β-D-阿洛吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(25); 十五、12-O-乙酰基-20-O-(N-甲基)-邻氨基苯甲酰基肉珊瑚苷元3-O-6-去氧-3-O-甲基-β-D-阿洛吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(26); 十六、12-O-乙酰基-20-O-(N-甲基)-邻氨基苯甲酰基肉珊瑚苷元3-O-β-D-葡萄吡喃糖基-(1→4)-6-去氧-3-O-甲基-β-D-阿洛吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-磁麻吡喃糖苷(27)。 最后,综述了1990-2008年间发表的萝藦科植物中的裂环C-21甾体及其苷。
其他摘要This thesis elaborated the studies on the chemical constituents from three species of Asclepiadaceae: Adelostemma gracillimum Hooker, Marsdenia tinctoria R. Br. and Cryptolepis buchananii Roem.et Schult. From the above plants, totally 50 compounds were isolated by the various chromatographies over silica gel column, reverse phase column (RP-18), Sephadex LH-20, semi-pre HPLC and so on. Among them, there are 16 new compounds. On the basis of chemical evidences and extensive spectroscopic methods, including one-dimensional and two-dimensional NMR, the structures of 16 new compounds were established as: (I) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-digitoxopyranoside (1), (II) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyanosyl-(1→4)-β-D-digitoxopyranoside (2), (III) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-digitoxopyranoside (3), (IV) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl -(1→4)-β-D-digitoxopyranoside (4), (V) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside (5), (VI) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl (1→4)-β-D-cymaropyranoside (6), (VII) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside (7), (VIII) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl -(1→4)-β-D-cymaropyranoside (8), (IX) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-digitoxopyranoside (9), (X) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-digitoxopyranoside (10), (XI) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-digitoxopyranoside (11), (XII) gracigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-digitoxopyranoside (12), (XIII) 2,3-diacetyl-2,6,6-trihydroxybiphenyl-3-yl methyl carbonate (13), (XIV) prosapogenin 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl -(1→4)-β-D-cymaropyranoside (25), (XV) prosapogenin 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (26), (XVI) prosapogenin 3-O-β-D-glucopyranosyl-(1→4)-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside(27), respectively. Finally, a review was summarized on C-21 seco-streoides and C-21 seco-steroidal glycosides from Ascepiadaceae reported during 1990-2008.
页数153
语种中文
文献类型学位论文
条目标识符http://ir.kib.ac.cn/handle/151853/188
专题昆明植物所硕博研究生毕业学位论文
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高竹林. 三种萝藦科植物的化学成分研究[D]. 昆明植物研究所. 中国科学院昆明植物研究所,2008.
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