皂苷类衍生物的制备及分析
关键词 知母皂苷、菝葜苷元、异菝葜苷元、结构修饰、葡萄糖糖基化
毕业论文设计说明书外文摘要
Title The synthesis and analysis of saponins derivatives
Abstract
Rhizoma Anemarrhenae, a kind of traditional medicine, is the dry rhizome of Liliaceae plant of Anemarrhena asphodeloides Bunge. With the good effect of clearing heat-fire and embellishing, it is usually used to cure exogenous fever, high fever polydipsia, hyperactivity dry cough, constipation and other symptoms. Saponins are the main components of Rhizoma Anemarrhenae, including Timosaponin A-Ⅰ, A-Ⅱ, A-Ⅲ, A-Ⅳ, B-Ⅰ, B-Ⅱ. In this paper, Sarsasapogenin and Isosarsasapogenin were fisrstly obtained by the acid hydrolysis of Timosaponins (including Timosaponin B-II and B-III, etc), and then two derivates were synthesized by their C-3 positions linked to a glucosyl group. All products were isolated and purified by column chromatography and recrystallization, and their structures were further identified by 1H-NMR, 13C-NMR. Moreover, their purities were determined by High Performance Liquid Chromatography (HPLC).
Keywords Timosaponins; sarsasapogenin; Isosarsasapogenin; Structure modification; Glucose glycosylation
目 次
1 引言 1
2 皂苷类化合物 2
2.1 概述 2
2.2 知母皂苷 2
2.3 苷元主要制备方法 3
3 糖类化合物 5
3.1 概述 5
3.2 糖类化合物在药学中的应用 5
3.3 单糖的结构特征 6
3.4 糖合成中羟基的保护与脱保护 6
4 糖苷化合成路线的选择 8
5 实验部分 9
5.1 仪器与试剂 9
5.2 菝葜苷元与异苷元的制备 9
5.3 活性单糖给体的制备 10
5.4 苷元葡萄糖糖基化衍生物的合成 11
6 结果与讨论 13
6.1 结果 13
6.2 菝葜苷元与异苷元核磁共振谱讨论 14
6.3 3-位糖苷键连接方式的讨论 15
6.4 影响苯甲酰基保护的单糖三氯乙酰亚氨酯收率的因素 16
结论 17
致谢 18
参考文献 19
附录 谱图 21
1 引言
皂苷类成分广泛存在于植物界和中草药中，是一类十分重要的天然产物，具有治疗心脑血管疾病、糖尿病和高血脂等药效作用。皂苷类化合物主要包括三萜类化合物和螺旋甾烷类化合物两种。其中，螺旋甾烷类化合物又称为甾体皂苷，主要存在于薯蓣科、百合科和玄参科等植物中[1]。
知母是一种传统中药，中国药典[2]收载的知母为百合科植物知母Anemarrhena asphodgfoides Bge.的干燥根茎，具有清热泻火、滋阴润燥的功效，临床上常用来治疗外感热病、高热烦渴、肺热燥咳、肠燥便秘等症状。知母中的主要活性成分为知母皂苷，约占药材含量的6%~9%。市售的知母皂苷通常由知母药材经过浸提水解得到的总皂苷精制而成，主要包括知母皂苷A-Ⅰ、A-Ⅱ、A-Ⅲ、A-Ⅳ、B-Ⅰ、B-Ⅱ，其中知母皂苷B-Ⅱ含量较多[3] 。近年来越来越多的研究人员开始关注知母皂苷的活性问题，文献报道称知母皂苷在改善老年性痴呆、抗动脉粥样硬化、抗血小板聚集、降脂、抗炎等方面有显著的功效，同时在改善骨质疏松、抗氧化、抗辐射、抗癌等方面也有作用[4]。