三种虎皮楠属植物及石蒜生物碱成分研究
张于
学位类型博士
导师郝小江
2010-05
学位授予单位中国科学院研究生院
学位专业药物化学
摘要本论文以三种虎皮楠属植物,即西藏虎皮楠、脉叶虎皮楠及虎皮楠的枝叶及树干以及石蒜科植物红花石蒜的根茎为材料,对其生物碱成分进行了系统的研究。运用多种分离手段,结合现代波谱分析技术,从三种虎皮楠属植物及一种石蒜科植物中共分别分离鉴定了79个生物碱成分 (有72个不同结构的化合物),其中包括16个新虎皮楠生物碱,并有2个新骨架类型的虎皮楠生物碱。第一章 西藏虎皮楠 (Daphniphyllum himalense (Benth.) Mull.-Arg.) 中生物碱成分研究。从其叶子提取物的总碱部分分离鉴定了24个生物碱,其中有7个新化合物。化合物1 (daphhimalenine A) 为一个具有新颖重排骨架的虎皮楠生物碱。我们推测其生源上可能是通过从该种分离得到的 yuzurimine 类型化合物2 (daphhimalenine B) 及3 (daphnezomine T) 作为生源前体衍变而来。我们对其树干提取物的总碱部分进行了研究,共分离鉴定了7个生物碱。第二章 脉叶虎皮楠 (Daphniphyllum paxianum Rosenth.) 中生物碱成分研究。从其枝叶提取物的总碱部分分离鉴定了17个生物碱,其中有5个新化合物。化合物1 (paxiphylline A) 为具有新颖的 C-23 骨架 daphnicyclidin 类型生物碱。较之其他 C-22 骨架类型生物碱,其骨架上多余的一个碳单元从生源上可能是通过具有 daphnicyclidin H 骨架的前体化合物与甲醛发生 aldol condensation 所得到。第三章 虎皮楠 (Daphniphyllum oldhami Rosenth.) 中生物碱成分研究。从其叶子提取物的总碱部分分离鉴定了12个生物碱,其中有4个新化合物。化合物2 (dapholdhamine B) 为目前发现的第三例daphnezomine 类型的虎皮楠生物碱。 第四章 石蒜 (Lycoris radiata (L’ Her.) Herb.) 中生物碱成分研究。从购自昆明广德生物科技有限公司的石蒜根部提取物的总碱部分分离鉴定了19个生物碱,并对其抗 HBV 活性进行了筛选,研究发现苄基苯乙胺类生物碱多个亚类型成分具有较好的抑制 HBV DNA 复制的作用,同时开展了几类苄基苯乙胺生物碱结构修饰工作。第五章 从生物合成和全合成角度,综述了经典的 Mannich 反应在萜类生物碱,如以单萜吲哚生物碱为代表的真生物碱、以二萜生物碱为代表的伪生物碱,以及以虎皮楠生物碱为代表的非经典生物碱中构建骨架的应用实例。
资助项目This thesis elaborated the studies on the alkaloids from three Daphniphyllum species, the leaves and twigs of Daphniphyllum himalense (Benth.) Mull.-Arg., Daphniphyllum paxianum Rosenth., and Daphniphyllum oldhami Rosenth.  along with alkaloids from root-stems of Lycoris radiate. Seventy-nine alkaloids were acquired totally from those four plants by variety of chromatographies over various materials, and their structures were identified by spectroscopic data analysis. Among them, sixteen Daphniphyllum alkaloids were new ones, including two novel ones with unprecedented skeleton.Chapter 1 Alkaloids from Daphniphyllum himalense (Benth.) Mull.-Arg.Twenty-four alkaloids, including seven new Daphniphyllum alkaloids were isolated and elucidated from the leaves of D. himalense (Benth.) Mull.-Arg. Among the seven new alkaloids, compound 1 (daphhimalenine A) was a novel one with rearranged skeleton. Biogenetically, compound 1 may originated from the two yuzurimine-type alkaloids, 2 (daphhimalenine B) and 3 (daphnezomine T), which were also isolated from the same plants. Seven alkaloids were also isolated and identified from the twigs of D. himalense (Benth.) Mull.-Arg.Chapter 2  Alkaloids from Daphniphyllum paxianum Rosenth.Investigation of alkaloid constituents of the leaves and twigs of Daphniphyllum paxianum Rosenth. has resulted in the isolation of seventeen alkaloids. And five were new ones. Among them, compound 1 (paxiphylline A) was a novel Daphniphyllum alkaloid with an unprecedented additional carbon daphnicyclidin skeleton. From a biogenetic perspective, the “extra” carbon unit may be provided by formaldehyde through aldol condensation.Chapter 3  Alkaloids from Daphniphyllum oldhami Rosenth.In this work, twelve alkaloids, including four new ones, were isolated and elucidated from the leaves of Daphniphyllum oldhami Rosenth. Among them, compound 2 (dapholdhamine B) was the third daphnezomine types of Daphniphyllum alkaloid till now.Chapter 4  Alkaloids from Lycoris radiate.Nineteen alkaloids were isolated and elucidated from rough alkaloids of the root-stems of Lycoris radiate, which was bought from Guangde Bio-tech Ltd of Kunming. The inhibition activities against HBV of these alkaloids were evaluated which indicated that some subclass of benzylphenethylamine alkaloids has high inhibition activities against DNA replication of HBV. Meanwhile, structural modification of several types of benzylphenethylamine alkaloids were in progress.Chapter 5  Review.Advances research of Mannich-like reactions in terpenoids alkaloids, including monoterpenoid indole alkaloids as the “true alkaloids”, diterpenoid alkaloids as the “pseudo alkaloids”, and the Daphniphyllum alkaloids as the “unusal alkaloids” from biosynthetic and total synthesis point of view was reviewed.
语种中文
文献类型学位论文
条目标识符http://ir.kib.ac.cn/handle/151853/16022
专题昆明植物所硕博研究生毕业学位论文
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张于. 三种虎皮楠属植物及石蒜生物碱成分研究[D]. 中国科学院研究生院,2010.
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