Knowledge Management System of Kunming Institute of Botany,CAS
| 翼梗五味子次生代谢产物的化学研究; Chemical Studies on the Secondary Metabolites from Schisandra henryi | |
| 何桃斌 | |
| Thesis Advisor | 孙汉董 |
| Abstract | Abstract The Schisandraceae family contains two genera, Kadsura and Schisandra. There are abundant resources and about 30 species of Schisandraceae plants in China. Many species of this family have been used in folk medicine by virtue of their nourishing and tranquilizing effects. Diverse secondary metabolites have been found from this family, such as triterpenoids, lignans, sesquiterpenoids, and flavonoids. Among them, triterpenoids can be classified into lanostane-type, cycloartane-type, and schinortriterpenoids. Schinortriterpenoids are a class of natural products exclusively found in the species of this family, and mainly isolated from the Schisandra genus. The structurally intricate and diverse schinortriterpenoids have aroused widespread attentions from the phytochemical, organic synthetic, and quantum chemical research communities. This dissertation is composed of three chapters. Chapter 1 described the research on chemical constituents and their bioactivities of Schisandra henryi. 120 compounds, including 30 new ones, were isolated from this species, and their structures were established based on the extensive spectroscopic methods and single-crystal X-ray diffraction. Chapter 2 described the studies on the biomimetic total synthesis of five sesquiterpene dimers, henryinins A–E (1–5). Chapter 3 reviewed the progress in the application of the Diels-Alder reaction in the synthesis of natural terpenoids. Chapter 1. Studies on the chemical constituents of Schisandra henryi and their bioactivities Schisandra henryi is a woody vine mainly distributed in Southern China. Phytochemical studies on the 70% aqueous acetone extract of this plant by us led to the discovery of 120 compounds, of which 30 were new ones. These compounds involved triterpenoids, lignans, sesquiterpenoids, sesquiterpene dimers and phenylpropanoids. Notably, henryinins A–E (1–5), five novel sesquiterpene dimers featuring five fused 6-memebered rings and bicyclo [2,2,2] octane-bridged motif were obtained. From a biosynthetic view, they were plausibly formed by the Diel-Alder reaction of cadinene sesquiterpene units. Among all the isolates, 56 schinortriterpenoids, including 13 new ones, were isolated and their structures involved in seven skeletons: schisanartane, 18-norschiartane, preschisanartane, schiartane, 18(13→14) abeoschiartane, lancishiartane and 12,22-cyclopreschisanartane. Among them, henridilactone R (19), an 18-norschiartane-type, was found to be transformed into wuweizidilactone B and wuweizidilactone W at room temperature. From a biosynthetic view, henridilactone R may be an important intermediate of 18-norschiartane-type schinortriterpenoids. As for the biological activities of all isolates, five sesquiterpenoid dimers, henryinins A–E (1–5), were tested for their immunosuppression, tumor immunotherapy, cytotoxicity against five tumor cells, effects on the calcium and sodium channels, hearing protective and hypoglycemic activities. As a result, henryinin C (3) |
| 2020-11 | |
| Document Type | 学位论文 |
| Identifier | http://ir.kib.ac.cn/handle/151853/74243 |
| Collection | 昆明植物所硕博研究生毕业学位论文 |
| Recommended Citation GB/T 7714 | 何桃斌. 翼梗五味子次生代谢产物的化学研究, Chemical Studies on the Secondary Metabolites from Schisandra henryi[D],2020. |
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| File Name/Size | DocType | Version | Access | License | ||
| 何桃斌-博士学位论文-何桃斌1203cc（9495KB） | 学位论文 | 限制开放 | CC BY-NC-SA | Application Full Text | ||
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