Study On The Total Synthesis And Bioactivities Of Syringaresinol And Glycosides

Syringaresinol is an important bioactive constituent in many medicine-used plants. It is reported that Syringaresinol and its glucosides have the activity of antioxidants, antidepressant, anti-inflammation, inhibition of gastric ulcer, selective cytotoxin, promotion of the neurite outgrowth and the ability of stimulating T and B lymphocyte proliferation, and inhibiting some enzyme. From these reports, we knew that the bioactivities of Syringaresinol and its single glucoside or double glucosides are not the same. Even if the same aglycone is connected to different saccharides, the produced glycosides had very different bioactivities. To get some compounds that have certain activity, we planned to modify Syringaresinol, connect different glycosyl donors, separate (+)- and (-)-Syringaresinol glycosides, and do high-throughput-screening on those compounds.Firstly, the methods of isolating (+)-Syringaresinol from Eucommia ulmoides Oliv. were discussed, and other furfuran lignans were also isolated. Then a RP-HPLC method was established for the determination of the total content of Syringaresinol and its glycosides in plants. Secondly, for the purpose of the structure modification and the bioactivity researches on Syringaresinol and its glycosides, we studied on the total synthesis. A total synthesis of Syringaresinol was established, increased the yields. At the same time, a structure-analog of Syringaresinol: Dehydrodisinapinsatedilactone was also synthesized. Acetyl Syringaresinol and acetyl Dehydrodisinapinsatedilactone have been got yet.In the studies of synthesizing Syringaresinol glycosides, several compounds we have been got as follows: Syringaresinol-4-O-D-tetriacetyl glucoside,...