Stilbene Glycoside Compounds Synthesized Research

Salvianolic acids, the main active ingredients of Danshen-Radix Salviae Miltiorrhizae which has been used clinically as a common traditional Chinese medicine in the treatment of cardiovascular diseases, possess biological activities such as antilipidperoxide, scavenging effects on free radicals, modulation of PGI₂/TXA₂ balance in myocardial ischemia, calcium antagonist, activation of potassium channel (K_atp).Salvianolic acids are a kind of compounds usually having a hydroxystilbenoid moiety. In order to investigate the structure-activity relationship, we designed and synthesized several hydroxystilbene derivatives. Their anti-myocardial ischemia activity will be investigated. We designed the glycoside derivatives of those hydroxystilbenes to improve their physicochemistry property.Three of hydroxystilbenoids were synthesized by reductive elimination of 1, 2-diarylethan-1-ones which were the products of phenolic ester's Fries rearrangement reaction. They are (E)-4-hydroxysilbene, (E)-4-hydroxy-3-methylstilbene andα,β-dihydro-2-methyl-4-hydroxystilbene. Another compound, (E)-4-hydroxy-4'-methoxystilbene, was synthesized by Perkin reaction. We choose 1-O-acetyl sugars as glycosyl donors in the glycosylation reaction. 10 stilbenoids glycosides were synthesized by reacting hydroxystilbenes withβ-D-glucose pentaacetate,β-D-galactose pentaacetate orβ-D-lactose octaacetate with phosphorus oxychloride as a catalyst. All the glycoside compounds were characterized by ¹H NMR and ESI/MS.Now we are taking biological evaluation of the compounds we synthesized.