Coriaria Chemical Composition Studies And Ursolic Acid Glucoside Synthesis

1. Studies of the components of Coriaria sinica MaximCoriaria sinica Maxim is a bush of Coriaria L. Eight flavonal compounds were isolated from the leaves of Coriaria sinica Maxim by using various chromatogram and were elucidated by NMR, MS, IR, et al. The structural of the compounds were: Kaempferol (1), Kaempferol-3-O-α-L-rhamnoside (2), Kaempferol-3-O-β-D-galacto-side (3), Kaempferol-3-O-α-L-arabinoside (4), Quercetin (5), Quercetin-3-O-α-L-arabinoside (6), Quercetin-3-O-β-D-galactoside (7), Quercetin-3-O-β-D-glucoside (8). Four compounds were isolated from this plant for the first time, which were (2), (3), (4),(6).Five terpenoids were isolated from the leaves, fruits, seeds of Coriaria sinica Maxim, which were ursolic acid (9), Oleanolic acid (10), Actylkamebakaurinin (11), Coriatin (12), Tutin (13). Compound (10) and (11) were firstly isolated from the plant.Ursolic acid as the standard, 5% vanillin-acetic acid and perchloric acid as the developer, used the ultraviolet spectrophotometnc method to determine the content of the tritepenoidic acid in the leaves of Coriaria sinica Maxim.2. Synthesis of the saponins of ursolic acidUrsolic acid is a pentacyclic triterpene. The ursolic acid saponins bearing 4-chloro-4-deoxy-β-D-galactopyranose at C-3 and C-28 position of ursolic acid were designed and synthesized. In the study, an interesting fact was found: the dilute hydrochloric acid could selectively hydrolyze the acetyl group at the different position of the sugar moieties. The saponins of ursolic acid were obtained, which remained acetyl group in the C-2 of the sugar. In order to explain this fact, 3-hydroxyl ursolic acid-28-O-(2", 3", 4", 6"-tert-O-acetyl-β-D-galactopyranosyl) ester and o-nitro phenol-(2', 3', 6'-tri-acetyl-O-4-chloro-4-deoxy-β-D-galactopyranosyl) were also synthesized. Then hydroly- zed by the 0.1 mol/L diluted hydrochloric acid, 3-hydroxyl ursolic acid-28-O-(2", 3", 4", 6"-tert-O-acetyl-β-D-galactopyranosyl) ester formed a mixture of deacetylated compounds, but no all deacetylated compounds were obtained.