Studies On The Chemical Constituents And Their Bioactivities From Smilax Riparia

Smilax riparia A. DC. belongs to Liliaceae, which is the folk herb of Hubei province. The roots of S. riparia have been used in preventing sore throat, bruises in clinic. It also has the properties of treating rheumatoid arthritis, bones and muscles ached, lumbar muscle strain and so on. So far, only3papers with chemical and pharmacological research of S. riparia have been reported, including phenolic compounds and steroid saponins. In addition, steroid saponins revealed significant anti-inflammatory effect and the95%EtOH extract of S. riparia exhibited significant anti-tumor activity.In order to search the bioactive constituents from natural source, we began to study the chemical consitituents from S. riparia. By repeated column chromatography, including silica gel, toyopearl HW-40and preparative HPLC,27compounds were isolated from95%EtOH extract of S. riparia. By analysis of IR, MS,1D and2D NMR spectra, the structures of isolated compounds were identified as follows:(Z)-6-hydroxy-4,5-dimethoxy-2-(3,4,5-trimethoxybenzylidene)benzofuran-3(2H)-one (1),26-O-(3-D-glucopyranosyl-(25S)-5α-furostane-20(22)-en-3β,26-diol-3-O-α-L-rhamnopyranosyl-(1â†'2)-[α-L-rhamnopyranosyl-(1â†'6)]-α-D-glucopyranoside (2),5β-(6,7-dihydroxyethyl)-4-(5’-hydroxymethyl-furan-2-ylmethylene)-2α-methoxy-dihydrofuran-3-one (3),5α-(6,7-dihydroxyethyl)-4-(5’-hydroxymethyl-furan-2-ylmethylene)-2a-methoxy-dihydrofuran-3-one (4),(1R,2R,4S)-trans-2-hydroxy-1,8-cineole-β-D-glucopyranoside (5), zansimuloside A (6), loganin (7), paederosidicacid (8),4-[Formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoate (9),5-methoxy-[6]-gingerol (10), dehydroabietic acid (11), pteryxin (12),2-methyphenyl-1-O-β-D-glucopyranosid (13),3,5-dimethoxy-4-hydroxybenzonic acid (14), isovanillin (15), vanillic acid (16),p-hydroxy cinnamic acid (17), p-hydroxy cinnamic methyl ester (18),p-hydroxybenzaldehyde (19), ferulic acid methyl ester (20), benzoic acid (21),5-hydroxymethyl-2-furalclehyde (22), stigmast-5-en-3β-ol-7-one (23),3β-hydroxy-stigmast-5,22-dien-7-one (24),β-sitosterol (25), stigmasterol (26),(3-daucosterol (27). Compoune1was new which didn’t be reported any more, and compounds3-13,17-21and23-24were isolated from this genus for the first time.MTT method was used to determine the non-cytotoxic concentrations for the isolated compounds. Then transwell chemotaxis experiment was used to evaluate the role of inhibiting tumor cell migration. Compounds3,4and22showed significant inhibition effect on tumor cell migration. The value of inhibition rate on MDA-MB-231was65.7%at the concentration of0.8μg/ml of compound22.In this paper, skeletal muscle cells L6GLUT4myc were used to evaluate anti-daibetic activity of isolated compounds. Class ELISA double antibody clip method was used to evaluate the role of ehancing GLUT4translocation. Compounds3,4and8showed significant effect on ehancing GLUT4translocation. The multiple value of translocation on skeletal muscle cells GLUT4myc was1.52at the concentration of20.0μmol/L of3.In a screen for antioxidants from the extract of S. riparia, compounds10and14-20showed significant antioxidant activities, and compound14revealed DPPH free radical scavenging rate with85.9%.