title: Three new lignan glycosides with IL-6 inhibitory activity from Akebia quinata.
abstract: Three new lignan glycosides, akeqintoside A [(7S,8S)-7,8-dihydro-8-hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1'-benzofuranpropanol 2'-O-β-D-glucopyranoside] (1), akeqintoside B [(7R,8R)-7,8-dihydro-8-hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1'-(9'-methoxy-7'-propenyl) benzofuran 2'-O-β-D-glucopyranoside] (2), and akequintoside C [7R*,8R*-dihydroxy-7-(4-hydroxy-3-methoxyphenyl)-glycerol 9-O-β-D-(6'-O-caffeoyl)-glucopyranoside] (3) were isolated from Akebia quinata along with five known compounds, syringin (4), vanilloloside (5), salidroside (6), 3,4-dihydroxyphenylethyl alcohol 8-O-β-D-glucopyranoside (7), and calceolarioside B (8). The structures of the compounds were identified based on one dimensional (1D)- and 2D-NMR, including (1)H-(1)H correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and nuclear Overhauser effect spectroscopy (NOESY) spectroscopic analyses. The inhibitory activity of these isolated compounds against interleukin-6 (IL-6) production in tumor necrosis factor-alpha (TNF-α) stimulated MG-63 cells was also examined.
authors.affiliation: College of Pharmacy, Chosun University.
authors.forename: Hong-Guang
authors.initials: HG
authors.lastname: Jin
authors.forename: A Ryun
authors.initials: AR
authors.lastname: Kim
authors.forename: Hae Ju
authors.initials: HJ
authors.lastname: Ko
authors.forename: Sang Kook
authors.initials: SK
authors.lastname: Lee
authors.forename: Eun-Rhan
authors.initials: ER
authors.lastname: Woo
mesh_terms: D002109:Caffeic Acids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002478:Cells, Cultured; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D019684:Magnoliopsida / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010666:Phenylpropionates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014409:Tumor Necrosis Factor-alpha / Q000494:pharmacology; D000093242:Interleukin-6 Inhibitors
chemical_list: D002109:Caffeic Acids; D004365:Drugs, Chinese Herbal; D005960:Glucosides; D006027:Glycosides; D017705:Lignans; D010636:Phenols; D010666:Phenylpropionates; D014409:Tumor Necrosis Factor-alpha; D000093242:Interleukin-6 Inhibitors; C529019:calceolarioside B; C028305:syringin; C009172:rhodioloside