Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
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Three New Lignan Glycosides with IL-6 Inhibitory Activity from Akebia quinata
Hong-Guang JinA Ryun KimHae Ju KoSang Kook LeeEun-Rhan Woo
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2014 Volume 62 Issue 3 Pages 288-293

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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 1H–1H 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.

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© 2014 The Pharmaceutical Society of Japan
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