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KMID : 0043320160390060755
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Archives of Pharmacal Research
2016 Volume.39 No. 6 p.755 ~ p.761
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A new indole glycoside from the seeds of Raphanus sativus
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Jin Hong Guang
Ko Hae-Ju
Chowdhury Anisuzzaman
Lee Dong-Sung
Woo Eun-Rhan
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Abstract
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A new indole glycoside, β-d-glucopyranosyl 2-(methylthio)-1H-indole-3-carboxylate, named raphanuside A (1), as well as eight known compounds, β-d-fructofuranosyl-(2 → 1)-(6-O-sinapoyl)-α-d-glucopyranoside (2), (3-O-sinapoyl)-β-d-fructofuranosyl-(2 → 1)-α-d-glucopyranoside (3), (3-O-sinapoyl)-β-d-fructofuranosyl-(2 → 1)-(6-O-sinapoyl)-α-d-glucopyranoside (4), (3,4-O-disinapoyl)-β-d-fructofuranosyl-(2 → 1)-(6-O-sinapoyl)-α-d-glucopyranoside (5), isorhamnetin 3,4′-di-O-β-d-glucoside (6), isorhamnetin 3-O-β-d-glucoside-7-O-α-l-rhamnoside (7), isorhamnetin 3-O-β-d-glucoside (8) and 3'-O-methyl-(?)-epicatechin 7-O-β-d-glucoside (9) were isolated from the seeds of Raphanus sativus. Furthermore, compounds 1?3 and 6?9, were isolated from this plant for the first time. The structures of compounds 1?9 were identified using 1D and 2D NMR, including 1H?1H COSY, HSQC, HMBC and NOESY spectroscopic analyses. The inhibitory activity of these isolated compounds against interleukin-6 (IL-6) production in TNF-α stimulated MG-63 cells was also examined.
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KEYWORD
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Indole glycoside, IL-6 inhibitory effect, Brassicaceae, Raphanus sativus
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