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A new indole glycoside from the seeds of Raphanus sativus

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Abstract

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 13 and 69, were isolated from this plant for the first time. The structures of compounds 19 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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Acknowledgments

This work was supported by a Grant (12172MFDS989) from the Ministry of Food and Drug Safety, Govt. of Republic of Korea in 2013–2014. We thank Dr. K. D. Park at the Korea Basic Science Institute for Gwangju Center for help in obtaining the NMR spectra.

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Correspondence to Eun-Rhan Woo.

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Hong-Guang Jin and Hae Ju Ko have equally contributed to this work.

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Jin, HG., Ko, H.J., Chowdhury, M.A. et al. A new indole glycoside from the seeds of Raphanus sativus . Arch. Pharm. Res. 39, 755–761 (2016). https://doi.org/10.1007/s12272-016-0758-0

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