title: A new indole glycoside from the seeds of Raphanus sativus.
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 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 (1)H-(1)H 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.
authors.affiliation: College of Pharmacy and Life Science, Jiu Jiang University, 320 Xun Yang Road, Jiujiang, 33200, China.
authors.forename: Hong-Guang
authors.initials: HG
authors.lastname: Jin
authors.affiliation: College of Pharmacy, Chosun University, 309 Pilmun-daero, Dong-gu, Gwangju, 501-759, Republic of Korea.
authors.forename: Hae Ju
authors.initials: HJ
authors.lastname: Ko
authors.affiliation: College of Pharmacy, Chosun University, 309 Pilmun-daero, Dong-gu, Gwangju, 501-759, Republic of Korea.
authors.forename: Md Anisuzzaman
authors.initials: MA
authors.lastname: Chowdhury
authors.affiliation: College of Pharmacy, Chosun University, 309 Pilmun-daero, Dong-gu, Gwangju, 501-759, Republic of Korea.
authors.forename: Dong-Sung
authors.initials: DS
authors.lastname: Lee
authors.affiliation: College of Pharmacy, Chosun University, 309 Pilmun-daero, Dong-gu, Gwangju, 501-759, Republic of Korea. wooer@chosun.ac.kr.
authors.forename: Eun-Rhan
authors.initials: ER
authors.lastname: Woo
mesh_terms: D000893:Anti-Inflammatory Agents / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D055808:Drug Discovery / Q000379:methods*; D004797:Enzyme-Linked Immunosorbent Assay; D006027:Glycosides / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000302:isolation & purification* / Q000494:pharmacology; D015850:Interleukin-6 / Q000096:biosynthesis*; D015394:Molecular Structure; D031224:Raphanus / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D014409:Tumor Necrosis Factor-alpha / Q000494:pharmacology
chemical_list: D000893:Anti-Inflammatory Agents; D006027:Glycosides; D007211:Indoles; D015850:Interleukin-6; D014409:Tumor Necrosis Factor-alpha
keywords: Brassicaceae; IL-6 inhibitory effect; Indole glycoside; Raphanus sativus