Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities.
Five new withanolide derivatives (1, 9-12) were isolated from the roots of Withania somnifera together with fourteen known compounds (2-8, 13-19). On the basis of spectroscopic and physiochemical evidence, compounds 1 and 9-12 were determined to be (20S,22R)-3 alpha,6 alpha-epoxy-4 beta,5 beta,27-trihydroxy-1-oxowitha-24-enolide (1), 27-O-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside (withanoside VIII, 9), 27-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside (withanoside IX, 10), 27-O-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranoside (withanoside X, 11), and (20R,22R)-1 alpha,3 beta,20,27-tetrahydroxywitha-5,24-dienolide 3-O-beta-D-glucopyranoside (withanoside XI, 12). Of the isolated compounds, 1, withanolide A (2), (20S,22R)-4 beta,5 beta,6 alpha,27-tetrahydroxy-1-oxowitha-2,24-dienolide (6), withanoside IV (14), withanoside VI (15) and coagulin Q (16) showed significant neurite outgrowth activity at a concentration of 1 microM on a human neuroblastoma SH-SY5Y cell line.
Zhao
Jing
J
Department of Metabolic Engineering, Toyama Medical and Pharmaceutical University, Sugitani, Japan.
Nakamura
Norio
N
Hattori
Masao
M
Kuboyama
Tomoharu
T
Tohda
Chihiro
C
Komatsu
Katsuko
K
D004187:Disaccharides / Q000737:chemistry / Q000494:pharmacology*; D004875:Ergosterol / Q000031:analogs & derivatives*; D006801:Humans; D007783:Lactones / Q000737:chemistry / Q000494:pharmacology*; D016501:Neurites / Q000187:drug effects*; D018517:Plant Roots / Q000737:chemistry; D019657:Solanaceae / Q000737:chemistry*; D014407:Tumor Cells, Cultured; D054358:Withanolides
C433551:3-rhamnopyranosyl(1-4)-glucopyranosyl-12-diacetoxy-20-hydroxywitha-5,24-dienolide; D004187:Disaccharides; D007783:Lactones; D054358:Withanolides; D004875:Ergosterol