Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities.

Abstract

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.

• Authors: Jing Zhao, Norio Nakamura, Masao Hattori, Tomoharu Kuboyama, Chihiro Tohda, Katsuko Komatsu
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 50 Issue 6 Pg. 760-5 (Jun 2002) ISSN: 0009-2363 [Print] Japan
• PMID: 12045329 (Publication Type: Journal Article)

Chemical References

• 3-rhamnopyranosyl(1-4)-glucopyranosyl-12-diacetoxy-20-hydroxywitha-5,24-dienolide
• Disaccharides
• Lactones
• Withanolides
• Ergosterol

Topics

• Disaccharides (chemistry, pharmacology)
• Ergosterol (analogs & derivatives)
• Humans
• Lactones (chemistry, pharmacology)
• Neurites (drug effects)
• Plant Roots (chemistry)
• Solanaceae (chemistry)
• Tumor Cells, Cultured
• Withanolides