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Anti-inflammatory and Antiosteoporosis Flavonoids from the Rhizomes of Helminthostachys zeylanica.

Authors :
Huang YL
Shen CC
Shen YC
Chiou WF
Chen CC
Source :
Journal of natural products [J Nat Prod] 2017 Feb 24; Vol. 80 (2), pp. 246-253. Date of Electronic Publication: 2017 Feb 07.
Publication Year :
2017

Abstract

Chemical investigation of the rhizomes of Helminthostachys zeylanica led to the isolation of eight new flavonoids including six cyclized geranylflavonoids, ugonins V-X (1-3), (10R,11S)-ugonin N (4), (10R,11S)-ugonin S (5), and ugonin Y (6), as well as two quercetin glucosides, quercetin-4'-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (7) and quercetin-3-O-β-d-glucopyranosyl-4'-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (8). The structures of these compounds were established by spectroscopic analyses and acid hydrolysis of the sugar moiety. Among the isolated compounds, 1, 2, 5, 6, ugonins J-S (9-13), ugonstilbene A (14), and ugonin L (23) were evaluated for their anti-inflammatory activity on lipopolysaccharide-induced nitric oxide (NO) production in microglial cells. Except for 1, 5, and 13, all other compounds inhibited NO production with IC <subscript>50</subscript> values of 6.2-10.1 μM and were more potent than the positive control, pyrrolidine dithiocarbamate. Compounds 1, 2, 5, 6, and 10-13 were tested for antiosteoporotic activities, and ugonin K (10) exhibited the highest inhibitory activity against RANKL-induced osteoclast differentiation in RAW264.7 cells with an IC <subscript>50</subscript> value of 1.8 ± 0.2 μM.

Details

Language :
English
ISSN :
1520-6025
Volume :
80
Issue :
2
Database :
MEDLINE
Journal :
Journal of natural products
Publication Type :
Academic Journal
Accession number :
28169537
Full Text :
https://doi.org/10.1021/acs.jnatprod.5b01164