Anti-inflammatory and Antiosteoporosis Flavonoids from the Rhizomes of Helminthostachys zeylanica.
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 IC50values 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 IC50value of 1.8 ± 0.2 μM.
National Research Institute of Chinese Medicine, Ministry of Health and Welfare , No. 155-1, Sec. 2, Li-Nung Street, Peitou, Taipei 11221, Taiwan.|Department of Cosmetic Science, Chang Gung University of Science and Technology , Taoyuan 33302, Taiwan.
Yu-Ling
0000-0001-9914-1716
YL
Huang
National Research Institute of Chinese Medicine, Ministry of Health and Welfare , No. 155-1, Sec. 2, Li-Nung Street, Peitou, Taipei 11221, Taiwan.
Chien-Chang
CC
Shen
National Research Institute of Chinese Medicine, Ministry of Health and Welfare , No. 155-1, Sec. 2, Li-Nung Street, Peitou, Taipei 11221, Taiwan.|Institute of Biomedical Sciences, National Chung-Hsing University , Taichung 40227, Taiwan.|National Taipei University of Nursing and Health Science , Taipei, Taiwan.
Yuh-Chiang
YC
Shen
National Research Institute of Chinese Medicine, Ministry of Health and Welfare , No. 155-1, Sec. 2, Li-Nung Street, Peitou, Taipei 11221, Taiwan.
Wen-Fei
WF
Chiou
Department of Biotechnology, Hungkuang University , Taichung 433, Taiwan.
Chien-Chih
CC
Chen
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D029624:Ferns / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005960:Glucosides / Q000032:analysis; D008070:Lipopolysaccharides / Q000494:pharmacology; D019684:Magnoliopsida / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D010024:Osteoporosis / Q000188:drug therapy*; D011794:Quercetin / Q000494:pharmacology; D000067996:RAW 264.7 Cells / Q000187:drug effects; D027343:Rhizome / Q000737:chemistry*; D013624:Taiwan
D000894:Anti-Inflammatory Agents, Non-Steroidal; D005419:Flavonoids; D005960:Glucosides; D008070:Lipopolysaccharides; C540912:ugonin K; D009569:Nitric Oxide; D011794:Quercetin