lignans and liriodendrin

To investigate the chemical constituents of the flowers of Chrysanthemum indicum.. The chemical constituents were isolated by various column chromatographic methods. The structures were identified by spectral data.. Twelve compounds were isolated and identified as acacetin (1), tricin (2), 2',4'-dihydroxychalcone(3), 5-hydroxy-4',7-dimethoxyflavon(4),7hydroxyflavonone (5), isorhamnetin (6),5,6,7-trihydroxy- 3',4', 5'-trimethoxyflanon (7 ), quercetin (8) , (3 beta, 5 alpha, 6 beta, 7 beta, 14 beta)-eudesmen-3,5,6,11-tetrol (9), syringaresinol (10), liriodendrin (11), and genkwanin (12).. Compounds 3-7, 10-12 were isolated from this species for the first time, and compounds 3, 5, 7, 10, 11 were obtained from genus Chrysanthemum for the first time.

Topics: Chalcones; Chrysanthemum; Flavones; Flavonoids; Flavonols; Flowers; Furans; Glucosides; Lignans; Quercetin

In the present study, liriodendrin isolated by activity-guided fractionation from the ethyl acetate (EtOAc) extracts of the stem bark of Acanthopanax senticosus, was evaluated for anti-inflammatory and antinociceptive activities. Liriodendrin (5, 10 mg/kg/day, p. o.) significantly inhibited the increase of vascular permeability induced by acetic acid in mice and reduced an acute paw edema induced by carrageenan in rats. When the analgesic activity was measured by the acetic acid-induced writhing test and hot plate test, liriodendrin showed a dose-dependent inhibition in animal models. In addition, syringaresinol, the hydrolysate of liriodendrin, more potently inhibited the LPS-induced production of NO, PGE 2 and TNF-alpha production of macrophages than liriodendrin. Consistent with these observations, the expression level of iNOS and COX-2 enzyme was decreased by syringaresinol in a concentration-dependent manner. These results suggest that the anti-inflammatory and antinociceptive effects of liriodendrin after oral administration were attributable to the in vivo transformation to syringaresinol, which may function as the active constituent.

Topics: Analgesics; Animals; Anti-Inflammatory Agents, Non-Steroidal; Chemical Fractionation; Cyclooxygenase 2; Dinoprostone; Eleutherococcus; Furans; Glucosides; Isoenzymes; Korea; Lignans; Lipopolysaccharides; Male; Mice; Mice, Inbred ICR; Nitric Oxide; Nitric Oxide Synthase; Nitric Oxide Synthase Type II; Pain Measurement; Plant Bark; Plant Stems; Prostaglandin-Endoperoxide Synthases; Rats; Rats, Sprague-Dawley; Tumor Necrosis Factor-alpha