Mao, Yi-WenYi-WenMaoTseng, Hsiang-WenHsiang-WenTsengLiang, Wen-LiWen-LiLiangChen, Ih-ShengIh-ShengChenChen, Shui-TeinShui-TeinChenLee, Mei-HsienMei-HsienLee2012-10-202018-07-062012-10-202018-07-062011http://ntur.lib.ntu.edu.tw//handle/246246/243343A new biflavonol glycoside, quercetin-3-O-β-D-glucopyranoside- (3'→O-3''')- quercetin-3-O-β-D-galactopyranoside (9), together with eight known compounds was isolated for the first time from the leaves of Machilus zuihoensis Hayata (Lauraceae). The structure of compound 9 was elucidated by various types of spectroscopic data analysis. Analysis of the biological activity assay found that compound 9 showed significant superoxide anion scavenging activity (IC 50 is 30.4 μM) and markedly suppressed LPS-induced high mobility group box 1 (HMGB-1) protein secretion in RAW264.7 cells. In addition, the HMGB-1 protein secretion was also inhibited by quercitrin (3), ethyl caffeate (6), and ethyl 3-O-caffeoylquinate (7) treatment. In the LPS-stimulated inducible nitric oxide synthase (iNOS) activation analysis, two known compounds, quercetin (1) and ethyl caffeate (6), were found to markedly suppress nitric oxide (NO) production (IC 50 value, 27.6 and 42.9 μM, respectively) in RAW264.7 cells. Additionally, it was determined that ethyl caffeate (6) down-regulated mRNA expressions of iNOS, IL-1β, and IL-10 in the LPS-treatment of RAW264.7 cells via a suppressed NF-κB pathway. These results suggested for the first time that the new compound 9 and other constituents isolated from M. zuihoensis have potential anti-inflammatory and superoxide anion scavenging effects. These constituents may be useful for treating various inflammatory diseases. ? 2011 by the authors; licensee MDPI, Basel, Switzerland.en-USAnti-inflammatory; Ethyl caffeate; Machilus zuihoensis; Quercetin; Quercetin-3-O-β-D- glucopyranoside-(3'→O-3''')-quercetin-3-O-β-D-galactopyranoside[SDGs]SDG3antiinflammatory agent; caffeic acid derivative; drug derivative; ethyl caffeate; galactoside; high mobility group B1 protein; immunoglobulin enhancer binding protein; inducible nitric oxide synthase; interleukin 10; interleukin 1beta; lipopolysaccharide; monosaccharide; plant extract; quercetin; quercetin 3 O beta D galactopyranoside; quercetin 3' O beta D glucopyranoside; quercetin-3'-O-beta-D-glucopyranoside; quercetin-3-O-beta-D-galactopyranoside; scavenger; superoxide; tumor necrosis factor alpha; animal; article; cell line; chemical structure; chemistry; cytology; drug antagonism; drug effect; human; isolation and purification; Lauraceae; macrophage; metabolism; mouse; secretion; Animals; Anti-Inflammatory Agents; Caffeic Acids; Cell Line; Free Radical Scavengers; Galactosides; HMGB1 Protein; Humans; Interleukin-10; Interleukin-1beta; Lauraceae; Lipopolysaccharides; Macrophages; Mice; Molecular Structure; Monosaccharides; NF-kappa B; Nitric Oxide Synthase Type II; Plant Extracts; Quercetin; Superoxides; Tumor Necrosis Factor-alphajournal article10.3390/molecules16119451http://ntur.lib.ntu.edu.tw/bitstream/246246/243343/-1/42.pdf