title: Anti-inflammatory and free radial scavenging activities of the constituents isolated from Machilus zuihoensis.
abstract: A 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 (IC₅₀ 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 (IC₅₀ 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-kB 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.
authors.affiliation: School of Pharmacy, College of Pharmacy, Taipei Medical University, Taipei 110, Taiwan.
authors.forename: Yi-Wen
authors.initials: YW
authors.lastname: Mao
authors.forename: Hsiang-Wen
authors.initials: HW
authors.lastname: Tseng
authors.forename: Wen-Li
authors.initials: WL
authors.lastname: Liang
authors.forename: Ih-Sheng
authors.initials: IS
authors.lastname: Chen
authors.forename: Shui-Tein
authors.initials: ST
authors.lastname: Chen
authors.forename: Mei-Hsien
authors.initials: MH
authors.lastname: Lee
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002109:Caffeic Acids / Q000494:pharmacology; D002460:Cell Line; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005697:Galactosides / Q000737:chemistry; D024243:HMGB1 Protein / Q000378:metabolism; D006801:Humans; D016753:Interleukin-10 / Q000378:metabolism; D053583:Interleukin-1beta / Q000378:metabolism; D019770:Lauraceae / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D016328:NF-kappa B / Q000037:antagonists & inhibitors; D052247:Nitric Oxide Synthase Type II / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D011794:Quercetin / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D013481:Superoxides / Q000737:chemistry; D014409:Tumor Necrosis Factor-alpha / Q000378:metabolism
chemical_list: D000893:Anti-Inflammatory Agents; D002109:Caffeic Acids; D016166:Free Radical Scavengers; D005697:Galactosides; D024243:HMGB1 Protein; D053583:Interleukin-1beta; D008070:Lipopolysaccharides; D009005:Monosaccharides; D016328:NF-kappa B; D010936:Plant Extracts; D014409:Tumor Necrosis Factor-alpha; C517440:quercetin-3'-O-beta-D-glucopyranoside; C508165:quercetin-3-O-beta-D-galactopyranoside; D013481:Superoxides; D016753:Interleukin-10; C032773:ethyl caffeate; D011794:Quercetin; D052247:Nitric Oxide Synthase Type II
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