title: Structures of new phenylbutanoids and nitric oxide production inhibitors from the rhizomes of Zingiber cassumunar.
abstract: The methanolic (MeOH) extract from the rhizomes of Zingiber cassumunar showed nitric oxide (NO) production inhibitory effects induced by lipopolysaccharide (LPS) in mouse peritoneal macrophages. From the MeOH extract, six new phenylbutanoids, phlains I-VI, were isolated together with 16 known constituents. The structures of new phenylbutanoids were determined on the basis of physicochemical and chemical evidence. In addition, the inhibitory effects of the principal constituents on the NO production were examined. Among them, phlain III (IC50=24 microM), (E)-1-(3,4-dimethoxyphenyl)buta-1,3-diene (69 microM), (E)-1-(2,4,5-trimethoxyphenyl)buta-1,3-diene (83 microM), and cassumunaquinone 1 (47 microM) were found to show the inhibitory effects.
authors.affiliation: Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
authors.forename: Seikou
authors.initials: S
authors.lastname: Nakamura
authors.forename: Junko
authors.initials: J
authors.lastname: Iwami
authors.forename: Hisashi
authors.initials: H
authors.lastname: Matsuda
authors.forename: Hiroko
authors.initials: H
authors.lastname: Wakayama
authors.forename: Yutana
authors.initials: Y
authors.lastname: Pongpiriyadacha
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
mesh_terms: D000818:Animals; D001565:Benzoates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000494:pharmacology; D017737:Macrophages, Peritoneal / Q000187:drug effects / Q000378:metabolism; D008297:Male; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification; D027343:Rhizome / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D030521:Zingiberaceae / Q000737:chemistry*
chemical_list: D001565:Benzoates; D008070:Lipopolysaccharides; D010936:Plant Extracts; D009569:Nitric Oxide