title: Inhibitors of nitric oxide production from the rhizomes of Alpinia galanga: structures of new 8-9' linked neolignans and sesquineolignan.
abstract: The 80% aqueous acetone extract from the rhizomes of Alpinia galanga showed nitric oxide (NO) production inhibitory activities in mouse peritoneal macrophages. From the aqueous acetone extract, three new 8-9' linked neolignans, galanganal, galanganols A and B, and a sesquineolignan, galanganol C, were isolated together with nine known phenylpropanoids and p-hydroxybenzaldehyde. The structures of new neolignans were determined on the basis of physicochemical and chemical evidence. In addition, the inhibitory effects of the constituents from the rhizomes of A. galanga on NO production induced by lipopolysaccharide in mouse peritoneal macrophages were examined. Among them, galanganal (IC50=68 microM), galanganols B (88 microM) and C (33 microM), 1'S-1'-acetoxychavicol acetate (2.3 microM), 1'S-1'-acetoxyeugenol acetate (11 microM), trans-p-hydroxycinnamaldehyde (ca. 20 microM), trans-p-coumaryl alcohol (72 microM), and trans-p-coumaryl diacetate (19 microM) were found to show inhibitory activity.
authors.affiliation: Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
authors.forename: Toshio
authors.initials: T
authors.lastname: Morikawa
authors.forename: Shin
authors.initials: S
authors.lastname: Ando
authors.forename: Hisashi
authors.initials: H
authors.lastname: Matsuda
authors.forename: Shinya
authors.initials: S
authors.lastname: Kataoka
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
mesh_terms: D032429:Alpinia; D000818:Animals; D004305:Dose-Response Relationship, Drug; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D008297:Male; D051379:Mice; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D027343:Rhizome
chemical_list: D017705:Lignans; D010936:Plant Extracts; D009569:Nitric Oxide