title: Orthoquinone and naphthalenone derivatives from Berrya ammonilla and their anti-inflammatory activity.
abstract: A new orthoquinone, berryammone A (1), and four new naphthalenone derivatives, berryammone B (2), berryammone C (3), 6-O-methylberryammone C (4), and 4-O-methylberryammone C (5), have been isolated from the stem of Berrya ammonilla, together with eleven known compounds (6-16). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolates, compounds 1-3, 5, (+)-pinoresinol (6), and betulinic acid (12) exhibited inhibition (IC50 ≤ 4.41 µM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 2, and 5 also inhibited fMLP/CB-induced elastase release with IC50 values ≤ 3.95 µM.
authors.affiliation: Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan.
authors.forename: Tsung-Hsien
authors.initials: TH
authors.lastname: Chou
authors.forename: Sheng-Kan
authors.initials: SK
authors.lastname: Chien
authors.forename: Tsong-Long
authors.initials: TL
authors.lastname: Hwang
authors.forename: Dau-Chang
authors.initials: DC
authors.lastname: Wei
authors.forename: Ih-Sheng
authors.initials: IS
authors.lastname: Chen
authors.forename: Ping-Jyun
authors.initials: PJ
authors.lastname: Sung
authors.forename: Ming-Jen
authors.initials: MJ
authors.lastname: Cheng
authors.forename: Sheng-Zehn
authors.initials: SZ
authors.lastname: Yang
authors.forename: Ken-Ming
authors.initials: KM
authors.lastname: Chang
authors.forename: Jih-Jung
authors.initials: JJ
authors.lastname: Chen
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical / Q000379:methods; D005663:Furans / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D017705:Lignans / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D019660:Malvaceae / Q000737:chemistry*; D015394:Molecular Structure; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000494:pharmacology; D009281:Naphthalenes / Q000737:chemistry / Q000494:pharmacology; D009285:Naphthoquinones / Q000737:chemistry / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000378:metabolism; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors; D053978:Pentacyclic Triterpenes; D013481:Superoxides / Q000378:metabolism; D014315:Triterpenes / Q000737:chemistry / Q000494:pharmacology; D000094062:Betulinic Acid
chemical_list: C575799:4-O-methylberryammone C; D000893:Anti-Inflammatory Agents; D005663:Furans; D017705:Lignans; D009281:Naphthalenes; D009285:Naphthoquinones; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; C575800:berryammone A; D013481:Superoxides; D009240:N-Formylmethionine Leucyl-Phenylalanine; D010196:Pancreatic Elastase; C103298:pinoresinol; D000094062:Betulinic Acid