title: Isolation of (S)-(+)-naproxene from Musa acuminata. Inhibitory effect of naproxene and its 7-methoxy isomer on constitutive COX-1 and inducible COX-2.
abstract: The isolation and characterisation of (S)-(+)-6-methoxy-alpha-methyl-2-naphthaleneacetic acid, a well known synthetic non-steroidal anti-inflammatory drug (naproxene), from a natural source is described for the first time. We evaluated the ability of naproxene and its 7-methoxy isomer to abrogate constitutive COX-1 and inducible COX-2 activity in human A549 cells. Naproxene inhibited COX-1 (IC50 = 3.42 microM) and COX-2 (IC50 = 1.53 microM), whereas the 7-methoxy isomer had no appreciable effect on COX-1 (IC50 >> 100 microM) but also abrogated the activity of COX-2 enzyme (IC50 = 14.42 microM).
authors.forename: T
authors.initials: T
authors.lastname: Abad
authors.forename: G
authors.initials: G
authors.lastname: McNaughton-Smith
authors.forename: W Q
authors.initials: WQ
authors.lastname: Fletcher
authors.forename: F
authors.initials: F
authors.lastname: Echeverri
authors.forename: R
authors.initials: R
authors.lastname: Diaz-Peñate
authors.forename: C
authors.initials: C
authors.lastname: Tabraue
authors.forename: C M
authors.initials: CM
authors.lastname: Ruiz de Galarreta
authors.forename: F
authors.initials: F
authors.lastname: López-Blanco
authors.forename: J G
authors.initials: JG
authors.lastname: Luis
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007527:Isoenzymes / Q000494:pharmacology*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008565:Membrane Proteins; D009288:Naproxen / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011451:Prostaglandin-Endoperoxide Synthases / Q000494:pharmacology*; D014407:Tumor Cells, Cultured; D019862:Zingiberales / Q000737:chemistry*
chemical_list: C412806:7-methoxy-alpha-methyl-2-naphthaleneacetic acid; D000894:Anti-Inflammatory Agents, Non-Steroidal; D004791:Enzyme Inhibitors; D007527:Isoenzymes; D008565:Membrane Proteins; D009288:Naproxen; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; C496511:PTGS1 protein, human; C496540:PTGS2 protein, human; D011451:Prostaglandin-Endoperoxide Synthases