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Quinoline alkaloids in honey: Further analytical (HPLC-DAD-ESI-MS,multidimensional diffusion-ordered NMR spectroscopy), theoretical and chemometric studies
Authors:Giangiacomo Beretta  Roberto Artali  Enrico Caneva  Serena Orlandini  Marisanna Centini  Roberto Maffei Facino
Affiliation:1. Department of Pharmaceutical Sciences “Pietro Pratesi”, Faculty of Pharmacy, University of Milan, via Mangiagalli 25, 20133 Milan, Italy;2. CIGA-Centro Interdipartimentale Grandi Apparecchiature, University of Milan, via Golgi 19, 20133 Milan, Italy;3. Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Florence, Via U. Schiff 6, Sesto Fiorentino, 50019 Florence, Italy;4. Centro Interdipartimentale di Scienza e Tecnologia Cosmetiche, University of Siena, Via della Diana 2, 53100 Siena, Italy
Abstract:The wound-healing properties of honey are well established and it has been suggested that, among its pharmaco-active constituents, kynurenic acid (KA) exerts antinociceptive action on injured tissue by antagonizing NMDA at peripheral GABA receptors. The aim of this study was to investigate the quantitative profile of KA and of two recently identified, structurally related derivatives, 3-pyrrolidinyl-kynurenic acid (3-PKA) and its γ-lactamic derivative (γ-LACT-3-PKA), by examining their mass spectrometric behavior, in honeys from different botanical sources. We used a combination of HPLC-DAD-ESI-MS and NMR techniques (one-dimensional 1H NMR and diffusion-ordered spectroscopy NMR).
Keywords:KA, kynurenic acid   3-PKA, 3-(2&prime  -pyrrolidinyl)-kynurenic acid γ-LACT-3-PKA   TPC, total phenol content   ARA, antiradical activity   IDO, indoleamine-2,3-dioxygenase   GAE, gallic acid equivalent   DOSY, dispersion ordered spectroscopy   HPLC, high pressure liquid chromatography   NMR, nuclear magnetic resonance   MS, mass spectrometry   SIM, single ion monitoring
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