title: Isolation of Nicotinic Acid (Vitamin B3) and N-Propylamine after Myosmine Peroxidation.
abstract: The alkaloid myosmine (3-(1-pyrroline-2-yl)pyridine) is widespread in biological matrixes including foodstuffs and tobacco products. Some in vitro tests in cellular systems showed mutagenic activity for myosmine. Myosmine activation including peroxidation mechanism employs unstable oxazirane intermediates. The formation of minor metabolite 3-hydroxymethyl-pyridine in rat metabolism experiments as well as in in vitro peroxidation assays suggests its further oxidation to nicotinic acid and possible concomitant formation of n-propylamine. A sensitive high-performance liquid chromatography-ultraviolet (HPLC-UV) method was developed for the direct analysis of n-propylamine in the peroxidation assay solution of myosmine employing derivatization with 3,5-dinitrobenzoyl chloride. Additionally, during peroxidation procedures, formation of 3-pyridylmethanol to nicotinic acid, the essential vitamin B3, was observed and characterized using HPLC-UV and gas chromatography/mass spectrometry. This new reaction pathway may present further contribution to our knowledge of myosmine's significance in human food including its activation in human organism, foodstuffs, and biological systems.
authors.affiliation: Walther-Straub-Institute of Pharmacology and Toxicology, University of Munich , Nussbaumstrasse 26, D-80336 Munich, Germany.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Zwickenpflug
authors.affiliation: Walther-Straub-Institute of Pharmacology and Toxicology, University of Munich , Nussbaumstrasse 26, D-80336 Munich, Germany.
authors.forename: Christof
authors.initials: C
authors.lastname: Högg
authors.affiliation: Walther-Straub-Institute of Pharmacology and Toxicology, University of Munich , Nussbaumstrasse 26, D-80336 Munich, Germany.
authors.forename: Johannes
authors.initials: J
authors.lastname: Feierfeil
authors.affiliation: Walther-Straub-Institute of Pharmacology and Toxicology, University of Munich , Nussbaumstrasse 26, D-80336 Munich, Germany.
authors.forename: Manuel
authors.initials: M
authors.lastname: Dachs
authors.affiliation: Walther-Straub-Institute of Pharmacology and Toxicology, University of Munich , Nussbaumstrasse 26, D-80336 Munich, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Gudermann
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D015394:Molecular Structure; D009525:Niacin / Q000737:chemistry*; D009536:Niacinamide / Q000737:chemistry*; D010084:Oxidation-Reduction; D011437:Propylamines / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D011437:Propylamines; D009536:Niacinamide; D009525:Niacin; C002398:myosmine
keywords: myosmine; n-propylamine; nicotinic acid; peroxidation; vitamin B3