Isolation of Nicotinic Acid (Vitamin B3) and N‑Propylamine after Myosmine Peroxidation

• Published in: Journal of agricultural and food chemistry 2016-01, Vol.64 (1), p.178-184
• Main Authors: Zwickenpflug, Wolfgang, Högg, Christof, Feierfeil, Johannes, Dachs, Manuel, Gudermann, Thomas
• Format: Article
• Language: English
• Subjects: Alkaloids - chemistry; Molecular Structure; Niacin - chemistry; Niacinamide - chemistry; Oxidation-Reduction; Propylamines - chemistry
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.5b04913

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.