Acrolein contributes strongly to antimicrobial and heterocyclic amine transformation activities of reuterin
Abstract
Glycerol/diol dehydratases catalyze the conversion of glycerol to 3-hydroxypropionaldehyde (3-HPA), the basis of a multi-component system called reuterin. Reuterin has antimicrobial properties and undergoes chemical conjugation with dietary heterocyclic amines (HCAs). In aqueous solution reuterin is in dynamic equilibrium with the toxicant acrolein. It was the aim of this study to investigate the extent of acrolein formation at various physiological conditions and to determine its role in biological and chemical activities. The application of a combined novel analytical approach including IC-PAD, LC-MS and NMR together with specific acrolein scavengers suggested for the first time that acrolein, and not 3-HPA, is the active compound responsible for HCA conjugation and antimicrobial activity attributed to reuterin. As formation of the HCA conjugate was observed in vivo, our results imply that acrolein is formed in the human gut with implications on detoxification of HCAs. We propose to re-define the term reuterin to include acrolein. Mehr anzeigen
Persistenter Link
https://doi.org/10.3929/ethz-b-000122015Publikationsstatus
publishedExterne Links
Zeitschrift / Serie
Scientific ReportsBand
Seiten / Artikelnummer
Verlag
NatureThema
Biotechnology; BiochemistryOrganisationseinheit
02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry03850 - McNeill, Kristopher / McNeill, Kristopher
03853 - Sturla, Shana / Sturla, Shana
03626 - Lacroix, Christophe (emeritus) / Lacroix, Christophe (emeritus)
08663 - NMR-Service LOC