Acrolein contributes strongly to antimicrobial and heterocyclic amine transformation activities of reuterin.
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.
Laboratory of Food Biotechnology, Institute of Food, Nutrition and Health, Department of Health Sciences and Technology, ETH Zurich, Zurich, Switzerland.
Christina
C
Engels
Laboratory of Food Biotechnology, Institute of Food, Nutrition and Health, Department of Health Sciences and Technology, ETH Zurich, Zurich, Switzerland.
Clarissa
C
Schwab
Laboratory of Food Nutrition and Toxicology, Institute of Food, Nutrition and Health, Department of Health Sciences and Technology, ETH Zurich, Zurich, Switzerland.
Jianbo
J
Zhang
Laboratory of Food Biotechnology, Institute of Food, Nutrition and Health, Department of Health Sciences and Technology, ETH Zurich, Zurich, Switzerland.
Marc J A
MJ
Stevens
Laboratory of Food Biotechnology, Institute of Food, Nutrition and Health, Department of Health Sciences and Technology, ETH Zurich, Zurich, Switzerland.
Corinne
C
Bieri
Laboratory of Organic Chemistry, Department of Chemistry and Applied Sciences, ETH Zurich, Zurich, Switzerland.
Marc-Olivier
MO
Ebert
Laboratory of Environmental Chemistry, Institute of Biogeochemistry and Pollutant Dynamics, Department of Environmental Systems Science, ETH Zurich, Zurich, Switzerland.
Kristopher
K
McNeill
Laboratory of Food Nutrition and Toxicology, Institute of Food, Nutrition and Health, Department of Health Sciences and Technology, ETH Zurich, Zurich, Switzerland.
Shana J
SJ
Sturla
Laboratory of Food Biotechnology, Institute of Food, Nutrition and Health, Department of Health Sciences and Technology, ETH Zurich, Zurich, Switzerland.
Christophe
C
Lacroix
D000171:Acrolein / Q000737:chemistry / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism; D000069196:Gastrointestinal Microbiome; D005985:Glyceraldehyde / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D011407:Propane / Q000737:chemistry / Q000378:metabolism
D000900:Anti-Bacterial Agents; C047158:3-hydroxypropionaldehyde; D005985:Glyceraldehyde; D000171:Acrolein; D011407:Propane