4-5-epoxy-2-decenal and 4-hydroxy-2-nonenal

Coffee, as a source of acrylamide, needs to be investigated in depth to understand the contribution of different precursors. This study aimed to investigate the contributions of sucrose decomposition and lipid oxidation on acrylamide formation in coffee during roasting. Coffee beans and model systems were used to monitor the accumulation of neo-formed carbonyls during heating through sucrose decomposition and lipid oxidation. High resolution mass spectrometry analyses confirmed the formation of 5-hydroxymethylfurfural (HMF) and 3,4-dideoxyosone, which were identified as the major sugar decomposition products in both roasted coffee and model systems. Among others, 2-octenal, 2,4-decadienal, 2,4-heptadienal, 4-hydroxynonenal, and 4,5-epoxy-2-decenal were identified in relatively high quantities in roasted coffee. Formation and elimination of HMF in coffee during roasting had a kinetic pattern similar to those of acrylamide. Its concentration rapidly increased within 10 min followed by an exponential decrease afterward. The amount of lipid oxidation products tended to increase linearly during roasting. It was concluded from the results that roasting formed a pool of neo-formed carbonyls from sucrose decomposition and lipid oxidation, and they play certain role on acrylamide formation in coffee.

Topics: Acrylamide; Aldehydes; Chromatography, Liquid; Coffee; Epoxy Compounds; Food Handling; Furaldehyde; Hot Temperature; Oxidation-Reduction; Sucrose; Tandem Mass Spectrometry

The role of amino phospholipids in the removal of 4-hydroxy-2-alkenals and 4,5-epoxy-2-alkenals was studied to determine the fate of highly toxic oxygenated aldehydes produced in foods as a consequence of lipid oxidation. The results obtained showed that phosphatidylethanolamine rapidly removed both exogenously added aldehydes as well as the endogenously produced aldehydes when its fatty acid chains were oxidized in the presence of an oxidative stress inducer. This removal, which was always produced in the range of pH (6-9) and temperature (25-60 degrees C) studied, produced the corresponding carbonyl-amine reaction products between the aldehydes and the amino group of the amino phospholipid. These results suggest that, in the presence of amino phospholipids, the oxidation of polyunsaturated fatty acid chains is not likely to produce free oxygenated aldehydes in enough concentration to pose a significant risk for human health. On the other hand, these compounds contributed to the formation of specific carbonyl-amine reaction products whose toxicity is mostly unknown at present.

Topics: Aldehydes; Ascorbic Acid; Epoxy Compounds; Food Analysis; Gas Chromatography-Mass Spectrometry; Hydrogen-Ion Concentration; Iron; Lipids; Oxidation-Reduction; Phosphatidylethanolamines; Phospholipids; Pyrroles; Temperature

Epidemiological data suggest that dietary antioxidants play a protective role against cancer. This has led to the proposal that dietary supplementation with antioxidants such as vitamin C (vit C) may be useful in disease prevention. However, vit C has proved to be ineffective in cancer chemoprevention studies. In addition, concerns have been raised over potentially deleterious transition metal ion-mediated pro-oxidant effects. We have now determined that vit C induces lipid hydroperoxide decomposition to the DNA-reactive bifunctional electrophiles 4-oxo-2-nonenal, 4,5-epoxy-2(E)-decenal, and 4-hydroxy-2-nonenal. The compound 4,5-Epoxy-2(E)-decenal is a precursor of etheno-2'-deoxyadenosine, a highly mutagenic lesion found in human DNA. Vitamin C-mediated formation of genotoxins from lipid hydroperoxides in the absence of transition metal ions could help explain its lack of efficacy as a cancer chemoprevention agent.

Topics: Aldehydes; Antioxidants; Ascorbic Acid; Buffers; Copper; Cyclooxygenase 1; Cyclooxygenase 2; DNA Adducts; DNA Damage; Epoxy Compounds; Ferrous Compounds; Humans; Isoenzymes; Linoleic Acids; Lipid Peroxides; Membrane Proteins; Metals; Mutagens; Oxidants; Oxidation-Reduction; Prostaglandin-Endoperoxide Synthases