ICOMST st International Congress of Meat Science & Technology MECHANISTIC PATHWAYS TO PROCESS-INDUCED TOXICANTS IN MEAT
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1 ICOMST st International Congress of Meat Science & Technology MECHANISTIC PATHWAYS TO PROCESS-INDUCED TOXICANTS IN MEAT
2 Content General introduction Summary of chemical reactions generating toxicants Formation of heterocylic Aromatic amines (HAA) Formation of polycyclic aromatic hydrocarbons (PAH) Formation of mono-chloropropanediol derivatives (MCPD)
3 GENERAL INTRODUCTION What is the origin of process-induced toxicants? Meat is subjected to various treatments some involves heat (roasting, grilling, barbecuing, frying, cooking, etc.) others involve exposure to enzymes and microorganisms. Each of the above treatments may induce the formation of a specific class of toxicants
4 Process-specific carcinogens Curing with nitrites N-nitroso compounds Fermentation Smoking/Salting Thermal treatments Biogenic amines 3-monochloropropane- 1,2-diol (3-MCPD), PAH PAHs & HAAs
5 INTRODUCTION In general, during heat processing stage, Maillard reaction, thermal decompositions and lipid oxidation reactions are important chemical transformations that can generate the building blocks or precursors of potential toxicants from carbohydrates, amino acids and lipid precursors
6 Thermally allowed chemical transformations Decarboxylation Maillard & Strecker reaction Thermal oxidation Diels-Alder reaction Aldol condensation Isomerization Dehydrations
7 Maillard and Strecker reactions Maillard reaction allows incorporation of amino acid nitrogen as heteroatoms in pyrazines, pyridines, pyrroles etc. Strecker reaction converts amino acids into their corresponding reactive aldehydes
8 PROCESS-INDUCED TOXICANTS IN MEAT Nitrosocompounds heterocyclic aromatic amines (HAA) and polycyclic aromatic hydrocarbons (PAH). Toxicants Biogenic amines HAA PAH This presentation will be focusing mainly on heterocyclic aromatic amines (HAA) and polycyclic aromatic hydrocarbons (PAH)
9 Examples of Polycyclic Aromatic Hydrocarbones
10 Classification of heterocyclic aromatic amines (HAAs)
11 Two types of precursors were identified for their formation: (1) Pre-existing in meat such as specific amino acids (tryptophan & phenylalanine) or creatine/creatinine (2) Those that are generated during thermal processing through either Maillard reaction such as pyrazines or pyridines, Strecker aldehydes such as phenylacetaldehyde, formaldehyde and acetaldehyde or lipid oxidation/thermal degradation products such as alkenes, dienes and short chain aldehdyes of which some are similar to those generated through the Maillard reaction
12 SOME PRE-EXISTING CARCINOGENIC AMINO ACID PRECURSORS IN MEAT
13 Proposed mechanism of formation of PhIP based on Murkovic, et. al., (1999) and Zamaro et al., (2014). (*) indicates mixed origin from amino acids or creatine.
14 Proposed mechanism of formation of imidazopyridins
15 Proposed precursors involved in the formation of imidazoquinoxalines and imidazoquinolines
16 Proposed mechanism of formation of imidazoquinoxalines
17 Proposed mechanism of formation of imidazoquinolines
18 Proposed mechanism of formation of IQ isomer based on Zamaro and Hidalgo (2015)
19 Proposed mechanism of formation of β-carbolines P-S = Pictet-Spengler condensation.
20 Proposed pathways to polycyclic aromatic hydrocarbons (PAHs) DA = Diels-Alder reaction
21 Hypothetical and sequential Diels-Alder (DA) cyclocondensation reactions of ethene (ET) and buta-1,3-diene (BD) to generate various polycyclic aromatic hydrocarbons (PAHs) The steps shown involves DA reactions and/or partial oxidations and/or isomerizations of the double bonds
22 Two precursors are required TAG, a source of chlorine and heating
23 Mechanism of formation of 3-mcpd derivatives Triacylglycerol Rahn, K.K.R., Yaylayan, VA. Monitoring cyclic acyloxonium ion formation in tripalmitin using infrared spectroscopy and isotope labeling technique. Eur. J. Lipid Sci. Technol. 2011, 113 (3), Rahn, K.K.R., Yaylayan, VA. What do we know about the molecular mechanism of 3-MCPD esterformation? Eur. J. Lipid Sci. Technol. 2011, 113 (3),
24 Conclusions Various chemical pathways and precursors can be involved in the generation of process-induced toxicants, understanding their detailed steps can help mitigate their formation. However, there are no confirmed and accepted mechanisms for all the known toxicants.
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