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TOXIC SUGAR DERIVATIVES PRODUCED DURING MAILLARD REACTION AND
ITS IMPLICATIONS ON HUMAN HEALTH
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INTRODUCTION

The Maillard reaction, named after L
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Maillard, is also known as non-enzymatic browning
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The Maillard reaction begins with the reaction of reducing sugars with amines to form
glycosylamines (Mailard, 1912)
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The reaction is sequential, forming
highly reactive intermediates that then react in a variety of ways
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The Maillard reaction also occurs at room temperature, but is much slower
and slowest at low temperatures, low pH, and low Aw values (Naresh et al, 2017)
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The sulfur-containing amino acids methionine and cysteine play a central role in the
formation of the highly flavored components obtained in the Maillard reaction
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Unsaturated fatty acids and aldehyde fatty acid components also contribute to the formation of
odorous heteroaromatic compounds during the Maillard reaction (Naresh et al
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1
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It is
widely used in food due to its role in producing color, flavor, texture and other functional
properties
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The Maillard reaction is important in the food industry as it is associated with aroma,
flavor and color, especially in traditional processes such as roasting coffee and cocoa beans, baking
bread and cakes, toasting grains and cooking meat
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2013)
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These
products are also used to improve protein properties
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2013)
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Chemistry of the Maillard Reaction

This reaction is dependent on physical parameters such as heat, humidity, pH and NH2 and
produces sophisticated compounds not naturally found in food
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The Maillard reaction can be divided into three stages
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In the early stages, colorless products like sugar-amine
condensations, i
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N-glycoside compounds, are formed
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This reaction is
known as the Amadori rearrangement and yields 5-hydroxymethylfurfural, reductones and
dicarbonyl compounds
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Coloration occurs
during the thermal conversion of sugars due to a pH-scaled response to sugar groups, but amino
acids are not directly responsible for coloration (Adrian
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The characteristic color of foods
such as coffee, malt, bread, cocoa, and a variety of cooked foods is due to melanoidins, which are
massive brown nitrogen pigments (Bastos et al
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The final and intermediate steps are the
most crucial for creating flavor and aroma through Strecker degradation, in addition to desired
color (Somoza
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Three Steps of Maillard Reaction
Initial Step

Intermediate Step

Final Step

Fig 1: Mechanism of Maillard reaction

1
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The Maillard process also occurs
in living cells, hence the term "glycation" is used to distinguish between protein enzymatic
glycosylation in living cells and nonenzymatic glycosylation in food
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AGEs play a role in a number of disorders (i
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, pathophysiological processes)
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1
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Early on in the Maillard reaction, lysine derivatives such N-lactulosyllysine, N-fructosyllysine, or
N-maltulosyllysine are the main reaction products
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Glyoxal,
methylglyoxal, and 3-deoxyglucosulose are examples of 1,2-dicarbonyl molecules that are created
during the intermediate stage
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N-carboxymethyllysine
(CML), pyrraline, pronyl-lysine, pentosidine, gyloxal-lysine-dimer, methylglyoxal-lysine-dimer,
and 3-deoxyglucosulose-lysine-dimer are among the AGEs that are detected in meals (figure 2)
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2 Chemical structure of CML and pyrraline
Pyralines are heterocyclic AGEs formed by the reaction of the ε-amino group of lysine with 3deoxyglucosulose
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N-ε-Carboxymethyllysine (CML) was the first advanced Maillard reaction amino acid
derivative formed by oxidative cleavage of the Amadori product
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4

Heat treatment and subsequent storage of milk changes lysine by 10-20%
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Lysine derivatives such as N-ε-fructoseridine and N-εmaltuloceridine are found in baked goods
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Pyralin concentrations detected ranged from 150 mg/kg protein in
sterilized milk to 3,700 mg/kg protein in bread crusts
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2
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1

Maillard reaction Products

Amadori compounds, which are the primary form of glycation chemicals, are found in meals
containing protein that experience early Maillard reactions
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The pathogenesis of diabetes and associated biological conditions,
such as cataract, joint rigidity, or diabetic nephropathy, were related to the glycation process that
takes place in vivo
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However, there is disagreement regarding a dietary glycation compound's toxicological
impact
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Healthy individuals' bodies slowly produce AGEs, however this
process advances more favorably when dietary Maillard reaction products are present
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As a result, there is a concern about the safety
of AGEs in food (Sebekova and Somoza 2007)
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Hydroxymethylfurfural (HMF)

The Maillard reaction's intermediate hydroxymethylfurfural (5-hydroxymethyl-2-furaldehyde,
HMF) is naturally produced during heating (MR)
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11 g/mol
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HMF is created during
the heating process and subsequent storage of carbohydrate-rich goods
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Acidic foods have a
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significant potential for producing HMF
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By way of the Maillard reaction, caramelization, or pyrolysis of either
reducing moieties of disaccharides or free monosaccharides, sugars break down into furfural
molecules (Morales 2009)
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H
1

O
2

5

O

OH
3

4

Fig 3
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However, it is uncertain whether human
exposure to HMF poses a risk to their health, and there is no information available from
epidemiological research or case reports about a possible connection between HMF and an
increased risk of developing cancer in people
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2013)
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5 mg of body weight per day for a 60 kg
individual
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1984)
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3

Hazards of Furan

Furan is a colorless compound with a molecular weight of 68 and a boiling point of 31 C
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A significant class of chemicals that are produced during the Maillard reactions
in foods are furans (Maga 1979)
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Furan is created through a variety of processes, including the thermal oxidation of ascorbic
acid, polyunsaturated fatty acids, and carotenoids, as well as the thermal degradation of certain
amino acids and reducing sugars like glucose, lactose, and fructose (Vranová and Ciesarová,
2009)
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According to Becalski
and Seaman (2005), the oxidation of polyunsaturated fatty acids (PUFAs) at high temperatures can
result in the synthesis of furan, however the addition of commercially available antioxidants (such
tocopherol acetate) can inhibit the formation of furan by up to 70%
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In the 1960s and 1970s, parent furan was
discovered in a few heat-treated foods, including coffee, canned meat, bread, cooked chicken,
sodium caseinate, hazelnuts, hydrolyzed soy protein, rapeseed protein, fish protein concentrate,
and caramel (Maga)
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Toxicity of Furan
The production of hepatic cholangiocarcinomas in rats and mice is the most notable tumor that
furan induces in animal experiments (Vranová and Ciesarová 2009)
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(Group 2B)
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Furan is swiftly absorbed by the body, but it is also efficiently eliminated
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Heterocyclic Aromatic Amines

More than 25 HCAs have been isolated and identified in cooked meat products since Japanese
scientist Sugimura first detected carcinogenic and/or mutagenic heterocyclic aromatic amines
(HCAs/HAAs) in fish and meat cooked at temperatures over 150 C in 1977
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2008)
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Some HAAs, including 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2amino-3,4-dimethylimidazo[4,5-f]quinoline

(MeIQ),

and

2-amino-1-methyl-6-

phenylimidazo[4,5-b]pyridine (PhIP), have been classified by the International Agency for
Research on Cancer as probable human carcinogens and class 2A, respectively (Kizil et al
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Aminoimidazoazoarenes (AIAs), also known as imidazoquinoline (IQ)-type compounds
or thermic HCAs, and aminocarbolines, sometimes known as non-IQ-type HCAs, are two basic
categories into which HCAs can be divided
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They contain a quinoline, quinoxaline, or pyridine attached to an
imidazo group
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2017)
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According to Sugimura and Adamson (2000), the production of
them is significantly influenced by the type of meat, its fat and moisture content, pH, sugar, free
amino acid, and creatinine content, lipid oxidation, and the presence of antioxidants (Kizil et al
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Toxicity of Heterocyclic Aromatic Amines in Food
Salmonella's mutagenicity was affected by the number and locations of exocyclic substituents,
particularly the 2-amino-group of the imidazo portion of the chemical structure present in most
HCAs, and varied between the strongest and weakest HCAs by more than 160,000 times (Nagao
et al
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HCAs have been discovered to be powerful carcinogens that, after prolonged oral
exposure, cause a range of tumor histologies in numerous organs (Sugimura and Adamson 2000)
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Additionally, strong
epidemiological data link a high consumption of HCAs to colon cancer, however this relationship
is not always reliable (Margaretha and Kerstin 2005)
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Meat and fish cooked at home are the
main food sources of human exposure to HAAs
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2
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08 that is made up of a reactive
ethylenic double bond coupled to a carboxamide group (IARC 1994)
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3 kPa/25 mmHg and a melting point of 84
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3 C
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A
reactive electrophilic double bond and an amide group are both present in the difunctional
monomer acrylamide (Habermann, 1991)
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The 1,3-DCP was hepatotoxic, caused a number of tumors in a number of rat organs,
and was genotoxic in a test tube
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051 g/kg body weight, while the estimated high consumption
(which included young children) was 0
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3
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The Maillard reaction has both positive and negative sides
in the food industry
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The downside is the development of off-flavours,
loss of flavor, discoloration, and loss of nutritional value of proteins
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Such toxins can be classified according to
their structural characteristics or the processing methods in which they occur
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Interdisciplinary knowledge is
required to understand the effects on different nutrients and the formation of numerous chemical
toxins and their effects on health
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Therefore, a strong and systematic
multidisciplinary research project and effort is required to further elucidate these complex heat
treatment issues
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