Top

Published in:

2017 | OriginalPaper | Chapter

14. Chemical Stability: Browning and Oxidation

Authors : Naritchaya Potes, Aaron S. L. Lim, Yrjö H. Roos

Published in: Engineering Foods for Bioactives Stability and Delivery

Publisher: Springer New York

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

A number of food components are sensitive to deteriorative reactions, such as nonenzymatic browning and oxidation, during food storage. Food components, i.e., carbohydrates, lipids, proteins and water undergo changes due to the surrounding atmosphere, the presence of minor components and catalysts, and variations in local reactant concentrations resulting from changes in temperature, water migration, and the state of the components. Bioactive proteins and peptides may participate in nonenzymatic browning and oxidation reactions. Oil-soluble bioactive components, for example carotenoids, need protection against oxidation. Water content, and often the physical state of components as well as food structure, may have a significant impact on bioactive stability during food manufacturing and storage.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

previous chapter Nonthermal Stabilization Processes

next chapter Improvement of Bioaccessibility and Bioavailability: From Molecular Interactions to Delivery Systems

Acevedo N, Schebor C, Buera MP (2006) Water–solids interactions, matrix structural properties and the rate of non-enzymatic browning. J Food Eng 108:1108–1115CrossRef

Acevedo N, Schebor C, Buera MP (2008) Non-enzymatic browning kinetics analysed through water–solid interactions and water mobility in dehydrated potato. Food Chem 108:900–906CrossRef

Achir N, Randrianatoandro VA, Bohuon P, Laffargue A, Avallone S (2010) Kinetic study of β-carotene and lutein degradation in oils during heat treatment. Eur J Lipid Sci Tech 112:349–361

Addis PB (1986) Occurrence of lipid oxidation products in foods. Food Chem Toxic 24:1021–1030CrossRef

Aguilera JM (1990) Microstructural principles of food processing and engineering. Elsevier, London, pp 309–327

Ahmed MU, Thorpe SR, Baynes JW (1986) Identification of N ^ε-carboxylethyllysine as a degradation product of fructoselysine in glycated protein. J Biol Chem 261:4889–4894

Ajandouz EH, Puigserver A (1999) Nonenzymatic browning reaction of essential amino acids: effect of pH on caramelization and Maillard reaction kinetics. J Agric Food Chem 47:1786–1793CrossRef

Ajandouz EH, Tchiakpe LS, Dalle Ore F, Benajiba A, Puigserver A (2001) Effects of pH on caramelization and Maillard reaction kinetics in fructose-lysine model systems. J Food Sci 66:926–931CrossRef

Akhtar M, Dickinson E (2007) Whey protein–maltodextrin conjugates as emulsifying agents: an alternative to gum arabic. Food Hydrocoll 21:607–616CrossRef

Allison SD, Chang B, Randolph TW, Carpenter JF (1999) Hydrogen bonding between sugar and protein is responsible for inhibition of dehydration-induced protein unfolding. Arch Biochem Biophys 365:289–298CrossRef

Ames JM (2001) Melanoidins as pro- or antioxidants. Cerevisia 26:210–216

Amici A, Levine RL, Tsai L, Stadtman ER (1989) Conversion of amino acid residues in proteins and amino acid homopolymers to carbonyl derivatives by metal-catalyzed oxidation reactions. J Biol Chem 264:3341–3346

Anderson MM, Hazen SL, Hsu FF, Heinecke JW (1997) Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to convert hydroxyl-amino acids into glycolaldehyde, 2-hydroxypropanol, and acrolein. J Clin Invest 99:424–432CrossRef

Arakawa T, Timasheff SN (1982) Stabilization of protein structure by sugars. Biochemistry 21:6536–6544CrossRef

Ashoor SH, Zent JB (1984) Maillard browning of common amino acids and sugars. J Food Sci 49:1206–1207CrossRef

Back JF, Oakenfull D, Smith MB (1979) Increased thermal stability of proteins in the presence of sugars and polyols. Biochemistry 18:5191–5196CrossRef

Balasundram N, Sundram K, Samman S (2006) Phenolic compounds in plants and agri-industrial by-products: Antioxidant activity, occurrence, and potential uses. Food Chem 99:191–203CrossRef

Ball CD, Hardt CR, Duddles WJ (1943) The influence of sugars on the formation of sulfhydryl groups in heat denaturation and heat coagulation of egg albumin. J Biol Chem 151:163–169

Baskol G, Demir H, Baskol M, Kilic E, Ates F, Karakukcu C, Ustdal M (2006) Investigation of protein oxidation and lipid peroxidation in patients with rheumatoid arthritis. Cell Biochem Funct 24:307–311CrossRef

Baxter JH (1995) Free amino acid stability in reducing sugar systems. J Food Sci 60:405–408CrossRef

Bedell-Hogan D, Trackman P, Abrams W, Rosenbloom J, Kagan H (1993) Oxidation, cross-linking, and insolubilization of recombinant tropoelastin by purified lysyl oxidase. J Biol Chem 268:10345–10350

Beisswenger PJ, Moore LL, Brinck-Johnsen T, Curphey TJ (1993) Increased collagen-linked pentosidine levels and advanced glycosylation end products in early diabetic nephropathy. J Clin Invest 92:212–217CrossRef

Bell LN (1996) Kinetics of non-enzymatic browning in amorphous solids systems: distinguishing the effects of water activity and the glass transition. Food Res Int 28:591–597CrossRef

Bell LN (1997) Maillard reaction as influenced by buffer type and concentration. Food Chem 59:143–147CrossRef

Benjakul S, Visessanguan W, Phongkanpai V, Tanaka M (2005) Antioxidative activity of caramelisation products and their preventive effect on lipid oxidation in fish mince. Food Chem 90:231–239CrossRef

Benjamin O, Silcock P, Leus M, Everett DW (2012) Multilayer emulsions as delivery systems for controlled release of volatile compounds using pH and salt triggers. Food Hydrocoll 27:109–118CrossRef

Berlett BS, Stadtman ER (1997) Protein oxidation in aging, disease, and oxidative stress. J Biol Chem 272:20313–20316CrossRef

Bhoit-Solomon V, Kessler-Icekson G, Shaklai N (1992) Peroxidative crosslinking of myosins. Biochem Int 26:181–189

Boye JI, Alli I (2000) Thermal denaturation of mixtures of α-lactalbumin and β-lactoglobulin: a differential scanning calorimetric study. Food Res Int 33:673–682CrossRef

Breitling-Utzmann CM, Unger A, Friedl DA, Lederer MO (2001) Identification and quantification of phosphatidylethanolamine-derived glucosylamines and aminoketoses from human erythrocytes-influence of glycation products on lipid peroxidation. Arch Biochem Biophys 391:245–254CrossRef

Briganti S, Picardo M (2003) Antioxidant activity, lipid peroxidation and skin diseases. What’s new? J Eur Acad Dermatol Venereol 17:663–669CrossRef

Bucala R, Makita Z, Koschinsky T, Cerami A, Vlassara H (1993) Lipid advanced glycosylation: pathway of lipid oxidation in vivo. Proc Natl Acad Sci U S A 90:6434–6438CrossRef

Buera MP, Karel M (1995) Effect of physical changes on the rates of nonenzymatic browning and related reactions. Food Chem 52:167–173CrossRef

Buera P, Schebor C, Elizalde B (2005) Effects of carbohydrate crystallization on stability of dehydrated foods and ingredient formulations. J Food Eng 67:157–165CrossRef

Bunn HF, Higgins PJ (1981) Reaction of monosaccharides with proteins: possible evolutionary significances. Science 213:222–224CrossRef

Burin L, Jouppila K, Roos YH, Kansikas J, Buera MP (2004) Retention of β-galactosidase activity as related to Maillard reaction, lactose crystallization, collapse and glass transition in low moisture whey systems. Int Dairy J 14:517–525CrossRef

Butterfield DA, Kanski J (2001) Brain protein oxidation in age-related neurodegenerative disorders that are associated with aggregated proteins. Mech Ageing Dev 122:945–962CrossRef

Caliskan G, Lim ASL, Roos YH (2015) Beta-carotene stability in extruded snacks produced using interface engineered emulsions. Int J Food Prop 18:2256–2267CrossRef

Carney JM, Starke-Reed PE, Oliver CN, Landum RW, Cheng MS, Wu JF, Floyd RA (1991) Reversal of age-related increase in brain protein oxidation, decrease in enzyme activity, and loss in temporal and spatial memory by chronic administration of the spin-trapping compound N-tert-butyl-alpha-phenylnitrone. Proc Natl Acad Sci U S A 88:3633–3636CrossRef

Carpenter JF, Crowe JH (1989) An infrared spectroscopic study of the interactions of carbohydrates with dried proteins. Biochemistry 28:3916–3922CrossRef

Carpenter JF, Crowe LM, Crowe JH (1987) Stabilization of phosphofructokinase with sugars during freeze-drying: characterization of enhanced protection in the presence of divalent cations. Biochim Biophys Acta 923:109–115CrossRef

Cervato G, Cazzola R, Cestaro B (1999) Studies on the antioxidant activity of milk caseins. Int J Food Sci Nutr 50:291–296CrossRef

Chao C-C, Ma Y-S, Stadtman ER (1997) Modification of protein surface hydrophobicity and methionine oxidation by oxidative systems. Proc Natl Acad Sci U S A 94:2969–2974CrossRef

Chen S-L, Yang D-J, Chen H-Y, Liu S-C (2009) Effect of hot acidic fructose solution on caramelisation intermediates including colour, hydroxymethylfurfural and antioxidative activity changes. Food Chem 114:582–588CrossRef

Chen Y-J, Liang L, Liu X-M, Labuza TP, Zhou P (2012) Effect of fructose and glucose on glycation of β-lactoglobulin in an intermediate-moisture food model system: analysis by liquid chromatography-mass spectrometry (LC-MS) and data-independent acquisition LC-MS (LC-MS^E). J Agric Food Chem 60:10674–10682CrossRef

Chio KS, Tappel AL (1969) Inactivation of ribonuclease and other enzymes by peroxidizing lipids and by malonaldehyde. Biochemistry 8:2827–2832CrossRef

Coenen JWE (1976) Hydrogenation of edible oils. J Am Oil Chemists’ Soc 53:382–389CrossRef

Colaco CA, Roser BJ (1994) Atherosclerosis and glycation. BioEssays 16:145–147CrossRef

Colbert LB, Decker EA (1991) Antioxidant activity of an ultrafiltration permeate from acid whey. J Food Sci 56:1248–1250CrossRef

Creeth JM, Cooper B, Donald AS, Clamp JR (1983) Studies of the limited degradation of mucus glycoproteins. The effect of dilute hydrogen peroxide. Biochem J 211:323–332CrossRef

Cucu T, Devreese B, Mestdagh F, Kerkaert B, Meulenaer BD (2011) Protein–lipid interactions during the incubation of whey proteins with autoxidizing lipids. Int Dairy J 21:427–433CrossRef

Dalle-Donne I, Rossi R, Giustarini D, Milzani A, Colombo R (2003) Protein carbonyl groups as biomarkers of oxidative stress. Clin Chim Acta 329:23–38CrossRef

Davies KJA (1987) Protein damage and degradation by oxygen radicals. J Biol Chem 262:9895–9901

Decker EA, Welch B (1990) Role of ferritin as a lipid oxidation catalyst in muscle food. J Agric Food Chem 38:674–677CrossRef

Decker EA, Xiong YL, Calvert JT, Crum AD, Blanchard SP (1993) Chemical, physical, and functional properties of oxidized turkey white muscle myofibrillar proteins. J Agric Food Chem 41:186–189CrossRef

Degenhardt TP, Grass L, Reddy S, Thorpe SR, Diamandis EP, Baynes JW (1997) The serum concentration of the advanced glycation end product N^ε-(carboxymethyl)lysine is increased in uremia. Kidney Int 52:1064–1067CrossRef

Desobry SA, Netto FM, Labuza TP (1999) Influence of maltodextrin systems atan equivalent 25DE on encapsulated β-carotene loss during storage. J Food Process Preserv 23:39–55CrossRef

Desorbry SA, Netto FM, Labuza TP (1997) Comparison of spray-drying, drum drying and freeze-drying for β-carotene encapsulation and preservation. J Food Sci 62:1158–1162CrossRef

Dhuique-Mayer C, Tbatou M, Carail M, Caris-Veyrat C, Dornier M, Amiot MJ (2007) Thermal degradation of antioxidant micronutrients in citrus juice: kinetics and newly formed compounds. J Agric Food Chem 55:4209–4216CrossRef

Dills WL (1993) Protein fructosylation: fructose and the Maillard reaction. Am J Clin Nutr 58:779S–787S

Drusch S, Serfert Y, Van Den Heuvel A, Schwarz K (2006) Physicochemical characterization and oxidative stability of fish oil encapsulated in an amorphous matrix containing trehalose. Food Res Int 39:807–815CrossRef

Dyer DG, Blackledge JA, Thorpe SR, Baynes JW (1991) Formation of pentosidine during nonenzymatic browning of proteins by glucose. Identification of glucose and other carbohydrates as possible precursors of pentosidine in vivo. J Biol Chem 266:11654–11660

Dyer DG, Dunn JA, Thorpe SR, Bailie KE, Lyons TJ, McCance DR, Baynes JW (1993) Accumulation of Maillard reaction products in skin collagen in diabetes and aging. J Clin Invest 91:2463–2469CrossRef

Easa AM, Hill SE, Mitchell JR, Taylor AJ (1996) Bovine serum albumin gelation as a result of the Maillard reaction. Food Hydrocoll 10:199–202CrossRef

Edelman R, Kusner I, Kisiliak R, Srebnik S, Livney YD (2015) Sugar stereochemistry effects on water structure and on protein stability: the templating concept. Food Hydrocoll 48:27–37CrossRef

Emken EA (1984) Nutrition and biochemistry of trans and positional fatty acid isomers in hydrogenated oils. Ann Rev Nutr 4:339–376CrossRef

Farombi EO, Britton G (1999) Antioxidant activity of palm oil carotenes in organic solution: effects of structure and chemical reactivity. Food Chem 64:315–321CrossRef

Fox M, Loncin M, Weiss M (1983) Investigations into the influence of water activity, pH and heat treatment on the velocity of the Maillard reaction in foods. J Food Qual 6:103–118CrossRef

Fry LK, Stegink LD (1982) Formation of Maillard reaction products in parenteral alimentation solutions. J Nutr 112:1631–1637

Fu M-X, Knecht KJ, Thorpe SR, Baynes JW (1992) Role of oxygen in cross-linking and chemical modification of collagen by glucose. Diabetes 41:42–48CrossRef

Funes JA, Weiss U, Karel M (1982) Effects of reaction conditions and reactant concentrations on polymerization of lysozyme reacted with peroxidizing lipids. J Agric Food Chem 30:1204–1208CrossRef

Gabarra P, Hartel RW (1998) Corn syrup solids and their saccharide fractions affect crystallization of amorphous sucrose. J Food Sci 63:523–528CrossRef

Garrison WM (1987) Reaction mechanisms in the radiolysis of peptides, polypeptides, and proteins. Chem Rev 87:381–398CrossRef

Gebicki S, Gebicki JM (1993) Formation of peroxides in amino acids and proteins exposed to oxygen free radicals. Biochem J 289:743–749CrossRef

Ghanem AA, Elewa A, Arafa LF (2011) Pentosidine and N-carboxymethyl-lysine: Biomarkers for type 2 diabetic retinopathy. Eur J Opthalmol 21:48–54CrossRef

Gökmen V, Şenyuva HZ (2007) Acrylamide formation is prevented by divalent cations during the Maillard reaction. Food Chem 103:196–203CrossRef

Gomyo T, Horikoshi M (1976) On the interaction of melanoidin with metallic ions. Agric Biol Chem 40:33–40

Grandhee SK, Monnier VM (1991) Mechanism of formation of the Maillard protein cross-link pentosidine. J Biol Chem 266:11649–11653

Greene BE (1969) Lipid oxidation and pigment changes in raw beef. J Food Sci 34:110–113CrossRef

Gu YS, Decker EA, McClements DJ (2005) Production and characterization of oil-in-water emulsions containing droplets stabilized by multilayer membranes consisting of β-lactoglobulin, ι-carrageenan and gelatin. Langmuir 21:5752–5760CrossRef

Gutteridge JMC, Paterson SK, Segal AW, Halliwell B (1981) Inhibition of lipid peroxidation by the iron-binding protein lactoferrin. Biochem J 199:259–261CrossRef

Handa A, Kuroda N (1999) Functional improvements in dried egg white through Maillard reaction. J Agric Food Chem 47:1845–1850CrossRef

Harnkarnsujarit N, Charoenrein S, Roos YH (2012) Reversed phase HPLC analysis of stability and microstructural effects on degradation kinetics of β-carotene encapsulated in freeze-dried maltodextrin–emulsion systems. J Agric Food Chem 60:9711–9718CrossRef

Harnsilawat T, Pongsawatmanit R, McClements DJ (2006) Influence of pH and ionic strength on formation and stability of emulsions containing oil droplets coated by β-lactoglobulin–alginate interfaces. Biomacromolecules 7:2052–2058CrossRef

Hayase F, Nagarai RH, Miyata S, Njoroge FG, Monnier VM (1989) Aging of proteins: immunological detection of a glucose-derived pyrrole formed during Maillard reaction in vivo. J Biol Chem 263:3758–3764

Hayase F, Shibuya T, Sato J, Yamamoto M (1996) Effects of oxygen and transition metals on the advanced Maillard reaction of proteins with glucose. Biosci Biotech Biochem 60:1820–1825CrossRef

Henry LK, Catignani GL, Schwartz SJ (1998) Oxidative degradation kinetics of lycopene, lutein, and 9-cis and all-trans-carotene. J Am Oil Chem Soc 75:823–829CrossRef

Hidalgo A, Brandolini A (2008) Kinetics of carotenoids degradation during the storage of einkorn (Triticum monococcum L. ssp. monococcum) and bread wheat (Triticum aestivum L. ssp. aestivum) flours. J Agric Food Chem 56:11300–11305CrossRef

Hidalgo FJ, Kinsella JE (1989) Changes induced in β-lactoglobulin B following interactions with linoleic acid 13-hydroperoxide. J Agric Food Chem 37:860–866CrossRef

Hidalgo FJ, Zamora R (2000) The role of lipids in nonenzymatic browning. Grasas Aceites 51:35–49CrossRef

Hildebrand JH (1952) The temperature dependence of the solubility of solid nonelectrolytes. J Chem Phys 20:190–191CrossRef

Hirata K, Kubo K (2004) Relationship between blood levels of N-carboxymethyl-lysine and pentosidine and the severity of microangiopathy in type 2 diabetes. Endocr J 51:537–544CrossRef

Hodge JE (1953) Dehydrated foods, chemistry of browning reactions in model systems. J Agric Food Chem 1:928–943CrossRef

Horiuchi S (1996) Advanced glycation end products (AGE)-modified proteins and their potential relevance to atherosclerosis. Trends Cardiovasc Med 6:163–168CrossRef

Hu M, McClements DJ, Decker EA (2003) Lipid oxidation in corn oil-in-water emulsions stabilized by casein, whey protein isolate, and soy protein isolate. J Agric Food Chem 51:1696–1700CrossRef

Jakobsen M, Bertelsen G (2000) Colour stability and lipid oxidation of fresh beef. Development of a response surface model for predicting the effects of temperature, storage time, and modified atmosphere composition. Meat Sci 54:49–57CrossRef

Jones LS, Kaufmann A, Middaugh CR (2005) Silicone oil induced aggregation of proteins. J Pharm Sci 94:918–927

Kanner J, Karel M (1976) Changes in lysozyme due to reactions with peroxidizing methyl linoleate in a dehydrated model system. J Agric Food Chem 24:468–472CrossRef

Karel M (1973) Protein–lipid interactions. J Food Sci 38:756–763CrossRef

Karel M, Schaich K, Roy RB (1975) Interaction of peroxidizing methyl linoleate with some proteins and amino acids. J Agric Food Chem 23:159–163CrossRef

Karmas R, Buera MP, Karel M (1992) Effect of glass transition on rates of nonenzymatic browning in food systems. J Agric Food Chem 40:873–879CrossRef

Kato Y, Watanabe K, Sato Y (1981) Effect of Maillard reaction on some physical properties of ovalbumin. J Food Sci 46:1835–1839CrossRef

Kato Y, Matsuda T, Kato N, Watanabe K, Nakamura R (1986) Browning and insolubilization of ovalbumin by the Maillard reaction with some aldohexoses. J Agric Food Chem 34:351–355CrossRef

Kato H, Cho RK, Okitani A, Hayase F (1987) Responsibility of 3-deoxyglucosone for the glucose-induced polymerization of proteins. J Agric Biol Chem 51:683–689

Kato Y, Matsuda T, Kato N, Nakamura R (1989) Maillard reaction of disaccharides with protein: suppressive effect of nonreducing end pyranoside groups on browning and protein polymerization. J Agric Food Chem 37:1077–1081CrossRef

Kella NKD, Poola I (1985) Sugars decrease the thermal denaturation and aggregation of arachin. Int J Pept Protein Res 26:390–399CrossRef

Khoo HE, Prasad KN, Kong KW, Jiang Y, Ismail A (2011) Carotenoids and their isomers: color pigments in fruits and vegetables. Molecules 16:1710–1738CrossRef

Kinsella JE, Whitehead DM (1989) Proteins in whey: chemical, physical, and functional properties. Adv Food Nutr Res 33:343–438CrossRef

Kirigaya N, Kato H, Fujimaki M (1968) Studies on antioxidant activity of nonenzymatic browning reaction products. Agric Biol Chem 32:287–290

Koch RB (1962) Dehydrated foods and model systems. In Symposium on Foods: Lipids and Their Oxidation. Shultz HW, Day EA, Sinnhuber RO Eds., AVI, Westport, Connecticut, USA, Chapter 13, pp. 230–251

Kouassi K, Roos YH (2001) Glass transition and water effects on sucrose inversion in non-crystalline carbohydrate food systems. Food Res Int 34:895–901CrossRef

Krokida MK, Oreopoulou V, Maroulis ZB (2000) Water loss and oil uptake as a function of frying time. J Food Eng 44:39–46CrossRef

Kwak E-J, Lim S-I (2004) The effect of sugar, amino acid, metal ion, and NaCl on model Maillard reaction under pH control. Amino Acids 27:85–90CrossRef

Labuza TP, Dugan LR Jr (1971) Kinetics of lipid oxidation in foods. CRC Crit Rev Food Technol 2:355–405CrossRef

Labuza TP, Saltmarch M (1981) Kinetics of browning and protein quality loss in whey powders during steady state and nonsteady state storage conditions. J Food Sci 47:92–96CrossRef

Labuza TP, Tsuyuki H, Karel M (1969) Kinetics of linoleate oxidation in model systems. J Am Oil Chem Soc 46:409–416CrossRef

Labuza TP, McNally L, Gallagher D, Hawkes J, Hurtado F (1972) Stability of intermediate moisture foods. 1. Lipid oxidation. J Food Sci 37:154–159CrossRef

Lavelli V, Zanoni B, Zaniboni A (2007) Effect of water activity on carotenoid degradation in dehydrated carrots. Food Chem 104:1705–1711CrossRef

Leake L, Karel M (1982) Polymerization and denaturation of lysozyme exposed to peroxidizing lipids. J Food Sci 47:737–739CrossRef

Levi G, Karel M (1995) Volumetric shrinkage (collapse) in freeze-dried carbohydrates above their glass transition temperature. Food Res Int 28:145–151CrossRef

Lewis VM, Lea CH (1950) A note on the relative rates of reaction of several reducing sugars and sugar derivatives with casein. Biochim Biophys Acta 4:532–534CrossRef

Lievonen SM, Laaksonen TJ, Roos YH (1998) Glass transition and reaction rates: nonenzymatic browning in glassy and liquid systems. J Agric Food Chem 46:2778–2784CrossRef

Liggins J, Furth AJ (1997) Role of protein-bound carbonyl groups in the formation of advanced glycation endproducts. Biochim Biophys Acta 1361:123–130CrossRef

Lim ASL, Roos YH (2016) Spray drying of high hydrophilic solids emulsions with layered interface and trehalose-maltodextrin as glass formers for carotenoids stabilization. J Food Eng 171:174–184CrossRef

Lim ASL, Griffin C, Roos YH (2014) Stability and loss kinetics of lutein and β-carotene encapsulated in freeze-dried emulsions with layered interface and trehalose as glass former. Food Res Int 62:403–409CrossRef

Liu G, Xiong YL (2000) Electrophoretic pattern, thermal denaturation, and in vitro digestibility of oxidized myosin. J Agric Food Chem 48:624–630CrossRef

Liu G, Xiong YL, Butterfield DA (2000) Chemical, physical, and gel-forming properties of oxidized myofibrils and whey- and soy-protein isolates. J Food Sci 65:811–818CrossRef

Liu SC, Lin JT, Yang DJ (2009a) Determination of cis- and trans-α- and β-carotenoids in taiwanese sweet potatoes (Ipomoea batatas (L.) Lam.) harvested at various times. Food Chem 116:605–610CrossRef

Liu X, Zhou P, Tran A, Labuza TP (2009b) Effects of polyols on the stability of whey proteins in intermediate-moisture food model systems. J Agric Food Chem 57:2339–2345CrossRef

Loveday SM, Hindmarsh JP, Creamer LK, Singh H (2009) Physicochemical changes in a model protein bar during storage. Food Res Int 42:798–806CrossRef

Lund MN, Luxford C, Skibsted LH, Davies MJ (2008) Oxidation of myosin by haem proteins generates myosin radicals and protein cross-links. Biochem J 410:565–574CrossRef

Lyons TJ (1993) Glycation and oxidation: a role in the pathogenesis of atherosclerosis. Am J Cardiol 71:26–31CrossRef

Mahfoudhi N, Hamdi S (2014) Kinetic degradation and storage stability of β-carotene encapsulated by spray drying using almond gum and gum arabic as wall materials. J Polym Eng 34:683–693

Mahfoudhi N, Hamdi S (2015) Kinetic degradation and storage stability of β-carotene encapsulated by freeze-drying using almond gum and gum arabic as wall materials. J Food Process Preserv 39:896–906CrossRef

Makita Z, Radoff S, Rayfield EJ, Yang Z, Skolnik E, Delaney V, Friedman EA, Cerami A, Vlassara H (1991) Advanced glycosylation end products in patients with diabetic nephropathy. N Engl J Med 325:836–842CrossRef

Makris DP, Rossiter JT (2000) Heat-induced, metal-catalyzed oxidative degradation of quercetin and rutin (quercetin 3-o-rhamnosylglucoside) in aqueous model systems. J Agric Food Chem 48:3830–3838CrossRef

Markesbery WR, Lovell MA (1998) Four-hydroxynonenal, a product of lipid peroxidation, is increased in the brain in Alzheimer’s disease. Neurobiol Aging 19:33–36CrossRef

Mastrocola D, Munari M (2000) Progress of the Maillard reaction and antioxidant action of Maillard reaction products in preheated model systems during storage. J Agric Food Chem 48:3555–3559CrossRef

Mastrocola D, Munari M, Cioroi M, Lerici CR (2000) Interaction between Maillard reaction products and lipid oxidation in starch-based model systems. J Sci Food Agric 80:684–690CrossRef

Mazzobre MF, Buera MP, Chirife J (1997) Protective role of trehalose on thermal stability of lactase in relation to its glass and crystal forming properties and effect of delaying crystallization. Lebensm Wiss Technol 30:324–329CrossRef

McCance DR, Dyer DG, Dunn JA, Bailie KE, Thorpe SR, Baynes JW, Lyons TJ (1993) Maillard reaction products and their relation to complications in insulin-dependent diabetes mellitus. J Clin Invest 91:2470–2478CrossRef

McPherson JD, Shilton BH, Walton DJ (1988) Role of fructose in glycation and cross-linking of proteins. Biochemistry 27:1901–1907CrossRef

Meucci E, Mordente A, Martorana GE (1991) Metal-catalyzed oxidation of human serum albumin: conformational and functional changes. Implications in protein aging. J Biol Chem 266:4692–4699

Miyata T, Ueda Y, Yamada Y, Izuhara Y, Wada T, Jadoul M, Saito A, Kurokawa K, van Ypersele de Strihou C (1998) Accumulation of carbonyls accelerates the formation of pentosidine, an advanced glycation end product: carbonyl stress in uremia. J Am Soc Nephrol 9:2349–2356

Molnar-Perl I, Friedman M (1990) Inhibition of browning by sulfur amino acids. 2. Fruit juices and protein-containing foods. J Agric Food Chem 38:1648–1651CrossRef

Monnier VM (1990) Nonenzymatic glycosylation, the Maillard reaction and the aging process. J Gerontol 45:105–111CrossRef

Morcira RG, Sun X, Chen Y (1997) Factors affecting oil uptake in tortilla chips in deep-fat frying. J Food Eng 31:485–498CrossRef

Moreau L, Kim H-J, Decker EA, McClements DJ (2003) Production and characterization of oil-in-water emulsions containing droplets stabilized by β-lactoglobulin–pectin membranes. J Agric Food Chem 51:6612–6617CrossRef

Morita J, Kashimura N (1991) The Maillard reaction of DNA with d-fructose 6-phosphate. Agric Biol Chem 55:1359–1366

Mulvihill DM, Donovan M (1987) Whey proteins and their thermal denaturation—a review. Ir J Food Sci Technol 11:43–75

Mulvihill DM, Kinsella JE (1987) Gelation characteristics of whey proteins and beta-lactoglobulin. Food Technol. 41:102–111

Negre-Salvayre A, Coatrieux C, Ingueneau C, Salvayre R (2008) Advanced lipid peroxidation end products in oxidative damage to proteins. Potential role in diseases and therapeutic prospects for the inhibitors. Br J Pharmacol 153:6–20CrossRef

Nielsen HK, Löliger J, Hurrell RF (1985) Reactions of proteins with oxidizing lipids. Br J Nutr 53:61–73CrossRef

Nursten HE (1981) Recent developments in studies of the Maillard reaction. Food Chem 6:263–277CrossRef

Oliver CN, Ahn B-W, Moerman EJ, Goldstein S, Stadtman ER (1987) Age-related changes in oxidized proteins. J Biol Chem 262:5488–5491

Ordonez JA, Ledward DA (1977) Lipid and myoglobin oxidation in pork stored in oxygen- and carbon dioxide-enriched atmospheres. Meat Sci 1:41–48CrossRef

Ortwerth BJ, Olesen PR (1988) Ascorbic acid-induced crosslinking of lens proteins: evidence supporting a Maillard reaction. Biochim Biophys Acta 956:10–22CrossRef

Öste RE, Dahlqvist A, Sjöström H, Norén O, Miller R (1986) Effect of Maillard reaction products on protein digestion. In vitro studies. J Agric Food Chem 34:355–358CrossRef

Peña-Ramos EA, Xiong YL (2003) Whey and soy protein hydrolysates inhibit lipid oxidation in cooked pork patties. Meat Sci 64:259–263CrossRef

Pilková L, Pokorný J, Davídek J (1990) Browning reactions of Heyns rearrangement products. Nahrung 34:759–764CrossRef

Pinnell SR, Martin GR (1968) The cross-linking of collagen and elastin: enzymatic conversion of lysine in peptide linkage to α-aminoadipic-δ-semialdehyde (allysine) by an extract from bone. Proc Natl Acad Sci U S A 61:708–716CrossRef

Pinthus EJ, Weinberg P, Saguy IS (1995) Oil uptake in deep fat frying as affected by porosity. J Food Sci 60:767–769CrossRef

Plachta H, Bartnikowska E, Obara A (1992) Lipid peroxides in blood from patients with atherosclerosis of coronary and peripheral arteries. Clin Chem Acta 211:101–112CrossRef

Pomeranz Y, Johnson JA, Shellenberger JA (1962) Effect of various sugars on browning. J Food Sci 27:350–354CrossRef

Potes N, Kerry JP, Roos YH (2012) Additivity of water sorption, alpha-relaxations and crystallization inhibition in lactose–maltodextrin systems. Carbohyd Polym 89:1050–1059CrossRef

Potes N, Kerry JP, Roos YH (2013) Oil as reaction medium for glycation, oxidation, denaturation, and aggregation of whey protein systems of low water activity. J Agric Food Chem 61:3748–3756CrossRef

Potes N, Kerry JP, Roos YH (2014) Protein modifications in high protein–oil and protein–oil–sugar systems at low water activity. Food Biophys 9:49–60CrossRef

Qiu D, Chen ZH, Li HR (2009) Effect of heating on solid β-carotene. Food Chem 112:344–349CrossRef

Quast DG, Karel M (1972) Effects of environmental factors on the oxidation of potato chips. J Food Sci 37:584–588CrossRef

Ramoneda XA, Ponce-Cevallos PA, Buera MP, Elizalde BE (2011) Degradation of β-carotene in amorphous polymer matrices. Effect of water sorption properties and physical state. J Sci Food Agr 91:2587–2593CrossRef

Ré MI (1998) Microencapsulation by spray-drying. Dry Technol 16:1195–1236CrossRef

Reddy S, Bichler J, Wells-Knecht KJ, Thorpe SR, Baynes JW (1995) N ^ε-(carboxymethyl)lysine is a dominant advanced glycation end product (AGE) antigen in tissue proteins. Biochemistry 34:10872–10878CrossRef

Refsgaard HHF, Tsai T, Stadtman ER (2000) Modifications of proteins by polyunsaturated fatty acid peroxidation products. Proc Natl Acad Sci U S A 97:611–616CrossRef

Remig V, Franklin B, Margolis S, Kostas G, Nece T, Street JC (2010) Trans fats in America: a review of their use, consumption, health implications, and regulation. J Am Diet Assoc 110:585–592CrossRef

Requena JR, Fu M-X, Ahmed MU, Jenkins AJ, Lyons TJ, Thorpe SR (1996) Lipoxidation products as biomarkers of oxidative damage to proteins during lipid peroxidation reactions. Nephrol Dial Transplant 11:48–53CrossRef

Requena JR, Chao C-C, Levine RL, Stadtman ER (2001) Glutamic and aminoadipic semialdehydes are the main carbonyl products of metal-catalyzed oxidation of proteins. Proc Natl Acad Sci U S A 98:69–74CrossRef

Rhee KS, Ziprin YA, Ordonez G (1987) Catalysis of lipid oxidation in raw and cooked beef by metmyoglobin-H₂O₂, nonheme iron, and enzyme systems. J Agric Food Chem 35:1013–1017CrossRef

Rice-Evans CA, Miller NJ, Paganga G (1997) Antioxidant properties of phenolic compounds. Trends Plant Sci 2:152–159CrossRef

Rich LM, Foegeding EA (2000) Effects of sugars on whey protein isolate gelation. J Agric Food Chem 48:5046–5052CrossRef

Richards MP, Hultin HO (2000) Effect of pH on lipid oxidation using trout hemolysate as a catalyst: a possible role for deoxyhemoglobin. J Agric Food Chem 48:3141–3147CrossRef

Rivett AJ, Roseman JE, Oliver CN, Levine RL, Stadtman ER (1985) Covalent modification of proteins by mixed-function oxidation: recognition by intracellular proteases. Prog Clin Biol Res 180:317–328

Roos YH (1993) Water activity and physical state effects on amorphous food stability. J Food Process Preserv 16:433–447

Roos YH (1995a) Glass transition-related physicochemical changes in foods. Food Technol 49:97–102

Roos YH (1995b) Phase transitions in foods. Academic Press Inc, California

Roos Y, Karel M (1991) Plasticizing effect of water on thermal behavior and crystallization of amorphous food models. J Food Sci 56:38–43CrossRef

Roos YH, Jouppila K, Zielasko B (1996a) Non-enzymatic browning-induced water plasticization. J Therm Anal 47:1437–1450CrossRef

Roos Y, Karel M, Kokini JL (1996b) Glass transitions in low moisture and frozen foods: effects on shelf life and quality. Food Technol. 50:95–139

Rouach H, Fataccioli V, Gentil M, French SW, Morimoto M, Nordmann R (1997) Effect of chronic ethanol feeding on lipid peroxidation and protein oxidation in relation to liver pathology. Hepatology 25:351–355CrossRef

Roubal WT (1971) Free radicals, malonaldehyde and protein damage in lipid-protein systems. Lipids 6:62–64CrossRef

Roubal WT, Tappel AL (1966a) Damage to proteins, enzymes, and amino acids by peroxidizing lipids. Arch Biochem Biophys 113:5–8CrossRef

Roubal WT, Tappel AL (1966b) Polymerization of proteins induced by free radical lipid peroxidation. Arch Biochem Biophys 113:150–155CrossRef

Sakanaka S, Tachibana Y, Ishihara N, Juneja LR (2004) Antioxidant activity of egg-yolk hydrolysates in a linoleic acid oxidation system. Food Chem 86:99–103CrossRef

Salman AG, Mansour DE, Swelem AH, AI-Zawahary WM, Radwan AA (2009) Pentosidine—a new biochemical marker in diabetic retinopathy. Ophthalmic Res 42:96–98CrossRef

Sasaki N, Fukatsu R, Tsuzuki K, Hayashi Y, Yoshida T, Fujii N, Koike T, Wakayama I, Yanagihara R, Garruto R, Amano N, Makita Z (1998) Advanced glycation end products in Alzheimer’s disease and other neurodegenerative diseases. Am J Pathol 153:1149–1155CrossRef

Sattar A, deMan JM, Furia TE (1975) Photooxidation of milk and milk products: a review. Crit Rev Food Sci Nutr 7:13–37CrossRef

Sayre LM, Zelasko DA, Harris PLR, Perry G, Salomon RG, Smith MA (1997) 4-hydroxynonenal-derived advanced lipid peroxidation end products are increased in Alzheimer’s disease. J Neurochem 68:2092–2097CrossRef

Schaich KM, Karel M (1976) Free radical reactions of peroxidizing lipids with amino acids and proteins: an ESR study. Lipids 11:392–400CrossRef

Schebor C, Buera MP, Karel M, Chirife J (1999) Color formation due to non-enzymatic browning in amorphous, glassy, anhydrous, model systems. Food Chem 65:427–432CrossRef

Sell DR, Monnier VM (1989) Structure elucidation of a senescence cross-link from human extracellular matrix. J Biol Chem 264:21597–21602

Shacter E (2000) Quantification and significance of protein oxidation in biological samples. Drug Metab Rev 32:307–326CrossRef

Shahidi F, Amarowicz R (1996) Antioxidant activity of protein hydrolyzates from aquatic species. J Am Oil Chem Soc 73:1197–1199CrossRef

Shahidi F, Han XQ (1993) Encapsulation of food ingredients. Crit Rev Food Sci Nutr 33:501–547CrossRef

Sherwin ER (1978) Oxidation and antioxidants in fat and oil processing. J Am Oil Chem Soc 55:809–814CrossRef

Shimada Y, Roos Y, Karel M (1991) Oxidation of methyl linoleate encapsulated in amorphous lactose-based food model. J Agric Food Chem 39:637–641CrossRef

Shinmoto H, Dosako S, Nakajima I (1992) Anti-oxidant activity of bovine lactoferrin on iron/ascorbate induced lipid peroxidation. Biosci Biotech Biochem 12:2079–2080CrossRef

Sims RJ, Fioriti JA, Trumbetas J (1979) Effect of sugars and sugar alcohols on autoxidation of safflower oil in emulsions. J Am Oil Chem Soc 56:742–745CrossRef

Singh R, Barden A, Mori T, Beilin L (2001) Advanced glycation end-products: a review. Diabetologia 44:129–146CrossRef

Slade L, Levine H, Reid DS (1991) Beyond water activity: recent advances based on an alternative approach to the assessment of food quality and safety. Crit Rev Food Sci Nutr 30:115–360CrossRef

Smith CD, Carney JM, Starke-Reed PE, Oliver CN, Stadtman ER, Floyd RA, Markesbery WR (1991) Excess brain protein oxidation and enzyme dysfunction in normal aging and in Alzheimer disease. Proc Natl Acad Sci U S A 88:10540–10543CrossRef

Smith MA, Taneda S, Richey PL, Miyata S, Yan S-D, Stern D, Sayre LM, Monnier VM, Perry G (1994) Advanced Maillard reaction end products are associated with Alzheimer disease pathology. Proc Natl Acad Sci U S A 91:5710–5714CrossRef

Spiteller G (2005) The relation of lipid peroxidation processes with atherogenesis: a new theory on atherogenesis. Mol Nutr Res 49:999–1013CrossRef

Stadler RH, Blank I, Varga N, Robert F, Hau J, Guy PA, Robert M-C, Riediker S (2002) Food chemistry: acrylamide from Maillard reaction products. Nature 419:449–450CrossRef

Stadtman ER (1992) Protein oxidation and aging. Science 257:1220–1224CrossRef

Stadtman ER (2001) Protein oxidation in aging and age-related diseases. Ann NY Acad Sci 928:22–38CrossRef

Stadtman ER, Berlett BS (1998) Reactive oxygen-mediated protein oxidation in aging and disease. Drug Metab Rev 30:225–243CrossRef

Stadtman ER, Levine RL (2000) Protein oxidation. Ann NY Acad Sci 899:191–208CrossRef

Stadtman ER, Levine RL (2003) Free radical-mediated oxidation of free amino acids and amino acid residues in proteins. Amino Acids 25:207–218CrossRef

Stadtman ER, Starke-Reed PE, Oliver CN, Carney JM, Floyd RA (1992) Protein modification in aging. EXS 62:64–72

Stapelfeldt H, Nielsen BoR, Skibsted LH (1997) Effect of heat treatment, water activity and storage temperature on the oxidative stability of whole milk powder. Int Dairy J 7:331–339CrossRef

Starke-Reed PE, Oliver CN (1989) Protein oxidation and proteolysis during aging and oxidative stress. Arch Biochem Biophys 275:559–567CrossRef

Stringer MD, Görög PG, Freeman A, Kakkar VV (1989) Lipid peroxides and atherosclerosis. Br Med J 298:281–284CrossRef

Suetsuna K, Ukeda H, Ochi H (2000) Isolation and characterization of free radical scavenging activities peptides derived from casein. J Nutr Biochem 11:128–131CrossRef

Sun Q, Senecal A, Chinachoti P, Faustman C (2002) Effect of water activity on lipid oxidation and protein solubility in freeze-dried beef during storage. J Food Sci 67:2512–2516CrossRef

Tenada S, Monnier VM (1994) ELISA of pentosidine, an advanced glycation end product, in biological specimens. Clin Chem 40:1766–1773

Tewa-Tagne P, Briançon S, Fessi H (2007) Preparation of redispersible dry nanocapsules by means of spray-drying: development and characterisation. Eur J Pharm Sci 30:124–135CrossRef

Thornalley PJ, Langborg A, Minhas HS (1999) Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose. Biochem J 344:109–116CrossRef

Uchida K, Stadtman ER (1992) Modification of histidine residues in proteins by reaction with 4-hydroxynonenal. Proc Natl Acad Sci U S A 89:4544–4548CrossRef

Uchida K, Kato Y, Kawakishi S (1990) A novel mechanism for oxidative cleavage of prolyl peptides induced by the hydroxyl radical. Biochem Biophys Res Commun 169:265–271CrossRef

Updike AA, Schwartz SJ (2003) Thermal processing of vegetables increases cis isomers of lutein and zeaxanthin. J Agric Food Chem 51:6184–6190CrossRef

Uribarri J, Woodruff S, Goodman S, Cai W, Chen X, Pyzik R, Yong A, Striker GE, Vlassara H (2010) Advanced glycation end products in foods and a practical guide to their reduction in the diet. J Am Diet Assoc 110:911–916CrossRef

van Het Hof KH, West CE, Weststrate JA, Hautvast JG (2000) Dietary factors that affect the bioavailability of carotenoids. J Nutr 130:503–506

Venolia AW, Tappel AL (1958) Brown-colored oxypolymers of unsaturated fats. J Am Oil Chem Soc 35:135–138CrossRef

Voziyan PA, Hudson BG (2005) Pyridoxamine: the many virtues of a Maillard reaction inhibitor. Ann NY Acad Sci 1043:807–816CrossRef

Wang H, Qian H, Yao W (2011) Melanoidins produced by the Maillard reaction: structure and biological activity. Food Chem 128:573–584CrossRef

Watanabe K, Sato Y, Kato Y (1980) Chemical and conformational changes of ovalbumin due to the Maillard reaction. J Food Process Preserv 3:263–274CrossRef

Wells-Knecht KJ, Zyzak DV, Litchfield JE, Thorpe SR, Baynes JW (1995) Mechanism of autoxidative glycosylation: identification of glyoxal and arabinose as intermediates in the autoxidative modification of proteins by glucose. Biochemistry 34:3702–3709CrossRef

Wilhelm E, Battino R, Wilcock RJ (1977) Low-pressure solubility of gases in liquid water. Chem Rev 77:219–262CrossRef

Williams AW, Boileau TWM, Erdman JW (1998) Factors influencing the uptake and absorption of carotenoids. Exp Biol Med 218:106–108CrossRef

Wishner LA (1964) Light-induced oxidations in milk. J Dairy Sci 47:216–221CrossRef

Wolfrom ML, Kashimura N, Horton D (1974) Factors affecting the Maillard browning reaction between sugars and amino acids. Studies on the nonenzymic browning of dehydrated orange juice. J Agric Food Chem 22:796–800CrossRef

Wu W, Wu X, Hua Y (2010) Structural modification of soy protein by the lipid peroxidation product acrolein. Lebensm Wiss Technol 43:133–140CrossRef

Yagi K (1987) Lipid peroxides and human diseases. Chem Phys Lipids 45:337–351CrossRef

Yeboah FK, Alli I, Yaylayan VA (1999) Reactivities of d-glucose and d-fructose during glycation of bovine serum albumin. J Agric Food Chem 47:3164–3172CrossRef

Yen G-C, Hsieh P-P (1995) Antioxidant activity and scavenging effects on active oxygen of xylose-lysine Maillard reaction products. J Sci Food Agric 67:415–420CrossRef

Yilmaz Y, Toledo R (2005) Antioxidant activity of water-soluble Maillard reaction products. Food Chem 93:273–278CrossRef

Zamora R, Hidalgo FJ (2005) Coordinate contribution of lipid oxidation and Maillard reaction to the nonenzymatic food browning. Crit Rev Food Sci Nutr 45:49–59CrossRef

Zhou P, Guo M, Liu D, Liu X, Labuza TP (2013) Maillard-reaction-induced modification and aggregation of proteins and hardening of texture in protein bar model systems. J Food Sci 78:437–444CrossRef

Zirlin A, Karel M (1969) Oxidation effects in a freeze-dried gelatin-methyl linoleate system. J Food Sci 34:160–165CrossRef

Title: Chemical Stability: Browning and Oxidation
Authors: Naritchaya Potes
Aaron S. L. Lim
Yrjö H. Roos
Publisher: Springer New York
Book: Engineering Foods for Bioactives Stability and Delivery
Print ISBN: 978-1-4939-6593-9

Electronic ISBN: 978-1-4939-6595-3

Copyright Year: 2017
DOI: https://doi.org/10.1007/978-1-4939-6595-3_14