Reducing the potential for processing contaminant formation in cereal products

Journal of Cereal Science

Volumn 59, Issue 3, 2014, Pages 382-392

  Curtis, Tanya Y ^a   Postles, Jennifer ^a   Halford, Nigel G ^a  

^a ROTHAMSTED RESEARCH   (United Kingdom)

Author keywords

Acrylamide; Asparagine; Free amino acids; Furan; Hydroxymethylfurfuryl; Lipid oxidation; Maillard reaction; Processing contaminant; Reducing sugars; Trans fatty acids

Indexed keywords

EID: 84899627145     PISSN: 07335210     EISSN: 10959963     Source Type: Journal    
DOI: 10.1016/j.jcs.2013.11.002     Document Type: Review

References (98)

1. Almeida J.P.F., Hartwig U.A., Frehner M., Nösberger J., Lüscher A. Evidence that P deficiency induces N feedback regulation of symbiotic nitrogen fixation in white clover (Trifolium repensL.). J.Exp. Bot. 2000, 51:1289-1297.
2. Baena-González E., Rolland F., Thevelein J.M., Sheen J. Acentral integrator of transcription networks in plant stress and energy signalling. Nature 2007, 448:938-942.
3. Bakhiya N., Appel K.E. Toxicity and carcinogenicity of furan in human diet. Arch. Toxicol. 2010, 84:563-578.
4. Bassett C.M.C., Edel A.L., Patenaude A.F., McCullough R.S., Blackwood D.P., Chouinard P.Y., Paquin P., Lamarche B., Pierce G.N. Dietary vaccenic acid has antiatherogenic effects in LDLr-/- mice. J.Nutr. 2010, 140:18-24.
5. Blair G.J. Sulphur fertilisers: a global perspective. IFS Proceeding No. 498 2002, The International Fertiliser Society, York.
6. Brouwer A., Wanders A.J., Katan M.B. Effect of animal and industrial trans fatty acids on HDL and LDL cholesterol levels in humans - a quantitative review. PLoS One 2010, 5:e9434.
7. Bushuk W. Physiology of rye. Rye: Production, Chemistry, and Technology 2001, 53-68. American Association of Cereal Chemists, St. Paul, Minn. W. Bushuk (Ed.).
8. Byrne E.H., Prosser I., Muttucumaru N., Curtis T.Y., Wingler A., Powers S., Halford N.G. Overexpression of GCN2-type protein kinase in wheat has profound effects on free amino acid concentration and gene expression. Plant Biotechnol. J. 2012, 10:328-340.
9. Cahoon E.B. Genetic enhancement of soybean oil for industrial uses: prospects and challenges. AgBioForum 2003, 6:11-13.
10. Chawla R., Shakya R., Rommens C.M. Tuber-specific silencing of asparagine synthetase-1 reduces the acrylamide-forming potential of potatoes grown in the field without affecting tuber shape and yield. Plant Biotech. J. 2012, 10:913-924.
11. Claus A., Weisz G.M., Schieber A., Carle R. Pyrolytic acrylamide formation from purified wheat gluten and gluten-supplemented wheat bread rolls. Mol. Nut. Food Res. 2006, 50:87-93.
12. Claus A., Carle R., Schieber A. Acrylamide in cereal products: a review. J.Cereal Sci. 2008, 47:118-133.
13. Costa G., Morel J.L. Water relations, gas exchange and amino acid content in Cd-treated lettuce. Plant Physiol. Biochem. 1994, 32:561-570.
14. Costa G., Spitz R. Influence of cadmium on soluble carbohydrates, free amino acids, protein content of invitro cultured Lupinus albus. Plant Sci. 1997, 128:131-140.
15. Crews C., Castle L. Areview of the occurrence, formation and analysis of furan in heat-processed foods. Trends Food Sci. Technol. 2007, 18:365-372.
16. Curtis T.Y., Muttucumaru N., Shewry P.R., Parry M.A.J., Powers S.J., Elmore J.S., Mottram D.S., Hook S., Halford N.G. Effects of genotype and environment on free amino acid levels in wheat grain: Implications for acrylamide formation during processing. JAgric Food Chem 2009, 57:1013-1021.
17. Curtis T.Y., Powers S.J., Balagiannis D., Elmore J.S., Mottram D.S., Parry M.A.J., Rakszegi M., Bedo Z., Shewry P.R., Halford N.G. Free amino acids and sugars in rye Grain: Implications for acrylamide formation. JAgric Food Chem 2010, 58:1959-1969.
18. De Vleeschouwer K., Van der Plancken I., Van Loey A., Hendrickx M.E. Role of precursors on the kinetics of acrylamide formation and elimination under low moisture conditions using a multiresponse approach - Part I: effect of the type of sugar. Food Chem. 2009, 114:116-126.
19. Elmore J.S., Parker J.K., Halford N.G., Muttucumaru N., Mottram D.S. Effects of plant sulfur nutrition on acrylamide and aroma compounds in cooked wheat. J.Agric. Food Chem. 2008, 56:6173-6179.
20. European Commission Commission Recommendation of 10 January 2011 on Investigations into the Levels of Acrylamide in Food 2011, European Commission, Brussels.
21. European Commission Commission Recommendation of 8 November 2013 on Investigations into the Levels of Acrylamide in Food 2013, European Commission, Brussels.
22. European Food Safety Authority Results on acrylamide levels in food from monitoring years 2007-2009 and exposure assessment. EFSA J. 2011, 9:2133.
23. European Food Safety Authority Update on furan levels in food from monitoring years 2004-2010 and exposure assessment. EFSA J. 2011, 9:2347.
24. European Food Safety Authority Update on acrylamide levels in food from monitoring years 2007-2010. EFSA J. 2012, 10:2938.
25. Fan X., Huang L., Sokorai K.J. Factors affecting thermally-induced furan formation. J.Agric. Food Chem. 2008, 56:9490-9494.
26. Fertiliser Manual Fertiliser Manual (RB209) 2011, with 2011 errata. http://www.defra.gov.uk, eighth ed.
27. Food Drink Europe Acrylamide Toolbox 2011 2011, Food Drink Europe, Brussels.
28. Friedman M. Chemistry, biochemistry and safety of acrylamide. A review. J.Agric. Food Chem. 2003, 51:4504-4526.
29. Friedman M. Biological effects of Maillard browning products that may affect acrylamide safety. Chemistry and Safety of Acrylamide in Food 2005, 135-156. Springer, New York. D.S. Mottram, M. Friedman (Eds.).
30. - into the shoots. J.Exp. Bot. 2005, 56:2365-2378.
31. Good A.G., Zaplachinski S.T. The effects of drought stress on free amino acid accumulation and protein synthesis in Brassica napus. Physiol. Plant 1994, 90:9-14.
32. Granvogl M., Schieberle P. Thermally generated 3-aminopropionamide as a transient intermediate in the formation of acrylamide. J.Agric. Food Chem. 2006, 54:5933-5938.
33. Granvogl M., Wieser H., Koehler P., Von Tucher S., Schieberle P. Influence of sulfur fertilization on the amounts of free amino acids in wheat. Correlation with baking properties as well as with 3-aminopropionamide and acrylamide generation during baking. J.Agric. Food Chem. 2007, 55:4271-4277.
34. Halford N.G. Regulation of carbon and amino acid metabolism: roles of sucrose nonfermenting-1-related protein kinase-1 and general control nonderepressible-2-related protein kinase. Adv. Bot. Res. Incorp. Adv. Plant Pathol. 2006, 43:93-142.
35. Halford N.G., Curtis T.Y., Muttucumaru N., Postles J., Mottram D.S. Sugars in crop plants. Ann. Appl. Biol. 2011, 158:1-25.
36. Halford N.G., Muttucumaru N., Powers S.J., Gillatt P.N., Hartley L., Elmore J.S., Mottram D.S. Concentrations of free amino acids and sugars in nine potato varieties: effects of storage and relationship with acrylamide formation. J.Agric. Food Chem. 2012, 60:12044-12055.
37. Halford N.G., Curtis T.Y., Muttucumaru N., Postles J., Elmore J.S., Mottram D.S. The acrylamide problem: a plant and agronomic science issue. J.Exp. Bot. 2012, 63:2841-2851.
38. Harrigan G.G., Stork L.G., Riordan S.G., Reynolds T.L., Ridley W.P., Masucci J.D., MacIsaac S., Halls S.C., Orth R., Smith R.G., Wen L., Brown W.E., Welsch M., Riley R., McFarland D., Pandravada A., Glenn K.C. Impact of genetics and environment on nutritional and metabolite components of maize grain. J.Agric. Food Chem. 2007, 55:6177-6185.
39. Hendriksen H.V., Kornbrust B.A., Østergaard P.R., Stringer M.A. Evaluating the potential for enzymatic acrylamide mitigation in a range of food products using an asparaginase from Aspergillus oryzae. J.Agric. Food Chem. 2009, 57:4168-4176.
40. Hennekens C.H., Buring J.E. Epidemiology in Medicine 1987, Lippincott Williams and Wilkins, Philadelphia.
41. Hey S.J., Byrne E., Halford N.G. The interface between metabolic and stress signalling. Ann. Bot. 2010, 105:197-203.
42. Hummel M., Rahmani F., Smeekens S., Hanson J. Sucrose-mediated translational control. Annal. Bot. 2009, 104:1-7.
43. Husøy T., Haugen M., Murkovic M., Jöbstl D., Stølen L.H., Bjellaas T., Rønningborg C., Glatt H., Alexander J. Dietary exposure to 5-hydroxymethylfurfural from Norwegian food and correlations with urine metabolites of short-term exposure. Food Chem. Toxicol. 2008, 46:3697-3702.
44. International Agency for Research on Cancer IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Some Industrial Chemicals 1994, vol. 60. International Agency for Research on Cancer (IARC), Lyon.
45. International Agency for Research on Cancer IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Dry-cleaning, Some Chlorinated Solvents and Other Industrial Chemicals 1995, vol. 63. International Agency for Research on Cancer (IARC), Lyon.
46. Joint FAO/WHO Expert Committee on Food Additives (JECFA) Safety Evaluation of Certain Contaminants in Food. WHO Food Additives Series: 63; FAO JECFA Monographs 8 2011, World Health Organization/Food and Agriculture Organization of the United Nations, Geneva/Rome.
47. Joy K.W., Ireland R.J., Lea P.J. Asparagine synthesis in pea leaves, and the occurrence of an asparagine synthetase inhibitor. Plant Physiol. 1983, 73:165-168.
48. Kinney A.J. Genetic engineering of oilseeds for desired traits. Genetic Engineering 1997, vol. 19:149-166. Plenum Press, New York.
49. Kudiyarova Zh.S., Muttucumaru N., West J.S., Halford N.G. Activity of enzymes associated with asparagine synthesis and breakdown in wheat under biotic and abiotic stress conditions. Aspects of Appl. Biol. 2013, 116:119-124.
50. Lageix S., Lanet E., Pouch-Pelissier M.N., Espagnol M.C., Robaglia C., Deragon J.M., Pelissier T. Arabidopsis eIF2α kinase GCN2 is essential for growth in stress conditions and is activated by wounding. BMC Plant Biol. 2008, 8:134-142.
51. Lam H.M., Hsieh M.H., Coruzzi G. Reciprocal regulation of distinct asparagine synthetase genes by light and metabolites in Arabidopsis thaliaPlant Jna. Plant J. 1998, 16:345-353.
52. Lea P.J., Fowden L. The purification and properties of glutamine-dependent asparagine synthetase isolated from Lupinus albus. Proc. Royal Soc. London Series B 1975, 192:13-26.
53. Lea P.J., Sodek L., Parry M.A., Shewry P.R., Halford N.G. Asparagine in plants. Ann. Appl. Biol. 2007, 150:1-26.
54. Leopardi P., Cordelli E., Villani P., Cremona T.P., Conti L., De Luca G., Crebelli R. Assessment of invivo genotoxicity of the rodent carcinogen furan: evaluation of DNA damage and induction of micronuclei in mouse splenocytes. Mutagenesis 2010, 25:57-62.
55. Lipworth L., Sonderman J.S., Tarone R.E., McLaughlin J.K. Review of epidemiologic studies of dietary acrylamide intake and the risk of cancer. Eur. J. Cancer Prev. 2012, 21:375-386.
56. Maillard L.C. Action des acides aminés sur les sucres: formation des mélanoïdines par voie méthodique. Compte-rendu de l'Acad. Sci. 1912, 154:66-68.
57. Märk J., Pollien P., Lindinger C., Blank I., Märk T. Quantitation of furan and methylfuran formed in different precursor systems by proton transfer reaction mass spectrometry. J.Agric. Food Chem. 2006, 54:2786-2793.
58. Martinek P., Klem K., Vanova M., Bartackova V., Vecerkova L., Bucher P., Hajslova J. Effects of nitrogen nutrition, fungicide treatment and wheat genotype on free asparagine and reducing sugars content as precursors of acrylamide formation in bread. Plant Soil Environ. 2009, 55:187-195.
59. Moro S., Chipman J.K., Wegener J.-W., Hamberger C., Dekant W., Mally A. Furan in heat-treated foods: formation, exposure, toxicity, and aspects of risk assessment. Mol. Nut. Food Res. 2012, 56:1197-1211.
60. Mottram D.S., Wedzicha B.L., Dodson A.T. Acrylamide is formed in the Maillard reaction. Nature 2002, 419:448-449.
61. Mottram D.S. The Maillard reaction: source of flavor in thermally processed foods. Flavors and Fragrances: Chemistry, Bioprocessing and Sustainability 2007, 269-284. Springer-Verlag, Berlin. R.G. Berger (Ed.).
62. Mounts T.L., Warner K., List G.R., Neff W.E., Wilson R.F. Low-linolenic acid soybean oils - alternatives to frying oils. J.Am. Oil Chem. Soc. 1994, 71:495-499.
63. Muttucumaru N., Halford N.G., Elmore J.S., Dodson A.T., Parry M., Shewry P.R., Mottram D.S. Formation of high levels of acrylamide during the processing of flour derived from sulfate-deprived wheat. J.Agric. Food Chem. 2006, 54:8951-8955.
64. Muttucumaru N., Elmore J.S., Curtis T., Mottram D.S., Parry M.A.J., Halford N.G. Reducing acrylamide precursors in raw materials derived from wheat and potato. J.Agric. Food Chem. 2008, 56:6167-6172.
65. Nikiforova V.J., Bielecka M., Gakiere B., Krueger S., Rinder J., Kempa S., Morcuende R., Scheible W.R., Hesse H., Hoefgen R. Effect of sulfur availability on the integrity of amino acid biosynthesis in plants. Amino Acids 2006, 30:173-183.
66. Nursten H.E. The Maillard Reaction 2005, Royal Society of Chemistry, Cambridge.
67. Nyström L., Lampi A.M., Andersson A.A.M., Kamal-Eldin A., Gebruers K., Courtin C.M., Delcour J.A., Li L., Ward J.L., Fras A., Boros D., Rakszegi M., Bedo Z., Shewry P.R., Piironen V. Phytochemicals and dietary fiber components in rye varieties in the HEALTHGRAIN diversity screen. J.Agric. Food Chem. 2008, 56:9758-9766.
68. Olsen A., Christensen J., Outzen M., Olesen P.T., Frandsen H., Overvad K., Halkjær J. Pre-diagnostic acrylamide exposure and survival after breast cancer among postmenopausal Danish women. Toxicology 2012, 296:67-72.
69. Pedersen M., von Stedingk H., Botsivali M., Agramunt S., Alexander J., Brunborg G., Chatzi L., Fleming S., Fthenou E., Granum B., Gutzkow K.B., Hardie L.J., Knudsen L.E., Kyrtopoulos S.A., Mendez M.A., Merlo D.F., Nielsen J.K., Rydberg P., Segerbäck D., Sunyer J., Wright J., Törnqvist M., Kleinjans J.C., Kogevinas M. Birth weight, head circumference, and prenatal exposure to acrylamide from maternal diet: the European prospective mother-child study (NewGeneris). Environ. Health Persp. 2012, 120:1739-1745. the NewGeneris Consortium.
70. Perez Locas C., Yaylayan V.A. Origin and mechanistic pathways of formation of the parent furan - a food toxicant. J.Agric. Food Chem. 2004, 52:6830-6836.
71. Possingham J.V. The effect of mineral nutrition on the content of free amino acids and amides in tomato plants. I. A comparison of the effects of deficiencies of copper, zinc, manganese, iron and molybdenum. Aust. J. Biol. Sci. 1956, 9:539-551.
72. Postles J., Powers S., Elmore J.S., Mottram D.S., Halford N.G. Effects of variety and nutrient availability on the acrylamide forming potential of rye grain. J.Cereal Sci. 2013, 57:463-470.
73. Rabe E., Lovatt C.J. Increased arginine biosynthesis during phosphorus deficiency. Plant Physiol. 1986, 81:774-779.
74. Ramírez-Jiménez A., García-Villanova B., Guerra-Hernández E. Hydroxymethylfurfural and methylfurfural content of selected bakery products. Food Res. Int. 2000, 33:833-838.
75. Rognes S.E. Anion regulation of lupine asparagine synthetase: chloride activation of the glutamine-utilizing reactions. Phytochemistry 1980, 19:2287-2293.
76. Román-Leshkov Y., Chheda J.N., Dumesic J.A. Phase modifiers promote efficient production of hydroxymethylfurfural from Fructose. Science 2006, 312:1933-1937.
77. Rommens C.M., Yan H., Swords K., Richael C., Ye J. Low-acrylamide French fries and potato chips. Plant Biotech. J. 2008, 6:843-853.
78. Rufty T.W., MacKown C.T., Israel D.W. Phosphorus stress effects on the assimilation of nitrate. Plant Physiol. 1990, 94:328-333.
79. Shewry P.R., Franklin J., Parmar S., Smith S.J., Miflin B.J. The effects of sulphur starvation on the amino acid and protein compositions of barley grain. J.Cereal Sci. 1983, 1:21-31.
80. Shewry P.R., Tatham A.S., Halford N.G. Nutritional control of storage protein synthesis in developing grain of wheat and barley. Plant Growth Regul. 2001, 34:105-111.
81. Shewry P.R., Zhao F.-J., Gowa G.B., Hawkins N.D., Ward J.L., Beale M.H., Halford N.G., Parry M.A.J., Abécassis J. Sulphur nutrition differentially affects the distribution of asparagine in wheat grain. J.Cereal Sci. 2009, 50:407-409.
82. Sieciechowicz K.A., Joy K.W., Ireland R.J. The metabolism of asparagine in plants. Phytochemistry 1988, 27:663-671.
83. Snapp S.S., Vance C.P. Asparagine biosynthesis in alfalfa (Medicago sativa L.) root nodules. Plant Physiol. 1986, 82:390-395.
84. Stadler R.H., Blank I., Varga N., Robert F., Hau J., Guy P.A., Robert M.C., Riediker S. Acrylamide from Maillard reaction products. Nature 2002, 419:449-450.
85. Stadler R.H., Verzegnassi L., Varga N., Grogorov M., Studer A., Riediker S., Schilter B. Formation of vinylogous compounds in model Maillard reaction systems. Chem. Res. Toxicol. 2003, 16:1242-1250.
86. Stewart G.R., Larher F. Accumulation of amino acids and related compounds in relation to environmental stress. The Biochemistry of Plants 1980, vol. 5:609-635. Academic Press, London.
87. Taeymans D., Wood J., Ashby P., Blank I., Studer A., Stadler R.H., Gonde P., Van Eijck P., Lalljie S., Lingnert H., Lindblom M., Matissek R., Muller D., Tallmadge D., O'Brien J., Thompson S., Silvani D., Whitmore T. Areview of acrylamide: an industry perspective on research, analysis, formation and control. Crit. Rev. Food Sci. Nut. 2004, 44:323-347.
88. Tareke E., Rydberg P., Karlsson P., Eriksson S., Tornqvist M. Analysis of acrylamide, a carcinogen formed in heated foodstuffs. J.Agric. Food Chem. 2002, 50:4998-5006.
89. Wang H., Liu D., Sun J., Zhang A. Asparagine synthetase gene TaASN1 from wheat is up-regulated by salt stress, osmotic stress and ABA. J.Plant Physiol. 2005, 162:81-89.
90. Wang Y., Jacome-Sosa M.M., Vine D.F., Proctor S.D. Beneficial effects of vaccenic acid on postprandial lipid metabolism and dyslipidemia: Impact of natural trans-fats to improve CVD risk. Lipid Technol. 2010, 22:103-106.
91. Ward J.L., Poutanen K., Gebruers K., Piironen V., Lampi A.-M., Nystrom L., Andersson A.A.M., Aman P., Boros D., Rakszegi M., Bedo Z., Shewry P.R. The HEALTHGRAIN cereal diversity screen: concept, results, and prospects. J.Agric. Food Chem. 2008, 56:9699-9709.
92. Winkler U., Schön W.J. Amino acid composition of the kernel proteins in barley resulting from nitrogen fertilization at different stages of development. J.Agron. Crop Sci. 1980, 149:503-512.
93. Yannai S. Toxic factors induced by processing. Toxic Constituents of Plant Foodstuffs 1980, 371-427. Academic Press, London. second ed. I.E. Liener (Ed.).
94. Zhang Y., Dickinson J.R., Paul M.J., Halford N.G. Molecular cloning of an arabidopsis homologue of GCN2, a protein kinase involved in co-ordinated response to amino acid starvation. Planta 2003, 217:668-675.
95. Zhang Y., Wang Y., Kanyuka K., Parry M.A.J., Powers S.J., Halford N.G. GCN2-dependent phosphorylation of eukaryotic translation initiation factor-2α in Arabidopsis. J.Exp. Bot. 2008, 59:3131-3141.
96. Zhao F.J., Hawkesford M.J., McGrath S.P. Sulphur assimilation and effects on yield and quality of wheat. J.Cereal Sci. 1999, 30:1-17.
97. Zhao F.J., McGrath S.P., Blake-Kalff M.M.A., Link A., Tucker M.R. Crop Responses to Sulphur Fertilisation in Europe. International Fertiliser Society Proceeding No 504 2002, The International Fertiliser Society, York.
98. Zyzak D.V., Sanders R.A., Stojanovic M., Tallmadge D.H., Eberhart B.L., Ewald D.K., Gruber D.C., Morsch T.R., Strothers M.A., Rizzi G.P., Villagran M.D. Acrylamide formation mechanism in heated foods. J.Agric. Food Chem. 2003, 51:4782-4787.