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The Effect of pH on the Formation of Furfural Compounds in the Glucose and Fructose with Amino Acid Enantiomers in Maillard Reaction

  • Kim, Ji-Sang (Department of Food and Nutrition, Kyung Hee University) ;
  • Lee, Young-Soon (Department of Food and Nutrition, Kyung Hee University)
  • Published : 2008.03.31

Abstract

This study was conducted to investigate the effect of pH on the formation of furfural compounds from glucose and fructose reacting with amino acid enantiomers in the Maillard reaction. Hydroxymethylfurfural (HMF) content was highest at pH 4.0, and decreased with increasing pH. HMF was significantly higher in glucose-based systems than fructose-based systems. Furfuryl alcohol (FFA) and 5-methyl-2-furaldehyde (MF) were not increased with increasing pH, and only small amounts were formed. In addition, 2-furaldehyde (F) was found to increase in the systems, as pH increased. However, the content was small and variable. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (DMHF) was only found in Glc/D-Asn, Glc/L-Lys and Fru/D-Lys system, but the content was not increased with increasing pH. 2-acetylfuran (AF) was higher in Glc (or Fru)/L-Lys and Glc (or Fru)/D-Lys systems at pH 7.0. However, at pH 4.0, the content of AF was higher in the Glc (or Fru)/Gly and Glc (or Fru)/L-Asn systems. Therefore, this study aimed to observe the effect of pH, sugars and amino acid enantiomers on the production of furfural and related compounds by the Maillard reaction. A clear tendency was observed for some classes of compounds to be more easily formed at higher or lower pH. HMF was more readily formed at lower pH, while FFA, F, DMHF and MF were inhibited by acidic conditions. Particularly, compounds like FFA, F and MF were not affected by pH changes. In addition, DMHF and MF were only formed in L-Lys and D-Lys system.

References

  1. Maillard LC. 1913. Formation de matieres humiques par action de polypeptides sur sucres. C R Acad Sci 156: 148-149
  2. Wijewickreme AN, Kitts DD, Durance TD. 1997. Reaction conditions influence the elementary composition and metal chelating affinity of nondialyzable model Maillard reaction products. J Agric Food Chem 45: 4577-4583 https://doi.org/10.1021/jf970041n
  3. Friedman M. 1999. Chemistry, nutrition, and microbiology of D-amino acids. J Agric Food Chem 47: 3457-3479 https://doi.org/10.1021/jf990080u
  4. Bruckner H, Justus J, Kirschbaum J. 2001. Saccharide induced racemization of amino acids in the course of the Maillard reaction. Amino Acids 21: 429-433 https://doi.org/10.1007/s007260170007
  5. Ledl F, Schleicher E. 1990. New aspects of the Maillard reaction in foods and in the human body. Angew Chem Int Ed Engl 29: 565-594 https://doi.org/10.1002/anie.199005653
  6. Patzold R, Nieto-Rodriguez A, Bruckner H. 2003. Chiral gas chromatographic analysis of amino acids in fortified wines. Chromatographia Suppl 57: S207-S212 https://doi.org/10.1007/BF02492104
  7. Patzold R, Bruckner H. 2005. Mass spectrometric detection and formation of D-amino acids in processed plant saps, syrups, and fruit juice concentrates. J Agric Food Chem 53: 9722-9729 https://doi.org/10.1021/jf051433u
  8. Patzold R, Bruckner H. 2006a. Gas chromatographic detection of D-amino acids in natural and thermally treated bee honeys and studies on the mechanism of their formation as result of the Maillard reaction. Eur Food Res Tech 223: 347-354 https://doi.org/10.1007/s00217-005-0211-y
  9. Patzold R, Bruckner H. 2006b. Gas chromatographic determination and mechanism of formation of D-amino acids occurring in fermented and roasted cocoa beans, cocoa powder, chocolate and other cocoa products. Amino Acids 31: 63-72 https://doi.org/10.1007/s00726-006-0330-1
  10. Bada JL. 1972. Kinetics of racemization of amino acids as a function of pH. J Am Chem Soc 94: 1371-1373 https://doi.org/10.1021/ja00759a064
  11. Yeo H, Shibamoto T. 1991. Effects of moisture content on the Maillard browning model system upon microwave irradiation. J Agric Food Chem 39: 1860-1862 https://doi.org/10.1021/jf00010a035
  12. Espinosa-Mansilla A, Salinas F, Berzas-Nevado JJ. 1992. Differential determination of furfural and hydroxymethylfurfural by derivative spectrophotometry. J AOAC Int 75: 678-684
  13. Morales FJ, Romero C, Jimenez-Perez S. 1992. An enhanced liquid chromatography method for 5-hydroxymethylfurfural determination in UHT milk. Chromatographia 33: 45-48 https://doi.org/10.1007/BF02276850
  14. Blanco-Gomis D, Gutierrez-Alvarez MD, Sopena-Naredo L, Mangas-Alonso JJ. 1991. High-performance liquid chromatographic determination of furfural and hydroxymethylfurfural in apple juices and concentrates. Chromatographia 32: 45-48 https://doi.org/10.1007/BF02262465
  15. Sanz C, Perez AG, Richardson DG. 1994. Simultaneous HPLC determination of 2,5-dimethyl-4-hydroxy-3(2H)-furanone and related flavor compounds in strawberries. J Food Sci 59: 139-141 https://doi.org/10.1111/j.1365-2621.1994.tb06918.x
  16. Eiserich JP, Macku C, Shibamoto T. 1992. Volatile antioxidants formed from an L-cysteine/D-glucose Maillard model system. J Agric Food Chem 40: 1982-1988 https://doi.org/10.1021/jf00022a050
  17. Blank I, Fay LB. 1996. Formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone through Maillard reaction based on pentose sugars. J Agric Food Chem 44: 531-536 https://doi.org/10.1021/jf950439o
  18. Lee HS, Nagy S. 1988. Relationship of sugar degradation to detrimental changes in citrus juice quality. Food Technol 11: 91-97
  19. Mijares RM, Park GL, Nelson DB, Mciver RC. 1986. HPLC analysis of HMF in orange juice. J Food Sci 51: 843-844 https://doi.org/10.1111/j.1365-2621.1986.tb13949.x
  20. Tu D, Xue S, Meng C, Espinosa-Mansilla A, De la Pena AM, Lopez FS. 1992. Simultaneous determination of 2-furfuraldehyde and 5-(hydroxymethyl)-2-furfuraldehyde by derivative spectrophotometry. J Agric Food Chem 40: 1022-1025 https://doi.org/10.1021/jf00018a021
  21. Dinsmore HL, Nagy S. 1974. Improved calorimetric determination for furfural in citrus juices. J Assoc Off Anal Chem 57: 332
  22. Marcy JE, Rouseff RL. 1984. High-performance liquid The Formation of Furfural Compounds in Maillard Reaction 59 chromatographic determination of furfural in orange juice. J Agric Food Chem 32: 979-981 https://doi.org/10.1021/jf00125a005
  23. Guerra-Hernandez E, Garcia-Vilanova B, Montilla-Gomez J. 1992. Determination of hydroxymethylfurfural in baby cereals by high performance liquid chromatography. J Liq Chromatogr 15: 2551-2559 https://doi.org/10.1080/10826079208017201
  24. Krammer GE, Takeoka GR, Buttery RG. 1994. Isolation and identification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone glucoside from tomatoes. J Agric Food Chem 42: 1595-1597 https://doi.org/10.1021/jf00044a001
  25. Lo Coco F, Ceccon L, Valentini C, Novelli V. 1992. High-performance liquid chromatographic determination of 2-furaldehyde in spirits. J Chromatogr 590: 235-240 https://doi.org/10.1016/0021-9673(92)85386-8
  26. Albala-Hurtado S, Veciana-Nogues MT, Marine-Font A, Vidal-Carou MC. 1998. Changes in furfural compounds during storage of infant milks. J Agric Food Chem 46: 2998-3003 https://doi.org/10.1021/jf980079f
  27. Lo-Coco F, Valentini C, Novelli V, Ceccon L. 1994. High performance liquid chromatographic determination of 2-furaldehyde and 5-hydroxymethyl-2-furaldehyde in processed citrus juices. J Liq Chromatog 17: 603-617 https://doi.org/10.1080/10826079408013163
  28. Naim M, Wainish S, Zehavi U, Peleg H, Rouseff RL, Nagy S. 1993. Inhibition by thiol compounds of off-flavor formation in stored orange juice. 1. Effect of L-cysteine and N-acetyl-cysteine on 2,5-dimethyl-4-hydroxy-3(2H)-furanone formation. J Agric Food Chem 41: 1355-1358 https://doi.org/10.1021/jf00033a002
  29. Berg HE, van Boekel MAJS. 1994. Degradation of lactose during heating of milk. 1. Reaction pathways. Neth Milk Dairy J 48: 157-175
  30. Morales FJ, Romero C, Jimenez-Perez S. 1997. Chromatographic determination of bound hydroxymethylfurfural as an index of milk protein glycosylation. J Agric Food Chem 45: 1570-1573 https://doi.org/10.1021/jf960930v
  31. Kroh LW. 1994. Caramelisation in food and beverages. Food Chem 51: 373-379 https://doi.org/10.1016/0308-8146(94)90188-0
  32. Cuzzoni MT, Stoppini G, Gazzani G, Mazza P. 1988. Influence of water activity and reaction temperature of ribose-lysine and glucoselysine Maillard systems on mutagenicity, absorbance and content of furfurals. Food Chem Toxicol 26: 815-822 https://doi.org/10.1016/0278-6915(88)90020-8
  33. Janzowski C, Glaab V, Samimi E, Schlatter J, Eisenbrand G. 2000. 5-hydroxymethylfurfural: assessment of mutagenicity, DNA damaging potential and reactivity towards cellular glutathione. Food Chem Toxicol 38: 801-809 https://doi.org/10.1016/S0278-6915(00)00070-3
  34. Lee YC, Shlyankevich M, Jeong HK, Douglas JS, Surh Y. 1995. Bioactivation of 5-hydroxymethyl-2-furaldehyde to an electrophilic and mutagenic allylic sulfuric-acid ester. Biochem Biophys Res Comm 209: 996-1002 https://doi.org/10.1006/bbrc.1995.1596
  35. Antonelli A, Chinnici F, Masino F. 2004. Heat-induced chemical Antonelli, A during the production of traditional balsamic vinegar: a preliminary approach. Food Chem 88: 63-68 https://doi.org/10.1016/j.foodchem.2004.01.023
  36. Hodge JE. 1953. Chemistry of browning reactions in model systems. J Agric Food Chem 1: 928-943 https://doi.org/10.1021/jf60015a004
  37. 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: 3164-3172 https://doi.org/10.1021/jf981289v
  38. Ferrer E, Alegria A, Farre R, Abellan P, Romero F. 2002. High-performance liquid chromatographic determination of furfural compounds in infant formulas-Changes during heat treatment and storage. J Chromatogr A 947: 85-95 https://doi.org/10.1016/S0021-9673(01)01593-X
  39. Mottram DS, Leseigneur A. 1990. The effect of pH on the formation of aroma volatiles in meat-like model systems. In Flavour Science and Technology. Bessiere Y, Thomas AF, eds. John Wiley & Sons, Chichester, UK. p 121-124

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