Skip to main content
SpringerLink
Log in

Comparison of volatile Maillard reaction products from tagatose and other reducing sugars with amino acids

  • Research Article
  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

Abstract

In this study, in order to investigate the effects of tagatose on the Maillard reaction, volatile Maillard reaction products (V-MRPs) produced from aqueous model systems containing various reducing sugars (glucose, galactose, fructose, and tagatose) and amino acids (glycine, valine, leucine, asparagine, and cysteine) were analyzed and then compared. Furans, furan derivatives, pyrazines, and some sulfur-containing heterocyclic compounds, such as thiazoles, thiophenes, and thiols, were mainly identified. The amounts of furans and furan derivatives were higher in the model systems of ketoses (fructose or tagatose) with amino acids than those of aldoses (glucose or galactose) with amino acids. In particular, 2-acetylfuran was detected 2-20 times more in the V-MRPs of tagatose as compared to those produced from the other reducing sugars. Also, 2-acetylpyrrole, one of nitrogen-containing heterocyclic compounds, was more abundant from the thermal reactions of tagatose-glycine and tagatose-valine compared to those of other reducing sugars-amino acids. More 2-acetylthiazole and thiophenes were found in tagatose-cysteine model system than in those of glucose with cysteine.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Hirst EL, Hough L, Jones JKN. Composition of the gum of Sterculia Setigera: Occurrence of d-tagatose in nature. Nature 163: 177–177 (1949)

    Article  CAS  Google Scholar 

  2. Lindberg B. Studies on the chemistry of Lichens. Investigation of a Dermatocarpon and some Roccella species. Acta Chem. Scand. 9: 9171–919 (1955)

    Google Scholar 

  3. Roh HJ, Kim P, Park YC, Choi JH. Bioconversion of d-galactose into d-tagatose by expression of l-arabinose isomerase. Biotechnol. Appl. Bioc. 31: 1–4 (2000)

    Article  CAS  Google Scholar 

  4. Bertelsen H, Jensen BB, Buemann B. d-Tagatose-a novel low calorie bulk sweetener with prebiotic properties. World Rev. Nutr. Diet 85: 98–109 (1999)

    Article  CAS  Google Scholar 

  5. Levin GV, Zehner LR, Saunders JP, Beadle JR. Sugar substitutes: Their energy values, bulk characteristics, and potential health benefits. Am. J. Clin. Nutr. 62: 1161S–1168S (1995)

    CAS  Google Scholar 

  6. WHO. Evaluation of certain food additives and contaminants (55th Report of the Joint FAO/WHO Expert Committee on Food Additives). WHO Technical Report Series 901: 13–15 (2001)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  8. Mlotkiewicz JA. The role of the Maillard reaction in the food industry. pp. 19–27. In: The Maillard Reaction in Foods and Medicine. O’Brien J, Nursten HE, Crabbe MJC, Ames JM (eds). The Royal Society of Chemistry, Cambridge, UK (1988)

    Google Scholar 

  9. Nagodawithana TW. Maillard and other flavor producing reactions. pp. 103-163. In: Savory Flavors. Nagodawithana TW (ed). Esteekay Associates, Inc., Milwaukee, WI, USA (1995)

    Google Scholar 

  10. Lingnert H. The Maillard reaction in food processing, human nutrition, and physiology. pp. 171–185. In: Development of the Maillard Reaction During Food Processing. Finot PA, Aeschbacher HU, Hurrell RF, Liardon R (eds). Birkhauser Verlag, Basel, Switzerland (1990)

    Google Scholar 

  11. Wijewickreme AN, Kitts DD. Influence of reaction conditions on the oxidative behavior of model Maillard reaction products. J. Agr. Food Chem. 45: 4571–4576 (1997)

    Article  CAS  Google Scholar 

  12. Reyes FGR, Poocharoen B, Wrolstad R. Maillard browning reaction of sugar-glycine model systems: Changes in sugar concentration, color, and appearance. J. Food Sci. 47: 31376–31377 (1982)

    Google Scholar 

  13. Chen JH, Ho CT. Volatile compounds generated in serine-monosaccharide model systems. J. Agr. Food Chem. 46: 1518–1522 (1998)

    Article  CAS  Google Scholar 

  14. Chen JH, Ho CT. Comparison of volatile generation in serine/threonine/glutamine-ribose/glucose/fructose model systems. J. Agr. Food Chem. 47: 643–647 (1999).

    Article  CAS  Google Scholar 

  15. Cerny C, Davidek T. Formation of aroma compounds from ribose and cysteine during the Maillard reaction. J. Agr. Food Chem. 51: 2714–2721 (2003)

    Article  CAS  Google Scholar 

  16. Antal MJ, Mok WSL, Richards GN. Mechanism of formation of 5-hydroxymethyl-2-furaldehyde from d-fructose and sucrose. Carbohyd. Res. 199: 91–109 (1990)

    Article  CAS  Google Scholar 

  17. Lee HS, Nagy S. Relative reactivities of sugars in the formation of 5-hydroxymethyl furaldehyde in sugar-catalyst model system. J. Food Process. Preserv. 14: 171–178 (1990)

    Article  CAS  Google Scholar 

  18. Wang Y, Ho CT. Comparison of 2-acetylfuran formation between ribose and glucose in the Maillard reaction. J. Agr. Food Chem. 56: 11997–12001 (2008)

    Article  CAS  Google Scholar 

  19. Wang Y, Juliani B, Simon JE, Ho CT. Amino acid-dependent formation pathways of 2-acetylfuran and 2,5-dimethyl-4-hydroxy-3(2H)-furanone in the Maillard reaction. Food Chem. 115: 233–237 (2009)

    Article  CAS  Google Scholar 

  20. Reineccius G. Changes in food flavor due to processing. pp. 103–137. In: Flavor Chemistry and Technology. Reineccius G (ed). CRC Press, Boca Raton, FL, USA (2006)

    Google Scholar 

  21. Yaylayan AV. Classification of the Maillard reaction: A conceptual approach. Trends Food Sci. Tech. 8: 13–18 (1997)

    Article  CAS  Google Scholar 

  22. Robert DD, Acree TE. Gas chromatography-olfactometry of glucose-proline Maillard reaction products. ACS Symp. Ser. 543: 71–79 (1994)

    Article  Google Scholar 

  23. Hofmann T, Schieberle P. Evaluation of the key odorants in a thermally treated solution of ribose and cysteine by aroma extract dilution technique. J. Agr. Food Chem. 43: 2187–2194 (1995)

    Article  CAS  Google Scholar 

  24. Hofmann T, Schieberle P. Identification of potent aroma compounds in thermally treated mixtures of glucose/cysteine and rhamnose/cysteine using aroma extract dilution techniques. J. Agr. Food Chem. 45: 898–906 (1997)

    Article  CAS  Google Scholar 

  25. Brands CMJ, van Boekel MAJS. Kinetic modeling of reactions in heated monosaccharide-casein systems. J. Agr. Food Chem. 50: 6725–6739 (2002)

    Article  CAS  Google Scholar 

  26. Ryu SY, Roh HJ, Noh BS, Kim SY, Oh DK, Lee WJ, Yoon JR, Kim SS. Effects of temperature and pH on the non-enzymatic browning reaction of tagatose-glycine model system. Food Sci. Biotechnol. 12: 675–679 (2003)

    CAS  Google Scholar 

  27. van den Dool H, Kratz PD. A generalisation of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatogr. 11: 463–471 (1963)

    Article  Google Scholar 

  28. Kondjoyan N, Berdague JL. Compilation of relative retention indices for the analysis of aromatic compounds: Laboratoire Faveur, Station de Recherches sur la Viande. Clermont-Ferrand, France (1996)

    Google Scholar 

  29. Adams RP. Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy. Allured Publishing Co., Carol Stream, IL, USA (2001)

    Google Scholar 

  30. Acree TE, Arn H. Flavornet. http://www.nysaes.cornell.edu/flavornet. Cornell University, Geneva, USA. Accessed Mar. 10, 2009.

  31. Nursten HE. Volatiles produced by the Maillard reaction. pp. 475–491. In: Frontiers of Flavour Science. Schieberle P, Engel KH (eds). Deutsche Forschung, Lebensmittel, Garching, Germany (2000)

    Google Scholar 

  32. Buttery RG, Stern DJ, Ling LC. Studies on flavor volatiles of some sweet corn products. J. Agr. Food Chem. 42: 791–795 (1994)

    Article  CAS  Google Scholar 

  33. Yamaguchi K, Shibamoto T. Volatile constituents of Castanopsis flower. J. Agr. Food Chem. 27: 847–850 (1979)

    Article  CAS  Google Scholar 

  34. Yuan JP, Chen F. Separation and identification of furanic compounds in fruit juices and drinks by high-performance liquid chromatography photodiode array detection. J. Agr. Food Chem. 46: 1286–1291 (1998)

    Article  CAS  Google Scholar 

  35. Jennifer MA, Richard AB. Effect of nitrogen source on pyrazine formation. J. Agr. Food Chem. 36: 123–129 (1988)

    Article  Google Scholar 

  36. Ohloff G, Flament I. The role of heteroatomic substances in the aroma compounds of foodstuffs. Fortschr. Chem. Org. Naturst. 36: 231–236 (1978)

    Google Scholar 

  37. Hodge JE, Mills FD, Fisher BE. Compounds of browned flavor derived from sugar-amine reactions. Cereal Sci. Today 17: 34–38 (1972)

    Google Scholar 

  38. Tressl R, Halak B, Marn N. Formation of flavor compounds from Lproline. pp. 139–143. In: Topics in Flavor Research. Berger RG, Nitz S, Schreier P (eds). H. Eichorn, Marzling-Hangenham, Germany (1985)

    Google Scholar 

  39. Shibamoto T. Heterocyclic compounds in browning and browning/nitrite model systems: Occurrence, formation mechanisms, flavor characteristics, and mutagenic activity. pp. 229–249. In: Instrumental Analysis of Foods. Charalambous G, Inglett G (eds). Acadam Press, New York, NY, USA (1985)

    Google Scholar 

  40. Sakaguchi M, Shibamoto T. Formation of sulfur-containing compounds from the reaction of d-glucose and hydrogen sulfide. J. Agr. Food Chem. 26: 1260–1264 (1978)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Food Science and Technology, Ewha Womans University, Seoul, 120-750, Korea

    In Hee Cho, Sarah Lee, Hae-Roung Jun & Young-Suk Kim

  2. R&D Center, Orion Confectionery, Seoul, 140-715, Korea

    Hoe-Jin Roh

Authors
  1. In Hee Cho
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sarah Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hae-Roung Jun
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hoe-Jin Roh
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Young-Suk Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Young-Suk Kim.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cho, I.H., Lee, S., Jun, HR. et al. Comparison of volatile Maillard reaction products from tagatose and other reducing sugars with amino acids. Food Sci Biotechnol 19, 431–438 (2010). https://doi.org/10.1007/s10068-010-0061-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-010-0061-7

Keywords

Search

Navigation