Czech J. Food Sci., 2010, 28(3):192-201 | DOI: 10.17221/189/2008-CJFS

Effect of pressure on the Maillard reaction between ribose and cysteine in supercritical carbon dioxide

Honggao Xu, Wenhao He, Xuan Liu, Yanxiang Gao
College of Food Science and Nutritional Engineering, China Agricultural University, Beijing, P. R. China

An aqueous ribose-cysteine model system, heated at 140°C under supercritical carbon dioxide (SC-CO2) and supercritical nitrogen (SC-N2), was investigated with emphasis on the formation of volatile compounds. In general, SC-CO2 facilitated the overall intermediates accumulation while suppressing the advanced stage of browning. 3-Methyl-1, 2-dithian-4-one increased with increasing SC-CO2 pressure, and was always more concentrated than in the case of SC-N2-treatment. The formation of thiols, disulfides, and formyl substituted thiophenes was also promoted in SC-CO2-treated reaction products, while the effect of high pressure on the individual components followed different patterns. The reversible pH decrease and reinforced acid-base catalysis of 2, 3-enolisation by SC-CO2 could attribute to the decreased browning and higher amounts of most intense meaty aromatic compounds.

Keywords: supercritical carbon dioxide (SC-CO2); pressure; Maillard reaction; ribose; cysteine; volatiles

Published: June 30, 2010  Show citation

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Xu H, He W, Liu X, Gao Y. Effect of pressure on the Maillard reaction between ribose and cysteine in supercritical carbon dioxide. Czech J. Food Sci. 2010;28(3):192-201. doi: 10.17221/189/2008-CJFS.
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References

  1. Ames J.M., Guy R.C.E., Kipping G.J. (2001): Effect of pH and temperature on the formation of volatile compounds in cysteine/reducing sugar/starch mixtures during extrusion cooking. Journal of Agricultural and Food Chemistry, 49: 1885-1894. Go to original source... Go to PubMed...
  2. Beckman E.J. (2004): Supercritical and near-critical CO2 in green chemical synthesis and processing. The Journal of Supercritical Fluids, 28: 121-191. Go to original source...
  3. Bristow M., Isaacs N.S. (1999): The effect of high pressure on the formation of volatile products in a model Maillard reaction. Journal of the Chemical Society, Perkin Transactions, 2: 2213-2218. Go to original source...
  4. Carabasa-Giribet M., Ibarz-Ribas A. (2000): Kinetics of colour development in aqueous glucose systems at high temperatures. Journal of Food Engineering, 44: 181-189. Go to original source...
  5. Casal E., Ramírez P., Ibañez E., Corzo N., Olano A. (2006): Effect of supercritical carbon dioxide treatment on the Maillard reaction in model food systems. Food Chemistry, 97: 272-276. Go to original source...
  6. Cerny C., Briffod M. (2007): Effect of pH on the Maillard reaction of [13C5] xylose, cysteine, and thiamin. Journal of Agricultural and Food Chemistry, 55: 1552-1556. Go to original source... Go to PubMed...
  7. Chen Y., Ho C.T. (2002): Effect of carnosine on volatile generation from Maillard reaction of ribose and cysteine. Journal of Agricultural and Food Chemistry, 50: 2372-2376. Go to original source... Go to PubMed...
  8. Damar S., Balaban M.O. (2006): Review of dense phase CO2 technology: microbial and enzyme inactivation, and effects on food quality. Journal of Food Science, 71: R1-R11. Go to original source...
  9. Farmer L.J., Mottram D.S., Whitfield F.B. (1989): Volatile compounds produced in Maillard reactions involving cysteine, ribose and phospholipid. Journal of the Science of Food and Agriculture, 49: 347-368. Go to original source...
  10. Gevaudan S., Lagaude A., Tarodo De La Fuente B., Cuq J.L. (1996): Effect of treatment by gaseous carbon dioxide on the colloidal phase of skim milk. Journal of Dairy Science, 79: 1713-1721. Go to original source...
  11. Güntert M., Brüning J., Emberger R., Köpsel M., Kuhn W., Thielmann T., Werkhoff P. (1990): Identification and formation of some selected sulfur-containing flavor compounds in various meat model systems. Journal of Agricultural and Food Chemistry, 38: 2027-2041. Go to original source...
  12. Hartman G.J., Scheide J.D., Ho C.T. (1984): Effect of water activity on the major volatiles produced in a model system approximating cooked meat. Journal of Food Science, 49: 607-613. Go to original source...
  13. Herrero M., Cifuentes A., Ibañez E. (2006): Suband supercritical fluid extraction of functional ingredients from different natural sources: plants, food-by-products, algae and microalgae a review. Food Chemistry, 98: 136-148. Go to original source...
  14. Hill V.M., Ledward D.A., Ames J.M. (1996): Influence of high hydrostatic pressure and pH on the rate of Maillard browning in a glucose-lysine system. Journal of Agricultural and Food Chemistry, 44: 594-598. Go to original source...
  15. Hofmann T., Schieberle P. (1998): Quantitative model studies on the effectiveness of different precursor systems in the formation of the intense food odorants 2-furfurylthiol and 2-methyl-3-furanthiol. Journal of Agricultural and Food Chemistry, 46: 235-241. Go to original source... Go to PubMed...
  16. Komthong P., Katoh T., Igura N., Shimoda M., Hayakawa I. (2003): Effect of high hydrostatic pressure combined with pH and temperature on glucose/fructose-leucine/lysine/glutamate browning reactions. Journal of the Faculty of Agriculture, Kyushu University, 48: 135-142. Go to original source...
  17. Maeda S., Kunitou K., Hihara T., Mishima K. (2004): One-bath dyeing of polyester/cotton blends with reactive disperse dyes in supercritical carbon dioxide. Textile Research Journal, 74: 989-994. Go to original source...
  18. Meynier A., Mottram D.S. (1995): The effect of pH on the formation of volatile compounds in meat-related model systems. Food Chemistry, 52: 361-366. Go to original source...
  19. Moreno F.J., Molina E., Olano A., López-Fandiño R. (2003): High-pressure effects on Maillard reaction between glucose and lysine. Journal of Agricultral and Food Chemistry, 51: 394-400. Go to original source... Go to PubMed...
  20. Mottram D.S., Nobrega I.C.C. (2002): Formation of sulfur aroma compounds in reaction mixtures containing cysteine and three different forms of ribose. Journal of Agricultural and Food Chemistry, 50: 4080-4086. Go to original source... Go to PubMed...
  21. Mottram D.S., Whitfield F.B. (1995): Maillard-lipid interactions in nonaqueous systems: volatiles from the reaction of cysteine and ribose with phosphatidylcholine. Journal of Agricultural and Food Chemistry, 43: 1302-1306. Go to original source...
  22. Mottram D.S., Madruga M.S., Whitfield F.B. (1995): Some novel meatlike aroma compounds from the reactions of alkanediones with hydrogen sulfide and furanthiols. Journal of Agricultural and Food Chemistry, 43: 189-193. Go to original source...
  23. Oakes R.S., Clifford A.A., Rayner C.M. (2001): The use of supercritical fluids in synthetic organic chemistry. Journal of the Chemical Society, Perkin Transactions, 1: 917-941. Go to original source...
  24. Parker J.K., Hassell G.M.E., Mottram D.S., Guy R.C.E. (2000): Sensory and instrumental analyses of volatiles generated during the extrusion cooking of oat flours. Journal of Agricultural and Food Chemistry, 48: 3497-3506. Go to original source... Go to PubMed...
  25. Sihvonen M., Järvenpää E., Hietaniemi V., Huopalahti R. (1999): Advances in supercritical carbon dioxide technologies. Trends of Food Science and Technology, 10: 217-222. Go to original source...
  26. Van Den Ouweland G.A.M., Peer H.G. (1975): Components contributing to beef flavor. Volatile compounds produced by the reaction of 4-hydroxy5-methyl-3(2H)-furanone and its thio analog with hydrogen sulfide. Journal of Agricultural and Food Chemistry, 23: 501-505. Go to original source...
  27. Vemavarapu C., Mollan M.J., Lodaya M., Needham T.E. (2005): Design and process aspects of laboratory scale SCF particle formation systems. International Journal of Pharmaceutics, 292: 1-16. Go to original source... Go to PubMed...
  28. Whitfield F.B., Mottram D.S. (1999): Investigation of the reaction between 4-hydroxy-5-methyl-3(2H)furanone and cysteine or hydrogen sulfide at pH 4.5. Journal of Agricultural and Food Chemistry, 47: 1626-1634. Go to original source... Go to PubMed...
  29. Xu H., Gao Y., Liu X., Zhao J. (2008a): Effects of supercritical carbon dioxide on volatile formation from Maillard reaction between ribose and cysteine. Journal of the Science of Food and Agriculture, 88: 328-335. Go to original source...
  30. Xu H., Liu X., Zhao J., Gao Y. (2008b): Effects of ribose to cysteine ratios on the formation of volatile compounds from the Maillard reaction in supercritical carbon dioxide. Food Research International, 41: 730-737. Go to original source...
  31. Yalpani M. (1993): Supercritical fluids: puissant media for the modification of polymers and biopolymers. Polymer, 34: 1102-1105. Go to original source...
  32. Zhang Y., Chien M., Ho C.T. (1988): Comparison of the volatile compounds obtained from thermal degradation of cysteine and glutathione in water. Journal of Agricultural and Food Chemistry, 36: 992-996. Go to original source...

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