Infuence of various factors on formation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(z7)-pyran-4-one (ddmp) in a solid-state model system of maillard reaction

European Food Research and Technology

Volumn 239, Issue 1, 2014, Pages 31-40

  Zhou, Zhilei ^a   Xu, Zhiqiang ^b   Shu, Junsheng ^b   She, Shike ^b   Sun, Weifeng ^a   Yin, Chunyan ^a   Chen, Maoshen ^a   Li, Yue ^a   Zhong, Fang ^a  

^a JIANGNAN UNIVERSITY   (China)

^b China Tobacco Anhui Industrial Corporation   (China)

Author keywords

2; 3 Dihydro 3; 5 dihydroxy 6 methyl (4 ) pyran 4 one; DDMP; Maillard reaction; Reaction kinetics; Solid state reaction

Indexed keywords

ACTIVATION ENERGY; AMINO ACIDS; CHEMICAL REACTIONS; DIFFERENTIAL SCANNING CALORIMETRY; GLUCOSE; GLYCOSYLATION; OXYGEN; SOLID STATE REACTIONS; THERMOGRAVIMETRIC ANALYSIS;

2; 3-DIHYDRO-3; DDMP; MAILLARD REACTION; PYRAN-4-ONE;

REACTION KINETICS;

EID: 85027928915     PISSN: 14382377     EISSN: 14382385     Source Type: Journal    
DOI: 10.1007/s00217-014-2191-2     Document Type: Article

References (66)

1. Weenen H (1998) Reactive intermediates and carbohydrate fragmentation in Maillard chemistry. Food Chem 62:393-401
2. Van Boekel MAJS (2006) Formation of favour compounds in the Maillard reaction. Biotechnol adv 24:230-233
3. Fors S (1983) Sensory properties of volatile Maillard reaction products and related compounds. In: The Maillard reaction in foods and nutrition, aCS Symposium Series 215: 185-286
4. lamberts L, Rombouts I, Delcour JA (2008) Study of nonenzy-mic browning in a-amino acid and y-aminobutyric acid/sugar model systems. Food Chem 111:738-744
5. Martins SIFS, Jongen WMF, Van Boekel MAJS (2001) a review of Maillard reaction in food and implications to kinetic modelling. Trends Food Sci Technol 11:364-373
6. Gu F, Kim JM, Hayat K, Xia S, Feng B, Zhang X (2009) Characteristics and antioxidant activity of ultrafltrated Maillard reaction products from a casein-glucose model system. Food Chem 117:48-54
7. Maillard MN, Billaud C, Chow YN, Ordonaud C, Nicolas J (2007) Free radical scavenging, inhibition of polyphenoloxidase activity and copper chelating properties of model Maillard systems. lWT Food Sci Technol 40:1434-1444
8. Hwang IG, Kim HY, Woo KS, lee J, Jeong HS (2011) Biological activities of Maillard reaction products (MRPs) in a sugar-amino acid model system. Food Chem 126:221-227
9. Brands CMJ, Alink GM, van Boekel MAJS, Jongen WMF (2000) Mutagenicity of heated sugar-casein systems: effect of the Maillard reaction. J agric Food Chem 48:2271-2275
10. Nishibori S, Bernhard RA (1993) Model system for cookies: volatile components formed from the reaction of sugar and P-alanine. J agric Food Chem 41:2374-2377
11. Huyghues-Despointes A, Yaylayan VA, Keyhani A (1994) Pyrolysis/gC/MS analysis of 1-[(2'-carboxyl)pyrrolidinyl]-1-de-oxy-D-fructose (proline amadori compound). J agric Food Chem 42:2519-2524
12. Yaylayan VA, Mandeville S (1994) Mechanistic pathway for the formation of maltoxazine from intact 1-[(2'-carboxyl)pyrrolidinyl]-1-deoxy-D-fructose (amadori-Proline). J agric Food Chem 42:1841-1844
13. Davidek T, Clety N, Devaud S, Robert F, Blank I (2003) Simultaneous quantitative analysis of Maillard reaction precursors and products by high-performance anion exchange chromatography. J agric Food Chem 51:7259-7265
14. Nishibori S, Kawakishi S (1992) Effect of various sugars on the quality of baked cookies. Cereal Chem 69:160-163
15. Nishibori S, Kawakishi S (1990) Effects of dough materials on favor formation in baked cookies. J Food Sci 55:409-412
16. Nishibori S, Kawakishi S (1994) Formation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(i/)-pyran-4-one from fructose and P-alanine under conditions used for baking. J agric Food Chem 42:1080-1084
17. Shaw PE, Tatum JH, Berry RE (1971) 2,3-Dihydro-3,5-dihy-droxy-6-methyl-4i/-pyran-4-one, a degradation product of a hex-ose. Carbohydr Res 16:207-211
18. Ledl F, Schnell W, Severin T (1976) nachweis von 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-on in lebensmitteln. Z leb-ensm Unters Forch 160:367–370
19. Kim HJ, Choi YM, Yang APP, Yang TCS, Taub IA, giles J, Ditusa C, Chall S, Zoltai P (1996) Microbiological and chemical investigation of ohmic heating of particulate foods using a 5 kW ohmic system. J Food Process Preserv 20:41–58
20. Wnorowski A, Yaylayan VA (2002) Prediction of process lethality through measurement of Maillard-generated chemical markers. J Food Sci 67:2149–2152
21. Čechovská L, Cejpek K, Konečný M, Velíšek J (2011) On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl-(4H)-pyran-4-one in antioxidant capacity of prunes. Eur Food Res Technol 233: 367–376
22. Buttery RG, ling LC, Stern DJ (1997) Studies on popcorn aroma and favor volatiles. J agric Food Chem 45:837–843
23. Sun J-B, Severson RF, Kays SJ (1993) Quantitative technique for measuring volatile components of baked sweet potatoes. Hort Sci 28:1110–1113
24. Čechovská L, Konečný M, Velíšek J, Cejpek K (2012) Effect of Maillard reaction on reducing power of malts and beers. Czech J Food Sci 30:548–556
25. Barron D, Etiévant PX (1990) The volatile constituents of strawberry jam. Z lebensm Unters Forch 191:279–285
26. Alissandrakis E, Kibaris AC, Tarantilis PA, Harizanis PC, Polis-siou M (2005) Flavour compounds of greek cotton honey. J Sci Food agric 85:1444–1452
27. Green CR (1977) Neutral oxygenated compounds in cigarette smoke and their possible precursors. Rec adv Tob Sci 3:94–120. http://legacy.library.ucsf.edu/tid/ift68d00/pdf. accessed 18 July 2013
28. Hiramoto K, nasuhara A, Michikoshi K, Kato T, Kikugawa K (1997) Dna strand-breaking activity and mutagenicity of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine. Mutat Res 395:47–56
29. Yoshiki Y, Okubo K (1995) active oxygen scavenging activity of DDMP (2,3-dihydro-2, 5-dihydroxy-6-methyl-4H-pyran-4-one) saponin in soybean seed. Biosci Biotechnol Biochem 59:1556–1557
30. Yu X, Zhao M, liu F, Zeng S, Hu J (2013) Identifcation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one as a strong antioxidant in glucose-histidine Maillard reaction products. Food Res Int 51:397–403
31. Shibamoto YOT (2006) Antioxidative activity of volatile extracts from Maillard model systems. Food Chem 98:522–528
32. Takara K, Otsuka K, Wada K, Iwasaki H, Yamashita M (2007) 1,1-Diphenyl-2-picrylhydrazyl radical scavenging activity and tyrosinase inhibitory effects of constituents of sugarcane molasses. Biosci Biotechnol Biochem 71:183–191
33. Ban J, Hwang I, Kim T, Hwang B, lee U, Jeong H-S, Yoon Y, Kim D, Hong J (2007) Anti-proliferate and pro-apoptotic effects of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyranone through inactivation of nF-κB in human colon cancer cells. arch Pharm Res 30:1455–1463
34. Beppu Y, Komura H, Izumo T, Horii Y, Shen J, Tanida M, nakashima T, Tsuruoka N, Nagai K (2012) Identifcation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one isolated from Lactobacillus pentosus strain S-PT84 culture supernatants as a compound that stimulates autonomic nerve activities in rats. J agric Food Chem 60:11044–11049
35. Ashoor SH, Zent JB (1984) Maillard browning of common amino acids and sugars. J Food Sci 49:1206–1207
36. Wnorowski A, Yaylayan VA (2000) Infuence of pyrolytic and aqueous-phase reactions on the mechanism of formation of Mail-lard products. J agric Food Chem 48:3549–3554
37. Kim MO, Baltes W (1996) On the role of 2,3-dihydro-3,5-di-hydroxy-6-methyl-4(H)-pyran-4-one in the Maillard reaction. J agric Food Chem 44:282–289
38. Blank I, Devaud S, Matthey-Doret W, Robert F (2003) Formation of odorants in Maillard model systems based on l-proline as affected by pH. J agric Food Chem 51:3643–3650
39. Britt PF, Buchanan aC, Owens CV Jr, Todd Skeen J (2004) Does glucose enhance the formation of nitrogen containing polycyclic aromatic compounds and polycyclic aromatic hydrocarbons in the pyrolysis of proline? Fuel 83:1417–1432
40. Van Den Dool H, Dec Kratz P (1963) A generalization of the retention index system including linear temperature programmed gas–liquid partition chromatography. J Chromatogr a 11:463–471
41. Baker RR, Bishop LJ (2004) The pyrolysis of tobacco ingredients. J anal appl Pyrolysis 71:223–311
42. Wang W, Wang Y, Yang L, Liu B, Lan M, Sun W (2005) Studies on thermal behavior of reconstituted tobacco sheet. Thermochimi acta 437:7–11
43. Mills FD, Hodge JE (1976) Amadori compounds: vacuum thermolysis of 1-deoxy-1-l-prolino-d-fructose. Carbohydr Res 51:9–21
44. Umano K, Hagi Y, Nakahara K, Shyoji A, Shibamoto T (1995) Volatile chemicals formed in the headspace of a heated d-glucose/l-cysteine Maillard model system. J agric Food Chem 43:2212–2218
45. Blank I, Devaud S, Matthey-Doret W, Pollien P, Robert F, Yeretz-ian C (2003) Formation of odour-active compounds in Maillard model systems based on proline. Flavour Research at the Dawn of the Twenty-First Century: 458–463
46. Leffngwell JC (1976) Nitrogen components of leaf and their relationship to smoking quality and aroma. Rec adv Tob Sci 2:1–31
47. Yang SS, Smetena I (1993) Determination of free amino acids in tobacco by HPlC with fuorescence detection and precolumn derivatization. Chromatographia 37:593–598
48. Ali H, Pätzold R, Brückner H (2006) Determination of l- and d-amino acids in smokeless tobacco products and tobacco. Food Chem 99:803–812
49. Yu XY, Zhao MY, Hu J, Zeng ST, Bai XL (2012) Infuence of pH on the formation and radical scavenging activity of volatile compounds produced by heating glucose with histidine/tyrosine. Eur Food Res Technol 234(2):333–343
50. Yu X, Zhao M, Hu J, Zeng S (2012) Formation and antioxidant activity of volatile compounds produced by heating glucose with tyrosine/histidine in water–ethanol and water–glycerol media. Food Chem 133(4):1394–1401
51. Yu X, Zhao M, Hu J, Zeng S, Bai X (2012) Correspondence analysis of antioxidant activity and UV–vis absorbance of Maillard reaction products as related to reactants. Lwt—Food Sci Tech-nol 46(1):1–9
52. Dills WL (1993) Protein fructosylation: fructose and the Maillard reaction. Am J of Clin nutr 58:779S–787S
53. list B, Lerner Ra, Barbas CF (2000) Proline-catalyzed direct asymmetric aldol reactions. J am Chem Soc 122:2395–2396
54. Moens L, Evans RJ, looker MJ, nimlos MR (2004) A comparison of the Maillard reactivity of proline to other amino acids using pyrolysis-molecular beam mass spectrometry. Fuel 83:1433–1443
55. Sakthivel K, notz W, Bui T, Barbas CF (2001) Amino acid catalyzed direct asymmetric aldol reactions: a bioorganic approach to catalytic asymmetric carbon–carbon bond-forming reactions. J am Chem Soc 123:5260–5267
56. 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
57. Yaylayan VA, Mandeville S (1994) Stereochemical control of maltol formation in Maillard reaction. J agric Food Chem 42:771–775
58. Martins SIFS, Van Boekel MAJS (2005) a kinetic model for the glucose/glycine Maillard reaction pathways. Food Chem 90:257–269
59. Van Boekel MAJS, Martins SIFS (2002) Fate of glycine in the glucose–glycine reaction: a kinetic analysis. Int Congr Ser 1245:289–293
60. Angyal SJ (2001) The lobry de Bruyn-alberda van Ekenstein Transformation and related reactions. In: Stütz a (ed) glycosci-ence: topics in current chemistry, vol 215. Springer, Berlin, pp 1–14
61. Brands CMJ, van Boekel MAJS (2001) Reactions of monosac-charides during heating of sugar–casein systems: building of a reaction network model. J agric Food Chem 49:4667–4675
62. 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
63. Chiavari G, Galletti GC (1992) Pyrolysis—gas chromatogra-phy/mass spectrometry of amino acids. J anal appl Pyrolysis 24:123–137
64. litchfeld JE, Thorpe SR, Baynes JW (1999) Oxygen is not required for the browning and crosslinking of protein by pen-toses: relevance to Maillard reactions in vivo. Int J Biochem Cell Biol 31:1297–1305
65. Pilková L, Pokorný J, Davídek J (1990) Browning reactions of Heyns rearrangement products. Die nahrung 34:759–764
66. Friedman M (1996) Food browning and its prevention: an overview. J agric Food Chem 44:631–653