Identification of hydroxycinnamic acid - maillard reaction products in low-moisture baking model systems

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 21, 2009, Pages 9932-9943

  Deshou, Jiang ^a   Christopher, Chiaro ^b   Pranav, Maddali ^b   Sandeep, K ^b   Peterson, Devin G ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Hydroxycinnamic acids; Inos and cox 2 suppression; Maillard reaction; Maillard phenolic reaction product; Pericyclic reaction

Indexed keywords

COUMARIC ACID; GLUCOSE; GLYCINE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; FOOD HANDLING; GLYCATION; HEAT; HUMIDITY;

COUMARIC ACIDS; FOOD HANDLING; GLUCOSE; GLYCINE; HOT TEMPERATURE; HUMIDITY; MAILLARD REACTION; MODELS, CHEMICAL;

BACTERIA (MICROORGANISMS); MURINAE;

EID: 70449101166     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf900932h     Document Type: Article

References (37)

1. (1) Vitaglione, P.; Napolitano, A.; Fogliano, V. Cereal dietary fiber; a natural functional ingredient to deliver phenolic compounds into the gut. Trends Food Sci. Technol. 2008, 19, 451-463. (Pubitemid 352004153)
2. (2) Bakke, A.; Vickers, Z. Consumer liking of refined and whole wheat bread, J. Food Sci. 2007, 72, S473-S480. (Pubitemid 47373520)
3. Heinio, R. L.; Liukkonen, K. H.; Myllyma, O.; Pihlava, J. M.; Adlercreutz, H.; Heinonen, S. M.; Poutanen, K. Quantities of phenolic compounds and their impacts on the perceived flavour attributes of rye grain. J. Cereal Sci. 2008, 47, 566-575.
4. Drewnowski, A. Taste preferences and food intake, Annu Rev. Nutr. 1997, 17, 237-253.
5. Peterson, D. G.; Noda, Y. Role of phenolic reactions on Maillard reaction flavors. In Recent Highlights in Flavor Chemistry and Biology, Proceedings of the 8th Wartburg Symposium, Eisenach, Germany, 2007; Hofmann, T., Meyerhof, W., Schieberle, P., Eds.; Deutsche Forschungsanstalt fur Lebensmittelchemie: Eisenach, Germany, 2007; p 443.
6. Wang, Y. Effects of naturally occurring phenolic compounds on the formation of Maillard aroma. Ph.d. dissertation, Rutgers State University, 2000.
7. Li, L.; Shewry, P. R.; Ward, J. L. Phenolic acids in wheat varieties in. the HEALTHGRAIN diversity screen. J. Agric. Food Chem. 2008, 56, 9732-9739.
8. Baynes, J.; Monnier, V.; Ames, J.; Thorpe, S. The Maillard reaction: chemistry at the interface of nutrition, aging, and disease. In 8th International Symposium on the Maillard Reaction; Baynes, J., Monnier, V. M., Ames, J. M., Thorpe, S. R., Eds.; New York Academy of Sciences: Charleston, SC, 2004; Vol. 1043, p 954.
9. Friedman, M. Food browning and its prevention: overview. J. Agric. Food Chem. 1996, 44, 631-653.
10. Namiki, M. Chemistry of Maillard reactions: recent studies on the browning reaction mechanism and the development of antioxidants and mutagens, Adv. Food Res. 1988, 32, 115-184.
11. Schneeman, B. O.; Dunaif, G. Nutritional and gastrointestinal response to heated nonfat dry milk. J. Agric. Food Chem. 1984, 32, 477-480.
12. Wakabayashi, K.; Takahashi, M.; Nagao, M.; Sato, S.; Kinae, N.; Tomita, I.; Sugimura, T. Quantification of mutagenic and carcinogenic heterocyclic amines in cooked foods. In Amino-Carbonyl Reactions in Food and Biological Systems; Fujimaki, M., Namiki, M., Kato, H., Eds.; Kodansha: Tokyo, Japan, 1986; pp 363-371.
13. Randhir, R.; Kwon, Y.; Shetty, K. Effects of thermal processing on phenolics, antioxidant activity and health-relvevant functionality of select grain sprouts and seedlings, Innovative Food Sci. Emerging Technol. 2008, 9, 355-364.
14. Palempalli, U. D.; Gandhi, U.; Kalantari.P.; Vunta, H.; Arner, R. J.; Narayan, V.; Ravindran, A.; Prabhu, K. S. Gambogic acid covalently modifies IkB-kinase-β subunit to mediate suppression of lipopolysaccharide-induced activation of NF-kB in macrophages. Biochem. J. 2009, 419 (2), 401-409.
15. Colahan-Sederstrom, P. M.; Peterson, D. G. Inhibition of key aroma compound generated during ultrahigh-temperature processing of bovine milk via epicatechin addition. J. Agric. Food Chem. 2005, 53, 398-402.
16. Noda, Y.; Peterson, D. G. Structure-reactivity relationships of flavan-3-ols on product generation in aqueous glucose/glycine model systems. J. Agric. Food Chem. 2007, 55, 3686-3691.
17. Schwambach, S. L.; Peterson, D. G. Reduction of stale flavor development in low-heat skim milk powder via epicatechin addition. J. Agric. Food Chem. 2006, 54, 502-508.
18. Totlani, V. M.; Peterson, D. G. Reactivity of epicatechin. in aqueous glycine and glucose maillard reaction models: quenching of C2, C3, and C4 sugar fragments. J. Agric. Food Chem. 2005, 53, 4130-4135.
19. Totlani, V. M.; Peterson, D. G. Epicatechin carbonyl-trapping reactions in aqueous maillard systems: identification and structural elucidation. J. Agric. Food Chem. 2006, 54, 7311-7318.
20. Totlani, V. M.; Peterson, D. G. Influence of epicatechin reactions on the mechanisms of Maillard product formation in low moisture model systems. J. Agric. Food Chem. 2007, 55, 414-420.
21. Schieberle, P.; Fischer, R.; Hofmann, T. The carbohydrate modul labeling - a useful tool to clarify formation pathways of aroma compounds formed in Maillard-type reactions. In Flavor Research at the Dawn of the Twenty-First Century; Le Quéré, J. L., Etiévant, P. X., Eds.; Lavoisier: Paris, France, 2003; pp 447-452.
22. 15N isotope studies and analysis by electrspray ionization-mass spectrometry. Food Chem. 1998, 62 (2), 179-183.
23. Stark, T.; Hofmann, T. Application of a molecular sensory science approach to alkalized cocoa (Theobroma cacao): structure determination and sensory activity of nonenzymatically C-glycosylated flavan-3-ols. J. Agric. Food Chem. 2006, 54, 9510-9521.
24. Snider, B. B. Synthesis of the 5-hydroxymethyl-6-aryl-8-oxabicyclo[3.2.1] oct-3-en-2-one natural products descurainin and cartorimine. Tetrahedron 2006, 62, 5171-5177.
25. Wen, Y.; He, S.; Xue, K.; Cao, F. Studies on. chemical constituents of Ligusticum chuanxiong. Chem. Abstr. 1986, 105, 75884m.
26. Cohen, L. A study of pH dependence in the decarboxylation of p-hydroxycinnamic acid. J. Am. Chem. Soc. 1959, 52, 1907-1911.
27. Sun, K.; Li, X.; Li, W.; Wang, J.; Liu, J.; Sha, Y. Two new lactones and one new aryl-8-oxa-bicyclo[3,2,1]oct-3-en-2-one from Descurainia sophia. Chem. Pharm. Bull. 2004, 52 (12), 1483-1486.
28. Chuyen, N. V. Studies on the reaction of dipeptides with glyoxal. Agric. Biol. Chem. 1973, 37(2), 327-334.
29. (29) Yaylayan, V. A.; Keyhani, A. Glycine specific novel Maillard reaction products: 5-hydroxy-1,3-dimethyl-2(1H)-quinoxalinoiie and related compunds. J. Agric. Food Chem. 1997, 45, 697-702. (Pubitemid 127483691)
30. (30) Frank, O.; Blumberg, S.; Kunert, C.; Zehentbauer, G.; Hofmann, T. Structure determination, and sensory analysis of bitter-tasting 4-vinylcatechol oligomers and their identification in roasted coffee by means of LC-MS/MS. J. Agric. Food Chem. 2007, 55, 1945-1954. (Pubitemid 46479605)
31. Farmař, J.; Ulrich, P.; Cerami, A. Novel pyrroles from sulfiteinhibited Maillard reactions: insight into the mechanism of inhibition, J. Org. Chem. 1988, 53, 2346-2349.
32. Bekedam, E. K.; Schols, H. A.; Van Boekel, M. A.; Smit, G. Incorporation of chlorogenic acids in. coffee brew melanoidins. J. Agric. Food. Chem. 2008, 56, 2055-2063.
33. Rizzi, G. P. Free radicals in the Maillard reaction. Food Rev. Int. 2003, 19 (4), 375-395.
34. Hofmann, T.; Bors, W.; Stettmaier, K. Studies on radical intermediates in the early stage of the nonenzymatic browning reaction of carbohydrates and amino acids. J. Agric. Food Chem. 1999, 47, 379390.
35. Namiki, M.; Hayashi, T. Developments of novel free radicals during the amino-carbonyl reactions of sugars with amino acid. J. Agric. Food. Chem. 1975, 23, 487-491.
36. Namiki, M.; Hayashi, T.; Kawakishi, S. Free radicals developed in the amino-carbonyl reaction of sugars with amino acids, Agric. Biol. Chem 1973, 37, 2935-2936.
37. Mitsuda, H.; Yasumoto, K.; Yokoyama, K. Studies on the free radical in amino-carbonyl reaction, Agric. Biol. Chem. 1965, 29, 751-756.