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Lysine-Derived Protein-Bound Heyns Compounds in Bakery Products.
J Agric Food Chem. 2017 Dec 06; 65(48):10562-10570.JA

Abstract

Fructose and dicarbonyl compounds resulting from fructose in heated foods have been linked to pathophysiological pathways of several metabolic disorders. Up to now, very little has been known about the Maillard reaction of fructose in food. Heyns rearrangement compounds (HRCs), the first stable intermediates of the Maillard reaction between amino components and fructose, have not yet been quantitated as protein-bound products in food. Therefore, the HRCs glucosyllysine and mannosyllysine were synthesized and characterized by NMR. Protein-bound HRCs in cookies containing various sugars and in commercial bakery products were quantitated after enzymatic hydrolysis by RP-HPLC-ESI-MS/MS in the multiple reaction monitoring mode through application of the standard addition method. Protein-bound HRCs were quantitated for the first time in model cookies and in commercial bakery products containing honey, banana, and invert sugar syrup. Concentrations of HRCs from 19 to 287 mg/kg were found, which were similar to or exceeded the content of other frequently analyzed Maillard reaction products, such as N-ε-carboxymethyllysine (10-76 mg/kg), N-ε-carboxyethyllysine (2.5-53 mg/kg), and methylglyoxal-derived hydroimidazolone 1 (10-218 mg/kg) in the analyzed cookies. These results show that substantial amounts of HRCs form during food processing. Analysis of protein-bound HRCs in cookies is therefore useful to evaluate the Maillard reaction of fructose.

Authors+Show Affiliations

Institute of Food Chemistry, Technische Universität Dresden , D-01062 Dresden, Germany.Institute of Food Chemistry, Technische Universität Dresden , D-01062 Dresden, Germany.Institute of Food Chemistry, Technische Universität Dresden , D-01062 Dresden, Germany.Institute of Food Chemistry, Technische Universität Dresden , D-01062 Dresden, Germany.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29111707

Citation

Treibmann, Stephanie, et al. "Lysine-Derived Protein-Bound Heyns Compounds in Bakery Products." Journal of Agricultural and Food Chemistry, vol. 65, no. 48, 2017, pp. 10562-10570.
Treibmann S, Hellwig A, Hellwig M, et al. Lysine-Derived Protein-Bound Heyns Compounds in Bakery Products. J Agric Food Chem. 2017;65(48):10562-10570.
Treibmann, S., Hellwig, A., Hellwig, M., & Henle, T. (2017). Lysine-Derived Protein-Bound Heyns Compounds in Bakery Products. Journal of Agricultural and Food Chemistry, 65(48), 10562-10570. https://doi.org/10.1021/acs.jafc.7b04172
Treibmann S, et al. Lysine-Derived Protein-Bound Heyns Compounds in Bakery Products. J Agric Food Chem. 2017 Dec 6;65(48):10562-10570. PubMed PMID: 29111707.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lysine-Derived Protein-Bound Heyns Compounds in Bakery Products. AU - Treibmann,Stephanie, AU - Hellwig,Anne, AU - Hellwig,Michael, AU - Henle,Thomas, Y1 - 2017/11/17/ PY - 2017/11/8/pubmed PY - 2018/1/3/medline PY - 2017/11/8/entrez KW - HPLC−MS/MS KW - Heyns compound KW - Maillard reaction KW - bakery product KW - fructose KW - glycation SP - 10562 EP - 10570 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 65 IS - 48 N2 - Fructose and dicarbonyl compounds resulting from fructose in heated foods have been linked to pathophysiological pathways of several metabolic disorders. Up to now, very little has been known about the Maillard reaction of fructose in food. Heyns rearrangement compounds (HRCs), the first stable intermediates of the Maillard reaction between amino components and fructose, have not yet been quantitated as protein-bound products in food. Therefore, the HRCs glucosyllysine and mannosyllysine were synthesized and characterized by NMR. Protein-bound HRCs in cookies containing various sugars and in commercial bakery products were quantitated after enzymatic hydrolysis by RP-HPLC-ESI-MS/MS in the multiple reaction monitoring mode through application of the standard addition method. Protein-bound HRCs were quantitated for the first time in model cookies and in commercial bakery products containing honey, banana, and invert sugar syrup. Concentrations of HRCs from 19 to 287 mg/kg were found, which were similar to or exceeded the content of other frequently analyzed Maillard reaction products, such as N-ε-carboxymethyllysine (10-76 mg/kg), N-ε-carboxyethyllysine (2.5-53 mg/kg), and methylglyoxal-derived hydroimidazolone 1 (10-218 mg/kg) in the analyzed cookies. These results show that substantial amounts of HRCs form during food processing. Analysis of protein-bound HRCs in cookies is therefore useful to evaluate the Maillard reaction of fructose. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/29111707/Lysine_Derived_Protein_Bound_Heyns_Compounds_in_Bakery_Products_ L2 - https://doi.org/10.1021/acs.jafc.7b04172 DB - PRIME DP - Unbound Medicine ER -