Simultaneous quantification of amino acids and Amadori products in foods through ion-pairing liquid chromatography-high-resolution mass spectrometry(1089 views) Troise AD, Fiore A, Roviello GN, Monti SM, Fogliano V
Keywords: Amadori Products, Amino Acids, High-Resolution Mass Spectrometry, Maillard Reaction, 1 Amino 1 Deoxy 2 Ketose, Alanine, Arginine, Asparagine, Aspartic Acid, Carbohydrate Derivative, Cysteine, Fructosylarginine, Glutamic Acid, Glycine, Histidine, Isoleucine, Lysine, Methionine, Phenylalanine, Proline, Serine, Threonine, Tryptophan, Tyrosine, Unclassified Drug, Valine, Amino Acid Analysis, Analytic Method, Calibration, Chemical Analysis, Chemical Composition, Controlled Study, Correlation Coefficient, Food Analysis, Food Processing, Food Quality, Glycation, Ion Pair Chromatography, Limit Of Detection, Limit Of Quantitation, Performance Measurement System, Priority Journal, Process Control, Process Development, Quantitative Study, Raw Food, Reproducibility, Sensitivity Analysis, Sensitivity And Specificity, Separation Technique, Tomato, Chemistry, Animals, Cattle, High Pressure Liquid, Lycopersicon Esculentum,
Affiliations: *** IBB - CNR ***
Food Quality Design Group, Wageningen University, PO Box 8129, Wageningen, Netherlands
Department of Agricultural and Food Science, University of Napoli Federico II, Parco Gussone, Portici, Napoli, Italy
Istituto di Biostrutture e Bioimmagini (IBB), CNR, via Mezzocannone 16, Naples, Italy
University of Naples Federico II
Consiglio Nazionale delle Ricerche (CNR)
References: Abrams, A., Lowy, P.H., Borsook, H., Preparation of 1-Amino-1-deoxy-2-ketohexoses from Aldohexoses and α-Amino Acids. I1 (1955) J Am Chem Soc, 77 (18), pp. 4794-4796. , 10.1021/ja01623a030 1:CAS:528:DyaG28XjtFyqug%3D%3
Agostoni, C., Carratù, B., Boniglia, C., Riva, E., Sanzini, E., Free amino acid content in standard infant formulas: Comparison with human milk (2000) J Am Coll Nutr, 19 (4), pp. 434-438. , 10.1080/07315724.2000.10718943 1:CAS:528:DC%2BD3cXmsFOht7s%3D 10963461
Ahmed, N., Advanced glycation endproducts - Role in pathology of diabetic complications (2005) Diabetes Res Clin Pr, 67 (1), pp. 3-21. , 10.1016/j.diabres.2004.09.004 1:CAS:528:DC%2BD2cXhtFGhsb7I
Amadori, M., The condensation product of glucose and p-anisidine (1929) Atti Reale AccadNazlLincei, 9, p. 4
Armbruster, D.A., Pry, T., Limit of blank, limit of detection and limit of quantitation (2008) The Clinical Biochemist Reviews/Australian Association of Clinical Biochemists, 29, pp. S49-S52. , 2556583 18852857
Arnold, U., Ludiwg, E., Kuhn, R., Moschwitzer, U., Analysis of free amino-acids in green coffee beans 1. Determination of amino-acids after precolumn derivatization using 9-fluorenylmethylchloroformate (1994) Z Lebensm Unters For, 199 (1), pp. 22-25
Baisier, W.M., Labuza, T.P., Maillard browning kinetics in a liquid model system (1992) J Agric Food Chem, 40 (5), pp. 707-713. , 10.1021/Jf00017a001 1:CAS:528:DyaK38XitlCjurs%3D
Bosch, L., Alegria, A., Farre, R., Application of the 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) reagent to the RP-HPLC determination of amino acids in infant foods (2006) J Chromatogr B, 831 (1-2), pp. 176-183. , 10.1016/j.jchromb.2005.12.002 1:CAS:528:DC%2BD28Xos1Sgtw%3D%3D
Carli, P., Arima, S., Fogliano, V., Tardella, L., Frusciante, L., Ercolano, M.R., Use of network analysis to capture key traits affecting tomato organoleptic quality (2009) J Exp Bot, 60 (12), pp. 3379-3386. , 10.1093/jxb/erp177 1:CAS:528:DC%2BD1MXhtVWitr%2FI 2724691 19516072
Cosmai, L., Summo, C., Caponio, F., Paradiso, V.M., Gomes, T., Influence of the thermal stabilization process on the volatile profile of canned tomato-based food (2013) J Food Sci, 78 (12), pp. C1865-C1870. , 10.1111/1750-3841.12296 1:CAS:528:DC%2BC3sXhvFWlt77E 24171784
Davidek, T., Clety, N., Devaud, S., Robert, F., Blank, I., Simultaneous quantitative analysis of Maillard reaction precursors and products by high-performance anion exchange chromatography (2003) J Agric Food Chem, 51 (25), pp. 7259-7265. , 10.1021/Jf034794n 1:CAS:528:DC%2BD3sXovVCmu7Y%3D 14640567
Davidek, T., Kraehenbuehl, K., Devaud, S., Robert, F., Blank, L., Analysis of Amadori compounds by high-performance cation exchange chromatography coupled to tandem mass spectrometry (2005) Anal Chem, 77 (1), pp. 140-147. , 10.1021/Ac048925a 1:CAS:528:DC%2BD2cXhtVagt7bF 15623289
Del Castillo, M.D., Corzo, N., Olano, A., Early stages of Maillard reaction in dehydrated orange juice (1999) J Agric Food Chem, 47 (10), pp. 4388-4390. , 10552822
Delatour, T., Hegele, J., Parisod, V., Richoz, J., Maurer, S., Steven, M., Buetler, T., Analysis of advanced glycation endproducts in dairy products by isotope dilution liquid chromatography-electrospray tandem mass spectrometry. The particular case of carboxymethyllysine (2009) J Chromatogr A, 1216 (12), pp. 2371-2381. , 10.1016/j.chroma.2009.01.011 1:CAS:528:DC%2BD1MXis1Gks7o%3D 19181321
Dunn, W.B., Bailey, N.J.C., Johnson, H.E., Measuring the metabolome: Current analytical technologies (2005) Analyst, 130 (5), pp. 606-625. , 10.1039/B418288j 1:CAS:528:DC%2BD2MXjsFOnurw%3D 15852128
Eichner, K.R., Wittmann, R.M., (1990) The Maillard Reaction in Food Processing, Human Nutrition and Physiology, pp. 63-77. , Aeschbacher HU, Hurrel RF, Liardon R (eds) Finot PA. Birkhauser Verlag, Basel, Switzerland
Fenaille, F., Parisod, V., Visani, P., Populaire, S., Tabet, J.-C., Guy, P.A., Modifications of milk constituents during processing: A preliminary benchmarking study (2006) Int Dairy J, 16 (7), pp. 728-739. , 1:CAS:528:DC%2BD28XksVCktbo%3D
Ferrer, E., Alegria, A., Farre, R., Abellan, P., Romero, F., Fluorometric determination of chemically available lysine: Adaptation, validation and application to different milk products (2003) Die Nahrung, 47 (6), pp. 403-407. , 10.1002/food.200390090 1:CAS:528:DC%2BD2cXkslaltQ%3D%3D 14727768
Finot, J.P.A.B., Viani, R., Mauron, J., Identification of a new lysine derivative obtained upon acid hydrolysis of heated milk (1968) Experientia, 24 (24), pp. 1097-1099
Frolov, A., Hoffmann, R., Separation of Amadori peptides from their unmodified analogs by ion-pairing RP-HPLC with heptafluorobutyric acid as ion-pair reagent (2008) Anal Bioanal Chem, 392 (6), pp. 1209-1214. , 10.1007/s00216-008-2377-1 1:CAS:528:DC%2BD1cXht1yqsbrN 18813915
Gadgil, H.S., Bondarenko, P.V., Treuheit, M.J., Ren, D., Screening and sequencing of glycated proteins by neutral loss scan LC/MS/MS method (2007) Anal Chem, 79 (15), pp. 5991-5999. , 10.1021/Ac070619k 1:CAS:528:DC%2BD2sXmsV2lsr0%3D 17571855
Glinsky, G.V., Mossine, V.V., Price, J.E., Bielenberg, D., Glinsky, V.V., Ananthaswamy, H.N., Feather, M.S., Inhibition of colony formation in agarose of metastatic human breast carcinoma and melanoma cells by synthetic glycoamine analogs (1996) Clin Exp Metastasis, 14 (3), pp. 253-267. , 1:CAS:528:DyaK28XkvFelsbc%3D 8674280
Gokmen, V., Serpen, A., Mogol, B.A., Rapid determination of amino acids in foods by hydrophilic interaction liquid chromatography coupled to high-resolution mass spectrometry (2012) Anal Bioanal Chem, 403 (10), pp. 2915-2922. , 10.1007/s00216-012-5779-z 22331053
GonzalezCastro, M.J., LopezHernandez, J., SimalLozano, J., OrunaConcha, M.J., Determination of amino acids in green beans by derivatization with phenylisothiocyanate and high-performance liquid chromatography with ultraviolet detection (1997) J Chromatogr Sci, 35 (4), pp. 181-185. , 1:CAS:528:DyaK2sXitFyqtLg%3D
Gritti, F., Leonardis, I., Abia, J., Guiochon, G., Physical properties and structure of fine core-shell particles used as packing materials for chromatography Relationships between particle characteristics and column performance (2010) J Chromatogr A, 1217 (24), pp. 3819-3843. , 10.1016/j.chroma.2010.04.026 1:CAS:528:DC%2BC3cXmsVOgsrs%3D 20447642
Han, J., Danell, R.M., Patel, J.R., Gumerov, D.R., Scarlett, C.O., Speir, J.P., Parker, C.E., Borchers, C.H., Towards high-throughput metabolomics using ultrahigh-field Fourier transform ion cyclotron resonance mass spectrometry (2008) Metabolomics, 4 (2), pp. 128-140. , 10.1007/s11306-008-0104-8 1:CAS:528:DC%2BD1cXlsFSnt7c%3D 2600444 19081807
Hao, Z., Lu, C.Y., Xiao, B., Weng, N., Parker, B., Knapp, M., Ho, C.T., Separation of amino acids, peptides and corresponding Amadori compounds on a silica column at elevated temperature (2007) J Chromatogr A, 1147 (2), pp. 165-171. , 10.1016/j.chroma.2007.02.057 1:CAS:528:DC%2BD2sXjslGrt7s%3D 17350634
Hegele, J., Buetler, T., Delatour, T., Comparative LC-MS/MS profiling of free and protein-bound early and advanced glycation-induced lysine modifications in dairy products (2008) Anal Chim Acta, 617 (1-2), pp. 85-96. , 10.1016/j.aca.2007.12.027 1:CAS:528:DC%2BD1cXmtVKns7s%3D 18486644
Henle, T., Zehetner, G., Klostermeyer, H., Fast and sensitive determination of furosine (1995) Z Lebensm Unters for, 200 (3), pp. 235-237. , 10.1007/Bf01190503 1:CAS:528:DyaK2MXltVKjs7o%3D
Hodge, J.E., Dehydrated foods, chemistry of browning reactions in model systems (1953) J Agr Food Chem, 1 (15), pp. 928-943. , 10.1021/jf60015a004 1:CAS:528:DyaG2cXht1Gjsg%3D%3D
Horvat, S., Jakas, A., Peptide and amino acid glycation: New insights into the Maillard reaction (2004) J Pept Sci, 10 (3), pp. 119-137. , 10.1002/Psc.519 1:CAS:528:DC%2BD2cXjsFertLc%3D 15113085
Hunt, S., Degradation of amino acids accompanying in vitro protein hydrolysis (1985) Chemistry and Biochemistry of the Amino Acids, pp. 376-398. , Barrett GC (ed). Springer, Netherlands
Kaspar, H., Dettmer, K., Gronwald, W., Oefner, P.J., Advances in amino acid analysis (2009) Anal Bioanal Chem, 393 (2), pp. 445-452. , 10.1007/s00216-008-2421-1 1:CAS:528:DC%2BD1cXht1eitb3L 18843484
Keller, B.O., Sui, J., Young, A.B., Whittal, R.M., Interferences and contaminants encountered in modern mass spectrometry (2008) Anal Chim Acta, 627 (1), pp. 71-81. , 10.1016/j.aca.2008.04.043 1:CAS:528:DC%2BD1cXhtFegtb%2FN 18790129
Kirschner, D.L., Green, T.K., Separation and sensitive detection of d-amino acids in biological matrices (2009) J Sep Sci, 32 (13), pp. 2305-2318. , 10.1002/jssc.200900101 1:CAS:528:DC%2BD1MXptVWrurs%3D 19569111
Langrock, T., Czihal, P., Hoffmann, R., Amino acid analysis by hydrophilic interaction chromatography coupled on-line to electrospray ionization mass spectrometry (2006) Amino Acids, 30 (3), pp. 291-297. , 10.1007/s00726-005-0300-z 1:CAS:528:DC%2BD28Xktlaks7o%3D 16622599
Liu, J., Man, Y., Zhu, Y.C., Hu, X.S., Chen, F., Simultaneous analysis of acrylamide and its key precursors, intermediates, and products in model systems by liquid chromatography-triple quadrupole mass spectrometry (2013) Anal Chem, 85 (19), pp. 9262-9271. , 10.1021/Ac4019928 1:CAS:528:DC%2BC3sXhsVSisL%2FF 24053692
Meitinger, M., Hartmann, S., Schieberle, P., Development of stable isotope dilution assays for the quantitation of Amadori compounds in foods (2014) J Agric Food Chem, 62 (22), pp. 5020-5027
Meltretter, J., Birlouez-Aragon, I., Becker, C.M., Pischetsrieder, M., Assessment of heat treatment of dairy products by MALDI-TOF-MS (2009) Mol Nutr Food Res, 53 (12), pp. 1487-1495. , 10.1002/mnfr.200900008 1:CAS:528:DC%2BD1MXhsFarsrvJ 19760680
Michalski, A., Damoc, E., Lange, O., Denisov, E., Nolting, D., Muller, M., Viner, R., Makarov, A., Ultra high resolution linear ion trap Orbitrap mass spectrometer (Orbitrap Elite) facilitates top down LC MS/MS and versatile peptide fragmentation modes (2012) MCP, 11 (3)
Molero-Vilchez, M.D.W., A new approach to study the significance of Amadori compounds in the Maillard reaction (1997) Food Chem, 58 (3), pp. 249-254. , 1:CAS:528:DyaK2sXpvFCjtQ%3D%3D
Morgan, F., Bouhallab, S., Molle, D., Henry, G., Maubois, J.L., Leonil, J., Lactolation of beta-lactoglobulin monitored by electrospray ionisation mass spectrometry (1998) Int Dairy J, 8 (2), pp. 95-98
Mossine, V.V., Mawhinney, T.P., N-alpha-(1-DeOXY-D-fructos-1-yl)-L-histidine ("D-fructos-L-histidine"): A potent copper chelator from tomato powder (2007) J Agric Food Chem, 55 (25), pp. 10373-10381. , 10.1021/Jf072092i 1:CAS:528:DC%2BD2sXhtlWmu7vE 18004802
Newton, A.E., Fairbanks, A.J., Golding, M., Andrewes, P., Gerrard, J.A., The role of the Maillard reaction in the formation of flavour compounds in dairy products - Not only a deleterious reaction but also a rich source of flavour compounds (2012) Food Funct, 3 (12), pp. 1231-1241. , 10.1039/C2fo30089c 1:CAS:528:DC%2BC38Xhslaiu7jJ 22948260
Nguyen, H.T., Van Der Fels-Klerx, H., Van Boekel, M., Nε-(carboxymethyl) lysine: A review on analytical methods, formation and occurrence in processed food, and health impact (2014) Food Rev Int, , just-accepted
Nordin, P., Kim, Y.S., Browning reactions, browning and the Amadori rearrangement (1958) J Agric Food Chem, 6 (10), pp. 765-766. , 10.1021/jf60092a007 1:CAS:528:DyaG1MXnsVWhtg%3D%3D
Odriozola-Serrano, I., Garde-Cerdán, T., Soliva-Fortuny, R., Martín-Belloso, O., Differences in free amino acid profile of non-thermally treated tomato and strawberry juices (2013) J Food Compos Anal, 32 (1), pp. 51-58. , 1:CAS:528:DC%2BC3sXhvVags7zM
Ozcan, S., Senyuva, H.Z., Improved and simplified liquid chromatography/atmospheric pressure chemical ionization mass spectrometry method for the analysis of underivatized free amino acids in various foods (2006) J Chromatogr A, 1135 (2), pp. 179-185. , 10.1016/j.chroma.2006.09.039 17027997
Petritis, K., Chaimbault, P., Elfakir, C., Dreux, M., Parameter optimization for the analysis of underivatized protein amino acids by liquid chromatography and ionspray tandem mass spectrometry (2000) J Chromatogr A, 896 (1-2), pp. 253-263. , 10.1016/S0021-9673(00)00582-3 1:CAS:528:DC%2BD3cXntlGqtbo%3D 11093660
Petritis, K., Elfakir, C., Dreux, M., A comparative study of commercial liquid chromatographic detectors for the analysis of underivatized amino acids (2002) J Chromatogr A, 961 (1), pp. 9-21. , 1:CAS:528:DC%2BD38XltFWjsbs%3D 12186396 10.1016/S0021-9673(02)00377-1
Rao, Q.C., Rocca-Smith, J.R., Schoenfuss, T.C., Labuza, T.P., Accelerated shelf-life testing of quality loss for a commercial hydrolysed hen egg white powder (2012) Food Chem, 135 (2), pp. 464-472. , 10.1016/j.foodchem.2012.05.025 1:CAS:528:DC%2BC38XhtVehs7nJ 22868115
Reutter, M., Eichner, K., Separation and determination of Amadori compounds by high-pressure liquid-chromatography and post-column reaction (1989) Z Lebensm Unters for, 188 (1), pp. 28-35. , 10.1007/Bf01027618 1:CAS:528:DyaL1MXitFWjtLg%3D
Sanz, M.L., Del Castillo, M.D., Corzo, N., Olano, A., Presence of 2-furoylmethyl derivatives in hydrolysates of processed tomato products (2000) J Agric Food Chem, 48 (2), pp. 468-471. , 10.1021/Jf990697b 1:CAS:528:DC%2BD3cXmsFCi 10691658
Schlichtherle-Cerny, H., Affolter, M., Cerny, C., Hydrophilic interaction liquid chromatography coupled to electrospray mass spectrometry of small polar compounds in food analysis (2003) Anal Chem, 75 (10), pp. 2349-2354. , 10.1021/Ac026613p 1:CAS:528:DC%2BD3sXivFagur4%3D 12918976
Silván, J.M., Van De Lagemaat, J., Olano, A., Del Castillo, M.D., Analysis and biological properties of amino acid derivates formed by Maillard reaction in foods (2006) J Pharm Biomed Anal, 41 (5), pp. 1543-1551. , 16824722
Singh, R., Barden, A., Mori, T., Beilin, L., Advanced glycation end-products: A review (2001) Diabetologia, 44 (2), pp. 129-146. , 10.1007/s001250051591 1:CAS:528:DC%2BD3MXntlSltg%3D%3D 11270668
Srinivas, S.M., Harohally, N.V., Improved synthesis of lysine- and arginine-derived amadori and Heyns products and in vitro measurement of their angiotensin i-converting enzyme inhibitory activity (2012) J Agric Food Chem, 60 (6), pp. 1522-1527. , 10.1021/Jf204185y 1:CAS:528:DC%2BC38Xntlahug%3D%3D 22242891
Staempfli, A.A., Blank, I., Fumeaux, R., Fay, L.B., Study on the decomposition of the Amadori compound N-(1-deoxy-D-fructos-1-y1)-glycine in model systems: Quantification by fast atom bombardment tandem mass spectrometry (1994) Biol Mass Spectrom, 23 (10), pp. 642-646. , 10.1002/bms.1200231007 1:CAS:528:DyaK2cXmsl2iurk%3D
Troise, A.D., Fiore, A., Fogliano, V., Quantitation of Acrylamide in foods by high-resolution mass spectrometry (2013) J Agric Food Chem, , 10.1021/jf404205b
Troise, A.D., Ferracane, R., Palermo, M., Fogliano, V., Targeted metabolite profile of food bioactive compounds by Orbitrap high resolution mass spectrometry: The "FancyTiles" approach (2014) Food Res Int
Van Boekel, M.A.J.S., Formation of flavour compounds in the Maillard reaction (2006) Biotechnol Adv, 24 (2), pp. 230-233. , 10.1016/j.biotechadv.2005.11.004 16386869
Ventura, A.K., San Gabriel, A., Hirota, M., Mennella, J.A., Free amino acid content in infant formulas (2012) Nutr Food Sci, 42 (4), pp. 271-278
Vinale, F., Fogliano, V., Schieberle, P., Hofmann, T., Development of a stable isotope dilution assay for an accurate quantification of protein-bound N-epsilon-(1-deoxy-D-fructos-1-yl)-L-lysine using a C-13-labeled internal standard (1999) J Agric Food Chem, 47 (12), pp. 5084-5092. , 10.1021/Jf9904315 1:CAS:528:DyaK1MXnsFOnsbo%3D 10606577
Wnorowski, A., Yaylayan, V.A., Influence of pyrolytic and aqueous-phase reactions on the mechanism of formation of Maillard products (2000) J Agric Food Chem, 48 (8), pp. 3549-3554. , 10.1021/jf9913099 1:CAS:528:DC%2BD3cXkvFamtLg%3D 10956148
Wrodnigg, T.M., Eder, B., The Amadori and Heyns rearrangements: Landmarks in the history of carbohydrate chemistry or unrecognized synthetic opportunities? (2001) Top Curr Chem, 215, pp. 115-152. , 1:CAS:528:DC%2BD3MXls1eks7o%3D
Yang, W.C., Mirzaei, H., Liu, X.P., Regnier, F.E., Enhancement of amino acid detection and quantification by electrospray ionization mass spectrometry (2006) Anal Chem, 78 (13), pp. 4702-4708. , 10.1021/Ac0600510 1:CAS:528:DC%2BD28XksFKktb4%3D 16808485
Yaylayan, V.A., Huyghuesdespointes, A., Chemistry of Amadori rearrangement products - Analysis, synthesis, kinetics, reactions, and spectroscopic properties (1994) Crit Rev Food Sci, 34 (4), pp. 321-369. , 1:CAS:528:DyaK2MXovFyjtw%3D%3D
Simultaneous quantification of amino acids and Amadori products in foods through ion-pairing liquid chromatography-high-resolution mass spectrometry
Kállay C, Dávid A, Timári S, Nagy EM, Sanna D, Garribba E, Micera G, De Bona P, Pappalardo G, Rizzarelli E, Sóvágó I * Copper(II) complexes of rat amylin fragments(357 views) Dalton T (ISSN: 1477-9234, 1477-9226, 1477-9234electronic), 2011 Oct 14; 40(38): 9711-9721. Impact Factor:3.838 ViewExport to BibTeXExport to EndNote