Mass spectrometric detection and formation of D-amino acids in processed plant saps, syrups, and fruit juice concentrates

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 25, 2005, Pages 9722-9729

  Pätzold, Ralf ^a   Brückner, Hans ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

Amadori compounds; Amino acid racemization; Chirasil Val; Dietary plant saps; GC SIM MS; Maillard reaction

Indexed keywords

AMINO ACID;

ACER; ARECACEAE; ARTICLE; BEVERAGE; BIRCH; CHEMISTRY; FRUIT; GLYCATION; MASS FRAGMENTOGRAPHY; PLANT; STEREOISOMERISM;

ACER; AMINO ACIDS; ARECACEAE; BETULA; BEVERAGES; FRUIT; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAILLARD REACTION; PLANTS; STEREOISOMERISM;

ACER; AGAVE; CERATONIA SILIQUA; LYTHRACEAE; MALUS X DOMESTICA; PYRUS COMMUNIS; SACCHARUM; SACCHARUM HYBRID CULTIVAR; VITIS SP.;

EID: 29744442501     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf051433u     Document Type: Article

References (50)

1. Robinson, T. D-amino acids in higher plants. Life Sci. 1976, 19, 1097-1102.
2. Brückner, H.; Westhauser, T. Chromatographic determination of D-amino acids as native constituents of vegetables and fruits. Chromatographia 1994, 39, 419-426.
3. Brückner, H.; Westhauser, T. Chromatographic determination of L- and D-amino acids in plants. Amino Acids 2003, 24, 43-55.
4. Ogawa, T.; Fukuda, M. Occurrence of D-amino acid aminotransferase in pea seedlings. Biochem. Biophys. Res. Commun. 1973, 52, 998-1002.
5. Ogawa, T.; Kawasaki, Y.; Sasaoka, K. De novo synthesis of D-alanine in germinating Pisum sativum seedlings. Phytochemistry 1978, 17, 1275-1276.
6. Hayase, F.; Kato, M.; Fujimaki, M. Racemization of amino acid residues in proteins and poly(L-amino acids) during roasting. J. Agric. Food Chem. 1975, 23, 491-494.
7. Masters, P. M.; Friedman, M. Racemization of amino acids in alkali-treated food proteins. J. Agric. Food Chem. 1979, 27, 507-511.
8. Liardon, R.; Hurrell, R. F. Amino acid racemization in heated and alkali-treated proteins. J. Agric. Food Chem. 1983, 31, 432-437.
9. Man, E. H.; Bada, J. L. Dietary D-amino acids. Annu. Rev. Nutr. 1987, 7, 209-225.
10. Brückner, H.; Becker, D.; Lüpke, M. Chirality of amino acids of microorganism used in food biotechnology. Chirality 1993, 5, 385-392.
11. Friedman, M. Chemistry, nutrition, and microbiology of D-amino acids. J. Agric. Food Chem. 1999, 47, 3457-3479.
12. Gandolfi, I.; Palla, G.; Delprato, L.; De Nisco, F.; Marchelli, R.; Salvadori, C. D-amino acids in milk as related to heat treatments and bacterial activity. J. Food Sci. 1992, 57, 377-379.
13. Gandolfi, I.; Palla, G.; Marchelli, R.; Dossena, A.; Puelli, S.; Salvadori, C. D-alanine in fruit juices: A molecular marker of bacterial activity, heat treatments and shelf-life. J. Food Sci. 1994, 59, 152-154.
14. Brückner, H.; Lüpke, M. Determination of amino acid enantiomers in orange juices by chiral phase capillary gas chromatography. Chromatographia 1991, 31, 123-128.
15. Brückner, H.; Langer, M.; Lüpke, M.; Westhauser, T.; Godel, H. Liquid chromatographic determination of amino acid enantiomers by derivatisation with o-phthaldialdehyd and chiral thiols. Application with reference to food science. J. Chromatogr. A 1995, 697, 229-245.
16. Calabrese, M.; Stancher, B. A study of the proline isomerisation in typical Italian wines. J. Sci. Food Agric. 1999, 79, 1357-1360.
17. Casal, S.; Mendes, E.; Oliveira, M. B. P. P.; Ferreira, M. A. Roast effects on coffee amino acid enantiomers. Food Chem. 2005, 89, 333-340.
18. Pawlowska, M.; Armstrong, D. W. Evaluation of enantiomeric purity of selected amino acids in honey. Chirality 1994, 6, 270-276.
19. Pätzold, R.; Nieto-Rodriguez, A.; Brückner, H. Chiral gas chromatographic analysis of amino acids in fortified wines. Chromatographia Suppl. 2003, 57, S207-S211.
20. Erbe, T.; Brückner, H. Studies on the optical isomerization of dietary amino acids in vinegar and aqueous acetic acid. Eur. J. Food Res. Technol. 2000, 211, 6-12.
21. Brückner, H.; Justus, J.; Kirschbaum, J. Saccharide induced racemization of amino acids in the course of the Maillard reaction. Amino Acids 2001, 21, 429-433.
22. Hodge, J. E. Chemistry of browning reactions in model systems. J. Agric. Food Chem. 1953, 1, 928-943.
23. Friedman, M. Food browning and its prevention: an overview. J. Agric. Food Chem. 1996, 44, 631-653.
24. Ledl, F.; Schleicher, E. New aspects of the Maillard reaction in foods and in the human body. Angew. Chem., Int. Ed. Engl. 1990, 29, 565-594.
25. O'Brien, J., Nursten, H. E., Crabbe, M. J. C., Ames, J. M., Eds. The Maillard Reaction in Foods and Medicine; Proceedings of the 6th International Symposium on the Maillard Reaction, London, U.K., July 27-30, 1997; The Royal Society of Chemistry: Cambridge, U.K., 1998.
26. Ames, J. M. Applications of the Maillard reaction in the food industry. Food Chem. 1998, 62, 431-439.
27. Winkler, O. Beitrag zum Nachweis und zur Bestimmung von Oxymethylfurfural in Honig und Kunsthonig. Z. Lebensm.-Unters. Forsch. 1955, 102, 160-167.
28. Frank, H.; Nicholson, G. J.; Bayer, E. Gas chromatographic - mass spectrometric analysis of optically active metabolites and drugs on a novel chiral stationary phase. J. Chromatogr. 1978, 146, 197-206.
29. Yaylayan, V. A.; Huyghues-Despointes, A. Chemistry of Amadori rearrangement products: analysis, synthesis, kinetics, reactions and spectroscopic properties. Crit. Rev. Food Sci. Nutr. 1994, 34, 321-369.
30. Moll, M.; Gross, B. Isolation and purification of Amadori compounds by semipreparative reversed phase high performance liquid chromatography. J. Chromatogr. 1979, 2, 186-192.
31. Stuckel, J. G.; Low, N. H. The chemical composition of 80 pure maple syrup samples produced in North America. Food Res. Int. 1996, 29, 373-379.
32. Ahtonen, S.; Kallio, H. Identification and seasonal variations of amino acids in birch sap used for syrup production. Food Chem. 1989, 33, 125-132.
33. Tomomatsu, A.; Itoh, T.; Wijaya, C. H.; Nasution, Z.; Kumendong, J.; Matsuyama, A. Chemical constituents of sugar-containing sap and brown sugar from palm in Indonesia. Jpn. J. Trop. Agric. 1996, 40, 175-181.
34. Mancilla-Margalli, N. A.; Lopez, M. G. Generation of Maillard compounds from inulin during the thermal processing of Agave tequilana Weber var. azul. J. Agric. Food Chem. 2002, 50, 806-812.
35. Bozkurt, H.; Gögus, F. K.; Eren, S. Nonenzymic browning reactions in boiled grape juice and its models during storage. Food Chem. 1999, 64, 89-93.
36. Booij, I.; Piombo, G.; Risterucci, J. M.; Thomas, D.; Ferry, M. Sugar and free amino acid composition of five cultivars of dates from offshoots or vitroplants in open fields. J. Agric. Food Chem. 1993, 41, 1553-1557.
37. Anet, E. F. L. J.; Reynolds, T. M. Reactions between amino acids, organic acids and sugars in freeze dried apricots. Nature 1956, 177, 1082.
38. Ciner-Doruk, M.; Eichner, K. Bildung und Stabilität von Amadori-Verbindungen in wasserarmen Lebensmitteln (in German). Z. Lebensm.-Unters. Forsch. 1979, 168, 9-20.
39. Sanz, M. L.; del Castillo, M. D.; Corzo, N.; Olano, A. Formation of Amadori compounds in dehydrated fruits. J. Agric. Food Chem. 2001, 49, 5228-5231.
40. Davidek, T.; Kraehenbuehl, K.; Devaud, S.; Robert, F.; Blank, I. Analysis of Amadori compounds by high-performance cation exchange chromatography coupled to tandem mass spectrometry. Anal. Chem. 2005, 77, 140-147.
41. Hashiba, H. Participation of Amadori rearrangement products and carbonyl compounds in oxygen-dependent browning of soy sauce. J. Agric. Food Chem. 1976, 24, 70-73.
42. van Boekel, M. A. J. S. Effect of heating in Maillard reactions in milk. Food Chem. 1998, 62, 403-414.
43. Noguchi, M.; Satoh, Y.; Nishida, K.; Ando, S.; Tamaki, E. Studies on storage and ageing of leaf tobacco. Part IX. Changes in the content of amino acid-sugar compounds during ageing. Agric. Biol. Chem. 1971, 35, 65-70.
44. Ali, H.; Pätzold, R.; Brückner, H. Determination of L- and D-amino acids in smokeless tobacco products and tobacco. Food Chem. 2005, in press.
45. Pätzold, R.; Kutz, N.; Brückner H. Determination of D-amino acids in cocoa beans (Theobroma cacao L.) and cocoa products. Amino Acids 2005, 29, 64.
46. Cremer, D. R.; Eichner, K. The reaction kinetics for the formation of Strecker aldehydes in low moisture model systems and in plant powders. Food Chem. 2000, 71, 37-43.
47. Cremer, D. R.; Eichner, K. The influence of the pH value on the formation of Strecker aldehydes in low moisture model systems and in plant powders. Eur. Food Res. Technol. 2000, 211, 247-251.
48. Van Boekel, M. A J. S. Kinetic aspects of the Maillard reaction: a critical review. Nahrung/Food 2001, 45, 150-159.
49. del Castillo, M. D.; Corzo, N.; Polo, M. C.; Pueyo, E.; Olano, A. Changes in the amino acid composition of dehydrated orange juices during accelerated nonenzymatic browning. J. Agric. Food Chem. 1998, 46, 277-280.
50. Kroh, L. W.; Jalyschko, W.; Häseler, J. Non-volatile reactions products by heat-induced degradation of α-glucans. Part 1: Analysis of oligomeric maltodextrins and anhydrosugars. Starch 1996, 48, 426-433.