Kinetics of formation of fluorescent products from hexanal and L-lysine in a two-phase system

Lipids

Volumn 31, Issue 11, 1996, Pages 1125-1132

  Stapelfeldt, Henrik ^a   Skibsted, Leif H ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; HEXANE; LYSINE;

ARTICLE; FLAME PHOTOMETRY; FLUORESCENCE; LIPID PEROXIDATION; MEAT INDUSTRY; TEMPERATURE DEPENDENCE;

ALDEHYDES; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; KINETICS; LIPID PEROXIDATION; LYSINE; MODELS, BIOLOGICAL; OXIDATION-REDUCTION; SPECTROMETRY, FLUORESCENCE;

EID: 0029855621     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02524286     Document Type: Article

References (39)

1. Montgomery, M.W., and Day, E.A. (1965) Aldehyde-Amine Condensation Reaction: A Possible Fate of Carbonyls in Foods, J. Food Sci. 30, 828-832.
2. Kikugawa, K. (1986) Fluorescent Products Derived from the Reaction of Primary Amines and Components in Peroxidized Lipids, Adv. Free Radical Biol. Med. 2, 389-417.
3. Chio, K.S., Reiss, U., Fletcher, B., and Tappel, A.L. (1969) Peroxidation of Subcellular Organelles: Formation of Lipofuscin-like Fluorescent Pigments, Science 166, 1535-1536.
4. Dillard, C., and Tappel, A.L. (1971) Fluorescent Products of Lipid Peroxidation of Mitochondria and Microsomes, Lipids 6, 715-721.
5. Gray, J.I. (1978) Measurement of Lipid Oxidation: A Review, J. Am. Oil Chem. Soc. 55, 539-546.
6. Stapelfeldt, H., Bjørn, H., Skovgaard, I.M., Skibsted, L.H., and Bertelsen, G. (1992) Warmed-Over Flavour in Cooked Sliced Beef. Chemical Analysis in Relation to Sensory Evaluation, Z. Lebensm. Unter.-Forsch. 195, 203-208.
7. Guthrie, F.E., and Hodgson, E. (1987) Absorption and Distribution of Toxicants, in A Textbook of Modern Toxicology (Hodgson, E., and Levi, P.E., eds.) pp. 23-50, Elsevier, New York.
8. Esterbauer, H. (1982) Aldehydic Products of Lipid Peroxidation, in Free Radicals, Lipid Peroxidation and Cancer (McBrien, D.C.H., and Slater, T.F., eds.) pp. 101-128, Academic Press, London.
9. Elleder, M. (1981) Chemical Characterization of Age Pigments, in Age Pigments (Sohal, R.S., ed.) pp. 204-241, Elsevier, Amsterdam.
10. Chio, K.S., and Tappel, A.L. (1969) Inactivation of Ribonuclease and Other Enzymes by Peroxidizing Lipids and by Malonaldehyde, Biochemistry 8, 2827-2832.
11. Kikugawa, K., Maruyama, T., Machida, Y., and Kurechi, T. (1981) Studies on Peroxidized Lipids. II. Fluorescent Products Relevant to Aging Pigments Derived from Malondialdehyde and Methylamine, Chem. Pharm. Bull. 29, 1423-1432.
12. Kikugawa, K., Machida, Y., Kida, M., and Kurechi, T. (1981) Studies on Peroxidized Lipids. III. Fluorescent Pigments Derived from the Reaction of Malonaldehyde and Amino Acids, Chem. Pharm. Bull. 29, 3003-3011.
13. Eldred, G.E., and Katz, M.L. (1989) The Autofluorescent Products of Lipid Peroxidation May Not Be Lipofuscin-Like, Free Radical Biol. Med. 7, 157-163.
14. Minamide, Y., Horie, T., Itoh, F., and Awazu, S. (1990) Fluorescence Lifetimes of Fluorescent Substances Formed in Peroxidized Microsomes of Rat Liver, Analyt. Lett. 23, 57-65.
15. Minamide, Y., Horie, T., and Awazu, S. (1992) Fluorospectroscopic Analysis of the Fluorescent Substances in Peroxidized Microsomes of Rat Liver, Lipids 27, 354-359.
16. Parker, C. A. (1968) Photoluminescence of Solutions, Elsevier, Amsterdam.
17. Demas, J.N., and Crosby, G.A. (1971) The Measurement of Photoluminescence Quantum Yields: A Review, Journal of Physical Chemistry. 75, 991-1024.
18. Melhuish, W.H. (1961) Quantum Efficiencies of Fluorescence of Organic Substances: Effect of Solvent and Concentration of the Fluorescent Solute, J. Phys. Chem. 65, 229-235.
19. Riddick, J.A., Bunger, W.B., and Sakano, T.K. (1986) Organic Solvents (Techniques of Chemistry, Vol. II), Wiley, New York.
20. Lakowicz, J.R. (1983) Principles of Fluorescence Spectroscopy, Plenum, New York.
21. Lakowicz, J.R., Cherek, H., and Baiter, A. (1981) Correction of Timing Errors in Photomultiplier Tubes Used in Phase-Modulation Fluorometry, J. Biochem. Biophys. Methods 5, 131-146.
22. Lakowicz, J.R., Laczko, G., Cherek, H., Gratton, E., and Limkeman, M. (1984) Analysis of Fluorescence Decay Kinetics from Variable-Frequency Phase Shift and Modulation Data, Biophys. J. 46, 463-477.
23. Lakowicz, J., and Cherek, H. (1981) Phase-Sensitive Fluorescence Spectroscopy: A New Method to Resolve Fluorescence Lifetimes or Emission Spectra of Components in a Mixture of Fluorophores, J. Biochem. Biophys. Meth. 5, 19-35.
24. Leahy, D.E. (1986) Intrinsic Molecular Volume as a Measure of the Cavity Term in Linear Solvation Energy Relationships: Octanol-Water Partition Coefficients and Aqueous Solubilities, J. Pharm. Sci. 75, 629-636.
25. Kikugawa, K., Iwata, A., and Beppu, M. (1988) Formation of Cross-Links and Fluorescence in Polylysine, Soluble Proteins and Membrane Proteins by Reaction with 1-Butanal, Chem. Pharm. Bull. 36, 685-692.
26. Espenson, J.H. (1981) Chemical Kinetics and Reaction Mechanisms, McGraw-Hill, New York.
27. 9, Aidehydes in Water by Gas Chromatography, J. Gas Chromatogr. 6, 518-519.
28. Pliška, V., Schmidt, M., and Fauchère, J.-L. (1981) Partition Co-efficients of Amino Acids and Hydrophobic Parameters π of Their Side-Chains as Measured by Thin-Layer Chromatography, J. Chromatogr. 216, 79-92.
29. Martell, A.E., and Smith, R.M. (1974) Critical Stability Constants, Vol. I: Amino Acida, Plenum, New York.
30. Gilbert, A., and Baggott, J. (1991) Essentials of Molecular Photochemistry, Blackwell, Oxford.
31. Kossanyi, J., Daccord, G., Sabbah, S., Furth, B., Chaquin, P., André, J.C., and Bouchy, M. (1980) Photochemistry in Solution. Self-Quenching and Quenching by Dienes of Aldehyde Singlet States, Nouv. J. Chim. 4, 337-344.
32. Kikugawa, K., and Sawamura, A. (1987) Formation of Fluorescent Substances in Reaction of Aliphatic Aldehydes and Methylamine, J. Am. Oil Chem. Soc. 64, 1156-1162.
33. Kikugawa, K., Takayanagi, K., and Watanabe, S. (1985) Polylysines Modified with Malonaldehyde, Hydroperoxylinoleic Acid and Monofunctional Aldehydes, Chem. Pharm. Bull. 33, 5437-5444.
34. Beppu, M., Murakami, K., and Kikugawa, K. (1986) Fluorescent and Cross-Linked Proteins of Human Erythrocyte Ghosts Formed by Reaction with Hydroperoxylinoleic Acid, Malonaldehyde and Monofunctional Aldehydes, Chem. Pharm. Bull. 34, 781-788.
35. Yamaki, S., Kato, T., and Kikugawa, K. (1992) Characteristics of Fluorescence Formed by the Reaction of Proteins with Unsaturated Aldehydes, Possible Degradation Products of Lipid Radicals, Chem. Pharm. Bull. 40, 2138-2142.
36. Suyama, K., and Adachi, S. (1979) Reaction of Alkanals and Amino Acids or Primary Amines. Synthesis of 1,2,3,5- and 1,3,4,5-Substituted Quaternary Pyridinium Salts, J. Org. Chem. 44, 1417-1420.
37. Kikugawa, K., Kato, T., and Iwata, A. (1989) A Tetrameric Dialdehyde Formed in the Reaction of Butyraldehyde and Benzylamine: A Possible Intermediary Component for Protein Cross-Linking Induced by Lipid Oxidation, Lipids 24, 962-968.
38. Fukuzawa, K., Kishikawa, K., Tokumura, A., Tsukatani, H., and Shibuya, M. (1985) Fluorescent Pigments by Covalent Binding of Lipid Peroxidation By-Products to Protein and Amino Acids, Lipids 20, 854-861.
39. Esterbauer, H., Zollner, H., and Scholz, N. (1975) Reaction of Glutathione with Conjugated Carbonyls, Z. Naturforsch. 30C, 466-473.