HPLC method for analysis of free amino acids in fish using o- phthaldialdehyde precolumn derivatization

Journal of Agricultural and Food Chemistry

Volumn 47, Issue 12, 1999, Pages 5100-5107

  Antoine, F R ^a   Wei, C I ^a,b   Littell, R C ^a   Marshall, M R ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b AUBURN UNIVERSITY   (United States)

Author keywords

Fish; Free amino acids; HPLC method; o phthaldialdehyde (OPA); Precolumn derivatization

Indexed keywords

AMINO ACID; BIOGENIC AMINE; CADAVERINE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HISTAMINE; HISTIDINE; LYSINE; ORNITHINE; PHTHALALDEHYDE; PUTRESCINE;

AMINO ACID ANALYSIS; ANIMAL; ARTICLE; CHEMISTRY; DERIVATIZATION; FISH; FLOUNDER; FOOD PRESERVATION; FOOD SAFETY; FOOD STORAGE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; METABOLISM; NONHUMAN; PERCIFORMES; PH; SAMPLING; SPECIES DIFFERENCE; TUNA;

AMINO ACIDS; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FISHES; FLOUNDER; FOOD PRESERVATION; HISTIDINE; HUMANS; INDICATORS AND REAGENTS; LYSINE; O-PHTHALALDEHYDE; ORNITHINE; PERCIFORMES; TUNA;

ANIMALIA; PERCIFORMES; PLEURONECTOIDEI; SCOMBRIDAE GEN. SP.; THUNNUS OBESUS;

EID: 0033396532     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf990032+     Document Type: Article

References (42)

1. Abe, H. Distribution of free L-histidine and its related compounds in marine fishes. Bull. Jpn. Soc. Sci. Fish. 1983, 49, 1683-1687.
2. Arnold, S. H.; Brown, W. D. Histamine (?) toxicity from fish products. Adv. Food Res. 1978, 24, 113-154.
3. Belitz, H. D.; Grosch, W. Amino acids, peptides, proteins. In Food Chemistry; Springer-Verlag: Berlin, Germany, 1987; pp 7-32.
4. Chen, R. F.; Scott, C.; Trepman, E. Fluorescence properties of o-phthaldialdehyde derivatives of amino acids. Biochim. Biophys. Acta 1979, 576, 440-455.
5. Cronin, J. R.; Pizzarello, S.; Gandy, W. E. Amino acid analysis with o-phthalaldehyde detection: effects of reaction temperature and thiol on fluorescence yields. Anal. Biochem. 1979, 93, 174-179.
6. Damodaran, S. Amino acids, peptides, and proteins. In Food Chemistry, 3rd ed.; Fennema, O. R., Ed.; Dekker: New York, 1996; pp 321-429.
7. Finne, G. Nonprotein nitrogen compounds in fish and shell fish. In Advances in Seafood Biochemistry; Flick, G., Martin, R. E., Eds.; Technomic Publishing: Lancaster, PA, 1992; pp 393-401.
8. Fletcher, G. C.; Summers, G.; Winchester, R. V.; Wong, R. J. Histamine and histidine in New Zealand marine fish and shellfish species, particularly kahawai (Arripis trutta). J. Aquat. Food Prod. Technol. 1995, 4 (2), 53-74.
9. Hibiki, S.; Simidu, W. Studies on the putrefaction of aquatic products-27: Inhibition of histamine formation in spoiling of cooked fish and histidine content in various fishes. Bull. Jpn. Soc. Sci. Fish. 1959, 24, 916-919.
10. Hill, D.; Burnworth, L.; Skea, W.; Pfeifer, R. Quantitative HPLC analysis of plasma amino acids as orthophthaldialdehyde/ethanethiol derivatives. J. Liq. Chromatogr. 1982, 5 (12), 2369-2393.
11. Hodgin, J. C. The separation of pre-column o-phthalaldehyde derivatized amino acids by high performance liquid chromatography. J. Liq. Chromatogr. 1979, 2 (7), 1047-1059.
12. Ito, K. Amino acid composition of the muscle extracts of aquatic animals. Bull. Jpn. Soc. Sci. Fish. 1957, 23, 497-500.
13. Jones, B. N.; Paabo, S.; Stein, S. Amino acid analysis and enzymatic sequence determination of peptides by an improved o-phthaldialdehyde precolumn labeling procedure. J. Liq. Chromatogr. 1881, 4, 565-586.
14. Joseph, M. H.; Marsden, C. A. Amino acids and small peptides. In HPLC of Small Molecules: A Practical Approach; Lim, C. K., Ed.; IRL: Oxford, U.K., 1986; pp 13-28.
15. Kirk, J. R. Nutritional changes upon processing. In Food Science and Nutrition: Current Issues and Answers; Clydesale, F., Ed.; Prentice-Hall: Englewood Cliffs, NJ, 1979; pp 62-92.
16. Kirschbaum, J.; Luckas, B.; Beinert, W. D. HPLC analysis of biogenic amines and amino acids in food after automatic precolumn derivatization with 9-fluorenylmethyl chloroformate. Am. Lab. 1994, 10, 28C-28H.
17. Konosu, S.; Watanabe, K.; Shimizu, T. Distribution of nitrogenous constituents in the muscle extracts of eight species of fish. Bull. Jpn. Soc. Sci. Fish. 1974, 40, 909-915.
18. Kucera, P.; Umagat, H. Design of a post-column fluorescence derivatization system for use with microbore columns. J. Chromatogr. 1983, 255, 563-579.
19. Lambert, M. A. S.; Moss, C. W. Use of gas chromatography for detecting ornithine and lysine decarboxylase activity in bacteria. Appl. Microbiol. 1973, 26, 517-520.
20. Lee, K. S.; Drescher, D. G. Minireview: Fluorometric amino acid analysis with o-phthaldialdehyde (OPA). Int. J. Biochem. 1978, 9, 457-467.
21. Lindroth, P.; Mopper, K. High performance liquid chromatographic determination of subpicomole amounts of amino acids by pre-column fluorescence derivatization with o-phthaldialdehyde, Anal. Chem. 1979, 51, 1667-1674.
22. Lukton, A.; Olcott, H. S. Content of free imidazole compounds in the muscle tissue of aquatic animals. Food Res. 1958, 23, 611-618.
23. Luten, J. B.; Bouquet, W.; Seuren, L. A. J.; Berggraf, M. M.; Riekwel-Booy, G.; Durand, P.; Etienne, M.; Gouyou, J. P.; Landrein, A.; Ritchie, A.; Leclerq, M.; Guinet, R. Biogenic amines in fishery products: standardization method within EC. Dev. Food Sci. 1992, 30, 427-439.
24. Mietz, J. L.; Karmas, E. Polyamine and histamine content of rock fish, salmon, lobster, and shrimp as an indicator of decomposition. J. Assoc. Off. Anal. Chem. 1978, 61 (1), 139-145.
25. Miles, C. J.; Leong G. Glyphosate herbicide analysis by liquid chromatography with post-column reaction detection: column comparison and application notes. LC-GC 1992, 10 (6), 452-458.
26. Mukundan, M. K.; James, M. A.; Radhakrishnan, A. G.; Antony, P. D. Red and white meat of tuna (Euthynnus affinis): Their biochemical role and nutritional quality. Fish. Technol. 1979, 16, 77-82.
27. Nakamura, H.; Tamura, Z. Fluorometric determination of thiols by liquid chromatography with postcolumn derivatization. Anal. Chem. 1981, 53, 2190-2193.
28. Roth, M. Fluorescence reaction for amino acids. Anal. Chem. 1971, 43 (7), 880-882.
29. Sakaguchi, M.; Kawai, A. The change in the composition of free amino acids in carp muscle with the growth of the fish. Mem. Res. Inst. Food Sci. Kyoto Univ. 1970, 31, 19-21.
30. Sakaguchi, M.; Murata, M.; Kawai, A. Changes in free amino acids and creatine contents in yellowtail (Seriola quinqueradiata) muscle during ice storage. J. Food Sci. 1982, 47, 1662-1666.
31. Sikorski, Z. E.; Kolakowska, A.; Burt, J. R. Postharvest biochemical and microbial changes. In Seafood: Resources, Nutritional Composition, and Preservation; Sikorski, Z. E., Ed.; CRC Press: Boca Raton, FL, 1990; pp 55-75.
32. Simons, S. S., Jr.; Johnson, D. F. Ethanethiol: a thiol conveying improved properties to the fluorescent product of o-phthalaldehyde and thiols with amines. Anal. Biochem, 1977, 82, 250-254.
33. Simons, S. S., Jr.; Johnson, D. F. Reaction of o-phthalaldehyde and thiols with primary amines: Formation of 1-alkyl (and aryl) thio-2-alkylisoindoles. J. Org. Chem. 1978, 43, 3 (14).
34. Snyder, L. R.; Kirkland, J. J.; Glajch, J. L. Practical HPLC Method Development, 2nd ed.; Wiley: New York, 1997; pp 7-20, 292-349, 643-684.
35. Stuart, J. D.; Hill, D. W. o-Phthaldialdehyde derivative of taurine. In Handbook of HPLC for the Separation of Amino Acids, Peptides, and Proteins; Hancock, W. S., Ed.; CRC Press: Boca Raton, FL, 1984; pp 313-323.
36. Stuart, J. D.; Wilson, T. D.; Hill, D. W.; Feng, S. Y. High performance liquid chromatographic separation and fluorescent measurement of taurine, and key amino acid. J. Liq. Chromatogr. 1979, 2 (6), 809-821.
37. Takagi, M.; Iida, A.; Murayama, H.; Soma, S. On the formation of histamine during loss of freshness and putrefaction of various marine products. Bull. Fac. Fish. Hokkaido Univ. 1969, 20, 227-234.
38. Taylor, S.; Sumner, S. Determination of histamine, putrescine, and cadaverine. In Seafood Quality Determination: Proceedings of an International Symposium; Kramer, D. E., Liston, J., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1988; pp 235-245.
39. Turnell, D. C.; Cooper, J. D. H. Rapid assay for amino acids in serum or urine by pre-column derivatization and reversed-phase liquid chromatography. Clin. Chem. 1982, 28 (3), 527-531.
40. Umagat, H.; Kucera, P.; Wen, L.-F. Total amino acid analysis using pre-column fluorescence derivatization. J. Chromatogr. 1982, 239, 463-474.
41. West, K. A.; Hulmes, J. D.; Crabb, J. W. Improving the art and practices of amino acid analysis. Presented at the Association of Biomolecular Resource Facilities International Symposium on Biomolecular Techniques; ABRF '96, San Francisco, CA, 1996.
42. Yoshinaga, D. H.; Frank, H. A. Histamine-producing bacteria in decomposing skipjack tuna (Katsuwonus pelamis). Appl. Environ. Microbiol. 1982, 44, 447-452.