Simple Detection Method of Biogenic Amines in Decomposed Fish by Intramolecular Excimer Fluorescence

DOI: 10.4236/fns.2012.37135   PDF   HTML   XML   5,964 Downloads   10,006 Views   Citations

Abstract

Biogenic amines are known to have various biological functions such as not only neurotransmitter and cell proliferation but also food poisoning. Bacterially-decomposed amines such as histamine, agmatine, putrescine, cadaverine, spermidine and spermine cause allergic symptoms. We developed simple method for measurement of polyamine as indicator of food decomposition with a fluorometer by using 4-(1-Pyrene)butyric acid N-hydroxysuccinimide ester (PSE). PSE reacts with primary and secondary amino moieties of polyamines and produces the intramolecular excimer fluorescence. Excimer fluorescence with broad peak at around 470 nm was clearly detected in linear type biogenic amines such as putrescine, cadaverine, spermidine and spermine at 10 mM. However neither histamine nor trimethylamine altered the fluorescence. Decomposed sardine and mackerel by improper storage showed stronger intensity than fresh ones. Comparing with OPA-method, PSE method was useful for screening biogenic amines present in food, esp. fish since the analysis was simple after one-step purification procedure. An inexpensive system which can rapidly detect biogenic amines from food is necessary in a medium and small-sized food business. The technique using excimer has potential to realize the high through-put screening system for evaluation of food freshness and is expected to bring the public interests such as food security and safety of consumer.

Share and Cite:

H. Nishikawa, T. Tabata and S. Kitani, "Simple Detection Method of Biogenic Amines in Decomposed Fish by Intramolecular Excimer Fluorescence," Food and Nutrition Sciences, Vol. 3 No. 7, 2012, pp. 1020-1026. doi: 10.4236/fns.2012.37135.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] K. Hyland, “Neurochemistry and Defects of Biogenic Amine Neurotransmitter Metabolism,” Journal of Inherited Metabolic Disease, Vol. 22, No. 4, 1999, pp. 353-363. doi:10.1023/A:1005587719505
[2] T. H. Jover, M. I. Pulido, M. T. V. Nogues, A. M. Font and M. C. V. Carou, “Biogenic Amine and Polyamine Contents in Meat and Meat Products,” Journal of Agricultural and Food Chemistry, Vol. 45, No. 6, 1997, pp. 2098-2102. doi:10.1021/jf960790p
[3] P. Kalac, “Biogenic Amine and Polyamine Contents in Meat and Meat Products,” Journal of Applied Biomedicine, Vol. 7, No. 2, 2009, pp. 65-74.
[4] M. K. Kim, J. H. Mah and H. J. Hwang, “Biogenic Amine Formation and Bacterial Contribution in Fish, Squid and Shellfish,” Food Chemistry, Vol. 116, No. 1, 2009, pp. 87-95. doi:10.1016/j.foodchem.2009.02.010
[5] I. A. Bulushi, S. Poole, H. Deeth and G. Dykes, “Biogenic Amines in Fish: Roles in Intoxication, Spoilage, and Nitrosamine Formation: A Review,” Critical Reviews in Food Science and Nutrition, Vol. 49, No, 4, 2009, pp. 369-377. doi:10.1080/10408390802067514
[6] S. Standara, M. Vesela and M. Drdak, “Determination of Biogenic Amines in Cheese by Ion Exchange Chromatography,” Nahrung-Food, Vol. 44, No. 1, 2000, pp. 28-31. doi:10.1002/(SICI)1521-3803(20000101)44:1<28::AID-FOOD28>3.0.CO;2-I
[7] J. M. Landete, B. de las Rivas, A. Marcobal and R. Munoz, “Molecular Methods for the Detection of Biogenic Amine-producing Bacteria on Foods,” International Journal of Food Microbiology, Vol. 117, No. 3, 2007, pp. 258-269. doi:10.1016/j.ijfoodmicro.2007.05.001
[8] J. M. Hungerford, “Scombroid Poisoning: A Review,” Toxicon, Vol. 56, No. 2, 2010, pp. 231-243. doi:10.1016/j.toxicon.2010.02.006
[9] L. Prester, T. Orct, L. Macan, J. Vukusic and D. Kipcic, “Determination of Biogenic Amines and Endotoxin in Squid, Musky Octopus, Norway Lobster, and Mussel Stored at Room Temperature,” Archives of Industrial Hygiene and Toxicology, Vol. 61, No. 4, 2010, pp. 389-397. doi:10.2478/10004-1254-61-2010-2049
[10] N. Erkan, “Changes in Quality Characteristics during Cold Storage of Shucked Mussels (Mytilus galloprovincialis) and Selected Chemical Decomposition Indicators,” Journal of the Science of Food and Agriculture, Vol. 85, No. 15, 2005, pp. 2625-2630. doi:10.1002/jsfa.2331
[11] R. A. Benner, W. F. Staruszkiewicz and W. S. Otwell, “Putrescine, Cadaverine, and Indole Production by Bacteria Isolated from Wild and Aquacultured Penaeid Shrimp Stored at 0, 12, 24, and 36 Degrees C,” Journal of Food Protection, Vol. 67, No. 1, 2004, pp. 124-133.
[12] V. E. Gonzaga, A. G. Lescano, A. A. Huaman, G. SalmonMulanovich and D. L. Blazes, “Histamine Levels in Fish from Markets in Lima, Peru,” Journal of Food Protection, Vol. 72, No. 5, 2009, pp. 1112-1115.
[13] S. L. Taylor, J. E. Stratton and J. A. Nordlee, “Histamine Poisoning (Scombroid Fish Poisoning): An Allergy-Like Intoxication,” Journal of Toxicology Clinical Toxicology, Vol. 27, No. 4-5, 1989, pp. 225-240. doi:10.3109/15563658908994420
[14] S. L. Taylor, “Histamine Food Poisoning: Toxicology and Clinical Aspects,” Critical reviews in Toxicology, Vol. 17, No. 2, 1986, pp. 91-128. doi:10.3109/10408448609023767
[15] F. E. Russell and Z. Mareti?, “Scombroid Poisoning: Mini-Review with Case Histories,” Toxicon, Vol. 24, No. 10, 1986, pp. 967-973. doi:10.1016/0041-0101(86)90002-4
[16] T. Toyo’oka, “Separation Assay of Histamine and Its Metabolites in Biological Specimens,” Biomedical Chromatography, Vol. 22, No. 9, 2008, pp. 919-930. doi:10.1002/bmc.1027
[17] M. Miki, T. Ishikawa and H. Okayama, “An Outbreak of Histamine Poisoning after Ingestion of the Ground Saury Paste in Eight Patients Taking Isoniazid in Tuberculous Ward,” Internal Medicine, Vol. 44, No. 11, 2005, pp. 1133-1136. doi:10.2169/internalmedicine.44.1133
[18] L. F. Bjeldanes, D. E. Schutz and M. M. Morris, “On the Aetiology of Scombroid Poisoning: Cadaverine Potentiation of Histamine Toxicity in the Guinea-Pig,” Food and Cosmetics Toxicology, Vol. 16, No.2, 1978, pp. 157-159. doi:10.1016/S0015-6264(78)80196-5
[19] J. L. Mongar, “Effect of Chain Length of Aliphatic Amines on Histamine Potentiation and Release,” British Journal of Pharmacology and Chemotherapy, Vol. 12, No. 2, 1957, pp. 140-148.
[20] D. E. Lyons, J. T. Beery, S. A. Lyons and S. L. Taylor, “Cadaverine and Aminoguanidine Potentiate the Uptake of Histamine in Vitro in Perfused Intestinal Segments of Rats,” Toxicology and Applied Pharmacology, Vol, 70, No. 3, 1983, pp. 445-458. doi:10.1016/0041-008X(83)90162-X
[21] P. Ijomah, M. N. Clifford, R. Walker, J. Wright, R. Hardy and C. K. Murray, “The Importance of Endogenous Histamine Relative to Dietary Histamine in the Aetiology of Scombrotoxicosis,” Food Additives and Contaminants, Vol. 8, No. 4, 1991, pp. 531-542. doi:10.1080/02652039109374005
[22] M. Kurosawa, D. Uno and S. Kobayashi, “Naturally Occurring Aliphatic Polyamines-induced Histamine Release from Rat Peritoneal Mast Cells,” Allergy, Vol. 46, No. 5, 1991, pp. 349-354. doi:10.1111%2Fj.1398-9995.1991.tb00597.x
[23] M. Mousli, J. L. Bueb, B. Rouot, Y. Landry and C. Bronner, “G-proteins as Targets for Non-Immunological Histamine Releasers,” Inflammation Research, Vol. 33, No. 1-2, 1991, pp. 81-83. doi:10.1007%2FBF01993132
[24] G. García-Faroldi, C. E. Rodríguez, J. L. Urdiales, J. M. Pérez-Pomares, J. C. Dávila, G. Pejler, F. Sánchez-Jiménez and I. Fajardo, “Polyamines Are Present in Mast Cell Secretory Granules and are Important for Granule Homeostasis,” PLoS ONE, Vol. 5, No. 11, 2010, p. e.15071. doi:10.1371%2Fjournal.pone.0015071
[25] J. Lapa-Guimar?es and J. Pickova, “New Solvent Systems for Thin-layer Chromatographic Determination of Nine Biogenic Amines in Fish and Squid,” Journal of Chromatography A, Vol. 1045, No. 1-2, 2004, pp. 223-232. doi:10.1016%2Fj.chroma.2004.06.014
[26] R. Romero, M. Sánchez-Vi?as, D. Gázquez and M. G. Bagur, “Characterization of Selected Spanish Table Wine Samples according to Their Biogenic Amine Content from Liquid Chromatographic Determination,” Journal of Agricultural and Food Chemistry, Vol. 50, No. 16, 2002, pp. 4713-4717. doi:10.1021%2Fjf025514r
[27] R. P. Siraganian, “An Automated Continuous-flow System for the Extraction and Fluorometric Analysis of Histamine,” Analytical Biochemistry, Vol. 57, No. 2, 1974, pp. 383-394. doi:10.1016%2F0003-2697%2874%2990093-1
[28] A. Kovács, L. Simon-Sarkadi and K. Ganzler, “Determination of Biogenic Amines by Capillary Electrophoresis,” Journal of Chromatography A, Vol. 836, No. 2, 1999, pp. 305-313. doi:10.1016%2FS0021-9673%2898%2900912-1
[29] T. Yoshitake, F. Ichinose, H. Yoshida, K. Todoroki, J. Kehr, O. Inoue, H. Nohta and M. Yamaguchi, “A Sensitive and Selective Determination Method of Histamine by HPLC with Intramolecular Excimer-Forming Derivatization and Fluorescence Detection,” Biomedical Chromatography, Vol. 17, No. 8, 2003, pp. 509-516. foi:10.1002%2Fbmc.264
[30] H. Nohta, H. Satozono, K. Koiso, H. Yoshida, J. Ishida and M. Yamaguchi, “Highly Selective Fluorometric Determination of Polyamines Based on Intramolecular Excimer-forming Derivatization with a Pyrene-labeling Reagent,” Analytical Chemistry, Vol. 72, No. 17, 2000, pp. 4199-4204. doi:10.1021%2Fac0002588
[31] H. Yoshida, H. Harada, Y. Nakano, H. Nohta, J. Ishida and M. Yamaguchi, “Liquid Chromatographic Determination of Polyamines in Human Urine Based on Intramolecular Excimer-forming Fluorescence Derivatization Using 4-(1-Pyrene)butanoyl Chloride,” Biomedical Chromatography, Vol. 18, No. 9, 2004, pp. 687-693. doi:10.1002%2Fbmc.377
[32] H. S. M. Rupp and C. R. Anderson, “Determination of Putrescine and Cadaverine in Seafood (Finfish and Shellfish) by Liquid Chromatography Using Pyrene Excimer Fluorescence,” Journal of Chromatography A, Vol. 1094, No. 1-2, 2005, pp. 60-69. doi:10.1016%2Fj.chroma.2005.07.088
[33] T. Yoshitake, M. Yamaguchi, H. Nohta, F. Ichinose, H. Yoshida, S. Yoshitake, K. Fuxe and J. Kehr, “Determination of Histamine in Microdialysis Samples from Rat Brain by Microbore Column Liquid Chromatography following Intramolecular Excimer-Forming Derivatization with Pyrene-labeling Reagent,” Journal of Neuroscience Method, Vol. 127, No. 1, 2003, pp. 11-17. doi:10.1016%2FS0165-0270%2803%2900097-9

  
comments powered by Disqus

Copyright © 2020 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.