Abstract
Background: Biogenic Amines (BAs) are biologically active nitrogenous organic compounds of low molecular weight, which are frequently found in a wide variety of foods, beverages and herbs due to their toxic potential in humans. Male Silkworm Moth (MSM), a Traditional Chinese Medicine (TCM), has been exploited and utilized as nutritious liquor based on its traditional effects in the Chinese community.
Objective: The objective of this study was to develop an HPLC with Dns-Cl derivatization method for characterizing overall BAs in MSM and providing data for further evaluating its activities and safety profiles.
Methods: The method has acceptable sensitivity, precision, accuracy, selectivity and recovery, and was successfully applied to the determination of the BAs contents in MSM for the first time.
Results: In the analysis of 10 batches of MSM samples, serotonin and dopamine were not found in detectable concentrations in any samples, and the most abundant amine found was putrescine. The mean values of tryptamine, phenylethylamine, putrescine, cadaverine, histamine, tyramine, spermidine, and spermine determined in the samples were found to be 34.7 mg/ kg, 16.1 mg/ kg, 218.3 mg/ kg, 37.9 mg/ kg, 12.1 mg/ kg, 18.2 mg/ kg, 4.5mg/ kg, and 0.9 mg/ kg, respectively.
Conclusion: The contents of BAs in 10 batches of MSM were below the maximum recommended limits, and MSM can be used safely.
Keywords: Biogenic amines, Male silkworm moth, Derivatization, HPLC, Dns-Cl, safety profiles.
Graphical Abstract
[1]
Santos, MHS. Int. J. Food Microbiol., 1996, 29, 213-231.
[http://dx.doi.org/10.1016/0168-1605(95)00032-1] [PMID: 8796424]
[http://dx.doi.org/10.1016/0168-1605(95)00032-1] [PMID: 8796424]
[2]
Tassoni, A.; Germanà, M.A.; Bagni, N. Free and conjugated polyamine content in Citrus sinensis Osbeck, cultivar Brasilino N.L. 92, a Navel orange, at different maturation stages. Food Chem., 2004, 87, 537-541.
[http://dx.doi.org/10.1016/j.foodchem.2004.01.001]
[http://dx.doi.org/10.1016/j.foodchem.2004.01.001]
[3]
Kalač, P.; Krausová, P. A review of dietary polyamines: Formation, implications for growth and health and occurrence in foods. Food Chem., 2005, 90, 219-230.
[http://dx.doi.org/10.1016/j.foodchem.2004.03.044]
[http://dx.doi.org/10.1016/j.foodchem.2004.03.044]
[4]
Önal, A. A review: Current analytical methods for the determination of biogenic amines in foods. Food Chem., 2007, 103, 1475-1486.
[http://dx.doi.org/10.1016/j.foodchem.2006.08.028]
[http://dx.doi.org/10.1016/j.foodchem.2006.08.028]
[5]
Yen, G.C.; Kao, H.H. Antioxidative Effect of Biogenic Amine on the Peroxidation of Linoleic Acid. Biosci. Biotechnol. Biochem., 1993, 57(1), 115-116.
[http://dx.doi.org/10.1271/bbb.57.115] [PMID: 27316882]
[http://dx.doi.org/10.1271/bbb.57.115] [PMID: 27316882]
[6]
Eisenberg, T.; Knauer, H.; Schauer, A.; Büttner, S.; Ruckenstuhl, C.; Carmona-Gutierrez, D. Induction of autophagy by spermidine promotes longevity. Nat. Cell Biol., 2009, 11, 1305-1314.
[http://dx.doi.org/10.1038/ncb1975]
[http://dx.doi.org/10.1038/ncb1975]
[7]
Shalaby, A.R. Significance of biogenic amines to food safety and human health. Food Res. Int., 1996, 29, 675-690.
[http://dx.doi.org/10.1016/S0963-9969(96)00066-X]
[http://dx.doi.org/10.1016/S0963-9969(96)00066-X]
[8]
Hernández-Borges, J.; D’Orazio, G.; Aturki, Z.; Fanali, S. Nano-liquid chromatography analysis of dansylated biogenic amines in wines. J. Chromatogr. A, 2007, 1147(2), 192-199.
[http://dx.doi.org/10.1016/j.chroma.2007.02.072] [PMID: 17353021]
[http://dx.doi.org/10.1016/j.chroma.2007.02.072] [PMID: 17353021]
[9]
Cai, Y.; Sun, Z.; Chen, G.; Liu, X.; You, J.; Zhang, C. Rapid analysis of biogenic amines from rice wine with isotope-coded derivatization followed by high performance liquid chromatography-tandem mass spectrometry. Food Chem., 2016, 192, 388-394.
[http://dx.doi.org/10.1016/j.foodchem.2015.07.024] [PMID: 26304364]
[http://dx.doi.org/10.1016/j.foodchem.2015.07.024] [PMID: 26304364]
[10]
Nairn, L.M.; Lindsay, G.S.; Woster, P.M.; Wallace, H.M. Cytotoxicity of novel unsymmetrically substituted inhibitors of polyamine biosynthesis in human cancer cells. J. Cell. Physiol., 2000, 182(2), 209-213.
[http://dx.doi.org/10.1002/(SICI)1097-4652(200002)182:2<209:AID-JCP9>3.0.CO;2-8] [PMID: 10623884]
[http://dx.doi.org/10.1002/(SICI)1097-4652(200002)182:2<209:AID-JCP9>3.0.CO;2-8] [PMID: 10623884]
[11]
Gomez, F.J.V.; Monasterio, R.P.; Vargas, V.C.S.; Silva, M.F. Analytical characterization of wine and its precursors by capillary electrophoresis. Electrophoresis, 2012, 33(15), 2240-2252.
[http://dx.doi.org/10.1002/elps.201100595] [PMID: 22887148]
[http://dx.doi.org/10.1002/elps.201100595] [PMID: 22887148]
[12]
Romano, A.; Klebanowski, H.; La Guerche, S.; Beneduce, L.; Spano, G.; Murat, M.L.; Lucas, P. Determination of biogenic amines in wine by thin-layer chromatography/densitometry. Food Chem., 2012, 135(3), 1392-1396.
[http://dx.doi.org/10.1016/j.foodchem.2012.06.022] [PMID: 22953871]
[http://dx.doi.org/10.1016/j.foodchem.2012.06.022] [PMID: 22953871]
[13]
Almeida, C.; Fernandes, J.O.; Cunha, S.C. A novel dispersive liquid–liquid microextraction (DLLME) gas chromatography mass spectrometry (GC–MS) method for the determination of eighteen biogenic amines in beer. Food Control, 2012, 25, 380-388.
[http://dx.doi.org/10.1016/j.foodcont.2011.10.052]
[http://dx.doi.org/10.1016/j.foodcont.2011.10.052]
[14]
Cinquina, A.L.; Calì, A.; Longo, F.; De Santis, L.; Severoni, A.; Abballe, F. Determination of biogenic amines in fish tissues by ion-exchange chromatography with conductivity detection. J. Chromatogr. A, 2004, 1032(1-2), 73-77.
[http://dx.doi.org/10.1016/j.chroma.2004.01.013] [PMID: 15065779]
[http://dx.doi.org/10.1016/j.chroma.2004.01.013] [PMID: 15065779]
[15]
Alonso-Lomillo, M.A.; Domínguez-Renedo, O.; Matos, P.; Arcos-Martínez, M.J. Disposable biosensors for determination of biogenic amines. Anal. Chim. Acta, 2010, 665(1), 26-31.
[http://dx.doi.org/10.1016/j.aca.2010.03.012] [PMID: 20381686]
[http://dx.doi.org/10.1016/j.aca.2010.03.012] [PMID: 20381686]
[16]
de Figueiredo, T.C.; de Assis, D.C.; Menezes, L.D.; da Silva, G.R.; Lanza, I.P.; Heneine, L.G.; Cançado, Sde.V. HPLC-UV method validation for the identification and quantification of bioactive amines in commercial eggs. Talanta, 2015, 142, 240-245.
[http://dx.doi.org/10.1016/j.talanta.2015.04.056] [PMID: 26003718]
[http://dx.doi.org/10.1016/j.talanta.2015.04.056] [PMID: 26003718]
[17]
César, A. Lázaro; Carlos, A.; Conte-Júnior, Fernanda L.; Conte-Júnior, Fernanda L. Cunha. Eliane T. Mársico. Sérgio B. Mano. Robson M. Franco. Validation of an HPLC methodology for the identification and quantification of biogenic amines in chicken meat. Food Anal. Methods, 2013, 6, 1024-1032.
[http://dx.doi.org/10.1007/s12161-013-9565-0]
[http://dx.doi.org/10.1007/s12161-013-9565-0]
[18]
Yoon, H.; Park, J.H.; Choi, A.; Hwang, H.J.; Mah, J.H. Validation of an HPLC analytical method for determination of biogenic amines in agricultural products and monitoring of biogenic amines in Korean fermented agricultural products. Toxicol. Res., 2015, 31(3), 299-305.
[http://dx.doi.org/10.5487/TR.2015.31.3.299] [PMID: 26483889]
[http://dx.doi.org/10.5487/TR.2015.31.3.299] [PMID: 26483889]
[19]
Wang, X.; Liang, Y.; Wang, Y.; Fan, M.; Sun, Y.; Liu, J.; Zhang, N. Simultaneous determination of 10 kinds of biogenic amines in rat plasma using high-performance liquid chromatography coupled with fluorescence detection. Biomed. Chromatogr., 2018, 32(6)e4211
[http://dx.doi.org/10.1002/bmc.4211] [PMID: 29446845]
[http://dx.doi.org/10.1002/bmc.4211] [PMID: 29446845]
[20]
Busto, O.; Miracle, M.; Guasch, J.; Borrull, F. Determination of biogenic amines in wines by high-performance liquid chromatography with on-column fluorescence derivatization. J. Chromatogr. A, 1997, 757, 311-318.
[http://dx.doi.org/10.1016/S0021-9673(96)00693-0]
[http://dx.doi.org/10.1016/S0021-9673(96)00693-0]
[21]
Proestos, C.; Loukatos, P.; Komaitis, M. Determination of biogenic amines in wines by HPLC with precolumn dansylation and fluorimetric detection. Food Chem., 2008, 106, 1218-1224.
[http://dx.doi.org/10.1016/j.foodchem.2007.06.048]
[http://dx.doi.org/10.1016/j.foodchem.2007.06.048]
[22]
Anlı, R.E.; Vural, N.; Yılmaz, S.; Vural, Ỳ.H. The determination of biogenic amines in Turkish red wines. J. Food Compos. Anal., 2004, 17, 53-62.
[http://dx.doi.org/10.1016/S0889-1575(03)00104-2]
[http://dx.doi.org/10.1016/S0889-1575(03)00104-2]
[23]
Jiang, K.; Dong, H.; Zhang, T. Research progress on development and utilization of male silkworm moth. Food Nutrition China, 2015, 21, 72-77.
[24]
Lin, X; Luo, J Nutritional value and technology research of male silkworm moth wine. Light Industy Sci. Technol., 2015, 4, 20, 21.
[25]
Lv, Y.; Cheng, M.; Chen, P. Nutritional components and content detemination in male Pupae of Chuanzuo 1. Bulletin of Sericulture., 2017, 48, 35-43.
[26]
Redruello, B.; Ladero, V.; Cuesta, I.; Álvarez-Buylla, J.R.; Martín, M.C.; Fernández, M.; Alvarez, M.A. A fast, reliable, ultra high performance liquid chromatography method for the simultaneous determination of amino acids, biogenic amines and ammonium ions in cheese, using diethyl ethoxymethylenemalonate as a derivatising agent. Food Chem., 2013, 139(1-4), 1029-1035.
[http://dx.doi.org/10.1016/j.foodchem.2013.01.071] [PMID: 23561206]
[http://dx.doi.org/10.1016/j.foodchem.2013.01.071] [PMID: 23561206]
[27]
Wojnowski, W.; Namieśnik, J.; Płotka-Wasylka, J. Dispersive liquid-liquid microextraction combined with gas chromatography-mass spectrometry for in situ determination of biogenic amines in meats: Estimation of meat’s freshness. Microchem. J., 2019, 145, 130-138.
[http://dx.doi.org/10.1016/j.microc.2018.10.034]
[http://dx.doi.org/10.1016/j.microc.2018.10.034]
[28]
Pineda, A.; Carrasco, J.; Peña-Farfal, C. Preliminary evaluation of biogenic amines content in Chilean young varietal wines by HPLC. Food Control, 2012, 23, 251-257.
[http://dx.doi.org/10.1016/j.foodcont.2011.07.025]
[http://dx.doi.org/10.1016/j.foodcont.2011.07.025]
[29]
Becker, K.; Southwick, K.; Reardon, J.; Berg, R.; MacCormack, J.N. Histamine poisoning associated with eating tuna burgers. JAMA, 2001, 285(10), 1327-1330.
[http://dx.doi.org/10.1001/jama.285.10.1327] [PMID: 11255388]
[http://dx.doi.org/10.1001/jama.285.10.1327] [PMID: 11255388]
[30]
Joosten, H.M.L.J. The biogenic amine contents of Dutch cheese and their toxicological significance. Neth. Milk Dairy J., 1988, 42, 25-42.
[31]
Tang, T.; Qian, K.; Shi, T.; Wang, F.; Li, J.; Cao, Y. Monitoring the contents of biogenic amines in sufu by HPLC with SPE and pre-column derivatization. Food Control, 2011, 22, 1203-1208.
[http://dx.doi.org/10.1016/j.foodcont.2011.01.018]
[http://dx.doi.org/10.1016/j.foodcont.2011.01.018]
[32]
Halász, A.; Baráth, Á.; Simon-Sarkadi, L.; Holzapfel, W. Biogenic amines and their production by microorganisms in food. Trends Food Sci. Technol., 1994, 5, 42-49.
[http://dx.doi.org/10.1016/0924-2244(94)90070-1]
[http://dx.doi.org/10.1016/0924-2244(94)90070-1]
[33]
Valsamaki, K.; Michaelidou, A.; Polychroniadou, A. Biogenic amine production in Feta cheese. Food Chem., 2000, 71, 259-266.
[http://dx.doi.org/10.1016/S0308-8146(00)00168-0]
[http://dx.doi.org/10.1016/S0308-8146(00)00168-0]
Article Metrics
12