Amino acids and biogenic amines

Together with proteins and peptides, amino acids constitute the main components of the nitrogenous fraction of musts and wines. They are also the most studied and best known nitrogenated components in wines. Free amino acids in musts are of paramount importance. They constitute a source of nitrogen for yeasts in alcoholic fermentation, for lactic acid bacteria in malolactic fermentation, and can also be a source of aromatic compounds (Kosir and Kidric, 2001). In certain cases, some amino acids 

Several minerals and trace elements are vital to the human organism and must be ingested with daily food in sufficient amounts. Wine can contribute not only minerals containing potassium, calcium, and magnesium but also numerous essential trace elements, such as chromium, cobalt, iron, fluorine, copper, selenium, and zinc, among others. The contents found in wine are very low ranging from mg L 1 to igL, sometimes even lower. 

In the past decades, the increased consumption of table grapes and wines has been encouraged by the amply demonstrated beneficial effects of these substances on human illness, such as cardiovascular diseases, brain degeneration, and certain carcinogenic diseases (Caillet et al., 2006 Cheng et al, 2007). 

FIGURE 7.12 Overview of the biosynthesis of the main polyphenols from the phenylalanine precursor (adapted from Naczk and Shahidi, 2004). 

These compounds have a strong influence on the quality and character of the wine and are therefore important not only for the wine characterization but also reflects the history of the wine producing process, including the grape variety, the yeast strain, the containers used for fermentation and storage, and the enological practices. Their nature and 

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Fourth, the salt concentration in cheese also influences the production of biogenic amines (Kebary et al., 1999 Joosten, 1988). Gouda cheese contains 3.5 mmol histamine per kg with a salt water ratio of 0.048, and 2.1 mmol histamine with a salt water ratio of 0.026 (Joosten, 1988). Each cheese has its own characteristic free amino acid and biogenic amine profiles, resulting from its specific degradation, interconversion, and synthesis (Polo et al., 1985). 

Pinho, O., Ferreira, I.M.P.L., Mendes, E., Oliveira, B.M. and Ferreira, M. (2001). Effect of temperature on evolution of free amino acid and biogenic amine contents during storage of Azeitao cheese. Food Chem., 75, 287. 

I Krause, A Bockhardt, H Neckermann, T Henle, H Klostermeyer. Simultaneous determination of amino acids and biogenic amines by reversed-phase high-performance liquid chromatography of the dabsyl derivatives. J Chromatogr A 715 67-79, 1995. 

The use of fiuorescamine for the analysis of primary amines has been discussed for amino acids and biogenic amines. The reaction of this compound with amphetamine analogues is similar. The spray procedure is identical to that described for primary amino acids (Section 4.2.1.1.3). The limit of detection is 100 ng for amphetamine [84]. 

Krause, I., Bockhardt, A., and Klostermeyer, H. (1997). Characterization of cheese ripening by free amino acids and biogenic amines and influence of bactofugation and heat-treatment of milk. Lait 77,101-108. 

Moreno-Arribas, M. V. and Polo, M. C. (2009). Amino acids and biogenic amines. In "Wine Chemistry and Biochemistry", (M. V. Moreno-Arribas and M. C. Polo, Eds), pp. 163-189. Springer, New York. 

Pereira, V., Pontes, M., Camara, J. S., and Marques, J. C. (2008). Simultaneous analysis of free amino acids and biogenic amines in honey and wine samples using in loop orthophtha-laldeyde derivatization procedure. ]. Chromatogr. A 1189, 435-443. 

This chapter tackles the most important aspects of amino acid and biogenic amine formation during wine manufacture and aging. The significance of biogenic amines to wine quality and safety will also be reported. 

Herbert, P., Santos, L. and Alves, A. (2001) Simultaneous quantification of primary, secondary amino acids, and biogenic amines in musts and wines using opa/3-mpa/fmoc-d fluorescent derivatives, //. S Food Chemistry and Toxicology, 66(9), 1319-1325. 

Ababoueh, L., Afilal, M. E., Benabdeljelil, H., and Busta, F. F. (1991). Quantitative changes in bacteria, amino acids and biogenic amines in sardine (Sardina pilchardus) stored at ambient temperature (25-28°C) and in ice. Int J. Food ScL Technol. 26, 297-306. 

Biosynthesis In contrast to steroids and terpenes, there is no equivalent to the isoprene rule for alkaloids as a useful aid for structure determination and biogenetic investigations. It is generally accepted today that A. are formed in cyclization, condensation, and dimerization reactions from amino acids and biogenic amines with biogenic aldehydes and ketones. 

Arrieta, M. R, Rrats-Moya, M. S. (2012). Free amino acids and biogenic amines in Alicante Monastrell wines. Food Chemistry, 135, 1511-1519. http //dx.doi.org/10.1016/ j.foodchem.2012.06.008. 

Fiechter, G., Sivec, G., Mayer, H. K. (2013). Application of UHPLC for the simultaneous analysis of free amino acids and biogenic amines in ripened add-curd cheeses. Journal of Chromatography B. http //dx.doi.Org/10.1016/j.jchromb.2012.12.006. 

Herbert, P., Cabrita, M. J., Ratola, N., Laureano, O., Alves, A. (2005). Free amino acids and biogenic amines in wines and musts from the Alentejo region. Evolution of amines during alcoholic fermentation and relationship with variety, suh-tegion and vintage. Journal of Food Engineering, 66, 315-322. http //dx.doi.Org/10.1016/j.jfoodeng.2004.03.024. 

Kelly, M. T., Blaise, A., Larroque, M. (2010). Rapid automated high performance hquid chromatography method for simultaneous determination of amino acids and biogenic amines in wine, fruit and honey. Journal of Chromatography A, 1217, 7385-7392. http //dx.doi.Org/10.1016/j.chroma.2010.09.047. 

Lactam antibiotic drugs,amino acids, and biogenic amine as a PTC derivative, BTC amino acids,thiouracils, pyrimidines, and pyridines were separated in HPTLC and detected with the suggested method. 

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