Biogenic Amines in Grape and Wine

Biogenic amines are dangerous to human health and legal limits are fixed in grape and wine (structures are reported in Fig. 8.13). These compounds were found in fermented foods and beverages, such as cheeses, beer and fish, and meat products (Stratton et al., 1991 Shalaby, 1996). In wine, the most abundant are histamine, tyramine, putrescine, and phenylethylamine (Radler and Fath, 1991 Lehtonen, 1996). 

A relationship between putrescine, cadaverine, and histamine was suggested as responsible for numerous cases of food intoxication 

Histamine is probably the most important amine with physiological effects for human health. Ingested daily in small amounts, it normally degrades, but it still can induce a drastic response in a number of sensitive people inducing symptoms, such as skin redness, headache, nausea, stomach disorder, and respiratory troubles, this is a pathology known as Histamine Intolerance. Usually people affected by this disorder 

The maximal level of tolerance of histamine in wine has been established at 10 mg/L in Switzerland, 8 mg/L in France, 5-6 mg/L in Belgium, and 2 mg/L in Germany, however, the level for histamine-free wines should be 0.5mg/L (Bauza et al., 1995 Lehtonen, 1996). 

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Eder, R., Brandes, W., and Paar, E. (2002a). Influence of grape rot and fining agents on the contents of biogenic amines in musts and wines. Mitt. Klosterneuburg 52, 204-217. 

During alcoholic fermentation, the degree of maceration is the first factor that affects the extraction of some compounds present in the grape skin, especially phenolic compounds, which are responsible for the color of the wine. However, not only does the maceration affect the extraction of polyphenols but also of other grape components, such as proteins, polysaccharides and, also, amino acids, which are precursors of biogenic amines. In most red wines, alcoholic fermentation takes place... 

The various contaminations in foods are due to the presence of compounds dangerous for consumer health or that affect organoleptic characteristics of the product. Ochratoxin A (OTA) and biogenic amines are dangerous for human health, and their legal limits are fixed in grape and wine. Due to their negative sensory properties and very low sensory thresholds, 2,4,6-trichloroanisole and ethylphenols have to be practically absent in wine, or present at as low a level as is possible. 

Radler, F. and Fath, K.-P. (1991) Histamine and other biogenic amines in wines, in J. Rantz (Ed.) Proceedings of International Symposium on Nitrogen in Grapes and Wine, American Society for Enology and Viticulture, Davis (CA). 

Numerous research studies have been published dealing with the level and formation of biogenic amines in wine (see Moreno-Arribas and Polo, 2009), but only a few relate to Boby hs-affected grapes or wines (Eder et al., 2002a Hajos et al., 2000 Kallay, 2003 Kiss et al., 2006 Sass-Kiss and Hajos, 2005 Sass-Kiss et al., 2008). 

Flamini, R. and Larcher, R. (2008). Grape and Wine Contaminants Ochratoxin A, Biogenic Amines, Trichloroanisole and Ethylphenols, In Hyphenated... 

Hajos, G., Sass-Kiss, A., Szerdahelyi, E., and Bardocz, S. (2000). Changes in biogenic amine content of Tokaj grapes, wines and aszu-wines. J. Food Sci. 65,1142-1144. 

The ability of 40 strains of acetic acid bacteria isolated from grape must and wine to produce biogenic amines was screened in synthetic medium and wine (Landete et al. 2007b), but no positive results were obtained. No further mention regarding the formation of biogenic amines by acetic acid bacteria was found in the literature. 

Polyphenolic compounds can interfere in the analysis of red wines, and amino acids in the analysis of grape juices. Consequently several methods for isolating biogenic amines from wines and juices have been proposed liquid-liquid extraction with butanol of the sample preliminarily concentrated and adjusted to pH 1.5 (Almy et al, 1983) in general, for SPE is preferred strong cation exchange (SCX) under... 

Biogenic amines are usually detected by LC with a pre- or postcolumn derivatization with o-phthalaldehyde in the presence of mer-captoethanol, and fluorimetric detection of derivatives. A sample derivatization also has to be done to perform GC/MS analysis of grape juice or wine. Amines are distilled from the alkalized sample and trapped in an acidified solution. After concentration under vacuum, salts of ethylamine, dimethylamine, ethylamine, diethyl-amine, n-propylamine, isobutylamine, a-amylamine, isoamylamine, pyrrolidine, and 2-phenethylamine are derivatized with trifluoroacetic (TEA) anhydride. Their derivatives are extracted with ethyl ether. GC/MS is performed using a capillary fused silica PEG column with an oven temperature programmed for 8 min at 70 °C, l°C/min to 160°C, isotherm for 90min (Daudt and Ough, 1980). 

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