Manual Biochemistry of Biogenic Amines

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Higher levels of putrescine and cadaverine can promote a negative flavor in wines, associated essentially with rancid notes [15]. On the other hand, histamine and tyramine are considered the main monoamines responsible for toxicity on wine consumers, since can promote symptoms similar to allergic reactions, namely gastrointestinal, cardiac, cutaneous and also nervous effects [16]. These effects occur mainly in susceptible individuals due to the presence of ethanol, which inhibit or reduce the activity of the enzymes responsible for the metabolism of BAs monoamine and diamine oxidase [17].

The consumer safety, the wine quality control and the applied legislation are the main priorities for the wine industry. In order to facilitate the international trade, the International Organization of Vine and Wine OIV standardized the analytical methods and published two chromatographic methods for the determination of BAs [20]. However, even today, it is still a challenge the development of a simple, fast, low cost and reliable method for the determination of BAs in wines. In this sense, this review provides an overview of the recent advances observed in the analytical methodologies used for the determination of BAs in wines in the last decade, focusing the improvements, the optimization and the novelties in this field.

Additionally, Sensors, Enzymatic and Immunoassays procedures as well as commercial test kits are already available, for the rapid detection of histamine and tyramine in wines [31]. Table 1: Chromatographic methodologies for the determination of biogenic amines in wine published in the last decade.

Table 1 summarizes the chromatographic methods used to quantify BAs in wine, in the last decade. Typically the wine samples are analyzed directly or after a simple treatment with Polyvinylpolypyrolidone PVPP to remove some phenolic compounds []. Nowadays, most methodologies usually involve sample preparation prior to analysis, not only to remove some compounds that may interfere with the analysis but also to concentrate the analytes.

Also, pre-column or post-column derivatization is often needed for appropriate detection, since BAs do not have enough absorption in the UVVis or FLD wavelength ranges. The derivatization step is also used to improve the separation in the RP columns, reducing the polarity of the original compounds [17,26,28,29,].

The determination of dansylated amines in wines has been the target of several studies [37,38]. The derivatization and chromatographic conditions have been optimized using the central composite designs, with BAs being detected by fluorescence [32] or UV-Vis [17]. FLD revealed better sensitivity to detect dansylated amines [17,32]. DNS-Cl has been largely used as pre-column derivatizing agent in the determination of BAs in wines and it produces stable derivatized compounds.

Jiang, et al. A low-cost method based on thin layer chromatography using densitometry to quantify the dansylated BAs was also developed [40] and it can be used for routine analysis of histamine, tyramine, putrescine and cadaverine in wine. Ortho -Phthalaldehyde OPA is another recognized reagent for the derivatization of biogenic amines. OPA is one of the most used derivatization reagent and for that reason several studies report its use for the determination of BAs in wines. OPA derivatives are less stable but the reaction can occur at room temperature in a short time [].

Pereira, et al. Also, Wang, et al. This pre-column derivatizing agent enables the quantitative determination of secondary and primary amines, with no side-reaction products and produces stables derivatives at room temperature for several days, which can be detected by an UV detector, usually available in most chromatography laboratories [45].

Recently, a new derivatization reagent, namely 1-fluoronitro trifluoromethyl benzene FNBT , was also used for the determination of histamine, tyramine, tryptamine and phenyl ethylamine in wines using RP-HPLC-DAD analysis, showing simple and less-time consuming derivatization when compared to other methods [21]. They reported that this combination enables the analysis of BAs in wine reducing the run time and the use of organic solvents.

The LODs was not lower than those obtained by RP separation, however this method has the advantage that BAs do not need derivatization to be separated and detected [46]. Finally, a gas chromatography—mass spectrometry GC-MS method was also used for the quantification of volatile and nonvolatile biogenic amines in Port wines, using Isobutyl Chloroformate IBCF as derivatization agent. Even though the method implies a complex procedure, it provides an accurate identification and enables the quantification of a higher number of BAs compared to the typical LC methods [24].

Automated on-line combination of capillary isotachophoresis—capillary zone electrophoresis cITP—CZE with UV detection was successfully used for determination of selected BAs in wines, without a derivatization step [47].

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BIOGENIC AMINES AND ANTIOXIDANT CAPACITY OF JUICE AND WINE FROM BRAZILIAN HYBRID GRAPEVINES

The authors concluded that this method can be more sensitive for the determination of BAs in wines when comparing to other chromatographic and electrophoretic methods, due to the online pre-concentration of selected analytes in the cITP step, the high separation efficiency of the CZE and the fact that BAs can be detected by selective photometric detection, without needing derivatization. After a simple sample preparation, without needing derivatization, they determined a group of important BAs in wines, in a min run.

Table 2: Electrophoretic methodologies for the determination of biogenic amines in wines published in the last decade. The electrophoretic separation took just 10 min for the migration of 9 BAs and the wine samples were just submitted to a PVPP clean-up and filtrated prior to analysis. The development of biosensors has recently gained much interest among the scientific community because these low-cost devices can give results in a few minutes, without needing any kind of sample pre-treatment and the possibility to be used outside the laboratory.

BAs biosensors, resulting from the combination of different enzymes for the bio-recognition of the BAs, are then a good option for a rapid determination of these compounds in wine [50,51]. The most used signal transducers of these biosensors are electrochemical sensors, which are generally based on the fluorescence response between BAs and sensor molecules interactions. Henao-Escobar, et al. On the other hand, Basozabal, et al. Table 3 summarizes the use of biosensors for the determination of BAs in wines. Table 3: Recent studies using biosensors for the determination of biogenic amines in wines.

Biochemistry of Biogenic Amines | Leslie Iversen | Springer

Although the enzyme-linked immunosorbent assay ELISA presents high sensitivity and precision, in the last decade, no studies were found in literature reporting this procedure for determining BAs in wines. Indeed, this methodology is time-consuming and may be expensive for a small number of samples [54]. The last report was made by Marcobal, et al. This method was based on the reaction of histamine with 1,2-naphthoquinonesulfonate to form a derivative that can be detected by a UV-Vis spectrophotometer [57].

The procedure is simple and can be automatized and miniaturized. In the last decade, several methods for the determination of BAs in wines have been developed, in order to improve the precision and sensitivity. Most procedures use liquid chromatography and DNS-Cl as derivatizing reagent.

However, other reagents have been studied and are showing very promising results, regarding the time-consuming for sample preparation, analysis and also lower solvent consumption. The new trend for the determination of BAs in wines will go through portable, faster and cheaper methodologies to meet the demands of the wine industry. Thus, the development of biosensors has been gaining interest. Similarly, CE also demonstrates lower costs and faster results, without using the derivatization step.

Short Communication. Journal of Analytical, Bioanalytical and Separation Techniques. Copy doi. Analytical methodologies for the determination of biogenic amines in wines: an overview of the recent trends. Citation Pereira, V. Santos, M. Biogenic amines: their importance in foods. Crossref 2. Shalaby, A. Significance of biogenic amines to food safety and human health.

Crossref 3. Sebastian, P. Molecular identification of lactic acid bacteria occurring in must and wine. Crossref 4. Del Prete, V. Occurrence of biogenic amines in wine: The role of grapes. Crossref 5. Brink, B. Occurrence and formation of biologically active amines in foods. Crossref 6. Cecchini, F. Effect of grape storage time on biogenic amines content in must. Crossref 7. Herbert, P. Relationship between biogenic amines and free amino acid contents of wines and musts from Alentejo Portugal.

Pubmed Crossref 8.

Biogenic amine determination in wine fermented in oak barrels: Factors affecting formation. Crossref 9. Izquierdo Ca-as, P. Amino acids and biogenic amines during spontaneous malolactic fermentation in Tempranillo red wines.

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Crossref Influence of technological practices on biogenic amine contents in red wines. Vidal-Carou, M.


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Histamine and tyramine in spanish wines: Relationships with total sulfur dioxide level, volatile acidity and malolactic fermentation intensity. C, Marques, A.