Biogenic amines in wine: a review

Abstract

Summary Biogenic amines are formed from precursor amino acids, mainly by the microbial decarboxylation. The presence of these compounds plays a vital role in oenology because high amounts of them can lead to health problems. Thus, the origin, detection, and quantity of biogenic amines in wine are extremely important for winemaking. This study, focusing on the articles of latest 5 years, not only reviews the analytical methods used for the determination of biogenic amines but also describes the source of biogenic amines from the perspective of microbiological and oenological factors and summarises the strategies for the degradation of amines. The information presented in this review is important to alert about the inadequate quality of wine products, and efforts from the entire productive chain and the government are required to attain consumer safety.

Enzymes for Wine Fermentation: Current and Perspective Applications

“…Biogenic amines (BA) are another class of undesirable compounds in wine [95][96][97]. They originate from the grape berries or are formed during fermentation by activities of decarboxylase-positive microorganisms [98][99][100][101][102].…”

Accumulation of Biogenic Amines in Wine: Role of Alcoholic and Malolactic Fermentation

“…Among various reagents used for this purpose, the most popular were dabsyl chloride [32], dansyl chloride [33], benzyl chloride [34], 9-fluorenylmethoxycarbonyl chloride [35], o-phthaldialdehyde [36], fluorescein isothiocyanate [37], 1,2-naphthoquinone-4-sulfonate [38], 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate [29] and diethyl ethoxy methylene malonate [39]. However, the use of a derivatization agent is often affected by restrictions or disadvantages, e.g., the reaction with dansyl-chloride is slow and not specific, o-phthaldialdehyde reacts only with primary amines, 1,2-naphthoquinone-4-sulphonate requires reaction conditions characterized by high pH and temperature and other reagents exhibit short detection wavelengths and low stability [20]. Finally, it should be considered the optimum pH of the derivatization reaction (higher than 7.5), [29] that could affect the concentration of the organic acids, such as tartaric and malic acids, usually detected in the wine matrix [31].…”

A new derivatization reagent for determination of biogenic amines in wines

“…Apart from the primary metabolic products and many flavour compounds released during fermentations, some microorganisms produce secondary metabolic products such as biogenic amines. Guo et al (2015) reviewed factors affecting the presence of amines in wines and pointed out oenological factors and vintage, pH value, vinification techniques and ageing of lees, as the most important. It is generally agreed that the concentration of BAs is lower at the end of the alcoholic fermentation and increases mainly during malolactic fermentation.…”

“…Notwithstanding, HPLC is by far the most frequently reported technique for the determination of these compounds in Abbreviations: BAs, biogenic amines; BAs-NBA, FNBT derivatives of biogenic amines; CNBF, 2-chloro-1,3-dinitro-5-(trifluoromethyl)-benzene); FNBT, 1-fluoro-2-nitro-4-(trifluoromethyl)benzene; Him, histamine; Him-NFA, N-(2-(1H-imidazol-4-yl)ethyl)-2-nitro-4-(trifluoromethyl)aniline; Phe, phenethylamine; Phe-NFA, 2-nitro-N-phenethyl-4-(trifluoromethyl)aniline); Trp, tryptamine; Trp-NFA, N-(2-(1H-indol-3-yl)ethyl)-2-nitro-4-(trifluoromethyl)aniline; Tyr, tyramine; Tyr-NFA, 4-(2-(2-nitro-4-(trifluoromethyl)phenylamino)ethyl)phenol. wine samples (Guo et al, 2015). Due to the structural characteristics of BAs, their derivatization is usually needed and typical reagents for the amino group include o-phthaldialdehyde (OPA), 9-fluorenylmethylchloroformate, 2,4,6-trinitrobenzenesulfonic acid (TNBS), diethyl ethoxymethylenemalonate (DEEMM), 4-fluoro-3-dinitro-fluoromethylbenzene and dabsyl-chloride (DABS-Cl) (Guo et al, 2015;Gómez-Alonso et al, 2007;Hernández-Cassou and Saurina, 2011;Płotka-Wasylka et al, 2015;Wang et al, 2014) It should be noted, that International Organization of Vine and Wine (OIV) proposed derivatization with OPA and DEEMM for biogenic amines determination in musts and wine using fluorimetric (OIV-MA-AS315-18) and spectrophotometric (OIV-MA-AS315-26) detection methods (http://www.oiv.int/oiv/info/enmethodesinternationalesvin#autres).…”