histamine and tyramine in beers: contents and relationships with other analytical data

JOURNAL OF FOOD COMPOSITION AND ANALYSIS 2,2 19-227 (1989)

Histamine and Tyramine in Beers: Contents and Relationships with Other Analytical Data

M. L. IZQUIERDO-PULIDO, M. C. VIDAL-CAROU, AND A. MARIN~FONT’

Nutrition and Food Science Unit, Faculty of Pharmacy, University of Barcelona, Diagonal s/n. 08028, Barcelona, Spain

Received April 3, 1989, and in revised form August 16, 1989

Histamine and tyramine contents were determined in 65 European beers consumed in Spain. Both amines were detected in all of the samples. Ninety-four percent of beers had less than 2 mg/liter of histamine. However, only 8% of all the samples showed values lower than 2 mg/liter oftyramine and 10% had more than IO mg/liter ofthis amine. Histamine and tyramine contents were greater in beers with high values of total acidity and of pH. It was also observed that the least fermented beers had the highest histamine contents. Amine contents were studied in beers of the same type and commercial brand, made in the same brewery but from different batches. It was observed that the presence of tyramine in these beers varied from one batch to another, as the contents of this amine ranged between 4.0 and 45.6 mg/hter. o 1989 Academic PRSS, hc.

INTRODUCTION

Histamine and tyramine are food components whose origin is accepted to be a consequence of decarboxylase microbial activity on their precursor amino acids (histidine and tyrosine, respectively). Decarboxylase action may be accomplished by microorganisms involved in the manufacturing process (fermentation) for foods such as wine, beer, sausage, cheese. Biogenic amines can be formed as a consequence of desired microbial activity, but it is also possible that some type of contamination might occur in these foods during their manufacture or storage which could produce high formation of these amines. Furthermore, the decarboxylation activity may be accomplished by microorganisms responsible for decomposition processes and/or decay of foods. At the present time it is in question whether the presence of these amines in foods should be considered “normal” and unavoidable (at least up to a certain level) in certain kinds of foods or whether their appearance could indicate the use of poor quality raw materials, defective manufacturing processes, and/or deterio- ration processes.

Beers could contain biogenic amines since fermentation processes are involved in their manufacture. However, the formation of these substances may not always be related to responsible microorganisms of fermentation.

High histamine contents in foods can have toxicological implications since they may give rise to “histaminic intoxications” (Edwards and Sandine, 198 1; Taylor, 1985). Likewise, tyramine has been linked with the occurrence of food-induced migraine (Crook, 198 1; Rivas and Marine, 1983). There are also indirect toxic effects

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220 IZQUIERDO-PULIDO, VIDAL-CAROU, AND MARINE-FONT

which may be attributed to biogenic amines in foods. In particular, hypertensive crises may occur in patients under treatment with monoaminooxidase-inhibiting drugs (MAOI) after ingesting foods with high contents of these substances (Blackwell et al., 1967; Marine et al., 1986). Pietrzik et al. (1975) point out that biogenic amines as well as alcohol must be taken into account when evaluating the toxic effects of alcoholic beverages. Likewise, Thalacker ( 1982) considers histamine to be an “undesirable component” in beers.

At the present time no maximum tolerable limits have been set for histamine in beers. Values between 2 and 10 mg/liter have been suggested for histamine in wines (Marquardt and Werringloer, 1965; Quevauviller and Maziere, 1969; Lafon-Lafour- cade, 1975; Battaglia and Friihlich, 1978). No maximum tolerable concentration has been suggested for tyramine. However, it is considered that ingestion of 6 mg of tyramine can increase blood pressure in patients taking MAO1 drugs, and that ingestion of 25 mg of this amine is sufficient to cause serious hypertensive crises (Ponto et al., 1977). There is substantial literature regarding cases of this type of interaction. As a recent example, Murray et al. (1988) described the appearance of symptoms of this interaction in a patient under treatment with tranylcypromide (an MAO1 drug) after drinking 250 ml of an Irish beer.

Histamine and tyramine may serve as possible “indicators” of defective food manufacturing processes related with poor sanitary conditions (Cerutti and Remondi, 1972; Rice and Koehler, 1976) and/or as indicators that poor-quality raw materials have been used (Ramantanis et al., 1984). In principle, these amines could be formed during the fermentation process by yeast activity; they may be the result of contamination during brewing or storage (Steiner and Laezlinger, 1978; Chen and Van Ghe- luwe, 1979; Zee et al., 1981; Cerutti et al., 1985); or they may have developed from the materials used (Chen and Van Gheluwe, 1979; Narziss et al., 1984; Wackerbauer and Toussaint, 1984). On the basis of the above, it has been suggested that brewery quality control programs include analytical determinations of biogenic amines, in order to gain a better idea of the quality of the raw materials and of the processes involved in beer brewing (Cerutti et al., 1985). It has also been suggested that by using good brewing practice and correct quality control, the following amine levels should not be surpassed in beers: 1 mg/liter of cadaverine and P-phenylethylamine, 0.1 mg/ liter of histamine, a few mg/liter of tyramine and tryptamine, and no hordenine nor putrescine should be detected (Cerutti et al., 1987).

Little data exist for histamine and tyramine content in beers consumed in Spain. The purpose of this study was to gain information on the histamine and tyramine contents of these beers. Beers brewed in Spain as well as imports from other European countries have been studied. Analytical parameters which may be related with the amine contents (alcoholic content, extract of original wort, real degree of fermentation, total acidity, and pH) have been also determined. Finally, histamine and tyramine contents in products of the same type and commercial brand, but from different batches, were compared in order to determine whether or not there was uniformity in the contents of these substances in the various batches of the brewing process.

Samples SAMPLES, MATERIALS, AND METHODS

Sixty-five beers were studied, 17 of which were Spanish and 48 were imports. All of the samples were purchased in the Spanish market. In addition, 10 beers from the

HISTAMINE AND TYRAMINE IN BEERS 221

same type and commercial brand but different batches were collected during a 2- month period.

Methods

Histamine. Histamine was determined using the spectrofluorometric method pro- posed by Vidal-Carou et al. (1989). This method consists of an extraction of histamine from the sample using n-butanol in alkaline medium (pH 12- 13) followed by a transferral of the histamine to 0.1 N HCl. Extraction of histamine with n-butanol was previously reported by Taylor et al. (1978). Subsequently, to achieve a fluorescent compound, a condensation reaction is carried out between histamine and ortho- phthalaldehyde. Finally, a spectrofluorometric reading is made at 340 nm excitation and 430 nm emission. Reliability of this method was satisfactory, so the precision in terms of coefficient of variation (CV) was 7.75% (n = 8) and the recovery was (93.4%, n = 24).

Tyramine. The spectrofluorometric method of Rivas-Gonzalo et al. (1979) was employed. This method consists of an extraction of tyramine from the sample in alkaline medium with ethyl acetate, followed by a transferral of the tyramine to 0.2 N HCl. Finally, a fluorescent complex between tyramine and cY-nitroso+-naphtol is formed, and a spectrofluorometric reading at 450 nm excitation and 540 nm emission is made. Precision (CV = 4.65%; n = 8) and recovery (94.45%; n = 24) ofthis method were satisfactory.

Alcoholic content, extract of original wart or original gravity (percentage of extract (w/w), including sugars, corresponding to wort), and real extract (density of residue after distillation, without the alcohol, but restored to original volume with distilled water) were determined automatically using a Technicon beer analyzer (Technicon International Division, 1979). The alcohol is determined thermometrically in one channel of the apparatus and the beer density is determined in the other channel of this system by a Paar density meter. The extract of original wort is calculated automatically from the alcohol content and density by a system computer.

Total acidity, pH, and real degree of fermentation were determined using the “American Society of Brewing Chemists Methods” (ASBC, 1987). Total acidity was determined by potentiometric titration with 0.1 N NaOH and results were expressed in grams of lactic acid for 100 g of beer. The pH was measured with a Crison 70 1 pH meter. The real degree of fermentation represents the percentage of extract of original wort which has been fermented, and it was calculated using the formula: RDF (%) = 100 (1 - E/O) [l/l - (0.005 16 1 - E)], where RDF is the real degree of fermentation, E is the real extract, and 0 is the extract of original wort.

RESULTS AND DISCUSSION

Histamine and tyramine contents in 65 samples of beer corresponding to different commercial brands, along with the other parameters studied, are shown in Table 1 for beers made in Spain, and in Table 2 for imported beers. All data in these tables are mean values of duplicate determinations. Most samples showed values of extract of original wort, alcoholic content, total acidity, pH, real degree of fermentation, and real extract in accordance with the limits established by Spanish regulations (Minis- terio de la Presidencia de Gobierno, 1984) with which both domestic and imported


TABLE 1

HISTAMINEANDTYRAMINECONTENTSANDOTHERANALYTICALPARAMETERS INSPANISHBEERSOFDIFFERENTCOMMERCIALBRANDS

TYPE OF BEER HISTAMINE TYRAMINE ALCOHOLIC EXTIRACT OF REAL DEGREE TOTAL ACIDITY pH REAL (w/L) (mg/I~) CONTENT (A ) ORIGINAL WORT FERMENTATION (TA) (% w/w) EXTRACT

(% v/v) (0) (X w/w) (RDF) (%) (% w/w)

0.6 2.3 4.57 11.00 65.02 0.15 3.93 3.98 0.b 6.2 4.58 11.11 67.99 0.09 4.65 3.70 0.7 2.1 5.63 12.56 69.44 0.16 4.34 4.02

seer- 0.6 23.3 5.38 12.93 64.32 0.20 4.03 4.82 0.4 2.5 4.50 11.00 __- 0.09 4.36 -- 0.5 2.2 4.70 11.50 _-. 0.16 3.95 -- cl.4 1.9 4.50 11.50 0.17 4.30 --

1.8 5.3 5.44 13.03 64.47 0.16 4.21 4.84 Special 0.3 2.1 5.68 13.16 66.70 0.15 3.96 4.59 bee-P 1.2 2.5 5.70 13.33 65.98 0.19 3.93 4.75

0.7 5.3 5.68 13.34 65.79 0.24 4.29 4.78 0.7 24.7 5.69 13.36 66.85 0.18 4.25 4.57 0.4 3.7 5.50 13.00 0.20 4.35 --

Special extra 0.8 2.6 6.65 15.15 b7.10 cl.25 4.36 5.26 beer= ___---____----__"1'---~----~~~.~---~-~~~~-~--.--~.--~~~~!.-.~-~~--.~~~!~------~---~~~~~--~----~~~~-~~~~~~~-- Non-alcoholic 0.4 5.0 0.98 5.73 27.29 0.04 4.65 4.20 beer* 0.4 3,b 0.48 5.71 27.32 0.06 4.96 4.94

Spanish law ranges: - beer: A: 4.5-5.5; 0: > 11: RDF: >46; TA: < 0.3; pH: 3.5-5: E: >3.

b special beer: A: 5.5-6.5; 0: > 13: RB(DF: > 46: TA: < 0.3; pH: 3.5-5: E: >3.

c special extra beer: A: >6.5; 0: X15: RDF: >46: TA: < 0.3; P": 3.5-5; E: > 3.

d non-alcoholic beer: A: < 1

beers must comply. Only five beers showed values of total acidity greater than the established limit.

In all of the beers studied both amines were detected. Tyramine content was higher than that of histamine in all of the samples. It is worth pointing out that in wines the reverse occurs and histamine contents are higher than tyramine contents (Vidal- Carou, 1987). The histamine and tyramine distributions in all samples analyzed are shown in a histogram (Fig. 1). There is a wide overall variability in tyramine contents. The histamine values found in all the Spanish beers and 92% of the imported beers were below 2 mg/liter. The tyramine contents were higher than those of histamine. Only 8% of all samples had levels below 2 mg/liter and 10% had more than 10 mg/ liter. The contents of both amines were especially high in a “Pilsen”-type Czechoslo- vakian beer, which had 17.0 mg/liter of histamine and 46.8 mg/liter of tyramine. Both amine contents were lower in nonalcoholic beers than in “normal” beers. This is in accordance with Chen and Van Gheluwe ( 1979) and Zee et al. (198 1). However, as the number of samples of nonalcoholic beers was low, it is not possible to show a definitive conclusion in this respect.

Levels of histamine and tyramine found in beers were too low to produce direct toxicological effects. However, if the value of 6 mg of tyramine reported by Ponto et al. (1977) to increase blood pressure is considered, 7.7% of beers could provoke indirect toxicological effects in patients under treatment with MAO1 drugs after consumption of 330 ml of beer (volume of a normal-sized can). If consumption of three cans (990 ml) is considered the percentage is 23.1%.


TABLE 2

HISTAMINEANDTYRAMINECONTENTSANDOTHERANALYTICALPARAMETERS INIMPORTEDBEERSOFDFFERENTCOMMERCIALBRANDS

COUNTRY HISTAMIEE TYRAMINE ALCO"OLIC EXTMCT OF REAL DEGREE TOTAL ACIDITY pH REAL OF ORIGIN (mg/L) (me/L) CONTENT (A) ORIGTNAL WORT FERMENTATION (TA) (X "I") EXTRACT

(X v/v) (0) (X w/w) (RI)F) (%) (X w/r)

BELGIUM 1.6 30.6 5.28 12.04 68.10 0.53 3.45 4.01 0.6 3.8 5.05 11.40 69.03 0.16 4.42 3.68 0.7 4.1 5.09 11.47 69.09 0.17 4.37 3.70 4.9 6.7 5.19 13.04 61.55 0.58 3.53 5.23 4.4 18.9 5.47 12.99 65.10 0.49 3.55 4.74 1.8 7.4 6.45 15.19 65.01 0.20 4.16 5.60 1.7 3.1 7.88 17.94 66.42 0.26 4.07 6.42 0.3 2.5 5.00 12.00 __- 0.13 3.93 -- 1.3 5.8 12.00 24.00 -- __ --

CZECHOSLOVAKIA 17.0 46.8 4.15 11.69 55.26 0.17 4.37 5.41

DENMARK 0.4 1.9 5.00 13.00 __- 0.15 4.33 - -

FRANCE 1.0 3.3 4.64 11.35 63.70 0.12 4.41 4.28 1.0 4.7 6.35 14.65 66.44 0.22 4.15 5.18 0.6 18.5 5.00 11.70 0.26 4.32 - -

1.6 3.8 6.50 16.70 0.20 4.22 - -

GERnAhY F.R. 0.9 2.3 0.8 3.1 1.0 1.8 0.8 1.9 0.9 7.9 0.8 7.7 0.‘) 3.1 1.8 6.3 1.0 1.5 1.0 2.4 0.8 2.1 0.7 2.5 0.6 2.7 0.3 5.6 1.4 7.0 1.3 3.3 0.5 14.5 0.8 4.0 0.8 2.7 0.7 8.4 0.7 2.9 0.6 2.4 0.6 2.4 2.6 6.3

________________-_-_____________

HOLLAND 0.4 2.0 0.6 3.0 0.7 2.5 0.6 3.3 0.5 2.1 0.3 3.3

4.87 4.61 5.12 4.79 4.86 4.68 4.74 4.99 5.50 5.48 5.41 5.50 5.52 5.59 5.35 5.44 5.24 5.50 5.00 5.00

__

5.00 12.00

5.00 12.00 _-- 0.13 4.07 -- 4.50 11.30 0.26 4.17 -- 4.90 11.90 ___ 0.25 4.12 -- 5.40 12.80 0.29 4.56 -- 0.14 6.36 3.2, 0.07 4.83 6.16 0.10 4.79 __- 0.20 4.20 --

11.40 66.48 11.15 64.50 12.22 65.00

11.13 67.17 11.90 63.42 11.25 64.75 11.46 04.41 12.37 62.60 12.46 68.30 12.39 68.51 12.46 67.28 12.55 67.85 12.30 69.60 12.65 70.02 12.57 65.88 12.40 67.99 12.55 64.57 12.50 13.00 _--

13.00 11.70 ___

11.00 ___

11.60 33.80 _-_

0.16 0.34 0.23 0.13 0.22 0.18 0.30 0.18 0.15 0.15 0.15 0.19 0.25

0.20 0.21 0.23 0.17 0.21 0.23 0.18 0.15 0.14

4.60 3.87

3.85 4.88 4.64 4.32 4.25 4.00 4.67 4.60 4.71 4.47 4.32

4.41 4.51 4.46 4.95 4.49 4.24 4.59 4.36 4.52 --

3.98 4.11 4.46 3.80 4.53 4.12 4.24 4.82 4.13 4.08 4.26 4.22 3.91 4.17 4.48 4.15 4.64

- - __ __ - - __ _- __

IRELAND 1.6 5.3 4.99 11.79 65.80 0.25 3.95 4.20 0.5 3.0 5.70 12.70 0.16 4.04 -- 1.0 3.8 5.00 12.00 __- 0.22 4.02 --

Some authors have identified relationships between contents of both biogenic amines in beers and other analytical parameters. The Pearson correlation coefficients for the relationships we studied are given in Table 3. The degree of significance found in each case is also included. The results indicate that there was no significant correlation between the alcoholic content and the contents of both amines, nor between their content and the extract of original wort. This finding is contrary to that suggested by Chen and Van Gheluwe (1979). However, a statistically significant correlation was obtained (CX < 0.001) between the contents ofboth amines and the total acidity. High


HISTAMINE Amines content in me/~

a TYRAMINE

FIG. 1. Distribution of histamine and tyramine contents in Spanish and imported beers.

values for total acidity could indicate acidification by microorganisms (Montes, 198 1). It is possible that those microorganisms could have the ability to form amines. Statistically significant correlations were also observed between the pH and the content of both amines (histamine/pH: (Y < 0.00 1; tyramine/pH: (Y < 0.0 1) and between the histamine content and the real degree of fermentation ((Y < 0.005). Thus, the least fermented beers showed the highest histamine contents. This, along with the relationship which exists between the total acidity, the pH, and the histamine content, is in agreement with the hypothesis that the least fermented beers (those which still

TABLE 3

CORRELATION COEFFICIENTS BETWEEN HISTAMINE OR TYRAMINE CONTENTS AND OTHER ANALYTICAL PARAMETERS STUDIED

NO of samples Histamine Tyramine

Alcoholic content 60 0.0635 -0.0451

Extract of original wart 62 0.1647 -0.0035

Total acidity 62 0.7445*** 0.4380***

PR 62 -0.5673*** -0.3498*

Real degree of fermentation 38 -0,4629** -0.1321

Degree of signification: *** 99.9% ** 99.5%

* 99.0%


TABLE 4

HISTAMINE AND TYRAMINE CONTENTS IN BEERS OFTHE SAME COMMERCIAL BRANDS AND TYPE, MADE INTHESAMEBREWERYBUTFROMDIFFERENTBATCHES

NO of sample Histamine (me/L)

---___________------_____________

1 0.8 2 0.9 3 0.8 4 0.8 5 0.8 6 0.7 7 0.7 8 0.8 9 0.8

10 0.7

Tyramine (w/L)

9.8 12.8 22.5 45.3 16.3 13.0 32.6 45.6

4.0 32.8

contain high amounts of fermentable sugars) are the most susceptible to contamination by microorganisms which can give rise to an increase in the amine contents in the final product.

The technological interest of biogenic amines as possible “indicators” of defective brewing processes was mentioned earlier. However, no definitive values or concrete relationships were found which would allow one to determine on the basis of final amine content in beers if a brewing process has been correct. We therefore cannot assert that the relatively high tyramine contents are indicative of beers which have been incorrectly brewed. Nevertheless, there must be some differences in conditions of the brewing process which account for the wide range of tyramine contents (from 1.5 to 46.8 mg/liter).

A study was performed to verify if the wide range of tyramine contents in various beers is also found in beers of the same type and commercial brand from different brewing batches. The histamine and tyramine levels found in the 10 samples studied are shown in Table 4. Practically no variation in histamine contents was demon- strated. The small variations (0.7 to 0.9 mg/liter) could be due to deviations in the method and not to differences in the real contents of this substance. The results for tyramine varied from 4.0 to 45.6 mg/liter. Thus it may be asserted that the content of tyramine in this beer varies depending on the brewing batch. We believe that it would now be interesting to study the source(s) of these amines in beers. Variability in their contents could be due to ingredients and/or to yeast used, to possible microflora present in the yeast, or to other factors.

ACKNOWLEDGMENTS

This work was made possible by a grant from the CIRIT (Comissii, Interdepartamental de Recerca i Innovacib Tecnoltigica, Generalitat de Catalunya, Spain) and by a grant from the Fondo de Investigaciones Sanitarias de Ia Seguridad Social (Ministerio de Sanidad y Consumo, Spain).

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histamine and tyramine in beers: contents and relationships with other analytical data

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