Irradiation Effects on Biogenic Amines in Korean Fermented Soybean Paste During Fermentation

ABSTRACT: Irradiation effects on biogenic amines (BAs) and microbiological populations of Korean fermented soybean paste were investigated during fermentation. Soybean paste was prepared and irradiated with doses of 5,10, and 15 kGy, and then fermented at 25 °C for 12 wk. Bacillus spp. and lactic‐acid bacteria decreased by irradiation but increased during fermentation. Biogenic amines detected were putrescine, cadaverine, β‐phenylethylamine, spermidine, spermine, tryptamine, histamine, tyramine, and agmatine. A significant difference was not observed in BA content between control and irradiated samples immediately after gamma irradiation. However, 4 kinds of BAs, putrescine, tryptamine, spermidine, and histamine, showed significant reduction by irradiation during fermentation (P < 0.05).     

不同加工对生物胺影响的研究

为破坏生物胺结构、抑制生物胺产生、有效去除生物胺,通过HPLC-柱后衍生-FLD检测技术分析了7种生物胺(酪胺、腐胺、尸胺、组胺、胍丁胺、亚精胺、精胺)在不同加工处理后的变化情况。结果表明,超声、微波、加热对生物胺没有破坏作用,超声和山梨酸钾前处理对鲅鱼生物胺的抑制率分别为45.89%和58.36%。醋酸、泡菜汁对生物胺的去除率为17.59%和27.76%。因此,生物胺不能通过超声、微波、加热技术来消除,可以通过控制细菌生长和酸液浸提等方式来抑制和去除。     

Production of Biogenic Amines and Their Potential Use as Quality Control Indices for Hake (Merluccius merluccius, L.) Stored in Ice

ABSTRACT: The production of tyramine, histamine, putrescine, cadaverine, agmatine, and spermidine was studied for use as quality indices in muscle of gutted hake stored in ice for 25 d. The changes in biogenic amine concentrations were correlated with trimethylamine nitrogen levels. All concentrations except for spermidine, increased progressively throughout storage. During storage, cadaverine reached 72.14 mg/kg while there were no significant increases in histamine and tyramine. The levels of free amino acids, which may be metabolized into biogenic amines, were not correlated to respective biogenic amines levels. The production of cadaverine and agmatine occurred prior to spoilage and these biogenic amines may indicate freshness of hake stored in ice.     

Biogenic amines in Brazilian cheeses

The levels of biogenic amines in Brazilian cheeses were investigated for the first time. Ninety-two samples of 10 types of cheese were purchased at retail stores. The amines were extracted using hydrochloric acid, partitioned into diethyl ether, separated through reversed-phase ion-pair chromatography and quantified fluorimetrically after postcolumn derivatization with o-phthaldehyde. Overall, spermine was the most prevalent amine (93%), followed by histamine (65%), 2-phenylethylamine (62%), spermidine (61%), putrescine (60%), cadaverine (59%), serotonin (44%), agmatine (38%), tyramine (37%) and tryptamine (29%). Spermine, agmatine, 2-phenylethylamine, serotonin, spermidine and tryptamine were detected at low levels (< 4.10 mg/100g). Cadaverine, tyramine, histamine and putrescine were present at levels up to 111.00, 21.25, 19.65 and 17.37 mg/100g, respectively. There was variability on the type and levels of amine in each kind of cheese suggesting that amine formation and accumulation in cheese could be prevented. Efforts should be made to understand amine formation in cheese in order to optimize technology and secure low amine levels. Susceptible individuals should be advised to consume cheeses with low biogenic amines contents.     

Biogenic amines and sensory changes associated with the microbial flora of Mediterranean gilt-head sea bream (Sparus aurata) stored aerobically at 0, 8, and 15 degrees C.

Changes in the concentrations of tyramine, agmatine, putrescine, cadaverine, spermidine, tryptamine, spermine, histamine, and trimethylamine were studied in parallel with the development of the microbial population during the storage of Mediterranean gilt-head sea bream (Sparus aurata) at three temperatures (0, 8, 15 degrees C). Changes in sensory scores were also recorded. Pseudomonads and H2S-producing bacteria were the dominant microorganisms. Enterobacteriaceae and lactic acid bacteria were also present in the fish microflora. Among the biogenic amines, putrescine and cadaverine were detected when pseudomonads exceeded 10(6) to 10(7) CFU/g. Histamine was produced only in samples stored at 15 degrees C. Tyramine, tryptamine, agmatine, and trimethylamine were absent regardless of the storage temperature.     

反相高效液相色谱-柱后衍生法分析检测鱿鱼中的生物胺

建立了水产品中多组分生物胺的反相高效液相色谱-柱后衍生-荧光检测方法。采用荧光试剂邻苯二甲醛（OPA）为柱后衍生化试剂,在Capcell Pak MG-C18色谱柱上,通过梯度洗脱使酪胺、腐胺、尸胺、组胺、胍丁胺、精胺和亚精胺等7种生物胺得到良好分离,在给定的浓度范围内,各组分生物胺呈现良好线性相关（R^2〉0.999）。在水产品中添加生物胺混合标准溶液,平均回收率为88.3%～110.1%,相对标准偏差RSD小于10%。结合水产品的感官鉴定、pH值和TVBN值测定等方法检测水产食品的新鲜程度,分析了鱿鱼在不同保藏温度、保藏时间下的生物胺种类及含量的变化。其中胍丁胺和尸胺在鱿鱼的保藏过程中发生最显著变化,可以作为其质量变化的参考指标。     

Quality of monosex tilapia under ice storage: Gutting effects on the formation of biogenic amines,biochemical, and microbiological characteristics

Effects of gutting on biogenic amine (putrescine, cadaverine, histamine, agmatine, tyramine, spermidine, and spermine) formation, biochemical (pH, TVBN, K value), microbial (APC, H₂S producing, Coliform bacteria), and sensory quality of farmed monosex tilapia (Oreochromis niloticus) was studied during ice stored at 4 ± 2ºC. Spermine and spermidine levels were high with cadaverine reached 4.66 ppm in gutted sample. The other amines were detected at relatively low level. K value of both samples crossed 60% on 15th and 18th day, respectively. The total phenolic content exceeded 7 log cfu/g after sensory rejection. The shelf life of whole and gutted samples was estimated to be 24 and 21 days, respectively.     

Biogenic Amine Content of Beers Consumed in Turkey and Influence of Storage Conditions on Biogenic Amine Formation

The biogenic amine content of beers available in Turkey, both domestic production and imported products, was investigated. A total of 17 domestic and 13 imported beers were evaluated in terms of 8 different biogenic amines (histamine, tyramine, spermine, spermidine, 2‐phenylethylamine, putrescine, tryptamine and cadaverine). HPLC methodology with pre‐column derivatization and photodiode array detection after derivatization with dansyl chloride was used for quantification. In addition, the evolution of important amines such as histamine, tyramine, putrescine and cadaverine were investigated during different storage conditions by response surface methodology. The results indicated that both storage temperature and storage time were important factors affecting biogenic amine content. Histamine and putrescine increased during storage, but then decreased after reaching a maximum level after six weeks. With the biogenic amines tyramine and cadaverine, the amounts increased during the entire storage period. At higher storage temperatures, the formation of biogenic amines increased.     

Biogenic amine content during the manufacture of dry-cured lacón, a Spanish traditional meat product: Effect of some additives

The content of nine biogenic amines (agmatine, tryptamine, 2-phenylethylamine, putrescine, cadaverine, histamine, tyramine, spermidine and spermine) was determined throughout the manufacture of dry-cured lacón, a traditional dry-salted and ripened meat product made in the north-west of Spain from the fore leg of the pig following a similar process to that of dry-cured ham. The effect of the use of additives (glucose, sodium nitrite, sodium nitrate, sodium ascorbate and sodium citrate) on the biogenic amine content during manufacture was also studied. Tryptamine and spermine were the main biogenic amines in fresh meat, while tryptamine and cadaverine were the most abundant at the end of the manufacturing process. During ripening the total amine content increased significantly (P<0.05) in the batches made both without and with additives. The use of additives significantly (P<0.05) increased the total amine content and the content of tryptamine, tyramine and histamine. The total biogenic amine content at the end of the manufacturing process was low as expected for a product in which there is little active microbial metabolism during manufacture.     

Tyramine production of technological important strains of <Emphasis Type="Italic">Lactobacillus</Emphasis>, <Emphasis Type="Italic">Lactococcus</Emphasis> and <Emphasis Type="Italic">Streptococcus</Emphasis>

The aim of this paper was to study the biogenic amines (histamine, tyramine, putrescine, cadaverine, agmatine, spermine and spermidine) production of selected technological important lactic acid bacteria (strains of the genera Lactococcus, Lactobacillus and Streptococcus). Three methods (ion-exchange chromatography (IEC), PCR and cultivation method with pH indicator) were used. Within the 39 strains of lactic acid bacteria tested, the production of tyramine (formed by tyrosine decarboxylase) was detected in eight strains (3 strains of Lactococcus lactis subsp. lactis, three strains of Lactococcus lactis subsp. cremoris, 1 strain of Streptococcus thermophilus and 1 strain of Lactobacillus delbrueckii subsp. bulgaricus). The other tested biogenic amines were not detected. Cultivation in decarboxylation broth seems to be the least accurate method for the detection of biogenic amines due to enhanced risk of false-positive reactions. Therefore, in order to detect bacteria producing biogenic amines, the combination of PCR and chromatographic methods (e.g. IEC) can be recommended.     

发酵香肠中生物胺生成量的菌株效应分析

本实验对乳杆菌(米酒乳杆菌和戊糖乳杆菌)和片球菌(戊糖片球菌和小片球菌)在发酵香肠中生物胺的生成量进行了分析。结果表明,供试乳杆菌和片球菌均能产生不等量的组胺、尸胺、腐胺、酪胺、亚精胺和精胺,但都不产生色胺,产品中的生物胺生成量表现出明显的菌株效应。采用复配菌种(片球菌+葡萄球菌)发酵可以明显降低香肠中组胺、尸胺、腐胺和酪胺以及总生物胺的含量。     

Levels of biogenic amines in typical vegetable products

Biogenic amines were determined in frozen spinach purée, ketchup, concentrated tomato pasta and frozen green pea as N-benzamides, by micellar electrokinetic capillary chromatography. Putrescine and spermidine were observed in most samples at detectable levels, while histamine, spermine and cadaverine concentrations were frequently below detection limits. Maximum mean levels (33.6 and 52.5 mg kg⁻¹ of tyramine and putrescine, respectively) were found in ketchup and 46.6 mg kg⁻¹ of spermidine in pea. Levels of histamine and spermine were low, and those of cadaverine and tryptamine low or medium. Thus, biogenic amines in the observed vegetable products should not be of a risk for healthy consumers.     

CHANGES IN BIOGENIC AMINE CONTENTS AND SENSORY QUALITY OF SARDINE (SARDINA PILCHARDUS) STORED AT 4C AND 20C

Biogenic amines (tyramine, putrescine, cadaverine, histamine, spermidine and spermine) in sardine during the storage at two temperatures (4C and 20C) were investigated. Changes in sensory scores were also recorded. Significant differences between storage times were found. The levels of tyramine, putrescine, cadaverine and histamine increased as decomposition of sardine progressed at both 4C and 20C. Spermidine and spermine did not change throughout storage. Putrescine was the main biogenic amine formed, followed by tyramine, cadaverine and histamine. Histamine remained lower than the toxic level of 100 mg/kg in the samples stored at 4C whereas it exceeded the toxic level after 16 h at 20C. The increase in histamine concentration was lower than tyramine and putrescine at both temperatures. Sensory scores gradually decreased during the storage.     

Effect of delayed gutting on biogenic amine contents during ripening of European anchovies

The effect of delayed gutting on biogenic amine formation during ripening of European anchovies (Engraulis encrasicholus) was studied. The main difference between the two processes was the use of gutted or ungutted fish in the first step of ripening. Biogenic amines and microbial counts were studied in seven batches of samples taken during manufacturing from fresh anchovies and from anchovies throughout ripening. The formation of amines commonly related to fish spoilage (histamine, tyramine, cadaverine, putrescine and agmatine) was significantly higher in the first step of ripening of batches in ungutted fish. In contrast, no differences were observed between the content of the natural polyamines spermine and spermidine.     

酿酒工艺对葡萄酒中生物胺的影响

探讨了不同酿酒工艺对葡萄酒中生物胺(组胺、苯乙胺、酪胺、色胺、腐胺、尸胺、精胺和亚精胺)含量的影响。结果显示,葡萄酒酿造过程中生物胺主要在酒精发酵和苹果酸-乳酸发酵过程产生。酒精发酵过程生成量较少,主要产生腐胺和精胺,果胶酶的使用、酵母接种量、发酵温度等因素可以调节酒精发酵过程生物胺的生成量;乳酸菌是葡萄酒生物胺最主要来源,在苹果酸-乳酸发酵过程中会产生大量的组胺和色胺。     

Effect of controlled atmospheres enriched with O2 in formation of biogenic amines in chilled hake (Merluccius merluccius L.)

Changes in biogenic amines (tyramine, histamine, putrescine, cadaverine, agmatine and spermidine) contents during the storage of chilled hake in a controlled atmosphere with four gas mixtures of different CO₂ and O₂ concentrations, (CO₂/O₂/N₂ at 60/15/25, 40/40/20, 60/40/0 and 40/60/0 respectively) were studied. Biogenic amines were determined by high-pressure liquid chromatography with post-column derivatization and ortho-phtaldehyde. Histamine levels, potentially the most toxic amine in hake, were very low during storage. The amine in hake with the highest level was cadaverine. Spermidine and putrescine had very high levels at the beginning of the storage. However, agmatine and tyramine were not detected in the source raw material. An increase in biogenic amines was observed in the control lot from day 12 of storage except for agmatine, where levels began to increase earlier. Cadaverine and agmatine could be used as control indices due to their behaviour during the storage period studied. The varying O₂ and CO₂ concentrations in the different atmospheres did not seem to affect the production of spermidine. The high levels of CO₂ in thelot in M1 atmosphere were not sufficient to inhibit the production of biogenic amines. However, the high O₂ concentration had an inhibiting effect on the production of biogenic amines. Therefore, the formation of biogenic amines was inhibited by controlled atmospheres with oxygen-enriched binary gas mixtures.     

Biogenic amine contents in fish and fish preserves

A method developed on the basis of highly efficient liquid chromatography of dansyl derivatives was used to study the content of biogenic amines (tyramine, histamine, cadaverine, putrescine, spermine and spermidine) in fish and canned fish. It was found that only 7 out of 149 samples contained histamine levels exceeding maximum permissible concentration (salted herring, smoked sardines, and salted Siberian salmon). No correlation was recorded between the increase of spermine content and spermidine.     

Application of the simplex method for optimization of chromatographic analysis of biogenic amines in fish

The aim of this study was to optimize the separation of biogenic amines with ion-exchange high-performance liquid chromatography, using the modified simplex method. A modified chromatographic response function was used, and two methodological parameters were selected as simplex variables: the proportion of the organic solvent 2-propanol in the mobile phases, added as a new mobile phase, and the variation of the gradient curve at one specific step in the elution program. In optimum conditions the correct resolution and separation of the biogenic amines (tyramine, β-phenylethylamine, histamine, tryptamine, putrescine, cadaverine, agmatine, spermidine and spermine) were completed in 16 min, reducing the analysis time by 9 min compared with the original method. The regression coefficients were higher than 0.99 in all the amines, except for spermine (0.989). The detection limits varied between 0.06 mg/L, for histamine and agmatine, and 0.22 mg/L, for tryptamine, while retention time repeatability, determined as a relative standard deviation, was between 4.64% for histamine and 11.95% for tryptamine. The repeatability variation for the amine concentrates was found between 0.71% in cadaverine and 3.23% for tryptamine. Applying the optimized method to samples of refrigerated sardine and sea bream demonstrated the effectiveness of the method in these fish species.     

高效液相色谱法检测牙鲆体内的生物胺

采用高效液相色谱(HPLC)法测定了牙鲆体内的多种生物胺.以邻苯二甲醛(OPA)为柱后荧光衍生剂,通过Capcell Pak MG C18色谱柱的梯度洗脱,将酪胺、腐胺、尸胺、组胺、胍丁胺、亚精胺和精胺等7种生物胺进行良好分离.测试结果表明,7种生物胺在0.05～30mg/L的范围内线性良好,相关系数都在0.999以上...     

Biogenic amines in restructured beef steaks as affected by added walnuts and cold storage

This article evaluates changes in biogenic amines and how these relate to microbiological growth in chilled, fresh restructured beef steaks containing transglutaminase as a cold binding agent and different amounts of walnut. Added walnut and chilling favored higher total and lactic acid bacteria counts during storage, whereas Enterobacteriaceae were not affected. The highest initial biogenic amine concentrations were identified as spermidine, spermine, and tyramine. Both added walnut and cold storage generally favored the formation of amines (tyramine, histamine, putrescine, and cadaverine), which was more obviously apparent by the end of the storage period. Agmatine, on the other hand, was not generally affected by the walnut.