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。     

Determination of biogenic amines in Japanese miso products

Eight miso products sold in supermarket were purchased from Japan and analyzed for the determination of biogenic amines (BAs). Quantitative determination of BAs in miso products was carried out by means of HPLC with spectrophotometric UV-VIS detector. The amines were extracted in acid aqueous solution (HClO₄) and then derivatized by dansyl chloride. The levels of pH in the tested miso samples were ranged from 4.8–5.5. The BAs (tryptamine, 2-phenyl ethylamine, putrescine, cadaverine, agmatine, tyramine, and spermidine) determined in 8 miso samples were found in their respective range of ND-0.13, ND-4.20, ND-1.29, ND-0.87, ND-0.90, ND-4.19, and ND-3.57 mg%. None of the miso samples contained histamine and spermine, the major BAs of food poisoning.     

Relation of biogenic amines with microbial and sensory changes of whole and filleted freshwater rainbow trout (Onchorynchus mykiss) stored on ice

The biogenic amine (BA) content of whole and filleted rainbow trout was monitored during ice storage for a period of 18 days and related to respective microbial and sensorial changes occurring during the same period. Eight amines, namely, putrescine, cadaverine, tyramine, spermidine, tryptamine, beta-phenylethylamine, spermine, and histamine, were determined. Agmatine was not detected in any of the fish samples. In all cases, concentration of BAs was higher (P < 0.05) in filleted compared with whole trout samples. Pseudomonads, H2S-producing bacteria, and, to a lesser extent, Enterobacteriaceae were the dominant microorganisms in both whole and filleted trout. Higher populations (P < 0.05) of these microorganisms were present in filleted trout compared with whole fish samples. Of the BAs determined, concentration of putrescine, cadaverine, spermidine, tryptamine, and beta-phenylethylamine increased steeply in both whole and filleted trout between days 15 and 18 of storage when pseudomonads and H2S-producing bacteria reached approximately 10(6) to 10(7) CFU/g. For the rest of the BAs, including tyramine, histamine, and spermine, a stepwise increase was recorded throughout the entire storage period. Interestingly, Enterobacteriaceae counts remained below 10(6) throughout the entire storage period, accounting for the lower production of histamine. A putrescine value of 13 to 14 mg/kg and a spermidine value of approximately 7 mg/kg for both the whole and filleted trout obtained after 12 and 9 days, respectively, may be proposed as the upper limit for spoilage initiation (freshness indicator) of fresh rainbow trout based on sensorial and microbiological (total viable count of 10(6) to 10(7)) data. With respect to other amines determined, both tyramine and spermine may also be proposed as freshness indicators preferably for whole trout, whereas tryptamine, beta-phenylethylamine, histamine, and cadaverine produced only during later stages of storage are not suitable as freshness indicators of either whole or filleted trout.     

Determination of biogenic amines in traditional Chinese fermented foods by reversed-phase high-performance liquid chromatography (RP-HPLC)

A survey of biogenic amine content of traditional Chinese fermented foods (douchi, sufu, fermented sausage, yulu, and shrimp paste) was carried out. Eight major biogenic amines including putrescine, cadaverine, histamine, phenylethylamine, tyramine, spermine, spermidine and tryptamine were separated by reversed-phase HPLC-DAD on Inertsil ODS-SP column after pre-column derivatisation with dansyl chloride. The results showed that spermine (1.65–3.96 mg 100 g^?1), putrescine (0.20–10.89 mg 100 g^?1), cadaverine (3.60–12.14 mg 100 g^?1), and histamine (0.57–20.24 mg 100 g^?1) were the most represented amines. All amines were detected in yulu, while sufu showed a much higher content of most amines. Shrimp paste showed the lowest level of total biogenic amines. Moreover, the composition and content of eight biogenic amines in the selected samples varied among different food types, origins and batches. Although the average content for each amine is within the range that may elicit direct adverse reactions, consumers should be aware of the potential synergistic effect among different amines and limit their consumption at each meal.     

A review of the liquid chromatographic methods for the determination of biogenic amines in foods

Biogenic amines (BAs) are biologically active molecules which have aliphatic (putrescine, cadaverine, spermine, spermidine), aromatic (tyramine, phenylethylamine) or heterocyclic (histamine, tryptamine) structures. They can be detected in raw and processed foods which are formed and degraded through several pathways during the metabolic processes of animals, plants and microorganisms. The identification and quantitation procedures of BAs in food samples are very important, because BAs are considered as the indicators of food quality and freshness. The determination of BAs are commonly achieved by separation techniques such as high-performance liquid chromatography (HPLC), gas chromatography (GC) and capillary electrophoresis (CE). In this article, analysis of BAs in foods were reviewed from 2007 to present.     

利用高效液相色谱法测定不同发酵时长郫县豆瓣酱中的8种生物胺

本研究基于高效液相色谱(HPLC)技术,测定了不同发酵时长(1~96个月)郫县豆瓣酱中色胺、β-苯乙胺、腐胺、尸胺、组胺、酪胺、亚精胺和精胺8种生物胺的含量。结果显示,HPLC分析中,8种生物胺的检出限在0.17~0.35 mg/L之间,定量限在0.55~0.92 mg/L之间,各生物胺标品在1~60 mg/L的质量浓度范围内线性关系良好,可被准确定量;各生物胺回收率在73.10%~104.13%之间,说明本方法具有较高的重复性和灵敏度。腐胺、尸胺、酪胺和组胺是郫县豆瓣酱中的主要生物胺;随着发酵时间的延长,腐胺含量快速上升,尸胺含量在发酵前54个月迅速上升,之后明显下降,酪胺和组胺在发酵54个月后含量有所增加;其他生物胺含量较低,且发酵期间变化不明显;郫县豆瓣酱中总生物胺含量随发酵时间的延长不断积累,从(37.86±6.69) mg/kg增加到(155.09±8.53) mg/kg,其含量在发酵前54个月快速上升,之后趋于稳定。目前食品中的多数生物胺尚没有限量标准,但参考现有的毒理学数据来看,本研究中郫县豆瓣酱的生物胺含量水平相对安全。     

Effect of low-dose irradiation on biogenic amines formation in vacuum-packed trout flesh (Oncorhynchus mykiss)

The effects of vacuum packaging followed by high-energy electron beam irradiation on the shelf-life of fillets of rainbow trout (Oncorhynchus mykiss) were examined. Samples were irradiated at doses of 0.25, 0.50, 0.75, 1.0 and 2.0 kGy. The control and treated packs were stored at 3.5 °C for up to 28, 42, 70 and 98 days (control - 0, 0.25, 0.50 and >0.50 kGy respectively). The content of seven biogenic amines (putrescine, cadaverine, spermidine, spermine, histamine, tyramine and tryptamine) were determined. Putrescine, cadaverine and tyramine showed very good correspondence with the irradiation dose and organoleptic properties. Samples of good quality contained less than 10 mg/kg of each of these amines. The polyamines spermidine and spermine did not show statistically significant changes with the irradiation dose and the time of storage. With few exceptions, histamine was not detected in the samples treated with radiation. Tryptamine was not detected in any of the samples.     

Monitoring of biogenic amines in cheeses manufactured at small-scale farms and in fermented dairy products in the Czech Republic

The aim of the study was the monitoring of six biogenic amines (histamine, tyramine, phenylethylamine, tryptamine, putrescine, and cadaverine) and two polyamines (spermidine and spermine) in 112 samples of dairy products purchased in the Czech Republic, namely in 55 cheeses made in small-scale farms and in 57 fermented dairy products. The products were tested at the end of their shelf-life period. Neither tryptamine nor phenylethylamine was detected in the monitored samples; histamine was found only in four cheese samples containing up to 25 mg/kg. The contents of spermine and spermidine were low and did not exceed the values of 35 mg/kg. Significant amounts of tyramine, putrescine, and cadaverine occurred especially in cheeses produced from ewe’s milk or in long-term ripened cheeses. In about 10% of the tested cheeses, the total concentration of all the monitored biogenic amines and polyamines exceeded the level of 200 mg/kg, which can be considered toxicologically significant. In fermented dairy products, the tested biogenic amines occurred in relatively low amounts (generally up to 30 mg/kg) that are regarded safe for the consumer’s health.     

Variation in content of tyramine,histamine, 2-phenylethylamine,tryptamine and their precursor amino acids in a Chardonnay wine by using different commercial active dry yeasts and nitrogen sources

Wine is a fermented beverage that could be affected by high concentrations of biogenic amines, thus altering organoleptic and health properties. In this work, the capacity of different selected yeast strains regarding to affect the content of tyramine, histamine, 2-phenylethylamine, tryptamine and their precursor amino acids (pAA) during fermentation has been described. Overall, biogenic amines (BAs) and pAA contents appeared significantly related both to the strain and to the nutrient supplementation applied. Among BAs, without and (with) nitrogen source addition, the concentrations covered a range between 0.1 and 9.5 (0.1–10.3) mg L⁻¹ for tyramine; 0.1 and 4.4 (0.1–4.6) mg L⁻¹ for histamine; 0.4 and 1.1 (0.4–1.4) mg L⁻¹ for 2-phenylethylamine; and 0.02 and 0.14 (0.01–0.12) mg L⁻¹ for tryptamine, respectively. Considering that also wine yeast species are responsible for BAs formation, the evidence from fermentation trials underlined the relevance of a careful choice of ADY strains and nitrogen sources in the management of alcoholic fermentation in wine.     

Effects of gamma irradiation on the biogenic amines in pepperoni with different packaging conditions

Combined effects of gamma irradiation and packaging on biogenic amine (BA) formation in pepperoni sausage were investigated during storage. Pepperoni (fermented sausage) was made and packaged with air, vacuum and CO₂/N₂ (25%/75%) gas and then gamma-irradiated at 0, 5, 10 and 20 kGy. The pH was decreased after storage and non-irradiated samples showed a lower pH than irradiated. Lactic acid bacteria (LAB) were not detected after 5 kGy of gamma irradiation, while the LAB in the non-irradiated samples were 4–5 log counts during storage. A total of six different BAs, putrescine, cadaverine, β-phenylethylamine, spermidine, spermine and tyramine, were found in the pepperoni sausage. Detected BAs were statistically low under the irradiation or packaging conditions, except for cadaverine and β-phenylethylamine. Gamma irradiation was effective in reducing putrescine, spermidine, spermine and tyramine. Irradiation effects were not observed on the β-phenylethylamine level, while the CO₂/N₂ packaging caused increasing of the level. Most BAs detected were reduced by gamma irradiation of the pepperoni sausage during storage. However, CO₂/N₂ packaging was an improper condition for BA reduction in the pepperoni sausage.     

Determination of biogenic amines in <Emphasis Type="Italic">Cheonggukjang</Emphasis> using ultra high pressure liquid chromatography coupled with mass spectrometry

A rapid and reliable method for the simultaneous determination of 12 biogenic amines (BAs; agmatine, phenylethylamine, tyramine, putrescine, cadaverine, histamine, serotonin, tryptamine, spermidine, noreinephrine, dopamine, and spermine) in cheonggukjang was optimized and validated using ultra high pressure liquid chromatography-electrospray tandem mass spectrometry (UHPLC-ESI-MS/MS). The BAs were dansylated and separated on a C8 column under LC gradient of 7 min duration, and detected by MS/MS with the multiple reaction monitoring mode (MRM). This method exhibited excellent linearity for all of the analytes with correlation determination (R²) higher than 0.98. The limits of detection (LODs) were 10.8–39.6 μg/kg. The precision results were expressed as relative standard deviation (RSD), ranged from 0.3 to 14.3% for intra-day and from 0.9 to 15.4% for the interday. The proposed method will help to ensure for quality control by monitoring of BAs in cheonggukjang.     

新疆赤霞珠葡萄酒发酵过程中生物胺含量的变化

利用高效液相色谱技术分析葡萄酒发酵过程中8种生物胺含量的变化。结果表明,葡萄酒发酵过程中8种生物胺总含量整体呈上升趋势。色胺含量最高,最高可达到98.03 mg/L;腐胺和组胺含量较低,含量均不超过2.48 mg/L;精胺和亚精胺含量变化相对平稳,波动范围在1.81～3.07 mg/L之间,除色胺外,其他生物胺含量均不超过4.50 mg/L。苯乙胺、尸胺、酪胺等在酒精发酵后期和苹果酸-乳酸发酵初期大幅上升,在苹-乳发酵后期,酪胺和亚精胺含量有所下降,其他生物胺含量均有一定程度上升。     

减盐对东北农家酱中生物胺形成的影响

目的:研究减盐对东北农家酱中生物胺形成的影响.方法:对正常食盐添加量与减盐条件(在正常食盐添加量的基础上分别减少10％、20％、30％、40％)下的东北农家酱中总胺与8种生物胺(精胺、腐胺、色胺、苯乙胺、尸胺、组胺、酪胺、亚精胺)的含量进行分析,相应地对理化指标(氨基酸态氮、总酸含量)、微生物指标(菌落总数)进行分析,...     

Detection of ten biogenic amines in Chinese commercial soybean paste by HPLC

This paper aimed to develop a high-performance liquid chromatography (HPLC) method that can simultaneously detect ten biogenic amines (BAs) in commercially available soybean paste and to determine the contents of BAs in these products. Heptylamine (Hep) was used as the internal standard reagent and benzoyl chloride as the sample derivatization reagent; Inertsil ODS-3 chromatographic column was set as the stationary phase while the acetonitrile and 5 mmol/L ammonium acetate solution as the mobile phases; the samples were treated with gradient elution and detected at 254 nm (UV). Perchloric acid solution (0.4 mol/L) was employed as the sample extraction solvent to determine the contents of ten BAs in soybean paste products. All BAs were separated within 20 min. The methodological validation suggested good linearity, whereas the linear correlation coefficient of all standards was greater than 0.99 with the linear range of 0.1–80 μg/g, detection limits of 0.01–0.03 μg/g, and quantitation limits of 0.03–0.10 μg/g. For 17 commercially available soybean paste products involved in our study, different samples were distinguished from each other not only by the dramatic differences in the contents of BAs but also by the variance in BA types. Of these BAs, tyramine (Tyr) and agmatine (Agm) were found to be the highest contents in soybean paste products; the contents of histamine (His), 2-phenylethylamine (Phe), serotonin (Ser), spermidine (Spd), and putrescine (Put) were lower, followed by cadaverine (Cad), tryptamine (Try), and spermine (Spm). This method proved to be highly sensitive and effective in determining the contents of BAs in soybean paste products; there was a dramatic difference in the contents of ten BAs among different soybean paste products.     

Biogenic amines in selected foods of animal origin obtained from the Croatian retail market

ABSTRACT

This study aimed to investigate the presence of eight biogenic amines (BAs): tryptamine (TRP), phenylethylamine (PHE), putrescine (PUT), cadaverine (CAD), histamine (HIS), tyramine (TYR), spermidine (SPD) and spermine (SPM) in cheese, fish & fishery products and meat & meat products obtained from the Croatian retail market. A selective and robust method of high-performance liquid chromatography (HPLC) with diode array detection (DAD) was applied for the determination of BAs in a total of 91 samples in accordance with the performance criteria outlined in the European legislation. A high inter- and intra-food group variability of the amounts of BAs was observed. In the analysed samples, the most represented amines were TYR, HIS, CAD and PUT. Based on the highest content of the most toxic BAs (HIS and TYR) and consequential food safety concerns, the studied food groups can be ranked in the following order: cheese (HIS up to 106.4 mg/kg; TYR up to 206.6 mg/kg), fish &fishery products (HIS up to 98.8 mg/kg; TYR up to 47.9 mg/kg), and meat & meat products (HIS up to 20.0 mg/kg; TYR up to 117.5 mg/kg). The total BA content was significantly higher (p < .05) in fermented in comparison with other food. The study aimed to contribute to the knowledge on BA toxicity and food quality, as well as to support the indispensable future studies of consumption data and exposure assessment, to the end of defining allowable BA concentrations in food.     

四川区域自然发酵香肠及人工接种牦牛肉发酵香肠中生物胺含量的研究

以四川省10 区域自然发酵香肠及人工接种发酵剂的牦牛肉香肠共21 个样品为研究对象,测定发酵香肠中的生物胺含量。结果发现,21 个发酵香肠样品中均检测到酪胺、亚精胺、精胺、尸胺、腐胺、色胺及组胺,β-苯乙胺均未检出;生物胺总量在57.34～411.12 mg/kg,除采自凉山州西昌的自然发酵牦牛肉香肠和广安的自然发酵猪肉香肠中酪胺含量超过了美国食品及药品管理局（Food and Drug Administration,FDA）规定标准（酪胺含量≤100 mg/kg）,其余均不存在生物胺安全问题。     

FORMATIONS OF BIOGENIC AMINES IN TURKISH STYLE SAUSAGE DURING RIPENING AND STORAGE PERIODS

Changes of biogenic amine (histamine, β‐phenylethylamine, serotonin, spermine, spermidine, cadaverine, putresine, 1,7‐diamino heptane, tryptamine and tyramine) concentrations and pH values of Turkish style sausages were investigated during ripening and storage. Cadaverine and β‐phenylethylamine were not detected during the ripening and storage periods for all sausage types. Storage time had a significant (P<0.05) effect on the formation of all biogenic amines. Starter culture usage decreased (P<0.05) biogenic amine formation. Histamine levels were higher in sausages prepared without additives and lower in the sausages made with starter culture than the sausages made without starter culture. There was no effect of starter culture and additives on formation of tryptamine, 1,7‐diamino heptane, serotonin or spermidine. Starter culture and additives affected (P<0.05) the formation histamine, putrescine and spermine. pH values of sausages sharply decreased (P< 0.05) from 5.98 to about 4.53 during 3 days of ripening. After that, pH values increased slowly and were nearly constant during the storage period.     

Analysis of Vacuum Packed Beef Regarding Psychrotrophic Bacteria Growth and Biogenic Amines Content

It has been recognized that biogenic amines (BA) content in meat can be considered a freshness marker. Considerable amounts of some BAs can appear during food storage under certain conditions, according to the handling of the raw material, technology applied, storage temperature and time, packaging condition, mainly if amino acid - decarboxylase positive microorganisms are present. The aim of this study was to evaluate the psychrotrophic bacteria growth and metabolic production of BAs during chill storage of beef. The vacuum packed beef cuts (Longissimus dorsi muscle) were analyzed during storage at 7 °C at 0, 15, 30, 45, and 60 d, to determine the psychrotrophic bacteria growth and the BAs amount. The BAs considered were: putrescine, cadaverine, histamine, spermidine, and spermine. The BAs quantitative determination was carried out by reversed phase high-performance liquid chromatography (HPLC) with UV detection. Statistic procedures were performed using SAS statistical software. The growth parameters of psychrotrophic bacteria including lag phase, maximum specific growth rate, maximum bacterial cell density, initial population, mean square error, and coefficient of determination were determined according to Baranyi and Roberts model. The values of histamine and spermidine increased significantly (P < 0.0001) during storage time, while the levels of spermine decreased (P < 0.0001). Psychrotrophic bacteria counts increased significantly (P < 0.0001) reaching 7.6 log cfu/g over time. The counts of this group positively correlated to histamine and spermidine (r = 0.68 and 0.61, respectively), while spermine showed a negative correlation (r = -0.70). Conversely, no significant correlation was found between psychrotrophics counts and putrescine or psychrotrophics counts and cadaverine.     

豆豉中生物胺含量的动态变化研究

采用高效液相色谱法对豆豉中生物胺含量进行动态检测。结果表明,纯种强化发酵和自然发酵豆豉样品中均检测出色胺、苯乙胺、腐胺、尸胺、组胺、酪胺、亚精胺和精胺。纯种强化发酵条件下生物胺总含量在前、后发酵时期都呈先上升后下降的趋势,而自然发酵条件下均呈缓慢上升趋势,且前发酵总生物胺含量高于后发酵时期。两种发酵条件下,酪胺和亚精胺为主要生物胺,苯乙胺存在纯种发酵中。纯种强化发酵豆豉总生物胺含量高于自然发酵,酪胺和苯乙胺的含量分别高出2倍和4倍,与生产环境中粪肠球菌的污染关联性较大。豆豉发酵过程和成品中总生物胺含量均＜250 mg/kg,短期内不存在食品安全问题。     

Effect of proteolytic starter cultures of Staphylococcus spp. on biogenic amine formation during the ripening of dry fermented sausages

The effect of proteolytic starter cultures of Staphylococcus carnosus and Staphylococcus xylosus on biogenic amine production was examined during the fermentation process of dry sausages. Microbial counts (lactic acid bacteria, Micrococcaceae and Enterobactenaceae), pH, moisture and proteolysis-related parameters were also studied. The polyamines spermine and spermidine were the main amines found in the raw material and they only showed slight fluctuations during the fermentation. The four elaborated batches presented a significant (P < 0.001) formation of tyramine and putrescine. The main rate of amine production was during the first three days, when a sharp pH decrease and the development of lactic acid bacteria occurred. Sausages fermented with starters had lower amounts of tyramine than naturally fermented sausages (control), but differences in the Micrococcaceae counts were only significant during the first week of the ripening process. A slight formation of diaminopropane, cadaverine, agmatine, tryptamine and phenylethylamine was observed. The amounts of histamine were constant and remained below 0.5 mg/kg of dry matter, while serotonin, octopamine and dopamine were not detected. The sausages with Staphylococcus as starter culture showed strong proteolysis that was correlated with higher pH values than those of the control sausages. However, no positive correlation was found between the proteolysis index and biogenic amine production. Since proteolysis was stronger during the second half of the ripening process, the release of free amino acids as amine precursors occurred later than the early amine production.