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。     

Prerigor infusion of lamb with sodium chloride, phosphate, and dextrose solutions to improve tenderness

Various fermented and seasoned foods such as cheese, sauerkraut, wine, beer and meat products may contain biogenic amines. The aim of this paper was to describe the presence of some biogenic amines (histamine, tyramine, tryptamine, 2-phenylethylamine) in "Salamini italiani alla cacciatora PDO", a typical fermented-ripened dry sausage widely consumed in Italy. Total level of biogenic amines in commercial samples ranged from 71 to 586 mg kg(-1). The amine recovered in higher concentrations was tyramine (372 mg kg(-1)) followed by histamine (165 mg kg(-1)). The second aim of this work was the quality control of the production in order to determine the parameters influencing the presence of biogenic amines in ripened salami. Sausages sampled for analysis during production, manipulation and ripening showed the presence of tyramine (64.4 mg kg(-1)) only after 15 days of fermentation. All investigated biogenic amines were detected in "Salamini" after 21 days of fermentation. We suggest the control of biogenic as important tool to establish the better condition of preservation of "Salamini italiani alla cacciatore PDO" during their shelf-life.     

Salting-out assisted liquid–liquid extraction with dansyl chloride for the determination of biogenic amines in food

Biogenic amines (BAs) are compounds present in foodstuff of animal origin that not only can be harmful to the consumer but can also serve as indicators of the product's edibility status. However, BAs’ analysis is rather complicated. Derivatisation methods have been employed to make their analysis less challenging. Salting-out assisted liquid–liquid extraction (SALLE) was herein applied to decrease time that the derivatising agent dansyl chloride (DNS-Cl) requires to be effective. DNS-Cl derivates were separated and analysed by high-performance liquid chromatography with UV and fluorescence detection (HPLC-UV/FD). It was by this way possible to analyse methylamine, dimethylamine, ethylamine, β-phenylethylamine, isopentylamine, putrescine, cadaverine, histamine, tyramine, spermidine and spermine in a straightforward manner in several fish-based and meat-based samples, obtaining results in the order of magnitude of about a few mg per kg. All calibrations curves had r² higher than 0.99, and limits of detection ranged from 0.0075 to 1.6 mg L⁻¹.     

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).     

Occurrence of ochratoxin A and biogenic amines in Asian beers sold in French markets

Fifty‐one samples of 17 Asian beer brands commercially available in France were analysed for the occurrence of ochratoxin A and biogenic amines, including ethanolamine, histamine, methylamine, ethylamine, tyramine, tryptamine, 2‐phenylethylamine, putrescine, isopenthylamine and cadaverine. The types and levels of biogenic amines varied from one brand to another. None of the ochratoxin A or biogenic amine contaminants in the Asian beer samples exceeded the recommended levels for safe consumption. Ochratoxin A was found to range from n.d. to 0.175 µg L^?1. Biogenic amines were detected in all samples at a level ranging from 6.15 to 47.30 mg L^?1. Isoamylamine was not detected in any of the beers. Ethanolamine, tyramine, putrescine, and cadaverine were the most abundant of the nine biogenic amines found in this study. The concentrations were 2.75–12.88 mg L^?1 for ethanolamine, 0.58–17.37 mg L^?1 for tyramine, 1.54‐9.78 mg L^?1 for putrescine and 0.31–11.39 mg L^?1 for cadaverine. The work revealed significant, strong correlations (p < 0.01) between concentrations of ochratoxin A and biogenic amines, especially tyramine, tryptamine and cadaverine. Copyright © 2013 The Institute of Brewing & Distilling     

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。     

Levels of histamine and other biogenic amines in high-quality red wines

Biogenic amines in wine may impair sensory wine quality and cause adverse health effects in susceptible individuals. In this study, histamine and other biogenic amines were determined by HPLC after amine derivatisation to dansyl chloride conjugates in 100 selected high-quality red wines made from seven different cultivars. Amine levels varied considerably between different wines. The most abundant amines were putrescine (median?=?19.4?mg?l^?1, range?=?2.9–122), histamine (7.2?mg?l^?1, 0.5–26.9), and tyramine (3.5?mg?l^?1, 1.1–10.7), whereas lower levels were found for isoamylamine (median?=?0.25?mg?l^?1), phenylethylamine (0.16?mg?l^?1), cadaverine (0.58?mg?l^?1), spermidine (1.8?mg?l^?1) and tryptamine (0.06?mg?l^?1). Positive correlations were observed between isoamylamine and phenylethylamine, and between histamine, putrescine and tyramine levels. Amine concentrations were similar in all wine cultivars except Pinot noir and St. Laurent wines, which showed significantly higher tryptamine and cadaverine levels. The results indicate that levels of histamine and other biogenic amines may vary considerably between red wines independent of grape variety and that high amounts can also be found in high-rated wines. Adopting a legal histamine threshold level of 10?mg?l^?1 in the European Union, as formerly introduced in other countries, would have excluded 34% of the investigated wines from the market.     

UPLC-MS/MS法测定黄酒中8 种生物胺

建立黄酒中组胺、酪胺、腐胺、色胺、β-苯乙胺、尸胺、精胺、亚精胺共8?种生物胺的超高效液相色谱-串联质谱检测方法。样品衍生化处理后,经C18色谱柱（100.0?mm×2.1?mm,1.7?μm）分离,0.1%甲酸溶液、0.1%甲酸-乙腈溶液作为流动相梯度洗脱,用多反应监测模式下的电喷雾正离子扫描获得质谱数据,并采用内标法进行定量。结果表明：8?种生物胺可在19?min内分离,且在各自质量浓度范围内线性良好,r2均大于0.995?1;检出限为0.25～0.50?ng/mL,定量限为1～2?ng/mL,日内精密度为0.61%～5.68%,日间精密度为0.82%～5.00%;黄酒样品中生物胺的加标回收率在83.56%～117.45%之间,相对标准偏差均低于6.69%。     

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。     

Biogenic amines profile and concentration in commercial milks for infants and young children

Commercial milks for infants and young children (CMIYC) received much attention during last years for their impact on the nutritional status, health and development of the new-born and babies. Among possible contaminants contained in these foods, biogenic amines (BAs) have rarely been determined although they can exert toxic effects in humans if ingested at high concentrations. Spermine, spermidine, putrescine, histamine, tyramine, β-phenylethylamine and cadaverine have been quantified in CMIYC samples by LC-UV after derivatisation with dansyl-chloride. Once optimised in terms of linearity (R² ≥ 0.989), recovery percentages (92.9–97.3), LOD (0.2–0.4 μg g^?1 or 0.03–0.05 μg mL^?1 depending on the samples), LOQ (0.5–1.0 μg g^?1 and 0.08–0.13 μg mL^?1 depending on the samples) and repeatability (0.1–0.2 intra-day; 0.2–0.4 inter-day), the method has been applied to real samples. Very low total BAs concentrations have been found in reconstituted (1.18–3.12 mg L^?1) and liquid milks (0.33–2.30 mg L^?1), with different biogenic amine profiles and distributions. A risk assessment based on the available information regarding Acute Reference Doses of histamine and tyramine, as well as the application of common Biogenic Amine Indexes, showed that none of the analysed samples represented a possible risk for babies, also considering a worst case evaluation. These findings confirmed the strict safety and quality protocols adopted during the production of CMIYC.

Chemical compounds studied in this article: Ammonium chloride (PubChem CID: 25517); Cadaverine hydrochloride (PubChem CID: 5351467); Hydrochloridric acid (PubChem CID: 313); Histamine dihydrochloride (PubChem CID: 5818); Phenylethylamine hydrochloride (PubChem CID: 9075); Putrescine dihydrochloride (PubChem CID: 9532); Sodium hydroxide (PubChem CID: 14798); Spermine tetrahydrochloride (PubChem CID: 1103); Spermidine trihydrochloride (PubChem CID: 1102); Tyramine hydrochloride (PubChem CID: 66449).     

Determination of biogenic amine profiles in conventional and organic cocoa-based products

Cocoa contains many compounds such as biogenic amines (BAs), known to influence consumer health. Spermidine, spermidine, putrescine, histamine, tyramine, β-phenylethylamine, cadaverine and serotonine have been found in several cocoa-based products using HPLC with UV detection after derivatisation with dansyl-chloride. Once optimised in terms of linearity, percentage recovery, LOD, LOQ and repeatability, this method was applied to real samples. Total concentrations of BAs ranged from 5.7 to 79.0 µg g^?1 with wide variations depending on the type of sample. BAs present in all samples were in decreasing order: histamine (1.9–38.1 µg g^?1) and tyramine (1.7–31.7 µg g^?1), while putrescine (0.9–32.7 µg g^?1), spermidine (1.0–9.7 µg g^?1) and spermidine (0.6–9.3 µg g^?1) were present in most of the samples. Cadaverine, serotonine and β-phenylethylamine were present in a few samples at much lower concentrations. Organic samples always contained much lower levels of BAs than their conventional counterparts and, generally speaking, the highest amounts of BAs were found in the most processed products.     

Method development and cultivar-related differences of nine biogenic amines in Ontario wines

We have developed a new high-performance liquid chromatographic method using pre-column derivatization with orthophthalaldehyde, gradient elution and fluorescence detection to assay the concentrations of nine biogenic amines in wines: histamine, 1-methylhistamine, methylamine, ethylamine, tyramine, tryptamine, 2-phenylethylamine, putrescine and cadaverine. The method shows excellent analytical characteristics. It has been used to measure the concentration of these biogenic amines in 73 monovarietal wines from five red and six white cultivars. All wines were from the Niagara viticultural region of southern Ontario and were certified as to origin. Pinot noir wines had the highest content of total amines, and also of histamine, putrescine, cadaverine, ethylamine and 1-methylhistamine. Among the white wines, those from Chardonnay had the highest content of total amines and also of histamine, tyramine, methylamine and 1-methylhistamine. It is suggested that longer ageing as well as Sur-lie fermentation (Chardonnay) can account, at least in part, for these findings.     

Biogenic amine production by Oenococcus oeni during malolactic fermentation of wines obtained using different strains of Saccharomyces cerevisiae

Twenty-six wild Oenococcus oeni strains were investigated for their ability to form biogenic amines during malolactic fermentation in synthetic medium and in wine. Eight strains produced histamine and tyramine in screening broth at concentrations of 2.6-5.6 mg/L and 1.2-5.3 mg/L, respectively. Based on their ability to form biogenic amines, five strains were selected to inoculate three wines obtained by the fermentation of three different Saccharomyces cerevisiae strains (A, B, and C). All bacterial strains could perform malolactic fermentation for short periods in wine C, whereas only one strain performed complete malolactic fermentation in wines A and B. Two O. oeni strains (261 and 351) produced histamine and tyramine in wine C. Time-course analysis of these compounds showed that for both strains, histamine and tyramine production began at day 10 and finished on day 25, after the end of malolactic fermentation. These results indicate that the ability of O. oeni to produce histamine and tyramine is dependent on the bacterial strain and on the wine composition, which in turn depends on the yeast strain used for fermentation, and on the length of bacteria-yeast contact time after the completion of malolactic fermentation.     

Application of LC with Evaporative Light Scattering Detector for Biogenic Amines Determination in Fair Trade Cocoa-Based Products

In this study, the separation of eight biogenic amines (cadaverine, serotonin, histamine, spermidine, spermine, tyramine, putrescine and β-phenylethylamine) by a liquid chromatography (LC) method with evaporative light scattering detection (ELSD) was performed. The LC–ELSD method was validated by comparison of the results with those obtained through LC–ultraviolet (UV) determination, based on a pre-column dansyl chloride derivatisation step, and the recorded data showed as both analytical methods can be interchangeably used for biogenic amines determination. LC–ELSD methodology showed good precision and permitted to achieve, for standard solutions, limits of detection (LOD) ranging from 0.01 to 0.02 μg ml^?1 and limits of quantitation (LOQ) ranging from 0.03 to 0.05 μg ml^?1. The whole methodology, comprehensive of the homogenization–extraction process and LC–ELSD analysis, has been applied in the analysis of several samples of fair trade cocoa derivatives. The most abundant amine found was histamine for a total amount of biogenic amines in the range 5.81–38.82 μg g^?1. The highest amounts of biogenic amines (BAs) were found in the most processed products but never representing a possible risk for consumer health, according to the toxicity levels reported in literature and regarded as acceptable.     

复合香辛料提取物对哈尔滨风干肠中生物胺形成的抑制作用

研究复合香辛料提取物（肉桂、丁香和八角按质量比1∶1∶1混合）不同添加量（0.1、0.3、0.5 g/kg）对哈 尔滨风干肠发酵过程中生物胺形成的抑制作用,以及对风干肠理化指标、微生物指标和感官品质的影响。结果表 明,复合香辛料提取物可以有效抑制生物胺（酪胺、腐胺、尸胺、组胺、2-苯乙胺和色胺）的积累（P＜0.05）, 减少脂肪氧化产物硫代巴比妥酸值并抑制好氧菌的生长,且抑制效果随添加量的增加而增大（P＜0.05）。但是添 加0.5 g/kg复合香辛料提取物会产生过重的香辛料气味,影响产品感官可接受性。风干肠中复合香辛料提取物添加 量为0.3 g/kg时,可有效抑制产品中生物胺积累,且可改善产品的感官品质。     

Biogenic amines in alcoholic beverages produced in Taiwan

The biogenic amines tyramine, putrescine, cadaverine, 2-phenylethylamine, histamine and tryptamine were determined in 13 kinds of alcoholic beverages produced in Taiwan. They were derivatised with dansyl chloride and analysed using a high-performance liquid chromatographic method. Total amine content ranged from 0.23 to 11.4 μg ml^?1 with Charng Chuen liqueur containing the highest level and Mei Kwei Lu the lowest. Tryptamine was found in all samples in amounts between 0.01 and 1.79 μg ml^?1. The levels of the other five amines in the tested samples were 0-7.0 μg ml^?1 for 2-phenylethylamine, 0-3.0 μg ml^?1 for putrescine, 0-2.9 μg ml^?1 for cadaverine, 0-4.5 μg ml^?1 for histamine, and 0-1.4 μg ml^?1 for tyramine. These levels seem unlikely to have adverse effects on human health.     

A comparative study for determination of biogenic amines in meat samples by capillary isotachophoresis with two electrolyte systems

The selected biogenic amines, BAs (putrescine, cadaverine, histamine, tyramine, spermidine and spermine), in pork, beef, and poultry meat samples were determined by two simple procedures without derivatization using isotachophoretic technique. Two electrolyte systems were proposed for their separation and determination with satisfactory separation parameters. The linearity of the proposed procedures was between 2–10 mg L^?1 and 5–50 or 10–60 mg L^?1, whereas average recoveries for the standard solutions of amines and their mixture varied between 99–100 % and 95–105 %, respectively. Average recoveries for standard addition method (96–99 %) indicated satisfactory accuracy of proposed electrolyte systems. The obtained coefficient of variation values for standard solutions and meat samples ranged from 0.62 to 4.54 % and from 0.56 to 6.03 %, respectively, which confirmed good repeatability. Except for spermidine and spermine, BAs levels in fresh meat samples were generally low. The effect of storage time on the content of biogenic amines in meat was also studied indicating the increase of BAs levels (excluding Spermine and Spermidine).     

Biogenic amines in commercially produced Yulu,a Chinese fermented fish sauce

Seven biogenic amines were determined in 35 commercially produced Yulu samples from three provinces of China by pre-column derivatisation with dansyl chloride (Dns-Cl) and high-performance liquid chromatography with fluorescence detection (HPLC-FLD). Putrescine, cadaverine, histamine and tyramine were the major biogenic amines (more than 100 mg kg^?1), while tryptamine, spermidine and spermine were regarded as minor biogenic amines (less than 25 mg kg^?1). Twenty samples contained more than 50 mg kg^?1 histamine (the limit for histamine in seafood products as suggested by the Food and Drug Administration). Twenty-one samples contained more than 100 mg kg^?1 tyramine and 10 contained more than 1000 mg kg^?1 total biogenic amines. This study provided data on biogenic amine levels in Chinese fermented fish sauce. The results suggested that biogenic amine content should be monitored in commercially produced Yulu.     

Effects of heat treatment and storage temperature on the biogenic amine content of straw mushroom (Volvariella volvacea)

The changes in the biogenic amines tryptamine, 2-phenylethylamine, putrescine, cadaverine, histamine and tyramine of straw mushroom Volvariella volvacea (Bull, ex Fr) Sing produced by heat treatment and during storage at different temperatures were studied. About 80% of the original content of these amines was lost during cooking. Commercial canned straw mushroom contained low amounts of amines. The amine contents of straw mushroom increased during storage at 4°C, with particularly notable increases in the concentrations of 2-phenylethylamine and tyramine after 5 days' storage. However, the levels of all amines increased more markedly during storage at 25°C, and the increases in the putrescine and cadaverine concentrations were much greater than those reached at 4°C.     

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.