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1.
Acrylamide levels in cooked/processed food can be reduced by treatment with citric acid or glycine. In a potato model system cooked at 180 degrees C for 10-60 min, these treatments affected the volatile profiles. Strecker aldehydes and alkylpyrazines, key flavor compounds of cooked potato, were monitored. Citric acid limited the generation of volatiles, particularly the alkylpyrazines. Glycine increased the total volatile yield by promoting the formation of certain alkylpyrazines, namely, 2,3-dimethylpyrazine, trimethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, tetramethylpyrazine, and 2,5-diethyl-3-methylpyrazine. However, the formation of other pyrazines and Strecker aldehydes was suppressed. It was proposed that the opposing effects of these treatments on total volatile yield may be used to best advantage by employing a combined treatment at lower concentrations, especially as both treatments were found to have an additive effect in reducing acrylamide. This would minimize the impact on flavor but still achieve the desired reduction in acrylamide levels.  相似文献   

2.
The chemical reactivity of 5-(hydroxymethyl)-2-furaldehyde (HMF) with lysine, glycine, and proline was studied using isotope labeling technique. To confirm the formation of HMF adducts in glucose amino acid model systems, a useful strategy was developed in which products simultaneously possessing six glucose (HMF moiety) and any number of amino acid carbon atoms in addition to nitrogen were targeted using specifically labeled precursors such as [(15)N(α)]lysine·2HCl, [(15)N(ε)]lysine·2HCl, [U-(13)C(6)]lysine·2HCl, [(13)C(6)]lysine·2HCl, and [U-(13)C(6)]glucose in the case of lysine model system. In addition, model systems containing HMF and amino acids were also studied to confirm specific adduct formation. Complete labeling studies along with structural analysis using appropriate synthetic precursors such as HMF Schiff base adducts of piperidine and glycine have indicated that HMF generated in the glucose/amino acid model systems initially forms a Schiff base adduct that can undergo decarboxylation through an oxazolidin-5-one intermediate and form two isomeric decarboxylated Schiff bases. Unlike the Schiff bases resulting from primary amines or amino acids such as glycine or lysine, those resulting from secondary amino acids such as proline or secondary amines such as piperidine can further undergo vinylogous Amadori rearrangement, forming N-substituted 5-(aminomethyl)furan-2-carbaldehyde derivatives.  相似文献   

3.
Investigations of different sources of acrylamide formation in model systems consisting of amino acids and sugars have indicated the presence of two pathways of acrylamide generation; the main pathway specifically involves asparagine to directly produce acrylamide after a sugar-assisted decarboxylation step, and the second, nonspecific pathway involves the initial formation of acrylic acid from different sources and its subsequent interaction with ammonia and/or amines to produce acrylamide or its N-alkylated derivatives. Aspartic acid, beta-alanine, and carnosine were found to follow the acrylic acid pathway. Labeling studies using [(13)C-4]aspartic acid have confirmed the occurrence in this amino acid of a previously proposed sugar-assisted decarboxylation mechanism identified in the asparagine/glucose model system. In addition, creatine was found to be a good source of methylamine in model systems and was responsible for the formation of N-methylacrylamide through the acrylic acid pathway. Labeling studies using creatine (methyl-d(3)) and (15)NH(4)Cl have indicated that both the nitrogen and the methyl groups of methylamine had originated from creatine. Furthermore, analysis of cooked meat samples has also confirmed the formation of N-methylacrylamide during cooking.  相似文献   

4.
Analysis of the pyrolysis products of [1-(13)C], [2-(13)C], and [3-(13)C]-labeled L-serines has indicated the presence of three initial degradation pathways. Decarboxylation followed by deamination produces aminoethanol and acetaldehyde, respectively; a retro-aldol pathway generates formaldehyde and glycine. Dehydration of L-serine can lead to the formation of pyruvic acid, which eventually can be converted into the amino acid alanine. Formation of alanine and glycine was confirmed due to the detection of 2, 5-diketo-3,6-dimethylpiperazine and cycloglycylalanine. Most of the advanced decomposition products of L-serine can be rationalized on the basis of these initial degradation products. Label incorporation studies have elucidated the origin of carbonyl precursors of methyl- and 2,3-dimethylpyrazines formed in the thermal decomposition mixture of L-serine. Three mechanistic pathways were identified for the formation of carbonyl precursors of methyl- and 2, 3-dimethylpyrazines. The major pathway (70%) for the formation of the precursor of methylpyrazine involved aldol addition of formaldehyde to glycolaldehyde to form glyceraldehyde. On the other hand, the major pathway (60%) for the formation of the precursor of 2,3-dimethylpyrazine involved an aldol condensation of acetaldehyde with glycolaldehyde to form 2,3-butanedione.  相似文献   

5.
The caramel-like aroma compound, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) was quantified and verified by HPLC and GC-MS in the Maillard reaction based on methylglyoxal (MG). The reaction was performed in the 0.5 M phosphate buffer by heating MG with or without either glycine or cysteine at 120 degrees C for 1 h. MG alone or MG with cysteine could produce increased level of DMHF with pH increased, whereas MG with glycine had contrary trend. Experiments using a 1:1 mixture of [(13)C6]glucose and [(12)C6]glucose indicate that in the presence of glycine or cysteine, glucose skeleton kept intact during DMHF formation since a 1:1 mixture of [(13)C6]DMHF and [(12)C6]DMHF was formed. Acetylformoin was detected in the glucose with amino acid reaction system as a precursor of DMHF, while in the MG reaction systems, acetylformoin could not be identified. It is suggested different pathways of DMHF formation via MG and glucose.  相似文献   

6.
The nucleophilic addition reactions of allyl isothiocyanate (AITC) with alanine, glycine, and five alanine and/or glycine containing di- and tripeptides were investigated in model aqueous solutions of pH 6, 8, and 10 at 25 degrees C for 2-4 weeks. The formation of primary adducts, i.e., N-allylthiocarbamoyl amino acids (ATC-amino acids) or ATC-peptides, their transformation products, i.e., 3-allyl-2-thiohydantoins originating by cyclization of ATC-amino acids or by cleavage of ATC-peptides, and several other minor components were observed. The results revealed that both addition and cleavage rates rise proportionally to pH, whereas the formation of 2-thiohydantoins from ATC-amino acids is controlled by H(3)O(+) concentration. Depending on pH, differences in reaction rates of the additions are determined by either pK(a)(NH(2)) of amino compounds or electrical effects and steric hindrance of the molecules. The latter factors are crucial also for differences in cleavage rates of ATC-peptides. With regard to the pK(a) values and simultaneous AITC decomposition by aqueous nucleophiles, the reactions with amino acids and oligopeptides are predominant reaction pathways of AITC in solutions of pH 10 and 8, respectively. Reaction mechanism of the cleavage of 2-thiohydantoins from ATC-peptides in alkaline and mild acidic solutions is different from the conventional Edman scheme used for anhydrous acid medium.  相似文献   

7.
Twenty-one free amino acids present in several samples of quince fruit (pulp and peel) and quince jam (homemade and industrially manufactured) were analyzed by GC/FID. The analyses showed some differences between quince pulps and peels. Generally, the highest content in total free amino acids and in glycine was found in peels. As a general rule, the three major free amino acids detected in pulps were aspartic acid, asparagine, and hydroxyproline. For quince peels, usually, the three most abundant amino acids were glycine, aspartic acid, and asparagine. Similarly, for quince jams the most important free amino acids were aspartic acid, asparagine, and glycine or hydroxyproline. This study suggests that the free amino acid analysis can be useful for the evaluation of quince jam authenticity. It seems that glycine percentage can be used for the detection of quince peel addition while high alanine content can be related to pear addition.  相似文献   

8.
The effects of adding amino acids on the content of acrylamide in potato crisps, French fries, flat breads, and bread crusts were investigated. Addition of glycine or glutamine during blanching of crisps reduced the amount of acrylamide by approximately 30% compared to no addition. No effect was found in French fries. Addition of glycine during doughmaking significantly reduced acrylamide in both flat breads and bread crusts. In bread crusts the reduction of acrylamide ranged from 50 to >90% depending on the baking condition. In flat breads the reduction varied between 60 and >95%.  相似文献   

9.
On the basis of the recent findings that "biogenic amines" can also be formed during thermal food processing from their parent amino acids in a Strecker-type reaction, the formation of 3-aminopropionamide, the biogenic amine of asparagine, was investigated in model systems as well as in thermally processed Gouda cheese. The results of model studies revealed that, besides acrylamide, 3-aminopropionamide was also formed in amounts of 0.1-0.4 mol % when asparagine was reacted in the presence of either glucose or 2-oxopropionic acid. Results of a second series of model experiments in which [(13)C(4)(15)N(2)]-asparagine ([(13)C(4)(15)N(2)]-Asn) and unlabeled 3-aminopropionamide were reacted together in the presence of glucose revealed a >12-fold higher efficacy of 3-aminopropionamide in acrylamide generation as compared to asparagine. Both [(13)C(3)(15)N(2)]-3-aminopropionamide and [(13)C(3)(15)N(1)]-acrylamide were formed during [(13)C(4)(15)N(2)]-Asn degradation in a ratio of about 1:4, supporting the idea that 3-aminopropionamide is a transient intermediate in acrylamide formation. In this study, 3-aminopropionamide was identified and quantified for the first time in foods, namely, in Gouda cheese. Although the fresh cheese contained low amounts of 3-aminopropionamide, its concentrations were much increased to approximately 1300 mug/kg after thermal processing. In isotope labeling studies, performed by administering to the cheese [(13)C(4)(15)N(2)]-Asn in a ratio of 1:2 as compared to the "natural" concentrations of asparagine, similar ratios of unlabeled/labeled 3-aminopropionamide and unlabeled/labeled acrylamide were determined. Thus, 3-aminopropionamide could be verified as a transient intermediate of acrylamide formation during food processing.  相似文献   

10.
An on-line MS/MS technique was used to study the generation of acrylamide in rye-, wheat-, and potato-based systems during cooking. Acrylamide release to the gas phase was monitored continuously and was correlated with the acrylamide content of samples using a calibration based upon the partition of [1,2,3-(13C3)]acrylamide. On-line results at 180 degrees C were compared with data relating to the same systems obtained through GC-MS analysis. Agreement between the two techniques was notable, both in terms of the temporal profiles of acrylamide generation and when comparing the relative magnitudes of results for potato, wheat, and rye determined by each method. The effects of pH (citric acid) and added amino acids (soy protein hydrolysate) on the generation of acrylamide in hydrated potato flake were modeled at 180 degrees C. It was concluded that a combined treatment of low levels of each additive could result in significant reductions in acrylamide, although the effects of such treatments on sensory properties such as color and flavor remain to be evaluated.  相似文献   

11.
The cocoa roasting process at different temperatures (at 125 and 135 degrees C for 3 min, plus 44 and 52 min, respectively, heating-up times) was evaluated by measuring the initial and final free amino acids distribution, flavor index, formol number, browning measurement, and alkylpyrazines content in 15 cocoa bean samples of different origins. These samples were also analyzed in manufactured cocoa powder. The effect of alkalinization of cocoa was studied. Results indicated that the final concentration and ratio of tetramethylpyrazine/trimethylpyrazine (TMP/TrMP) increased rapidly at higher roasting temperatures. The samples roasted with alkalies (pH between 7.20 and 7.92), such as sodium carbonate, or potassium plus air injected in the roaster during thermal treatment, exhibited a greater degree of brown color formation, but the amount of alkylpyrazines generated was adversely affected. The analysis of alpha-free amino acids at the end of the roasting process demonstrated the importance of the thermal treatment conditions and the pH values on nibs (cocoa bean cotyledons), liquor, or cocoa. Higher pH values led to a lower concentration of aroma and a higher presence of brown compounds.  相似文献   

12.
Wheat flour from plants deficient in sulfur has been shown to contain substantially higher levels of free amino acids, particularly asparagine and glutamine, than flour from wheat grown where sulfur nutrition was sufficient. Elevated levels of asparagine resulted in acrylamide levels up to 6 times higher in sulfur-deprived wheat flour, compared with sulfur-sufficient wheat flour, for three varieties of winter wheat. The volatile compounds from flour, heated at 180 degrees C for 20 min, have been compared for these three varieties of wheat grown with and without sulfur fertilizer. Approximately 50 compounds were quantified in the headspace extracts of the heated flour; over 30 compounds were affected by sulfur fertilization, and 15 compounds were affected by variety. Unsaturated aldehydes formed from aldol condensations, Strecker aldehydes, alkylpyrazines, and low molecular weight alkylfurans were found at higher concentrations in the sulfur-deficient flour, whereas low molecular weight pyrroles and thiophenes and sugar breakdown products were found at higher concentrations in the sulfur-sufficient flour. The reasons for these differences and the relationship between acrylamide formation and aroma volatile formation are discussed.  相似文献   

13.
The changes in amino acid composition that occur with maturity of the Noble cultivar of the Vitis rotundifolia Michx. (muscadine) grape were determined by HPLC. Eighteen amino acids were identified. Histidine was the most prominent amino acid followed by alanine. The concentrations of most of the major amino acids (alanine, glycine, histidine, valine, isoleucine, aspartic acid, and serine) were highest at verasion. Glutamine and threonine contents dropped sharply after fruit set, while those of arginine and proline increased gradually with maturity and ripening. Tyrosine content increased gradually with maturity and ripening following a slight drop after fruit set. In ripe grapes, seeds contained most of the amino acids in mature grapes (50%) followed by the pulp (23%), the juice (15%), and the skin (11%). Alanine, histidine, and arginine were the principal amino acids identified in the juice. Alanine, histidine, arginine, valine, glutamine, aspartic acid, proline, serine, and threonine accounted for about 90% of the amino acids in the pulp. In seeds, alanine, proline, asparagine, and histidine accounted for over 55% of the amino acids, while alanine and histidine were found to be the predominant free amino acids in the skin. The profile indicates some differences in the changes in amino acid composition with berry maturity and relative amounts of amino acids present in muscadine compared to those in nonmuscadine grape species.  相似文献   

14.
The antioxidant activity of fresh and rehydrated sea cucumber (Cucumaria frondosa) samples with/without internal organs was evaluated for the first time. In addition, their proximate, amino acid, and fatty acid compositions were examined. Rehydrated sea cucumber samples in distilled water were prepared from oven-dried products. All samples contained 83-90% moisture, but showed a significant difference among groups in their protein and lipid contents. Glutamic acid was the predominant amino acid in sea cucumber, followed by glycine and aspartic acid. Essential amino acids such as leucine and lysine were also present at high levels. The trend for free amino acid was different from that of total amino acids and varied among groups. Lipids in sea cucumber were dominated by eicosapentaenoic acid (EPA, C20:5n-3), ranging from 43.2 to 56.7% of the total fatty acids. Docosahexaenoic acid (DHA, C22:6n-3) was present at a much lower concentration of 2.0-5.8%. All sea cucumber samples exhibited radical scavenging property against 2,2'-azobis(2-aminopropane) dihydrochloride (AAPH) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, with rehydrated samples, especially those with internal organs, possessing higher antioxidant activity than their fresh counterparts. No correlation existed between radical scavenging capacity and total phenolics content, suggesting that other components, in addition to phenolic compounds, contribute to the antioxidant activity of sea cucumber.  相似文献   

15.
The influences of composition and roasting conditions on acrylamide formation in almonds and hazelnuts were investigated. Eighteen samples of almonds originating from the U.S. and Europe were analyzed for sugars and free amino acids, and acrylamide formed during roasting was determined. Asparagine was the main free amino acid in raw almonds and correlated with the acrylamide content of dark roasted almonds. Roasting temperature was another key factor and had a very strong influence on acrylamide formation. Almonds of European origin contained significantly less free asparagine and formed significantly less acrylamide during roasting as compared to the almonds from the U.S. Roasted hazelnuts contained very little acrylamide because of the low content of free asparagine in the raw nut. Reducing sugars, although being consumed much faster than free amino acids in both types of nuts, were not decisive for the extent of acrylamide formation during roasting.  相似文献   

16.
The aim of this work was to examine the effect of blanching or soaking in different acid solutions on the acrylamide content in potato crisps. Furthermore, the effects of a shorter frying time and a lower frying temperature combined with a postdrying were investigated. Soaking or blanching of potato slices in acidic solutions decreased the pH of potato juice and increased the extraction of amino acids and sugars. Potato crisps obtained after such pretreatments were characterized by lower acrylamide content. The most effective extraction of free amino acids and sugars as well as the largest decrease of acrylamide content (90%) in crisps was obtained when potato slices were soaked in acetic acid solution for 60 min at 20 degrees C. Shorter frying time followed by postdrying resulted in low-moisture potato crisps. Furthermore, the postdrying treatment gave a decreases in acrylamide content of approximately 70% when potato slices were fried at 185 degrees C and approximately 80% when potato slices were fried at 160 degrees C. Effective ways of decreasing acrylamide content in crisps production have been found. Crisps with low acrylamide content and good sensory quality can be obtained either by blanching in acetic acid as pretreatment or by a short frying followed by postdrying.  相似文献   

17.
《Soil biology & biochemistry》2001,33(7-8):1137-1140
Amino acids constitute a major reserve of soil organic-N and studies demonstrating direct uptake of amino acids by plants has indicated that understanding their bioavailability and fate in soil is important to understanding terrestrial N cycling. The aim of this study was to determine the effects of temperature and sorption on the mineralisation of three amino acids (glycine, lysine glutamate) in soil. Amino acid sorption followed the series lysine>glycine>glutamate, whereas mineralisation rate followed the series glutamate>glycine>lysine. These observations support the concept that sorption reduces the bioavailability of amino acids to the soil microbial population. Although the amino acids were used preferentially for making new biomass rather than respiration, differences were apparent between the individual amino acids with microbial assimilation efficiency (biomass production) following the series, lysine>glycine>glutamate. Our results suggest divergences in the uptake and metabolism of the individual amino acids with a rapid mineralisation of amino acids which readily enter general metabolic cycles (e.g. glutamate) compared to the amino acids which typically form the terminus of metabolic pathways (e.g. lysine). Temperature significantly affected the rate of amino acid mineralisation which increased up to 30°C (Q10=2.0) followed by a decline as the temperature approached 40°C. Rapid mineralisation occurred even at very low temperatures (1°C). Amino acid mineralisation across three experimental soil treatments followed the trend acidified>control>eroded soil. In summary, the results indicate that mineralisation is highly amino acid species dependent, has a mesophilic optimum, is retarded by sorption and is most rapid in soils which are not degraded.  相似文献   

18.
玉米浆发酵产生物丁醇的氨基酸代谢动力学模拟   总被引：1，自引：0，他引：1  
为了深入挖掘利用丙酮丁醇梭菌产生物丁醇过程中氨基酸代谢的动态过程,探究利用廉价氮源玉米浆中的氨基酸用于丙酮丁醇梭菌产生物丁醇的生产策略,寻找生产丁醇的高效率廉价氮源来降低发酵生产成本。该研究首先利用高通量测序技术对玉米浆中微生物多样性进行分析;同时基于丙酮丁醇梭菌（Clostridium acetobutylicum）生产丙酮-丁醇-乙醇（Acetone-Butanol-Ethanol,ABE）碳代谢动态模型的基础上,构建氨基酸代谢模型,以此模拟15种氨基酸在利用木糖为碳源发酵生产ABE中的氨基酸代谢过程,并对氨基酸的代谢与丙酮丁醇梭菌的生物量以及ABE的合成相关性关系进行冗余分析;通过模型预测实际生产中利用玉米浆发酵时氨基酸的消耗过程。结果表明,梭状芽胞杆菌属（Clostridium）占细菌总数的68.76%,是玉米浆中的优势菌群;最佳参数校正后构建了氨基酸代谢模型,模拟值与试验值有较好拟合度;11种氨基酸（苯丙氨酸、苏氨酸、异亮氨酸、亮氨酸、蛋氨酸、缬氨酸、酪氨酸、甘氨酸、丝氨酸、精氨酸、天冬酰胺）在培养过程中迅速消耗用于细胞生长和溶剂生成,3种氨基酸（脯氨酸、组织胺、天冬氨酸）保持稳定状态,同时发酵过程中谷氨酰胺积累;冗余分析表明其中5种氨基酸对发酵产物及生物量影响具有相关性（P<0.05）,相关性排序从大到小依次为丝氨酸、甘氨酸、亮氨酸、缬氨酸、天冬酰胺;模拟预测玉米浆中缬氨酸、甘氨酸、丝氨酸在发酵过程中基本被消耗,推测其为发酵后期的营养限制性因子。该结论可证实玉米浆可作为丙酮丁醇梭菌发酵丁醇的优势氮源,为丙酮丁醇梭菌的氨基酸代谢调控及下一步利用并优化玉米浆作为氮源生产生物丁醇提供一定的理论参考和数据支撑。  相似文献   

19.
Fried potato products may accumulate substantial amounts of acrylamide due to high precursor contents, namely reducing sugars and asparagine. In a two-factorial experiment increasing N supply, increased the contents of reducing sugars in most cases, and resulted in higher contents of free amino acids. α -amino-N, which was tightly correlated with the contents of free amino acids, can be regarded a suitable rapid test for free asparagine for a given variety. Increasing K addition always raised the citrate contents, but lessened the contents of reducing sugars. Selected treatments were processed into French fries. Highest acrylamide contents were observed in tubers grown with high N and inadequate K supply, which also contained the highest contents of precursors. The experiment clearly demonstrates that nutrient supply has significant impact on the contents of acrylamide precursors and thus for the acrylamide formation during frying.  相似文献   

20.
In this study different Arabica and Robusta coffee beans from different regions of the world were analyzed for acrylamide after roasting in a laboratory roaster. Due to the complex matrix and the comparably low selectivity of the LC-MS at m/ z 72, acrylamide was analyzed after derivatization with 2-mercaptobenzoic acid at m/ z 226. Additionally, the potential precursors of acrylamide (3-aminopropionamide, carbohydrates, and amino acids) were studied. The highest amounts of acrylamide formed in coffee were found during the first minutes of the roasting process [3800 ng/g in Robusta ( Coffea canephora robusta) and 500 ng/g in Arabica ( Coffea arabica)]. When the roasting time was increased, the concentration of acrylamide decreased. It was shown that especially the roasting time and temperature, species of coffee, and amount of precursors in raw material had an influence on acrylamide formation. Robusta coffee contained significantly larger amounts of acrylamide (mean = 708 ng/g) than Arabica coffee (mean = 374 ng/g). Asparagine is the limiting factor for acrylamide formation in coffee. 3-Aminopropionamide formation was observed in a dry model system with mixtures of asparagine with sugars (sucrose, glucose). Thermal decarboxylation and elimination of the alpha-amino group of asparagine at high temperatures (>220 degrees C) led to a measurable but low formation of acrylamide.  相似文献   

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