Effect of Maillard Reaction Products Derived from Arginine-Glucose Model System on the State of Acrylamide

XIANG Leiwen, WANG Hailin, CHEN Wentao, RAO Pingfan, WANG Shaoyun,*

(1. School of Ocean Science and Biochemistry Engineering, Fuqing Branch of Fujian Normal University, Fuqing 350300, China; 2. College of Biological Science and Engineering, Fuzhou University, Fuzhou 350108, China)

Effect of Maillard Reaction Products Derived from Arginine-Glucose Model System on the State of Acrylamide

XIANG Leiwen1, WANG Hailin1, CHEN Wentao1, RAO Pingfan2, WANG Shaoyun2,*

(1. School of Ocean Science and Biochemistry Engineering, Fuqing Branch of Fujian Normal University, Fuqing 350300, China; 2. College of Biological Science and Engineering, Fuzhou University, Fuzhou 350108, China)

Maillard reaction products (MRPs) formed in foods during heating are found in a wide range of thermally processed foods. The effect of MRPs derived from arginine-glucose model system on the state of acrylamide was investigated in this study. The changes in the spectroscopic properties of MRPs with and without the addition of acrylamide were measured. With the addition of acrylamide, the ultra violet-visible (UV-Vis) spectrum of MRPs showed no signif i cant change, but the fl uorescence spectrum of MRPs showed a signif i cant change in excitation wavelength and emission wavelength. The absorbance of MRPs was 0.327 at 420 nm and the fluorescence intensity of MRPs at an excitation wavelength of 396 nm and an emission wavelength of 462 nm was 96.48. When acrylamide, arginine and glucose were kept in a boiling water bath for 60 min, the absorbance was 0.159 and the fl uorescence intensity was 50.75, indicating a reduction of 51.38% and 47.40%, respectively. The infrared spectroscopic results showed the characteristic absorption peaks of acrylamide at 2 356 and 2 065 cm-1, which disappeared with the addition of acrylamide. The effect of MRPs derived from arginine-glucose model system on the state of acrylamide suggests that the acrylamide may exist in a combined state in the food system, reducing the toxicity of free acrylamide molecules. This work may be helpful for evaluating the safety of acrylamide in food processing as well as providing new insight into the safety of acrylamide and similar materials.

Maillard reaction products; acrylamide; ultra violet-visible spectroscopy; fl uorescence spectroscopym; infrared spectroscopy

Acrylamide is a colorless, odorless, crystalline solid with a low molecular weight and is soluble in water. It has been used in the chemical industry since the 1950s in an intermediate step in the production of polyacrylamide[1]. Acrylamide was first discovered to exist in animal feed in 2000, where it is formed during the heating of the feed[2]. It was inferred that cooking of food results in the majority of acrylamide in human food, but this idea failed to attract the attention of the public. In 2002, acrylamide was found in certain foods that had been subjected to high temperatures[3], having been formed in concentrations on the order of l mg/kg during processing at temperatures above 120 ℃, such as cooking, frying, toasting, roasting or baking of foods that are rich in carbohydrates[4]. It was announced by the National Food Administration in Sweden that high levels of acrylamide were detected in widely consumed processed foods, especially starch-containing foods processed at with high temperature based on analyses that showed these foods containing up to 500 times the levels permitted in potable water by the World Health Organization[5-6]. This is primarily because acrylamide can be formed through pathways closely associated with the Maillard reaction between asparagine and reducing sugars such as glucose and fructose[3,7-8]. Foods that are rich in asparagine and reducing sugars become major sources of acrylamide when fried; such foods are primarily derived from products of plant origin, for example potato[9].

Many studies have demonstrated neurological effects in humans who were exposed to environmental acrylamide[10]. Experimental animals exposed orally to acrylamide suffered cancer occurrences such as tumors of mammary glands in female rats, testicular tumors in male rats, and increased rates of tumors of the thyroid gland, central nervous system, uterus, clitoral gland and oral tissues[11-12]. Acrylamide has been classified as potential human carcinogen (ⅡA), showing reproductive toxicity, genotoxicity and severe neurotoxicity[13]. The content of acrylamide should lower than 0.5 μg/L in the drinking water[14].

Many research studies on acrylamide in food focus on the various impact factors of its formation and the elimination[15-20]. However, the danger of acrylamide is based on the safety assessment of pure acrylamide; the actual existence of acrylamide in the complicated food systems is rarely reported. Acrylamide easily triggers a polymerization reaction at or above the melting point temperature, under oxidative conditions, and under the action of ultraviolet light[21]. Many nucleophilic ingredients in a food system, for example lysine and arginine, can react with acrylamide and inhibit the production of acrylamide[22]. During frying, baking, and other thermal processing of food, extremely complex Maillard reaction products (MRPs) are generated, and acrylamide is only one of them. The presence of a variety of MRPs in a food product may affect the state of acrylamide. The acrylamide may interact with other coexisting MRPs and affect the Maillard reaction process so that the physiological roles of acrylamide and MRPs be changed. The MRPs could neutralize the toxicological effects of acrylamide[23]. Reproducibility of studies on the effect of acrylamides in humans has so far been inconsistent, and the majority of available data on humans comes from prospective population-based epidemiological studies, which have primarily measured acrylamide consumption on the basis of food frequency questionnaires and conversion tables, although some have used the formation of adducts or both methods together[1,24].

In view of the above, in order to better understand the state of dietary acrylamide, the objective of this study is to conduct a systematic observation on the effects of acrylamide on the spectroscopic properties of MRPs. This work investigates the effect of acrylamide on the spectroscopic properties of a model system of arginine-glucose, such as the fluorescence spectrum, ultra violet-visible (UV-Vis) spectrum, and infrared spectrum. The result is signif i cant in that it provides reference for the safety of acrylamide in real food system. This work may be helpful in evaluating the safety of acrylamide and similar materials during the thermal processing of foods.

1 Materials and Methods

1.1 Materials and Reagents

Arginine, glucose, acrylamide, hydrochloric acid, and sodium hydroxide were purchased from Sinopharm Group Pharmaceutical Co. (Shanghai, China). All solvents used were of analytical grade except arginine which was a biochemical reagent. The super-purified water was obtained from the laboratory and was used in the preparation of all samples.

1.2 Instrument and Equipment

UV754N UV-Vis spectrophotometer Shanghai Yoke Instrument Co. Ltd.; 970CRT fl uorescence spectrophotometer Shanghai Precision Scientific Instrument Co. Ltd.; Nicolet 380 Fourier transform infrared spectrometer Thermo Fisher Scientif i c Inc..

1.3 Methods

1.3.1 UV-Vis spectral analysis of samples

To obtain 60 mmol/L of MRPs solution, 10 mL of a solution including 0.6 mmol each of arginine, glucose respectively was added to a 25 mL glass test tube and shake well. The open end of the tubes was tightly wrapped with aluminum foil. The mixed solution was placed in boiling water bath for 60 min. And then the tubes were withdrawn and immediately cooled in an ice-water bath to stop the reaction. 0.6 mmol acrylamide was added to 10 mL of the MRPs solution in a 25 mL glass test tube. The open end of the tubes was tightly wrapped with aluminum foil. The mixed solution was placed in a boiling water bath for 60 min. Afterward, the tubes were withdrawn and immediately cooled in an ice-water bath to stop the reaction. 0.6 mmol acrylamide was added to 10 mL of the MRPs solution in a 25 mL glass test tube and was stored at room temperature (25 ℃) placed in a boiling water bath (100 ℃) for 60 min. All samples were prepared by diluting the solution 100-fold. The diluted samples were scanned by a UV-Vis spectrophotometer at wavelengths ranging from 200-800 nm.

10 mL 60 mmol/L of group 1 (arginine), group 2 (glucose), group 3 (acrylamide), group 4 (arginine + glucose), group 5 (arginine + acrylamide), group 6 (glucose + acrylamide), group 7 (arginine + glucose + acrylamide) solution, respectively, were added to a 25 mL glass test tube. The open end of the tubes was tightly wrapped with aluminum foil. The mixed solution was placed in a boiling water bath for 60 min. Group 8 (MRPs + acrylamide) consisted of 10 mL of MRPs including 0.6 mmol acrylamide placed at room temperature (25 ℃) for 60 min. Afterwards, the tubes were withdrawn and immediately cooled in an icewater bath to stop the reaction. All samples were prepared by diluting the solution 100-fold. The spectral intensity of the diluted samples was determined by a UV-2000 UV-Vis spectrophotometer at 420 nm.

1.3.2 Fluorescence spectral analysis of samples

The fluorescence sample was prepared similar to the UV-Vis spectrophotometer sample. All samples were prepared after the solution was diluted 100-fold. The diluted samples were scanned at full wavelength or were determined at the excitation wavelength of 390 nm and emission wavelength of 451 nm by a 970CRT fluorescence spectrophotometer.

1.3.3 Infrared spectral analysis of samples

The infrared spectrum sample was prepared similar to the UV-Vis spectrophotometer sample. All samples were prepared after the solution was diluted 100-fold. The diluted samples were scanned by an infrared spectrophotometer from 400 to 4 000 cm-1.

1.4 Data analysis

All the experiments were performed in triplicate, and the data analysis was performed using SPSS 17.0 (SPSS, Chicago, IL, USA). Three data points were used to calculate the standard deviation, represented by error bars. Statistical signif i cance was determined by Duncan’s multiple range test (P ＜ 0.05).

2 Results and Analysis

2.1 Effect of acrylamide on UV-Vis spectroscopic properties of MRPs

Fig. 1 UV-Vis absorption spectra of samples

As shown in Fig. 1A, surprisingly, the absorbance of the MRPs of arginine and glucose showed a continuous absorption spectrum in the ultraviolet-visible light range (200-800 nm). There is not a specif i c absorption peak. The absorbance spectrum results indicate that MRPs are a complex system with a series of compounds at different energy levels; those compounds have a continuous absorption in the ultraviolet-visible light ranges. When acrylamide was added to the MRPs solution with different methods, the similar spectra were obtained as shown in Fig. 1B-D. However, the intensity of absorbance has changed. The absorbance of the diluted solution was measured at 420 nm as the literature[25-26]. The detect results of the diluted samples are shown in Fig. 2.

Fig. 2 Effects of various reactants on UV-Vis absorption intensity at 420 nm

After the boiling water bath, the absorbance of the arginine solution, the glucose solution and the acrylamide solution did not make any change. The mixed solution of arginine and acrylamide, and the mixed solution of glucose and acrylamide did not make any change, either. As the reaction continued, the color of the arginine and glucose solution became darker and the reaction became deeper. The absorbance of the MRPs of arginine and glucose was 0.327. When acrylamide, arginine and glucose were placed in boiling water bath for 60 min, the absorbance of the mixed solution was 0.159 at the reduction of 51.38%. When acrylamide was added to the MRPs solution of arginine and glucose and the mixed solution was placed at room temperature (25 ℃) for 60 min, the absorbance of the mixed solution was 0.272 at the reduction of 16.82%. Therefore there is one possibility that an interaction has occurred between MRPs and acrylamide at 25 or 100 ℃. Because the absorbance of the mixed solution didn’t make any change at the co-exist state of either acrylamide and arginine or glucose.

The above phenomenon indicates that the color and the absorbance of the system are closely related to the extent of the reaction, and acrylamide has a signif i cant inf l uence on the ultra violet-visible absorbance of MRPs.

2.2 Effect of acrylamide on fluorescence spectroscopic properties of MRPs

During the Maillard reaction, Strecker degradation of amines can produce some small molecules, so that the fluorescence properties of system change[27]. Under the physiological conditions, glycosylation reactions occur often, and some advanced glycation end products (AGEs) with fluorescent properties can be used as an indicator of Maillard reaction process[28], and as a characteristics molecular of biological study[29-31], even as molecular markers of diabetes (i.e. pentosidine), uremia and other diseases[32]. The fl uorescence scanning results of the diluted samples are presented in Fig. 3 from 200 to 800 nm.

Fig. 3 Fluorescence spectra of samples

As shown in Fig. 3A, the MRPs of arginine and glucose have fl uorescence with an excitation wavelength of 390 nm and emission wavelength of 451 nm. These results are similar to other Maillard reaction systems[33]. As shown in Fig. 3B-D, the fluorescence intensity of the solution with different added methods of acrylamide has significantly changed. And there was a distinct blue-shift in different degrees in the excitation wavelength and the emission wavelength in the sample with acrylamide. The fluorescence intensity of the diluted solution was measured at the excitation wavelength of 390 nm and the emission wavelength of 451 nm. The results are shown in Fig. 4.

Fig. 4 Effect of various reactants on fl uorescence intensity

After a boiling water bath, the fl uorescence intensity of the arginine solution, the glucose solution, and the acrylamide solution did not change. The mixed solution of arginine and acrylamide, and the mixed solution of glucose and acrylamide did not change either. The fluorescence intensity of the MRPs of arginine and glucose was 96.48. When acrylamide, arginine and glucose were placed in a boiling water bath for 60 min, the fl uorescence intensity of the mixed solution was 50.75 at the reduction of 47.40%. When acrylamide was added to the MRPs solution and placed at room temperature for 60 min, the fl uorescence intensity of the mixed solution was 80.03 at the reduction of 17.05%. The above phenomena indicate that acrylamide has a significant influence on the fl uorescence intensity of MRPs as impacting on the UV-Vis absorbance of MRPs. After adding antioxidants, for instance butylated hydroxyanisole, butylated hydroxytoluene, tertbutyl hydroquinone and ascorbic acid, the fluorescence intensity of the model Maillard reaction with asparagineglucose or glycine-glucose would be strengthened[34]. The fl uorescence intensity of the solution changed with time was shown in Fig. 5.

Fig. 5 Fluorescence intensity over time of samples

The fluorescence intensity of the MRPs solution migrates with time. When acrylamide was added to the MRPs solution and placed at room temperature (25 ℃) for 60 min, the fluorescence intensity of the mixed solution increased slowly. The results also indicated that there is an interaction between MRPs and acrylamide at 25 and 100 ℃.

2.3 Effect of acrylamide on infrared spectroscopic properties of MRPs

The infrared spectroscopic scanning results of the diluted samples are presented in Fig. 6 within the wavenumber range of 400 - 4 000 cm-1.

Fig. 6 Infrared spectra of samples

There is a water peak at about 3 400 cm-1because the samples were water-based solutions. As shown in Fig. 6A, the infrared spectroscopic scanning results of acrylamide have some characteristic peaks at 2 356, 2 065, 1 635 cm-1. As shown in Fig. 6B, the infrared spectroscopic scanning results of arginine have some characteristic peaks at 2 065, 1 635, 1 478, 1 406, 1 171 cm-1. As shown in Fig. 6C, the infrared spectroscopic scanning results of glucose have some peaks at 2 361, 2 087, 1 635, 1 419, 1 362, 1 079, 1 034 cm-1. Following a reaction of arginine and glucose, the infrared spectroscopic scanning results of MRPs are shown in Fig. 6D in which there are some peaks at 1 635 cm-1only. The results of MRPs with acrylamide were shown in Fig. 6E-F without the characteristic peaks of acrylamide at 2 356, 2 065 cm-1. The most probable reason was that some groups of arginine or glucose or acrylamide have taken part in the reaction and disappeared.

Thus acrylamide concentration is not always constant. The content of acrylamide would have been changed because of the interaction between the acrylamide and the other compounds in those foods. The elimination of acrylamide has been proposed due to the interaction nucleophilic groups (—SH, —NH2) on amino acid side chains on the acrylamide[35].

Food is a complex system. The acrylamide is only one of the MRPs generated by the Maillard reaction. The high content of acrylamide must be interaction to other MRPs molecules. Thereby, the biological activity of acrylamide and MRPs may be changed in vivo. Although the monomer of acrylamide is stable at room temperature, but acrylamide is a very active compound at or above the melting point temperature, depending on oxidation conditions and the effect of UV.

Acrylamide is prone to the polymerization reaction, hydrolysis reaction, Hoffman reaction and Michaeltype addition reaction. Because the acrylamide molecule contains active amino group and double bond group. Some food nucleophilic reagents, such as lysine, arginine, serine, ascorbic acid and so on, can be combined with acrylamide as reported in prior literature[36].

The experimental results show that acrylamide can inhibit the progress of the Maillard reaction and reduce the fluorescence intensity of MRPs and the characteristic peaks of acrylamide were disappeared after interacting with MRPs. Whether the presence of acrylamide in food can effects on the glycosylation reaction in the human physiological state, as aminoguanidine, carnosine, pyridoxamine, metformin, thiamine pyrophosphate as inhibitors or blockers of the formation of advanced glycation end products[37]needs further study.

3 Conclusions

The Maillard reaction products, formed in foods during heating, consumed by people in a wide range of thermally processed foods. The results show that the acrylamide signif i cantly affects the spectroscopic properties of Maillard reaction products and suggest that acrylamide may exist in a combined state due to interactions in the food system and impact on the toxicity of the free acrylamide molecules. This work may be helpful in evaluating the safety of acrylamide in processed foods and providing new insight into the safety of acrylamide and similar materials.

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精氨酸/葡萄糖的模式美拉德反應(yīng)產(chǎn)物對(duì)丙烯酰胺狀態(tài)的影響

項(xiàng)雷文1，王海林1，陳文韜1，饒平凡2，汪少蕓2,*
（1.福建師范大學(xué)福清分校海洋與生化工程學(xué)院，福建 福清 350300；2.福州大學(xué)生物科學(xué)與工程學(xué)院，福建 福州 350108）

本實(shí)驗(yàn)通過(guò)測(cè)量丙烯酰胺添加前后美拉德反應(yīng)產(chǎn)物的變化，來(lái)研究精氨酸/葡萄糖的模式美拉德反應(yīng)產(chǎn)物對(duì)丙烯酰胺狀態(tài)的影響。結(jié)果表明，添加丙烯酰胺后，美拉德反應(yīng)產(chǎn)物的紫外-可見(jiàn)吸收光譜沒(méi)有明顯變化，但其熒光光譜的吸收波長(zhǎng)和發(fā)射波長(zhǎng)都發(fā)生了明顯變化。美拉德反應(yīng)產(chǎn)物在420 nm波長(zhǎng)處的吸光度為0.327，在吸收波長(zhǎng)396 nm和發(fā)射波長(zhǎng)462 nm條件下，熒光強(qiáng)度為96.48；添加丙烯酰胺并和精氨酸、葡萄糖沸水浴1 h后，其可見(jiàn)光吸收強(qiáng)度為0.159，下降了51.38%，熒光強(qiáng)度為50.75，下降47.40%。紅外掃描結(jié)果表明，丙烯酰胺的特征吸收峰在2 356 cm-1和2 065 cm-1處，加入美拉德反應(yīng)產(chǎn)物溶液后，丙烯酰胺特征峰消失表明其狀態(tài)發(fā)生改變。模式美拉德反應(yīng)產(chǎn)物對(duì)丙烯酰胺的狀態(tài)表明食品中的丙烯酰胺以結(jié)合狀態(tài)存在并因此降低了丙烯酰胺的毒性，可為評(píng)估食品中丙烯酰胺的安全性提供一個(gè)新的視角。

美拉德反應(yīng)產(chǎn)物；丙烯酰胺；紫外-可見(jiàn)光譜；熒光光譜；紅外光譜

TS201

A

1002-6630（2017）07-0029-07

2016-03-15

國(guó)家自然科學(xué)基金面上項(xiàng)目（31571779）；福建省區(qū)域科技重大項(xiàng)目（2014N3005）；福建省教育廳A類(lèi)科技項(xiàng)目（JA10289）

項(xiàng)雷文（1975—），男，教授，博士，主要從事天然產(chǎn)物綜合利用、生物大分子分離與表征、食品中美拉德反應(yīng)研究。E-mail：xiangleiwen@163.com

10.7506/spkx1002-6630-201707006

*通信作者：汪少蕓（1970—），女，教授，博士，主要從事食品化學(xué)、生物活性蛋白質(zhì)、酶和多肽及食品生物技術(shù)研究。E-mail：shywang@fzu.edu.cn

XIANG Leiwen, WANG Hailin, CHEN Wentao, et al. Effect of Maillard reaction products derived from arginine-glucose model system on the state of acrylamide[J]. 食品科學(xué), 2017, 38(7): 29-35.

10.7506/spkx1002-6630-201707006. http://www.spkx.net.cn

XIANG Leiwen, WANG Hailin, CHEN Wentao, et al. Effect of Maillard reaction products derived from arginine-glucose model system on the state of acrylamide[J]. Food Science, 2017, 38(7): 29-35. (in English with Chinese abstract) DOI:10.7506/spkx1002-6630-201707006. http://www.spkx.net.cn